nach oben

Polymer Bulletin

Erschienen in:

02.10.2023 | ORIGINAL PAPER

Preparation and properties of self-healing disulfide bond-containing thermoset polyimide resins produced by the thiol-maleimide reaction

verfasst von: Yusuke Imamaki, Kaito Sugane, Mitsuhiro Shibata

Erschienen in: Polymer Bulletin | Ausgabe 7/2024

Einloggen

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

search-config

KI-gestützte Suche

Aus

Abstract

Thermally cured products (BLmP, m = 3, 33, and 12) of 4,4′-bismaleimidodiphenylmethane (BMIDPM), a thiol-terminated disulfide-containing polyether (LP-m), and pentaerythritol tetrakis(3-mercaptopropionate) (PETMP) were prepared at a maleimide:thiol ratio of 1:1. The influence of the feed monomer ratio, molecular weight, and crosslinking agent content of LP-m on the thermal, mechanical, and self-healing properties was investigated. Fourier-transform infrared (FT-IR) spectroscopy of the cured products revealed that the thiol-maleimide “click” reaction proceeded almost completely. The glass transition temperature (T_g), tensile strength, and tensile modulus of the cured products decreased with an increase in the fraction and molecular weight of LP-m and a decrease in the crosslinking agent content of LP-m. All the cured products were healed by treatment at 125 °C/5 MPa for 3 h. The tensile strength healing efficiency increased with an increase in the fraction and molecular weight of LP-m and a decrease in the crosslinking agent content of LP-m.

Vorheriger Artikel Influence of different gamma radiation doses on the physical, chemical and thermal properties of antimicrobial active packaging of poly (butylene adipate co-terephthalate) (PBAT) films additivated with orange essential oil

Nächster Artikel Determination of gentamicin by using square wave anodic stripping voltammetry with poly (β-cyclodextrin-p-toluene sulfonic acid) modified glassy carbon electrode

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!

Jetzt informieren

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!

Jetzt informieren

Nur mit Berechtigung zugänglich

Kloxin CJ, Scott TF, Adzima BJ, Bowman CN (2010) Covalent adaptable networks (CANs): a unique paradigm in cross-linked polymers. Macromolecules 43:2643–2653. https://doi.org/10.1021/ma902596sCrossRefPubMedPubMedCentral

Bowman CN, Kloxin CJ (2012) Covalent adaptable networks: reversible bond structures incorporated in polymer networks. Angew Chem Int Ed 51:4272–4274. https://doi.org/10.1002/anie.201200708CrossRef

Kloxin CJ, Bowman CN (2013) Covalent adaptable networks: smart, reconfigurable and responsive network systems. Chem Soc Rev 42:7161–7173. https://doi.org/10.1039/c3cs60046gCrossRefPubMed

Siccardi S, Amici J, Colombi S, Carvalho JT, Versaci D, Quartarone E, Pereira L, Bella F, Francia C, Bodoardo S (2022) UV-cured self-healing gel polymer electrolyte toward safer room temperature lithium metal batteries. Electrochim Acta 433:141265. https://doi.org/10.1016/j.electacta.2022.141265CrossRef

Zhao B, Bai Z, Lv H, Yan Z, Du Y, Guo X, Zhang J, Wu L, Deng J, Zhang DW, Che R (2023) Self-healing liquid metal magnetic hydrogels for smart feedback sensors and high-performance electromagnetic shielding. Nano-Micro Lett 15:79. https://doi.org/10.1007/s40820-023-01043-3CrossRef

Zhao W, Jiang J, Chen W, He Y, Lin T, Zhao L (2023) Radiation synthesis of rapidly self-healing, durable, and flexible poly(ionic liquid)/MXene gels with anti-freezing property for multi-functional strain sensors. Chem Eng J 468:143660. https://doi.org/10.1016/j.cej.2023.143660CrossRef

Denissen W, Winne JM, Du Prez FE (2016) Vitrimers: permanent organic networks with glasslike fluidity. Chem Sci 7:30–38. https://doi.org/10.1039/c5sc02223aCrossRefPubMed

Krishnakumara B, Prasanna Sankaa RVS, Wolfgang HB, Parthasarthy V, Rana S, Karak N (2020) Vitrimers: associative dynamic covalent adaptive networks in thermoset polymers. Chem Ebg J 385:123820. https://doi.org/10.1016/j.cej.2019.123820CrossRef

Guerre M, Taplan C, Winne JW, Du Prez FE (2020) Vitrimers: directing chemical reactivity to control material properties. Chem Sci 11:4855–4870. https://doi.org/10.1039/d0sc01069cCrossRefPubMedPubMedCentral

10.

