The polyaddition of isocyanate and polyol to form polyurethane elastomers has rarely been applied to the construction of chiral polyurethane elastomers. Hence, the introduction of chiral units via polyaddition remains a challenging subject in polymer chemistry. In this study, the synthesis of chiral polyurethane elastomers using an aromatic isocyanate, polyols (polyether and polyester polyols), and L(+)-, D(−)-, or meso-tartaric acid by a one-shot method is investigated. The polymers are characterized using FTIR and NMR spectroscopy, and their thermal properties are investigated by TGA, DMA, and DSC analyses. The optical activities of the polymers are confirmed by rotation. The use of chiral tartaric acids is essential to obtain the desired chiral polyurethane elastomers.
References
[1]
Szycher, M. (1999) Szycher’s Handbook of Polyurethanes. CRC Press, Boca Raton, 1.1-9.
[2]
Wirtz, H. and Schulte, K. (1973) Processing of Polyurethane Foam Systems. Kunststoffe, 63, 726-730.
[3]
Avar, G., Meier, W.U., Casselmann, H. and Achten, D. (2012) Polymer Science: A Comprehensive Reference. Polymer Science: A Comprehensive Reference, 10, 411-441.
[4]
Kuehn, A.F. (1986) Polyurethane—A Promising Prospect in Roll Coverings. PIMA, 68, 27-28.
[5]
Gagro, D. (2010) Polyurethanes Overview of the PUR Market. European Coatings Journal, 10, 9-11.
[6]
Bez, W. and Quack, G. (1983) Polyurethane and Latex Foam Carpet Backing Today. Cellular Polymers, 2, 31-53.
[7]
Hare, C.H. (2000) A Review of Polyurethanes: Formulation Variables and their Effects on Performance. Journal of Protective Coatings and Linings, 17, 34-44.
[8]
Paulmann, U. (2015) Polyurethane Elastomers from Polyether Polyol Mixtures and Trimerized Diisocyanates. GER. Offen, DE 102013022173 A1 20150625.
[9]
Qiu, F.-X., Wang, Q., Chen, C.-H., Zhao, H., Liu, J.-H. and Yang, D.-Y. (2013) Sunthesis and Thermos-Optic Properties of Azo Polyurethane Containing Chiral Unit. Key Engineering Materials, 538, 73-76, 5.
[10]
Liu, J.-H., Qiu, F.-X., Cao, G.-R., Shen, Q., Cao, Z.-J. and Yang, D.-Y. (2011) Preparation, Thermos-Optic Property and Transmission Loss of Chiral Azobenzene Polyurethane. Journal of Applied Polymer Science, 121, 2567-2572.http://dx.doi.org/10.1002/app.33980
[11]
Qiu, F.-X., Zhang, W., Liu, J.-H. and Yang, D.-Y. (2010) Optically Active Polyurethane Containing Asymmetric Center: Preparation, Characterization and Thermo-Optic Properties. Polymer-Plastics Technology and Engineering, 49, 1521-1526. http://dx.doi.org/10.1080/03602559.2010.512330
[12]
Zhang, W., Liu, J.-H., Guan, Y.-J., Cao, G.-R., Yang, D.-Y. and Qiu, F.-X. (2010) Preparation of Novel Azo Polyurethane and the Film Thermos-Optic Property. Journal of Optoelectronics Laser, 21, 396-399.
[13]
Cao, G.-R., Guan, Y.-J., Zhang, W., Liu, J.-H., Qiu, F.-X., Yang, D.-Y. and Zhou, Y.-M. (2010) Synthesis, Thermo-Optic Property and Dispersion of Novel Optically Active Azo Polyurethane. Functional Materials, 41, 911-914.
[14]
Qiu, F.-X., Zhang, W., Yang, D.-Y., Zhao, M.-J., Cao, G.-R. and Li, P.-P. (2010) Synthesis, Characterization, and Thermo-Optical Properties of Azobenzene Polyurethane Containing Chiral Units. Journal of Applied Polymer Science, 115, 146-151.
