Synthesis and Photoinitiated Cationic Polymerization of Substituted 2-Cyclopropyl-4-methylene-1,3-dioxolanes

Al-Doaiss, Aniss Abdo; Klemm, Elisabeth; Stadermann, D.; Moszner, Norbert

doi:10.1002/1521-3935(20010101)202:2<270::aid-macp270>3.0.co;2-p

Cited by 3 publications

(4 citation statements)

References 2 publications

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“…Obviously, ring-opening is the most favourable step and the hydride shift in the primary carbenium ion is slower than the addition of the next monomer. That means that there is a significant difference with the cyclopropane-substituted exomethylene dioxolanes [8] where no opening of the cyclopropane could be detected. Apparently the oxygen in exomethylene dioxolanes is stabilizing the cation formed and addition of monomer is faster than ring-opening of the cyclopropane.…”

Section: Resultsmentioning

confidence: 99%

“…[3] and literature quoted there) and monomers containing cyclopropane units besides other rings. [6,7] In a previous paper, [8] we reported about synthesis and cationic photopolymerization of substituted 2-cyclopropyl-4-methylene-l,3-dioxolanes. We found that the dioxolane ring has completely been opened but the cyclopropane ring remained unchanged in the polymer.…”

Section: Introductionmentioning

confidence: 99%

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Photoinitiated Cationic Polymerization of Substituted Vinylcyclopropanes

Al-Doaiss

Günther

Klemm

et al. 2005

Macro Chemistry & Physics

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Summary: The photoinitiated cationic polymerization of 1‐cyclopropyl‐l‐phenyl‐ethylene, 1‐cyclopropyl‐l‐(p‐methoxyphenyl)ethylene and 1‐cyclopropyl‐l‐(p‐fluorophenyl)ethylene at ambient temperatures in bulk and in solution was investigated using (η5‐2,4‐cyclopentadiene‐l‐yl)[l,2,3,4,5,6‐η] (l‐(methylethyl) benzene)iron(I) hexafluorophosphate (Irgacure 261, I‐1) and ditolyliodonium hexafluorophosphate (I‐2). In contrast to our results in the polymerization of 2‐cyclopropyl‐4‐methylene‐l,3‐dioxolanes, partial ring‐opening of the cyclopropane ring could be detected. A volume shrinkage of about 11% was found.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Photoinitiated Cationic Polymerization of Substituted Vinylcyclopropanes

Al-Doaiss

Günther

Klemm

et al. 2005

Macro Chemistry & Physics

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“…The RROP of CKA monomers is another route for the synthesis of and benzoin isopropylether (λ 247 326 nm) respectively, has been compared to their thermal radical polymerization using AIBN at 60 • C. Total monomer conversion was reached by photopolymerization in 3 h for MDO and 2 h for 2-methylene-4-phenyl-1,3-dioXolane using 2-ethylanthraquinone, whereas 60 h were necessary when the polymerization was performed with AIBN [255,256]. The polyester resins based on MDO exhibited a lower shrinkage (7.2 %) compared to PMMA resins ( 21shrinkage (6-6.5 %) as compared to PMMA resins (21 %) [262]. Interestingly, only a few studies mentioned the UV induced radical ROP of CVAs.…”

Section: Cyclic Acetalsmentioning

confidence: 99%

Photoinduced ring-opening polymerizations

Guy

Giani

Blanquer

et al. 2021

Progress in Organic Coatings

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“…A similar comparison (Irgacure 261 vs. onium salts) established for the ring opening polymerization of substituted 2-cyclopropyl-4-methylene-1,3-dioxolanes confirmed the same trends. [97] For this study, dioxolane monomers M4-M6 were selected as the polymerization of such monomers can efficiently address the volume shrinkage issue typically observed during the polymerization of acrylates. In this field, 4-methylene-2-phenyl-1,3-dioxolane M7 is a representative monomer.…”

Section: Ferrocenium Salts Used As Photoinitiators Of Polymerization mentioning

confidence: 99%

Recent advances on iron-based photoinitiators of polymerization

Dumur

2020

European Polymer Journal

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With regards to the environmental and safety concerns raised nowadays by the polymer industry, polymerization processes requiring light as the activation source are currently knowing a revival of interest after decades of disinterest. Recent progresses in photopolymerization are notably sustained by the development of new polymerization application namely 3D and 4D printing enabling an unprecedented access to structures of incredible complexity. Parallel to the manufacturing process, the polymer material itself and its composition are also facing numerous questions concerning their environmental and human health impacts. Beyond the monomers, the different additives introduced in the resin can also be potentially toxic so that a great deal of efforts is currently done to develop new photoinitiators with a toxicity assessed as being insignificant. In this field, iron-based metal complexes are candidates of choice due to the clinical demonstration of their very low toxicities. Among iron complexes, ferrocene is among the most widely studied iron-based metallocene. Due to its unique and reversible electrochemical properties as well as their absorption centred in the visible range, numerous photoinitiators have been developed with ferrocene or its oxidized form i.e. ferrocenium. Parallel to this, the remarkable electrochemical properties of ferrocenium made it an excellent candidate for its incorporation in photoinitiating systems. However, interest for iron-based photoinitiators was not limited to ferrocene and ferrocenium, and Schiff base complexes were also successfully used as initiators of polymerization. In this review, an overview of the different iron-based photoinitiating systems reported to date is presented. More precisely, if iron-based photoinitiators are developed since 50 years, a special focus will be done on photoinitiators designed for recent polymerization conditions, namely, under visible light and low light intensity.

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Synthesis and Photoinitiated Cationic Polymerization of Substituted 2-Cyclopropyl-4-methylene-1,3-dioxolanes

Cited by 3 publications

References 2 publications

Photoinitiated Cationic Polymerization of Substituted Vinylcyclopropanes

Photoinitiated Cationic Polymerization of Substituted Vinylcyclopropanes

Photoinduced ring-opening polymerizations

Recent advances on iron-based photoinitiators of polymerization

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