Synthesis and Characterization of Bis(2-hydroxypropyl)amide-Based Hyperbranched Polyesteramides

Abstract

Polycondensation of 1,2-cyclohexane dicarboxylic anhydride with a calculated molar excess of di-2-propanolamine led to bis(2-hydroxyalkyl)amide based hydroxy-functional hyperbranched polyesteramides in a straightforward manner. Modification reactions of these polymers with lauric esters was conducted in different synthetic approaches. The obtained polymers were characterized by mass spectrometry, using electrospray ionization (ESI) and matrix assisted laser desorption ionization/timeof-flight (MALDI-TOF) techniques, and by size exclusion chromatography in combination with on-line viscosimetry detection (SEC-DV). Comparison of the experimental results with theoretical calculations showed a satisfactory match on molecular weights and polydispersities with fully modified polyesteramides. These values were found to deviate with unmodified and, to a smaller extent, with partially modified polyesteramides. This phenomenon could be attributed to side reactions of the 2-hydroxypropylamide end groups. The lauric ester modified polyesteramides obtained from either consecutive or simultaneous polycondensation and lauric acid esterification were found to be quite similar in structure and molecular weight distribution. This observation underlined the influence of transesterification reactions under the applied conditions.

Structural analysis of the curing of epoxy thermosets crosslinked with hyperbranched poly(ethyleneimine)s

“…Random statistical procedures are commonly used to study the structure of hyperbranched polymers, but a series of deviations from the ideal situation are expected due to subsitution effects during polymerization, the occurrence of side reactions and intramolecular cyclization [18][19][20][21][22][23][24][25]. The high mass-average molecular weight and polymer dispersity of the resulting polymes can be controlled by means of the addition of small core molecules [18,19,26], a feature that can be easily incorporated into statistical models.…”

Dielectric Properties of Hyperbranched Polyesteramide with Long Alkyl Chain End Groups

“…The method was described by Froeling [21] who and his group synthesized series of hyperbranched polyester amides using different acid anhydrides as A 2 monomers and diisopropanol amine as B 0 B 2 . It is known that DEA is not the best candidate to be used as B 0 B 2 monomer since the presence of primary OH group leads to gelation through the undesired side product from the reaction of the OH group instead of the amine group.…”

Development of DSM's hybrane® hyperbranched polyesteramides

“…Combined with the application of mathematical models, the results of the analytical work confirmed that the ideas of the chemists indeed gave full control over the structures as described above. We published the work in the form of two extensive articles, 11,12 which unexpectedly also yielded us the annual DSM Publication Award (Fig. 6).…”