Revisiting aromatic thiols effects on radical photopolymerization

Krongauz, Vadim V.; Chawla, Chander P.

doi:10.1016/s0032-3861(03)00099-5

Cited by 23 publications

(28 citation statements)

References 18 publications

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“…The selected low polarity monomers, oligomers and other components were used to generate a series of hydrophilic resin formulations, some of which are presented in Table . To verify the completeness of photopolymerization after photocuring, acrylic double bond presence in the cured films was checked by its infrared absorption at 810 cm −1 . Practically no residual double bond remained, as was expected.…”

Section: Resultsmentioning

confidence: 95%

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Synthesis of solvatochromic merocyanine dyes and their immobilization to polymers

Nordhaus

Krongauz

Hai

2016

J of Applied Polymer Sci

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Solvatochromic merocyanine dyes were immobilized onto polymer surfaces and copolymerized with acrylic resins, yielding novel reversibly solvatochromic polymers, which were used as solvent polarity indicators that exhibited different colors in water and alcohols. To generate solvatochromic polymer for solvent polarity indication, two solvatochromic merocyanine dyes containing moieties, which allow their immobilization onto polymer surfaces, or copolymerization with acrylic and vinyl monomers, were sequentially synthesized in four and six steps. Merocyanine dye (E)‐2‐(2‐(1‐(6‐aminohexyl)pyridinium‐4‐yl)vinyl)‐4,6‐dichlorophenolate (AHPVD) was prepared with a terminal aminohexyl group which allowed covalent bonding to activated carboxylated or sulfonated polymeric materials. The dyes were covalently bonded to the polymer surfaces, such as, nylon, polycarbonate, polyethylene terephthalate, and silicone. Solvatochromic merocyanine dye (E)‐2‐(2‐(1‐(6‐acrylamidohexyl)pyridinium‐4‐yl)vinyl)‐4,6‐dichlorophenolate (AAPVD) was synthesized for radical copolymerization with acrylate and vinyl monomers and oligomers. Side‐chain solvatochromic merocyanine‐containing hydrophilic polymers with differential water and alcohol absorption were obtained upon photoinitiated radical copolymerization with specially formulated acrylated resins. © 2016 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2017, 134, 44451.

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Section: Resultsmentioning

confidence: 95%

“…Doctor knife with 12 mil gap was used to coat resin formulations on the 25 × 75 cm glass microscope slides. Completeness of acrylate resins polymerization was verified by acrylate double bond infrared absorption at 810 cm −1 using Nicolet 8700 Fourier transform infrared spectrophotometer (Thermal Electron) …”

Section: Methodsmentioning

confidence: 99%

Synthesis of solvatochromic merocyanine dyes and their immobilization to polymers

Nordhaus

Krongauz

Hai

2016

J of Applied Polymer Sci

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“…Aromatic thiols are well-known strong quenchers of the triplet state photoinitiators. [51][52][53][54] Investigating the initiation mechanism by laser flash photolysis, Andrzejewska and co-workers observed a rapid quenching of the excited ITX * with the thiols as the transient peak of ITX * around 640 nm dropped quickly following the appearance of new absorption peaks at 425 and 590 nm. The observed insensitivity of thiol-based systems to oxygen inhibition is due to the ability of peroxy radicals formed by oxygen scavenging to abstract a hydrogen atom from the thiols thus giving rise to the formation of a new initiating thiyl radical.…”

Section: Co-initiatorsmentioning

confidence: 99%

Shining a light on an adaptable photoinitiator: advances in photopolymerizations initiated by thioxanthones

2015

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Photochemistry has been playing a central role in the synthetic polymer community. Aromatic ketones, examples of which include benzophenone, thioxanthone, camphorquinone, among others, are renowned for their excellent optical characteristics and have been extensively taken advantage of photochemically induction of polymerization processes. Of particular interest is thioxanthone due to its adaptability for bearing different functionalities and applications in various modes of photopolymerization which accomplishes photoinitiation in conjunction with other co-initiator compounds; a behavior that is referred to as bi-molecular photoinitiation. In this paper, we review the photochemistry of thioxanthonebased systems and their use in different modes of photoinitiated polymerizations. Citing examples from literature, the development of various photoinitiating systems based on thioxanthones along with an understanding of their mechanistic behavior has been elucidated in advance.Scheme 1 Typical representation of the photolysis of the radical photoinitiators based on Type I (top) and Type II (bottom) systems on the example of a benzoin derivative and thioxanthone, respectively.Scheme 3 Synthesis of thioxanthones by condensation of thiosalicylic acid and aromatic compounds in the presence of concentrated sulfuric acid.

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“…The weakness of the S-H bond can be explained by the high reactivity of these compounds towards chain-carrying macroradicals, leading to high chain transfer constants, irrespectively of the used monomer. In turn, high reactivity of the thiol radicals is characterized by almost ideal chain transfer behaviour of thiols, with a large decrease in the polymer molecular mass without a substantial change in the polymerization rate [7][8][9][10].…”

Section: Introductionmentioning

confidence: 99%

Thermal and spectral analysis of copolymers with sulphur groups

Fila

Grochowicz

Podkościelna

2017

J Therm Anal Calorim

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The paper presents the synthesis, structure and polymerization of S-phenyl 2-methylprop-2-enethioate (PSM). This compound was prepared in the reaction of thiophenol with methacryloyl chloride. The obtained PSM was purified on the chromatographic column. Chemical structure of the monomer was confirmed by spectroscopic methods (ATR-FTIR, GC-MS, 1 H and 13 C NMR). Next bulk polymerization of PSM with styrene (St) or methyl methacrylate (MMA) was performed. In this way, linear copolymers were obtained. The number and mass average molar mass of the obtained copolymers were determined by gel permeation chromatography (GPC). Additionally, crosslinked copolymers of the commercial monomer S,S 0 -thiodi-4,1-phenylene bis(thiomethacrylate) (DMSPS) under the same conditions were synthesized. The influence of thiol monomers on the physico-chemical properties of the obtained copolymers was determined. Thermal properties of the synthesized materials were investigated by means of DSC and TG/DTG.

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Revisiting aromatic thiols effects on radical photopolymerization

Cited by 23 publications

References 18 publications

Synthesis of solvatochromic merocyanine dyes and their immobilization to polymers

Synthesis of solvatochromic merocyanine dyes and their immobilization to polymers

Shining a light on an adaptable photoinitiator: advances in photopolymerizations initiated by thioxanthones

Thermal and spectral analysis of copolymers with sulphur groups

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