Synthesis and biodegradation studies of optically active poly(amide–imide)s based on N,N′-(pyromellitoyl)-bis-l-amino acid

Five new optically active poly(amide–imide)s (PAIs) (PAI3a–PAI3e) were synthesized through the direct polycondensation reaction between chiral N,N′-(pyromellitoyl)-bis-l-amino acids and 4,4′-diaminodiphenyl ether. The resulted polymers were fully characterized by means of Fourier transform infrared (FTIR) and proton nuclear magnetic resonance spectroscopy, elemental analysis, inherent viscosity measurement, solubility tests, specific rotation, and thermogravimetric analysis (TGA). The biodegradation studies of the PAIs were performed in soil and in phosphate buffer solution. The surface morphology and hydrophobicity of the biodegraded PAI films were investigated. FTIR spectra showed structural changes on PAI powders being treated in phosphate buffer solution. The TGA data showed that the thermal stability of PAI powders decreased with the degradation time. The collected degradation products were soluble in water and had absorption in ultraviolet and visible light region. Possible biodegradation mechanism of amino acid-based PAIs was explored.

[1]  Donghong Yu,et al.  New optically active poly(amide-imide)s based on N,N′-(pyromellitoyl)-bis-L-amino acid and methylene diphenyl-4,4′-diisocyanate: synthesis and characterization , 2014 .

[2]  S. Mallakpour,et al.  A green route for the synthesis of novel optically active poly(amide–imide) nanocomposites containing N-trimellitylimido-l-phenylalanine segments and modified alumina nanoparticles , 2014 .

[3]  S. Mallakpour,et al.  High-performance nanostructure chiral poly(amide–imide)s containing benzamide and amino acid linkages: Preparation, characterization and ultrasonic effect on the morphology , 2013 .

[4]  S. Mallakpour,et al.  Novel, thermally stable and chiral poly(amide-imide)s derived from a new diamine containing pyridine ring and various amino acid-based diacids , 2013 .

[5]  S. Mallakpour,et al.  Poly(amide-imide)s obtained from 3,5-diamino-N-(thiazol-2-yl)-benzamide and dicarboxylic acids containing various amino acid units , 2013 .

[6]  Yao Jin-shui.  Synthesis of Optically Active Poly(amide-imide) in Ionic Liquid , 2013 .

[7]  M. Sabzalian,et al.  Novel Bioactive Chiral Poly(amide–imide)s Containing Different Amino Acids Linkages: Studies on Synthesis, Characterization and Biodegradability , 2013, Journal of Polymers and the Environment.

[8]  Rong-Hsien Lin,et al.  Preparation and characterization of biodegradable condensation polyimide , 2012 .

[9]  K. Faghihi,et al.  Synthesis and characterization of optically active poly(amide-imide)s based on [N,N′-(4,4′-carbonyldiphtaloyl)-bis-lamino diacid]s and 1,5-bis(4-aminophenyl)penta-1,4-dien-3-one , 2012, Chinese Journal of Polymer Science.

[10]  Y. Guvenilir,et al.  Biodegradation and Characterization Studies of Different Kinds of Polyurethanes with Several Enzyme Solutions , 2012 .

[11]  M. Sabzalian,et al.  Synthesis, characterization and in vitro antimicrobial and biodegradability study of pseudo-poly(amino acid)s derived from N,N′-(pyromellitoyl)-bis-l-tyrosine dimethyl ester as a chiral bioactive diphenolic monomer , 2011, Amino Acids.

[12]  Hossein Behniafar,et al.  Heat stable and organosoluble polyimides containing laterally-attached phenoxy phenylene groups , 2010 .

[13]  M. Shabanian,et al.  Photosensitive and Optically Active Poly(amide-imide)s Based on N,N- (pyromellitoyl)-bis-L-amino acid and Dibenzalacetone Moiety in the Main Chain: Synthesis and Characterization , 2009 .

[14]  A. Ruoho,et al.  Synthesis and Characterization of Novel Poly(hydrazide-imide)s incorporating L-Alanine , 2009 .

