ACTIVE‐BAPO – A Versatile Transfer Agent for Photoactive Bis(acyl)phosphane Oxide Units

Author:

Widera Anna1ORCID,Conti Riccardo1ORCID,Cosola Andrea23ORCID,Fäh Ashling1,Thöny Debora1ORCID,Sangermano Marco2ORCID,Levalois‐Grützmacher Joëlle1ORCID,Grützmacher Hansjörg1ORCID

Affiliation:

1. Department of Chemistry and Applied Biosciences ETH Zürich Vladimir-Prelog-Weg 1–5/10 8093 Zürich Switzerland

2. Department of Applied Science and Technology Politecnico di Torino Corso Duca degli Abruzzi 24 10124 Torino Italy

3. Laboratoire des Solides Irradiés (LSI) CEA/DRF/IRAMIS École Polytechnique Route de Saclay Palaiseau 91128 France

Abstract

AbstractA N‐hydroxy succinimide (NHS) ester substituted bis(acyl)phosphane oxide (ACTIVE‐BAPO) was prepared by phospha‐Michael addition and used for an easy one‐step BAPO ligation with substrates containing primary amino groups, such as amino acids, proteins, and poly(amidoamine) (PAMAM) dendrimers. Thereby, a range of new molecular and polymeric photoinitators was obtained. Real‐time photo‐rheology experiments demonstrated the outstanding efficiency of the PAMAM BAPOs as photoinitiators for free radical polymerization. Remarkably, it is found that PAMAM BAPOs also act as crosslinking agents to convert monofunctional methacrylate monomers into thermosetting networks without any further additives. Depending on the number of the attached BAPOs, thermosets with a different degree of crosslinking and swelling capability in water were obtained.

Funder

Deutsche Forschungsgemeinschaft

Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung

Eidgenössische Technische Hochschule Zürich

Publisher

Wiley

Subject

General Chemistry,Catalysis,Organic Chemistry

Reference38 articles.

1. K. Dietliker A Compilation of Photoinitiators Commercially Available for UV Today SITA Technology Ltd London UK 2002.

2. J. V. Crivello K. Dietliker Photoinitiators for Free Radical Cationic & Anionic Photopolymerization Wiley 2nded. 1999 Vol. 168.

3. Novel Synthetic Pathways for Bis(acyl)phosphine Oxide Photoinitiators

4. Neue Synthesewege für Bisacylphosphinoxid-Photoinitiatoren

5. A Simple Straightforward Synthesis of Phenylphosphane and the Photoinitiator Bis(mesitoyl)phenylphosphane Oxide (IRGACURE 819)

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