Team:TU Darmstadt/Project/Chem

Introduction

This part is the link between our Biological work and the 3D printer. After we have produced our monomer molecules in E. coli and purified them subsequently, they need to be connected to short polymers, the prepolymers. Those fluid prepolymers are used in our 3D printer as a resin, the basis from which the final and hardened 3D structures emerge.

We used different monomers in varying proportions for produce the prepolymers. We’d be able to create a lot of alternative prepolymers with different physical properties. Those could be utilized to adjust the physical properties of the final polymers.

Schematic overview

Itaconic acid (IA)

This is the crucial monomer, because it is photoactive. It contains a carbon double bond that undergoes the light-initiated crosslinking during the final printing process. The other important chemical functions are the two acid groups at the ends of the molecule. In the chemical generation of the prepolymer they react with the alcohol groups of the other monomers in an esterification reaction and water is released.

Ethylene glycol (EG) / Polyethylene glycol (PEG)

Ethylene glycol is the basic provider of alcohol groups for the esterification reaction. It also serves as a spacer to increase the distance between the itaconic acid molecules in the prepolymer. By changing the distance between the photoactive compounds it is possible to adapt the density of light-initiated crosslinking and thus the physical properties of the final polymer. For this reason we also used polyethylene glycol of different length to increase the coverage of our spacer.

EG/PEG have two terminal alcohol groups and itaconic acid has to terminal acid groups. They can be connected to polymers which do not possess side chains. This makes the adjustment of the reaction and the determination of the prepolymer rather easy, but it also means that only the length of the chains can be adapted.

Xylitol

In order to get a broader scope of different possible prepolymers we decided to use xylitol as an additional compound in our preploymer. Besides its two terminal it contains three additional alcohol groups. It can react with more than two itaconic acid molecules and thus induce further crosslinking additionally to the light-initiated crosslinking in the printing process afterwards. By using different proportions between (P)EG and xylitol the density of this crosslinking step can be adapted.

Procedure

During the experiments we designed our own test procedure. To our surprise we were able to produce polymers under much easier reaction conditions than in the literature [Referenz]. In contrast to literature data we didn’t use vacuum and an argon atmosphere to get comparable polymers. This procedure was used for all of our following experiments (please see the material and methods part for further details).

1. Pre-dried (water free) monomers were mixed: