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

doi:10.1007/s11706-009-0047-7

Front Mater Sci Chin

2009, Vol. 3

Issue (3) : 259-265 https://doi.org/10.1007/s11706-009-0047-7

RESEARCH ARTICLE

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

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

)

State Key Laboratory of Chemical Resource Engineering, Key Lab of Beijing City on Preparation and Processing of Novel Polymer Materials, Beijing University of Chemical Technology, Beijing 100029, China

Download: PDF(244 KB) HTML
Export: BibTeX | EndNote | Reference Manager | ProCite | RefWorks

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 (R_p) and the incident light intensity (I₀) was R_p∝I₀^0.5 and the maximum rate of polymerization (R_p,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 (T_g) of the curing product of AEBAC was about 80°C.

Keywords kinetics photopolymerization RTIR urethane diacrylate

Corresponding Author(s): NIE Jun,Email:niejun@mail.buct.edu.cn

Issue Date: 05 September 2009

Cite this article:

Ming XIAO,Ke-min WANG,Gui-ping MA, et al. Synthesis and photopolymerization of 2-(acryloyloxy) ethyl bis (2-(acryloyloxy) ethyl)carbamate[J]. Front Mater Sci Chin, 2009, 3(3): 259-265.

URL:

https://academic.hep.com.cn/foms/EN/10.1007/s11706-009-0047-7
https://academic.hep.com.cn/foms/EN/Y2009/V3/I3/259

Fig.1 Synthesis route of AEBAC

Fig.2 FTIR of AEBAC

Fig.3 Effect of the light intensity on photopolymerization of AEBAC ([1173] = 0.1 wt.%): the irradiation time dependence of the double bond conversion and ; the dependence of on the double bond conversion; the dependence of on the square root of the light intensity

Tab.1 Summary of kinetic results for AEBAC polymerization with various light intensities

Fig.4 Effect of photoinitiator concentration on photopolymerization of AEBAC (photoinitiator: 1173): the irradiation time dependence of the double bond conversion and ; the dependence of on the double bond conversion; the dependence of on the initiator concentration

Fig.5 Effect of initiator type on the photopolymerization of AEBAC

Fig.6 The temperature dependence of and tan for both AEBAC and TMPTA ([1173] = 1.0 wt.%)

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 doi: 10.1016/S0032-3861(02)00338-5
2	Assumptiona H J, Mathias L J. Photopolymerization of urethane dimethacrylates synthesized via a non-isocyanate route. Polymer , 2003, 44: 5131-5136 doi: 10.1016/S0032-3861(03)00530-5
3	Decker C. Photoinitiated crosslinking polymerization. Progress in Polymer Science , 1996, 21: 593-650 doi: 10.1016/0079-6700(95)00027-5
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 doi: 10.1016/j.polymdegradstab.2005.08.002
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 doi: 10.1016/j.porgcoat.2004.10.001
6	Parrish J P, Salvaore R N, Jung K W. Perspectives on alkyl carbonates in organic synthesis. Tetrahedron , 2000, 56: 8207-8237 doi: 10.1016/S0040-4020(00)00671-2
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 doi: 10.1016/S0040-4039(02)00435-5
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 doi: 10.1021/jo016075i
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 doi: 10.1016/j.cclet.2007.04.018
11	Shi S Q, Gao H, Wu G Q, . Cyclic acetal as coinitiator for bimolecular photoinitiating system. Polymer , 2007, 48(10): 2860–2865 doi: 10.1016/j.polymer.2007.03.027
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 doi: 10.1163/156855508X332522
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 doi: 10.1002/jbm.b.30754
14	He Y, Xiao M, Wu F P, . Photopolymerization kinetics of cycloaliphatic epoxide-acrylate hybrid monomer. Polymer International , 2007, 56: 1292-1297 doi: 10.1002/pi.2278
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 doi: 10.1002/pen.21029
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 doi: 10.1016/j.jphotochem.2007.07.003
17	Shi S Q, Nie J. Dimethacrylate based on cycloaliphatic epoxide for dental composite. Dental Materials , 2008, 24: 530-535 doi: 10.1016/j.dental.2007.05.018
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 doi: 10.1016/S0969-806X(99)00257-1
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 doi: 10.1002/pat.1132
21	Hill L W. Calculation of crosslink density in short chain network. Progress in Organic Coatings , 1997, 31: 235-243 doi: 10.1016/S0300-9440(97)00081-7

