Cyclic acetals as the second co-initiators in three-component photoinitiating systems

Polymer Bulletin

Volumn 68, Issue 3, 2012, Pages 667-679

  Kabatc, Janina ^a  

^a UNIVERSITY OF TECHNOLOGY AND LIFE SCIENCES   (Poland)

Author keywords

Acetals; Electron transfer process; Free radical polymerization; Photoinitiators

Indexed keywords

ACETALS; CO-INITIATORS; CYANINE DYES; CYCLIC ACETALS; ELECTRON TRANSFER PROCESS; PHOTOINITIATING SYSTEMS; PHOTOINITIATORS; RATE OF POLYMERIZATION; THREE-COMPONENT; VISIBLE LIGHT;

DIFFERENTIAL SCANNING CALORIMETRY;

FREE RADICAL POLYMERIZATION;

EID: 84856597399     PISSN: 01700839     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00289-011-0565-1     Document Type: Article

References (42)

1. K Wang J Nie 2009 6-Benzoyl-1,3-benzodioxolane as a photoinitiator for free radical polymerization J Photochem Photobiol A Chem 204 7 12 1:CAS:528:DC%2BD1MXktlGltLY%3D
2. Fouassier JP (1995) Photoinitiation, photopolymerization, and photocurring: fundamentals and applications. Hanser, New York, pp 1-16
3. SC Clark CE Hoyle S Jonssonb F Morel DC Decker 1999 Photopolymerization of acrylates using N-aliphaticmaleimides as photoinitiators Polymer 40 5063 5072 1:CAS:528:DyaK1MXjs12ntLg%3D (Pubitemid 29339441)
4. R Kuhlmann W Schnabel 1976 Laser flash photolysis investigations on primary processes of the sensitized polymerization of vinyl monomers: 1. Experiments with benzophenone Polymer 17 419 422 1:CAS:528:DyaE28XkvFCksbs%3D
5. S Shi H Gao G Wu J Nie 2007 Cyclic acetal as coinitiator for bimolecular photoinitiating systems Polymer 48 2860 2865 1:CAS:528:DC%2BD2sXks12iu7w%3D (Pubitemid 46616897)
6. JP Fouassier D Ruhlmann B Graff Y Takimoto M Kawabata M Harada 1993 Visible light-induced polymerization reactions Imaging Sci Technol 37 208 210 1:CAS:528:DyaK3sXmtlOktrg%3D
7. J Jakubiak X Allonas JP Fouassier A Sionkowska E Andrzejewska LA Linden 2003 Photoinitiators for visible light polymerization Polymer 44 5219 5226 1:CAS:528:DC%2BD3sXlvVSnu7k%3D
8. S Suzuki P Emilie T Urano S Takahara T Yamaoka 2005 Three-component photo radical initiating system-the effect of 2-mercaptobenzothiazole as a co-initiator in polymer matrix Polymer 46 2238 2243 1:CAS:528: DC%2BD2MXhvVSlsbs%3D (Pubitemid 40311694)
9. E Andrzejewska D Zych-Tomkowiak M Andrzejewski GL Hug B Marciniak 2006 Heteroaromatic thiols as co-initiators for type II photoinitiating systems based on camphorquinone and isopropylthioxanthone Macromolecules 39 3777 3785 1:CAS:528:DC%2BD28XktVSlsLk%3D (Pubitemid 44013255)
10. J Geles 1981 The reactivity of cyclic acetals of aldoses and aldosides Adv Carbohydr Chem Biochem 39 71 156
11. T Ouchi M Hamad 1976 Cyclic acetal-photosensitized polymerization. II. Photopolymerization of styrene in the presence of various monocyclic acetals J Polym Sci A Polym Chem 14 2527 2533 1:CAS:528:DyaE28Xlslyjtb4%3D
12. R Mosca M Fagnoni M Melle M Albini 2001 Synthesis of monoprotected 1,4-diketones by photoinduced alkylation of enones with 2-substituted-1,3- dioxolanes Tetrahedron 57 10319 10328 1:CAS:528:DC%2BD3MXpt1GltL8%3D (Pubitemid 34008631)
