Synthesis and characterization of sustainable polyurethane based on epoxy soybean oil and modified by double-decker silsesquioxane
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  • 作者:Jie Huang ; Pingping Jiang ; Xiaoting Li ; Yuandan Huang
  • 刊名:Journal of Materials Science
  • 出版年:2016
  • 出版时间:March 2016
  • 年:2016
  • 卷:51
  • 期:5
  • 页码:2443-2452
  • 全文大小:1,039 KB
  • 参考文献:1.Shouming W, Hayakawa T, Kakimoto M-a, Oikawa H (2008) Synthesis and characterization of organosoluble aromatic polyimides containing POSS in main chain derived from double-decker-shaped silsesquioxane. Macromolecules 41:3481–3487CrossRef
    2.Kuoa SW, Changb FC (2011) POSS related polymer nanocomposites. Prog Polym Sci 36:1649–1696CrossRef
    3.Tamaki R, Tanaka Y, Asuncion MZ, Choi J, Laine RM (2001) Octa(aminophenyl)silsesquioxane as a nanoconstruction Site. J Am Chem Soc 123:12416–12417CrossRef
    4.Ak M, Gacal B, Kiskan B, Yagci Y, Toppare L (2008) Enhancing electrochromic properties of polypyrrole by silsesquioxane nanocages. Polymer 49:2202–2210CrossRef
    5.Neumann D, Fisher M, Tran L, Matisons JG (2002) Synthesis and characterization of an isocyanate functionalized polyhedra oligosilsesquioxane and the subsequent formation of an organic-inorganic hybrid polyurethane. J Am Chem Soc 124:13998–13999CrossRef
    6.Laine RM, Roll MF (2011) Polyhedral phenylsilsesquioxanes. Macromolecules 44:1073–1109CrossRef
    7.Cai H, Kai X, Liu X, Fua Z, Chen M (2012) A facile synthesis of octa(carboxyphenyl)silsesquioxane. Dalton Trans 41:6919–6921CrossRef
    8.Hongyao X, Yang B, Wang J, Guang S, Li C (2007) Preparation, Tg improvement, and thermal stability enhancement mechanism of soluble poly(methyl methacrylate) nanocomposites by incorporating octavinyl polyhedral oligomeric silsesquioxanes. J Polym Sci Pol Chem 45:5308–5317CrossRef
    9.Gnanasekaran D, Ajit Walter P, Reddy BSR (2013) Influence of moieties on morphology, thermal, and dielectric properties in polyamide-polyhedral oligomeric silsequioxanes nanocomposites. Polym Eng Sci 53:1637–1644CrossRef
    10.Kun W, Kandola BK, Kandare E, Yuan H (2011) Flame retardant effect of polyhedral oligomeric silsesquioxane and triglycidyl isocyanurate on glass fibre-reinforced epoxy composites. Polym Compos 32:378–389CrossRef
    11.Wei K, Wang L, Zheng S (2013) Organic–inorganic polyurethanes with 3, 13-dihydroxypropyloctaphenyl double-decker silsesquioxane chain extender. Polym Chem 4:1491–1501CrossRef
    12.Bourbigot S, Turf T, Bellayer S, Duquesne S (2009) Polyhedral oligomeric silsesquioxane as flame retardant for thermoplastic polyurethane. Polym Degrad Stab 94:1230–1237CrossRef
    13.Musto P, Abbate M, Pannico M, Scarinzi G, Ragosta G (2012) Improving the photo-oxidative stability of epoxy resins by use of functional POSS additives: a spectroscopic, mechanical and morphological study. Polymer 53:5016–5036CrossRef
    14.Leu CM, Te Chang Y, Wei KH (2003) Polyimide-side-chain tethered polyhedral oligomeric silsesquioxane nanocomposites for low-dielectric film applications. Chem Mater 15:3721–3727CrossRef
    15.Wahab MA, Mya KY, He C (2008) Synthesis, morphology, and properties of hydroxyl terminated-POSS/Polyimide low-k nanocomposite films. J Polym Sci Pol Chem 46:5887–5896CrossRef
