4
5
R. S. Davidson, in Advances in Physical Chemistry, ed. D. Bethel and
V. Gold, Academic Press, London, 1983, p. 1.
A. Ledwith, J. A. Bosley and M. D. Purbrick, Exciplex interactions in
photoinitiation of polymerization by fluorenone-amine systems, J. Oil
Colour Chem. Assoc., 1978, 61, 95.
6
N. Arsu, R. Stephen Davidson and R. Holman, Factors affecting the
photoyellowing which occurs during the photoinitiated polymerization of
acrylates, J. Photochem. Photobiol., A, 1995, 87, 169.
7
8
9
W. N. Albrecht and R. L. Stephenson, Health hazards of tertiary amine
catalysts, Scand. J. Work, Environ. Health, 1988, 14, 209.
S. Shi, H. Gao, G. Wu and J. Nie, Cyclic acetal as coinitiator for bimole-
cular photoinitiating systems, Polymer, 2007, 48, 2860.
S. Shi and J. Nie, A natural component as coinitiator for unfilled dental
resin composites, J. Biomed. Mater. Res., Part B, 2007, 82B, 44.
1
0 S. Shi and J. Nie, Investigation of 3,4-methylenedioxybenzene methoxyl
methacrylate as coinitiator and comonomer for dental application,
J. Biomed. Mater. Res., Part B, 2007, 82B, 487.
11 S. Shi, P. Xiao, K. Wang, Y. Gong and J. Nie, Influence of chemical struc-
tures of benzodioxole-based coinitiators on the properties of the unfilled
dental resin, Acta Biomater., 2010, 6, 3067.
1
1
1
1
2 K. Wang, D. Yang, M. Xiao, X. Chen, F. Lu and J. Nie, Sesamin as a co-
initiator for unfilled dental restorations, Acta Biomater., 2009, 5, 2508.
3 C. Bandyopadhyay and P. S. Variyar, On the volatiles of pepper plant
Fig. 6 DC as a function of irradiation time of TPGDA bulk photopoly-
merizations initiated by 0.5 wt% BP in the presence of different
BDOOMe concentrations (0.1, 0.3, 1 and 2 wt%), I = 10 mW cm−
2
.
(Piper nigrum L.), PAFAI J. , 1988, 10, 25.
4 M. Tagashira and Y. Ohtake, A new antioxidative 1,3-benzodioxole from
Melissa officinalis, Planta Med., 1998, 64, 555.
5 Q. Hu, J. Xu, S. Chen and F. Yang, Antioxidant activity of extracts of
black sesame seed (Sesamum indicum L.) by supercritical carbon dioxide
extraction, J. Agric. Food Chem., 2004, 52, 943.
Conclusions
Three benzodioxole derivatives with different substituents were
synthesized in this work. The nature of the substituent had a
great influence on the initiating reactivity. The introduction of
electron-donating substituents at the 5-position of the phenyl .
ring contributed to an increase in the reactivity of the BP/benzodi-
oxole-based system, with the introduction of electron-withdrawing
substituents at the 5-position of the phenyl ring causing the oppo-
site effect. The kinetics were dependent on the chemical structure
of the benzodioxole and BP derivatives. Photopolymerization
occurred at the highest rate in the BP/BDOOMe system. In par-
ticular, the combination of CBP and BDOOMe showed the
highest initiating reactivity in the BP derivatives/BDOOMe
system. The addition of BDOOMe or an increase in light intensity
16 L. Jurd, V. L. Narayanan and K. D. Paull, In vivo antitumor activity of
-benzyl-1,3-benzodioxole derivatives against the P388, L1210, B16, and
6
M5076 murine models, J. Med. Chem., 1987, 30, 1752.
1
7 R. Joshi, M. S. Kumar, K. Satyamoorthy, M. K. Unnikrisnan and
T. Mukherjee, Free radical reactions and antioxidant activities of sesamol:
pulse radiolytic and biochemical studies, J. Agric. Food Chem., 2005, 53,
2
696.
8 E. Hodgson and R. M. Philpot, Interaction of methylenedioxyphenyl
1,3-benzodioxole) compounds with enzymes and their effects on
1
(
mammals, Drug Metab. Rev., 1974, 3, 231.
