journal article·2013-01

A benzophenone-bearing acid oligodimethacrylate and its application to the preparation of silver/gold nanoparticles/polymer nanocomposites

Emil C. Buruiana, Andreea Laura Chibac, Tinca Buruiana, Violeta Melinte, Lavinia Balan

Journal of Nanoparticle Research· Volume 15· Issue 1
Publisher page

Abstract

The synthesis of photosensitive urethane dimethacrylate that contains poly(ethylene oxide) sequence (PEG, M-w: 400), carboxylic and benzophenone moieties, and its characterization by specific methods (H-1 and C-13 NMR, FTIR, UV and electro-spray ionization-mass spectroscopy) are reported. UV curing parameters of this macromer (BP-UDMA) alone and in monomer combinations was evaluated through FTIR spectroscopy and photo-differential scanning calorimetry using 1 wt% 4-(dimethylamino)phenylacetic acid as co-initiator or Irgacure 819 (Irg819). The results show that the photopolymerization rates of the BP-UDMA are higher in the case of Irg819 (R-max(P) : 0.108 s(-1)) due to its synergic action, whereas the degree of conversion of C=C double bond (DC, after 120 s of UV irradiation) is over 77 %. When other co-monomers (non-acid urethane dimethacrylate and silyl urea methacrylate) are incorporated into the formulation, the photopolymerization rate (0.095-0.132 s(-1)) and DC (84.59-79.69 %) varied in reasonable limits. Depending of the photoinitiator type, as well as the monomer composition, the addition of 0.5, 1 and 3 wt% noble metal precursors (AgNO3 and AuBr3) led to the formation of hybrid composites with in situ-synthesized nanoparticles (NPs), where the variations in the intensity of the surface plasmon absorption bands appeared in the range 400-456 nm (Silver) or 500-553 nm (Gold), better results being obtained in the first initiating system. Homogeneous dispersion of nanoparticles into the polymer matrix was evidenced by EDX and TEM analysis, the last proving the existence of nanoparticles with sizes around 10 nm and variable morphologies. X-ray diffraction analysis complemented these results.
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Research context

OpenAlex topics: Photopolymerization techniques and applications · Photochromic and Fluorescence Chemistry

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References (53)

