Low migration type I photoinitiators for biocompatible thiol-ene formulations
[Display omitted] •Polymerizable type I photoinitators were synthesized.•A monoacylphosphine oxides bearing an alkyne group feature high photoactivity.•Covalent immobilization of photoinitiators significantly reduces migration. In this contribution, polymerizable hydroxyalkyl phenone (PI-4) and mono...
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| Published in: | European polymer journal Vol. 88; pp. 393 - 402 |
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| Main Authors: | , , , , , , |
| Format: | Journal Article |
| Language: | English |
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01-03-2017
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| Abstract | [Display omitted]
•Polymerizable type I photoinitators were synthesized.•A monoacylphosphine oxides bearing an alkyne group feature high photoactivity.•Covalent immobilization of photoinitiators significantly reduces migration.
In this contribution, polymerizable hydroxyalkyl phenone (PI-4) and monoacylphosphine oxide (PI-9) based photoinitiators (PIs) bearing alkyne groups were synthesized with the aim to realize low PI migration together with a high photoactivity in biocompatible vinyl carbonate/thiol resins. Although, photo-DSC measurements showed that the initiation performance of PI-4 in the present formulation is lower than the photoactivity of the reference PI Irgacure 2959 (I2959), it turned out that its migration is significantly reduced compared to I2959. This fact is explained by the copolymerization of the alkyne functionality via a thiol/yne reaction as revealed by real-time FT-IR measurements, leading to a covalent immobilization of this PI in the polymeric network. Most importantly, the alkyne functionalized monoacylphosphine oxide based PI provides almost similar initiation activity as its reference PI Irgacure TPO-L (TPO-L) while exhibiting 40% lower migration than the non-functionalized TPO-L. These findings make PI-4 and PI-9 promising candidates for their application in biocompatible vinyl carbonate/thiol formulations, in which low migration of the PI is desired. |
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| AbstractList | In this contribution, polymerizable hydroxyalkyl phenone (PI-4) and monoacylphosphine oxide (PI-9) based photoinitiators (PIs) bearing alkyne groups were synthesized with the aim to realize low PI migration together with a high photoactivity in biocompatible vinyl carbonate/thiol resins. Although, photo-DSC measurements showed that the initiation performance of PI-4 in the present formulation is lower than the photoactivity of the reference PI Irgacure 2959 (I2959), it turned out that its migration is significantly reduced compared to I2959. This fact is explained by the copolymerization of the alkyne functionality via a thiol/yne reaction as revealed by real-time FT-IR measurements, leading to a covalent immobilization of this PI in the polymeric network. Most importantly, the alkyne functionalized monoacylphosphine oxide based PI provides almost similar initiation activity as its reference PI Irgacure TPO-L (TPO-L) while exhibiting 40% lower migration than the non-functionalized TPO-L. These findings make PI-4 and PI-9 promising candidates for their application in biocompatible vinyl carbonate/thiol formulations, in which low migration of the PI is desired. [Display omitted] •Polymerizable type I photoinitators were synthesized.•A monoacylphosphine oxides bearing an alkyne group feature high photoactivity.•Covalent immobilization of photoinitiators significantly reduces migration. In this contribution, polymerizable hydroxyalkyl phenone (PI-4) and monoacylphosphine oxide (PI-9) based photoinitiators (PIs) bearing alkyne groups were synthesized with the aim to realize low PI migration together with a high photoactivity in biocompatible vinyl carbonate/thiol resins. Although, photo-DSC measurements showed that the initiation performance of PI-4 in the present formulation is lower than the photoactivity of the reference PI Irgacure 2959 (I2959), it turned out that its migration is significantly reduced compared to I2959. This fact is explained by the copolymerization of the alkyne functionality via a thiol/yne reaction as revealed by real-time FT-IR measurements, leading to a covalent immobilization of this PI in the polymeric network. Most importantly, the alkyne functionalized monoacylphosphine oxide based PI provides almost similar initiation activity as its reference PI Irgacure TPO-L (TPO-L) while exhibiting 40% lower migration than the non-functionalized TPO-L. These findings make PI-4 and PI-9 promising candidates for their application in biocompatible vinyl carbonate/thiol formulations, in which low migration of the PI is desired. |
| Author | Oesterreicher, Andreas Edler, Matthias Griesser, Thomas Hennen, Daniel Mostegel, Florian H. Roth, Meinhart Kappaun, Stefan |
| Author_xml | – sequence: 1 givenname: Andreas surname: Oesterreicher fullname: Oesterreicher, Andreas organization: Chair of Chemistry of Polymeric Materials & Christian Doppler Laboratory for Functional and Polymer Based Ink-Jet Inks, University of Leoben, Otto-Glöckel-Strasse 2, A-8700 Leoben, Austria – sequence: 2 givenname: Meinhart surname: Roth fullname: Roth, Meinhart organization: Chair of Chemistry of Polymeric Materials & Christian Doppler Laboratory for Functional and Polymer Based Ink-Jet Inks, University of Leoben, Otto-Glöckel-Strasse 2, A-8700 Leoben, Austria – sequence: 3 givenname: Daniel surname: Hennen fullname: Hennen, Daniel organization: Chair of Chemistry of Polymeric Materials & Christian Doppler Laboratory for Functional and Polymer Based Ink-Jet Inks, University of Leoben, Otto-Glöckel-Strasse 2, A-8700 Leoben, Austria – sequence: 4 givenname: Florian H. surname: Mostegel fullname: Mostegel, Florian H. organization: Chair of Chemistry of Polymeric Materials & Christian Doppler Laboratory for Functional and Polymer Based Ink-Jet Inks, University of Leoben, Otto-Glöckel-Strasse 2, A-8700 Leoben, Austria – sequence: 5 givenname: Matthias surname: Edler fullname: Edler, Matthias organization: Chair of Chemistry of Polymeric Materials & Christian Doppler Laboratory for Functional and Polymer Based Ink-Jet Inks, University of Leoben, Otto-Glöckel-Strasse 2, A-8700 Leoben, Austria – sequence: 6 givenname: Stefan surname: Kappaun fullname: Kappaun, Stefan organization: Durst Phototechnik DIT, Julius-Durst-Strasse 11, A-9900 Lienz, Austria – sequence: 7 givenname: Thomas surname: Griesser fullname: Griesser, Thomas email: thomas.griesser@unileoben.ac.at organization: Chair of Chemistry of Polymeric Materials & Christian Doppler Laboratory for Functional and Polymer Based Ink-Jet Inks, University of Leoben, Otto-Glöckel-Strasse 2, A-8700 Leoben, Austria |
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•Polymerizable type I photoinitators were synthesized.•A monoacylphosphine oxides bearing an alkyne group feature high... In this contribution, polymerizable hydroxyalkyl phenone (PI-4) and monoacylphosphine oxide (PI-9) based photoinitiators (PIs) bearing alkyne groups were... |
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| SubjectTerms | Alkynes Biocompatibility Copolymerization Covalence Formulations Low-migration Migration Photoinitiator Photoinitiators Polyimide resins Polymerization Polymers Resins Thiol-ene |
| Title | Low migration type I photoinitiators for biocompatible thiol-ene formulations |
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