Skip to main content
Erschienen in: Polymer Bulletin 4/2012

01.03.2012 | Original Paper

Synthesis and characterization of terminally functionalized and epoxidized hydroxyl-terminated polybutadiene

verfasst von: Mir Mohammad Alavi Nikje, Hassan Hajifatheali

Erschienen in: Polymer Bulletin | Ausgabe 4/2012

Einloggen

Aktivieren Sie unsere intelligente Suche, um passende Fachinhalte oder Patente zu finden.

search-config
loading …

Abstract

Pyridyl N-oxide derivatives of hydroxyl terminated polybutadiene-pyridine (HTPB-PY) were synthesized via functionalization on terminal carbon atoms of HTPB backbone by 2-chloropyridine and epoxidation of C=C bonds and N atoms using in situ generated dimethyl dioxirane (DMD). 1HNMR, 13CNMR, 14NNMR, and FT–IR spectroscopy techniques used in order to investigate the structural elucidation of products. In this synthesis method, HTPB terminal hydroxyl groups have preserved unchanged without applying any conditional controllers.

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

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!

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!

Literatur
1.
Zurück zum Zitat Hadjichristidis N, Pispas S, Pitsikalis M (1999) End-functionalized polymers with zwitterionic end-groups. Prog Polym Sci 24:875–915CrossRef Hadjichristidis N, Pispas S, Pitsikalis M (1999) End-functionalized polymers with zwitterionic end-groups. Prog Polym Sci 24:875–915CrossRef
2.
Zurück zum Zitat Klein J (1996) Shear, friction, and lubrication forces between polymer-bearing surfaces. Annu Rev Mater Sci 26:581–612CrossRef Klein J (1996) Shear, friction, and lubrication forces between polymer-bearing surfaces. Annu Rev Mater Sci 26:581–612CrossRef
3.
Zurück zum Zitat Kassaee MZ, Heydari H, Hattami M, Fazli Nia A (2003) 13C Spin−lattice relaxation times and NOE related studies of hydroxyl-terminated polybutadiene (HTPB). Macromolecules 36:6773–6779CrossRef Kassaee MZ, Heydari H, Hattami M, Fazli Nia A (2003) 13C Spin−lattice relaxation times and NOE related studies of hydroxyl-terminated polybutadiene (HTPB). Macromolecules 36:6773–6779CrossRef
4.
Zurück zum Zitat Ganesh K, Sundarrajan S, Kishore K, Ninan KN, George B, Surianarayanan M (2000) Primary pyrolysis products of hydroxy-terminated polybutadiene. Macromolecules 33:326–330CrossRef Ganesh K, Sundarrajan S, Kishore K, Ninan KN, George B, Surianarayanan M (2000) Primary pyrolysis products of hydroxy-terminated polybutadiene. Macromolecules 33:326–330CrossRef
5.
Zurück zum Zitat Schapman F, Couvercelle JP, Bunel (1998) Low molar mass polybutadiene made cross linkable by silane moieties introduced via addition of thiol to double bond: 3. Synthesis and kinetic study. Polymer 39:4955–4962CrossRef Schapman F, Couvercelle JP, Bunel (1998) Low molar mass polybutadiene made cross linkable by silane moieties introduced via addition of thiol to double bond: 3. Synthesis and kinetic study. Polymer 39:4955–4962CrossRef
6.
Zurück zum Zitat Schapman F, Youssef B, About-Jaudet E, Bunel C (2000) Ignifugation de polyurethanes: I. Utilisation d’un polyol insaturé modifié par le 1-thioéthyl diéthylphosphonate. Eur Polym J 36:1865–1873CrossRef Schapman F, Youssef B, About-Jaudet E, Bunel C (2000) Ignifugation de polyurethanes: I. Utilisation d’un polyol insaturé modifié par le 1-thioéthyl diéthylphosphonate. Eur Polym J 36:1865–1873CrossRef
7.
Zurück zum Zitat Boutevin B, Fleury E, Parisi JP, Pietrasanta Y (1989) Synthèse de composé photoréticulables, modification du polybutadiène carboxytéléchélique par des monomères acryliques. Makromol Chem 190:2363–2372CrossRef Boutevin B, Fleury E, Parisi JP, Pietrasanta Y (1989) Synthèse de composé photoréticulables, modification du polybutadiène carboxytéléchélique par des monomères acryliques. Makromol Chem 190:2363–2372CrossRef