13. S Shi J Nie 2007 A natural component as coinitiator for unfilled dental resin composites J Biomed Mater Res Appl Biomater 23 44 50 (Pubitemid 47015351)
14. D Elad RD Yousseyfyeh 1963 Catalytic rearrangement of cyclic acetals to carboxylic esters Tetrahedron Lett 30 2189
15. JP Fouassier F Morlet-Savary 1997 The role of the dye/iron arene complex/amine system as a photoinitiator for photopolymerization reactions Polymer 38 1415 1421 1:CAS:528:DyaK2sXhvFOhtrY%3D (Pubitemid 127409683)
16. KS Padon AB Scranton 2000 A mechanistic investigation of a three-component radical photoinitiator system comprising methylene blue, N-methyldiethanolamine, and diphenyliodonium chloride J Polym Sci A Polym Chem 38 2057 2066 1:CAS:528:DC%2BD3cXjsVaisbs%3D
17. Padon KS, Scranton AB (1999) In: Padalai GS (ed) Recent research developments in polymer science, vol 3. Transworld Research Network, Trivandrum, pp 369-385
18. Burged D, Grotzinger C, Fouassier JP (2001) In: Fouassier JP (ed) Light induced polymerization reactions. Trends in photochemistry and photobiology, vol 7. Trivandrum Research Trends, India, p 71
19. IR Gould D Shukla D Giesen S Farid 2001 Energetics of electron-transfer reactions of photoinitiated polymerization: dye-sensitized fragmentation of N-alkoxypyridinium salts Helv Chim Acta 83 2796 2812 (Pubitemid 33021574)
20. C Grotzinger D Burget P Jacques JP Fouassier 2003 Visible light induced photopolymerization: speeding up the rate of polymerization by using co-initiators in dye/amine photoinitiating systems Polymer 44 3671 3677 1:CAS:528:DC%2BD3sXkt1Wmu78%3D (Pubitemid 36648640)
21. JP Fouassier L Simonin-Catilaz 2001 Investigation of a system capable of photoinitiating radical polymerizations in thick pigmented media J Appl Polym Sci 79 1911
22. Z Kucybała A Kosobucka J Pa̧czkowski 2000 Development of new dyeing photoinitiators for free radical polymerization based on 3-methyl-1-phenyl-1H-pentaazacyclopenta[b]naphthalene skeleton. III J Photochem Photobiol A Chem 136 227 234
23. Z Kucybała J Pa̧czkowski 1999 3-Benzoyl-7-diethylamino-5- methyl-1-phenyl-1H-quinoxalin-2-one: an effective dyeing photoinitiator for free radical polymerization J Photochem Photobiol A Chem 128 135 138
24. J Kabatc B Jȩdrzejewska J Pa̧czkowski 2000 Kinetic study of free-radical polymerization photoinitiated by cyanine-borate salts. II J Polym Sci A Polym Chem 38 2365 2374 1:CAS:528:DC%2BD3cXmtFOqu7Y%3D
25. Z Kucybała J Pa̧czkowski 1993 Pyrazolono azomethine dyes as a effective photoinitiators of free radical polymerization Polymer 34 1558 1560
26. Pa̧czkowski J, Kabatc J, Jȩdrzejewska B (2008) Polymethine dyes as fluorescence probes and visible-light photoinitiators for free radical polymerization in heterocyclic polymethine dyes, synthesis, properties and application. In: Strekowski L (ed) Topics in heterocyclic chemistry, vol 14. Springer-Verlag, Berlin Heidelberg, pp 183-220
27. LA Linden J Pa̧czkowski JF Rabek 1999 Photodissociative and electron-transfer photoinitiators of radical polymerization Polymer 44 161 176 1:CAS:528:DyaK1MXit12itr8%3D
