Acyl-substituted ferrocenes as driers for solvent-borne alkyd paints

被引:30
作者
Erben, Milan [1 ]
Vesely, David [2 ]
Vinklarek, Jaromir [1 ]
Honzicek, Jan [1 ]
机构
[1] Univ Pardubice, Fac Chem Technol, Dept Gen & Inorgan Chem, Pardubice 53210, Czech Republic
[2] Univ Pardubice, Fac Chem Technol, Inst Chem & Technol Macromol Mat, Pardubice 53210, Czech Republic
关键词
Ferrocenes; Alkyd; Drier; FTIR; ESR; COMPLEXES; OXIDATION; RADICALS; CARCINOGENICITY; MECHANISMS; PARAMETERS; BIPYRIDINE; CATALYST; ADDUCTS; PEROXY;
D O I
10.1016/j.molcata.2011.10.024
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Ferrocenes bearing acyl substituents in the cyclopentadienyl rings [Fe(eta(5)-C5H4COR)(eta(5)-C5H5)] and [Fe(eta(5)-C5H4COR)(2)] (R = CH3, CF3 and Ph) were examined as new driers for solvent-borne alkyd binder. All studied ferrocenes were found to be active catalysts for cross-linking reaction of the alkyd. These iron(II) compounds give solid polymeric films with hardness and drying time comparable to the commercial cobalt(II) drier. Acetyl- and benzoyl-substituted ferrocenes show an excellent synergic effect with the cobalt drier giving hard polymeric films within short drying time. The kinetics of the alkyd autoxidation was followed by FTIR spectroscopy. Spin-trapping ESR technique has proven the important role of the ferrocenium cation upon decomposition of hydroperoxides by ferrocene-based driers. The peroxy and alkoxy radicals, appearing in drying process, were resolved by the new spin trap methyl-N-mesityl nitrone. (C) 2011 Elsevier B.V. All rights reserved.
引用
收藏
页码:13 / 21
页数:9
相关论文
共 46 条
[1]   Polymer supports for low-temperature fuel cell catalysts [J].
Antolini, E. ;
Gonzalez, E. R. .
APPLIED CATALYSIS A-GENERAL, 2009, 365 (01) :1-19
[2]   FUNCTIONALLY-SUBSTITUTED DERIVATIVES OF (ETA(5)-CYCLOPENTADIENYL)TRIISOPROPOXYTITANIUM AND (ETA(5)-CYCLOPENTADIENYL)TRICHLOROTITANIUM [J].
BARRY, S ;
KUCHT, A ;
KUCHT, H ;
RAUSCH, MD .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 489 (1-2) :195-199
[3]   FREE-RADICAL SUBSTITUTION OF FERRICINIUM ION - MECHANISM OF ARYLATION OF FERROCENE [J].
BECKWITH, AL ;
LEYDON, RJ .
TETRAHEDRON, 1964, 20 (04) :791-&
[4]  
Bieleman JH, 2002, MACROMOL SYMP, V187, P811, DOI 10.1002/1521-3900(200209)187:1<811::AID-MASY811>3.0.CO
[5]  
2-L
[6]   Inhalation toxicity and carcinogenicity studies of cobalt sulfate [J].
Bucher, JR ;
Hailey, JR ;
Roycroft, JR ;
Haseman, JK ;
Sills, RC ;
Grumbein, SL ;
Mellick, PW ;
Chou, BJ .
TOXICOLOGICAL SCIENCES, 1999, 49 (01) :56-67
[7]   SPIN TRAPPING - ELECTRON-SPIN-RESONANCE PARAMETERS OF SPIN ADDUCTS [J].
BUETTNER, GR .
FREE RADICAL BIOLOGY AND MEDICINE, 1987, 3 (04) :259-303
[8]   Synthesis, structures, and properties of ''encapsulated'' iron and cobalt metallocenes with highly isopropylated cyclopentadienyl rings [J].
Burkey, DJ ;
Hays, ML ;
Duderstadt, RE ;
Hanusa, TP .
ORGANOMETALLICS, 1997, 16 (07) :1465-1475
[9]   REACTION OF SOME FERROCENYL KETONES WITH ANHYDROUS SILVER TETRAFLUOROBORATE, A NEW ROUTE TO SUBSTITUTED FERRICENIUM SALTS [J].
CARTY, P ;
DOVE, MFA .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1971, 28 (01) :125-&
[10]   Organometallic Complexes: New Tools for Chemotherapy [J].
Chavain, N. ;
Biot, C. .
CURRENT MEDICINAL CHEMISTRY, 2010, 17 (25) :2729-2745