[15]
Gudeangadi, P.G., Sakamoto, T., Shichibu, Y., Konishi, K. and Nakano, T. (2015) Chiral Polyurethane Synthesis Leading to π-Stacked 2/1-Helical Polymer and Cyclic Compounds. ACS Macro Letters, 4, 901-906.
[16]
Varkey, E.C. and Sreekumar, K. (2010) Isosorbide Based Chiral Polyurethanes: Optical and Thermal Studies. Journal of Materials Science, 45, 1912-1920. http://dx.doi.org/10.1007/s10853-009-4177-1
[17]
Huang, S.-H., Bai, Z.-W., Yin, C.-Q. and Li, S.-R. (2006) Covalently Bonding Chiral Polyurethane on Aminated Silica Gel: A New Strategy to Prepare Chiral Stationary Phase for High Performance Liquid Chromatography. Chinese Journal of Polymer Science, 24, 107-114. http://dx.doi.org/10.1142/S0256767906001102
[18]
Lui, J.-H., Tai, F.-R. and Lai, Y.-C. (1995) Synthesis of Chiral Polymer Having Camphanediol Moieties and Their Optical Resolution of Some Racemates. Journal of Applied Polymer Science, 58, 1713-1720.
[19]
Lui, J.-H., Tsai, F.-R. and Lai, Y.-C. (1995) Synthesis and Characteristics of Chiral Polymers with Camphanediol Moieties. Die Angewante Makromolekulare Chemie, 231, 35-45. http://dx.doi.org/10.1002/apmc.1995.052310104
[20]
Haider, K.W., Chan, J.C., Jonsson, E.H. and Franz, U.W. (2001) Hydrophobic Polyurethane Elastomer. US 6211324 B1 20010403.
[21]
Chen, C.-F., Su, Q., Chen, Y.-M. and Xi, F. (1999) A New Optically Active Polyurethane Derived from Chiral (2R, 3R) (+)-Diethyl L-Tartrate and Diisocyanate. Chinese Journal of Polymer Science, 17, 371-373.
[22]
Behr, J.P., Girodeau, J.M., Hayward, R.C., Lehn, J.M. and Sauvage, J.P. (1980) Molecular Receptors. Functionalized and Chiral Macrocyclic Polyethers Derived from Tartaric acid. Helvetica Chimica Acta, 63, 2096-2111. http://dx.doi.org/10.1002/hlca.19800630736
[23]
Gryko, D.T., Piatek, P. and Jurczak, J. (1999) An Efficient Method for Preparation of Chiral Macrocyclic Bisamides Starting from Diol Derivatives of D-Mannitol and L-Tartaric Acid. Synthesis, 2, 336-340. http://dx.doi.org/10.1055/s-1999-6054
[24]
Li, B., Yang, X., Yang, K. and Fu, E. (2005) Synthesis of Novel Chiral Macrocyclic Polyamides Derived from L-/D-Tartaric Acid. Synthetic Communications, 35, 2603-2608. http://dx.doi.org/10.1080/00397910500214235
[25]
Li, B., Yang, X., Wu, X., Luo, X., Zhong, C. and Fu, E. (2006) Enantioselective Recognition for Carboxylic Acids by Novel Chiral Macrocyclic Polyamides Derived from L-/D-Tartaric Acid. Supramolecular Chemistry, 18, 507-513.http://dx.doi.org/10.1080/10610270600808141
[26]
Seebach, D., Crass, G., Wilka, E.M., Hilvert, D. and Brunner, E. (1979) Three New Chiral Aminoethers from Tartaric Acid for Improved Asymmetric Syntheses with Organolithium Reactions. Preliminary Communication. Helvetica Chimica Acta, 62, 2695-2698. http://dx.doi.org/10.1002/hlca.19790620819
[27]
Nitta, Y., Sekine, F., Imanaka, T. and Teranishi, S. (1982) Effect of Preparation Variables on Enantioselectivity of Supported Nickel Catalysts Modified with Tartaric Acid. Journal of Catalysis, 74, 382-392. http://dx.doi.org/10.1016/0021-9517(82)90043-4
[28]
Gao, J.-M., Liu, W.-T., Li, M.-L., Liu, H.-W., Zhang, X.-C. and Li, Z.-X. (2008) Preparation and Structural Elucidation of (−)-Tetrahydroberberine-(+)-2,3-Di(P-Toluyl) Tartaric Acid Complex. Journal of Molecular Structure, 892, 466-469. http://dx.doi.org/10.1016/j.molstruc.2008.06.013
[29]
Kimino, T. and Fujii, I. (2010) Crystal Structure of (2R, 3R)-Tartaric Acid Complex of (R)-Nipecotic Acid Ethyl Ester. X-Ray Structure Analysis Online, 26, 11-12. http://dx.doi.org/10.2116/xraystruct.26.11
[30]
Sevukarajan, M., Sodanapalli, R., Thanuja, B., and Nair, R. (2011) Preparation and Pharmaceutical Characterization of Supra Molecular Complex of Isoniazid with L(+) Tartaric Acid. Journal of Biomedical Sciences and Research, 3, 397-402.
