(9-Oxo-9H-fluoren-2-yl)-phenyl-iodonium hexafluoroantimonate(V) – a photoinitiator for the cationic polymerisation of epoxides

Hartwig, Andreas; Harder, A.; Lühring, Andreas; Schröder, Hendrik

doi:10.1016/s0014-3057(00)00252-4

Cited by 44 publications

(24 citation statements)

References 6 publications

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“…Several attempts have also been made for the cationic PISs under long wavelength UV lights (>300 nm) [73][74][75][76][77][78][79][80][81][82][83] or even visible lights [84][85][86][87][88][89][90][91][92][93][94]. However, photopolymerization reactions under low intensity visible light irradiation conditions were rather rare and challenging before 2011.…”

Section: Introductionmentioning

confidence: 99%

Visible light sensitive photoinitiating systems: Recent progress in cationic and radical photopolymerization reactions under soft conditions

Xiao

Zhang

Dumur

et al. 2015

Progress in Polymer Science

491

248

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Section: Introductionmentioning

confidence: 99%

Visible light sensitive photoinitiating systems: Recent progress in cationic and radical photopolymerization reactions under soft conditions

Xiao

Zhang

Dumur

et al. 2015

Progress in Polymer Science

491

248

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“…The diepoxide 4-(4-oxiranyl-butoxy)-benzoic acid 4-(4-oxiranyl-butoxy)-phenyl ester (1) (nematic phase between 51.5 8C and 70.2 8C), hex-5-enyloxy-phenol (6) and 4-hex-5-enyloxybenzoic acid (2) were prepared according to literature [10] as well as (9-oxo-9H-fluoren-2-yl)-phenyl-iodonium hexafluoroantimonate(V) (11). [22] (À)-4-(4-Oxiranyl-butoxy)-benzoic acid cholesterol ester (4) (Scheme 1) (À)-4-(Hex-5-enyloxy)-benzoic acid cholesterol ester (3) 2.2 g (0.01 mol) 4-hex-5-enyloxy-benzoic acid (2), 3.86 g (0.01 mol) cholesterol, 2.06 g (0.01 mol) dicyclohexylcarbodiimide (DCC), 0.148 g (0.001 mol) 4-pyrrolidinopyridine dissolved in 20 ml dichloromethane were stirred at room temperature for 6 h. After purification by column chromatography on silica gel with dichloromethane as solvent 3.3 g (65%) of the product was obtained. 1 (À)-4-(4-Oxiranyl-butoxy)-benzoic acid cholesterol ester (4) 3 g (0.005 mol) of the prepared alkene (3), 2.4 g (0.014 mol) 3-chloro-benzenecarboperoxoic acid (MCPBA, 70%) and 30 ml dichloromethane were stirred at room temperature for 6 h. The formed precipitate was filtered off.…”

Section: Synthesis Of the Materialsmentioning

confidence: 99%

Preparation and Properties of Cholesteric Network Polymers Based on Liquid Crystalline Epoxides

Hartwig

Mahato

Kaese

et al. 2005

Macro Chemistry & Physics

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Summary: Polyether network polymers with cholesteric superstructure are formed by the photochemically induced cationic copolymerisation of a nematic diepoxide with chiral epoxides. If a cholesteric superstructure is formed or not, depends on the temperature at which the photopolymerisation is carried out. The storage modulus is higher above TG in samples with cholesteric superstructure. Optical rotations and vibrational circular dichroism spectra (VCD) depend strongly on the surface state of the substrates. From the VCD spectra it is concluded that the copolymerisation leads to different superstructures depending on the rub directions of the substrates.

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“…This is not the case for photoinitiators for the cationic polymerization of epoxides. A sensitization of the commercial iodonium salt phenyl [p-(2-hydroxydecanoxy)phenyl]iodonium hexafluoroantimonate with fluorenone could not be observed [15]. The sulfonium salts are commercially available as 50% propylene carbonate solutions and, during the polymerization of epoxides, the solvent is built into the polymer network via a ring-opening reaction.…”

Section: Initiators For the Cationic Polymerization Of Epoxidesmentioning

confidence: 99%

Influence of Proton Donors on the Cationic Polymerization of Epoxides

2005

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The cationic polymerization of epoxy resins becomes more and more important in adhesive bonding technology. Most often a cationic photopolymerization is applied, but occasionally thermally induced cationic polymerization of epoxides is also used. The polymerization is strongly influenced by water, namely the humidity of the surrounding atmosphere in which the adhesives are cured. Traces of water or other proton donors are required as co-catalyst for the initiation of the polymerization. On the other side the cation as well as the anion of the latent initiators is hydrolyzed by the long term influence of moisture. But water does not only influence the initiation reaction of the polymerization but also the chain growth reaction. Depending on the kind of epoxide the polymerisation is strongly accelerated by the water or strongly retarded. These extreme differences are explained by differences in the mechanism of the chain transfer reaction carried out by the water. In any case the water reduces the mechanical strength of the cured epoxides by the formation of unbound chain-ends in the polymer network and therefore lower cross-link density. Also alcohols lead to chain transfer reactions during polymerization of the epoxides and consequently they have an influence on the polymerization kinetics as well as on the mechanical properties of the epoxides Different polymeric and oligomeric alcohols (polyols) are applied to adjust the mechanical properties of cationically curing adhesives. It could for example be shown that the addition of polytetrahydrofuran leads to polymers with rubber elastic behaviour. But also the polymerization kinetics is strongly influenced by polyols. In the case of polyethers based on 1,2-diols the protons required to progress the polymerization can be fixed within five-membered rings. The polymerization rate is decelerated in the presence of such polyols, therefore. The formed structures have some similarity with crownethers complexing a proton. And it is therefore not surprising that crown-ethers inhibit the cationic polymerisation very efficiently. On the other hand no retardation of the reaction rate is observed if 1,4-diol based polyethers are used to modify the properties of the materials. 205 208 Scheme 14.1 Synthesis of (9-oxo-9H-fluoren-2-yl)phenyliodonium hexafluoroantimonate.

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(9-Oxo-9H-fluoren-2-yl)-phenyl-iodonium hexafluoroantimonate(V) – a photoinitiator for the cationic polymerisation of epoxides

Cited by 44 publications

References 6 publications

Visible light sensitive photoinitiating systems: Recent progress in cationic and radical photopolymerization reactions under soft conditions

Visible light sensitive photoinitiating systems: Recent progress in cationic and radical photopolymerization reactions under soft conditions

Preparation and Properties of Cholesteric Network Polymers Based on Liquid Crystalline Epoxides

Influence of Proton Donors on the Cationic Polymerization of Epoxides

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