Skip to main content
Erschienen in: Polymer Bulletin 4/2015

01.04.2015 | Original Paper

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

verfasst von: Junpei Li, Xingyuan Zhang, James Gooch, Wei Sun, Huaiwei Wang, Kunpeng Wang

Erschienen in: Polymer Bulletin | Ausgabe 4/2015

Einloggen

Aktivieren Sie unsere intelligente Suche, um passende Fachinhalte oder Patente zu finden.

search-config
loading …

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.

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

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!

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!

Literatur
1.
Zurück zum Zitat Delaire JA, Nakatani K (2000) Linear and nonlinear optical properties of photochromic molecules and materials. Chem Rev 100(5):1817–1845CrossRef Delaire JA, Nakatani K (2000) Linear and nonlinear optical properties of photochromic molecules and materials. Chem Rev 100(5):1817–1845CrossRef
2.
Zurück zum Zitat 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 21:3397–3403CrossRef 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 21:3397–3403CrossRef
3.
Zurück zum Zitat 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):5187–5190CrossRef 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):5187–5190CrossRef
4.
Zurück zum Zitat Natansohn A, Rochon P (2002) Photoinduced motions in azo-containing polymers. Chem Rev 102(11):4139–4175CrossRef Natansohn A, Rochon P (2002) Photoinduced motions in azo-containing polymers. Chem Rev 102(11):4139–4175CrossRef
5.
Zurück zum Zitat Ikeda T, Tsutsumi O (1995) Optical switching and image storage by means of azobenzene liquid-crystal films. Science 268:1873–1875CrossRef Ikeda T, Tsutsumi O (1995) Optical switching and image storage by means of azobenzene liquid-crystal films. Science 268:1873–1875CrossRef
6.
Zurück zum Zitat Wang G, Wang X (2002) A novel hyperbranched polyester functionalized with azo chromophore: synthesis and photoresponsive properties. Polym Bull 49(1):1–8CrossRef Wang G, Wang X (2002) A novel hyperbranched polyester functionalized with azo chromophore: synthesis and photoresponsive properties. Polym Bull 49(1):1–8CrossRef
7.
Zurück zum Zitat Ikeda T, Mamiya J, Yu Y (2007) Photomechanics of liquid-crystalline elastomers and other polymers. Angew Chem Int Ed 46(4):506–528CrossRef Ikeda T, Mamiya J, Yu Y (2007) Photomechanics of liquid-crystalline elastomers and other polymers. Angew Chem Int Ed 46(4):506–528CrossRef
8.
Zurück zum Zitat 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):199–206CrossRef 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):199–206CrossRef
9.
Zurück zum Zitat 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):433–436CrossRef 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):433–436CrossRef
10.
Zurück zum Zitat 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):399–404CrossRef 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):399–404CrossRef
11.
Zurück zum Zitat Dautzenberg H, Jaeger W, Kotz J, Philipp B, Seidel Ch, Stscherbina D (1994) Polyelectrolytes: formation, characterization and application. Hanser Publ, Munich Dautzenberg H, Jaeger W, Kotz J, Philipp B, Seidel Ch, Stscherbina D (1994) Polyelectrolytes: formation, characterization and application. Hanser Publ, Munich
12.
Zurück zum Zitat Hara M (1993) Polyelectrolytes: science and technology. Marcel Dekker Inc, New York Hara M (1993) Polyelectrolytes: science and technology. Marcel Dekker Inc, New York
13.
Zurück zum Zitat 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):6534–6540CrossRef 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):6534–6540CrossRef
14.
Zurück zum Zitat Roberts MJ, Lindsay GA (1998) Thermally stable nonlinear optical films by alternating polyelectrolyte deposition on hydrophobic substrates. J Am Chem Soc 120(43):11202–11203CrossRef Roberts MJ, Lindsay GA (1998) Thermally stable nonlinear optical films by alternating polyelectrolyte deposition on hydrophobic substrates. J Am Chem Soc 120(43):11202–11203CrossRef
15.
Zurück zum Zitat Dante S, Advincula R, Frank CW, Stroeve P (1999) Photoisomerization of polyionic layer-by-layer films containing azobenzene. Langmuir 15(1):193–201CrossRef Dante S, Advincula R, Frank CW, Stroeve P (1999) Photoisomerization of polyionic layer-by-layer films containing azobenzene. Langmuir 15(1):193–201CrossRef
16.
Zurück zum Zitat Chattopadhyay DK, Raju KVSN (2007) Structural engineering of polyurethane coatings for high performance applications. Prog Polym Sci 32(3):352–418CrossRef Chattopadhyay DK, Raju KVSN (2007) Structural engineering of polyurethane coatings for high performance applications. Prog Polym Sci 32(3):352–418CrossRef
