Skip to main content
Log in

Preparation in presence of urushiol and properties of acrylate latex with interparticle bridges

  • Published:
Journal of Coatings Technology and Research Aims and scope Submit manuscript

Abstract

Acrylate latices were prepared by seeded emulsion polymerization of methyl methacrylate (MMA) and butyl acrylate (BA) in presence of urushiol with multifunctional groups (0–6 wt%). The emulsion polymerization was strongly influenced by the urushiol content. With increasing urushiol content, the conversion rate of the monomers first increased then decreased, the stability of emulsion polymerization gradually declined, the average particle size of the latex increased from 115.9 to 175.3 nm, and a change from mono- to bimodal particle size distribution occurred. Interestingly, transmission electron microscopy (TEM) showed that some particles were connected by linear bridges in presence of urushiol. Based on results of 1H nuclear magnetic resonance (NMR) analysis, such formation of interparticle bridges is due to participation of urushiol in the emulsion polymerization of the acrylate monomers. The content of urushiol also affected the properties of latex films. With increasing urushiol content from 0 to 3 wt%, the adhesion, pencil hardness, and contact angle were markedly improved from grade 6 to grade 2, from B to 3H, and from 22° to 61°, respectively, due to formation of interparticle bridges. When the content of urushiol exceeded 3 wt%, the adhesion and pencil hardness remained unchanged, but the water contact angle markedly declined because of higher surface roughness of the latex film. Furthermore, addition of urushiol enhanced the thermal stability of the latex films.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9

Similar content being viewed by others

References

  1. Wang, RM, Wang, JF, Wang, XW, He, YF, Zhu, YF, Jiang, ML, “Preparation of Acrylate-Based Copolymer Emulsion and Its Humidity Controlling Mechanism in Interior Wall Coatings.” Prog. Org. Coat., 71 (4) 369–375 (2011)

    Article  Google Scholar 

  2. Athawale, VD, Kulkarni, MA, “Preparation and Properties of Urethane/Acrylate Composite by Emulsion Polymerization Technique.” Prog. Org. Coat., 65 (3) 392–400 (2009)

    Article  Google Scholar 

  3. Wu, GF, Wang, CY, Tan, ZY, Zhang, HX, “Effect of Temperature on Emulsion Polymerization of n-Butyl Acrylate.” Procedia Eng., 18 353–357 (2011)

    Article  Google Scholar 

  4. Xu, L, Xu, L, Dai, WS, Tsuboi, T, Xie, HD, “Preparation and Characterization of a Novel Fluoro-Silicone Acrylate Copolymer by Semi-continuous Emulsion Polymerization.” J. Fluorine Chem., 153 (5) 68–73 (2013)

    Article  Google Scholar 

  5. Zhai, LF, Lu, DP, Fan, NN, Wang, XL, Guan, R, “Facile Fabrication and Modification of Polyacrylate/Silica Nanocomposite Latexes Prepared by Silica Sol and Silane Coupling Agent.” J. Coat. Technol. Res., 10 (6) 799–810 (2013)

    Article  Google Scholar 

  6. Zhang, YF, Zhang, R, Yang, CL, Xu, J, Zheng, J, Lu, MG, “Stable Acrylate/Triethoxyvinylsilane (VTES) Core-Shell Emulsion with Low Surface Tension Made by Modified Micro-emulsion Polymerization: Effect of Different Mass Ratio of MMA/BA in the Core and Shell.” Colloids Surfaces A, 436 (35) 549–556 (2013)

    Article  Google Scholar 

  7. Çanak, TÇ, Serhatlı, İE, “Synthesis of Fluorinated Urethane Acrylate Based UV-Curable Coatings.” Prog. Org. Coat., 76 (2–3) 388–399 (2013)

    Article  Google Scholar 

  8. Javaheriannaghash, H, Ghazavi, N, “Preparation and Characterization of Water-Based Polyurethane-Acrylic Hybrid Nanocomposite Emulsion Based on a New Silane-Containing Acrylic Macromonomer.” J. Coat. Technol. Res., 9 (3) 323–336 (2012)

