Top

Polymer Bulletin

Published in:

18-04-2017 | Original Paper

Bio-based poly(pentamethylene oxamide) synthesized by spray/solid-state polycondensation

Authors: Cong Cheng, Fredrick Nzioka Mutua, Yusheng Dong, Bo Zhu, Yong He

Published in: Polymer Bulletin | Issue 1/2018

Activate our intelligent search to find suitable subject content or patents.

search-config

AI-assisted search

Off

Abstract

In this study, an attempt was made to prepare bio-based poly(pentamethylene oxamide) (PA52) using a novel process of spray/solid-state polycondensation. A prepolymer of relative viscosity of 1.3 was prepared by spray polycondensation, where the monomers (dibutyl oxalate and 1,5-pentanediamine) were separately injected into the nozzle, atomized simultaneously under nitrogen flow, mixed, and polymerized at room temperature. After solid-state polycondensation, PA52 with relative viscosity of 3.2, weight-average molecular weight of 4.3 × 10⁴, and melting point of 301 °C was obtained. FTIR and ¹H-NMR analysis confirmed the formation of PA52 while the DSC results suggested that the resultant polymer possessed high heat resistance and good crystallizability.

previous article Synthesis of waste cooking oil-based polyurethane for solid polymer electrolyte

next article Comparative studies of thermo-mechanical and morphological properties of polylactic acid/fumed silica/clay (1.28E) and polylactic acid/fumed silica/clay (1.34TCN) nanocomposites

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

über 102.000 Bücher
über 537 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Finance + Banking
Management + Führung
Marketing + Vertrieb
Maschinenbau + Werkstoffe
Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

inform now

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

über 67.000 Bücher
über 390 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Maschinenbau + Werkstoffe

Jetzt Wissensvorsprung sichern!

inform now

Shalaby SW, Pearce EM, Fredericks RJ, Turi EA (1973) Structure and thermal stability of aliphatic polyoxamides. J Polym Sci Polym Phys Edt 11(1):1–14CrossRef

Kurachi K (2011) C1 chemistry-derived high performance polymers. Focus on polyoxamide. Purasuchikkusu Eji 57(1):72–76

Stamatoff GS, Symons NKJ (1966) US Patent 1966, 3,247,168. US3247168

Gaymans RJ, Venkatraman VS, Schuijer J (1984) Preparation and some properties of nylon-4,2. J Polym Sci Polym Chem Edt 22(6):1373–1382CrossRef

Nakagawa T, Nozaki K, Maeda S, Yamamoto T (2015) Polymorphism of poly(nonamethyleneoxamide) crystal. Polymer 57:99–104. doi:10.1016/j.polymer.2014.12.022 CrossRef

Nakagawa T, Maeda S, Nozaki K, Yamamoto T (2014) Crystal structure of an aliphatic polyoxamide containing methyl side-groups: poly(2-methyl-1,8-octamethyleneoxamide). Polymer 55(9):2254–2261. doi:10.1016/j.polymer.2014.03.009 CrossRef

Vogl O, Knight AC (1968) Polyoxamides. I. Preparation and characterization of cyclic oxamides. Macromolecules 1(4):311–315. doi:10.1021/ma60004a006 CrossRef

Chatani Y, Ueda Y, Tadokoro H, Deits W, Vogl O (1978) Structure of poly(hexamethylene oxamide) [nylon 62]. Macromolecules 11(4):636–638. doi:10.1021/ma60064a003 CrossRef

Dickstein W, Vogl O (1984) Regular copolyamides. IX. Some aliphatic aromatic copolyoxamides. J Macromol Sci Chem A21(6–7):847–857. doi:10.1080/00222338408077247 CrossRef

10.

Wang J, Nomura R, Endo T (1997) One-pot syntheses of water-soluble poly(oxamide)s. Polym Bull (Berlin) 38(2):125–132. doi:10.1007/s002890050028 CrossRef

11.

Casas MT, Armelin E, Aleman C, Puiggali J (2002) On the crystalline structure of even polyoxalamides. Macromolecules 35(23):8781–8787. doi:10.1021/ma020869 CrossRef

12.

Franco L, Subirana JA, Puiggalí J (1998) Structure and morphology of odd polyoxamides [nylon 9,2]. A new example of hydrogen-bonding interactions in two different directions. Macromolecules 31(12):3912–3924. doi:10.1021/ma971599z CrossRef

13.

Maeda S, Kurachi K, Okushita H, Hanaoka Y, Yabu N, Nakagawa T (2012) WO 2012036303. WO2012036303A1

14.

Kurachi K, Hanaoka Y, Maeda S, Okushita H (2012) JP Patent 2012072200. JP2012072200A

15.

Vogl O, Knight AC (1968) Polyoxamides. II. Polymerization of cyclic diamides. Macromolecules 1(4):315–318. doi:10.1021/ma60004a007 CrossRef

16.

Chang HJ, Vogl O (1977) Regular copolyamides. II. Preparation and characterization of regular aliphatic copolyoxamides. J Polym Sci Polym Chem Edt 15(5):1043–1060. doi:10.1002/pol.1977.170150503 CrossRef

17.

Chang HJ, Vogl O (1977) Regular copolyamides. I. A facile method for the preparation of diamine-oxamides. J Polym Sci Polym Chem Edt 15(2):311–322. doi:10.1002/pol.1977.170150205 CrossRef

18.

Grossman S, Vogl O (1980) Regular copolyamides by solution and liquid-liquid interfacial polymerization. Org Coat Plast Chem 42:116–121

19.

Okushita H, Kurachi K, Shimokawa M (2008) WO2008123531. WO2008123531A1

20.

