Synthesis and photopolymerization of 2-(acryloyloxy) ethyl bis (2-(acryloyloxy) ethyl)carbamate

Ming XIAO, Ke-min WANG, Gui-ping MA, Jun NIE

PDF(244 KB)
PDF(244 KB)
Front. Mater. Sci. ›› 2009, Vol. 3 ›› Issue (3) : 259-265. DOI: 10.1007/s11706-009-0047-7
RESEARCH ARTICLE
RESEARCH ARTICLE

Synthesis and photopolymerization of 2-(acryloyloxy) ethyl bis (2-(acryloyloxy) ethyl)carbamate

Author information +
History +

Abstract

A low viscosity urethane diacrylate monomer of 2-(acryloyloxy) ethyl bis (2-(acryloyloxy) ethyl)carbamate (AEBAC) was prepared via a nonisocyanate route. The photopolymerization kinetics of this urethane acrylate was studied by real-time FTIR. The influences of light intensity, photoinitiator type, and concentration on the polymerization kinetics were discussed. The photopolymerization kinetic results indicated that the relationship between the polymerization rate (Rp) and the incident light intensity (I0) was RpI00.5 and the maximum rate of polymerization (Rp,max) was proportional to [A]0.5 ([A] was the molar concentration of initiator). The dynamic mechanical analysis (DMA) results indicated that the glass transition temperature (Tg) of the curing product of AEBAC was about 80°C.

Keywords

kinetics / photopolymerization / RTIR / urethane diacrylate

Cite this article

Download citation ▾
Ming XIAO, Ke-min WANG, Gui-ping MA, Jun NIE. Synthesis and photopolymerization of 2-(acryloyloxy) ethyl bis (2-(acryloyloxy) ethyl)carbamate. Front Mater Sci Chin, 2009, 3(3): 259‒265 https://doi.org/10.1007/s11706-009-0047-7

References

[1]
Peinado C, Alonso A, Salvador E F, . Following in situ photoinitiated polymerization of multifunctional acrylic monomers by fluorescence and photocalorimetry simultaneously. Polymer, 2002, 43: 5355-5361
CrossRef Google scholar
[2]
Assumptiona H J, Mathias L J. Photopolymerization of urethane dimethacrylates synthesized via a non-isocyanate route. Polymer, 2003, 44: 5131-5136
CrossRef Google scholar
[3]
Decker C. Photoinitiated crosslinking polymerization. Progress in Polymer Science, 1996, 21: 593-650
CrossRef Google scholar
[4]
Lee B H, Kim H J. Influence of isocyanate type of acrylated urethane oligomer and of additives on weathering of UV-cured films. Polymer Degradation and Stability, 2006, 91: 1025-1035
CrossRef Google scholar
[5]
Xu G, Shi W F. Synthesis and characterization of hyperbranched polyurethane acrylates used as UV curable oligomers for coatings. Progress in Organic Coatings, 2005, 52: 110-117
CrossRef Google scholar
[6]
Parrish J P, Salvaore R N, Jung K W. Perspectives on alkyl carbonates in organic synthesis. Tetrahedron, 2000, 56: 8207-8237
CrossRef Google scholar
[7]
Uriz P, Serra M, Castillon S, . An efficient diastereoselective one-pot synthesis of dihydrofuro[2′,3′:2,3]indeno[2,1-b]furan derivatives. Tetrahedron Letters, 2002, 43: 2927–2929
CrossRef Google scholar
[8]
Clark A J, Echenique J, Haddleton D M, . A nonisocyanate route to monodisperse branched polyurethanes. The Journal of Organic Chemistry, 2001, 66(25): 8687-8689
CrossRef Google scholar
[9]
Shi S Q, Nie J. A natural component as coinitiator for unfilled dental resin composites. Journal of Biomedical Materials Research Par B: Applied Biomaterials, 2007, 82B(1): 44–50
[10]
Shi S Q, Gao H, Nie J. A natural component as initiator for photopolymerization of 1, 6-hexanedioldiacrylate. Chinese Chemical Letters, 2007, 18: 750-753
CrossRef Google scholar
[11]
Shi S Q, Gao H, Wu G Q, . Cyclic acetal as coinitiator for bimolecular photoinitiating system. Polymer, 2007, 48(10): 2860–2865
CrossRef Google scholar
[12]
Xiao M, He Y, Nie J. Novel bisphenol A epoxide-acrylate hybrid oligomer and its photopolymerization. Designed Monomers and Polymers, 2008, 11: 383-394
CrossRef Google scholar
[13]
Shi S Q, Nie J. Investigation of 3,4-methylenedioxybenzene methoxyl methacrylate as coinitiator and comonomer for dental application. Journal of Biomedical Materials Research Part B: Applied Biomaterials, 2007, 82B: 487-493
CrossRef Google scholar
[14]
He Y, Xiao M, Wu F P, . Photopolymerization kinetics of cycloaliphatic epoxide-acrylate hybrid monomer. Polymer International, 2007, 56: 1292-1297
CrossRef Google scholar
[15]
Xiao P, Wang Y, Dai M Z, . Synthesis and photopolymerization kinetics of polymeric one-compponent type II photoinitiator containing benzophenone moiety and tertiary amine. Polymer Engineering & Science, 2008, 48: 884-888
CrossRef Google scholar
[16]
Xu H G, Wu G Q, Nie J. Synthesis and photopolymerization characteristics of amine coinitiator. Journal of Photochemistry and Photobiology A: Chemistry, 2008, 193: 254-259
CrossRef Google scholar
[17]
Shi S Q, Nie J. Dimethacrylate based on cycloaliphatic epoxide for dental composite. Dental Materials, 2008, 24: 530-535
CrossRef Google scholar
[18]
Scherzer T, Decker U. Kinetic investigations on the UV-induced photopolymerization of a diacrylate by time-resolved FTIR spectroscopy: the influence of photoinitiator concentration, light intensity and temperature. Radiation Physics and Chemistry, 1999, 55(5–6): 615–619
CrossRef Google scholar
[19]
Odian G. Principles of Polymerizatio (3rd ed). New York: John Wiley & Sons, Inc, 1991
[20]
Xiao P, Shi S Q, Nie J. Synthesis and characterization of copolymerizable one-component type II photoinitiator. Polymers for Advanced Technologies, 2008, 19(9): 1305–1310
CrossRef Google scholar
[21]
Hill L W. Calculation of crosslink density in short chain network. Progress in Organic Coatings, 1997, 31: 235-243
CrossRef Google scholar

RIGHTS & PERMISSIONS

2014 Higher Education Press and Springer-Verlag Berlin Heidelberg
AI Summary AI Mindmap
PDF(244 KB)

Accesses

Citations

Detail

Sections
Recommended

/