Novel one-component polymeric benzophenone photoinitiator containing poly (ethylene glycol) as hydrogen donor

Wang, Kemin; Lu, Yuhui; Chen, Penghui; Shi, Jingsong; Wang, Honggang; Yu, Qiang

doi:10.1016/j.matchemphys.2013.11.051

Cited by 45 publications

(32 citation statements)

References 15 publications

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“…Thioxanthone [19][20][21][22] and benzophenone [23][24][25][26] and, more recently, novel erythrosine B [27] and naphthoquinone [28] derivatives linked with appropriate groups have been synthesised and applied as initiators for free radical polymerisation. There are very few chromophores that can be used to design onecomponent initiator systems.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and application of dyes derived from benz[cd]indol‐2(1H)‐one as visible‐light‐absorbing polymerisation photoinitiators

Strzelczyk

Michalski

2016

Coloration Technology

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Several potential initiators based on benz [cd]indol-2(1H)-one dye have been synthesised and evaluated in the radical polymerisation of a system containing trimethylolpropane triacrylate under visible light. Absorption, fluorescence, and phosphorescence spectra and the electrochemical properties of these novel dyes were determined. Owing to the presence of an appropriate hydrogen donor group in their structure, these photoinitiators do not need an extra coinitiator to initiate the polymerisation process. During photopolymerisation they act both as a triplet sensitiser and as a hydrogen donor. The relationship between the polymerisation rate and the triplet-excited-state reduction potential suggests that initiating radicals are formed from the triplet state via hydrogen transfer. This mechanism is supported by density functional theory calculations. 8-Bromo-6-[(2-sulphanylethyl)sulphanyl]benzo[cd]indol-2(1H)-one and 8-bromo-6-sulphanylbenz[cd]indol-2(1H)-one may be applied as visible-light initiators of free radical polymerisation to obtain a low-molecular-weight polymer.

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Section: Introductionmentioning

confidence: 99%

Synthesis and application of dyes derived from benz[cd]indol‐2(1H)‐one as visible‐light‐absorbing polymerisation photoinitiators

Strzelczyk

Michalski

2016

Coloration Technology

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“…In the last decade many papers have described the synthesis of initiators. Only thioxanthone [3][4][5][6][7][8][9], benzophenone [10][11][12][13][14][15][16], erythrosine B [17], and, more recently, naphthoquinone [18] and benz[cd]indol-2(1H)-one [19] linked with appropriate groups have been applied as chromophores to obtain one-component initiator systems. There are two different ways to create initiators sensitive to visible radiation.…”

Section: Introductionmentioning

confidence: 99%

Naphthoylenebenzimidazolone dyes as one‐component photoinitiators

Strzelczyk

2017

Coloration Technology

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The appropriate substituents have been added to a 7H-benzimidazo[2,1-a]benz [de]isoquinolin-7-one skeleton in order to obtain a one-component initiator system. The absorption, fluorescence, and electrochemical properties of these naphthoylenebenzimidazolone dyes and their usefulness as visible light initiators of free radical polymerisation of trimethylolpropane triacrylate were examined. The initiation efficiency of these dyes was compared with that of the parent 7H-benzimidazo[2,1-a]benz[de]isoquinolin-7-one in the presence of a coinitiator. Results show that these bifunctional dyes are able to initiate polymerisation without an additional coinitiator. Photopolymerisation studies and the relationship between the rate of polymerisation and the free energy change for electron transfer revealed that, depending on the concentration, initiating radicals are generated via intra-and intermolecular electron transfer.

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“…Besides high reactivity, solubility in the formulation, low odor and toxicity, no darkening due to the migration of residues in the cured film, and good storage stability are other important issues for the design and preparation of new high performance photoinitiating systems. Recently, researchers have been investigating copolymerizable, polymeric (PPIs), dendritic, or hyperbranched radical PIs to fulfill the above mentioned requirements, due to their advantages in comparison with their corresponding low molecular weight analogs.…”

Section: Introductionmentioning

confidence: 99%

Photophysical and Photochemical Studies of Novel Thioxanthone‐Functionalized Methacrylates through LED Excitation

Eren

Yasar

Avi̇yente

et al. 2016

Macro Chemistry & Physics

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Five novel thioxanthone (TX)‐functionalized methacrylates as copolymerizable photoinitiators (CopPIs) for polymerization of acrylates are synthesized from reactions of tert‐butyl α‐bromomethacrylate with 2‐hydroxy thioxanthone (TX1) and 1,4‐dihydroxy thioxanthone (TX3), cleavage of their respective tert‐butyl ester groups with trifluoroacetic acid (TX2, TX4), and by reaction of the acid chloride derivative of TX2 with Irgacure 2959 (TX5). These CopPIs absorb in the near UV–visible region (390–420 nm; absorption redshift ≈10–40 nm, ε values comparable to TX). Their performances are studied under LED exposure at 385 and 405 nm using real‐time FTIR. The reactivities of TX1 and TX2 are similar to isopropyl thioxanthone, used as reference; TX3 and TX4 have lower reactivities, due to their difunctionality, which however makes them good crosslinking agents. TX5 is the first monomeric PI possessing two different type side‐chain photoinitiating groups. The migration stability of two of these CopPIs is shown in the cured polyacrylates. The photochemical mechanisms are studied by electron spin resonance, steady state photolysis, laser flash photolysis, and cyclic voltammetry.

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Novel one-component polymeric benzophenone photoinitiator containing poly (ethylene glycol) as hydrogen donor

Cited by 45 publications

References 15 publications

Synthesis and application of dyes derived from benz[cd]indol‐2(1H)‐one as visible‐light‐absorbing polymerisation photoinitiators

Synthesis and application of dyes derived from benz[cd]indol‐2(1H)‐one as visible‐light‐absorbing polymerisation photoinitiators

Naphthoylenebenzimidazolone dyes as one‐component photoinitiators

Photophysical and Photochemical Studies of Novel Thioxanthone‐Functionalized Methacrylates through LED Excitation

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