Low migration type I photoinitiators for biocompatible thiol-ene formulations

被引：30

作者：

Oesterreicher, Andreas ^{[1
,2
]}

Roth, Meinhart ^{[1
,2
]}

Hennen, Daniel ^{[1
,2
]}

Mostegel, Florian H. ^{[1
,2
]}

Edler, Matthias ^{[1
,2
]}

Kappaun, Stefan ^{[3
]}

Griesser, Thomas ^{[1
,2
]}

机构：

[1] Univ Leoben, Chair Chem Polymer Mat, Otto Glockel Str 2, A-8700 Leoben, Austria

[2] Univ Leoben, Christian Doppler Lab Funct & Polymer Based Ink J, Otto Glockel Str 2, A-8700 Leoben, Austria

[3] Durst Phototech DIT, Julius Durst Str 11, A-9900 Lienz, Austria

来源：

EUROPEAN POLYMER JOURNAL | 2017年 / 88卷

关键词：

Photoinitiator; Low-migration; Thiol-ene; PHOTOPOLYMERIZATION; STEREOLITHOGRAPHY; TOUGH;

D O I：

10.1016/j.eurpolymj.2016.10.040

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

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 P1-4 in the present formulation is lower than the photoactivity of the reference PI Irgacure 2959 (12959), it turned out that its migration is significantly reduced compared to 12959. 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 migratiori than the nonfunctionalized TPO-L. These findings make P1-4 and P1-9 promising candidates for their application in biocompatible vinyl carbonate/thiol formulations, in which low migration of the PI is desired. (C) 2016 Published by Elsevier Ltd.

引用

页码：393 / 402

页数：10

共 29 条

[1] REVIEW OF THE TOXICITY OF MULTIFUNCTIONAL ACRYLATES [J].

ANDREWS, LS ;

CLARY, JJ .

JOURNAL OF TOXICOLOGY AND ENVIRONMENTAL HEALTH, 1986, 19 (02) :149-164

[2]

[Anonymous], Organic Polymers, Patent No. [GB925117, 925117]

[3] Highly Efficient Water-Soluble Visible Light Photoinitiators [J].

Benedikt, Stephan ;

Wang, Jieping ;

Markovic, Marica ;

Moszner, Norbert ;

Dietliker, Kurt ;

Ovsianikov, Aleksandr ;

Gruetzmacher, Hansjoerg ;

Liska, Robert .

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2016, 54 (04) :473-479

[4] THE FRIES REARRANGEMENT OF PHENYL ISOBUTYRATE [J].

BRIGGS, TI ;

DUTTON, GGS ;

MERLER, E .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1956, 34 (07) :851-855

[5] Use of stereolithography to manufacture critical-sized 3D biodegradable scaffolds for bone ingrowth [J].

Cooke, MN ;

Fisher, JP ;

Dean, D ;

Rimnac, C ;

Mikos, AG .

JOURNAL OF BIOMEDICAL MATERIALS RESEARCH PART B-APPLIED BIOMATERIALS, 2003, 64B (02) :65-69

[6]

Davies W.D., 2001, SURF COAT INT PART B, P169

[7] The persistent radical effect: A principle for selective radical reactions and living radical polymerizations [J].

Fischer, H .

CHEMICAL REVIEWS, 2001, 101 (12) :3581-3610

[8]

Fouassier J.P., 2012, Photoinitiators for Polymer Synthesis: Scope, Reactivity, and Efficiency

[9] RELATIVE NUCLEOPHILIC REACTIVITIES OF AMINO GROUPS AND MERCAPTIDE IONS IN ADDITION REACTIONS WITH ALPHA BETA-UNSATURATED COMPOUNDS [J].

FRIEDMAN, M ;

CAVINS, JF ;

WALL, JS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (16) :3672-&

[10] Rapid formation of regulated methacrylate networks yielding tough materials for lithography-based 3D printing [J].

Gorsche, Christian ;

Seidler, Konstanze ;

Knaack, Patrick ;

Dorfinger, Peter ;

Koch, Thomas ;

Stampfl, Juergen ;

Moszner, Norbert ;

Liska, Robert .

POLYMER CHEMISTRY, 2016, 7 (11) :2009-2014

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