Citation: ZHOU Yanfang, ZENG Ze, XIE Gang, JIAO Chenjie, ZHOU Yubing, ZHONG Rong. Synthesis and Photoinitiation Properties of Pentaerythritol Tetrabenzoyl Formate[J]. Chinese Journal of Applied Chemistry, ;2018, 35(6): 652-658. doi: 10.11944/j.issn.1000-0518.2018.06.170228 shu

Synthesis and Photoinitiation Properties of Pentaerythritol Tetrabenzoyl Formate

  • Corresponding author: ZHONG Rong, zhongr@nchu.edu.cn
  • Received Date: 26 June 2017
    Revised Date: 15 September 2017
    Accepted Date: 5 December 2017

    Fund Project: Supported by the National Natural Science Foundation of China(No.21364008), the Science and Technology Conditions Platform Special Construction Funds in Jiangxi Province(No.20164BCD40098)the National Natural Science Foundation of China 21364008the Science and Technology Conditions Platform Special Construction Funds in Jiangxi Province 20164BCD40098

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  • The limit of small molecule photoinitiators to applications of food and medical materials due to the toxicity of its residual fragments can be solved by the macromolecular photoinitiators. In this paper, pentaerythritol tetrahydrobenzoylformate(PTF) was synthesized using benzoyl formic acid(BF) and pentaerythritol(PET) as raw materials by acid chloride method. The results of thermal analysis show that there is 15% mass loss at 225℃ for PTF and its thermal stability is better than that of 2-hydroxy-2-methyl-1-phenyl-1-propanone(1173 photoinitiator). The initial decomposition temperature and the temperature with the same mass loss for the photocurable coatings using PTF as the photoinitiator are 100℃ higher than those for coatings using 1173 photoinitiator. The results show that the maximum reaction rate is 0.037 s-1, the final double bond conversion is 39.5%, and PTF has higher photoinduced activity than 1173 in the trimethylolpropane triacrylate(TMPTA) polymerization by light-differential scanning calorimetry. The residue content of PTF is only 5% of that of 1173 photoinitiator under the same experimental conditions.
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    1. [1]

      Liu K, Su Z G, Miao S D. UV-curable Enzymatic Antibacterial Waterborne Polyurethane Coating[J]. Biochem Eng J, 2016,113:107-113. doi: 10.1016/j.bej.2016.06.004

    2. [2]

      Roth M, Hennen D, Oesterreicher A. Exploring Functionalized Benzophenones as Low-migration Photoinitiators for Vinyl Carbonate/Thiol Formulations[J]. Eur Polym J, 2017,88:403-411. doi: 10.1016/j.eurpolymj.2016.11.004

    3. [3]

      Zhang Y, Du Z X, Xia X M. Evaluation of the Migration of UV-ink Photoinitiators from Polyethylene Food Packaging by Supercritical Fuid Chromatography Combined with Photodiode Array Detector and Tandem Mass Spectrometry[J]. Polym Test, 2016,53:276-282. doi: 10.1016/j.polymertesting.2016.06.008

    4. [4]

      Wang K M, Yang K, Yu Q. Novel Polymeric Photoinitiators with Side-chain Benzophenone:Facile Synthesis and Photopolymerization Properties Without Coinitiator[J]. Prog Org Coat, 2014,77:1929-1934. doi: 10.1016/j.porgcoat.2014.06.026

    5. [5]

      Jing C, Ding G, Qin X Z. New Near UV Photoinitiators Containing Benzophenone Part for Photoinitiating Polymerization of Methyl Methacrylate[J]. Prog Org Coat, 2017,110:150-161. doi: 10.1016/j.porgcoat.2017.04.038

    6. [6]

      Valdesueiro D, Hettinga H, Drijfhout J P. Tuning Roughness and Gloss of Powder Coating Paint by Encapsulating the Coating Particles with Thin Al2O3 Films[J]. Powder Technol, 2017,318:401-410. doi: 10.1016/j.powtec.2017.05.019

    7. [7]

      Xu Y J, Wang Q, Cao Y F. Preparation of a Reduced Graphene Oxide/SiO2/Fe3O4 UV-curing Material and Its Excellent Microwave Absorption Properties[J]. RSC Adv, 2017,7:18172-18177. doi: 10.1039/C7RA01338H

    8. [8]

      Al-Shroofy M, Zhang Q L, Xu J. Solvent-free Dry Powder Coating Process for Low-Cost Manufacturing of LiNi1/3Mn1/3Co1/3O2 Cathodes in Lithium-Ion Batteries[J]. J Power Sources, 2017,352:187-193. doi: 10.1016/j.jpowsour.2017.03.131

    9. [9]

      Dai J Y, Ma S Q, Wu Y G. High Bio-based Content Waterborne UV-curable Coatings with Excellent Adhesion and Flexibility[J]. Prog Org Coat, 2015,87:197-203. doi: 10.1016/j.porgcoat.2015.05.030

    10. [10]

