Skip to main content

Advertisement

Log in

UV cured polymer based on a renewable cardanol derived RAFT agent

  • Original Paper
  • Published:
Journal of Polymer Research Aims and scope Submit manuscript

Abstract

A cardanol-derived reversible addition-fragmentation chain transfer (RAFT) agent was synthesized in 57 % total yield, and a cardanol-based anionic surfactant was also facilely prepared. Emulsion polymerization of methyl methacrylate (MMA) was realized to form a cardanol-terminated PMMA polymer by using the novel RAFT agent as well as the cardanol-based anionic surfactant. To improve the properties of cardanol-terminated PMMA as a material, UV-curing was performed. According to the comprehensive behavior of the UV-cured resins, optimal irradiation time was 20 min.

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
Scheme 2
Fig. 1
Scheme 3
Fig. 2

Similar content being viewed by others

References

  1. Vennestrøm PNR, Osmundsen CM, Christensen CH, Taarning E (2011) Beyond petrochemicals: the renewable chemicals industry. Angew Chem Int Ed 50:2–10

    Article  Google Scholar 

  2. Kubota T, Araújo MVG, Vieira JVF, Silva TA, Ramos LP, Zawadzki SF (2013) Synthesis of new carbohydrate-based polyurethanes and their application in the purification of methyl esters (biodiesel). J Polym Res 20:48–55

    Article  Google Scholar 

  3. Rodrigues FHA, Fajardo AR, Pereira AGB, Ricardo NMPS, Feitosa JPA, Muniz EC (2012) Chitosan-graft-poly(acrylic acid)/rice husk ash based superabsorbent hydrogel composite: preparation and characterization. J Polym Res 19:1–10

    Article  Google Scholar 

  4. Xin YR, Uyama H (2012) Synthesis of new bio-based polycarbonates derived from terpene. J Polym Res 19:15–21

    Article  Google Scholar 

  5. Ikeda R, Tanaka H, Uyama H, Kobayashi S (2000) A new crosslinkable polyphenol from a renewable resource. Macromol Rapid Commun 21:496–499

    Article  CAS  Google Scholar 

  6. Mele G, Vasapollo G (2008) Fine chemicals and new hybrid materials from cardanol. Mini Rev Org Chem 5:243–253

    Article  CAS  Google Scholar 

  7. Cardona F, Kin-Tak AL, Fedrigo J (2012) Novel phenolic resins with improved mechanical and toughness properties. J Appl Polym Sci 123:2131–2139

    Article  CAS  Google Scholar 

  8. Cheng CJ, Zha JW, Liu ZB, Shen L, Sun J, Liu YJ (2012) Synthesis and UV curing properties of a photo-active cardanol derivative. Chin J Appl Chem 29:392–396 (in Chinese)

    CAS  Google Scholar 

  9. Tanaka S, Honzawa H, Iji M (2013) Development of cardanol-bonded cellulose thermoplastics: high productivity achieved by using isocyanate-modified cardanol. J Appl Polym Sci. doi:10.1002/app.39313

    Google Scholar 

  10. Bhavsar GA, Asha SK (2011) Pentadecyl phenol- and cardanol-functionalized fluorescent, room-temperature liquid-crystalline perylene bisimides: effect of pendant chain unsaturation on self-assembly. Chem Eur J 17:12646–12658

    Article  CAS  Google Scholar 

  11. Amorati R, Attanasi OA, Favi G, Menichetti S, Pedullia GF, Viglianisi C (2011) Amphiphilic antioxidants from “cashew nut shell liquid” (CNSL) waste. Org Biomol Chem 9:1352–1355

    Article  CAS  Google Scholar 

  12. Campaner P, D’Amico D, Ferri P, Longo L, Maffezzoli A, Stifani C, Tarzia A (2010) Cardanol based matrix for jute reinforced pipes. Macromol Symp 296:526–530