    16.Ye Y, Yen Y, Chen W, Cheng C, Chang F (2008) A simple approach toward low-dielectric polyimide nanocomposites: blending the polyimide precursor with a fluorinated polyhedral oligomeric silsesquioxane. J Polym Sci Pol Chem 46:6296–6304CrossRef
    17.Wang J, Ye Z, Joly H (2007) Synthesis and characterization of hyperbranched polyethylenes tethered with polyhedral oligomeric silsesquioxane (POSS) nanoparticles by chain walking ethylene copolymerization with acryloisobutyl-POSS. Macromolecules 40:6150–6163CrossRef
    18.Lee KM, Knight PT, Chung T, Mather PT (2008) Polycaprolactone-POSS chemical/physical double networks. Macromolecules 41:4730–4738CrossRef
    19.Frank KL, Exley SE, Thornell TL, Morgan SE, Wiggins JS (2012) Investigation of pre-reaction and cure temperature on multiscale dispersion in POSS/epoxy nanocomposites. Polymer 53:4643–4651CrossRef
    20.Tan BH, Hussain H, Leong YW, Lin TT, Tjiua WW, He C (2013) Tuning self-assembly of hybrid PLA-P(MA-POSS) block copolymers in solution via stereocomplexation. Polym Chem 4:1250–1259CrossRef
    21.Wang Z, Leng S, Wang Z, Li G, Hao Yu (2011) Nanostructured organic-inorganic copolymer networks based on polymethacrylate-functionalized octaphenylsilsesquioxane and methyl methacrylate: synthesis and characterization. Macromolecules 44:566–574CrossRef
    22.Huang J, Xiao Y, My KY, Liu X, He C, Dai J, Siow YP (2004) Thermomechanical properties of polyimide-epoxy nanocomposites from cubic silsesquioxane epoxides. J Mater Chem 14:2858–2863CrossRef
    23.Markovic E, Clarke S, Matisons J, Simon GP (2008) Synthesis of POSS-methyl methacrylate-based cross-linked hybrid materials. Macromolecules 41:1685–1692CrossRef
    24.Cardoen G, Coughlin EB (2004) Hemi-telechelic polystyrene-POSS copolymers as model systems for the study of well-defined inorganic/organic hybrid materials. Macromolecules 37:5123–5126CrossRef
    25.Kotal A, Si S, Paira TK, Mandal TK (2008) Synthesis of semitelechelic POSS-Polymethacrylate hybrids by thiol-mediated controlled radical polymerization with unusual thermal behaviors. J Polym Sci Pol Chem 46:1111–1123CrossRef
    26.Mather PT, Jeon HG, Romo-Uribe A (1999) Mechanical relaxation and microstructure of poly(norbornyl-POSS) copolymers. Macromolecules 32:1194–1203CrossRef
    27.Waddon AJ, Zheng L, Farris RJ, Bryan Coughlin E (2002) Nanostructured polyethylene-POSS copolymers: control of crystallization and aggregation. Nano Lett 10:1149–1155CrossRef
    28.Fina A, Tabuani D, Frache A, Camino G (2005) Polypropylene–polyhedral oligomeric silsesquioxanes (POSS) nanocomposites. Polymer 46:7855–7866CrossRef
    29.Li X, Xiaolong L (2007) Effect of annealing on the structure and properties of polyvinylidene fluoride hollow fiber by melt-spinning. J Appl Polym Sci 103:935–941CrossRef
    30.Goseki R, Hirai T, Ishida Y, Kakimoto M-a, Hayakawa T (2012) Rapid and reversible morphology control in thin films of poly(ethylene oxide)-block-POSS-containing poly(methacrylate). Polym J 44:658–664CrossRef
    31.Ni C, Ni G, Zhang L, Mi J, Yao B, Zhu C (2011) Syntheses of silsesquioxane (POSS)-based inorganic/organic hybrid and the application in reinforcement for an epoxy resin. J Colloid Interface Sci 362:94–99CrossRef
    32.Ni Y, Zheng S (2007) Nanostructured thermosets from epoxy resin and an organic-inorganic amphiphile. Macromolecules 40:7009–7018CrossRef
