One‐step synthesis of functional polymers by polycondensation: Polyesters with pendant hydroxyl side groups from potassium malate or tartrate and 1,4‐dibromobutane

Abstract

Polyesters with pendant hydroxyl side groups such as (R,S)and (S)-poly(tetramethy1ene ma1ate)s and (R,R)-poly(tetramethy1ene tartrate)s of moderately high molecular weights were prepared by polycondensation, at 105 "C in 1-methyl-2-pyrrolidone for 16 to 80 h, from potassium malate or tartrate and 1,4-dibromobutane. It was shown by a detailed analysis of the 'H and 13C NMR spectra of the prepared polyesters that no branching occurs in the course of the reaction. The nature of the end-groups was also clearly established by NMR spectroscopy. The presence of large cycles in the final products cannot be completely excluded.0 1993, Huthig & Wepf Verlag, Base1 CCC 0025-1 16X/93/$05.00

Novel Bioerodible Poly(hydroxyalkylene carbonates)s: A Versatile Class of Polymers for Medical and Pharmaceutical Applications

“…11.8 Hz and J = ca. 3.3 Hz, 2 H, 2 Ha of 2 CH2), 5.339 (m, 2 H, 2 CH). 13C NMR (CDC13): ó 169.82 (-C(O)-O), 154.22 (O-C(O)-O), 68.68 (CH), 65.67 (CH2), 20.66 (CH3).…”

“…NMR (CDCls): <5 0.88 (t, J = ca. 7 Hz, CH3), 1.00-1.35 (m, CH2), 1.61 (m, CH2), 2.34 (m, CH2), 4.14 (m, 2 H, 2 Hb of 2 CH2-0 of diunits), 4.363 (m, 2 H, 2 Ha of 2 CH2-0 of diunits), 4.0-4.5 (m, CH-O and CH2-0 of monounits), 5.20 (m, 1 CH of monounits), 5.34 (m, 2 CH of diunits).…”

“…7 Hz, 6 H, 2 CH3), 4.346 (q, V = ca. 7 Hz, 4 H, 2 side chain CH2), 4.295-4.410 (m, 2 H, 2 Hb of 2 CH2), 4.475-4.575 (m, 2 H, 2 HA of 2 CH2), 5.522 (m, 2 H, 2 CH). 13C NMR (CDC13): ó 156.69 (-C(O)-O), 156.59 (-C(O)-O), 153.88 (O-C(O)-O), 71.09 (CH), 65.01 (CH2), 63.48 (CH2), 13.84 (CH3).…”

Synthesis and characterization of functional aliphatic copolyesters

“…Polymers obtained by the transesterification16 or polymerization of cyclic carbonate with protected pendant hydroxyl groups17 or by the copolymerization of acid anhydrides with oxiranes carrying substituents containing protected hydroxyl groups18 or with allyl glycidyl ether19 have been reported in the literature. The reaction of 1,4‐dibromobutane with potassium salts of tartaric or malic acids also has been reported 20. A series of polyfunctional carboxyl telechelic microspheres with different lengths and numbers of oligocaprolactone telechelic branch chains, which were capped with two (or three) carboxyl groups at one of the telechelic chain extremities, were synthesized by a hydroxy acid [ D,L ‐malic acid or citric acid (CA)] ‐initiated polymerization of caprolactone 21.…”

Preliminary Studies on the Hydrolytic Degradation and Biocompatibility of Poly(3-allyloxy-1,2-propylene succinate)

“…Pendant functionality in polyesters creates an interesting perspective for chemical coupling of drugs or other purposes, but makes their synthesis more complex [3][4][5]. This problem can be solved by using reagents with dormant functional groups, which are not reactive during the synthesis of polyesters.…”