    Article  CAS  Google Scholar 

  13. Chu DSH, Schellinger JG, Shi J, Convertine AJ, Stayton PS, Pun A (2012) Application of living free radical polymerization for nucleic acid delivery. Acc Chem Res 45:1089–1099

    Article  CAS  Google Scholar 

  14. Tasdelen MA, Kahveci MU, Yagci Y (2011) Telechelic polymers by living and controlled/living polymerization methods. Prog Polym Sci 36:455–567

    Article  CAS  Google Scholar 

  15. Roghani-Mamaqani H, Haddadi-Asl V, Salami-Kalajahi M (2012) In situ controlled radical polymerization: a review on synthesis of well-defined nanocomposites. Polym Rev 52:142–188

    Article  CAS  Google Scholar 

  16. Shu JB, Cheng CJ, Zheng Y, Shen L, Qiao YL, Fu CQ (2011) “One pot” synthesis of fluorinated block copolymers using a surface-active ATRP initiator under emulsion polymerization conditions. Polym Bull 67:1185–1200

    Article  CAS  Google Scholar 

  17. Matyjaszewski K (2012) Atom transfer radical polymerization (ATRP): current status and future perspectives. Macromolecules 45:4015–4039

    Article  CAS  Google Scholar 

  18. Semsarilar M, Perrier S (2010) ‘Green’ reversible addition-fragmentation chain-transfer (RAFT) polymerization. Nat Chem 2:811–820

    Article  CAS  Google Scholar 

  19. Bai LJ, Zhang LF, Cheng ZP, Zhu XL (2012) Activators generated by electron transfer for atom transfer radical polymerization: recent advances in catalyst and polymer chemistry. Polym Chem 3:2685–2697

    Article  CAS  Google Scholar 

  20. Cheng CJ, Gong SS, Fu QL, Shen L, Liu ZB, Qiao YL, Fu CQ (2011) Hexamethylenetetramine as both a ligand and a reducing agent in AGET atom transfer radical batch emulsion polymerization. Polym Bull 66:735–746

    Article  CAS  Google Scholar 

  21. Percino MJ, Chapela VM, Camacho A, Soriano-Moro G, Cerón M (2011) Atom transfer radical polymerization of monomers containing amide and ester moieties monitored by dilatometric method. J Polym Res 18:559–568

    Article  CAS  Google Scholar 

  22. Wang CX, Xu J, Gao Y, Yang DG, Li HM (2012) RAFT synthesis of acrylic polymers containing diol or dioxane groups. J Polym Res 19:9895

    Article  Google Scholar 

  23. Li CJ, Chen L (2006) Organic chemistry in water. Chem Soc Rev 35:68–82

    Article  Google Scholar 

  24. Hu J, Zheng SH, Mao XM, Xu XL (2012) Soap-free emulsion polymerization of n-butyl acrylate in aqueous solution in the presence of α- and methylated β-cyclodextrin. Polym Bull 69:1041–1051

    Article  CAS  Google Scholar 

  25. Yin DZ, Zhang QY, Zhang HP, Yin CJ (2010) Fabrication of covalently-bonded polystyrene/SiO2 composites by Pickering emulsion polymerization. J Polym Res 17:689–696

    Article  CAS  Google Scholar 

  26. Zhang FA, Kang JS, Yu CL (2011) Effect of acrylic acid and hydroxyethyl methacrylate modified nano-SiO2 particles on poly(methyl methacrylatehydroxyethyl methacrylate) soap-free emulsion polymerization. J Polym Res 18:615–620

    Article  Google Scholar 

  27. Wang WW, Zhang QY, Guo FG, Gu JW, Yin CJ (2011) Preparation of diblock copolymer PBA-b-PSt by DPE method in emulsion. J Polym Res 18:1229–1235

    Article  CAS  Google Scholar 

  28. Cheng CJ, Shen L, Fu QL, Gong SS (2011) Soap-free living/controlled radical polymerization. Prog Chem 23:791–799 (in Chinese)

