Polymer Bulletin

, Volume 76, Issue 6, pp 3093–3112 | Cite as

Fabrication of acrylic pressure-sensitive adhesives containing maleimide for heat-resistant adhesive applications

  • Xiaoyong Zhang
  • Huihui Liu
  • Lipei Yue
  • Yongping BaiEmail author
  • Jinmei HeEmail author
Original Paper


In the area of pressure-sensitive adhesives (PSAs), acrylic PSAs have been successfully applied in many fields, including self-adhesive tapes, sign labels, carrier-free tapes, double-sided tapes and protective films, but applications of heat-resistant acrylic PSAs are relatively rare. In this study, the thermal stability of acrylic polymer containing maleimide (Mal) functional groups has been investigated. The PSAs were synthesized by acrylic monomers and Mal through copolymerization. The influence of Mal on the viscosity, molecular weight (Mw, Mn), glass transition temperature, thermogravimetric analysis and contact angle of acrylic PSAs was also studied. The adhesion performance and thermal stability of acrylic PSAs could be significantly enhanced by increase in Mal content of the synthesized resin. After 3 h of treatment in drying oven at 170 °C, the modified PSAs can be peeled (180°) off from the substrate without residues on substrate surface at room temperature, while the non-modified acrylic PSAs possessed residues after treatment from 110 °C. The maximum 180° peel strength of modified PSA films was 12.7 N/25 mm when the content of Mal was 7.5 wt%.


