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Licensed Unlicensed Requires Authentication Published by De Gruyter May 5, 2015

Synthesis and Properties of Nitrogen Heterocycle-Functionalized Core-Shell Hyperbranched Polyester

  • S. Karpagam and S. Guhanathan

Abstract

Core-shell hyperbranched polyesters (HBPE) of third generation prepared from 2,2′-bis (hydroxymethyl) propionic acid (Bis-MPA) as an ABx monomer and N-heterocyclic (indole, piperidine and piperazine) phosphoryl dichloride as a core molecule by melt condensation process. These polymers were characterized by FT-IR, 1H NMR, 13C NMR, 31P NMR, elemental analysis, and MALDI spectroscopy. The thermal behavior of the polymers has been investigated by thermo gravimetric analysis (TGA) and differential scanning calorimetry (DSC). There is no weight loss observed until 250 °C under nitrogen atmosphere. DSC showed that the glass transition temperatures was about −14 and −30 °C for the prepared core-shell HBPE. The dielectric properties such as dielectric constant and loss factor for these polyesters were also studied with respect to change of frequency (50 Hz to 5 MHz).


* Mail address: Subramanian Karpagam, Organic Chemistry Division, School of Advanced Sciences, VIT University, Vellore – 14, Tamil Nadu, India, E-mail:

References

AkramM., JavedA. and RizviT. Z., “Dielectric Properties of Industrial Polymer Composite Materials”, Turk. J. Phys., 29, 355–362 (2005)Search in Google Scholar

ArehutA., VogtleF., “Functional Cascade Molecules”, Chem. Soc. Rev., 27, 233–240 (1998) 10.1039/a827233zSearch in Google Scholar

AstrueD., ChardaeF., “Dendritic Catalysts and Dendrimers in Catalysis”, Chem. Rev., 101, 2991–3024 (2001) 10.1021/cr010323tSearch in Google Scholar

BeyerleinD., BelgeG., EichhornK. J., GauglitG., GrundkeK. and VoitB., “Preparation and Properties of Thin Films of Hyperbranched Polyesters with Different End Groups”, Macromol. Symp., 164, 117–132 (2001) 10.1002/1521-3900(200102)164:1<117::AID-MASY117>3.0.CO;2-5Search in Google Scholar

BrennerA. R., VoitB. I., MassaD. J. and TurnerS. R, “Hyperbranched Polyesters: End Group Modification and Properties”, Macromol. Symp., 102, 47–54 (1996) 10.1002/masy.19961020108Search in Google Scholar

BuhleierE., WehnerW. and VogtleF., ”Cascade and Nonskid-Chain-Like Syntheses of Moleculr Cavity Topologies”, Synthesis, 2, 155–158 (1978) 10.1055/s-1978-24702Search in Google Scholar

ConnelJ. W., SmithJ. G.Jr. and HergenrotherP. M., “Oxygen Plasma-Resistant Phenylphosphine-Oxide Containing Polyimides and Poly(arylene ether hetercycle)s”, Polymer, 36, 5–11 (1995) 10.1016/0032-3861(95)90668-RSearch in Google Scholar

CzechP., OkrasaL., BoiteuxG., MechinF. and UlanskiJ., “Polyurethane Networks Based on Hybranched Polyesters: Synthesis and Molecular Relaxations”, J. Non-Cryst. Solids., 351, 2735–2741 (2005) 10.1016/j.jnoncrysol.2005.05.038Search in Google Scholar

DengJ., ZhuS. and ShiW., “Effect of Molecular Chain Structure of the Cured Epoxy Resin Containing Hyperbranched (3-hydroxyphenyl) Phosphate on Expansion and Flame RetardanceJ. Appl. Polym. Sci., 94, 2065–2070 (2004) 10.1002/app.21152Search in Google Scholar

FischerM., VogtleF., “Dendrimers: From Design to Application-A Progress Report”, Angew. Chem. Int. Ed., 38, 884–905 (1999) 10.1002/(SICI)1521-3773(19990401)38:7<884::AID-ANIE884>3.0.CO;2-KSearch in Google Scholar

GoswamiA., VarmaR. R., “Dielectric Behaviour of Dysprosium Oxide Films”, Thin Solid Films, 28, 157–165 (1975) 10.1016/0040-6090(75)90106-6Search in Google Scholar