    CAS  Google Scholar 

  29. Cheng CJ, Bai XX, Fan WQ, Wu HM, Shen L, Huang QH, Tu YM (2013) Synthesis of a photoactive gemini surfactant and its use in AGET ATRP miniemulsion polymerisation and UV curing. Chem Pap. doi:10.2478/s11696-013-0420-y

    Google Scholar 

  30. Cheng CJ, Fu QL, Bai XX, Liu SJ, Shen L, Fan WQ, Li HX (2013) Facile synthesis of gemini surface-active ATRP initiator and its use in soap-free AGET ATRP mini-emulsion polymerisation. Chem Pap 67:336–341

    Article  CAS  Google Scholar 

  31. Oh JK (2008) Recent advances in controlled/living radical polymerization in emulsion and dispersion. J Polym Sci A Polym Chem 46:6983–7001

    Article  CAS  Google Scholar 

  32. Li WW, Yoon JA, Matyjaszewski K (2010) Dual-reactive surfactant used for synthesis of functional nanocapsules in miniemulsion. J Am Chem Soc 132:7823–7825

    Article  CAS  Google Scholar 

  33. Li WW, Matyjaszewski K (2011) Cationic surface-active monomers as reactive surfactants for AGET emulsion ATRP of n-butyl methacrylate. Macromolecules 44:5578–5585

    Article  CAS  Google Scholar 

  34. Zhang WJ, D’Agosto F, Boyron O, Rieger J, Charleux B (2011) One-pot synthesis of poly(methacrylic acid-co-poly(ethylene oxide) methyl ether methacrylate)-b-polystyrene amphiphilic block copolymers and their self-assemblies in water via RAFT-mediated radical emulsion polymerization. A kinetic study. Macromolecules 44:7584–7593

    Article  CAS  Google Scholar 

  35. Rieger J, Zhang WJ, Stoffelbach F, Charleux B (2010) Surfactant-free RAFT emulsion polymerization using poly(N, N-dimethylacrylamide) trithiocarbonate macromolecular chain transfer agents. Macromolecules 43:6302–6310

    Article  CAS  Google Scholar 

  36. An ZS, Qiu Q, Liu GY (2011) Synthesis of architecturally well-defined nanogels via RAFT polymerization for potential bioapplications. Chem Commun 47:12424–12440

    Article  CAS  Google Scholar 

  37. Mori H, Endo T (2012) Amino-acid-based block copolymers by RAFT polymerization. Macromol Rapid Commun 33:1090–1107

    Article  CAS  Google Scholar 

  38. Chen Z, Wang XL, Su JS, Zhuo D, Ran R (2010) Branched methyl methacrylate copolymer particles prepared by RAFT dispersion polymerization. Polym Bull 64:327–339

    Article  CAS  Google Scholar 

  39. Stamenović MM, Espeel P, Camp WV, Du Prez FE (2011) Norbornenyl-based RAFT agents for the preparation of functional polymers via thiol-ene chemistry. Macromolecules 44:5619–5630

    Article  Google Scholar 

  40. Deng JP, Wang LF, Liu LY, Yang WT (2009) Developments and new applications of UV-induced surface graft polymerizations. Prog Polym Sci 34:156–193

    Article  CAS  Google Scholar 

  41. Cakmakc E, Mülazim Y, Kahraman MV, Apohan NK (2012) Preparation and characterization of boron containing thiol-ene photocured hybrid coatings. Prog Org Coat 75:28–32

    Article  Google Scholar 

  42. Yang ZL, Wicks DA, Yuan JJ, Pu HT, Liu YS (2010) Newly UV-curable polyurethane coatings prepared by multifunctional thiol- and ene-terminated polyurethane aqueous dispersions: photopolymerization properties. Polymer 51:1572–1577

