Novel route to sulfonated polyphosphazenes: Single-step synthesis using "noncovalent protection" of sulfonic acid functionality

被引:22
作者
Andrianov, AK [1 ]
Marin, A [1 ]
Chen, J [1 ]
Sargent, J [1 ]
Corbett, N [1 ]
机构
[1] Parallel Solut Inc, Cambridge, MA 02138 USA
关键词
D O I
10.1021/ma049736x
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
A single-step approach for the synthesis of polyphosphazenes containing sulfonic acid functionalities is developed. Polyphosphazene "sulfonation" is conducted via the direct replacement of chlorine atoms of the macromolecular precursor, poly(dichlorophosphazene), PDCP with a sulfonic acid containing nucleophile-hydroxybenzenesulfonic acid. The method makes use of "noncovalent" protection of the sulfonic acid functionality with a hydrophobic ammonium ion, such as the dimethyldipalmitylammonium ion, which then can be easily removed after the completion of the reaction. H-1, P-31, and C-13 NMR and size-exclusion HPLC studies revealed no macromolecular byproducts or noticeable degradation of the polyphosphazene backbone under the conditions of the synthesis. Both sulfonated polyphosphazene homopolymers and mixed substituent copolymers containing 4-ethylphenoxy side groups were synthesized and characterized.
引用
收藏
页码:4075 / 4080
页数:6
相关论文
共 14 条
[1]  
Allcock H. R., 2003, CHEM APPL POLYPHOSPH, P227
[2]   ALKANESULFONATION OF CYCLIC AND HIGH POLYMERIC PHOSPHAZENES [J].
ALLCOCK, HR ;
KLINGENBERG, EH ;
WELKER, MF .
MACROMOLECULES, 1993, 26 (20) :5512-5519
[3]   SULFONATION OF (ARYLOXY)PHOSPHAZENES AND (ARYLAMINO)PHOSPHAZENES - SMALL-MOLECULE COMPOUNDS, POLYMERS AND SURFACES [J].
ALLCOCK, HR ;
FITZPATRICK, RJ ;
SALVATI, L .
CHEMISTRY OF MATERIALS, 1991, 3 (06) :1120-1132
[4]   Polymeric carriers for oral uptake of microparticulates [J].
Andrianov, AK ;
Payne, LG .
ADVANCED DRUG DELIVERY REVIEWS, 1998, 34 (2-3) :155-170
[5]  
Andrianov AK, 1996, J APPL POLYM SCI, V60, P2289
[6]   Preparation of hydrogel microspheres by coacervation of aqueous polyphosphazene solutions [J].
Andrianov, AK ;
Chen, JP ;
Payne, LG .
BIOMATERIALS, 1998, 19 (1-3) :109-115
[7]   Poly(dichlorophosphazene) as a precursor for biologically active polyphosphazenes: Synthesis, characterization, and stabilization [J].
Andrianov, AK ;
Chen, JP ;
LeGolvan, MP .
MACROMOLECULES, 2004, 37 (02) :414-420
[8]   Protein release from polyphosphazene matrices [J].
Andrianov, AK ;
Payne, LG .
ADVANCED DRUG DELIVERY REVIEWS, 1998, 31 (03) :185-196
[9]  
ANDRIANOV AK, 1996, MICROPARTICULATE SYS, P127
[10]   Evaluation of methanol crossover in proton-conducting polyphosphazene membranes [J].
Fedkin, MV ;
Zhou, XY ;
Hofmann, MA ;
Chalkova, E ;
Weston, JA ;
Allcock, HR ;
Lvov, SN .
MATERIALS LETTERS, 2002, 52 (03) :192-196