Polyamides based on the renewable monomer, 1,13-tridecane diamine II: Synthesis and characterization of nylon 13,6

Samanta, Satyabrata; He, Jie; Selvakumar, Sermadurai; Lattimer, Jessica; Ulven, Chad; Sibi, Mukund; Bahr, James; Chisholm, Bret J.

doi:10.1016/j.polymer.2012.12.034

Polyamides based on the renewable monomer, 1,13-tridecane diamine II: Synthesis and characterization of nylon 13,6

Journal Article · Wed Dec 19 00:00:00 EST 2012 · Polymer

DOI:https://doi.org/10.1016/j.polymer.2012.12.034· OSTI ID:1059697

Samanta, Satyabrata ^[1]; He, Jie ^[2]; Selvakumar, Sermadurai ^[2]; Lattimer, Jessica ^[2]; Ulven, Chad ^[2]; Sibi, Mukund ^[2]; Bahr, James ^[2]; Chisholm, Bret J. ^[2]

North Dakota State Univ., Fargo, ND (United States); North Dakota State University
North Dakota State Univ., Fargo, ND (United States)

The nylon 13,6 was successfully synthesized and its chemical composition, thermal properties, crystal structure, and moisture absorption characterized. Melting temperature and glass transition temperature were determined to be 206 °C and 60 °C, respectively, while the equilibrium melting temperature was determined to be 248 °C. Characterization of the crystallization kinetics showed that nylon 13,6 exhibits very fast crystallization compared to the industrially important nylons, nylon 6 and nylon 6,6. Additionally, the moisture absorption of nylon 13,6 was dramatically lower than nylon 6 and nylon 6,6 which is consistent with the much lower amide content of nylon 13,6. The crystal structure was determined to be different from the expected γ-form, which possess a pseudohexagonal unit cell. Instead, the x-ray scattering pattern was more similar to the α-form. Furthermore, a similar result has been obtained for other odd–even nylons including nylon 5,6, nylon 5,10, nylon 9,2, nylon 11,10, and nylon 11,12.

View Accepted Manuscript (DOE)

Research Organization:: North Dakota State Univ., Fargo, ND (United States)

Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE)

Grant/Contract Number:: FG36-08GO88160

OSTI ID:: 1059697

Report Number(s):: DOE/GO/88160--49

Journal Information:: Polymer, Journal Name: Polymer Journal Issue: 3 Vol. 54; ISSN 0032-3861

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

References (44)