    33.Baldi F, Bignotti F, Ricco L, Monticelli O, Ricco T (2006) Mechanical and structural characterization of POSS modified polyamide. J Appl Polym Sci 100:3409–3414CrossRef
    34.Ding Y, Chen G, Song J, Gou Y, Shi J, Jin R, Li Q (2012) Properties and morphology of supertoughened polyamide 6 hybrid composites. J Appl Polym Sci 126:194–204CrossRef
    35.Madbouly SA, Otaigbe JU, Nanda AK, Wicks DA (2007) Rheological behavior of POSS/polyurethane-urea nanocomposite films prepared by homogeneous solution polymerization in aqueous dispersions. Macromolecules 40:4982–4991CrossRef
    36.Raftopoulos KN, Janowski B, Apekis L, Pissis P, Pielichowski K (2013) Direct and indirect effects of POSS on the molecular mobility of polyurethanes with varying segment Mw. Polymer 54:2745–2754CrossRef
    37.Chen Y, Kang E-T (2004) New approach to nanocomposites of polyimides containing polyhedral oligomeric silsesquioxane for dielectric applications. Mater Lett 58:3716–3719CrossRef
    38.Wright ME, Petteys BJ, Guenthner AJ, Fallis S, Yandek GR, Tomczak SJ, Minton TK, Brunsvold A (2006) Chemical modification of fluorinated polyimides: new thermally curing hybrid polymers with POSS. Macromolecules 39:4710–4718CrossRef
    39.Lee Y-J, Kuo S-W, Huang W-J, Lee H-Y, Chang F-C (2004) Miscibility, specific interactions, and self-assembly behavior of phenolic/polyhedral oligomeric silsesquioxane hybrids. J Polym Sci Polym Phys 42:1127–1136CrossRef
    40.Markovic E, Nguyen K, Clarke S, Constantopoulos K, Matisons J, Simon GP (2013) Synthesis of POSS-Polyurethane hybrids using octakis(m-isoprenyl-α,α’dimethylbenzylisocyanato dimethylsiloxy) octasilsesquioxane (Q8M8™I) as a crosslinking agent. J Polym Sci Pol Chem 51:5038–5045CrossRef
    41.Huitron-Rattinger E, Ishida K, Romo-Uribe A, Mather PT (2013) Thermally modulated nanostructure of poly(ε-caprolactone)-POSS multiblock thermoplastic polyurethanes. Polymer 54:3350–3362CrossRef
    42.Turri S, Levi M (2005) Structure, dynamic properties, and surface behavior of nanostructured ionomeric polyurethanes from reactive polyhedral oligomeric silsesquioxanes. Macromolecules 38:5569–5574CrossRef
    43.Knight PT, Lee KM, Qin H, Mather PT (2008) Biodegradable thermoplastic polyurethanes incorporating polyhedral oligosilsesquioxane. Biomacromolecules 9:2458–2467CrossRef
    44.Janowski B, Pielichowski K (2008) Thermo(oxidative) stability of novel polyurethane/POSS nanohybrid elastomers. Thermochim Acta 478:51–53CrossRef
    45.Seino M, Hayakawa T, Ishida Y, Kakimoto M-a (2006) Hydrosilylation polymerization of double-decker-shaped silsesquioxane having hydrosilane with diynes. Macromolecules 39:3473–3475CrossRef
    46.Petrović ZS (2008) Polyurethanes from vegetable oils. Polym Rev 48:109–155CrossRef
    47.Liu H, Zheng S (2005) Polyurethane networks nanoreinforced by polyhedral oligomeric silsesquioxane. Macromol Rapid Commun 26:196–200CrossRef
    48.Wang W, Guo Y-l, Otaigbe JU (2009) The synthesis, characterization and biocompatibility of poly(ester urethane)/polyhedral oligomeric silesquioxane nanocomposites. Polym 50:5749–5757CrossRef
    49.Morent R, De Geyter N, Van Vlierberghe S, Beaurain A, Dubruel P, Payen E (2011) Influence of operating parameters on plasma polymerization of acrylic acid in a mesh-to-plate dielectric barrier discharge. Prog Org Coat 70:336–341CrossRef