GoswamiA., SinghA. K., “Hyperbranched Polyester Having Nitrogen Core: Synthesis and Application as Metal Ion Extractant”, React. Funct. Polym., 61, 255–263 (2004) 10.1016/j.reactfunctpolym.2004.06.006Search in Google Scholar

GraysonA. M., FrechetJ. M., “Convergent Dendrons and Dendrimers from Synthesis to Application”, Chem. Rev., 101, 3819–3868 (2001) 10.1021/cr990116hSearch in Google Scholar PubMed

HanselmannR., HolterD. and FreyH., “Hyperbranched Polymers Prepared via the Core-Dilution/Slow Addition Technique: Computer Simulation of Molecular Weight Distribution and Degree of Branching”, Macromolecules31, 3790–3801 (1998) 10.1021/ma971197rSearch in Google Scholar

HashimotoS., FurukawaI. and UeyamaK., “Synthesis of Properties of Phosphorus-Containing Aromatic Polyethers”, J. Macromol. Sci. Chem., A, 11, 2167–2176 (1977)10.1080/00222337708061356Search in Google Scholar

HawkerC. J., LeeR. and FrechetJ. M. J., “One-Step Synthesis of Hyperbranched Dendritic Polyesters”, J. Am. Chem. Soc., 113, 4583–4588 (1991) 10.1021/ja00012a030Search in Google Scholar

HuX.-P., LiY.-L. and WangY. Z., “Synergistic Effect of the Charring Agent on the Thermal and Flame Retardant Properties of Polyethylene”, Macromol. Mater. Eng., 289, 208–212 (2004) 10.1002/mame.200300189Search in Google Scholar

HultA., JohanssonV. and MalmstromE., “Hyperbranched Polymers”, Adv. Polym. Sci., 143, 1–34 (1999) 10.1007/3-540-49780-3_1Search in Google Scholar

HippelA. V., GrossV., JelatisJ. G. and GellerM., “Photocurrent, Space-Charge Built-Up, and Field Emission in Alkali Halide Crystals”, Phys. Rev., 91, 568–578 (1953) 10.1103/PhysRev.91.568Search in Google Scholar

JikeiM., MoriR., KawauchiS., KakimotoM. and TaniguchiY., “Synthesis and Properties of Hyperbranched Poly(triphenylamine)s Prepared by Palladium Catalyzed C-N Coupling Reaction”, Polym. J., 34, 550–557 (2002) 10.1295/polymj.34.550Search in Google Scholar

KarpagamS., ThangarajR. and GuhanathanS., “Functional Modification of Poly(vinyl alcohol) through Phosphorus Containing Nitrogen Heterocyclic Moieties”, J. Appl. Polym. Sci., 110, 2549–2554 (2008) 10.1002/app.28629Search in Google Scholar

KimuraT., KajiwaraM., “The Synthesis of Phosphinylphosphorimidic Hydroxyethyl Acrylate and the Electrical Properties of its Polymer Produced by Ultra Violet-Irradiation-Induced Polymerization”, Polymer, 36, 713–718 (1995) 10.1016/0032-3861(95)93099-8Search in Google Scholar

van KrevelenD. W., “Some Basic Aspects of Flame Resistance of Polymeric MaterialsPolymer, 16, 615–620 (1975) 10.1016/0032-3861(75)90157-3Search in Google Scholar

LiangS., NeisiusN. M. and GaanS., “Recent Developments in Flame Retardant Polymer Coatings”, Prog. Org. Coat., 76, 1642–1665 (2013) 10.1016/j.porgcoat.2013.07.014Search in Google Scholar

MalmstromE., LiuF., BoydR. H., HultA. and GeddeU. W., “Relaxation Processes in Hyperbranched Polyesters”, Polym. Bull., 32, 679–685 (1994) 10.1007/BF00973919Search in Google Scholar

NewkomeG. R., YaoZ., BakerG. R. and GuptaV. K.Micelles. Part 1. Cascade Molecules: A New Approach to Micelles. A [27]- Arborol”, J. Org. Chem., 50, 2003–2004 (1985) 10.1021/jo00211a052Search in Google Scholar

RadkeW., LitvinenkoG. and MullerA. H. E., “Effect of Core- Forming Molecules on Molecular Weight Distribution and Degree of Branching in the Synthesis of Hyperbranched Polymers”, Macromolecules, 31, 239–248 (1998) 10.1021/ma970952ySearch in Google Scholar