Nylon 6 9 can crystallize with hydrogen bonding in two and in three interchain directions Franco, L.; Cooper, S. J.; Atkins, E. D. T. Journal of Polymer Science Part B: Polymer Physics, Vol. 36, Issue 7 https://doi.org/10.1002/(sici)1099-0488(199805)36:7<1153::aid-polb6>3.0.co;2-v	journal	May 1998
On the crystal structure of odd-even nylons: Polymorphism of nylon 5,10 Villase�or, P.; Franco, L.; Subirana, J. A. Journal of Polymer Science Part B: Polymer Physics, Vol. 37, Issue 17 https://doi.org/10.1002/(sici)1099-0488(19990901)37:17<2383::aid-polb9>3.0.co;2-g	journal	September 1999
Synthesis and crystallization behavior of nylon 12,14. I. Preparation and melting behavior Li, Yongjin; Zhang, Guosheng; Yan, Deyue Journal of Applied Polymer Science, Vol. 88, Issue 6 https://doi.org/10.1002/app.11826	journal	February 2003
Détermination de la viscosité intrinsèque de solutions de polymères par une simple détermination de la viscosité Solomon, O. F.; Ciutǎ, I. Z. Journal of Applied Polymer Science, Vol. 6, Issue 24, p. 683-686 https://doi.org/10.1002/app.1962.070062414	journal	November 1962
Copolyamides derived from brassylic acid Kim, Ki-Soo; Yu, Arthur J. Journal of Applied Polymer Science, Vol. 23, Issue 2 https://doi.org/10.1002/app.1979.070230213	journal	January 1979
Kinetics of isothermal and nonisothermal crystallization of nylon 1313 Wang, Yudong; Liu, Minying; Wang, Zhimin Journal of Applied Polymer Science, Vol. 104, Issue 3 https://doi.org/10.1002/app.24594	journal	January 2007
An investigation of the structures of polyamide series Kinoshita, Yukio Die Makromolekulare Chemie, Vol. 33, Issue 1, p. 1-20 https://doi.org/10.1002/macp.1959.020330101	journal	January 1959
The crystal structure of polyheptamethylene pimelamide (nylon 77) Kinoshita, Yukio Die Makromolekulare Chemie, Vol. 33, Issue 1, p. 21-31 https://doi.org/10.1002/macp.1959.020330102	journal	January 1959
A barometer of crystallization rates of polymeric materials Khanna, Y. P. Polymer Engineering and Science, Vol. 30, Issue 24, p. 1615-1619 https://doi.org/10.1002/pen.760302410	journal	December 1990
Nylon 1313: Synthesis and polymerization of monomers Greene, Joseph L.; Huffman, Everett L.; Burks, Robert E. Journal of Polymer Science Part A-1: Polymer Chemistry, Vol. 5, Issue 2 https://doi.org/10.1002/pol.1967.150050214	journal	February 1967
Structural data and thermal studies on nylon-12,10 Franco, Lourdes; Puiggalí, Jordi Journal of Polymer Science Part B: Polymer Physics, Vol. 33, Issue 14 https://doi.org/10.1002/polb.1995.090331408	journal	October 1995
Structural studies of nylon 13,13 Prieto, A.; Iribarren, I.; Muñoz-Guerra, S. Journal of Materials Science, Vol. 28, Issue 15 https://doi.org/10.1007/bf00351232	journal	January 1993
Sebacic acid and 2-octanol from castor oil Vasishtha, A. K.; Trivedi, R. K.; Das, G. Journal of the American Oil Chemists' Society, Vol. 67, Issue 5 https://doi.org/10.1007/bf02539685	journal	May 1990
Cost analyses for new products and processes developed in USDA laboratories Sohns, V. E. Journal of the American Oil Chemists’ Society, Vol. 48, Issue 9 https://doi.org/10.1007/bf02544644	journal	September 1971
Development of new crops for industrial raw materials Princen, L. H.; Rothfus, J. A. Journal of the American Oil Chemists' Society, Vol. 61, Issue 2 https://doi.org/10.1007/bf02678782	journal	February 1984
Crystallization and morphology of nylon-6,6 crystals: 1. Solution crystallization and solution annealing behaviour Magill, J. H.; Girolamo, M.; Keller, A. Polymer, Vol. 22, Issue 1 https://doi.org/10.1016/0032-3861(81)90075-6	journal	January 1981
Renewable resources in coatings technology: a review Derksen, Johannes T. P.; Petrus Cuperus, F.; Kolster, Peter Progress in Organic Coatings, Vol. 27, Issue 1-4 https://doi.org/10.1016/0300-9440(95)00518-8	journal	January 1996
Preparation, characterization and crystalline transitions of odd–even polyamides 11,12 and 11,10 Cui, Xiaowen; Yan, Deyue European Polymer Journal, Vol. 41, Issue 4 https://doi.org/10.1016/j.eurpolymj.2004.10.045	journal	April 2005
Plant oils: The perfect renewable resource for polymer science?! Montero de Espinosa, Lucas; Meier, Michael A. R. European Polymer Journal, Vol. 47, Issue 5, p. 837-852 https://doi.org/10.1016/j.eurpolymj.2010.11.020	journal	May 2011
Brill transition and melt crystallization of nylon 56: An odd–even polyamide with two hydrogen-bonding directions Morales-Gámez, Laura; Soto, David; Franco, Lourdes Polymer, Vol. 51, Issue 24 https://doi.org/10.1016/j.polymer.2010.09.074	journal	November 2010
13-Aminotridecanoic Acid from Erucic Acid Greene, Joseph L.; Burks, Robert E.; Wolff, I. A. Product R&D, Vol. 8, Issue 2 https://doi.org/10.1021/i360030a015	journal	June 1969
Brassylic Acid: Chemical Intermediate from High-Erucic Oils Carlson, Kenneth D.; Sohns, Virgil E.; Perkins, R. Beltron Product R&D, Vol. 16, Issue 1 https://doi.org/10.1021/i360061a020	journal	March 1977
Nylon-1313 from Brassylic Acid Nieschlag, H. J.; Rothfus, J. A.; Sohns, V. E. Product R&D, Vol. 16, Issue 1 https://doi.org/10.1021/i360061a021	journal	March 1977