[31]
Violante de Paz, M., Marín, R., Zamora, F., Hakkou, K., Alla, A., Galbis, J.A. and Muñoz-Guerra, S. (2007) Linear Polyurethanes Derived from Alditols and Diisocyanates. Journal of Polymer Science, 45, 4109-4117. http://dx.doi.org/10.1002/pola.22127
[32]
Marín, R., Martínez de Ilarduya, A. and Muñoz-Guerra, S. (2009) Linear Polyurethanes Made from Naturally Occurring Tartaric Acid. Journal of Polymer Science, 47, 2391-2407. http://dx.doi.org/10.1002/pola.23330
[33]
Hatakeyama, H., Hirose, S. and Hatakeyama, T. (1995) Biodegradable Polyurethanes from Plant Components. Journal of Macromolecular Science, Part A: Pure and Applied Chemistry, 32, 743-750.http://dx.doi.org/10.1080/10601329508010285
[34]
Wang, G. and Zhou, A. (2011) Soy Protein Based Biodegradable Flexible Polyurethane Foam. Advanced Materials Research, 152, 1862-1865. http://dx.doi.org/10.4028/www.scientific.net/AMR.264-265.1862
[35]
Asano, Y. and Hatakeyama, H. (2003) Rigid Type Polyurethane Foams Containing Saccharide and Lignin Structures in the Molecular Chain. Memoirs of Fukui University of Technology, 33, 275-282.
[36]
Hatakeyama, H. and Hatakeyama, T. (2005) Environmentally Compatible Hybrid-Type Polyurethane Foams Containing Saccharide and Lignin Components. Macromolecular Symposia, 224, 219-226. http://dx.doi.org/10.1002/masy.200550619
[37]
Chen, Q., Li, R., Sun, K., Li, J. and Liu, C. (2011) Preparation of Bio-Degradable Polyurethane Foams from Liquefied Wheat Straw. Advanced Materials Research, 217-218, 1239-1244.http://dx.doi.org/10.4028/www.scientific.net/amr.217-218.1239
[38]
Garcon, R., Clerk, C., Gesson, J.-P., Bordado, J., Nunes, T., Caroco, S., Gomes, P.T., Minas da Piedade, M.E. and Rauter, A.P. (2001) Synthesis of Novel Polyurethanes from Sugars and 1,6-Hexamethylene Diisocyanate. Carbohydrate Polymers, 45, 123-127. http://dx.doi.org/10.1016/S0144-8617(00)00323-4
[39]
Lim, H., Kim, E.Y. and Kim, B.K. (2010) Polyurethane Foams Blown with Various Types of Environmentally Friendly Blowing Agents. Plastics, Rubber and Composites, 39, 364-369. http://dx.doi.org/10.1179/174328910X12691245469835
[40]
Ionescu, M., Mihalache, I., Zugravu, V. and Mihai, S. (1994) Inherently Flame Retardant Rigid Polyurethane Foams Based on New Triazinic Polyether Polyols. Cellular Polymers, 13, 57-68.