8.
Zurück zum Zitat Poussard L, Burel F, Couvercelle J, Loutelier-Bourhis PC, Bunel C (2006) Synthesis of new anionic HTPB-based polyurethane elastomers: aqueous dispersion and physical properties. J Appl Polym Sci 100:3312–3322CrossRef Poussard L, Burel F, Couvercelle J, Loutelier-Bourhis PC, Bunel C (2006) Synthesis of new anionic HTPB-based polyurethane elastomers: aqueous dispersion and physical properties. J Appl Polym Sci 100:3312–3322CrossRef
9.
Zurück zum Zitat Ameduri B, Boutevin B, Nouiri M (1993) Synthesis and properties of fluorinated telechelic macromolecular diols prepared by radical grafting of fluorinated thiols onto hydroxyl-terminated polybutadienes. J Polym Sci Part A 31:2069–2080CrossRef Ameduri B, Boutevin B, Nouiri M (1993) Synthesis and properties of fluorinated telechelic macromolecular diols prepared by radical grafting of fluorinated thiols onto hydroxyl-terminated polybutadienes. J Polym Sci Part A 31:2069–2080CrossRef
10.
Zurück zum Zitat Boutevin B, Hervaud Y, Nouiri M (1990) Addition de thiols fluores sur les polybutadiennes hydroxytelecheliques par voie photochimique. Eur Polym J 26:877–882CrossRef Boutevin B, Hervaud Y, Nouiri M (1990) Addition de thiols fluores sur les polybutadiennes hydroxytelecheliques par voie photochimique. Eur Polym J 26:877–882CrossRef
11.
Zurück zum Zitat Boutevin B, Hervaud Y, Mouledous G (1998) Grafting phosphonated thiol on hydroxy telechelic polybutadiene. Polym Bull 41:145–151CrossRef Boutevin B, Hervaud Y, Mouledous G (1998) Grafting phosphonated thiol on hydroxy telechelic polybutadiene. Polym Bull 41:145–151CrossRef
12.
Zurück zum Zitat El Khatib W, Youssef B, Bunel C, Mortaigne B (2003) Fireproofing of polyurethane elastomers by reactive organophosphonates. Polym Int 52:146–152CrossRef El Khatib W, Youssef B, Bunel C, Mortaigne B (2003) Fireproofing of polyurethane elastomers by reactive organophosphonates. Polym Int 52:146–152CrossRef
13.
Zurück zum Zitat Lotti L, Coiai S, Ciardelli F, Galimberti M, Passaglia E (2009) Thiol-ene radical addition of l-cysteine derivatives to low molecular weight polybutadiene. Macromol Chem Physic 210:1471–1483CrossRef Lotti L, Coiai S, Ciardelli F, Galimberti M, Passaglia E (2009) Thiol-ene radical addition of l-cysteine derivatives to low molecular weight polybutadiene. Macromol Chem Physic 210:1471–1483CrossRef
14.
Zurück zum Zitat Yang JM, Lai WC, Lin HT (2001) Properties of HTPB-based polyurethane membrane prepared by epoxidation method. J Membrane Sci 183:37–47CrossRef Yang JM, Lai WC, Lin HT (2001) Properties of HTPB-based polyurethane membrane prepared by epoxidation method. J Membrane Sci 183:37–47CrossRef
15.
Zurück zum Zitat Yang JM, Yang SJ, Lin HT, Chen JK (2007) Modification of HTPB-based polyurethane with temperature-sensitive poly (N-isopropyl acrylamide) for biomaterial usage. J Biomed Mater Res B 80:43–51 Yang JM, Yang SJ, Lin HT, Chen JK (2007) Modification of HTPB-based polyurethane with temperature-sensitive poly (N-isopropyl acrylamide) for biomaterial usage. J Biomed Mater Res B 80:43–51
16.
Zurück zum Zitat Bai Y, Qian J, Yin J, Zhai Z, Yang Y (2007) HTPB-based polyurethane urea membranes for recovery of aroma compounds from aqueous solution by pervaporation. J Appl Polym Sci 104:552–559CrossRef Bai Y, Qian J, Yin J, Zhai Z, Yang Y (2007) HTPB-based polyurethane urea membranes for recovery of aroma compounds from aqueous solution by pervaporation. J Appl Polym Sci 104:552–559CrossRef
