Research data for "Bridging the gap between performance and biocompatibility: non-toxic, multifunctional aliphatic photoinitiators based on α-ketoesters for lithography-based manufacturing applications"

Context

This dataset was created from original work conducted in the framework of a PhD project and compiled in a publication ("Bridging the gap between performance and biocompatibility: non-toxic, multifunctional aliphatic photoinitiators based on α-ketoesters for lithography-based manufacturing applications"). It provides the raw data of the results presented and discussed therein.

Technical details

Microsoft Excel file “Raw Data_Photoinitiators”:

Tab 1 - Raw Data obtained for UV Vis measurements (KE1-4, BP)

Tab 2 – Evaluated Data obtained for Photo-DSC measurements of KE1-4 and BP+MDEA in various monomers using a 320-500 nm broadband UV lamp

Tab 3 – Evaluated Data obtained for Photo-DSC measurements of KE3 and co-initiators in various monomers using a 320-500 nm broadband UV lamp

Tab 4 – Evaluated Data obtained for Photo-DSC measurements of KE1-4 and BP+MDEA in various monomers using a 385 nm LED

Tab 5 – Raw Data obtained for Presto Blue Assay

Tab 6 – Raw Data obtained for Presto Blue Assay – Detailed evaluation of the cytotoxicity tests

Tab 7 – Raw Data of Plate Reader for Presto Blue Assay

Tab 8 – Raw Data obtained for the GPC measurements of KE4 and ethoxylated pentaerythritol

Tab 9 – Raw Data obtained for Photo-DSC measurements of KE1-4 and BP+MDEA in various monomers using a 320-500 nm broadband UV lamp

Tab 10 – Raw Data obtained for Photo-DSC measurements of KE3 and co-initiators in various monomers using a 320-500 nm broadband UV lamp

Tab 11 - Raw Data obtained for Photo-DSC measurements of KE1-4 and BP+MDEA in various monomers using a 385 nm LED

Tab 12 - Raw Data obtained for UV Vis measurements of IC2959

Tab 13 - Raw Data obtained for Photo-DSC measurements of KE3 and BP+MDEA in JRNIL cure and M286 resins

Tab 14 - Raw Data obtained for RT-NIR measurements of KE1-3, BP+MDEA and IC2959 in various monomers using a 320-500 nm broadband UV lamp

NMR file

‘1H KE2, ‘13C KE2', ‘1H KE3’, ‘13C KE3’ and ‘1H KE4’ folders:

NMR data obtained during all synthesis steps of KE2, KE3 and KE4.

A software to display NMR-spectra is needed, such as MestreNova or Topspin.

Compound descriptions

Compound descriptions in the files included herein adhere to the naming in the related publication referenced in the Related Works section, where all compounds are described in detail and drawn as structural formulas. In brief:

KE1: Ethyl pyruvate

KE2: 2-(Acetylcarbonyloxy)ethyl pyruvate

KE3: 2,2-Bis[(acetylcarbonyloxy)methyl]butyl pyruvate

KE4: Ethoxylated pentaerythritol tetrapyruvate

BP: Benzophenone

MDEA: Methyldiethanolamine

HDDA: Hexanedioldiacrylate

DMM: Dimethacrylate mixture (equimolar mixture of urethanedimethacrylate UDMA and decandioldimethacrylate D3MA)

PEGDA: Poly(ethylene glycol) diacrylate Mw ~700 g/mol, 50 wt% in water

EDB: Ethyl 4-dimethylaminobenzoate

PEG: Poly(ethylene glycol)

PPG: Poly(propylene glycol)

IC/IC2959: Irgacure 2959

Li-TPO: Lithium-phenyl-2,4,6-trimethylbenzoylphosphinat

DMEM: Dulbecco's Modified Eagle’s medium

FBS: Fetal bovine serum

JRNIL cure: Decandiol diacrylat

M286: Poly(ethylene glycol) diacrylate Mw ~700 g/mol, 50 wt% in water

Abstract (English)

Photoinitiators (PIs) represent the key molecules within a photopolymerizable resin, due to their ability to generate the initiating species. However, the majority of state-of-the-art PIs comprise aromatic chromophores, known to produce cytotoxic photoproducts, whose migration out of the cured resin poses both environmental and human health threats. Herein, we present a set of multifunctional, aliphatic free radical photoinitiators based on the α-ketoester moiety, which exhibit low cytotoxicity even after irradiation. By systematically increasing the number of PI moieties, purely aliphatic molecules comprised of up to four radical-generating units have been synthesized. High miscibility in both organic and water-based formulations, combined with excellent photoreactivity and no discoloration upon irradiation with broadband (320-500 nm) and LED (385 nm) light sources, are demonstrated. The developed α-ketoester derivatives outperform the benchmark Norrish Type II benzophenone/amine system and can be used for advanced applications, including UV-nanoimprint lithography as well as additive manufacturing technologies (DLP 3D printing).