Skip to main content
Log in

Photo- and pH-sensitive azo-containing cationic waterborne polyurethane

  • Original Paper
  • Published:
Polymer Bulletin Aims and scope Submit manuscript

Abstract

In this study, a novel photo- and pH-sensitive cationic waterborne polyurethane containing side chain aromatic azo groups (Azo-CWPU) was synthesized by step-growth addition polymerization from polyether polylol, isophorone diisocyanate, N-methyl diethanolamine and a new aromatic azo-containing monomer, 2,2′-(4-((4-ethylphenyl)diazenyl)phenylazanediyl)diethanol (EDPD). Azo-CWPU showed a significant hypsochromic contrast to the azo monomer and rapid changes in UV–Vis absorption spectra at different irradiation times. Azo-CWPU dispersion displays bright yellow, orange and red color with the change of pH values. Regarding the orange dispersion, we assume that there is a mixture of the azoic form and the hydrazone form. Compared to cationic waterborne polyurethane dispersion without aromatic azo groups (CWPU), Azo-CWPU dispersion with smaller hydrodynamics radius and more narrow distribution shows good thermodynamic properties of polyurethane.

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.

Institutional subscriptions

Scheme 1
Scheme 2
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12
Fig. 13

Similar content being viewed by others

References

  1. Delaire JA, Nakatani K (2000) Linear and nonlinear optical properties of photochromic molecules and materials. Chem Rev 100(5):1817–1845

    Article  CAS  Google Scholar 

  2. Li Z, Wang J, Liu X, Liu S, Ou J, Yang S (2011) Electrostatic layer-by-layer self-assembly multilayer films based on graphene and manganese dioxide sheets as novel electrode materials for supercapacitors. J Mater Chem 21:3397–3403

    Article  CAS  Google Scholar 

  3. Coady DJ, Khramov DM, Norris BC, Tennyson AG, Bielawski CW (2009) Adapting N-heterocyclic carbene/azide coupling chemistry for polymer synthesis: enabling access to aromatic polytriazenes. Angew Chem Int Ed 48(28):5187–5190

    Article  CAS  Google Scholar 

  4. Natansohn A, Rochon P (2002) Photoinduced motions in azo-containing polymers. Chem Rev 102(11):4139–4175

    Article  CAS  Google Scholar 

  5. Ikeda T, Tsutsumi O (1995) Optical switching and image storage by means of azobenzene liquid-crystal films. Science 268:1873–1875

    Article  CAS  Google Scholar 

  6. Wang G, Wang X (2002) A novel hyperbranched polyester functionalized with azo chromophore: synthesis and photoresponsive properties. Polym Bull 49(1):1–8

    Article  CAS  Google Scholar 

  7. Ikeda T, Mamiya J, Yu Y (2007) Photomechanics of liquid-crystalline elastomers and other polymers. Angew Chem Int Ed 46(4):506–528

    Article  CAS  Google Scholar 

  8. Zhu Z, Li Q, Zeng Q, Li Z, Li Z, Qin J, Ye C (2008) New azobenzene-containing polyurethanes: post-functional strategy and second-order nonlinear optical properties. Dyes Pigm 78(3):199–206

    Article  CAS  Google Scholar 

  9. Liu L, Nakatani K, Pansu R, Vachon J, Tauc P, Ishow E (2007) Fluorescence patterning through photoinduced migration of squaraine-functionalized azo derivatives. Adv Mater 19(3):433–436

    Article  Google Scholar 

  10. Li N, Xu Q, Lu J, Xia X, Wang L (2007) Atom transfer radical polymerization and third-order nonlinear optical properties of new azobenzene-containing side-chain polymers. Macromol Chem Phys 208(4):399–404

    Article  CAS  Google Scholar 

  11. Dautzenberg H, Jaeger W, Kotz J, Philipp B, Seidel Ch, Stscherbina D (1994) Polyelectrolytes: formation, characterization and application. Hanser Publ, Munich

    Google Scholar 

  12. Hara M (1993) Polyelectrolytes: science and technology. Marcel Dekker Inc, New York

    Google Scholar 

  13. Lee S-H, Balasubramanian S, Kim D, Viswanathan N, Bian S, Kumar J, Tripathy S (2000) Azo polymer multilayer films by electrostatic self-assembly and layer-by-layer post azo functionalization. Macromolecules 33(17):6534–6540

