Furan-functionalised melamine-formaldehyde particles performing Diels-Alder reactions

被引:13
|
作者
Urdl, Katharina [1 ]
Weiss, Stephanie [1 ]
Karpa, Alexandra [2 ,3 ,4 ]
Peric, Matea [1 ]
Zikulnig-Rusch, Edith [1 ]
Brecht, Marc [2 ,3 ,4 ]
Kandelbauer, Andreas [2 ]
Mueller, Uwe [1 ]
Kern, Wolfgang [5 ,6 ]
机构
[1] Wood K Plus Competence Ctr Wood Composites & Wood, Altenberger Str 69, A-4040 Linz, Austria
[2] Reutlingen Univ, Sch Appl Chem, D-72762 Reutlingen, Germany
[3] Univ Tubingen, Inst Phys & Theoret Chem, D-72076 Tubingen, Germany
[4] Univ Tubingen, Lisa Ctr, D-72076 Tubingen, Germany
[5] Univ Leoben, Chair Chem Polymer Mat, A-8700 Leoben, Austria
[6] Polymer Competence Ctr Leoben GmbH, A-8700 Leoben, Austria
关键词
Thermoset; Melamine-formaldehyde; Furan-functionalised; Particle; Diels-Alder reaction; RESIN MICROSPHERES; RAMAN-SPECTROSCOPY; POLYMER NETWORKS; C-13; MICROPARTICLES; IMMUNOASSAY; FABRICATION; CHEMISTRY; COMPLEX;
D O I
10.1016/j.eurpolymj.2018.08.023
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Functionalised particles are highly requested in materials research, as they can be used as vital components in many advanced applications such as smart materials, functional coatings, drug carrier systems or adsorption materials. In this study, furan-functionalised melamine-formaldehyde (MF) particles were successfully prepared for the first time using an organic sol-gel process. Commercially available 2-Aminomethylfuran (AMF) and 2-Aminomethyl-5-methylfuran (AMMF) were used as modifying agents. In the isolated polymer particles, a melamine (M) to modifying agent ratio of M:AMF mol/mol 2.04:1 and M:AMMF ratio of mol/mol 1.25:1 was used. The obtained particles were isolated in various centrifugation and re-dispersion cycles and analysed using ATR-FT-IR, Raman and solid state C-13 NMR spectroscopy, TGA, SEM and DSC measurements. Upon functionalisation the size of the MF particles increased (MF 1.59 mu m, 27% CV (coefficient of variation); MF-AMF 2.56 mu m, 25% CV; MF-AMMF 2.20 mu m, 35% CV). DSC measurements showed that another type of exothermic residual reactivity besides condensation-based curing takes place with the furan-modified particles that is not related to the liberation of volatile compounds. The newly obtained particles are able to undergo Diels-Alder reactions with maleimide groups. The characteristic IR and Raman absorbance bands of the reaction products after the particles were reacted with 4,4'-Diphenylmethanebismaleimide reagent confirm the formation of a Diels-Alder adduct.
引用
收藏
页码:225 / 234
页数:10
相关论文
共 50 条
  • [21] Diels-Alder and Formal Diels-Alder Cycloaddition Reactions of Ynamines and Ynamides
    Duret, Guillaume
    Le Fouler, Vincent
    Bisseret, Philippe
    Bizet, Vincent
    Blanchard, Nicolas
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (46) : 6816 - 6830
  • [22] DIELS-ALDER REACTIONS OF CYCLOALKENONES .18. UNUSUAL DIELS-ALDER REACTIONS OF EUCARVONE
    GUO, M
    MINUTI, L
    TATICCHI, A
    WENKERT, E
    JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (04): : 1366 - 1368
  • [23] DIELS-ALDER REACTION OF FURAN WITH SOME DIENOPHILES
    EGGELTE, TA
    KONING, HD
    HUISMAN, HO
    TETRAHEDRON, 1973, 29 (16) : 2491 - 2493
  • [25] Synthetic applications or furan Diels-Alder chemistry
    Kappe, CO
    Murphree, SS
    Padwa, A
    TETRAHEDRON, 1997, 53 (42) : 14179 - 14233
  • [26] An efficient synthesis of isoindolo[2,1-a]quinoline derivatives via imino Diels-Alder and intramolecular Diels-Alder reactions with furan
    Kouznetsov, Vladimir V.
    Cruz, Uriel Mora
    Zubkov, Fedor I.
    Nikitina, Eugenia V.
    SYNTHESIS-STUTTGART, 2007, (03): : 375 - 384
  • [27] Diels-Alder reactions of fullerenes
    Sliwa, W
    FULLERENE SCIENCE AND TECHNOLOGY, 1997, 5 (06): : 1133 - 1175
  • [28] DIELS-ALDER REACTIONS OF PIPERYLENES
    BROCKSOM, TJ
    CONSTANTINO, MG
    JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (18): : 3450 - 3453
  • [29] DIELS-ALDER REACTIONS WITH DIHYDRONAPHTHALENES
    DENO, NC
    CHAFETZ, H
    JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (03): : 449 - 449
  • [30] DIELS-ALDER REACTIONS OF ISOINDOLE
    STEVENS, SR
    SMITH, RG
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1978, 176 (SEP): : 2 - 2