Semicrystalline polyamide engineering thermoplastics based on the renewable monomer, 1,9-nonane diamine: Thermal properties and water absorption

Kugel, Alex; He, Jie; Samanta, Satyabrata; Bahr, James; Lattimer, Jessica L.; Fuqua, Michael A.; Ulven, Chad A.; Chisholm, Bret J.

doi:10.1080/03602559.2012.699576

Semicrystalline polyamide engineering thermoplastics based on the renewable monomer, 1,9-nonane diamine: Thermal properties and water absorption

Journal Article · Mon Aug 27 00:00:00 EDT 2012 · Polymer-Plastics Technology and Engineering

DOI:https://doi.org/10.1080/03602559.2012.699576· OSTI ID:1053189

Kugel, Alex ^[1]; He, Jie ^[2]; Samanta, Satyabrata ^[2]; Bahr, James ^[2]; Lattimer, Jessica L. ^[2]; Fuqua, Michael A. ^[2]; Ulven, Chad A. ^[2]; Chisholm, Bret J. ^[2]

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

Here, a series of poly(1,9-nonamethylene adipamide-co-1,9-nonamethylene terephthalamide) copolymers were produced using melt polymerization and the thermal properties, crystal structure, and moisture uptake characterized. The results confirmed that the copolymers exhibit isomorphism. As expected, glass transition temperature and the apparent melting temperature increased with increasing terephthalmide content. Using the difference in the apparent melting temperature to the crystallization temperature as a measure of relative crystallization rate, it was observed that crystallization rate decreased as the terephthalamide content of the copolymer was increased from 0 to 50 mole percent but then sharply increased when increased beyond 50 mole percent. This behavior may be the result of extensive inter- and intramolecular interactions in the melt associated with terephthalmide units in the polymer chain that nucleate crystallization upon cooling below the equilibrium melting temperature. Comparing the thermal properties of copolymers possessing an excess of terephthalmide units to the commodity polyamide Nylon 6,6, it is believed that these copolymers may have utility as partially renewable engineering thermoplastics.

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:: 1053189

Report Number(s):: DOE/GO/88160--47

Journal Information:: Polymer-Plastics Technology and Engineering, Journal Name: Polymer-Plastics Technology and Engineering Journal Issue: 12 Vol. 51; ISSN 0360-2559

Publisher:: Taylor & FrancisCopyright Statement

Country of Publication:: United States

Language:: English

References (37)