    Article  CAS  Google Scholar 

  14. Roberts MJ, Lindsay GA (1998) Thermally stable nonlinear optical films by alternating polyelectrolyte deposition on hydrophobic substrates. J Am Chem Soc 120(43):11202–11203

    Article  CAS  Google Scholar 

  15. Dante S, Advincula R, Frank CW, Stroeve P (1999) Photoisomerization of polyionic layer-by-layer films containing azobenzene. Langmuir 15(1):193–201

    Article  CAS  Google Scholar 

  16. Chattopadhyay DK, Raju KVSN (2007) Structural engineering of polyurethane coatings for high performance applications. Prog Polym Sci 32(3):352–418

    Article  CAS  Google Scholar 

  17. Wang Y, Qiu F, Xu B, Xu J, Jiang Y, Yang D, Li P (2013) Preparation, mechanical properties and surface morphologies of waterborne fluorinated polyurethane-acrylate. Prog Org Coat 76(5):876–883

    Article  CAS  Google Scholar 

  18. Buruiana EC, Buruiana T (2001) Polyurethane cationomers with azobenzene side groups in the flexible component. synthesis, characterization, and properties. Polym J 33:723–731

    Article  CAS  Google Scholar 

  19. Buruiana EC, Buruiana T (2001) New quinone polyetherurethane cationomers. synthesis of some ionenes based on hydroquinone diamine. Polym J 33:42–48

    Article  CAS  Google Scholar 

  20. Buruiana EC, Buruiana T, Strat G, Strat M (2002) Synthesis and optical properties of new polyurethane cationomers with anchored stilbene chromophores. J Polym Sci, Part A: Polym Chem 40(11):1918–1928

    Article  CAS  Google Scholar 

  21. Buruiana EC, Buruiana T (2001) Synthesis of polyetherurethane cationomers with anthraquinone structure. Eur Polym J 37(12):2505–2511

    Article  CAS  Google Scholar 

  22. Samal SK, Dash M, Van Vlierberghe S, Kaplan DL, Chiellini E, van Blitterswijk C, Moroni L, Dubruel P (2012) Cationic polymers and their therapeutic potential. Chem Soc Rev 41:7147–7194

    Article  CAS  Google Scholar 

  23. De Smedt SC, Demeester J, Hennink WE (2000) Cationic polymer based gene delivery systems. Pharm Res 17(2):113–126

    Article  Google Scholar 

  24. Król P, Król B, Stagraczyński R, Skrzypiec K (2013) Waterborne cationomer polyurethane coatings with improved hydrophobic properties. J Appl Polym Sci 127(4):2508–2519

    Article  Google Scholar 

  25. Krol P, Krol B (2012) Surface free energy of polyurethane coatings with improved hydrophobicity. Colloid Polym Sci 290(10):879–893

    Article  CAS  Google Scholar 

  26. ASTM D2572-97 (2010) Standard test method for isocyanate groups in urethane materials or prepolymers. ASTM International, West Conshohocken, PA. http://www.astm.org

  27. Su W, Zhao H, Wang Z, Li Y, Zhang Q (2007) Sphere to disk transformation of micro-particle composed of azobenzene-containing amphiphilic diblock copolymers under irradiation at 436 nm. Eur Polym J 43(2):657–662

    Article  CAS  Google Scholar 

  28. Sekkat Z, Knoll W (2002) Photoreactive organic thin films. Academic Press, San Diego

    Google Scholar 

  29. Dirksen A, de Cola L (2003) Photo-induced processes in dendrimers. C R Chim 6:873–882

    Article  CAS  Google Scholar 

  30. Christie RM (2001) Colour chemistry. The Royal Society of Chemistry, London

    Google Scholar 

  31. Kim YB, Kim HK, Yoo JK, Hong JW (2002) UV-curable polyurethane dispersion for cationic electrodeposition coating. Surf Coat Tech 157(1):40–46

    Article  CAS  Google Scholar 

Download references

Acknowledgments

Financial supports from the National High Technology Research and Development Program of China (No. 2014AAQ00294) and the National Natural Science Foundation of China (No. 51073144) are acknowledged. We thank Dr Feng Jiang for his artwork support and discussions.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Xingyuan Zhang.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Li, J., Zhang, X., Gooch, J. et al. Photo- and pH-sensitive azo-containing cationic waterborne polyurethane. Polym. Bull. 72, 881–895 (2015). https://doi.org/10.1007/s00289-015-1312-9

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00289-015-1312-9

Keywords

Navigation