Subscribe

Subscribe to our Newsletter and get informed about new publication regulary and special discounts for subscribers!

ILCPA > Volume 3 > Progress in Elaboration of Nonisocyanate...
< Back to Volume

Progress in Elaboration of Nonisocyanate Polyurethanes Based on Cyclic Carbonates

Full Text PDF

Abstract:

In the article is given a review on synthesis and application nonisocyanate polyurethanes based on cyclic carbonate oligomers. Nonisocyanate polyurethane (NIPU) networks are obtained by reaction between the polycyclic carbonate oligomers and aliphatic or cycloaliphatic polyamines with primary amino groups. This forms a crosslinked polymer with β-hydroxyurethane groups of different structure – polyhydroxyurethane polymer. One of the most interesting derivatives of unsaturated fatty compounds is epoxidized triglyceride oils (ETO), particulary epoxidized soybean oil (ESBO). Until now, ESBO is primarily used as plasticizers for polyvinyl chloride, chlorinated rubber and polyvinyl emulsions to improve their stability and flexibility. Also there are numerous useful derivatives of ETO. Among the various materials, products of reactions of ETO and carbon dioxide (CO2) deserve special attention. A basic composition and a technique for mixing and foaming were developed for insulating foam applied by spraying, the material being based on the use of the synthetic raw materials. UV-curable concrete floor coatings provide a durable, high-performance and eco-friendly solution. These thin-film coating systems cure instantly, thereby minimizing the downtime of any facility. Other benefits of these coatings include excellent chemical resistance, easy cleanability, little odor, and the ability to coat in cold conditions; Fig. 3, Tabl. 3, Ref. 39.

Info:

Periodical:
International Letters of Chemistry, Physics and Astronomy (Volume 3)
Pages:
52-66
Citation:
O. L. Figovsky et al., "Progress in Elaboration of Nonisocyanate Polyurethanes Based on Cyclic Carbonates", International Letters of Chemistry, Physics and Astronomy, Vol. 3, pp. 52-66, 2012
Online since:
October 2012
Export:
Distribution:
References:

[1] Thomson T. Polyurethanes as specialty chemicals: principles and applications. CRC Press, 2005, 190 pages.

[2] Meier-Westhues U. Polyurethanes: coatings, adhesives and sealants. Vincentz Network GmbH & Co KG, Hannover, 2007, 344 pages.

[3] Figovsky O. Thesis, Moscow Civil Engineering Institute, (1971).

[4] Figovsky O., Shapovalov L., Encyclopedia of Surface and Colloid Science, ed. P. Somasundaran, V. 3, 1633-1653. N.Y., Taylor & Francis, (2006).

[5] Leykin A., Beilin D., Birukova O., Figovsky O., Shapovalov L., Scientific Israel – Technological Advantages 11 (3-4) (2009) 160-190.

[6] Guan J., Song Y., Lin Y., Yin X., Zuo M., Zhao Y., Tao X. and Zheng Q., Ind. Eng. Chem. Res. 50 (2011) 6517-6527.

[7] Rappoport L. Ya., Petrov G.N., Trostyanskaya I.I., Gavrilova O.P. Inter. Polymer Sci. Technol. 8 (5), (1981) T/68-T/70.

[8] Yagund E.M., Maklakov L.I., Stroganov V.F., Savchenko V.N., J. Appl. Spectroscopy 45 (1) (1987) 737-741.

[9] Tomita H., Sanda F. Endo T., J. Polymer Sci. A 39 (2001) 851-859.

[10] Bernard J. -M. US Patent 8, 017, 719, 2011; US Patent Application 2011/0288230, (2011).

[11] Moeller T., Kinzelmann H. -G., US Patent 8, 118, 968, (2012).

[12] (a) Muller-Frischinger I., US Patent 8, 003, 737, 2011; (b) Muller-Frischinger I., Gianini M., Volle J., US Patent 8, 263, 687, (2012).

[13] Diakoumakos C.D., http: /appft. uspto. gov/netacgi/nph Parser?Sect1=PTO2&Sect2=HITOFF&p=1&u=%2Fnetahtml%2FPTO%2Fsearch-bool. html&r=1&f=G&l=50&co1=AND&d=PG01&s1=Kotzev&OS=Kotzev&RS=Kotzev - h0http: /appft. uspto. gov/netacgi/nph-Parser?Sect1=PTO2&Sect2=HITOFF&p=1&u=%2Fnetahtml%2FPTO%2Fsearch-bool. html&r=1&f=G&l=50&co1=AND&d=PG01&s1=Kotzev&OS=Kotzev&RS=Kotzev - h2 Kotzev D.L., US Patent 8, 143, 346, 2012. Diakoumakos C.D.,  http: /appft. uspto. gov/netacgi/nph-Parser?Sect1=PTO2&Sect2=HITOFF&p=1&u=%2Fnetahtml%2FPTO%2Fsearch-bool. html&r=1&f=G&l=50&co1=AND&d=PG01&s1=Kotzev&OS=Kotzev&RS=Kotzev - h0http: /appft. uspto. gov/netacgi/nph-Parser?Sect1=PTO2&Sect2=HITOFF&p=1&u=%2Fnetahtml%2FPTO%2Fsearch-bool. html&r=1&f=G&l=50&co1=AND&d=PG01&s1=Kotzev&OS=Kotzev&RS=Kotzev - h2 Kotzev D. L., US Patent Application 2012/0149842, (2012).