17.
Zurück zum Zitat Schapman F, Couvercelle JP, Bunel C (2002) Low molar mass polybutadiene made cross linkable by the introduction of styrenic moieties via urethane linkage: synthesis, kinetic and crosslinking studies. Eur Polym J 38:1979–1986CrossRef Schapman F, Couvercelle JP, Bunel C (2002) Low molar mass polybutadiene made cross linkable by the introduction of styrenic moieties via urethane linkage: synthesis, kinetic and crosslinking studies. Eur Polym J 38:1979–1986CrossRef
18.
Zurück zum Zitat Matmour R, Joncheray TJ, Gnanou Y, Duran RS (2007) Cross-linking of polybutadiene at the air/water interface: toward an easy access to two-dimensional polymeric materials. J Colloid Interf Sci 311:315–321CrossRef Matmour R, Joncheray TJ, Gnanou Y, Duran RS (2007) Cross-linking of polybutadiene at the air/water interface: toward an easy access to two-dimensional polymeric materials. J Colloid Interf Sci 311:315–321CrossRef
19.
Zurück zum Zitat Hwang J, Foster MD, Quirk RP (2004) Synthesis of 4-,8-,12-arm star-branched polybutadienes with three different chain-end functionalities using a functionalized initiator. Polymer 45:873–880CrossRef Hwang J, Foster MD, Quirk RP (2004) Synthesis of 4-,8-,12-arm star-branched polybutadienes with three different chain-end functionalities using a functionalized initiator. Polymer 45:873–880CrossRef
20.
Zurück zum Zitat Shankar RM, Roy TK, Jana T (2009) Terminal functionalized hydroxyl-terminated polybutadiene: an energetic binder for propellant. J Appl Polym Sci 114:732–741CrossRef Shankar RM, Roy TK, Jana T (2009) Terminal functionalized hydroxyl-terminated polybutadiene: an energetic binder for propellant. J Appl Polym Sci 114:732–741CrossRef
21.
Zurück zum Zitat Youssif S (2001) Recent trends in the chemistry of pyridine N-oxides. Aarkivoc. 1:242–268 Youssif S (2001) Recent trends in the chemistry of pyridine N-oxides. Aarkivoc. 1:242–268
22.
Zurück zum Zitat Oconnor CJ, Sinn E, Carlin RL (1977) Structural and magnetic properties of [M (C5H5NO) 6] L2 (M = copper, zinc; L = perchlorate (1-), tetrafluoroborate (1-)). Inorg Chem 16:3314–3320CrossRef Oconnor CJ, Sinn E, Carlin RL (1977) Structural and magnetic properties of [M (C5H5NO) 6] L2 (M = copper, zinc; L = perchlorate (1-), tetrafluoroborate (1-)). Inorg Chem 16:3314–3320CrossRef
23.
Zurück zum Zitat Soscu′na H, Castellanoa O, Bermu′deza Y, Toro-Mendozaa C, Marcanob A, Alvarado Y (2002) Linear and nonlinear optical properties of pyridine N-oxide molecule. J Mol Struc Theochem 592:19–28CrossRef Soscu′na H, Castellanoa O, Bermu′deza Y, Toro-Mendozaa C, Marcanob A, Alvarado Y (2002) Linear and nonlinear optical properties of pyridine N-oxide molecule. J Mol Struc Theochem 592:19–28CrossRef
24.
Zurück zum Zitat Zhao YH, Su ZM, Wang Y, Fu YM, Liu SD, Li P (2007) Two novel lead-carboxylate complexes based on nicotinic acid N-oxide: synthesis, crystal structures and luminescent properties. Inorg Chem Commun 10:410–414CrossRef Zhao YH, Su ZM, Wang Y, Fu YM, Liu SD, Li P (2007) Two novel lead-carboxylate complexes based on nicotinic acid N-oxide: synthesis, crystal structures and luminescent properties. Inorg Chem Commun 10:410–414CrossRef
25.
Zurück zum Zitat Alavi Nikje MM, Hajifatheali H (2011) Nanoclay-mediated epoxidation of HTPB using in situ generated dimethyl dioxirane. Des Monomers Polym 14:155–165CrossRef Alavi Nikje MM, Hajifatheali H (2011) Nanoclay-mediated epoxidation of HTPB using in situ generated dimethyl dioxirane. Des Monomers Polym 14:155–165CrossRef
26.
