ICCAS OpenIR
Unexpected Synthesis of Segmented Poly(hydroxyurea-urethane)s from Dicyclic Carbonates and Diamines by Organocatalysis
Bossion, Amaury1,2,3; Aguirresarobe, Roberto H.1,2; Irusta, Lourdes1,2; Taton, Daniel4; Cramail, Henri3; Grau, Etienne3; Mecerreyes, David1,2,5; Su, Cui6,7; Liu, Guoming6; Mueller, Alejandro J.1,2; Sardon, Haritz1,2
2018-08-14
Source PublicationMACROMOLECULES
ISSN0024-9297
Volume51Issue:15Pages:5556-5566
AbstractA complete study of the effect of different organocatalysts on the step -growth polyaddition of a five -membered dicyclic carbonate, namely diglycerol dicarbonate, with a poly(ethylene glycol)-based diamine in bulk at 120 degrees C was first carried out. The reaction was found to be dramatically catalyst-dependent, higher rates being observed in the presence of strong bases, such as phosphazenes (t-Bu-P-4 or P-4) and 5,7-triazabicyclo[4.4.0]dec-5-ene (TBD). Unexpectedly, the as-formed urethane linkages entirely vanished with time, as evidenced by FTIR and C-13 NMR spectroscopies, while signals due to urea bond formation progressively appeared. An advantage of the chemical transformation occurring from urethane to urea linkages was further taken by optimizing the polymerization conditions to access a range of poly(hydroxyurea-urethane)s (PHUUs) with precise urethane to urea ratio in a one-pot process. Characterization of the corresponding polymers by rheological measurements showed that the storage modulus reached a plateau at high temperatures and at high urea contents. The application temperature range of poly(hydroxyurea urethane)s could thus be increased from 30 to 140 degrees C, as for regular polyurethanes. Furthermore, SAXS and phase-contrast microscopy images demonstrated that increasing the urea content improved the phase separation between soft and hard segments of these PHUUs. Altogether, this novel, straightforward, efficient, and environmentally friendly strategy enables the access to non-isocyanate poly(urea urethane)s with tunable urethane-to-urea ratio from five-membered dicyclic carbonates following an organocatalytic pathway.
DOI10.1021/acs.macromol.8b00731
Indexed BySCI
Language英语
WOS IDWOS:000442185700009
PublisherAMER CHEMICAL SOC
Citation statistics
Cited Times:13[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/42438
Collection中国科学院化学研究所
Corresponding AuthorSardon, Haritz
Affiliation1.Univ Basque Country, UPV EHU, Fac Chem, POLYMAT, Paseo Manuel de Lardizabal 3, Donostia San 20018, Sebastian, Spain
2.Univ Basque Country, UPV EHU, Fac Chem, Polymer Sci & Technol Dept, Paseo Manuel de Lardizabal 3, Donostia San 20018, Sebastian, Spain
3.ENSCBP, CNRS, LCPO, 16 Ave Pey Berland, F-33607 Pessac, France
4.Univ Bordeaux, ENSCBP, LCPO, 16 Ave Pey Berland, F-33607 Pessac, France
5.Basque Fdn Sci, Ikerbasque, E-48011 Bilbao, Spain
6.Chinese Acad Sci, Inst Chem, CAS Res Educ Ctr Excellence Mol Sci, CAS Key Lab Engn Plast, Beijing 100190, Peoples R China
7.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
Recommended Citation
GB/T 7714
Bossion, Amaury,Aguirresarobe, Roberto H.,Irusta, Lourdes,et al. Unexpected Synthesis of Segmented Poly(hydroxyurea-urethane)s from Dicyclic Carbonates and Diamines by Organocatalysis[J]. MACROMOLECULES,2018,51(15):5556-5566.
APA Bossion, Amaury.,Aguirresarobe, Roberto H..,Irusta, Lourdes.,Taton, Daniel.,Cramail, Henri.,...&Sardon, Haritz.(2018).Unexpected Synthesis of Segmented Poly(hydroxyurea-urethane)s from Dicyclic Carbonates and Diamines by Organocatalysis.MACROMOLECULES,51(15),5556-5566.
MLA Bossion, Amaury,et al."Unexpected Synthesis of Segmented Poly(hydroxyurea-urethane)s from Dicyclic Carbonates and Diamines by Organocatalysis".MACROMOLECULES 51.15(2018):5556-5566.
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