Novel polymeric, thio‐containing photoinitiator comprising in‐chain benzophenone and an amine coinitiator for photopolymerization

Wei, Jun; Yin, Jie

doi:10.1002/pola.21818

Cited by 24 publications

(23 citation statements)

References 47 publications

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“…4-amino-4 0 -chlorobenzophenone (ACBP), 4-amino-4 0 -(4-aminothiophenyl)benzophenone (AATBP), MTPBP, and BMTPBP were synthesized according to our previous work. [9,10,21] Other chemicals were of analytical grade except as noted.…”

Section: Experimental Partmentioning

confidence: 99%

“…The precipitate was filtered and washed with a large amount of water. The crude product was recrystallized by ethanol, and dried under vacuum at 50 8C for 48 h to yield 21 …”

Section: Synthesismentioning

confidence: 99%

“…This result can be mainly ascribed to the strong electron donating ability of thiophenyl group that is directly linked to BP moieties in MTBP and MTPBP. [21,31] Moreover, the polarity of the microenvironment of BP moieties will increase in the presence of imide group (nitrogen atom), and the increasing polarity may increase its maximum of absorption. [25] The polarity of the microenvironment of BP moieties in MTBP, due to the maleimide group directly links to BP moieties, will increase relatively higher than that of the indirectly one, MTPBP.…”

Section: Uv-vis Spectramentioning

confidence: 99%

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A Highly Efficient Polymerizable Photoinitiator Comprising Benzophenone, Thio Moieties, and N‐Arylmaleimide

Wei

Wang

2010

Macro Chemistry & Physics

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A novel, highly efficient, polymerizable, thio‐containing photoinitiator, 4‐maleimido‐4'‐thiophenylbenzophenone (MTBP), was synthesized by directly introducing maleimide to benzophenone moieties. Three polymerizable photoinitiators with different location or number of maleimide substituents, together with the bare benzophenone, were chosen to evaluate the photoefficiency of MTBP. Photopolymerization studies indicate that polymerizable photoinitiator with single maleimide substituent directly linking to benzophenone moieties is more efficient for photopolymerization of vinyl monomers than those with indirect or double maleimide substituents. As for the photopolymerization of 1,6‐hexanediol diacrylate, MTBP show surprisingly high efficiency, and the final conversion runs up to 95.94%.

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Section: Experimental Partmentioning

confidence: 99%

“…The precipitate was filtered and washed with a large amount of water. The crude product was recrystallized by ethanol, and dried under vacuum at 50 8C for 48 h to yield 21 …”

Section: Synthesismentioning

confidence: 99%

Section: Uv-vis Spectramentioning

confidence: 99%

See 1 more Smart Citation

A Highly Efficient Polymerizable Photoinitiator Comprising Benzophenone, Thio Moieties, and N‐Arylmaleimide

Wei

Wang

2010

Macro Chemistry & Physics

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“…199875-93-9, functionality 2, from Shin-Nakamura Chemical Co. Ltd.) and 4-amino-4 0 -chlorobenzophenone (ACBP; synthesized in our laboratory according to our previous work [39] ) were used in the presented study. Other chemicals were of analytical grade except as noted.…”

Section: Experimental Partmentioning

confidence: 99%

A Highly Efficient Polyurethane‐Type Polymeric Photoinitiator Containing In‐chain Benzophenone and Coinitiator Amine for Photopolymerization of PU Prepolymers

Wei¹,

Wang²,

Jiang³

et al. 2006

Macro Chemistry & Physics

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Summary: A novel polyurethane‐type polymeric photoinitiator (PUIOA) was synthesized through polycondensation of a novel diamine AAPBP, TDI and MDEA. The BP and coinitiator amine structures were successfully introduced into the backbones of PUIOA. A polymeric photoinitiator without the coinitiator amine in the polymer chain (PUIO) was also synthesized for comparison. FT‐IR, 1H NMR and GPC analyses confirmed the structures of polymeric photoinitiators. The UV‐vis spectra of PUIOA and PUIO are similar to the parent AAPBP, and both exhibit high red‐shifted maximal absorption as compared with BP. ESR spectra indicate that PUIOA can generate free radicals most efficiently. Photopolymerization of the Polyurethane prepolymer, initiated by PUIOA, PUIO/MDEA, AAPBP/MDEA and BP/MDEA, was studied by photo‐DSC. The results show that PUIOA is the most efficient photoinitiator for PU prepolymer.Synthesis routes for polymeric photoinitiators.magnified imageSynthesis routes for polymeric photoinitiators.

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“…20 Moreover, there may undergo photolysis reaction at CAS bond as that in type I aside from Habstraction reaction, 21 which could greatly enhance the photoinitiating efficiency. [22][23][24] Yin et al [25][26][27] synthesized a series of macroinitiator bearing BP and sulfur. However, little work has been done for preparing hyperbranched polymeric BPs containing both amine and sulfur via thiol-ene click chemistry.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and photoinitiating activity study of polymeric photoinitiators bearing BP moiety based on hyperbranched poly(ester‐amine) via thiol‐ene click reaction

Xie

Shi

2011

J of Applied Polymer Sci

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A series of polymeric photoinitiators (BPHPEAs) bearing BP moiety based on hyperbranched poly(ester-amine) were synthesized via the thiol-ene click reaction of 3-(4-benzoylphenoxy)propyl 2-mercaptoacetate (BPPM) with acrylated HPEA. BPPM was obtained by the esterification of (4-(3-hydroxypropoxy) phenyl) phenyl methanone (HPPM) with mercaptoacetic acid in the presence of p-toluene sulphonic acid as a catalyst. HPEA was prepared through Michael addition of piperazine with tri(hydroxymethyl)propane triacrylate. Their molecular structures were confirmed by the 1 H NMR, 13 C NMR, and FTIR analysis. The UV-vis spectrum analysis results showed that BP-HPEAs exhibit the stronger n-p* absorption at $ 340 nm with over two times higher molar extinction coefficients than BP at the concentration of 1.00 Â 10 À3M. The photoinitiating activity study showed that the maximum photopolymerization rates of 1,6-hexanediol diacrylate initiated by BP-HPEAs in the absence of coinitiator were obtained by two times higher than that by BP in the presence of triethylamine as a coinitiator. Moreover, the excellent miscibility of BP-HPEAs with the commercial bisphenol A epoxy diacrylate was achieved according to the T s /T g ratios of over 9.0 from DMTA.

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Novel polymeric, thio‐containing photoinitiator comprising in‐chain benzophenone and an amine coinitiator for photopolymerization

Cited by 24 publications

References 47 publications

A Highly Efficient Polymerizable Photoinitiator Comprising Benzophenone, Thio Moieties, and N‐Arylmaleimide

A Highly Efficient Polymerizable Photoinitiator Comprising Benzophenone, Thio Moieties, and N‐Arylmaleimide

A Highly Efficient Polyurethane‐Type Polymeric Photoinitiator Containing In‐chain Benzophenone and Coinitiator Amine for Photopolymerization of PU Prepolymers

Synthesis and photoinitiating activity study of polymeric photoinitiators bearing BP moiety based on hyperbranched poly(ester‐amine) via thiol‐ene click reaction

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