Synthetic polyhydroxypolyamides from galactaric, xylaric, D‐glucaric, and D‐mannaric acids and alkylenediamine monomers—some comparisons

The condensation polymerization in a methanol solution of four different esterified aldaric acids (D-glucaric, meso-xylaric, meso-galactaric, and D-mannaric) with even-numbered alkylenediamines (C2–C12) gave polyhydroxypolyamides whose water solubilities and melting points were compared. In general, an increase in the alkylenediamine monomer length resulted in decreased polyamide water solubility. Differences in the polymer melting points and water solubilities were linked primarily to conformational differences of the monomer aldaryl units; for example, polyamides from meso-galactaric acid with an extended zigzag conformation aldaryl monomer unit had higher melting points and lower water solubilities than those from D-glucaric and meso-xylaric acids. The latter acid monomer units tended toward bent conformations that served to diminish intermolecular attractive forces between polymer chains, affecting polymer solubility and melting characteristics. © 2000 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 38: 594–603, 2000

[1]  D. Kiely,et al.  SYNTHESIS OF STEREOREGULAR HEAD,TAIL HYDROXYLATED NYLONS DERIVED FROM D-GLUCOSE , 1996 .

[2]  Alfred D. French,et al.  Computer modeling of carbohydrate molecules , 1990 .

[3]  N. Ogata,et al.  Synthesis of polyamides through active diesters , 1973 .

[4]  Liang Chen,et al.  Hydroxylated nylons based on unprotected esterified D-glucaric acid by simple condensation reactions , 1994 .

[5]  M. Okada,et al.  Macromolecular synthesis from saccharic lactones. Ring‐opening polyaddition of D‐glucaro‐ and D‐mannaro‐1,4:6,3‐dilactones with alkylenediamines , 1993 .

[6]  D. Kiely,et al.  Diborane Reduction of O-(Tert-Butyldimethylsilyi.)galactaramides. A Model Study for Aminoalditol Synthesis , 1986 .

[7]  T. Taga,et al.  Interactions of Calcium Ions with Carbohydrates: X-Ray Diffraction and NMR Spectroscopic Studies on the Potassium Salt and the Calcium Salt of D-Clucaric Acid , 1977 .

[8]  G. A. Jeffrey,et al.  The crystal structure of galactaric acid (mucic acid) at −147°: An unusually dense, hydrogen-bonded structure , 1982 .

[9]  P. Hoagland.  The formation of intermediate lactones during aminolysis of diethyl galactarate , 1981 .

[10]  G. Mcdonald,et al.  The Formation of Intermediate Lactones During Aminolysis of Diethyl Xylarate , 1987 .

[11]  R. Rowland,et al.  Molecular Modeling of Acyclic Carbohydrate DerivativesN,N'-Dimethyl- andN,N'-Dihexylxylaramide: Model Compounds for Synthetic Poly(hexamethylenexylaramide) , 1990 .

[12]  N. Ogata,et al.  Polycondensation reaction of dimethyl tartrate with hexamethylenediamine in the presence of various matrices , 1980 .