Kind S, Wittmann C (2011) Bio-based production of the platform chemical 1,5-diaminopentane. Appl Microbiol Biotechnol 91(5):1287–1296. doi:10.1007/s00253-011-3457-2 CrossRef

21.

Ikeda N, Miyamoto M, Adachi N, Nakano M, Tanaka T, Kondo A (2013) Direct cadaverine production from cellobiose using β-glucosidase displaying Escherichia coli. AMB Expr 3(1):67/61–67/67. doi:10.1186/2191-0855-3-67 CrossRef

22.

Mimitsuka T, Sawai H, Hatsu M, Yamada K (2007) Metabolic engineering of corynebacterium glutamicum for cadaverine fermentation. Biosci Biotechnol Biochem 71(9):2130–2135. doi:10.1271/bbb.60699 CrossRef

23.

Ma W, Cao W, Zhang H, Chen K, Li Y, Ouyang P (2015) Enhanced cadaverine production from l-lysine using recombinant Escherichia coli co-overexpressing CadA and CadB. Biotechnol Lett 37(4):799–806. doi:10.1007/s10529-014-1753-5 CrossRef

24.

Matsushima Y, Hirasawa T, Shimizu H (2016) Enhancement of 1,5-diaminopentane production in a recombinant strain of Corynebacterium glutamicum by Tween 40 addition. J Gen Appl Microbiol 62(1):42–45. doi:10.2323/jgam.62.42 CrossRef

25.

Toray (2012). http://www.toray.com/news/rd/nr120213.html. Accessed 10 Sept 2016

26.

Cathay (2012). http://www.cathaybiotech.com/en/products/diamine. Accessed 10 Sept 2016

27.

Kind S, Neubauer S, Becker J, Yamamoto M, Voelkert M, von Abendroth G, Zelder O, Wittmann C (2014) From zero to hero—production of bio-based nylon from renewable resources using engineered Corynebacterium glutamicum. Metab Eng 25:113–123. doi:10.1016/j.ymben.2014.05.007 CrossRef

28.

Demirel E, Durmaz H, Hizal G, Tunca U (2016) A route toward multifunctional polyurethanes using triple click reactions. J Polym Sci Part A Polym Chem 54(4):480–486CrossRef

29.

Choi SH, Kim DH, Raghu AV, Reddy KR, Lee H-I, Yoon KS, Jeong HM, Kim BK (2012) Properties of graphene/waterborne polyurethane nanocomposites cast from colloidal dispersion mixtures. J Macromol Sci Part B 51(1):197–207. doi:10.1080/00222348.2011.583193 CrossRef

30.

Reddy KR, Raghu AV, Jeong HM (2008) Synthesis and characterization of novel polyurethanes based on 4, 4′-{1, 4-phenylenebis [methylylidenenitrilo]} diphenol. Polym Bull 60(5):609–616CrossRef

31.

Reddy KR, Raghu AV, Jeong HM, Siddaramaiah (2009) Synthesis and characterization of pyridine-based polyurethanes. Des Monomers Polym 12(2):109–118CrossRef

32.

Khan MU, Reddy KR, Snguanwongchai T, Haque E, Gomes VG (2016) Polymer brush synthesis on surface modified carbon nanotubes via in situ emulsion polymerization. Colloid Polym Sci 294(10):1599–1610CrossRef

33.

Lee YR, Kim SC, H-i Lee, Jeong HM, Raghu AV, Reddy KR, Kim BK (2011) Graphite oxides as effective fire retardants of epoxy resin. Macromol Res 19(1):66–71CrossRef

34.

Zhang YP, Lee SH, Reddy KR, Gopalan AI, Lee KP (2007) Synthesis and characterization of core-shell SiO2 nanoparticles/poly (3-aminophenylboronic acid) composites. J Appl Polym Sci 104(4):2743–2750CrossRef

35.

Hassan M, Reddy KR, Haque E, Minett AI, Gomes VG (2013) High-yield aqueous phase exfoliation of graphene for facile nanocomposite synthesis via emulsion polymerization. J Colloid Interface Sci 410:43–51CrossRef

36.

Sacchi A, Di Landro L, Pegoraro M, Severini F (2004) Morphology of isotactic polypropylene–polyamide 66 blends and their mechanical properties. Eur Polym J 40(8):1705–1713CrossRef

Title: Bio-based poly(pentamethylene oxamide) synthesized by spray/solid-state polycondensation
Authors: Cong Cheng
Fredrick Nzioka Mutua
Yusheng Dong
Bo Zhu
Yong He
Publication date: 18-04-2017
Publisher: Springer Berlin Heidelberg
Published in: Polymer Bulletin / Issue 1/2018
Print ISSN: 0170-0839
Electronic ISSN: 1436-2449
DOI: https://doi.org/10.1007/s00289-017-2023-1

Springer Professional

Abstract

Please log in to get access to your license.

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Springer Professional "Technik"

Other articles of this Issue 1/2018

Preparation of silver/carbon fiber/polyaniline microwave absorption composite and its application in epoxy resin

Synthesis of waste cooking oil-based polyurethane for solid polymer electrolyte

Comparative studies of thermo-mechanical and morphological properties of polylactic acid/fumed silica/clay (1.28E) and polylactic acid/fumed silica/clay (1.34TCN) nanocomposites

Investigation of mechanical and thermal properties of the cetyltrimethylammonium bromide functionalized molybdenum disulfide (MoS2)/epoxy composites

Modification of epoxy resin by silane-coupling agent to improve tensile properties of viscose fabric composites

Effect of nature of chemical crosslinker on swelling and solubility parameter of a new stimuli-responsive cationic poly(N-acryloyl-N′-propyl piperazine) hydrogel

Premium Partners