Show source-provided references
1. Arsu N, Reetz I, Yagci Y, Mishra MK (2009) Photoinitiated radical vinyl polymerization. In: Mishra MK, Yagci Y (eds) Handbook of vinyl polymers: radical polymerization, process, and technology, 2nd edn. CRC, Boca Raton, pp 141–204
2. Balan L, Jin M, Malval JP, Chaumeil H, Defoin A, Vidal L (2008) Fabrication of silver nanoparticle-embedded polymer promoted by combined photochemicalp of a 2,7-diaminofluorene derivative dye. Macromolecules 41:9359–9365. doi: 10.1021/ma801792610.1021/ma8017926 ↗
3. Balan L, Malval JP, Schneider R, Le Nouen D, Lougnot DJ (2010) In situ fabrication of polyacrylate–silver nanocomposite through photoinduced tandem reactions involving eosin dye. Polymer 51:1363–1369. doi: 10.1016/j.polymer.2009.05.00310.1016/j.polymer.2009.05.003 ↗
4. Bauer F, Flyunt R, Czihal K, Buchmeiser MR, Langguth H, Mehnert R (2006) Nano/micro particle hybrid composites for scratch and abrasion resistant polyacrylate coatings. Macromol Mater Eng 291:493–498. doi: 10.1002/mame.20060003410.1002/mame.200600034 ↗
5. Bowman CN, Kloxin CJ (2008) Toward an enhanced understanding and implementation of photopolymerization reactions. AIChE J 54:2775–2795. doi: 10.1002/aic.1167810.1002/aic.11678 ↗
6. Buruiana T, Melinte V, Chibac A, Matiut S, Balan L (2012a) Synthesis, evaluation and preliminary antibacterial testing of hybrid composites based on urethane oligodimethacrylates and Ag nanoparticles. J Biomater Sci Polym Ed 23:955–972. doi: 10.1163/092050611X56680110.1163/092050611X566801 ↗
7. Buruiana T, Melinte V, Jitaru F, Buruiana EC, Balan L (2012b) Preparation of siloxane-based urethane dimethacrylates carrying carboxylic groups and the effect of silver nanoparticles on the properties of composite polymer films. J Polym Sci Part A 50:874–883. doi: 10.1002/pola.2583910.1002/pola.25839 ↗
8. Chibac A, Melinte V, Buruiana T, Balan L, Buruiana EC (2012) One-pot synthesis of photocrosslinked sol-gel hybrid composites containing silver nanoparticles in urethane-acrylic matrixes. Chem Eng J 200–202:577–588. doi: 10.1016/j.cej.2012.06.11010.1016/j.cej.2012.06.110 ↗
9. Chung MH, Lin JS, Hsieh TE, Chen NP, Juang FS, Chen CM, Liu LC (2011) Preparation of organic/inorganic hybrid nanocomposites by ultraviolet irradiation and their packaging applications for organic optoelectronic devices. Appl Surf Sci 257:9142–9151. doi: 10.1016/j.apsusc.2011.05.11710.1016/j.apsusc.2011.05.117 ↗
10. Corrales T, Catalina F, Peinado C, Allen NS, Rufs AM, Bueno C, Encinas MV (2002) Photochemical study and photoinitiation activity of macroinitiators based on thioxanthone. Polymer 43:4591–4597. doi: 10.1016/S0032-3861(02)00310-510.1016/S0032-3861(02)00310-5 ↗
11. Do HS, Park YJ, Kim HJ (2006) Preparation and adhesion performance of UV-crosslinkable acrylic pressure sensitive adhesives. J Adhesion Sci Technol 20:1529–1545. doi: 10.1163/15685610677866646210.1163/156856106778666462 ↗
12. Esposito Corcione C, Frigione M (2012) UV-cured polymer-boehmite nanocomposite as protective coating for wood elements. Progr Org Coat 74:781–787. doi: 10.1016/j.porgcoat.2011.06.02410.1016/j.porgcoat.2011.06.024 ↗
13. Fan H, Chen Z, Brinker J, Clawson J, Alam T (2005) Synthesis of organo-silane functionalized nanocrystal micelles and their self-assembly. J Am Chem Soc 127:13746–13747. doi: 10.1021/ja053795o10.1021/ja053795o ↗
14. Foos EE, Snow AW, Twigg ME, Ancona MG (2002) Thiol-terminated di-, tri-, and tetraethylene oxide functionalized gold nanoparticles: a water-soluble, charge-neutral cluster. Chem Mater 14:2401–2408. doi: 10.1021/cm020007a10.1021/cm020007a ↗
15. Fouassier JP (1995) Photoinitiation, photopolymerization and photocuring. Fundamentals and applications. Hanser, Munich
16. Fouassier JP, Allonas X, Lalevée J, Dietlin C (2010) Photoinitiators for free radical polymerization reactions. In: Allen NS (ed) Photochemistry and photophysics of polymer materials. Wiley, Hoboken, pp 351–41910.1002/9780470594179.ch10 ↗
17. Frenkel AI, Nemzer S, Pister I, Harris T, Sun Y, Rafailovich MH (2005) Size-controlled synthesis and characterization of thiol-stabilized gold nanoparticles. J Chem Phys 123:184701. doi: 10.1063/1.212666610.1063/1.2126666 ↗
18. Gaharwar AK, Dammu SA, Canter JM, Wu CJ, Schmidt G (2011) Highly extensible, tough, and elastomeric nanocomposite hydrogels from poly(ethylene glycol) and hydroxyapatite nanoparticles. Biomacromolecules 12:1641–1650. doi: 10.1021/bm200027z10.1021/bm200027z ↗