    Article  Google Scholar 

  9. Yılmaz, O, Cheaburu, CN, Gülümser, G, Vasile, C, “On the Stability and Properties of the Polyacrylate/Na-MMT Nanocomposite Obtained by Seeded Emulsion Polymerization.” Eur. Polym. J., 48 (10) 1683–1695 (2012)

    Article  Google Scholar 

  10. Thanamongkollit, N, Soucek, MD, “Synthesis and Properties of Acrylate Functionalized Alkyds via a Diels-Alder Reaction.” Prog. Org. Coat., 73 (4) 382–391 (2012)

    Article  Google Scholar 

  11. Dziczkowski, J, Soucek, MD, “A New Class of Acrylated Alkyds.” J. Coat. Technol. Res., 7 (5) 587–602 (2010)

    Article  Google Scholar 

  12. Wu, W, Severtson, S, Miller, C, “Alkali-Soluble Resins (ASR) and Acrylic Blends: Influence of ASR Distribution on Latex Film and Paint Properties.” J. Coat. Technol. Res., 13 (4) 655–665 (2016)

    Article  Google Scholar 

  13. Fertier, L, Koleilat, H, Stemmelen, M, Giani, O, Christine, JD, Lapinte, V, Robin, JJ, “The Use of Renewable Feedstock in UV-Curable Materials-a New Age for Polymers and Green Chemistry.” Prog. Polym. Sci., 38 (6) 932–962 (2013)

    Article  Google Scholar 

  14. Balgude, D, Sabnis, AS, “CNSL: An Environment Friendly Alternative for the Modern Coating Industry.” J. Coat. Technol. Res., 11 (2) 169–183 (2014)

    Article  Google Scholar 

  15. Bai, WB, Lin, JH, “Characterisation of Urushiol Formaldehyde Polymer/Multihydroxyl Polyacrylate/SiO2 Nanocomposites Prepared by the Sol-Gel Method.” Prog. Org. Coat., 71 (1) 43–47 (2011)

    Article  Google Scholar 

  16. Lu, R, Wan, YY, Honda, T, Ishimura, T, Kamiya, Y, Miyakoshi, T, “Design and Characterization of Modified Urethane Lacquer Coating.” Prog. Org. Coat., 57 (3) 215–222 (2006)

    Article  Google Scholar 

  17. Kumanotani, J, “Enzyme Catalyzed Durable and Authentic Oriental Lacquer: A Natural Microgelprintable Coating by Polysaccharide–Glycoprotein–Phenolic Lipid Complexes.” Prog. Org. Coat., 34 (1–4) 135–146 (1998)

    Article  Google Scholar 

  18. Yang, J, Deng, J, Zhang, Q, Shen, Q, Li, D, Xiao, Z, “Effects of Polysaccharides on the Properties of Chinese Lacquer Sap.” Prog. Org. Coat., 78 176–182 (2015)

    Article  Google Scholar 

  19. Kim, D, Jeon, SL, Seo, J, “The Preparation and Characterization of Urushiol Powders (YPUOH) Based on Urushiol.” Prog. Org. Coat., 76 (10) 1465–1470 (2013)

    Article  Google Scholar 

  20. Xia, JR, Lin, JH, Xu, YL, Chen, QH, “On the UV-Induced Polymeric Behavior of Chinese Lacquer.” ACS Appl. Mater. Interfaces, 3 (2) 482–489 (2011)

    Article  Google Scholar 

  21. Yang, J, Deng, J, Zhu, J, Shen, Q, Li, D, “Lacquer Sap with Reactive Maleic Hemiester Surfactant-Modified Phase Interface and Its Properties.” Prog. Org. Coat., 87 138–145 (2015)

    Article  Google Scholar 

  22. Xu, YL, Bai, WB, Luo, Z, Jin, Y, Peng, BC, Feng, LX, Hu, BH, Lin, JH, “Effects of Drying Time on the Surface Morphology Evolution of Urushiol-Formaldehyde Diethylenetriamine Polymer Microporous Films.” Appl. Surf. Sci., 258 (12) 5141–5145 (2012)

