Abstract
First, styrene-ethylene-butylene-styrene (SEBS) was grafted using maleic anhydride (MA) to form SEBS-g-MA. Thereafter, SEBS-g-MA was modified with ethanolamine (EA), 2-Amino-2-methyl-1-propanol (AMP) or glycerine (Gly). The properties of the various copolymers were investigated. From FT-IR, the modified SEBS-g-MA was synthesized successfully. SEBS-g-MA modified with EA consists imide structure with a hydroxyl group and SEBS-g-MA modified with Gly consists ester structure with a hydroxyl group. SEBS-g-MA modified with AMP possess imide, ester and amide structures with hydroxyl or amine group. The results showed that the thermal stability of SEBS-g-MA was better than that of SEBS, and SEBS-g-MA modified with EA showed the best thermal stability among them. The Young’s modulus of SEBS-g-MA was better than that of SEBS, and SEBS-g-MA modified with EA showed higher Young’s modulus than SEBS-g-MA. Overall, SEBS-g-MA modified with EA showed enhanced thermal stability, tensile strength, and Young’s modulus.
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References
Holden G, Legge NR, Quirk R, Schroeder HE (1996) Thermoplastic elastomers2nd edn. Hanser Gardner Pubns, Cincinnati
Walker BM, Rader CP (1988) Handbook of thermoplastic elastomers2nd edn. Springer US, New York
Noshay A, McGrath JE (1977) Block copolymers, overview and critical survey. Academic Press, New York
Garakani MM, Arefazar A, Nazockdast H (2007) Study on morphological, rheological, and mechanical properties of PP/SEBS-MA/SGF hybrid composites. J Appl Polym Sci 104:2704–2710
Shi H, Li B, Chen C, Jia Y (2007) Preparation of HDPE/SEBS-g-MAH and its effect on mechanical properties of HDPE/wood flour composites. J Appl Polym Sci 104:3161–3170
Liu S-P, Ying JR, Zhou X-P, Xie X-L, Mai Y-W (2009) Dispersion, thermal and mechanical properties of polypropylene/magnesium hydroxide nanocomposites compatibilized by SEBS-g-MA. Compos Sci Technol 69:1873–1879
Li H, Sui X, Xie X-M (2017) High-strength and super-tough PA6/PS/PP/SEBS quaternary blends compatibilized by using a highly effective multi-phase compatibilizer: toward efficient recycling of waste plastics. Polymer 123:240–246
Li H, Xie X-M (2017) Morphology development and superior mechanical properties of PP/PA6/SEBS ternary blends compatibilized by using a highly efficient multi-phase compatibilizer. Polymer 108:1–10
Kausar A, Zulfiqar S, Shabbir S, Ishaq M, Ilyas Sarwar M (2007) Mechanical properties of functionalized SEBS based inorganic hybrid materials. Polym Bull 59:457–468
Ganguly A, Bhowmick AK (2007) Sulfonated styrene-(ethylene-co-butylene)-styrene /montmorillonite clay nanocomposites: synthesis, morphology, and properties. Nanoscale Res Lett 3:36–44
Wang Q, Lu Y, Li N (2016) Preparation, characterization and performance of sulfonated poly(styrene-ethylene/butylene-styrene) block copolymer membranes for water desalination by pervaporation. Desalination 390:33–46
Lin J-J, Cheng I-J, Chen C-N, Kwan C-C (2000) Synthesis, characterization, and interfacial behaviors of poly(oxyethylene)-grafted SEBS copolymers. Ind Eng Chem Res 39:65–71
Chang Y-C, Chou C-C, Lin J-J (2005) Emulsion intercalation of Smectite clays with comb-branched copolymers consisting of multiple quaternary amine salts and a poly(styrene−butadiene−styrene) backbone. Langmuir 21:7023–7028
Ganguly A, Bhowmick AK (2009) Effect of polar modification on morphology and properties of styrene-(ethylene-co-butylene)-styrene triblock copolymer and its montmorillonite clay-based nanocomposites. J Mater Sci 44:903–918
Xu W, Cheng Z, Zhang Z, Zhang L, Zhu X (2011) Modification of SEBS rubber via iron-mediated AGET ATRP in the presence of limited amounts of air. React Funct Polym 71:634–640
Zahra M, Zulfiqar S, Yavuz CT, Kweon H-S, Ilyas Sarwar M (2014) Conductive nanocomposite materials derived from SEBS-g-PPy and surface modified clay. Compos Sci Technol 100:44–52
Yao H, Zhang N, Shen K, Song N, Shi K, Zhu S, Zhang Y, Guan S (2017) From a flexible hyperbranched polyimide to a microporous polyimide network: microporous architecture and carbon dioxide adsorption. Polymer 115:176–183