Altuna FI, Hoppe CE, Williams RJJ (2018) Epoxy vitrimers: the effect of transesterification reactions on the network structure. Polymers 10:43. https://doi.org/10.3390/polym10010043CrossRefPubMedPubMedCentral

11.

Bhusal S, Oh C, Kang Y, Varshney V, Ren Y, Nepal D, Roy A, Kedziora G (2021) Transesterification in vitrimer polymers using bifunctional catalysts: modeled with solution-phase experimental rates and theoretical analysis of efficiency and mechanisms. J Phys Chem 125:2411–2424. https://doi.org/10.1021/acs.jpcb.0c10403CrossRef

12.

Canadell J, Goossens H, Klumperman B (2011) Self-healing materials based on disulfide links. Macromolecules 44:2536–2541. https://doi.org/10.1021/ma2001492CrossRef

13.

Pepels M, Filot I, Klumperman B, Goossens H (2013) Self-healing systems based on disulfide–thiol exchange reactions. Polym Chem 4:4955–4965. https://doi.org/10.1039/c3py00087gCrossRef

14.

Lei ZQ, Xiang HP, Yuan YJ, Rong MZ, Zhang MQ (2014) Room-temperature self-healable and remoldable cross-linked polymer based on the dynamic exchange of disulfide bonds. Chem Mater 26:2038–2046. https://doi.org/10.1021/cm4040616CrossRef

15.

Xue H, Ding X, Zhang Y, Li X, Xia J, Lin Q (2021) Disulfide group influence on the surface properties and reversible cross-linking functionalization of natural polymer coating. Polym Bull 78:6707–6721. https://doi.org/10.1007/s00289-020-03484-xCrossRef

16.

Mai VD, Shin SR, Lee DS, Kang I (2019) Thermal healing, reshaping and ecofriendly recycling of epoxy resin crosslinked with schiff base of vanillin and hexane-1,6-diamine. Polymers 11:293. https://doi.org/10.3390/polym11020293CrossRefPubMedPubMedCentral

17.

Mo R, Hu J, Huang H, Sheng X, Tunable ZX (2019) Self-healing and corrosion inhibiting dynamic epoxy–polyimine network built by post-crosslinking. J Mater Chem A 7:3031–3038. https://doi.org/10.1039/c8ta11546jCrossRef

18.

Shi Z, Kang J, Zhang L (2020) Water-enabled room-temperature self-healing and recyclable polyurea materials with super-strong strength, toughness, and large stretchability. ACS Appl Mater Interfaces 12:23484–23493. https://doi.org/10.1021/acsami.0c04414CrossRefPubMed

19.

Shahriari MH, Hadjizadeh A, Abdouss M (2023) Advances in self-healing hydrogels to repair tissue defects. Polym Bull 80:1155–1177. https://doi.org/10.1007/s00289-022-04133-1CrossRef

20.

Luzuriaga AR, Martin R, Markaide N, Rekondo A, Cabañero G, Rodríguez J, Odriozola I (2016) Epoxy resin with exchangeable disulfide crosslinks to obtain reprocessable, repairable and recyclable fiber-reinforced thermoset composite. Mater Horiz 3:241. https://doi.org/10.1039/c6mh00029kCrossRef

21.

Ortiz RA, Berlanga OA, AValdez AEG, Flores RA, Padilla JGT, Padilla MGM, (2016) Self-healing photocurable epoxy/thiol-ene systems using an aromatic epoxy resin. Adv Mater Sci Engn 2016:8245972. https://doi.org/10.1155/2016/8245972CrossRef

22.

Luzuriaga AR, Matxain JM, Ruipérez F, Martin R, Asua JM, Cabaňero G, Odriozola I (2016) Transient mechanochromism in epoxy vitrimer composites containing aromatic disulfide crosslinks. J Mater Chem C 4:6220–6223. https://doi.org/10.1039/c6tc02383eCrossRef

23.

Zhou F, Guo Z, Wang W, Lei X, Zhang B, Zhang H, Zhang Q (2018) Preparation of self-healing, recyclable epoxy resins and low-electrical resistance composites based on double-disulfide bond exchange. Compos Sci Technol 167:79–85. https://doi.org/10.1016/j.compscitech.2018.07.041CrossRef

24.