DOI: https://doi.org/10.1016/0143-7496(92)90046-x

[14] Klopsch R., Lanver A., Kaffee A., Ebel K., Yu M., US Patent Application 20110306702, (2011).

[15] Mecfel-Marczewski J., Walther B., Mezger J., Kierat R., Staudhamer R., US Patent Application 20110313177, (2011).

[16] Birukov O., Beilin D., Figovsky O., Leykin A., Shapovalov L., US Patent Application 2010/0144966, (2010).

[17] Birukov O., Figovsky O., Leykin A., Shapovalov L., US Pat. 7989553 B2, (2011).

[18] Biermann U., Friedt W., Lang S., Lühs W., Machmüller G., Metzger J.O., Klaas M.R.G., Schäfer H.J., Schneider M.P., Angew. Chem. Int. Ed. 39 (13), (2000) 2206-2224.

DOI: https://doi.org/10.1002/1521-3773(20000703)39:13<2206::aid-anie2206>3.0.co;2-p

[19] Sharma V., Kundu P.P., Prog. Polym. Sci. 31 (11), (2006) 983-1008.

[20] Liu Z.S., Erhan S.Z., Akin D.E., Barton F.E., J. Agric. Food Chem. 54 (6), (2006) 2134-2137.

[21] Crivello J. V., Narayan R., Chem. Mater. 4 (1992) 692-699.

[22] Tamami B., Sohn S., Wilkes G. L., J. Appl. Polym. Sci. 92 (2), (2004) 883-891; Wilkes G. L., Sohn S., Tamami B., US Pat. 7045577, (2006).

[23] Doll K.M. and Erhan S.Z., Green Chem. 7 (12), (2005) 849-854; Doll K.M. and Erhan S.Z., J. Agric. Food Chem. 53 (24), (2005) 9608-9614.

DOI: https://doi.org/10.1021/jf0516179

[24] Parzuchowski P. G., Jurczyk-Kowalska M., Ryszkowska J., Rokicki G., J. App. Polym. Sci. 102 (3), (2006) 2904-2914.

DOI: https://doi.org/10.1002/app.24795

[25] Li Z., Zhao Y., Yan S., Wang X., Kang M., Wang J., Xiang H. Catal Lett. 123 (3-4), (2008).

[26] Javni I., Hong D.P., Petrović Z.S., J. Appl. Polym. Sci. 108 (6), (2008) 3867-3875.

[27] Bähr M., Mülhaupt R., Green Chem. 14, 2, (2012) 483-489; Bähr M., Bitto A., Mülhaupt R., Green Chem. 14, 5, (2012) 1447-1454.

DOI: https://doi.org/10.1039/c2gc35099h

[28] Foltran S., Maisonneuve L., Cloutet E., Gadenne B., Alfos C., Tassaing T., Cramail H., Polym. Chem. 3, 2, (2012).

[29] Mahendran A.R., Aust N., Wuzella G., Müller U., Kandelbauer A., Journal of Polymers and the Environment, Online First™, 28 June (2012).

[30] Birukov O., Figovsky O., Leykin A., Potashnikov R., Shapovalov L., US Patent Application 20120208967, (2012).

[31] Mascia L., Heath R. J., Ng V. S.Y., J. Appl. Polym. Sci. 94 (3), (2004) 1279-1290.

[32] Innocenzi P., Kidchob T., Yoko T., J. Sol-Gel Sci. Technol. 35 (3), (2005) 225-235.

DOI: https://doi.org/10.1007/s10971-005-2290-4

[33] Foscante R.E., Gysegem A.P., Martinich P.J., Law G.H., US Pat. 42500074, (1981).

[34] Mowrer R.N., Foscante R.E., Rojas J.L., US Pat. 5618860, 1997; US Pat. 5804616, 1998; Mowrer R.N., Kane J.F., Hull C.G., US Pat. 5942073, (1999).

[35] Türünç O., Kayaman-Apohan N., Kahraman M.V., Menceloğlu Y., Güngör A., J Sol- Gel Sci Technol. 47 (3), (2008) 290-299.

DOI: https://doi.org/10.1007/s10971-008-1786-0

[36] Hanada K. et al. US Patent Applications: 20120232289, 20120237701 and 20120231184 (2012).