19. Jauk S, Liska R (2005) Photoinitiators with functional groups, 8a benzophenone with covalently bound phenylglycine. Macromol Rapid Commun 26:1687–1692. doi: 10.1002/marc.20050050710.1002/marc.200500507 ↗
20. Jiang X, Yin J (2004) Polymeric photoinitiator containing in-chain thioxanthone and coinitiator amines. Macromol Rapid Commun 25:748–752. doi: 10.1002/marc.20030027010.1002/marc.200300270 ↗
21. Jiang X, Luo X, Yin J (2005) Polymeric photoinitiators containing in-chain benzophenone and coinitiators amine: effect of the structure of coinitiator amine on photopolymerization. J Photochem Photobiol A 174:165–170. doi: 10.1016/j.jphotochem.2005.02.00810.1016/j.jphotochem.2005.02.008 ↗
22. Jiang G, Wang L, Chen W (2007) Studies on the preparation and characterization of gold nanoparticles protected by dendrons. Mater Lett 61:278–283. doi: 10.1016/j.matlet.2006.04.11010.1016/j.matlet.2006.04.110 ↗
23. Kilambi H, Stansbury JW, Bowman CN (2007) Deconvoluting the impact of intermolecular and intramolecular interactions on the polymerization kinetics of ultrarapid mono(meth)acrylates. Macromolecules 40:47–54. doi: 10.1021/ma061983910.1021/ma0619839 ↗
24. Kim JH, Min BR, Won J, Kang YS (2006) Effect of the polymer matrix on the formation of silver nanoparticles in polymer–silver salt complex membranes. J Polym Sci Part B 44:1168–1178. doi: 10.1002/polb.2077710.1002/polb.20777 ↗
25. Kou Y, Wang J, Lv M, Jian X (2010) Preparation and evaluation of epoxy methacrylate UV-curable coatings containing phthalazinone. Polym Int 59:107–111. doi: 10.1002/pi.269710.1002/pi.2697 ↗
26. Melinte V, Buruiana T, Balan L, Buruiana EC (2012) Photocrosslinkable acid urethane dimethacrylates from renewable natural oil and their use in the design of silver/gold polymeric nanocomposites. React Funct Polym 72:252–259. doi: 10.1016/j.reactfunctpolym.2012.01.00410.1016/j.reactfunctpolym.2012.01.004 ↗
27. Nayak BR, Mathias LJ (2005) A novel photoinimer for the polymerization of acrylates and methacrylates. J Polym Sci Part A 43:5661–5670. doi: 10.1002/pola.2105110.1002/pola.21051 ↗
28. Ninjbadgar T, Garnweitner G, Borger A, Goldenberg LM, Sakhno OV, Stumpe J (2009) Synthesis of luminescent ZrO2:Eu3+ nanoparticles and their holographic sub-micrometer patterning in polymer composites. Adv Funct Mater 19:1819–1825. doi: 10.1002/adfm.20080183510.1002/adfm.200801835 ↗
29. Omura K, Tomita Y (2010) Photopolymerization kinetics and volume holographic recording in ZrO2 nanoparticle-polymer composites at 404 nm. J Appl Phys 107:023107. doi: 10.1063/1.328972910.1063/1.3289729 ↗
30. Sadat-Shojai M, Atai M, Nodehi A, Nasiri Khanlar L (2010) Hydroxyapatite nanorods as novel fillers for improving the properties of dental adhesives: synthesis and application. Dent Mater 26:471–482. doi: 10.1016/j.dental.2010.01.00510.1016/j.dental.2010.01.005 ↗
31. Sakamoto M, Fujistuka M, Majima T (2009) Light as a construction tool of metal nanoparticles: synthesis and mechanism. J Photochem Photobiol C 10:33–56. doi: 10.1016/j.jphotochemrev.2008.1100210.1016/j.jphotochemrev.2008.11.002 ↗
32. Sangermano M, Lak N, Malucelli G, Samakande A, Sanderson RD (2008a) UV-curing and characterization of polymer–clay nanocoatings by dispersion of acrylate-funtionalized organoclays. Progr Org Coat 61:89–94. doi: 10.1016/j.porgcoat.2007.09.00910.1016/j.porgcoat.2007.09.009 ↗
33. Sangermano M, Marchino A, Perruchas S, Gacoin T, Rizza G (2008b) UV-cured nanostructured gold/acrylic coating. Macromol Mater Eng 293:964–968. doi: 10.1002/mame.20080020110.1002/mame.200800201 ↗
34. Sangermano M, Vescovo L, Pepino N, Chiolerio A, Allia P, Tiberto P, Coisson M, Suber L, Marchegiani G (2010) Photoinitiator-free UV-cured acrylic coatings containing magnetite nanoparticles. Macromol Chem Phys 211:2530–2535. doi: 10.1002/macp.20100044410.1002/macp.201000444 ↗
35. Stamplecoskie KG, Scaiano JC (2010) Light emitting diode irradiation can control the morphology and optical properties of silver nanoparticles. J Am Chem Soc 132:1825–1827. doi: 10.1021/ja910010b10.1021/ja910010b ↗
36. Sun ZB, Dong XZ, Chen WQ, Nakanishi S, Duan XM, Kawata S (2008) Multicolor polymer nanocomposites: in situ synthesis and fabrication of 3D microstructures. Adv Mater 20:914–919. doi: 10.1002/adma.20070203510.1002/adma.200702035 ↗