ScherrenbergR., CoussensB., van VlietP., EdouardG., BrackmanJ.de BrabanderE., “The Molecular Characteristics of Poly(propyleneimine) Dendrimers as Studied with Small-Angle Neutron Acattering, Viscosimetry and Molecular Dynamics”, Macromolecules, 31, 456–461 (1998) 10.1021/ma9618181Search in Google Scholar

SibdasS. M., NiranjanK., “S-Triazine Containing Flame Retardant Hyperbranched Polyamines: Synthesis, Characterization and Properties Evaluation”, Polym. Degrad. Stab., 92, 947–955 (2007) 10.1016/j.polymdegradstab.2007.03.012Search in Google Scholar

SmythC. P.: Dielectric Behavior and Structure”, Mcgraw Hill, New York (1955)Search in Google Scholar

ThomassonD., BoissonF., ReydetE. G. and MechinF., “Hydroxylated Hyperbranched Polyesters as Crosslinking Agents for Polyurethane Networks: Partial Modification of the OH Chain Ends“, React. Funct. Polym., 66, 1462–1481 (2006) 10.1016/j.reactfunctpolym.2006.04.012Search in Google Scholar

TomaliaD. A., BakerH., DewaldJ., HallM., MartinS., RoeckJ., RyderJ. and SmithP., “A New Class of Polymers: Starburst-Dendritic Macromolecules”, Polym. J., 17, 117–132 (1985) 10.1295/polymj.17.117Search in Google Scholar

TomaliaD. A., Barker.H., DewaldJ., HallM., MartinS., RoeckJ., RyderJ. and SmithP., “Dendritic Macromolecules: Synthesis of Starburst Dendrimers”, Macromolecules, 19, 2466–2468 (1986) 10.1021/ma00163a029Search in Google Scholar

TomutaA., FerrandoF., SerraA. and RamisX., “New Aromatic-Aliphatic Hyperbranched Polyesters with Vinylic End Groups of Different Length as Modifiers of Epoxy/Anhydride Thermosets”, React. Funct. Polym., 72, 556–563 (2012) 10.1016/j.reactfunctpolym.2012.05.008Search in Google Scholar

TurnerS. R., VoitB. I. and MoureyT. H., “All-Aromatic Hyperbranched Polyesters with Phenol and Acetate and Group: Synthesis and Characterization”, Macromolecules, 26, 4617–4623 (1993) 10.1021/ma00069a031Search in Google Scholar

TurnerS. R., WalterF., VoitB. I. and MoureyT. H., “Hyperbranched Aromatic Polyester with Carboxylic Acid Terminal Groups”, Macromolecules, 27, 1611–1616 (1994) 10.1021/ma00084a051Search in Google Scholar

VoitB., “New Developments in Hyperbranched Polymers”, J. Polym. Sci. Part A, 38, 2505–2525 (2000) 10.1002/1099-0518(20000715)38:14<2505::AID-POLA10>3.0.CO;2-8Search in Google Scholar

ViswanathG. R., GuhanathanS., “Synthesis and Characterization of Nitrogen Containing Hyperbranched Aliphatic Polyesters”, Bulletin of Pure and Applied Sciences, 26C, 71–83 (2007)Search in Google Scholar

WooleyK. L., HawkerC. J., LeeR. and FrechetJ. M. J., “One-Step Synthesis of Hyperbranched Polyesters. Molecular Weight Control and Chain End Functionalization”, Polym. J., 26, 187–197 (1994) 10.1295/polymj.26.187Search in Google Scholar

YasuhikoH., TakayukiS., “Heterocyclic Compounds such as Pyrrole, Pyridine, Pyrrolidine, Piperidine, Indole, Imidazol and Pyrazines”, Appl. Catal. A, 260, 251–259 (2004) 10.1016/S0926-860X(03)00197-2Search in Google Scholar

ZagarE., ZigonM., “Aliphatic Hyperbranched Polyesters Based on 2,2-Bis(methylol)Propionic Acid –Determination of Structure, Solution and Bulk Properties”, Prog. Polym. Sci., 36, 53–88 (2011) 10.1016/j.progpolymsci.2010.08.004Search in Google Scholar

Received: 2014-07-08
Accepted: 2015-01-21
Published Online: 2015-05-05
Published in Print: 2015-05-29

© 2015, Carl Hanser Verlag, Munich

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