Photopolymerization using maleimides as photoinitiators

Hoyle, Charles E.; Clark, Shan C.; Jönsson, Sonny; Shimose, M

doi:10.1016/s0032-3861(97)00181-x

Cited by 74 publications

(51 citation statements)

References 3 publications

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“…7 N-substituted maleimides can thus serve as photoinitiators for the free-radical polymerization and copolymerization of a variety of functional species including acrylate, vinyl ether, and styryloxy monomers. [8][9][10][11][12][13][14][15][16][17] To give one particular example, in the aerospace industry bismaleimides are widely used because of the advantage they offer density wise, while maintaining mechanical properties that are similar to metal alloys. The first step in initiating the free-radical polymerization reaction with these compounds is excitation of the maleimide chromophore.…”

Section: Introductionmentioning

confidence: 99%

Spectroscopy and dynamics of excited states in maleimide and N-methyl maleimide: Ionic projection and ab initio calculations

Steege

Buma

2003

The Journal of Chemical Physics

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The state that is responsible for the strong one-photon absorption around 200 nm in the vapor absorption spectrum of maleimide and N-methyl maleimide has been investigated using excited-state photoelectron spectroscopy in combination with ab initio calculations. The projection of the wave function of the excited state on the ionic manifold done in this way reveals multiple, vibrationally resolved, ionization pathways to ground- and excited states of the radical cation, which provide direct evidence for electronic couplings with other, lower-lying states. From a comparison of the experimental intensity distribution over the ionic vibrational states with ab initio calculated Franck–Condon factors, we are able to elucidate the role of the various electronically excited states in the ionization process. The experiments also provide the first determination of adiabatic ionization energies in the two molecules. For maleimide values of 10.330 and 10.903 eV are found for D0 and D1, respectively; for N-methyl maleimide D0 is found at 9.897 or, in an alternative interpretation of the spectrum, at 9.676 eV. Calculations and experiment demonstrate that in this molecule the ground ionic state changes its character with respect to maleimide from a lone pair to a π orbital ionization.

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Section: Introductionmentioning

confidence: 99%

Spectroscopy and dynamics of excited states in maleimide and N-methyl maleimide: Ionic projection and ab initio calculations

Steege

Buma

2003

The Journal of Chemical Physics

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“…As the unreacted photoinitiator may affect the longterm properties of UV-cured polymers, growing attention has been given to photoinitiator-free formulations undergoing fast polymerisation upon UV exposure. A series of such UV-curable systems consisting of a combination of electron donor and electron acceptor monomers has been recently developed by Jönsson et al [1][2][3][4][5][6] The most thoroughly studied system consists of a stoichiometric mixture of a vinyl ether (VE) monomer (donor) and an Nsubstituted maleimide (MI) monomer (acceptor). The reactivity of some VE/MI based systems was found to be as high as that of the widely used acrylate resins containing a radical-type photoinitiator.…”

Section: Introductionmentioning

confidence: 99%

Light-induced polymerisation of photoinitiator-free vinyl ether/maleimide systems

Decker¹,

Morel

Jönsson

et al. 1999

Macromol. Chem. Phys.

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SUMMARY: The photo-induced copolymerisation of electron donor/electron acceptor monomers has been studied by real-time infrared spectroscopy. With stoichiometric maleimide-vinyl ether mixtures, the reaction was found to proceed within seconds upon UV exposure. For systems with an excess of vinyl ether, the two monomers disappeared at essentially the same rate, to generate an alternating copolymer. In such photoinitiator-free systems, the initiating radicals are mainly formed by hydrogen abstraction by the excited maleimide molecules. Highly crosslinked polymer networks have been obtained by light-induced copolymerisation of bismaleimide and divinyl ether monomers. One of the distinct characteristics of this type of radical-induced polymerisation, beside the absence of any added photoinitiator, is that it is less sensitive to oxygen inhibition than the conventional UV-curable acrylate resins.

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“…30 Many studies showed that the maleimide groups can initiate a photopolymerization reaction. [31][32][33][34] Two mechanisms of photoinitiation were proposed for the acceptor/donor systems like maleimide/vinyl ether. For the first one, the excitation of the maleimide functions by UV radiation allows to extract protons by intra-or intermolecular mechanism which gives the photoinitiation step.…”

Section: Study By Ft-ir Spectroscopy Of the Maleimideterminated Oligomentioning

confidence: 99%

“…31 Moreover, this study confirmed that aliphatic maleimide-terminated oligomers allow the photoinitiation of the reaction. According to Morel et al, 29,35 the maleimide compounds can generate radicals by extraction of labile hydrogen atoms when they are in an excited state under the action of UV radiation 10,29,32,36 (Scheme 7).…”

Section: Study By Ft-ir Spectroscopy Of the Maleimideterminated Oligomentioning

confidence: 99%

Synthesis of maleimide‐terminated n‐butyl acrylate oligomers by atom transfer radical polymerization: Study of their copolymerization with vinyl ethers

Boyer

Otazaghine

Boutevin

et al. 2005

J. Polym. Sci. A Polym. Chem.

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Photopolymerization using maleimides as photoinitiators

Cited by 74 publications

References 3 publications

Spectroscopy and dynamics of excited states in maleimide and N-methyl maleimide: Ionic projection and ab initio calculations

Spectroscopy and dynamics of excited states in maleimide and N-methyl maleimide: Ionic projection and ab initio calculations

Light-induced polymerisation of photoinitiator-free vinyl ether/maleimide systems

Synthesis of maleimide‐terminated n‐butyl acrylate oligomers by atom transfer radical polymerization: Study of their copolymerization with vinyl ethers

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