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Titolo:
Synthesis and polymerization of chiral acrylamidosulfonic acids
Autore:
Ashraf, SA; Kane-Maguire, LAP; Pyne, SG; Wallace, GG;
Indirizzi:
Univ522,longong, Dept Chem, Intelligent Polymer Res Inst, Wollongong, NSW 2 Univ Wollongong Wollongong NSW Australia 2522 Res Inst, Wollongong, NSW 2
Titolo Testata:
MACROMOLECULES
fascicolo: 25, volume: 31, anno: 1998,
pagine: 8737 - 8743
SICI:
0024-9297(199812)31:25<8737:SAPOCA>2.0.ZU;2-H
Fonte:
ISI
Lingua:
ENG
Soggetto:
ASYMMETRIC POLYMERIZATION; POLYANILINE; ACRYLAMIDES; COMPOSITES; HYDROGELS; TACTICITY; WATER;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
27
Recensione:
Indirizzi per estratti:
Indirizzo: Kane-Maguire, LAP UnivWollongong,, Dept Chem, Intelligent Polymer Res Inst, Northfields Ave, Univ Wollongong Northfields Ave Wollongong NSW Australia2522
Citazione:
S.A. Ashraf et al., "Synthesis and polymerization of chiral acrylamidosulfonic acids", MACROMOLEC, 31(25), 1998, pp. 8737-8743

Abstract

Reductive amination of (1S)-(+)-10-camphorsulfonic acid with NaCNBH3/NH4OAc has afforded diastereomeric exo- and endo-aminosulfonic acids, that can be separated by crystallization from methanol. Treatment of these diastereomers with acryloyl chloride gave high yields of novel, chiral acrylamides that incorporate both a sulfonic acid substituent and a chiral auxiliary. Thefree radical (AIBN) polymerization of these acrylamides gave high yields (84-90%) of novel, water-soluble polyacrylamides (M-w = 5500-7800). H-1 NMR studies showed these to be essentially atactic. Their circular dichroism spectra were similar to their corresponding acrylamide monomers. This indicates that the sulfonic acid chiral auxiliary in the monomer precursors does not induce and/or maintain macroasymmetry in the resulting polyacrylamide chains. Hydrogels with equilibrium water contents as high as 99.96% could be obtained by copolymerizing {(NH4)(2)S2O8 initiator) these chiral acrylamides with equimolar acrylamide and varying ratios of N,N'-methylenebisacrylamide as cross-linker.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 28/11/20 alle ore 12:59:37