    50.Ruijun G, Konar S, Sain M (2012) Preparation and characterization of sustainable polyurethane foams from soybean oils. J Am Oil Chem Soc 89:2103–2111CrossRef
    51.Bandyopadhyay-Ghosh S, Ghosh SB, Sain M (2010) Synthesis of soy-polyol by two step continuous route and development of soy-based polyurethane foam. J Polym Environ 18:437–442CrossRef
    52.Vaia RA, Maguire JF (2007) Polymer Nanocomposites with prescribed morphology: going beyond nanoparticle-filled polymers. Chem Mater 19:2736–2751CrossRef
    53.Sanchez C, Julián B, Belleville P, Popall M (2005) Applications of hybrid organic-inorganic nanocomposites. J Mater Chem 15:3559–3592CrossRef
    54.Strachota A, Kroutilová I, Kovárová J, Matějka L (2004) Epoxy networks reinforced with polyhedral oligomeric silsesquioxanes (POSS). Thermomechanical properties. Macromolecules 37:9457–9464CrossRef
    55.Liu Y, Ni Y, Zheng S (2006) Polyurethane networks modified with octa(propylglycidyl ether) polyhedral oligomeric silsesquioxane. Macromol Chem Phys 207:1842–1851CrossRef
  • 作者单位:Jie Huang (1)
    Pingping Jiang (1)
    Xiaoting Li (1)
    Yuandan Huang (1)

    1. The Key Laboratory of Food Colloids and Biotechnology, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi, 214122, China
  • 刊物类别:Chemistry and Materials Science
  • 刊物主题:Chemistry
    Materials Science
    Characterization and Evaluation Materials
    Polymer Sciences
    Continuum Mechanics and Mechanics of Materials
    Crystallography
    Mechanics
  • 出版者:Springer Netherlands
  • ISSN:1573-4803
文摘
A series of environmentally friendly and sustainable polyurethanes using epoxy soybean oil as feedstock were synthesized with the introduction of double-decker silsesquioxane. Feature is that through the two-step polymerization, double-decker octaphenylsilsesquioxanetetraol was added to partially replace 1,4-butanediol acting as chain extender, and petroleum-based polyol was effectively replaced for polyurethane synthesis. On top of that, POSS tetraol was prepared and characterized by 1H NMR and MALDI-TOF MS. As for the organic–inorganic hybrid nanocomposites, their structures and properties were investigated by FTIR, DSC, TGA, SEM, tensile test techniques, and static contact angle. DSC analysis showed that covalent incorporation of POSS into the PU network would increase the glass transition temperature (T g) of the systems. TG analysis demonstrated that the hybrid nanocomposites were indeed more oxidative thermal stable, compared to virgin polyurethane especially at high temperature. SEM revealed that both nano- and micro-sized POSS aggregates were shown to be dispersed heterogeneously in the polyurethane matrix, despite the expectation to be dispersed or corporate into molecular chains by chemical bonding between OH and NCO. According to the tensile test results, POSS-containing nanocomposites exhibited an increased modulus with an increasing POSS concentration at low POSS content, and with high loading, these values would decline. The results of the static contact angles revealed that the hydrophobicity of the hybrid material was significantly improved with the inclusion of POSS.
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