New polymer systems based on polyethylene glycol: synthesis, characterization, and study of the solubility behavior

  • Azar Ghaffari
  • Malihe Pooresmaeil
  • Hassan NamaziEmail author
  • Ali A. Entezami
Original Paper


Recently due to the exclusive rheological properties and a highly branched structure, star-shaped polymers have received more attention. In the first section of the present work, the polyethylene glycol (PEG)-based star-shaped polymer systems were prepared from the reaction of methoxypolyethylene glycols with various molecular weight as arm and trimesoyl chloride (TMC) as a core. The structure of the synthesized star-shaped polymers confirmed using the Fourier transform infrared spectroscopy and proton nuclear magnetic resonance. The solubility test showed that the synthesized polymers are soluble in water, dimethyl sulfoxide, dimethylformamide, and chlorinated solvents. In the second part of this work, the crosslinked PEGs preparation possibility in the melt state by using the trimesic acid (TMA) and TMC as a crosslinker was investigated. Evaluation of the swelling and solubility behavior of the prepared systems showed that the prepared crosslinked systems with TMA are soluble in most of the organic solvents, while the crosslinked systems with TMC as a crosslinker are insoluble in all of the organic solvents and show the swellability characteristics. From the obtained results it is concluded that the TMC is a better crosslinker for the crosslinking of PEG in the melt state.

Graphical abstract


Polyethylene glycol Star-shaped polymer Crosslinked polymers Trimesoyl chloride Trimesic acid 



Authors gratefully acknowledge the University of Tabriz (Grant #77634252) and Research Center for Pharmaceutical Nanotechnology (RCPN), Tabriz University of Medical Science, for the financial supports for this research.

Compliance with ethical standards

Conflict of interest

The authors declare that there is no conflict of interest.