Obtaining 2-Octanol, 2-Octanone, and Sebacic Acid from Castor Oil by Microwave-Induced Alkali Fusion Azcan, Nezihe; Demirel, Elif Industrial & Engineering Chemistry Research, Vol. 47, Issue 6 https://doi.org/10.1021/ie071345u	journal	March 2008
Studies on Polymerization and ring Formation. i. an Introduction to the General Theory of Condensation Polymers Carothers, Wallace H. Journal of the American Chemical Society, Vol. 51, Issue 8 https://doi.org/10.1021/ja01383a041	journal	August 1929
Studies on Polymerization and ring Formation. ii. Poly-Esters Carothers, Wallace H.; Arvin, J. A. Journal of the American Chemical Society, Vol. 51, Issue 8 https://doi.org/10.1021/ja01383a042	journal	August 1929
NMR study of nylon 66 in solution (proton, carbon-13, and nitrogen-15 NMR using adiabatic J cross polarization) Holmes, B. S.; Moniz, W. B.; Ferguson, Raymond C. Macromolecules, Vol. 15, Issue 1 https://doi.org/10.1021/ma00229a026	journal	January 1982
Structure and Morphology of Odd Polyoxamides [Nylon 9,2]. A New Example of Hydrogen-Bonding Interactions in Two Different Directions Franco, L.; Subirana, J. A.; Puiggalí, J. Macromolecules, Vol. 31, Issue 12 https://doi.org/10.1021/ma971599z	journal	May 1998
Crystal Structures of Nylon 5,6. A Model with Two Hydrogen Bond Directions for Nylons Derived from Odd Diamines Puiggalí, J.; Franco, L.; Alemán, C. Macromolecules, Vol. 31, Issue 24 https://doi.org/10.1021/ma971895b	journal	October 1998
Vegetable oil-based polymeric materials: synthesis, properties, and applications Xia, Ying; Larock, Richard C. Green Chemistry, Vol. 12, Issue 11 https://doi.org/10.1039/c0gc00264j	journal	January 2010
Synthesis of biodegradable polymers from renewable resources Tschan, Mathieu J. -L.; Brulé, Emilie; Haquette, Pierre Polym. Chem., Vol. 3, Issue 4 https://doi.org/10.1039/c2py00452f	journal	January 2012
Kinetics of Phase Change. I General Theory Avrami, Melvin The Journal of Chemical Physics, Vol. 7, Issue 12, p. 1103-1112 https://doi.org/10.1063/1.1750380	journal	December 1939
Kinetics of Phase Change. II Transformation‐Time Relations for Random Distribution of Nuclei Avrami, Melvin The Journal of Chemical Physics, Vol. 8, Issue 2 https://doi.org/10.1063/1.1750631	journal	February 1940
Semicrystalline Polyamide Engineering Thermoplastics Based on the Renewable Monomer, 1,9-Nonane Diamine: Thermal Properties and Water Absorption Kugel, Alex; He, Jie; Samanta, Satyabrata Polymer-Plastics Technology and Engineering, Vol. 51, Issue 12, p. 1266-1274 https://doi.org/10.1080/03602559.2012.699576	journal	August 2012
Melting process and the equilibrium melting temperature of polychlorotrifluoroethylene Hoffman, John D.; Weeks, James J. Journal of Research of the National Bureau of Standards Section A: Physics and Chemistry, Vol. 66A, Issue 1 https://doi.org/10.6028/jres.066a.003	journal	January 1962
Nylon 6 9 can crystallize with hydrogen bonding in two and in three interchain directions Franco, L.; Cooper, S. J.; Atkins, E. D. T. Journal of Polymer Science Part B: Polymer Physics, Vol. 36, Issue 7 https://doi.org/10.1002/(SICI)1099-0488(199805)36:7<1153::AID-POLB6>3.0.CO;2-V	journal	May 1998
On the crystal structure of odd-even nylons: Polymorphism of nylon 5,10 Villase�or, P.; Franco, L.; Subirana, J. A. Journal of Polymer Science Part B: Polymer Physics, Vol. 37, Issue 17 https://doi.org/10.1002/(SICI)1099-0488(19990901)37:17<2383::AID-POLB9>3.0.CO;2-G	journal	September 1999
Structural studies of nylon 13,13 Prieto, A.; Iribarren, I.; Muñoz-Guerra, S. Journal of Materials Science, Vol. 28, Issue 15 https://doi.org/10.1007/BF00351232	journal	January 1993
Sebacic acid and 2-octanol from castor oil Vasishtha, A. K.; Trivedi, R. K.; Das, G. Journal of the American Oil Chemists' Society, Vol. 67, Issue 5 https://doi.org/10.1007/BF02539685	journal	May 1990
Cost analyses for new products and processes developed in USDA laboratories Sohns, V. E. Journal of the American Oil Chemists’ Society, Vol. 48, Issue 9 https://doi.org/10.1007/BF02544644	journal	September 1971
Development of new crops for industrial raw materials Princen, L. H.; Rothfus, J. A. Journal of the American Oil Chemists' Society, Vol. 61, Issue 2 https://doi.org/10.1007/BF02678782	journal	February 1984
Synthesis of biodegradable polymers from renewable resources Tschan, Mathieu J. -L.; Brulé, Emilie; Haquette, Pierre Polym. Chem., Vol. 3, Issue 4 https://doi.org/10.1039/C2PY00452F	journal	January 2012
Multiple Melting and Crystallization Behavior of Nylon 1212 Song, Jian-bin; Chen, Qing-yong; Ren, Min-qiao Chinese Journal of Polymer Science, Vol. 24, Issue 2, p. 187 https://doi.org/10.1142/S0256767906001199	journal	January 2006
Melting process and the equilibrium melting temperature of polychlorotrifluoroethylene Hoffman, John D.; Weeks, James J. Journal of Research of the National Bureau of Standards Section A: Physics and Chemistry, Vol. 66A, Issue 1 https://doi.org/10.6028/jres.066A.003	journal	January 1962

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