      Aznar M, Domeno C, Nerín C. Set-off of Non Volatile Compounds from Printing Inks in Food Packaging Materials and the Role of Lacquers to Avoid Migration[J]. Dyes Pigm, 2015,114:85-92. doi: 10.1016/j.dyepig.2014.10.019

    11. [11]

      ZHANG Jielong, LEI Jinhai. Preparation and Application of Benzoylformic Acid[J]. J Zhejiang Chem Ind, 2008,39(12):13-15. doi: 10.3969/j.issn.1006-4184.2008.12.006

    12. [12]

      CHEN Yinxia, YANG Guozhong, LI Jing. Synthesis and Application of Methyl Benzoylformate[J]. Fine Spec Chem, 2014,22(11):40-43. doi: 10.3969/j.issn.1008-1100.2014.11.009

    13. [13]

      Sun Y J, Wang X P, Wang D B. Measurement and Correlation for Phase Equilibrium of HFO1234yf with Three Pentaerythritol Esters from 293.15 K to 348.15 K[J]. J Chem Thermodyn, 2017,112:122-128. doi: 10.1016/j.jct.2017.04.020

    14. [14]

      Hwang H D, Park C H, Moon J I. UV-curing Behavior and Physical Properties of Waterborne UV-curable Polycarbonatebased Polyurethane Dispersion[J]. Prog Org Coat, 2011,72:663-675. doi: 10.1016/j.porgcoat.2011.07.009

    15. [15]

      WEI Yuli, WANG Yunpu, CHANG Yue. Preparation and Characterization of Pentaerythritol Tetramethacrylate[J]. J Northwest Nor Univ (Nat Sci Edit), 2007,43(5):63-66.  

    16. [16]

      Llorente O, Fernández-Berridi M J, González A. Study of the Crosslinking Process of Waterborne UV Curable Polyurethane Acrylates[J]. Prog Org Coat, 2016,99:437-442. doi: 10.1016/j.porgcoat.2016.06.020

    17. [17]

      Han X, Hu L H, Zhang Y. Sulfur-containing Hyperbranched Polymeric Photoinitiator End-capped with Benzophenone and Tertiary Amine Moieties Prepared via Simultaneous Double Thiol-ene Click Reactions Used for UV Curing Coatings[J]. Prog Org Coat, 2011,72:572-578. doi: 10.1016/j.porgcoat.2011.06.020

    18. [18]

      Hu S K, Wu X S, Neckers D C. Methyl Phenylglyoxylateasa Photointiator[J]. Macromolecule, 2000,33(11):4030-4033. doi: 10.1021/ma992100z

    19. [19]

      Winffied L, Andrsas W, Wiffied D, et al. Process for the Preparation of Phenylglyoxylic Acid Esters: US 4596885.

    20. [20]

      SUN Jian, ZHENG Kangjian. A Preparation Method of Phenylglyoxylic Acid Ester Photoinitiator: CN, 201510059315. 8(in Chinese).

    21. [21]

      HE Chuhua, FU Shifu, LIU Chuanxiang. Synthesis of Dipentaerythritol Hexaacrylate by Acid Chloride Method[J]. J Chem Ind, 2003,17(4):45-46.  

    22. [22]

      Zhang Y, Du Z X, Xia X M. Evaluation of the Migration of UV-ink Photoinitiators from Polyethylene Food Packaging by Supercritical Fluid Chromatography Combined with Photodiode Array Detector and Tandem Mass Spectrometry[J]. Polym Test, 2016,53:276-282. doi: 10.1016/j.polymertesting.2016.06.008

    23. [23]

      Papilloud S, Baudraz D. Migration Tests for Substrates Printed with UV Ink Systems in Aqueous Simulants[J]. Prog Org Coat, 2002,45:231-237. doi: 10.1016/S0300-9440(02)00040-1

    24. [24]

      Hoeck E V, Schaetzen T D, Pacquet C. Analysis of Benzophenone and 4-Methylbenzophenone in Breakfast Cereals Using Ultrasonic Extraction in Combination with Gas Chromatography Tandem Mass Spectrometry(GC MSn)[J]. Anal Chem Acta, 2010,663:55-59. doi: 10.1016/j.aca.2010.01.044

    25. [25]

      JIANG Pingkai, WANG Zongguang, WANG Shoutai. Tudy on the Relation Between the Torque of Silanegrafting Polyethylenes and Gel Fraction[J]. Polym Mater Sci Eng, 2000,16(1):89-91.  

    26. [26]

      YAN Jinrong. Study on the Methods to Test for Gelling Percent of Silane Crosslinked Polyethylene[J]. Plast Sci Tech, 2002,2:62-64. doi: 10.3969/j.issn.1005-3360.2002.02.018

    27. [27]

      Cheng L L, Shi W F. Synthesis and Photoinitiating Behavior of Benzophenone-Based Polymeric Photoinitiators Used for UV Curing Coatings[J]. Prog Org Coat, 2011,71:355-361. doi: 10.1016/j.porgcoat.2011.04.004

    28. [28]

      JIN Yangzhi. Properties and Applications Handbook:UV-Curable Materials[M]. Beijing:Chemical Industry Press, 2010(in Chinese).

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