Zurück zum Zitat Akcelrud L, Aguiar M, Menezes SCD (1994) Configurational double bond selectivity in the epoxidation of hydroxy-terminated polybutadiene with m-chloroperbenzoic acid. Macromol Chem Physic 195:3937–3948CrossRef Akcelrud L, Aguiar M, Menezes SCD (1994) Configurational double bond selectivity in the epoxidation of hydroxy-terminated polybutadiene with m-chloroperbenzoic acid. Macromol Chem Physic 195:3937–3948CrossRef
27.
Zurück zum Zitat Zuchowska D (1980) Polybutadiene modified by epoxidation. 1. Effect of polybutadiene microstructure on the reactivity of double bonds. Polymer 21:514–520CrossRef Zuchowska D (1980) Polybutadiene modified by epoxidation. 1. Effect of polybutadiene microstructure on the reactivity of double bonds. Polymer 21:514–520CrossRef
28.
Zurück zum Zitat Gemmer RV, Golub MA (1978) 13C NMR spectroscopic study of epoxidized 1,4-polyisoprene and 1,4-polybutadiene. J Polym Sci 16:2985–2990 Gemmer RV, Golub MA (1978) 13C NMR spectroscopic study of epoxidized 1,4-polyisoprene and 1,4-polybutadiene. J Polym Sci 16:2985–2990
29.
Zurück zum Zitat Kanakavel M (1987) Characterization of hydroxy-terminated polybutadienes by 13C NMR. Makromol Chem 188:845–854CrossRef Kanakavel M (1987) Characterization of hydroxy-terminated polybutadienes by 13C NMR. Makromol Chem 188:845–854CrossRef
30.
Zurück zum Zitat Subramanian K (1999) Hydroxyl-terminated poly (azidomethyl ethylene oxide-b-butadiene-b-azidomethyl ethylene oxide)-synthesis, characterization and its potential as a propellant binder. Eur Polym J 35:1403–1411CrossRef Subramanian K (1999) Hydroxyl-terminated poly (azidomethyl ethylene oxide-b-butadiene-b-azidomethyl ethylene oxide)-synthesis, characterization and its potential as a propellant binder. Eur Polym J 35:1403–1411CrossRef
31.
Zurück zum Zitat Alavi Nikje MM, Mozaffari Z (2007) Chemoselective epoxidation of hydroxyl-terminated polybutadiene (HTPB) using in situ generated dimethyl dioxirane (DMD). Des Monomers Polym 10:67–77CrossRef Alavi Nikje MM, Mozaffari Z (2007) Chemoselective epoxidation of hydroxyl-terminated polybutadiene (HTPB) using in situ generated dimethyl dioxirane (DMD). Des Monomers Polym 10:67–77CrossRef
32.
Zurück zum Zitat Nazare AN, Deuskar VD, Asthana SN, Shrotri PG (1993) Influence of characteristics of HTPB on mechanical properties and ballistic behavior of composite propellant. J Polym mater 10:213–215 Nazare AN, Deuskar VD, Asthana SN, Shrotri PG (1993) Influence of characteristics of HTPB on mechanical properties and ballistic behavior of composite propellant. J Polym mater 10:213–215
33.
Zurück zum Zitat Baran P, Boč R, Breza M, Elias H, Fuess H, Jorı′k V, Klement R, Svoboda I (2002) The spectroscopic and structural properties of copper (II) complexes of the novel tridentate (ONO) pyridine N-oxide ligand Hpoxap. Polyhedron 21:1561–1571CrossRef Baran P, Boč R, Breza M, Elias H, Fuess H, Jorı′k V, Klement R, Svoboda I (2002) The spectroscopic and structural properties of copper (II) complexes of the novel tridentate (ONO) pyridine N-oxide ligand Hpoxap. Polyhedron 21:1561–1571CrossRef
Metadaten
Titel
Synthesis and characterization of terminally functionalized and epoxidized hydroxyl-terminated polybutadiene
verfasst von
Mir Mohammad Alavi Nikje
Hassan Hajifatheali
Publikationsdatum
01.03.2012
Verlag
Springer-Verlag
Erschienen in
Polymer Bulletin / Ausgabe 4/2012
Print ISSN: 0170-0839
Elektronische ISSN: 1436-2449
DOI
https://doi.org/10.1007/s00289-011-0592-y

Weitere Artikel der Ausgabe 4/2012

Polymer Bulletin 4/2012 Zur Ausgabe

    Marktübersichten

    Die im Laufe eines Jahres in der „adhäsion“ veröffentlichten Marktübersichten helfen Anwendern verschiedenster Branchen, sich einen gezielten Überblick über Lieferantenangebote zu verschaffen.