28. M Kawabata M Harada Y Takimoto 1988 Photoinduced electron transfer in the ion pair compound J Photopolym Sci Tech 1 222 227 1:CAS:528:DyaL1MXhvFentro%3D
29. Fouassier JP, Rabek JF (1992-1993) Radiation curing in polymer science and technology, vols 1-4. Plenum Press, New York
30. S Chatterjee P Gottschalk PD Davis GB Schuster 1988 Electron-transfer reactions in cyanine borate ion pairs: photopolymerization initiators sensitive to visible light J Am Chem Soc 110 2326 1:CAS:528:DyaL1cXhtlagtLk%3D
31. S Chatterjee PD Davis P Gottschalk B Kurz X Yang GB Schuster 1990 Photochemistry of carbocyanine alkyltriphenylborate salts: intra-ion-pair electron transfer and the chemistry of boranyl radicals J Am Chem Soc 112 6329 6338 1:CAS:528:DyaK3cXltFGgtbY%3D
32. LY Lan GB Schuster 1986 Free radical formation in the photooxidative alkylations of dicyanonaphthalene with alkyltriphenylborate salts Tetrahedron Lett 27 4261 1:CAS:528:DyaL2sXkt1aktLs%3D
33. V Malatesta KU Ingold 1981 Kinetic applications of electron paramagnetic resonance spectroscopy. 36. Stereoelectronic effects in hydrogen atom abstraction from ethers J Am Chem Soc 103 609 614 1:CAS:528:DyaL3MXhtVagt7w%3D
34. AJ Fielding P Franchi BP Roberts TM Smits 2002 Deoxygenation of tertiary and secondary alcohols ROH by thiol J Chem Soc Perkin Trans 2 155 163
35. JP Fouassier X Allonas J Lalevee M Visconti 2000 Polymeric Michler's ketone photoinitiator containing coinitiator amine J Polym Sci A Polym Chem 38 4531 4541 1:CAS:528:DC%2BD3cXos1Squ7g%3D
36. D Rehm A Weller 1969 Kinetik und Mechanismus der Elektronü mbertragung bei der Fluoreszenzlöschung in Acetonitril Ber Bunsen-Ges Phys Chem 73 834 1:CAS:528:DyaF1MXlt1eiu7w%3D
37. J Kabatc B Jȩdrzejewska J Pa̧czkowski 2000 Kinetic study of free radical polymerization photoinitiated by cyanine borate salts J Polym Sci A Polym Chem 28 2365 2374
38. J Kabatc M Pietrzak J Pa̧czkowski 1998 Cyanine borates revisited. Application of the Marcus equation for the description of the kinetics of photoinitiated free radical polymerization. IV Macromolecules 31 4651 4654 1:CAS:528:DyaK1cXktFWisLo%3D (Pubitemid 128567911)
39. J Kabatc M Pietrzak J Pa̧czkowski 2002 Cyanine borates revisited. Study of the kinetics of photoinitiated free radical polymerization via intermolecular electron transfer process. VI J Chem Soc Perkin Trans 2 2 287 295
40. K Kawamura 2004 Novel and efficient dye-linked radical generators for visible light photoinitiating polymerization J Photochem Photobiol A Chem 162 329 338 1:CAS:528:DC%2BD2cXhs1Cqu7Y%3D
41. J Kabatc J Pa̧czkowski 2009 N-Methylpicolinium derivatives as the coinitiators in photoinitiating systems for vinyl monomers polymerization J Polym Sci A Polym Chem 47 576 588 1:CAS:528:DC%2BD1MXmtFSgug%3D%3D
42. Dietliker K (1991) Chemistry and technology of uv and eb formulation for coating, inks and paints, volume III, photoinitiators for free radical and cationic polymerization. SITA Technology Ltd, London