Synthesis of Poly(galactaramides) from Alkylene- and Substituted Alkylenediammonium Galactarates

REFERENCES

• Ogata , N. and Hosoda , Y. 1974 . Synthesis of hydrophilic polyamide by active polycondensation . J. Polym. Sci. Polym. Lett. , 12 : 355 – 358 .
   Web of Science ®Google Scholar
• Ogata , N. and Hosoda , Y. 1975 . Synthesis of hydrophilic polyamide from l-tartarate and diamines by active polycondensation . J. Polym. Sci. Part A Polym. Chem. , 13 : 1793 – 1801 .
   Web of Science ®Google Scholar
• Ogata , N. , Sanui , K. , Hosoda , Y. and Nakamura , H. 1976 . Active polycondensation of diethyl 2,3,4,5-tetrahydroxyadipate with diamines . J. Polym. Sci. Part A Polym. Chem. , 14 : 783 – 792 .
   Web of Science ®Google Scholar
• Ogata , N. and Sanui , K. 1977 . Copolymerization of hydroxyl diesters and active diesters with hexamethylenediamine . J. Polym. Sci. Part A Polym. Chem. , 15 : 1523 – 1526 .
   Web of Science ®Google Scholar
• Ogata , N. , Sanui , K. and Iijima , K. 1973 . Synthesis of polyamides through active diesters . J. Polym. Sci. Part A Polym. Chem. , 11 : 1095 – 1105 .
   Google Scholar
• Ogata , N. and Okamoto , S. 1973 . Synthesis of polyesters from active diesters . J. Polym. Sci. Part A Polym. Chem. , 11 : 2537 – 2545 .
   Web of Science ®Google Scholar
• Ogata , N. 1976 . New polycondensation systems . Polym. Prepr. , 17 : 151 – 156 .
   Google Scholar
• Ogata , N. , Sanui , K. , Nakamura , H. and Kuwahara , M. 1980 . Polycondensation reaction of dimethyl tartrate with hexamethylenediamine in the presence of various matrices . J. Polym. Sci. Part A Polym. Chem. , 18 : 939 – 948 .
   Web of Science ®Google Scholar
• Hoagland , P. D. 1981 . The formation of intermediate lactones during aminolysis of diethyl galactarate . Carbohydr. Res. , 98 : 203 – 208 .
   Web of Science ®Google Scholar
• Hoagland , P. D. , Pessen , H. and McDonald , G. G. 1987 . The formation of intermediate lactones during aminolysis of diethyl xylarate . J. Carbohydr. Chem. , 6 : 495 – 499 .
   Web of Science ®Google Scholar
• Hashimoto , K. , Okada , M. and Honjou , N. 1990 . Ring-opening polyaddition of d-glucaro-1,4:6,3-dilactone with p-xylylenediamine . Makromol. Rapid Commun. , 11 : 393 – 396 .
   Google Scholar
• Hashimoto , K. , Wibullucksanakul , S. , Matsuura , M. and Okada , M. 1993 . Macromolecular synthesis from saccharic lactones. Ring-opening polyaddition of d-glucaro- and d-mannaro-1,4:6,3-dilactones with alkylenediamines . J. Polym. Sci. Part A Polym. Chem. , 31 : 3141 – 3149 .
   Web of Science ®Google Scholar
• Kiely , D. E. , Chen; , L. and Lin , T-H. 1994 . Hydroxylated nylons based on unprotected esterifed d-glucaric acid by condensation reactions . J. Am. Chem. Soc. , 116 : 571 – 578 .
   Web of Science ®Google Scholar
• Kiely , D. E. , Chen , L. and Lin , T-H. 2000 . Synthetic polyhydroxypolyamides from galactaric, xylaric, d-glucaric and d-mannaric acids and alkylenediamine monomers – some comparisons . J. Polym. Sci. Part A Polym. Chem. , 38 : 594 – 603 .
   Web of Science ®Google Scholar
• Henkensmeier , D. , Abele , B. C. , Candussio , A. and Thiem , J. 2004 . Synthesis, characterization and degradability of polyamides derived from aldaric acids and chain end functionalized polydimethylsiloxanes . Polymer , 45 : 7053 – 7059 .
   Web of Science ®Google Scholar
• Jahns , T. and Kiely , D. E. 2006 . Abiotic hydrolysis of some poly-d-glucaramides and subsequent microbial utilization/degradation . J. Polym. Environ. , 14 : 165 – 169 .
