Top

Journal of Polymer Research

Published in:

01-07-2013 | Original Paper

UV cured polymer based on a renewable cardanol derived RAFT agent

Authors: Chuanjie Cheng, Xiongxiong Bai, Shaojin Liu, Qinghua Huang, Yuanming Tu, Haiming Wu, Xiaoji Wang

Published in: Journal of Polymer Research | Issue 7/2013

Activate our intelligent search to find suitable subject content or patents.

search-config

AI-assisted search

Off

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.

previous article Green PU resin from an accelerated Non-isocyanate process with microwave radiation

next article Effect of the contribution of crystalline and amorphous phase on tensile behavior of poly (phenylene sulfide)

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

über 102.000 Bücher
über 537 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Finance + Banking
Management + Führung
Marketing + Vertrieb
Maschinenbau + Werkstoffe
Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

inform now

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

über 67.000 Bücher
über 390 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Maschinenbau + Werkstoffe

Jetzt Wissensvorsprung sichern!

inform now

Available only for authorised users

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

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 20:48–55CrossRef

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 19:1–10CrossRef

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

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

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

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

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)

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

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 17:12646–12658CrossRef

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 9:1352–1355CrossRef

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 296:526–530CrossRef

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 45:1089–1099CrossRef

14.

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

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 52:142–188CrossRef

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 67:1185–1200CrossRef

17.

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

18.

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

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 3:2685–2697CrossRef

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 66:735–746CrossRef

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 18:559–568CrossRef

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 19:9895CrossRef

23.

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

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 69:1041–1051CrossRef

25.

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

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 18:615–620CrossRef

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 18:1229–1235CrossRef

28.

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

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

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 67:336–341CrossRef

31.

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

32.

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

33.

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

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 44:7584–7593CrossRef

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 43:6302–6310CrossRef

36.

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

37.

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

38.

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

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 44:5619–5630CrossRef

40.

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

41.

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

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 51:1572–1577CrossRef

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 109:2781–2790CrossRef

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 19:9995–10006CrossRef

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 19:1048–1055CrossRef

46.

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

47.

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

48.

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

49.

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

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 45:5354–5364CrossRef

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 68:2313–2322CrossRef

52.

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

53.

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

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)

Title: UV cured polymer based on a renewable cardanol derived RAFT agent
Authors: Chuanjie Cheng
Xiongxiong Bai
Shaojin Liu
Qinghua Huang
Yuanming Tu
Haiming Wu
Xiaoji Wang
Publication date: 01-07-2013
Publisher: Springer Netherlands
Published in: Journal of Polymer Research / Issue 7/2013
Print ISSN: 1022-9760
Electronic ISSN: 1572-8935
DOI: https://doi.org/10.1007/s10965-013-0197-2

Springer Professional

Abstract

Please log in to get access to your license.

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Springer Professional "Technik"

Other articles of this Issue 7/2013

Study on preparation and associative properties of fluorinated hydrophobically associating polyacrylamide

Novel hydrogels containing nanosilver for biomedical applications - synthesis and characterization

Preparation and self-assembly properties of silicone-modified hydrophobically associating polyacrylamide

Development of novel chitosan-poly(N,N-diethylacrylamide) IPN films for potential wound dressing and biomedical applications

Novel organosoluble aromatic polyetheramides bearing triphenylamine moieties: synthesis, electrochemistry, and electrochromism

Effect of polymerizable emulsifier and fluorine monomer on properties of self-crosslinking fluorinated polyacrylate soap-free latexes

Premium Partners