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Titolo:
NOVEL ACRYLAMIDO MONOMERS WITH HIGHER HYDROPHILICITY AND IMPROVED HYDROLYTIC STABILITY .1. SYNTHETIC ROUTE AND PRODUCT CHARACTERIZATION
Autore:
SIMOALFONSO E; GELFI C; SEBASTIANO R; CITTERIO A; RIGHETTI PG;
Indirizzi:
LITA,VIA FRATELLI CERVI 93 I-20090 SEGRATE MILANO ITALY UNIV VALENCIA,FAC QUIM,DEPT QUIM ANALIT E-46100 BURJASSOT SPAIN CNR,ITBA I-20133 MILAN ITALY POLYTECH MILANO,DEPT CHEM I-20133 MILAN ITALY UNIV CALABRIA,DEPT CELL BIOL RENDE COSENZA ITALY
Titolo Testata:
Electrophoresis
fascicolo: 4, volume: 17, anno: 1996,
pagine: 723 - 731
SICI:
0173-0835(1996)17:4<723:NAMWHH>2.0.ZU;2-X
Fonte:
ISI
Lingua:
ENG
Soggetto:
CAPILLARY ZONE ELECTROPHORESIS; IMMOBILIZED PH GRADIENTS; ACRYLOYL TRIS GELS; POLYACRYLAMIDE GELS; FRACTIONATION TECHNIQUES; ORGANIC ENVIRONMENT; MATRIX; HLGE; PHOTOPOLYMERIZATION; POLYMERS;
Keywords:
N-SUBSTITUTED ACRYLAMIDES; N-ACRYLOYLAMINOPROPANOL;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
50
Recensione:
Indirizzi per estratti:
Citazione:
E. Simoalfonso et al., "NOVEL ACRYLAMIDO MONOMERS WITH HIGHER HYDROPHILICITY AND IMPROVED HYDROLYTIC STABILITY .1. SYNTHETIC ROUTE AND PRODUCT CHARACTERIZATION", Electrophoresis, 17(4), 1996, pp. 723-731

Abstract

The novel acrylamido monomer reported by our group (N-acryloylaminoethoxyethanol, AAEE; Chiari et al., Electrophoresis 1994, 15, 177-186), found to combine high hydrophilicity with extraordinary resistance to alkaline hydrolysis, has come under closer scrutiny due to unexpected and random autopolymerization while stored as a 1/1 v/v water solutionat 4 degrees C (possibly due to a greater oxidability of the ether group). We have additionally found a unique degradation pathway of the monomer, called ''1-6 H-transfer'', by which the C-1 (on the double bond site), by constantly ramming against the C-6, next to the ether oxygen (O-7, which in fact favors the transfer of the hydrogen atom by C-1), produces radicals which more efficiently add to the monomer favoring autopolymerization and cross-linking. A number of novel monomers is proposed while maintaining the other unique chracteristics of AAEE. One of them, N-acryloylaminopropanol, offers all the unique, special qualitites of AAEE, without the noxious aspects of autopolymerization. Additionally, a synthetic route was optimized, yielding an essentially pure product in a single reaction step, with a yield >99% and an equivalent purity (>99%). The synthesis consists in reacting acryloyl chloride at -40 degrees C in presence of a twofold molar excess of aminopropanol and in ethanol (instead of methanol) as solvent. Other solvents, as well as the use of triethylamine for neutralizing the HCl produced,were found to give a variety of undesired byproducts.

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Documento generato il 01/12/20 alle ore 16:11:33