   Web of Science ®Google Scholar
• Kiely , D. E. Carbohydrate acid amide plant fertilizers . U. S. Patent 5,478,374 . December 26, 1995 . CA 1996:56392
   Google Scholar
• Styron , S. B. , French , A. D. , Friedrich , J. D. , Lake , C. and Kiely , D. E. 2002 . MM3(96) Conformational analysis of d-glucaramide and X-ray crystal structure of three d-glucaric acid derivatives – models for synthetic poly(alkylene d-glucaramides) . J. Carbohydr. Chem. , 21 : 27 – 51 .
   Web of Science ®Google Scholar
• Morton , D. W. and Kiely , D. 2000 . Evaluation of the film and adhesive properties of some block copolymer polyhydroxypolyamides from esterified aldaric acids and diamines . J. Appl. Polym. Sci. , 77 : 3085 – 3092 .
   Web of Science ®Google Scholar
• Jeffrey , G. A. and Wood , R. A. 1982 . The crystal structure of galactaric acid (mucic acid) at −147∘C: an unusually dense, hydrogen-bonded structure . Carbohydr. Res. , 108 : 205 – 211 .
   Web of Science ®Google Scholar
• Allcock , H. A. and Lampe , F. W. 1990 . Contemporary Polymer Chemistry, , 2nd Ed. , 25 – 26 . Englewood Cliffs, NJ : Prentice Hall .
   Google Scholar
• Billmeyer , F. W. Jr. 1984 . Textbook of Polymer Science, , 3rd Ed. , 407 – 413 . New York, NY : Wiley-Interscience .
   Google Scholar
• Kiely , D. E. , Kramer , K. and Zhang , J. Method for preparing high molecular weight random polyhydroxypolyamides . U. S. Patent 6,894,135 . May 17, 2005 . CA 2004:515565
   Google Scholar
• Tian , W. , Liao , H. , Wu , J.-G. and Yang , G.-D. 1997 . Study on the coordination of the hydroxyl group: crystal structure and FT-IR spectra of potassium hydrogen galactarate . Polyhedron , 16 : 2955 – 2058 .
   Google Scholar
• Taga , T. , Shimada , T. and Mimura , N. 1994 . Sodium galactarate and potassium galactarate . Acta Crystallogr. Sect. C Cryst. Struct. Commun. , 50 : 1076 – 1079 .
   Google Scholar
• Sheldrick , B. and Mackie , W. 1989 . Magnesium galactarate dihydrate . Acta Crystallogr. Sect. C Cryst. Struct. Commun. , 45 : 1072 – 1073 .
   Google Scholar
• Mackie , W. and Akrigg , D. 1989 . The structures of barium d-galactarate monohydrate and calcium d-galactarate tetrahydrate . Acta Crystallogr. Sect. C Cryst. Struct. Commun. , 45 : 191 – 194 .
   Google Scholar
• Benetollo , F. , Bombieri , G. , Liang , H. , Liao , H. , Shi , N. and Wu , J. 1993 . Structural and spectral studies of ammonium mucicate . Crystallogr. Spectrosc. Res. , 23 : 171 – 175 .
   Google Scholar
• Jarman , B. P. , Kiely , D. E. , Manley-Harris , M. and Nicholson , B. K. 2009 . The structures and hydrogen bonding networks in crystals of alkylenediammonium salts of galactaric acid . J. Carbohydr. Chem. , 28 : 107 – 123 .
   Web of Science ®Google Scholar
• Viswanathan , A. and Kiely , D. E. 2003 . Mechanism for the formation of diamides and polyamides by aminolysis of d-glucaric acid esters . J. Carbohydr. Chem. , 22 : 903 – 918 .
   Web of Science ®Google Scholar
• Chen , L. and Kiely , D. E. 1996 . Synthesis of stereoregular head tail hydroxylated nylons derived from d-glucose . J. Org. Chem. , 61 : 5847 – 5851 .
   Google Scholar
• Jarman , B. 2006 . Synthesis of polyhydroxypolyamides based on galactaric acid and X-ray crystal analysis of their precursors , M.Sc. in Chemistry, Thesis Hamilton, NZ : The University of Waikato .
   Google Scholar
• Morton , D. W. and Kiely , D. E. 2000 . Synthesis of poly(azaalkylene aldaramide)s and poly(oxaalkylene aldaramides) derived from d-glucaric and galactaric acids . J. Polym. Sci. Part A Polym. Chem. , 38 : 604 – 613 .
   Web of Science ®Google Scholar
• Smith , T. N. , Denton , T. T. , Kramer , K. , Zhang , J. and Kiely , D. E. 2007 . Synthesis and characterization of higher molecular weight stereo-random poly(d-glucaramides) from 1:1 alkylenediammonium d-glucarate salt . Abstracts of Papers, 234th ACS National Meeting . August 19–23 2007 , Boston, MA, United States.
   Google Scholar