[15]  S. Mallakpour,et al.  Synthesis and characterization of new optically active polyesters by step‐growth polymerization of novel aromatic (2S)‐4‐[(4‐methyl‐2‐phthalimidyl‐pentanoylamino)benzoylamino]isophthalic acid with aromatic diols , 2008 .

[16]  A. Hajipour,et al.  Optically active poly(ester-imide): synthesis and characterization of new optically active poly(ester-imide) thermoplastic elastomers , 2008 .

[17]  T. Matsuura,et al.  Investigation of the fundamental differences between polyamide-imide (PAI) and polyetherimide (PEI) membranes for isopropanol dehydration via pervaporation , 2008 .

[18]  K. Faghihi,et al.  New polyamides based on 2,5‐bis[(4‐carboxyanilino) carbonyl] pyridine and aromatic diamines: Synthesis and characterization , 2008 .

[19]  S. Mallakpour,et al.  Synthesis, Characterization and Properties of a Series of Copoly(amide-imide-ether-urethane)s with a New Hard Segment Constituent: Study of the Effect of Hard Segment Content , 2008 .

[20]  Jui‐Hsiang Liu,et al.  Synthesis and characterization of novel thermally stable and optically active poly(amide‐imide)s derived from N,N′‐(4,4′‐diphthaloyl)‐bis‐L‐leucine diacid and aromatic diamines , 2007 .

[21]  S. Goh,et al.  Miscibility study of Torlon® polyamide-imide with Matrimid® 5218 polyimide and polybenzimidazole , 2007 .

[22]  Jui‐Hsiang Liu,et al.  Novel thermally stable and chiral poly(amide-imide)s bearing from N,N′-(4,4′-diphthaloyl)-bis-l-isoleucine diacid: Synthesis and characterization , 2007 .

[23]  G. Adamus,et al.  Environmental degradation of polyester blends containing atactic poly(3-hydroxybutyrate). Biodegradation in soil and ecotoxicological impact. , 2006, Biomacromolecules.

[24]  E. Kowsari,et al.  Synthesis of novel optically active poly(ester imide)s by direct polycondensation reaction promoted by tosyl chloride in pyridine in the presence of N,N-dimethyformamide , 2006 .

[25]  Yu-Yang Su,et al.  Syntheses and properties of fluorinated polyamides and poly(amide imide)s based on 9,9-bis[4-(4-amino-2-trifluromethylphenoxy)phenyl]fluroene, aromatic dicarboxylic acids, and various monotrimellitimides and bistrimellitimides , 2006 .

[26]  J. McMullin,et al.  Polyamide-imide polymer thin films for integrated optics , 2004 .

[27]  M. Hajibeygi,et al.  Synthesis and properties of new poly(amide imide)s containing Trimellitic rings and hydantoin moieties in the main chain under microwave irradiation , 2004 .

[28]  G. Robertson,et al.  Structural determination of Torlon® 4000T polyamide–imide by NMR spectroscopy , 2004 .

[29]  L. Cianga.  Synthesis and characterization of optically active polymers containing azo groups and (l)-α-amino acid moieties , 2003 .

[30]  J. Fisher,et al.  Photoinitiated cross-linking of the biodegradable polyester poly(propylene fumarate). Part II. In vitro degradation. , 2003, Biomacromolecules.

[31]  C. Ambrose,et al.  In vitro degradation of polymeric networks of poly(propylene fumarate) and the crosslinking macromer poly(propylene fumarate)-diacrylate. , 2003, Biomaterials.

[32]  H. Lee,et al.  Glucose effect on the biodegradation of plastics by compost from food garbage , 2002 .

[33]  Jürgen K. Friedel,et al.  Review of mechanisms and quantification of priming effects. , 2000 .

[34]  E. Yashima,et al.  Polysaccharide Derivatives for Chromatographic Separation of Enantiomers , 1998 .

[35]  R. Gross,et al.  Composting studies of poly (β-hydroxybutyrate-co-/gb-hydroxyvalerate) , 1996 .

[36]  D. Fritsch,et al.  Novel highly permselective 6F-poly(amide-imide)s as membrane host for nano-sized catalysts , 1995 .