    Article  Google Scholar 

  23. Lu, R, Yoshida, T, Miyakoshi, T, “Oriental Lacquer: A Natural Polymer.” Polym. Rev., 53 (2) 153–191 (2013)

    Article  Google Scholar 

  24. Kim, HS, Yeum, JH, Choi, SW, Lee, JY, Cheong, IW, “Urushiol/Polyurethane-Urea Dispersions and Their Film Properties.” Prog. Org. Coat., 65 (3) 341–347 (2009)

    Article  Google Scholar 

  25. Liu, YZ, Xia, JR, Lin, JH, “Characterization and Conductive Property of Polyurushiol/Silver Conductive Coatings Prepared under UV Irradiation.” Prog. Org. Coat., 71 (1) 117–120 (2011)

    Article  Google Scholar 

  26. Xia, JR, Xu, YL, Hu, BH, Lin, JH, “A Rapid Approach to Urushiol-Copper(I) Coordination Polymer under UV Irradiation.” Prog. Org. Coat., 65 (4) 510–513 (2009)

    Article  Google Scholar 

  27. Xu, YL, Xia, JR, Hu, BH, “Controlled Growth of CdS Nanoparticles in Polyurushiol Matrices.” Prog. Org. Coat., 65 (1) 25–29 (2009)

    Article  Google Scholar 

  28. Xu, YL, Tong, ZQ, Xia, JR, Hu, BH, Lin, JH, “Urushiol-Formaldehyde Polymer Microporous Films with Acid–Alkali Resistance Property: Effects of Formation Conditions on Surface Morphologies.” Prog. Org. Coat., 72 (3) 586–591 (2011)

    Article  Google Scholar 

  29. Xia, JR, Xu, YL, Lin, JH, “UV-Induced Polymerization of Urushiol II: Effects of Hydrogenation Degree of Urushiol on Surface Morphology.” Prog. Org. Coat., 67 (3) 365–369 (2010)

    Article  Google Scholar 

  30. Ishimura, T, Lu, R, Yamasaki, K, Miyakoshi, T, “Effects of Hybridization of Lacquer Sap with Organic Silane on Drying Properties.” Prog. Org. Coat., 62 (2) 193–198 (2008)

    Article  Google Scholar 

  31. Yang, J, Zhu, Y, Zhu, J, Liu, W, Zhou, M, Zhi, L, Li, D, Shen, Q, “Influences of Maleic Reactive Surfactants with Different EO Chain Lengths on the Properties of the Acrylate Latices.” J. Coat. Technol. Res., 12 (6) 1041–1052 (2015)

    Article  Google Scholar 

  32. Xiao, X, Wang, Y, “Emulsion Copolymerization of Fluorinated Acrylate in the Presence of a Polymerizable Emulsifier.” Colloids Surfaces A, 348 (1–3) 151–156 (2009)

    Article  Google Scholar 

  33. Takei, R, Lu, R, Miyakoshi, T, “Dimer Structures and Laccase-Catalyzed Polymerization Mechanism of Laccol in Fresh Rhus Succedanea Lacquer Sap.” Int. J. Polym. Anal. Charact., 18 (3) 199–210 (2013)

    Article  Google Scholar 

  34. Lu, R, Miyakoshi, T, Lacquer Chemistry and Application. Elsevier, Amsterdam 2015

    Google Scholar 

  35. Huang, Z, Qiu, F, You, J, Qian, B, “2D NMR Studies on the Structure of Urushiol of Chinese Lacquer.” Chem. J. Chin. Univ., 3 (1) 75–80 (1987)

    Google Scholar 

  36. Harigaya, S, Honda, T, Lu, R, Miyakoshi, T, Chen, CL, “Enzymatic Dehydrogenative Polymerization of Urushiol in Fresh Exudates from the Lacquer Tree. Rhus Vernicifera DC.” J. Agric. Food Chem., 55 (6) 2201–2208 (2007)

    Article  Google Scholar 

  37. Xu, W, An, Q, Hao, L, Zhang, D, Zhang, M, “Synthesis and Characterization of Self-Crosslinking Fluorinated Polyacrylate Soap-Free Latices with Core-Shell Structure.” Appl. Surf. Sci., 268 (3) 373–380 (2013)

