Photoinitiated cationic polymerization of epoxy alcohol monomers

Crivello, James V.; Liu, Saoshi

doi:10.1002/(sici)1099-0518(20000201)38:3<389::aid-pola1>3.0.co;2-g

Cited by 121 publications

(81 citation statements)

References 29 publications

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“…[46] According to this mechanism, the terminal oxonium ion of the growing polyether chain could be intercepted by the hydroxyl group, resulting in a rapid proton transfer from the growing chain end to the monomer. Several authors reported that the addition of hydroxylate compounds such as alcohols, [47] siloxanes, [48] phenolic polymers [49] or monofers [50] to epoxy monomers was able to alter the reaction kinetics, with generally an accelerating effect. Poorly condensed SSQO (reduced aging times) are characterized by a high concentration in silanol groups and can potentially afford an important amount of hydroxyl volatile species (water, alcohol) by photoacidcatalyzed sol/gel.…”

Section: Epoxy Cationic Photopolymerizationmentioning

confidence: 99%

Synthesis of Organosilica Films Through Consecutive Sol/Gel Process and Cationic Photopolymerization

Versace

Chemtob

Croutxé‐Barghorn

et al. 2010

Macro Materials & Eng

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The cationic photopolymerization of epoxy polysilsesquioxane resins synthesized through a acid‐catalyzed sol/gel process is studied. To elucidate the effect of the organic substituent on sol/gel reaction kinetics, two organotrimethoxysilanes with different organic groups were employed. Effects of UV irradiation on the microstructure of the epoxy‐functional polysilsesquioxanes were also studied. 29Si solid‐state MAS NMR proved that UV‐generated Brönsted acids favored a work‐up of the silicate network by promoting new sol/gel condensation reactions. There was a significant slowdown of epoxy conversion rates with increasing sol aging, which may be due to a competition between an active chain end and an activated monomer mechanism for the epoxy cationic polymerization.magnified image

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Section: Epoxy Cationic Photopolymerizationmentioning

confidence: 99%

Synthesis of Organosilica Films Through Consecutive Sol/Gel Process and Cationic Photopolymerization

Versace

Chemtob

Croutxé‐Barghorn

et al. 2010

Macro Materials & Eng

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“…3 Epoxy groups can react with nucleophiles such as amines, undergo ring opening polymerization at high temperature or react under cationic ring opening conditions to produce crosslinked networks. 1,[4][5][6] Glycidyl carbamate (GC) functional resins are synthesized by the reaction of an isocyanate functional compound with glycidol to yield a carbamate (urethane) linkage (-NHCO-) and reactive epoxy group in the final product. GC chemistry results in a resin that contains both the urethane and the epoxy functionalities in its chemical structure.…”

Section: Introductionmentioning

confidence: 99%

The influence of structural modification and composition of glycidyl carbamate resins on their viscosity and coating performance

Harkal

Muehlberg

et al. 2010

J Coat Technol Res

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The synthesis, characterization, and coatings performance of a series of glycidyl carbamate (GC) resins synthesized from a hexamethylene diisocyanate biuret resin, glycidol, and alcohols were explored. The partial replacement of glycidol with alcohols was explored as a way to reduce the viscosity of multifunctional GC resins. Six modified GC resins were obtained by replacing one-third of the glycidol with alcohols and ether alcohols. The modified GC resins were characterized using FTIR and 13 C NMR. The alcoholmodified GC resins had significantly lower viscosity than that of the control GC resin. The effect of amount of alcohol modifier on resin viscosity was also studied by making a series of resins with different levels of modifier. Both amine-cured and self-crosslinked coatings were prepared from the resins. Coating properties such as hardness, impact strength, methyl ethyl ketone double rubs, flexibility, and adhesion were studied. Differential scanning calorimetry and thermogravimetric analysis were also used to study the thermal properties of the coatings. The resin structures and their coating performance showed an excellent correlation. The coating performance was found to be governed by the type of modifier, structural compositions of the modifier in the resins, type of amine crosslinkers, and techniques of crosslinking used.

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“…The first can be exemplified with cationic polymerization of cycloaliphatic epoxides 5,6 and the latter by epoxyamine coupling reactions. 7,8 Furthermore, the benefit of the epoxy group is that it can undergo reactions with numerous other functional groups such as acids, 7,9 anhydrides, 7,10 alcohols, 9,11 and thiols. 12,13 One group of bio-based epoxy functional structures that has obtained a significant amount of interest is epoxidized vegetable oils, e.g., epoxidized soybean oil.…”

Section: Introductionmentioning

confidence: 99%

Fully bio-based aliphatic thermoset polyesters via self-catalyzed self-condensation of multifunctional epoxy monomers directly extracted from natural sources

Nameer

Johansson

2017

J Coat Technol Res

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The use of bio-based raw material is regarded as a sustainable way to address environmental concerns. A naturally occurring monomer, 9,10-epoxy-18-hydroxyoctadecanoic acid (EFA), was retrieved from outer birch bark. A series of model experiments revealing relative reaction rates for epoxide, carboxylic acid, and alcohol functional groups was investigated. Real-time Fourier transform infrared spectroscopy and nuclear magnetic resonance were used to follow the different model experiments. The results on the model systems were then compared to the thermoset formation of thermally cured EFA. Finally, the adhesive properties of crosslinked EFA on different substrates were evaluated.

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Photoinitiated cationic polymerization of epoxy alcohol monomers

Cited by 121 publications

References 29 publications

Synthesis of Organosilica Films Through Consecutive Sol/Gel Process and Cationic Photopolymerization

Synthesis of Organosilica Films Through Consecutive Sol/Gel Process and Cationic Photopolymerization

The influence of structural modification and composition of glycidyl carbamate resins on their viscosity and coating performance

Fully bio-based aliphatic thermoset polyesters via self-catalyzed self-condensation of multifunctional epoxy monomers directly extracted from natural sources

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