  1. 1.
    Mahida VP, Patel MP (2016) Removal of some most hazardous cationic dyes using novel poly (NIPAAm/AA/N-allylisatin) nanohydrogel. Arab J Chem 9(3):430–442. CrossRefGoogle Scholar
  2. 2.
    Tan JH, McMillan NAJ, Payne E, Alexander C, Heath F, Whittaker AK, Thurecht KJ (2012) Hyperbranched polymers as delivery vectors for oligonucleotides. J Polym Sci Part A Polym Chem 50(13):2585–2595. CrossRefGoogle Scholar
  3. 3.
    Knop K, Pretzel D, Urbanek A, Rudolph T, Scharf DH, Schallon A, Wagner M, Schubert S, Kiehntopf M, Brakhage AA, Schacher FH, Schubert US (2013) Star-shaped drug carriers for doxorubicin with POEGMA and POEtOxMA brush-like shells: a structural, physical, and biological comparison. Biomacromolecules 14(8):2536–2548. CrossRefPubMedGoogle Scholar
  4. 4.
    Namazi H, Jafarirad S (2011) Application of hybrid organic/inorganic dendritic ABA type triblock copolymers as new nanocarriers in drug delivery systems. Int J Polym Mater Polym Biomater 60(9):603–619. CrossRefGoogle Scholar
  5. 5.
    Namazi H, Kanani A (2009) Investigation diffusion mechanism of β-lactam conjugated telechelic polymers of PEG and β-cyclodextrin as the new nanosized drug carrier devices. Carbohydr Polym 76(1):46–50. CrossRefGoogle Scholar
  6. 6.
    Namazi H, Fathi F, Heydari A (2012) Nanoparticles based on modified polysaccharides. In: Hashim AA (ed) The delivery of nanoparticles. InTech, LondonGoogle Scholar
  7. 7.
    Rajulu AV, Sab PM (1995) Acoustical parameters of polyethylene glycol/water mixtures. Bull Mater Sci 18(3):247–253CrossRefGoogle Scholar
  8. 8.
    Rehmani S, Ahmad M, Minhas MU, Anwar H, Zangi MI-u-d, Sohail M (2017) Development of natural and synthetic polymer-based semi-interpenetrating polymer network for controlled drug delivery: optimization and in vitro evaluation studies. Polym Bull 74(3):737–761. CrossRefGoogle Scholar
  9. 9.
    Ahmadian Y, Bakravi A, Hashemi H, Namazi H (2019) Synthesis of polyvinyl alcohol/CuO nanocomposite hydrogel and its application as drug delivery agent. Polym Bull 76(4):1967–1983. CrossRefGoogle Scholar
  10. 10.
    Namazi H (2017) Polymers in our daily life. Bioimpacts 7(2):73–74. CrossRefPubMedPubMedCentralGoogle Scholar
  11. 11.
    Pooresmaeil M, Namazi H (2019) Preparation and characterization of polyvinyl alcohol/β-cyclodextrin/GO-Ag nanocomposite with improved antibacterial and strength properties. Polym Adv Technol 30(2):447–456. CrossRefGoogle Scholar
  12. 12.
    Stringer JL, Peppas NA (1996) Diffusion of small molecular weight drugs in radiation-crosslinked poly(ethylene oxide) hydrogels. J Control Release 42(2):195–202. CrossRefGoogle Scholar
  13. 13.
    Merrill EW, Dennison KA, Sung C (1993) Partitioning and diffusion of solutes in hydrogels of poly(ethylene oxide). Biomaterials 14(15):1117–1126. CrossRefPubMedGoogle Scholar
  14. 14.
    Adeli M, Namazi H, Du F, Hönzke S, Hedtrich S, Keilitz J, Haag R (2015) Synthesis of multiarm star copolymers based on polyglycerol cores with polylactide arms and their application as nanocarriers. RSC Adv 5(20):14958–14966. CrossRefGoogle Scholar
  15. 15.
    Javanbakht S, Pooresmaeil M, Hashemi H, Namazi H (2018) Carboxymethylcellulose capsulated Cu-based metal-organic framework-drug nanohybrid as a pH-sensitive nanocomposite for ibuprofen oral delivery. Int J Biol Macromol 119:588–596. CrossRefPubMedGoogle Scholar
  16. 16.
    Lapienis G (2009) Star-shaped polymers having PEO arms. Prog Polym Sci 34(9):852–892. CrossRefGoogle Scholar
  17. 17.
    Fetters LJ, Kiss AD, Pearson DS, Quack GF, Vitus FJ (1993) Rheological behavior of star-shaped polymers. Macromolecules 26(4):647–654. CrossRefGoogle Scholar