    Article  CAS  Google Scholar 

  43. Rekha N, Asha SK (2008) Synthesis and FTIR spectroscopic investigation of the UV curing kinetics of telechelic urethane methacrylate crosslinkers based on the renewable resource-cardanol. J Appl Polym Sci 109:2781–2790

    Article  CAS  Google Scholar 

  44. Kaewpirom S, Kunwong D (2012) Curing behavior and cured film performance of easy-to-clean UV-curable coatings based on hybrid urethane acrylate oligomers. J Polym Res 19:9995–10006

    Article  Google Scholar 

  45. Cheng CJ, Fu QL, Liu ZB, Shen L, Qiao YL, Fu CQ (2011) Emulsifier-free synthesis of crosslinkable ABA triblock copolymer nanoparticles via AGET ATRP. Macromol Res 19:1048–1055

    Article  CAS  Google Scholar 

  46. Rwei SP, Chen JD (2012) Investigating the UV-curing performance for polyacrylated polymer in dendritic and regular conformation. Polym Bull 68:493–505

    Article  CAS  Google Scholar 

  47. Zhang GB, Fan XD, Kong J, Liu YY (2008) Kinetic study on UV-curing of hyperbranched polysiloxane. Polym Bull 60:863–874

    Article  CAS  Google Scholar 

  48. Xiao P, Zhang HQ, Dai MZ, Nie J (2009) Synthesis and characterization of 4,4′-diacryloyloxybenzophenone. Prog Org Coat 64:510–514

    Article  CAS  Google Scholar 

  49. Skey J, Reilly RKO (2008) Facile one pot synthesis of a range of reversible addition-fragmentation chain transfer (RAFT) agents. Chem Commun 35:4183–4185

    Article  Google Scholar 

  50. Zhu JL, Zhang XZ, Cheng H, Li YY, Cheng SX, Zhuo RX (2007) Synthesis and characterization of well-defined, amphiphilic poly(N-isopropylacrylamide)-b-[2-hydroxyethyl methacrylate- poly(e-caprolactone)] graft copolymers by RAFT polymerization and macromonomer method. J Polym Sci A Polym Chem 45:5354–5364

    Article  CAS  Google Scholar 

  51. Ovando-Medina VM, Piña-García PS, Corona-Rivera MA, Díaz-Flores PE, Peralta RD, Martínez-Gutiérrez H, Lara-Ceniceros TE (2012) Semicontinuous heterophase polymerization of methyl methacrylate in the presence of reactive surfactant HITENOL BC10. Polym Bull 68:2313–2322

    Article  CAS  Google Scholar 

  52. Tomanová V, Pielichowski K, Sroková I, Žoldaková A, Sasinková V, Ebringerová A (2008) Microwave-assisted synthesis of carboxymethylcellulose-based polymeric surfactants. Polym Bull 60:15–25

    Article  Google Scholar 

  53. Peungjitton P, Sangvanich P, Pornpakakul S, Petsom A, Roengsumran S (2009) Sodium cardanol sulfonate surfactant from cashew nut shell liquid. J Surfactant Deterg 12:85–89

    Article  CAS  Google Scholar 

  54. Zhou JH, Cui YD (2001) Measurement and calculation of HLB value of surfactants I. The measurement of HLB value. Speciality Petrochem (2):11–14 (in Chinese)

Download references

Acknowledgments

The work was financially supported by Natural Science Foundations of China (NO. 21264008, 21062006) and the Natural Science Foundations of Jiangxi Province (No. 2009GZH0035).

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Chuanjie Cheng or Xiaoji Wang.

Electronic supplementary material

Below is the link to the electronic supplementary material.

ESM 1

(DOC 2935 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Cheng, C., Bai, X., Liu, S. et al. UV cured polymer based on a renewable cardanol derived RAFT agent. J Polym Res 20, 197 (2013). https://doi.org/10.1007/s10965-013-0197-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s10965-013-0197-2

Keywords

Navigation