Cheng CB, Lu X, Zhou J, Qin R, Yang Y (2019) Dual cross-linked self-healing and recyclable epoxidized natural rubber based on multiple reversible effects. ACS Sustainable Chem Engn 7:4443–4455. https://doi.org/10.1021/acssuschemeng.8b06437CrossRef

25.

Tratnik N, Tanguy NR, Yan N (2023) Recyclable, self-strengthening starch-based epoxy vitrimer facilitated by exchangeable disulfide bonds. Chem Eng J 451:138610. https://doi.org/10.1016/j.cej.2022.138610CrossRef

26.

Yang Y, Lu X, Wang W (2017) A tough polyurethane elastomer with self-healing ability. Mater Design 127:30–36. https://doi.org/10.1016/j.matdes.2017.04.015CrossRef

27.

Jian X, Hu Y, Zhou W, Xiao L (2018) Self-healing polyurethane based on disulfide bond and hydrogen bond. Polym Adv Technol 29:463–469. https://doi.org/10.1002/pat.4135CrossRef

28.

Gao W, Bie M, Quan Y, Zhu J, Zhang W (2018) Self-healing, reprocessing and sealing abilities of polysulfide-based polyurethane. Polymer 151:27–33. https://doi.org/10.1016/j.polymer.2018.07.047CrossRef

29.

Chang K, Jia H, Gu SY (2019) A transparent, highly stretchable, self-healing polyurethane based on disulfide bonds. Eur Polym J 112:822–831. https://doi.org/10.1016/j.eurpolymj.2018.11.005CrossRef

30.

Iredale RJ, Ward C, Hamerton I (2017) Modern advances in bismaleimide resin technology: a 21st centuryperspective on the chemistry of addition polyimides. Prog Plym Sci 69:1–21. https://doi.org/10.1016/j.progpolymsci.2016.12.002CrossRef

31.

Nair CPR (2004) Advances in addition-cure phenolic resins. Prog Plym Sci 29:401–498. https://doi.org/10.1016/j.progpolymsci.2004.01.004CrossRef

32.

Stenzenberger HD (1994) Addition polyimides. In: Hergenrother PM (ed) High performance polymers. Adavances in polymer science, vol 117. Springer, Berlin, pp 181–190

33.

Shibata M, Hashimoto Y (2017) High performance thermosetting bismaleimide resins via thiol-maleimide “click” reaction. Eur Polym J 93:561–571. https://doi.org/10.1016/j.eurpolymj.2017.06.032CrossRef

34.

Ozawa M, Shibata M (2019) Reprocessable bismaleimide-diamine thermosets based on disulfide bonds. Recat Funct Polym 46:104404. https://doi.org/10.1016/j.reactfunctpolym.2019.104404CrossRef

35.

Zhang GZ, Fan ZK, Quan YW, Chen QM (2013) The preparation and physical properties of polysulfide-based elastomers through one-pot thiol-ene click reaction. eXPRESS Polym Lett 7:577–584. https://doi.org/10.3144/expresspolymlett.2013.55CrossRef

Titel: Preparation and properties of self-healing disulfide bond-containing thermoset polyimide resins produced by the thiol-maleimide reaction
verfasst von: Yusuke Imamaki
Kaito Sugane
Mitsuhiro Shibata
Publikationsdatum: 02.10.2023
Verlag: Springer Berlin Heidelberg
Erschienen in: Polymer Bulletin / Ausgabe 7/2024
Print ISSN: 0170-0839
Elektronische ISSN: 1436-2449
DOI: https://doi.org/10.1007/s00289-023-05007-w

Premium Partner

Marktübersichten

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

Zur Marktübersicht

Springer Professional

Abstract

Bitte loggen Sie sich ein, um Zugang zu Ihrer Lizenz zu erhalten.

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

Springer Professional "Wirtschaft+Technik"

Springer Professional "Technik"

Weitere Artikel der Ausgabe 7/2024

Biodegradable polyester-polybutylene succinate (PBS): a review

Production of PLA fibers with surface modifications and silver nanoparticle coating to impart antibacterial activity

Development of tamarind gum/β-CD-co-poly (MAA) hydrogels for pH-driven controlled delivery of capecitabine

A novel sustainable composite hydrogel containing nanocellulose to remove potentially toxic metals from contaminated water

Self-healing carboxylic acid-cured epoxy networks driven by the cyclodextrin–cyclohexane host–guest interaction

Preparation of molybdenum disulfide microspheres and their effect on the thermal conductivity of epoxy resin

Premium Partner

Marktübersichten