  18. 18.
    Ravi Shankar SA, Deo M, Kulkarni R, Gundiah S (1988) Selective flocculation of iron oxide–kaolin mixtures using a modified polyacrylamide flocculant. Bull Mater Sci 10(5):423–433CrossRefGoogle Scholar
  19. 19.
    Namazi H, Mohammad Pour Fard A, Pooresmaeil M (2019) Peripherally functionalized based dendrimers as the template for synthesis of silver nanoparticles and investigation the affecting factors on their properties. Polym Bull 76(9):4659–4675. CrossRefGoogle Scholar
  20. 20.
    Pooresmaeil M, Namazi H (2018) Surface modification of graphene oxide with stimuli-responsive polymer brush containing β-cyclodextrin as a pendant group: preparation, characterization, and evaluation as controlled drug delivery agent. Colloids Surf B 172:17–25. CrossRefGoogle Scholar
  21. 21.
    Kazempour M, Namazi H, Akbarzadeh A, Kabiri R (2019) Synthesis and characterization of PEG-functionalized graphene oxide as an effective pH-sensitive drug carrier. Artif Cells Nanomed Biotechnol 47(1):90–94CrossRefGoogle Scholar
  22. 22.
    Gogoi P, Borah R (2018) Investigation of PEG-6000 bridged –N–SO3H functionalized geminal dicationic ionic liquids for catalytic conversion of fructose to 5-hydroxymethylfurfural. J Chem Sci 130(12):170. CrossRefGoogle Scholar
  23. 23.
    Karmakar G, Nahak P, Guha P, Roy B, Nath RK, Panda AK (2018) Role of PEG 2000 in the surface modification and physicochemical characteristics of pyrazinamide loaded nanostructured lipid carriers. J Chem Sci 130(4):42. CrossRefGoogle Scholar
  24. 24.
    Ye W, Jiang H, Yang X-C (2011) Diethylamine functionalized polyethylene glycol as a novel and efficient catalyst for Knoevenagel condensation. J Chem Sci 123(3):331–334. CrossRefGoogle Scholar
  25. 25.
    Ozcelik B, Palmer J, Ladewig K, Facal Marina P, Stevens GW, Abberton K, Morrison WA, Blencowe A, Qiao GG (2018) Biocompatible porous polyester-ether hydrogel scaffolds with cross-linker mediated biodegradation and mechanical properties for tissue augmentation. Polymers 10(2):179CrossRefGoogle Scholar
  26. 26.
    Savaş H, Güven O (2001) Investigation of active substance release from poly (ethylene oxide) hydrogels. Int J Pharm 224(1–2):151–158CrossRefGoogle Scholar
  27. 27.
    Bunker A (2012) Poly(ethylene glycol) in drug delivery, why does it work, and can we do better? All atom molecular dynamics simulation provides some answers. Phys Procedia 34:24–33. CrossRefGoogle Scholar
  28. 28.
    Knop K, Hoogenboom R, Fischer D, Schubert US (2010) Poly (ethylene glycol) in drug delivery: pros and cons as well as potential alternatives. Angew Chem Int Ed 49(36):6288–6308CrossRefGoogle Scholar
  29. 29.
    Namazi H, Hashemipour SS, Toomari Y (2017) Synthesis of citric-acid-based dendrimers decorated with ferrocenyl groups and investigation of their electroactivity. Polym Bull 74(9):3783–3796. CrossRefGoogle Scholar
  30. 30.
    Philippova OE, Topchieva IN, Kuchanov SI (1986) On the possibility of chemical modification of polyethylene glycol in melt. Polym Bull 15(4):297–302. CrossRefGoogle Scholar
  31. 31.
    Meng F, Engbers GH, Feijen J (2005) Biodegradable polymersomes as a basis for artificial cells: encapsulation, release and targeting. J Control Release 101(1–3):187–198CrossRefGoogle Scholar
  32. 32.
    Furness E, Ross A, Davis T, King G (1998) A hydrophobic interaction site for lysozyme binding to polyethylene glycol and model contact lens polymers. Biomaterials 19(15):1361–1369CrossRefGoogle Scholar
  33. 33.
    Zhang X, Yang D, Nie J (2008) Chitosan/polyethylene glycol diacrylate films as potential wound dressing material. Int J Biol Macromol 43(5):456–462CrossRefGoogle Scholar