17.
Zurück zum Zitat 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):876–883CrossRef 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):876–883CrossRef
18.
Zurück zum Zitat Buruiana EC, Buruiana T (2001) Polyurethane cationomers with azobenzene side groups in the flexible component. synthesis, characterization, and properties. Polym J 33:723–731CrossRef Buruiana EC, Buruiana T (2001) Polyurethane cationomers with azobenzene side groups in the flexible component. synthesis, characterization, and properties. Polym J 33:723–731CrossRef
19.
Zurück zum Zitat Buruiana EC, Buruiana T (2001) New quinone polyetherurethane cationomers. synthesis of some ionenes based on hydroquinone diamine. Polym J 33:42–48CrossRef Buruiana EC, Buruiana T (2001) New quinone polyetherurethane cationomers. synthesis of some ionenes based on hydroquinone diamine. Polym J 33:42–48CrossRef
20.
Zurück zum Zitat 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):1918–1928CrossRef 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):1918–1928CrossRef
21.
Zurück zum Zitat Buruiana EC, Buruiana T (2001) Synthesis of polyetherurethane cationomers with anthraquinone structure. Eur Polym J 37(12):2505–2511CrossRef Buruiana EC, Buruiana T (2001) Synthesis of polyetherurethane cationomers with anthraquinone structure. Eur Polym J 37(12):2505–2511CrossRef
22.
Zurück zum Zitat 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 41:7147–7194CrossRef 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 41:7147–7194CrossRef
23.
Zurück zum Zitat De Smedt SC, Demeester J, Hennink WE (2000) Cationic polymer based gene delivery systems. Pharm Res 17(2):113–126CrossRef De Smedt SC, Demeester J, Hennink WE (2000) Cationic polymer based gene delivery systems. Pharm Res 17(2):113–126CrossRef
24.
Zurück zum Zitat Król P, Król B, Stagraczyński R, Skrzypiec K (2013) Waterborne cationomer polyurethane coatings with improved hydrophobic properties. J Appl Polym Sci 127(4):2508–2519CrossRef Król P, Król B, Stagraczyński R, Skrzypiec K (2013) Waterborne cationomer polyurethane coatings with improved hydrophobic properties. J Appl Polym Sci 127(4):2508–2519CrossRef
25.
Zurück zum Zitat Krol P, Krol B (2012) Surface free energy of polyurethane coatings with improved hydrophobicity. Colloid Polym Sci 290(10):879–893CrossRef Krol P, Krol B (2012) Surface free energy of polyurethane coatings with improved hydrophobicity. Colloid Polym Sci 290(10):879–893CrossRef
26.
Zurück zum Zitat ASTM D2572-97 (2010) Standard test method for isocyanate groups in urethane materials or prepolymers. ASTM International, West Conshohocken, PA. http://www.astm.org 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.
Zurück zum Zitat 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):657–662CrossRef 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):657–662CrossRef
28.
Zurück zum Zitat Sekkat Z, Knoll W (2002) Photoreactive organic thin films. Academic Press, San Diego Sekkat Z, Knoll W (2002) Photoreactive organic thin films. Academic Press, San Diego
29.
Zurück zum Zitat Dirksen A, de Cola L (2003) Photo-induced processes in dendrimers. C R Chim 6:873–882CrossRef Dirksen A, de Cola L (2003) Photo-induced processes in dendrimers. C R Chim 6:873–882CrossRef
30.
Zurück zum Zitat Christie RM (2001) Colour chemistry. The Royal Society of Chemistry, London Christie RM (2001) Colour chemistry. The Royal Society of Chemistry, London
31.
Zurück zum Zitat Kim YB, Kim HK, Yoo JK, Hong JW (2002) UV-curable polyurethane dispersion for cationic electrodeposition coating. Surf Coat Tech 157(1):40–46CrossRef Kim YB, Kim HK, Yoo JK, Hong JW (2002) UV-curable polyurethane dispersion for cationic electrodeposition coating. Surf Coat Tech 157(1):40–46CrossRef
Metadaten
Titel
Photo- and pH-sensitive azo-containing cationic waterborne polyurethane
verfasst von
Junpei Li
Xingyuan Zhang
James Gooch
Wei Sun
Huaiwei Wang
Kunpeng Wang
Publikationsdatum
01.04.2015
Verlag
Springer Berlin Heidelberg
Erschienen in
Polymer Bulletin / Ausgabe 4/2015
Print ISSN: 0170-0839
Elektronische ISSN: 1436-2449
DOI
https://doi.org/10.1007/s00289-015-1312-9

Weitere Artikel der Ausgabe 4/2015

Polymer Bulletin 4/2015 Zur Ausgabe

    Marktübersichten

    Die im Laufe eines Jahres in der „adhäsion“ veröffentlichten Marktübersichten helfen Anwendern verschiedenster Branchen, sich einen gezielten Überblick über Lieferantenangebote zu verschaffen.