A New Photoinitiator for Anionic Polymerization

Palmer, Bentley J.; Kutal, Charles; Billing, Roland; Hennig, H.

doi:10.1021/ma00108a078

Cited by 32 publications

(22 citation statements)

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“…189 The polymerization proceeds via a zwitterionic mechanism. Kutal and co-workers 190 reported the use of the Pt(acac) 2 complex in Figure 1. Photoinduced keto-enol tautomerism of a phenacylbenzoylpyridinium salt (λ ex > 507 nm).…”

Section: Anionic Polymerizationmentioning

confidence: 99%

Photoinitiated Polymerization: Advances, Challenges, and Opportunities

2010

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The use of photoinitiated polymerization is continuously growing in industry as reflected by the large number of applications in not only conventional areas such as coatings, inks, and adhesives but also high-tech domains, optoelectronics, laser imaging, stereolithography, and nanotechnology. In this Perspective, the latest developments in photoinitiating systems for free radical and cationic polymerizations are presented. The potential use of photochemical methods for step-growth polymerization is also highlighted. The goal is, furthermore, to show approaches to overcome problems associated with the efficiency, wavelength flexibility, and environmental and safety issues in all photoinitiating systems for different modes of activation. Much progress has been made in the past 10 years in the preparation of complex and nanostructured macromolecules by using photoinitiated polymerizations. Thus, the new and emerging applications of photoinitiated polymerizations in the field of biomaterials, surface modification, preparation of block and graft copolymers, and nanocomposites have been addressed.

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Section: Anionic Polymerizationmentioning

confidence: 99%

Photoinitiated Polymerization: Advances, Challenges, and Opportunities

2010

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“…Photoassisted anionic polymerization has long been examined but remains less studied than the free radical polymerization or the cationic polymerization due to the longer reaction time this polymerization technique requires compared to the two others. [194] Recently, alternatives to the conventional light-curing strategies based on photobase generations has been proposed in the literature, [195][196][197][198][199][200] notably based on photoinduced electron transfer (PET) processes. [201][202][203] Typically, these strategies are based on the photooxidation of a metal complex when opposed to the appropriate electron-deficient partner.…”

Section: Ferrocene and Alkyl-substituted Ferrocenesmentioning

confidence: 99%

“…[201][202][203] Typically, these strategies are based on the photooxidation of a metal complex when opposed to the appropriate electron-deficient partner. Using this strategy, a wide range of structures have been examined, including inorganic complexes (trans-Cr(NH3)2(NCS)4 -1 , Pt(acac)2 (with acac standing for acetylacetonate)), [197,204] organometallic complexes (Cr(CO)5L and W(CO)5L with L standing for pyridine and related derivatives), [196] porphyrins, [205,206] pyridinium [199] and phosphonium [200] salts, violet leuconitrile and malachite green leucohydroxide. [207] Even if the mechanism of generation of active initiating species differs with the different aforementioned photoinitiators, as common point, an anion is released during photoexcitation so that the chain growth can rapidly propagate by addition of repeating monomer units, according to the mechanism proposed in the Scheme 1.…”

Section: Ferrocene and Alkyl-substituted Ferrocenesmentioning

confidence: 99%

Recent advances on ferrocene-based photoinitiating systems

Dumur

2021

European Polymer Journal

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Photoinitiators of polymerization with reversible electrochemical properties are actively researched as these molecules can advantageously be used in photocatalytic systems, enabling to reduce the photoinitiators content within the photocurable resins. In this field, ferrocene which is extensively used by electrochemists as a reference compound for cyclic voltammetry also exhibits a significant absorption in the visible range as well as a low oxidation potential so that this metallocene was used as a potential candidate for the design of photoinitiators of polymerization. Over the years, ferrocene has been examined in numerous polymerization processes going from anionic to cationic polymerizations, but also for the freeradical polymerization of acrylates or as a sacrificial electron donor in free radical polymerization processes. Parallel to this, the development of cheap, compact and energysaving irradiation setups based on light-emitting diodes (LEDs) have clearly favored the development of visible light photoinitiators and this technology has nowadays the potential to replace the well-established UV photopolymerization. In this review, an overview of the recent development of the ferrocene-based photoinitiating systems is provided. To evidence the interest of the ferrocene derivatives recently developed, comparisons with benchmark photoinitiators will be provided.

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“…Some works were reported for the anionic coordination polymerization of epoxides by a new catalyst system consisting of titanium tetraisopropoxide and photochemically generated phenol 41. Moreover, the more powerful monomer ethyl cyanoacrylate (ECA) was polymerized by NCS − ions generated by photoinduced ligand exchange reactions 42,43. We have demonstrated that, besides these organometallic complexes, specially designed organic compounds such as alkoxy pyridinium44 and phosphonium45 salts can also act as photoinitiators for anionic polymerization of ECA.…”

Section: Polymerizationmentioning

confidence: 99%

Phenacyl onium salt photoinitiators: synthesis, photolysis, and applications

Yaǧcı

Durmaz

Aydoğan

2007

The Chemical Record

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Onium salts, namely sulfonium, phosphonium, ammonium, and pyridinium salts containing phenacyl group are photoinitiators appropriate for the polymerization of monomers such as oxiranes and vinyl ethers, which are not polymerizable by a free-radical mechanism. The initiation is accomplished by direct or indirect (sensitized) photolysis of the salts. Depending on the type of the salt, the direct photoinitiation of cationic polymerization involves reversible or irreversible processes. The photolysis of phenacylsulfonium compounds proceeds by a reversible process, while the other types undergo irreversible photolysis leading to complete fragmentation of the photoinitiator. An additionally useful tool, namely photosensitized generation of initiating species enlarges the versatility of these salts as photoinitiators. Photoinitiated free-radical and zwitterionic polymerizations by using phenacyl-type salts are also addressed. Keto-enol tautomerization of phenacyl pyridinium salts is discussed. Moreover, an interesting application concerning in situ synthesis of clay-poly(methyl methacrylate) nanocomposites with the aid of the phenacyl anilinium salt-based photopolymerization technique is noted.

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A New Photoinitiator for Anionic Polymerization

Cited by 32 publications

References 1 publication

Photoinitiated Polymerization: Advances, Challenges, and Opportunities

Photoinitiated Polymerization: Advances, Challenges, and Opportunities

Recent advances on ferrocene-based photoinitiating systems

Phenacyl onium salt photoinitiators: synthesis, photolysis, and applications

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