  34. 34.
    Namazi H, Bahrami S, Entezami AA (2005) Synthesis and controlled release of biocompatible prodrugs of beta-cyclodextrin linked with PEG containing ibuprofen or indomethacin. Iran Polym J 14(10):921Google Scholar
  35. 35.
    Fruijtier-Pölloth C (2005) Safety assessment on polyethylene glycols (PEGs) and their derivatives as used in cosmetic products. Toxicology 214(1–2):1–38CrossRefGoogle Scholar
  36. 36.
    Klingshirn MA, Spear SK, Holbrey JD, Huddleston JG, Rogers RD (2005) Synthesis, characterization, and application of cross-linked poly(ethylene glycol) networks used for the gelation of ionic liquids. In: Brazel CS, Rogers RD (eds) Ionic liquids in polymer systems, vol 913. ACS symposium series. American Chemical Society, Washington, DC, pp 149–162. CrossRefGoogle Scholar
  37. 37.
    Farhoudian S, Yadollahi M, Namazi H (2016) Facile synthesis of antibacterial chitosan/CuO bio-nanocomposite hydrogel beads. Int J Biol Macromol 82:837–843. CrossRefPubMedGoogle Scholar
  38. 38.
    Bakravi A, Ahamadian Y, Hashemi H, Namazi H (2018) Synthesis of gelatin-based biodegradable hydrogel nanocomposite and their application as drug delivery agent. Adv Polym Technol 37(7):2625–2635. CrossRefGoogle Scholar
  39. 39.
    Javanbakht S, Nazari N, Rakhshaei R, Namazi H (2018) Cu-crosslinked carboxymethylcellulose/naproxen/graphene quantum dot nanocomposite hydrogel beads for naproxen oral delivery. Carbohydr Polym 195:453–459. CrossRefPubMedGoogle Scholar
  40. 40.
    Dadashzadeh A, Imani R, Moghassemi S, Omidfar K, Abolfathi N (2019) Study of hybrid alginate/gelatin hydrogel-incorporated niosomal Aloe vera capable of sustained release of Aloe vera as potential skin wound dressing. Polym Bull. CrossRefGoogle Scholar
  41. 41.
    Pattammattel A, Stromer BS, Baveghems C, Benson K, Kumar CV (2018) Stimuli-responsive, protein hydrogels for potential applications in enzymology and drug delivery§. J Chem Sci 130(10):145. CrossRefGoogle Scholar
  42. 42.
    Molina I, Li S, Martinez MB, Vert M (2001) Protein release from physically crosslinked hydrogels of the PLA/PEO/PLA triblock copolymer-type. Biomaterials 22(4):363–369. CrossRefPubMedGoogle Scholar
  43. 43.
    Hyder MN, Huang RYM, Chen P (2009) Composite poly(vinyl alcohol)–poly(sulfone) membranes crosslinked by trimesoyl chloride: characterization and dehydration of ethylene glycol–water mixtures. J Membr Sci 326(2):363–371. CrossRefGoogle Scholar
  44. 44.
    Yadollahi M, Namazi H, Aghazadeh M (2015) Antibacterial carboxymethyl cellulose/Ag nanocomposite hydrogels cross-linked with layered double hydroxides. Int J Biol Macromol 79:269–277. CrossRefPubMedGoogle Scholar
  45. 45.
    Rakhshaei R, Namazi H (2017) A potential bioactive wound dressing based on carboxymethyl cellulose/ZnO impregnated MCM-41 nanocomposite hydrogel. Mater Sci Eng C 73:456–464. CrossRefGoogle Scholar
  46. 46.
    Namazi H, Adeli M (2003) Novel linear–globular thermoreversible hydrogel ABA type copolymers from dendritic citric acid as the A blocks and poly(ethyleneglycol) as the B block. Eur Polym J 39(7):1491–1500. CrossRefGoogle Scholar
  47. 47.
    Namazi H, Adeli M (2005) Synthesis of barbell-like triblock copolymers, dendritic triazine-block-poly (ethylene glycol)-block-dendritic triazine and investigation of their solution behaviors. Polymer 46(24):10788–10799CrossRefGoogle Scholar
  48. 48.
    Wan T, Xu M, Chen L, Wu D, Cheng W, Li R, Zou C (2014) Synthesis and properties of a dual responsive hydrogel by inverse microemulsion polymerization. J Chem Sci 126(6):1623–1627. CrossRefGoogle Scholar
  49. 49.
