Synthesis of biodegradable chiral poly(ester-imide)s derived from valine-, leucine- and tyrosine-containing monomers.
The present demand for a drastic reduction in environmental pollution is extended to qualitative change in the approach to development of biodegradable polymers. The aim of this article is to focus on the synthesis of biodegradable optically active poly(ester-imide)s (PEI)s, which compose of different amino acids in the main chain as well as in the side chain. These polymers were synthesized by polycondensation of diacid monomers such as 5-(2-phthalimidyl-3-methyl butanoylamino) isophthalic acid (1), 5-(4-methyl-2-phthalimidyl pentanoylamino)isophthalic acid (2) with N,N'-(pyromellitoyl)-bis-L: -tyrosine dimethyl ester (3) as a phenolic diol. The direct polycondensation reaction was carried out in a system of tosyl chloride, pyridine and N,N-dimethylformamide as a condensing agent under conventional heating conditions. The optically active PEIs were obtained in good yield and moderate inherent viscosity. The synthesized polymers were characterized by means of FT-IR, (1)H-NMR, elemental and thermo gravimetric analysis techniques. In addition, in vitro toxicity and soil burial test were employed for assessing the sensitivity of these compounds to microbial degradation. To this purpose, biodegradability behavior of the monomers and polymers were investigated in culture media and soil condition. The results of this study revealed that synthesized monomers and their derived polymers are biologically active and probably microbiologically biodegradable.
Organic Polymer Chemistry Research Laboratory, Department of Chemistry, Isfahan University of Technology, Islamic Republic of Iran. mallak@cc.iut.ac.ir
Shadpour
S
Mallakpour
Parvin
P
Asadi
Mohammad R
MR
Sabzalian
D001419:Bacteria / Q000254:growth & development / Q000378:metabolism*; D001673:Biodegradation, Environmental; D004952:Esters / Q000737:chemistry / Q000378:metabolism; D005658:Fungi / Q000254:growth & development / Q000378:metabolism*; D007094:Imides / Q000737:chemistry / Q000378:metabolism; D007700:Kinetics; D007930:Leucine / Q000737:chemistry / Q000378:metabolism; D015394:Molecular Structure; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D014443:Tyrosine / Q000737:chemistry / Q000378:metabolism; D014633:Valine / Q000737:chemistry / Q000378:metabolism
D004952:Esters; D007094:Imides; D011108:Polymers; D014443:Tyrosine; D007930:Leucine; D014633:Valine