Zhou T, Zhang A, Zhao C, Liang H, WU Z, Xia J (2007) Molecular chain movements and transitions of SEBS above room temperature studied by moving-window two-dimensional correlation infrared spectroscopy. Macromolecules 40:9009–9017
Allen NS, Edge M, Wilkinson A, Liauw CM, Mourelatou D, Barrio J, Martinez-Zaporta MA (2000) Degradation and stabilisation of styrene–ethylene–butadiene–styrene (SEBS) block copolymer. Polym Degrad Stab 71:113–122
Schoukens G, Martins J, Samyn P (2013) Insights in the molecular structure of low- and high-molecular weight poly(styrene-maleic anhydride) from vibrational and resonance spectroscopy. Polymer 54:349–362
Dellacasa E, Forouharshad M, Rolandi R, Pastorino L, Monticelli O (2018) Poly(styrene-co-maleic anhydride) nanoparticles as protein carriers. Mater Lett 220:241–244
Vlad S, Oprea S, Stanciu A, Ciobanu C, Bulacovschi V (2000) Polyesters based on unsaturated diols. Eur Polym J 36:1495–1501
Dai J, Ma S, Liu X, Han L, Wu Y, Dai X, Zhu J (2015) Synthesis of bio-based unsaturated polyester resins and their application in waterborne UV-curable coatings. Prog Org Coat 78:49–54
Fonseca AC, Lopes IM, Coelho JFJ, Serra AC (2015) Synthesis of unsaturated polyesters based on renewable monomers: structure/properties relationship and crosslinking with 2-hydroxyethyl methacrylate. React Funct Polym 97:1–11
Xu S, Liu L, Wang Y (2017) Network cross-linking of polyimide membranes for pervaporation dehydration. Sep Purif Technol 185:215–226
Martínez-Cocoletzia A, Ruizb J-C, Kasparekc E, Ortegaa A, Garcia-Uriosteguid L, Girard-Lauriaultc P-L, Burillo G (2018) Primary-amine surface functionalization of polytetrafluoroethylene films by radiation grafting of aminated polyacryloyl chloride. Radiat Phys Chem 149:65–72
Liu L, Wang H, Qi X, Kong L, Cui J, Zhang X, Shi H (2015) Shape-stabilized phase change materials based on poly(ethylene-graft-maleic anhydride)-g-alkyl alcohol comb-like polymers. Sol Energy Mater Sol Cells 143:21–28
Wongthong P, Nakason C, Pan Q, Rempel GL, Kiatkamjornwong S (2013) Modification of deproteinized natural rubber via grafting polymerization with maleic anhydride. Eur Polym J 49:4035–4046
Sütekin SD, Atıcı AB, Güven O, Hoffman AS (2018) Controlling of free radical copolymerization of styrene and maleic anhydride via RAFT process for the preparation of acetaminophen drug conjugates. Radiat Phys Chem 148:5–12
Niu S, Zhou Y, Yu H, Lu C, Han K (2017) Investigation on thermal degradation properties of oleic acid and its methyl and ethyl esters through TG-FTIR. Energy Convers Manag 149:495–504
Zuo Y, Gu J, Yang L, Qiao Z, Tan H, Zhang Y (2013) Synthesis and characterization of maleic anhydride esterified cornstarch by the dry method. Int J Biol Macromol 62:241–247
Sclavons M, Franquinet P, Carlier V, Verfaillie G, Fallais I, Laurent M, Thyrion FC (2000) Quantification of the maleic anhydride grafted onto polypropylene by chemical and viscosimetric titrations, and FTIR spectroscopy. Polymer 41:1989–1999
Wongthong P, Nakason C, Pan Q, Rempel GL, Kiatkamjornwong S (2014) Styrene-assisted grafting of maleic anhydride onto deproteinized natural rubber. Eur Polym J 59:144–155
Wróblewska AA, Lingier S, Noordijk J, Du Prez FE, De Wildeman SMA, Bernaerts KV (2017) Polyamides based on a partially bio-based spirodiamine. Eur Polym J 96:221–231
Yao J, Pantano MF, Pugno NM, Bastiaansen CWM, Peijs T (2015) High-performance electrospun co-polyimide nanofibers. Polymer 76:105–112
Hsiao S-H, Chen Y-Z (2017) Electroactive and ambipolar electrochromic polyimides from arylene diimides with triphenylamine N-substituents. Dyes Pigments 144:173–183
Xu S, Wang Y (2015) Novel thermally cross-linked polyimide membranes for ethanol dehydration via pervaporation. J Membr Sci 496:142–155
Gunbas ID, Wouters MEL, van Benthem RATM, Koning CE, Noordover BAJ (2013) PDMS-modified poly(styrene-alt-maleic anhydride)s as water-borne coatings based on surfactant-free latexes. Prog Org Coat 76:1720–1725