[1]	Huan-Yan XU, Yuan WANG, Tian-Nuo SHI, Hang ZHAO, Qu TAN, Bo-Chao ZHAO, Xiu-Lan HE, Shu-Yan QI. Heterogeneous Fenton-like discoloration of methyl orange using Fe₃O₄/MWCNTs as catalyst: kinetics and Fenton-like mechanism[J]. Front. Mater. Sci., 2018, 12(1): 34-44.
[2]	Inamullah MAITLO, Safdar ALI, Muhammad Yasir AKRAM, Farooq Khurum SHEHZAD, Jun NIE. Binary phase solid-state photopolymerization of acrylates: design, characterization and biomineralization of 3D scaffolds for tissue engineering[J]. Front. Mater. Sci., 2017, 11(4): 307-317.
[3]	Hui-Yun ZHOU,Pei-Pei CAO,Jie ZHAO,Zhi-Ying WANG,Jun-Bo LI,Fa-Liang ZHANG. Release behavior and kinetic evaluation of berberine hydrochloride from ethyl cellulose/chitosan microspheres[J]. Front. Mater. Sci., 2014, 8(4): 373-382.
[4]	Hui-Yun ZHOU, Ling-Juan JIANG, Yan-Ping ZHANG, Jun-Bo LI. β-Cyclodextrin inclusion complex: preparation, characterization, and its aspirin release in vitro[J]. Front Mater Sci, 2012, 6(3): 259-267.
[5]	Jing-Jun XU, Mei-Shuan LI, Xue-Liang FANG, Zhong-Wei ZHANG, Zheng-Hui XU, Jun-Shan WANG, . A novel ultra-high temperature oxidation technique in flowing gas with controlled oxygen partial pressure[J]. Front. Mater. Sci., 2010, 4(3): 266-270.
[6]	Ming-Tao RUN, Xin LI, Chen-Guang YAO, . Thermal degradation behavior and kinetic analysis of poly(L-lactide) in nitrogen and air atmosphere[J]. Front. Mater. Sci., 2010, 4(1): 78-83.
[7]	Ming-tao RUN, Zeng-kun WANG, Xin LI, Hong-chi ZHAO, . Crystal morphology, mechanical property and non-isothermal crystallization kinetics of poly(trimethylene terephthalate)/maleinized poly(ethylene-octene) copolymer binary blends[J]. Front. Mater. Sci., 2009, 3(4): 386-394.
[8]	LI Zai-feng, LI Jin-yan, SUN Jian, SUN Bao-qun, WANG Jin-jing, SHEN Qiang. Investigation of kinetics and morphology development for polyurethane-urea extended by DMTDA[J]. Front. Mater. Sci., 2008, 2(2): 200-204.
[9]	DAI Ming-zhi, XIAO Pu, NIE Jun. Synthesis and photopolymerization kinetics of a photoinitiator containing in-chain benzophenone and amine structure[J]. Front. Mater. Sci., 2008, 2(2): 194-199.
[10]	LI Zai-feng, LI Jin-yan, YUAN Wei, SUN Bao-qun, ZHANG Fu-tao, WANG Zeng-lin. Investigation of effects of dibutyltin dilaurate on reaction injection molding polyurethane-urea kinetics, morphology and mechanical properties by FTIR[J]. Front. Mater. Sci., 2008, 2(1): 99-104.
[11]	FANG Zhengping, WANG Jianguo, GU Aijuan, TONG Lifang. Curing behavior and kinetic analysis of epoxy resin/multi-walled carbon nanotubes composites[J]. Front. Mater. Sci., 2007, 1(4): 415-422.

Viewed

Full text

Abstract

Cited

Shared

Discussed