Einfluß verzweigter codiole auf das kristallisationsverhalten von aromatischen polyestern Bier, P.; Binsack, R.; Vernaleken, H. Angewandte Makromolekulare Chemie, Vol. 65, Issue 1 https://doi.org/10.1002/apmc.1977.050650101	journal	December 1977
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
Effects of rigid segments on structure and properties of unoriented and oriented poly(p-phenylene terephthalamide-co-ethylene terephthalates) Yamada, Kenji; Hashimoto, Kazuto; Takayanagi, Motowo Journal of Applied Polymer Science, Vol. 33, Issue 5 https://doi.org/10.1002/app.1987.070330519	journal	April 1987
ChemInform Abstract: Plant Oil Renewable Resources as Green Alternatives in Polymer Science Meier, Michael A. R.; Metzger, Juergen O.; Schubert, Ulrich S. ChemInform, Vol. 39, Issue 5 https://doi.org/10.1002/chin.200805269	journal	January 2008
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
On the Lamellar Crystal Structure of Nylons 6,8 and 8,10: A Study Combining Electron Microscopy and Energy Analysis Bermúdez, Marta; León, Salvador; Alemán, Carlos Macromolecular Chemistry and Physics, Vol. 204, Issue 1 https://doi.org/10.1002/macp.200290067	journal	January 2003
Investigation of odd-odd nylons based on undecanedioic acid. 2: Crystal structures Cui, Xiaowen; Li, Weihua; Yan, Deyue Polymer Engineering & Science, Vol. 45, Issue 12 https://doi.org/10.1002/pen.20378	journal	January 2005
The p-phenylene linkage in linear high polymers: Some structure–property relationships Edgar, Owen B.; Hill, Rowland Journal of Polymer Science, Vol. 8, Issue 1 https://doi.org/10.1002/pol.1952.120080101	journal	January 1952
Isomorphous replacement in copolyamide systems: Adipic and terephthalic acids Yu, Arthur J.; Evans, Robert D. Journal of Polymer Science, Vol. 42, Issue 139 https://doi.org/10.1002/pol.1960.1204213926	journal	January 1960
Isomorphism phenomena in macromolecules Natta, G.; Corradini, P.; Sianesi, D. Journal of Polymer Science, Vol. 51, Issue 156, p. 527-539 https://doi.org/10.1002/pol.1961.1205115610	journal	June 1961
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
Isomorphism in synthetic macromolecular systems Allegra, G.; Bassi, I. W. Advances in Polymer Science https://doi.org/10.1007/bfb0051143	book	January 1969
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
Sorption of water by aliphatic polyamides. Review Razumovskii, L. P.; Markin, V. S.; Zaikov, G. Ye Polymer Science U.S.S.R., Vol. 27, Issue 4 https://doi.org/10.1016/0032-3950(85)90411-3	journal	January 1985
Some aspects of the crystallization of ethylene copolymers Isasi, J. R.; Haigh, J. A.; Graham, J. T. Polymer, Vol. 41, Issue 25, p. 8813-8823 https://doi.org/10.1016/s0032-3861(00)00224-x	journal	December 2000
Amide modified polybutylene terephthalate: structure and properties van Bennekom, A. C. M.; Gaymans, R. J. Polymer, Vol. 38, Issue 3 https://doi.org/10.1016/s0032-3861(96)00553-8	journal	February 1997
Polyesteramides based on PET and nylon 2,T Bouma, K.; Groot, G. M. M.; Feijen, J. Polymer, Vol. 41, Issue 8 https://doi.org/10.1016/s0032-3861(99)00480-2	journal	April 2000
Crystal Structure of Novel Polyamides with Long Diacid Segment: Polyamides 2 16, 4 16, 6 16, 8 16, 10 16, and 12 16 Li, Weihua; Yan, Deyue Crystal Growth & Design, Vol. 3, Issue 4 https://doi.org/10.1021/cg034038+	journal	April 2003
Morphology and Structure of Chain-Folded Lamellar Crystals of Nylons 2 22, 4 22, 6 22, 8 22, 10 22, and 12 22 Zhang, Guosheng; Yan, Deyue Crystal Growth & Design, Vol. 4, Issue 2 https://doi.org/10.1021/cg034177r	journal	March 2004
Isomorphous Replacement in Copolyamide Systems. Homologs of Adipic and Terephthalic Acids Yu, Arthur J.; Evans, Robert D. Journal of the American Chemical Society, Vol. 81, Issue 20 https://doi.org/10.1021/ja01529a027	journal	October 1959
Theory of Copolymer Crystallization Helfand, Eugene; Lauritzen, John I. Macromolecules, Vol. 6, Issue 4 https://doi.org/10.1021/ma60034a031	journal	July 1973
Polyamides with a Choice of Structure and Crystal Surface Chemistry. Studies of Chain-Folded Lamellae of Nylons 8 10 and 10 12 and Comparison with the Other 2N 2(N + 1) Nylons 4 6 and 6 8 Jones, N. A.; Atkins, E. D. T.; Hill, M. J. Macromolecules, Vol. 30, Issue 12 https://doi.org/10.1021/ma961494g	journal	June 1997
Comparison of Structures and Behavior on Heating of Solution-Grown, Chain-Folded Lamellar Crystals of 31 Even−Even Nylons Jones, Nathan A.; Atkins, Edward D. T.; Hill, Mary J. Macromolecules, Vol. 33, Issue 7 https://doi.org/10.1021/ma9919559	journal	April 2000
A Novel Method for In Situ Synthesis of Nanostructure Hydroxyapatite–nylon 66 Composites in Tissue Engineering Mehrabanian, Mehran; Nasr-Esfahani, Mojtaba; Jafari, Majid International Journal of Polymeric Materials, Vol. 61, Issue 7 https://doi.org/10.1080/00914037.2011.593061	journal	June 2012
Mechanical Properties and Plastic Deformation of PA-6 and of some of PA-6 Composites and Blends Chiriac, Mihaela; Chiriac, Viorel; Vasile, Cornelia International Journal of Polymeric Materials, Vol. 44, Issue 1-2 https://doi.org/10.1080/00914039908012137	journal	August 1999
Study on the Friction and Wear Behaviors of Modified PA66 Composites Xing, Y.; Zhang, G.; Ma, K. Polymer-Plastics Technology and Engineering, Vol. 48, Issue 6 https://doi.org/10.1080/03602550902824481	journal	May 2009
Studies on Crystal Morphology and Crystallization Kinetics of Polyamide 66 Filled with CaCO ₃ of Different Sizes and Size Distribution Shao, Xiao-Lin; Wei, Yun-Feng; Wu, Li Polymer-Plastics Technology and Engineering, Vol. 51, Issue 6 https://doi.org/10.1080/03602559.2012.659308	journal	April 2012
Effect of Heat Treatment on the Structure and Properties of MC Nylon 6 Xu, Sheng; Zhao, Xiaowen; Ye, Lin Polymer-Plastics Technology and Engineering, Vol. 51, Issue 7 https://doi.org/10.1080/03602559.2012.661902	journal	April 2012
Binary Alloys of Nylon 1010 and Ethylene-Propylene Copolymer: Chemical, Morphological, and Mechanical Analysis Xiaomin, Zhang; Zhihui, Yin; Jinhua, Yin Polymer-Plastics Technology and Engineering, Vol. 36, Issue 2 https://doi.org/10.1080/03602559708000619	journal	March 1997
Chemicals from Biomass Dodds, D. R.; Gross, R. A. Science, Vol. 318, Issue 5854 https://doi.org/10.1126/science.1146356	journal	November 2007
“Green” Chemicals from Renewable Agricultural Biomass - A Mini Review Xu, Yixiang; Hanna, Milford A.; Isom, Loren The Open Agriculture Journal, Vol. 2, Issue 1 https://doi.org/10.2174/1874331500802010054	journal	October 2008
Isomorphism in synthetic macromolecular systems Allegra, G.; Bassi, I. W. Advances in Polymer Science https://doi.org/10.1007/BFb0051143	book	January 1969
Some aspects of the crystallization of ethylene copolymers Isasi, J. R.; Haigh, J. A.; Graham, J. T. Polymer, Vol. 41, Issue 25, p. 8813-8823 https://doi.org/10.1016/S0032-3861(00)00224-X	journal	December 2000
Amide modified polybutylene terephthalate: structure and properties van Bennekom, A. C. M.; Gaymans, R. J. Polymer, Vol. 38, Issue 3 https://doi.org/10.1016/S0032-3861(96)00553-8	journal	February 1997
Plant oil renewable resources as green alternatives in polymer science Meier, Michael A. R.; Metzger, Jürgen O.; Schubert, Ulrich S. Chemical Society Reviews, Vol. 36, Issue 11 https://doi.org/10.1039/b703294c	journal	January 2007