19 W. L. F. Armarego and C. L. L. Chai, Purification of Laboratory Chemi-
cals, Butterworth–Heinemann, London, 6th edn, 2009.
2
0 V. Bertini, M. Pocci, N. Picci, F. Lucchesini, A. Falbo and A. De Munno,
Synthesis of tailor-made copolymers containing 1,3-benzodioxole
systems for selective flocculation of minerals, J. Polym. Sci., Part A:
Polym. Chem., 1987, 25, 2665.
could both lead to an increase the values of R and DC for
p
2
1 H. H. Hussain, G. Babic, T. Durst, J. S. Wright, M. Flueraru,
A. Chichirau and L. L. Chepelev, Development of novel antioxidants:
design, synthesis, and reactivity, J. Org. Chem., 2003, 68, 7023.
2 J. W. Stansburya and S. H. Dickens, Determination of double bond conver-
sion in dental resins by nearinfrared spectroscopy, Dent. Mater., 2001, 17, 71.
3 S. Moon, Y. Kwon, J. Lee and J. Choo, Conformational stabilization of
1,3-benzodioxole: anomeric effect by natural bond orbital analysis,
J. Phys. Chem. A, 2001, 105, 3221.
TPGDA in photopolymerization. The relationship of Rpmax and the
intensity of incident light was in accordance with the photopoly-
merization rate equation (eqn (5)). The results indicated that
BDOOMe had the potential to be used as a coinitiator in the place
of amine in current BP/amine initiating systems in practical appli-
cations, potentially decreasing cytotoxicity and yellowing.
2
2
2
4 M. A. R. Matos, M. J. S. Monte, C. C. S. Sousa, A. R. R. P. Almeida and
V. M. F. Morais, Thermodynamic study of sesamol, piperonyl alcohol,
piperonylic acid and homopiperonylic acid: a combined experimental and
theoretical investigation, Org. Biomol. Chem., 2004, 2, 908.
5 M. A. R. Matos, C. C. S. Sousa and V. M. F. Morais, Experimental and
computational thermochemistry of 1,3-benzodioxole derivatives,
J. Chem. Eng. Data, 2007, 52, 1089.
Acknowledgements
2
2
2
The author would like to thank the National Natural Science
Foundation of China (20774010 and 21004047) for their
financial support. This study was also supported by Doctoral
Fund of Youth Scholars of Ministry of Education of China
6 E. Andrzejewska, G. L. Hug, M. Andrzejewski and B. Marciniak,
Trithianes as coinitiators in benzophenone-induced photopolymerizations,
Macromolecules, 1999, 32, 2173.
7 K. K. Dietliker, Chemistry and Technology of Uv and Eb Formulation for
Coatings, Inks and Paints, Volume 3: Photoinitiators for Free radical
and Cationic Polymerisation, SITATechnology, London, 1991.
8 J. F. Rabek, J. Polym. Sci., Part C: Polym. Lett., 1988, 26, 276–276.
9 N. S. Allen, Photochemistry and Photophysics of Polymer Materials,
Wiley, New York, 2010.
(No 20106101120005).
2
2
References
1
B. George and R. Dhamodharan, A study of the photopolymerization
kinetics of methyl methacrylate using novel benzophenone initiators,
Polym. Int., 2001, 50, 897.
30 G. Wu, S. Shi, P. Xiao and J. Nie, Synthesis and characterization of ali-
phatic amine co-initiator with different chain length for photopolymeriza-
tion of dimethacrylate, J. Photochem. Photobiol., A, 2007, 188, 260.
31 P. Xiao, S. Shi and J. Nie, Synthesis and characterization of copolymerizable
one-component type II photoinitiator, Polym. Adv. Technol., 2008, 19, 1305.
32 G. Odian, Principles of Polymerization, Wiley-Interscience, 4th edn, 2004.
2
3
J. P. Fouassier, Photoinitiation, Photopolymerization and Photocuring,
Hanser Verlag, Munich, 1995.
A. Ledwith and M. D. Purbrick, Initiation of free-radical polymerization
by photoinduced electron transfer processes, Polymer, 1973, 14, 521.
1382 | Photochem. Photobiol. Sci., 2012, 11, 1377–1382
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