37. Sun K, Qiu J, Liu J, Miao Y (2009) Preparation and characterization of gold nanoparticles using ascorbic acid as reducing agent in reverse micelles. J Mater Sci 44:754–758. doi: 10.1007/s10853-008-3162-410.1007/s10853-008-3162-4 ↗
38. Suyama K, Miyamoto Y, Matsuoka T, Wada S, Tsunooka M (2000) Photo-initiated thermal crosslinking of copolymers bearing pendant base generating groups. Polym Adv Technol 11:589–596. doi: 10.1002/1099-1581(200008/12)11:8/12<589:AID-PAT49>3.0.CO;2-C10.1002/1099-1581(200008/12)11:8/12<589::AID-PAT49>3.0.CO;2-C ↗
39. Tasdelen MA, Kumbaraci V, Talinli N, Yagci Y (2006) Photochemically masked benzophenone: photoinitiated free radical polymerization by using benzodioxinone. Polymer 47:7611–7614. doi: 10.1016/j.polymer.2006.09.02010.1016/j.polymer.2006.09.020 ↗
40. Temel G, Karaca N, Arsu N (2010) Synthesis of main chain polymeric benzophenone photoinitiator via thiol-ene click chemistry and its use in free radical polymerization. J Polym Sci Part A 48:5306–5312. doi: 10.1002/pola.2433010.1002/pola.24330 ↗
41. Uygun M, Kahveci MU, Odaci D, Timur S, Yagci Y (2009) Antibacterial acrylamide hydrogels containing silver nanoparticles by simultaneous photoinduced free radical polymerization and electron transfer processes. Macromol Chem Phys 210:1867–1875. doi: 10.1002/macp.20090029610.1002/macp.200900296 ↗
42. Valderas C, Bertolotti S, Previtali CM, Encinas MV (2002) Influence of the amine structure on the polymerization of methyl methacrylate photoinitiated by aromatic ketone/amine. J Polym Sci Part A 40:2888–2893. doi: 10.1002/pola.1038210.1002/pola.10382 ↗
43. Wang H, Wei J, Jiang X, Yin J (2006a) Novel chemical-bonded polymerizable sulfur-containing photoinitiators comprising the structure of planar N-phenylmaleimide and benzophenone for photopolymerization. Polymer 47:4967–4975. doi: 10.1016/j.polymer.2006.04.02710.1016/j.polymer.2006.04.027 ↗
44. Wang AL, Yin HB, Red M, Cheng XN, Zhod QF, Zhang XF (2006b) Effects of different functional group-containing organics on morphology-controlled synthesis of silver nanoparticles at room temperature. Acta Metall Sin (Engl Lett) 19:362–370. doi: 10.1016/S1006-7191(06)62074-710.1016/S1006-7191(06)62074-7 ↗
45. Wang Y, Betts DE, Finlay JA, Brewer L, Callow ME, Callow JA, Wendt DE, DeSimone JM (2011) Photocurable amphiphilic perfluoropolyether/poly(ethylene glycol) networks for fouling-release coatings. Macromolecules 44:878–885. doi: 10.1021/ma102271t10.1021/ma102271t ↗
46. Wei J, Liu F (2009) Novel highly efficient macrophotoinitiator comprising benzophenone, coinitiator amine, and thio moieties for photopolymerization. Macromolecules 42:5486–5491. doi: 10.1021/ma900887h10.1021/ma900887h ↗
47. Wei J, Wang H, Jiang X, Yin J (2006) Effect on photopolymerization of the structure of amine coinitiators contained in novel polymeric benzophenone photoinitiators. Macromol Chem Phys 207:1752–1763. doi: 10.1002/macp.20060027410.1002/macp.200600274 ↗
48. Wei J, Wang H, Yin J (2007) Novel polymeric, thio-containing photoinitiator comprising in-chain benzophenone and an amine coinitiator for photopolymerization. J Polym Sci Part A 45:576–587. doi: 10.1002/pola.2181810.1002/pola.21818 ↗
49. Wright J, Ivanova E, Pham D, Filiponi L, Viezzoli A, Suyama K, Shirai M, Tsunooka M, Nicolay DV (2003) Positive and negative tone protein patterning on a photobase generating polymer. Langmuir 19:446–452. doi: 10.1021/la026123+10.1021/la026123+ ↗
50. Yagci Y (2012) New photoinitiating systems designed for polymer/inorganic hybrid nanocoatings. J Coat Technol Res 9:125–134. doi: 10.1007/s11998-009-9219-810.1007/s11998-009-9219-8 ↗
51. Yagci Y, Jockusch S, Turro NJ (2010) Photoinitiated polymerization: advances, challenges, and opportunities. Macromolecules 43:6245–6260. doi: 10.1021/ma100754510.1021/ma1007545 ↗
52. Zan X, Kozlov M, McCarthy TJ, Su Z (2010) Covalently attached, silver-doped poly(vinyl alcohol) hydrogel films on poly(l-lactic acid). Biomacromolecules 11:1082–1088. doi: 10.1021/bm100048q10.1021/bm100048q ↗
53. Zytowschi T, Fischer H (1996) Absolute rate constants for the addition of methyl radicals to alkenes in solution: new evidence for polar interactions. J Am Chem Soc 118:437–439. doi: 10.1021/ja953085q10.1021/ja953085q ↗