    Article  Google Scholar 

  38. Yang, T, Peng, H, Cheng, S, Park, IJ, “Soap-Free Emulsion Copolymerization of Perfluoroalkyl Acrylates in the Presence of a Reactive Surfactant.” J. Appl. Polym. Sci., 104 (4) 2438–2444 (2007)

    Article  Google Scholar 

  39. Dai, M, Zhang, Y, He, P, “Preparation and Characterization of Stable and High Solid Content St/BA Emulsifier-Free Latexes in the Presence of AMPS.” Polym. Bull., 67 (1) 91–100 (2011)

    Article  Google Scholar 

  40. Yang, SF, Xiong, PT, Gong, T, Lu, DP, Guan, R, “St–BA Copolymer Emulsions Prepared by Using Novel Cationic Maleic Dialkyl Polymerizable Emulsifier.” Eur. Polym. J., 41 (12) 2973–2979 (2005)

    Article  Google Scholar 

  41. Harkins, WD, “A General Theory of the Mechanism of Emulsion Polymerization.” J. Am. Chem. Soc., 69 (6) 1428–1444 (1947)

    Article  Google Scholar 

  42. Davies, JT, “A Quantitative Kinetic Theory of Emulsion Type. I. Physical Chemistry of the Emulsifying Agent.” Proc Int Congr Surface Activity (2nd), Vol. I, Butterworth, London, 1957, pp 426–438

  43. Chang, W, Liu, L, Zhang, J, Pan, Q, Pei, M, “Preparation and Characterization of Styrene/Butyl Acrylate Emulsifier-Free Latex with 2-Acrylamido-2-Methyl Propane Sulfonic Acid as a Reactive Emulsifier.” J. Disper. Sci. Technol., 30 (5) 639–642 (2009)

    Article  Google Scholar 

  44. Dobie, CG, Boodhoo, KVK, “Surfactant-Free Emulsion Polymerisation of Methyl Methacrylate and Methyl Acrylate Using Intensified Processing Methods.” Chem. Eng. Process., 49 (9) 901–911 (2010)

    Article  Google Scholar 

  45. Park, DH, Oh, JK, Kim, SB, Kim, WN, “Synthesis and Characterization of Sulfonated Polyol-Based Waterborne Polyurethane-Polyacrylate Hybrid Emulsions.” Macromol. Res., 21 (11) 1247–1253 (2013)

    Article  Google Scholar 

  46. Xu, HL, Lu, ZJ, Zhang, GZ, “Synthesis and Properties of Thermosetting Resin Based on Urushiol.” RSC Adv., 2 (7) 2768–2772 (2012)

    Article  Google Scholar 

  47. Oliver, JF, Huh, C, Mason, SG, “Effects of Solid Surface Roughness on Wetting.” Colloids Surf., 1 79–104 (1980)

    Article  Google Scholar 

  48. Yang, J, Deng, J, Zhu, J, Liu, W, Zhou, M, Li, D, “Thermal Polymerization of Lacquer Sap and Its Effects on the Properties of Lacquer Film.” Prog. Org. Coat., 94 41–48 (2016)

    Article  Google Scholar 

  49. Boruah, M, Gogoi, P, Adhikari, B, Dolui, SK, “Preparation and Characterization of Jatropha Curcas Oil Based Alkyd Resin Suitable for Surface Coating.” Prog. Org. Coat., 74 (3) 596–602 (2012)

    Article  Google Scholar 

Download references

Acknowledgments

This work was supported by the National Natural Science Foundation of China (No. 31270616), Key Laboratory of Fermentation Engineering (Ministry of Education) Open Foundation, and Jiangsu Rongchang New Material Technology Co., Ltd.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Jianhong Yang.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yang, J., Shen, Q., Shen, F. et al. Preparation in presence of urushiol and properties of acrylate latex with interparticle bridges. J Coat Technol Res 15, 819–830 (2018). https://doi.org/10.1007/s11998-017-0023-6

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11998-017-0023-6

Keywords

Navigation