[37] Nakanishi T., Kashida M., Miyawaki S., US Pat. 7425283, 2008; Nakanishi T., Kashida M., Miyawaki S., Ichinohe S., Aramata M., US Pat. 7544759, (2009).

[38] Figovsky O., Shapovalov L., Buslov F. Surface Coatings International Part B: Coatings Transactions 88 (B1), (2005) 67-71.

DOI: https://doi.org/10.1007/bf02699710

[39] Birukov O., Beilin D., Figovsky O., Leykin A., Shapovalov L., US Pat. 7, 820, 779 B2, (2010).

Show More Hide
Cited By:

[1] G. Rokicki, P. Parzuchowski, M. Mazurek, "Non-isocyanate polyurethanes: synthesis, properties, and applications", Polymers for Advanced Technologies, Vol. 26, p. 707, 2015

DOI: https://doi.org/10.1002/pat.3522

[2] E. Leitsch, W. Heath, J. Torkelson, "Polyurethane/polyhydroxyurethane hybrid polymers and their applications as adhesive bonding agents", International Journal of Adhesion and Adhesives, Vol. 64, p. 1, 2016

DOI: https://doi.org/10.1016/j.ijadhadh.2015.09.001

[3] R. Pathak, M. Kathalewar, K. Wazarkar, A. Sabnis, "Non-isocyanate polyurethane (NIPU) from tris-2-hydroxy ethyl isocyanurate modified fatty acid for coating applications", Progress in Organic Coatings, Vol. 89, p. 160, 2015

DOI: https://doi.org/10.1016/j.porgcoat.2015.08.015

[4] L. Maisonneuve, O. Lamarzelle, E. Rix, E. Grau, H. Cramail, "Isocyanate-Free Routes to Polyurethanes and Poly(hydroxy Urethane)s", Chemical Reviews, Vol. 115, p. 12407, 2015

DOI: https://doi.org/10.1021/acs.chemrev.5b00355

[5] M. Levina, D. Miloslavskii, M. Pridatchenko, A. Gorshkov, V. Shashkova, E. Gotlib, R. Tiger, "Green chemistry of polyurethanes: Synthesis, structure, and functionality of triglycerides of soybean oil with epoxy and cyclocarbonate groups—renewable raw materials for new urethanes", Polymer Science Series B, Vol. 57, p. 584, 2015

DOI: https://doi.org/10.1134/S156009041506010X

[6] C. Carré, H. Zoccheddu, S. Delalande, P. Pichon, L. Avérous, "Synthesis and characterization of advanced biobased thermoplastic nonisocyanate polyurethanes, with controlled aromatic-aliphatic architectures", European Polymer Journal, Vol. 84, p. 759, 2016

DOI: https://doi.org/10.1016/j.eurpolymj.2016.05.030

[7] R. Lambeth, S. Mathew, M. Baranoski, K. Housman, B. Tran, J. Oyler, "Nonisocyanate polyurethanes from six-membered cyclic carbonates: Catalysis and side reactions", Journal of Applied Polymer Science, Vol. 134, p. 44941, 2017

DOI: https://doi.org/10.1002/app.44941

[8] R. Tiger, E. Gotlib, "Green chemistry of polyurethanes", Polymer Science, Series D, Vol. 10, p. 9, 2017

DOI: https://doi.org/10.1134/S199542121701021X

[9] S. Panchireddy, J. Thomassin, B. Grignard, C. Damblon, A. Tatton, C. Jerome, C. Detrembleur, "Reinforced poly(hydroxyurethane) thermosets as high performance adhesives for aluminum substrates", Polymer Chemistry, Vol. 8, p. 5897, 2017

DOI: https://doi.org/10.1039/C7PY01209H

[10] M. Levina, M. Zabalov, V. Krasheninnikov, R. Tiger, "Green chemistry of polyurethanes: The catalytic n-butylaminolysis of ethylene carbonate as a model chain-growth reaction in the formation of nonisocyanate polyurethanes", Polymer Science, Series B, Vol. 59, p. 497, 2017

DOI: https://doi.org/10.1134/S1560090417050074

[11] М. Левина, М. Забалов, В. Крашенинников, Р. Тигер, "Зеленая химия полиуретанов: каталитический н-бутиламинолиз этиленкарбоната как модельная реакция роста цепи при образовании неизоцианатных полиуретанов, "Высокомолекулярные соединения. Серия Б"", Высокомолекулярные соединения Б, p. 317, 2017

DOI: https://doi.org/10.7868/S2308113917050072

[12] M. Levina, M. Zabalov, V. Krasheninnikov, R. Tiger, "Comparative Reactivity of Cyclocarbonate Groups of Oligomeric Triglycerides Based on Soybean Oil and Model Compounds in the Reactions of Nonisocyanate Urethane Formation", Polymer Science, Series B, Vol. 60, p. 563, 2018

DOI: https://doi.org/10.1134/S1560090418050081
Show More Hide