Cited By (3)

Poly(decamethylene terephthalamide) copolymerized with long-chain alkyl dodecanedioic acid: Toward bio-based polymer and improved performances: Research Article Zou, Guangji; Wang, Pingli; Feng, Wutong Journal of Applied Polymer Science, Vol. 135, Issue 31 https://doi.org/10.1002/app.46531	journal	April 2018
Structure and properties of bio‐based polyamide 109 treated with superheated water Tao, Lei; Liu, Ke; Li, Taotao Polymer International, Vol. 68, Issue 8 https://doi.org/10.1002/pi.5835	journal	May 2019
Preparation and properties of biobased polyamides based on 1,9-azelaic acid and different chain length diamines Tao, Lei; Liu, Ke; Li, Taotao Polymer Bulletin, Vol. 77, Issue 3 https://doi.org/10.1007/s00289-019-02791-2	journal	April 2019

Similar Records

MaterialsSemicrystallineCopolyamidesBased on the Renewable Monomer, 1,9-Nonane Diamine

Conference · Wed Dec 15 23:00:00 EST 2010 · OSTI ID:1001335

Polyamides based on the renewable monomer, 1,13-tridecane diamine I: synthesis and characterization of nylon 13,T

Journal Article · Fri May 31 20:00:00 EDT 2013 · Green Materials · OSTI ID:1072208

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

Journal Article · Tue Dec 18 19:00:00 EST 2012 · Polymer · OSTI ID:1059697

Related Subjects

1
9-nonane diamine
36 MATERIALS SCIENCE
nylon
poly(1
9-nonamethylene adipamide-co-1
9-nonamethylene terephthalamide)
polyamide
renewable polymer
semicrystalline polyamide

Semicrystalline polyamide engineering thermoplastics based on the renewable monomer, 1,9-nonane diamine: Thermal properties and water absorption

Citation Formats

References (37)

Cited By (3)

Similar Records

Related Subjects