Zhang C, Li P, Cao B (2017) Decarboxylation crosslinking of polyimides with high CO2/CH4 separation performance and plasticization resistance. J Membr Sci 528:206–216
Dérand H, Wesslén B (1995) Synthesis and characterization of anionic graft copolymers containing poly(ethylene oxide) grafts. J Polym Sci A Polym Chem 33:571–579
Dérand H, Wesslén B, Wittgren B, Wahlund KG (1996) Poly(ethylene glycol) graft copolymers containing carboxylic acid groups: aggregation and viscometric properties in aqueous solution. Macromolecules 29:8770–8775
Rietman EA, Kaplan ML (1990) Single-ion conductivity in comblike polymers. Journal of Polymer Science Part C: Polymer Letters banner 28:187–191
Wang Z, Wei T, Xue X, He M, Xue J, Song M, Wu S, Kang H, Zhang L, Jia Q (2014) Synthesis of fully bio-based polyamides with tunable properties by employing itaconic acid. Polymer 55:4846–4856
Cui L, Chao D, Zhang J, Mao H, Li Y, Wang C (2010) Synthesis and properties of novel electroactive polyamide containing crown ether in the main chain. Synth Met 160:400–404
Huang ZZ, Wan XM, Xiao HB, Sheng SR, Song CS (2010) A novel soluble polyamide containing xanthene structure and trifluoromethylphenoxy pendent. Chin Chem Lett 21:242–244
Pérez-Calixto MP, Ortega A, Garcia-Uriostegui L, Burillo G (2016) Synthesis and characterization of N-vinylcaprolactam/N,N-dimethylacrylamide grafted onto chitosan networks by gamma radiation. Radiat Phys Chem 119:228–235
Cruza A, García-Uriosteguib L, Ortegaa A, Isoshimac T, Burillo G (2017) Radiation grafting of N-vinylcaprolactam onto nano and macrogels of chitosan: synthesis and characterization. Carbohydr Polym 155:303–314
Passaglia E, Ghetti S, Picchioni F, Ruggeri G (2000) Grafting of diethyl maleate and maleic anhydride onto styrene-b-(ethylene-co-1-butene)-b-styrene triblock copolymer (SEBS). Polymer 41:4389–4400
Rätzsch M, Arnold M, Borsig E, Bucka H, Reichelt N (2002) Radical reactions on polypropylene in the solid state. Prog Polym Sci 27:1195–1282
Dickens B (1982) Thermal degradation study of isotactic polypropylene using factor-jump thermogravimetry. J Polym Sci A Polym Chem 20:1169–1183
Hinsken H, Moss S, Pauquet J-R, Zweifel H (1991) Degradation of polyolefins during melt processing. Polym Degrad Stab 34:279–293
De Roover B, Sclavons M, Carlier V, Devaux J, Legras R, Momtaz A (1995) Molecular characterization of maleic anhydride-functionalized polypropylene. Journal of Polymer Science Part A: Polymer Chemistry 33:829–842
Kruse TM, Wong H-W, Broadbelt LJ (2003) Mechanistic modeling of polymer pyrolysis: polypropylene. Macromolecules 36:9594–9607
Panaitescu DM, Gabor RA, Nicolae CA, Ghiurea M (2014) Influence of melt processing induced orientation on the morphology and mechanical properties of poly(styrene-b-ethylene/butylene-b-styrene) block copolymers and their composites with graphite. Mater Des 64:694–705
Ganguly A, Bhowmick AK (2008) Insights into montmorillonite nanoclay based ex situ nanocomposites from SEBS and modified SEBS by small-angle X-ray scattering and modulated DSC studies. Macromolecules 41:6246–6253
Mäder D, Bruch M, Maier R-D, Stricker F, Mülhaupt R (1999) Glass transition temperature depression of elastomers blended with poly(propene)s of different stereoregularities. Macromolecules 32:1252–1259
Wang L, Hong S, Hu H, Zhao J, Han CC (2007) The surface morphology evolution of an ultrathin film of poly[styrene-b-(ethylene-co-butylene)-b-styrene] during its Dewetting process. Langmuir 23:2304–2307
Bar G, Thomann Y (1998) Characterization of the morphologies and nanostructures of blends of poly(styrene)-block-poly(ethene-co-but-1-ene)-block-poly(styrene) with isotactic and atactic polypropylenes by tapping-mode atomic force microscopy. Langmuir 14:1219–1226
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Chuang, PL., Nien, YH. Synthesis and characterization of maleic anhydride grafted SEBS modified with ethanolamine, 2-amino-2-methyl-1-propanol or glycerine. J Polym Res 26, 66 (2019). https://doi.org/10.1007/s10965-019-1723-7
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DOI: https://doi.org/10.1007/s10965-019-1723-7