The role of multifunctionalized amine structure and reaction conditions on the transformations of crosslinked copoly(styrene-p-nitrophenylacrylate)
✍ Scribed by Marko Zupan; Peter Krajnc; Stojan Stavber
- Publisher
- John Wiley and Sons
- Year
- 1998
- Tongue
- English
- Weight
- 155 KB
- Volume
- 36
- Category
- Article
- ISSN
- 0887-624X
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✦ Synopsis
Crosslinked copoly(styrene-p-nitrophenylacrylates), containing 2% ( 1) or 4% DVB ( 2) were converted with various diaminoalkanes (1,2-diaminoethane 3a, 1,4diaminobutane 3b, 1,8-diaminooctane 3c) to amides. The degree of additional crosslinking depended on the chain length of the diaminoalkane, the molar ratio of ester function in 1 or 2 to diaminoalkane, solvent polarity (dimethylformamide, chloroform, toluene), while reaction temperature (50 or 100ЊC) had only a minor effect. 2 was also converted with various amines bearing additional functional groups (ethanolamine, 3-amino-1propanol, 4-aminomethylpyridine, 2-(2-aminoethylamino)-ethanol, 2-(2-aminoethoxy)-ethanol, 6-aminocaproic acid, N-propylaminomorpholine, 3-N,N-diethylamino-1propylamine) to the corresponding amides. The swelling ability of the resins depended on the crosslinking of the starting copoly(styrene-p-nitrophenylacrylate) ( 1, 2), the structure of the amide, the degree of additional crosslinking, and solvent polarity (chloroform, dimethylformamide, methanol, toluene). The accessibility of nitrogen atoms in the polymer matrix was examined by EtX functionalization of the 3-N,N-diethylamino-1-propylamine derivative ( 10) and 4-aminomethylpyridine derivative (13), and more than 85% functionalization was found.