    Kim D-G, Kang H, Choi Y-S, Han S, Lee J-C (2013) Photo-cross-linkable star-shaped polymers with poly(ethylene glycol) and renewable cardanol side groups: synthesis, characterization, and application to antifouling coatings for filtration membranes. Polym Chem 4(19):5065–5073. CrossRefGoogle Scholar
  50. 50.
    Wang K, Huang W, Zhou Y, Yan D (2008) Synthesis and characterization of three-arm star-shaped polyethylene glycols with 1,1,1-trihydroxmethylpropane as cores. Front Chem China 3(3):298–303. CrossRefGoogle Scholar
  51. 51.
    Hirao A, Kawasaki K, Higashihara T (2004) Precise synthesis of asymmetric star-shaped polymers by coupling reactions of new specially designed polymer anions with chain-end-functionalized polystyrenes with benzyl bromide moieties. Sci Technol Adv Mater 5(4):469CrossRefGoogle Scholar
  52. 52.
    Elkins CL, Viswanathan K, Long TE (2006) Synthesis and characterization of star-shaped poly (ethylene-co-propylene) polymers bearing terminal self-complementary multiple hydrogen-bonding sites. Macromolecules 39(9):3132–3139CrossRefGoogle Scholar
  53. 53.
    Gasteier P, Reska A, Schulte P, Salber J, Offenhäusser A, Moeller M, Groll J (2007) Surface grafting of PEO-based star-shaped molecules for bioanalytical and biomedical applications. Macromol Biosci 7(8):1010–1023. CrossRefPubMedGoogle Scholar
  54. 54.
    Namazi H, Heydari A (2014) Synthesis of β-cyclodextrin-based dendrimer as a novel encapsulation agent. Polym Int 63(8):1447–1455. CrossRefGoogle Scholar
  55. 55.
    Namazi H, Fard AMP (2011) Preparation of gold nanoparticles in the presence of citric acid-based dendrimers containing periphery hydroxyl groups. Mater Chem Phys 129(1):189–194. CrossRefGoogle Scholar
  56. 56.
    Namazi H, Jafarirad S (2011) Application of hybrid organic/inorganic dendritic ABA type triblock copolymers as new nanocarriers in drug delivery systems. Int J Polym Mater 60:603–619. CrossRefGoogle Scholar
  57. 57.
    Toomari Y, Namazi H, Akbar EA (2015) Synthesis of the dendritic type β-cyclodextrin on primary face via click reaction applicable as drug nanocarrier. Carbohydr Polym 132:205–213. CrossRefPubMedGoogle Scholar
  58. 58.
    Chujo Y, Sada K, Kawasaki T, Saegusa T (1992) Synthesis of non-ionic hydrogel from star-shaped polyoxazoline. Polym J 24(11):1301CrossRefGoogle Scholar
  59. 59.
    Hedenqvist MS, Yousefi H, Malmström E, Johansson M, Hult A, Gedde UW, Trollsås M, Hedrick JL (2000) Transport properties of hyperbranched and dendrimer-like star polymers. Polymer 41(5):1827–1840. CrossRefGoogle Scholar
  60. 60.
    Zhang Y, Zhao Q, Shao H, Zhang S, Han X (2014) Synthesis and characterization of star-shaped block copolymer sPCL-b-PEG-GA. Adv Mater Sci Eng 2014:6. CrossRefGoogle Scholar
  61. 61.
    Iza M, Stoianovici G, Viora L, Grossiord JL, Couarraze G (1998) Hydrogels of poly(ethylene glycol): mechanical characterization and release of a model drug. J Control Release 52(1):41–51. CrossRefPubMedGoogle Scholar
  62. 62.
    Bromberg L (1996) Crosslinked poly(ethylene glycol) networks as reservoirs for protein delivery. J Appl Polym Sci 59(3):459–466.;2-p CrossRefGoogle Scholar
  63. 63.
    Zustiak SP, Leach JB (2010) Hydrolytically degradable poly(ethylene glycol) hydrogel scaffolds with tunable degradation and mechanical properties. Biomacromolecules 11(5):1348–1357. CrossRefPubMedPubMedCentralGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Research Laboratory of Dendrimers and Nanopolymers, Faculty of ChemistryUniversity of TabrizTabrizIran
  2. 2.Research Center for Pharmaceutical Nanotechnology (RCPN)Tabriz University of Medical ScienceTabrizIran

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