Mass spectrometric characterization of telechelic prepolymers and addition polymers of DGEBA-aliphatic amines

Abstract

Plasma desorption (PD) mass spectra of high molecular weight addition polymers of 2.2‐bis‐[4‐(2.3‐epoxypropoxy)phenyl]propane (DGEBA) and benzylamine show protonated molecular ions of the intact polymers and oligomer molecules. In the spectrum of a DGEBA/N,N′‐dibenzyl‐5‐oxanonanediamine‐1.9 addition polymer only fragments of the oligomers and a cyclic oligomer are observed. In both polymer spectra there is no indication for side reactions during the addition polymerization such as ether formation. Fast‐atom bombardment (FAB) spectra of telechelic prepolymers having amino end groups show the regular oligomers with increasing degree of polymerization and the expected fragmentation products. Only prepolymers with epoxide end groups contain the regular prepolymers as well as side reaction products which are formed by reactions of the telechelics and DGEBA or by reaction of themselves. © 1996 John Wiley & Sons, Inc.

Customized PEG‐Derived Copolymers for Tissue‐Engineering Applications

“…[31][32][33][34] Thus, PEG-modified surfaces can be used to create long-circulating micelles or other drug vehicles as well as nonfouling coatings, which prevent bacterial growth or cellular adhesion on catheters or medical implants. [35][36][37] Additionally, this shielding effect can be used to create inert polymer surfaces, which can later be modified with appropriate molecular cues (e.g., peptides or proteins) to obtain cell-specific interactions with biomaterials to achieve targeting of micelles and particles with attached peptide sequences. [38] The different terminal functional groups of PEG allow the use of this polymer for copolymerizations and also determine the degradability of the obtained copolymers, because the newly formed chemical bonds determine whether the PEG can be cleaved from the copolymer to allow the release of soluble PEG molecules.…”

“…The compression of the hydrated polymer coils by a protein molecule takes energy to remove bound water molecules and additionally the PEG coil will lose entropy, making the process of protein adsorption extremely unfavorable for thermodynamic reasons 31–34. Thus, PEG‐modified surfaces can be used to create long‐circulating micelles or other drug vehicles as well as nonfouling coatings, which prevent bacterial growth or cellular adhesion on catheters or medical implants 35–37. Additionally, this shielding effect can be used to create inert polymer surfaces, which can later be modified with appropriate molecular cues (e.g., peptides or proteins) to obtain cell‐specific interactions with biomaterials to achieve targeting of micelles and particles with attached peptide sequences 38…”

Matrix‐assisted laser desorption/ionization, fast atom bombardment and plasma desorption mass spectrometry of polyethylene glycol esters of (2‐benzothiazolon‐3‐yl)acetic acid

“…The molecular mass characteristics of PEGs, M n , M w and PDI , before and after esterification (Table 1) were calculated from their molecular cluster ions by MALDI29–34 and FAB35 (Figs 1 and 2). FAB allows such a calculation for PEGs with molecular mass up to 2 × 10 3 .…”

Metal‐template synthesis of cyclic epoxide–amine oligomers: Uncrosslinked epoxide–amine addition polymers, 47

“…It leads to high‐molecular‐weight linear‐addition polymers with molecular weights of 10–20 kD 12–15. As the step‐growth polymerization is always combined with the formation of cyclic oligomers,16 these cyclomers also were observed17, 18 in epoxide–amine addition polymers. The isolation of epoxide–amine cyclomers has been described some years ago.…”