Synthesis and properties of coumaric acid derivative homo-polymers.
Poly(4-hydroxycinnamic acid) (P4HCA), poly(3-hydroxycinnamic acid) (P3HCA), poly(3-methoxy-4-hydroxycinnamic acid) (PMHCA) and poly(3,4-dihydroxycinnamic acid) (PDHCA) were synthesized by the thermal poly-condensation of the corresponding monomers, which are lignin precursors, coumaric acid derivatives consisting of cinnamoyl groups and different position and number of OH groups. The solubility of the homo-polymers in organic solvents decreased in the order of P3HCA > PDHCA > P4HCA > PMHCA. The wide angle X-ray diffraction (WAXD) results indicated that P4HCA or PMHCA with p-OH group had higher crystallinity, in contrast to P3HCA or PDHCA with m-OH group which had lower crystallinity. Crossed-polarizing microscopy suggested that P4HCA had the nematic liquid crystal properties at 220 degrees C and PDHCA showed birefringence properties at 200 degrees C. In cell-adhesion tests, PDHCA showed the highest cell adhesion (ca. 70%), whereas P3HCA, P4HCA and PMHCA had 50, 18 and 10% cell adhesion, respectively. The coumaric acid derivative homo-polymers can be useful as cell adhesion controllable thermotropic polymers for biomedical and environmental fields.
Thi
Tran Hang
TH
Faculty of Technology of Organic Chemistry, College of Chemistry, Ministry of Industry, Tien Kien, Lam Thao, Phu Tho, Vietnam.
Matsusaki
Michiya
M
Shi
Dongjian
D
Kaneko
Tatsuo
T
Akashi
Mitsuru
M
D000818:Animals; D002109:Caffeic Acids / Q000737:chemistry; D002448:Cell Adhesion; D002460:Cell Line; D003373:Coumaric Acids / Q000737:chemistry*; D005347:Fibroblasts / Q000166:cytology; D050866:Liquid Crystals / Q000737:chemistry; D051379:Mice; D008859:Microscopy, Polarization; D015394:Molecular Structure; D008970:Molecular Weight; D011108:Polymers / Q000138:chemical synthesis / Q000737:chemistry*; D011422:Propionates; D012995:Solubility; D012997:Solvents / Q000737:chemistry; D017550:Spectroscopy, Fourier Transform Infrared; D054457:Tissue Scaffolds / Q000737:chemistry; D014961:X-Ray Diffraction
D002109:Caffeic Acids; D003373:Coumaric Acids; D011108:Polymers; D011422:Propionates; D012997:Solvents; C004999:ferulic acid; C495469:p-coumaric acid; C040048:caffeic acid