Maleimide Heat-resistant Adhesion Acrylic Pressure-sensitive adhesives 


  1. 1.
    Czech Z (2004) Development in the area of UV-crosslinkable solvent-based pressure-sensitive adhesives with excellent shrinkage resistance. Eur Polym J. Google Scholar
  2. 2.
    Feldstein MM, Bovaldinova KA, Bermesheva EV, Moscalets AP, Dormidontova EE, Grinberg VY, Khokhlov AR (2014) Thermo-switchable pressure-sensitive adhesives based on poly(N-vinyl caprolactam) non-covalently cross-linked by poly(ethylene glycol). Macromolecules. Google Scholar
  3. 3.
    Czech Z, Kowalczyk A, Kabatc J, Świderska J, Shao L, Bai YP (2012) Influence of selected photoinitiators type II on tack, peel adhesion, and shear strength of UV-crosslinked solvent-borne acrylic pressure-sensitive adhesives used for medical applications. Polym Bull. Google Scholar
  4. 4.
    Maassen W, Meier MAR, Willenbacher N (2016) Unique adhesive properties of pressure sensitive adhesives from plant oils. Int J Adhes Adhes. Google Scholar
  5. 5.
    Czech Z, Kabatc J, Kowalczyk A, Sowa D, Madejska E (2015) Application of selected 2-methylbenzothiazoles AS cationic photoreactive crosslinkers for pressure-sensitive adhesives based on acrylics. Int J Adhes Adhes. Google Scholar
  6. 6.
    Gower MD, Shanks RA (2004) The effect of chain transfer agent level on adhesive performance and peel master-curves for acrylic pressure sensitive adhesives. Macromol Chem Phys. Google Scholar
  7. 7.
    Hosel M, Sondergaard RR, Jorgensen M, Krebs FC (2013) Comparison of UV-curing, hotmelt, and pressure sensitive adhesive as roll-to-roll encapsulation methods for polymer solar cell. Adv Eng Mater. Google Scholar
  8. 8.
    Karyu N, Noda M, Fujii S, Nakamura Y, Urahama Y (2016) Effect of adhesive thickness on the wettability and deformability of polyacrylic pressure-sensitive adhesives during probe tack test. J App Polym Sci. Google Scholar
  9. 9.
    Czech Z, Shao L, Kowalczyk A, Kabatc J, Cheng XQ, Świderska J (2013) Photocrosslinking of solvent-based acrylic pressure-sensitive adhesives (PSA) by the use of selected photoinitiators type I. J Adhes Sci Technol. Google Scholar
  10. 10.
    Mess A, Vietzke JP, Rapp C, Francke W (2011) Qualitative analysis of tackifier resins in pressure sensitive adhesives using direct analysis in real time time-of-flight mass spectrometry. Anal Chem. Google Scholar
  11. 11.
    Chen JH, Zhao Q, Wang Y, Luo F, Shen L, Wu K, Liang LY, Lu M (2016) Improvement in mechanical properties and thermal stability of solvent-based pressure-sensitive adhesives based on triazine heterocyclic monomer. J Appl Polym Sci. Google Scholar
  12. 12.
    Vendamme R, Schüwer N, Eevers W (2014) Recent synthetic approaches and emerging bio-inspired strategies for the development of sustainable pressure-sensitive adhesives derived from renewable building blocks. J Appl Polym Sci. Google Scholar
  13. 13.
    Shen SB, Ishida H (1996) Synthesis and characterization of polyfunctional naphthoxazines and related polymers. J Appl Polym Sci.;2-P Google Scholar
  14. 14.
    Czech Z, Kowalczyk A, Kabatc J, Świderska J (2013) Thermal stability of poly(2-ethylhexyl acrylates) used as plasticizers for medical application. Polym Bull. Google Scholar
  15. 15.
    Leibler L (2005) Nanostructured plastics: joys of self-assembling. Prog Polym Sci. Google Scholar
  16. 16.
    Hawker CJ, Wooley KL (2005) The convergence of synthetic organic and polymer chemistries. Science. Google Scholar
  17. 17.
    Jennings GK, Brantley EL (2004) Physicochemical properties of surface-initiated polymer films in the modification and processing of materials. Adv Mater. Google Scholar
  18. 18.
    Ishida H, Sanders DP (2000) Improved thermal and mechanical properties of polybenzoxazines based on alkyl-substituted. J Polym Sci Part B Polym Phys.;2-X Google Scholar
  19. 19.
    Czech Z, Kowalczyk A, Ortyl J, Świderska J (2013) Acrylic pressure-sensitive adhesives containing SiO2 nanoparticles. Polish J Chem Technol. Google Scholar
  20. 20.
    Czech Z, Pełech R (2009) The thermal degradation of acrylic pressure-sensitive adhesives based on butyl acrylate and acrylic acid. Prog Org Coat. Google Scholar
  21. 21.
    Ishida H, Ohba S (2005) Synthesis and characterization of maleimide and norbornene functionalized benzoxazines. Polymer. Google Scholar
  22. 22.
    Kumar AA, Dinakaran K, Alagar M (2003) Preparation and characterization of siliconized epoxy-1,2-bis (maleimido) ethane intercrosslinked matrix materials. J Appl Polym Sci. Google Scholar
  23. 23.
    Park S, Jin F, Lee J (2004) Synthesis and thermal properties of epoxidized vegetable oil. Macromol Rapid Commun. Google Scholar
  24. 24.
    Kumar AA, Alagar M, Rao RMVGK (2002) Synthesis and characterization of siliconized epoxy-1,3-bis (maleimido) benzene intercrosslinked matrix materials. Polymer. Google Scholar
  25. 25.
    Shen SB, Ishida H (1999) Dynamic mechanical and thermal characterization of high-performance polybenzoxazines. J Polym Sci Part B Polym Phys.;2-0 Google Scholar
  26. 26.
    Ning X, Ishida H (2003) Phenolic materials via ring-opening polymerization: synthesis and characterization of bisphenol-A based benzoxazines and their polymers. J Polym Sci, Part A: Polym Chem. Google Scholar
  27. 27.
    Agag T, Takeichi T (2003) Synthesis and characterization of novel benzoxazine monomers containing allyl groups and their high performance thermosets. Macromolecules. Google Scholar
  28. 28.
    Kimura H, Matsumoto A, Sugito H, Hasegawa K (2001) New thermosetting resin from poly(p-vinylphenol) based benzoxazine and epoxy resin. J Appl Polym Sci.;2-H Google Scholar
  29. 29.
    Zhang GB, Zhang JM, Wang SG, Shen DY (2003) Miscibility and phase structure of binary blends of polylactide and poly (methyl methacrylate). J Polym Sci Part B Polym Phys. Google Scholar
  30. 30.
    Schmitz PJ, Holubka JW (1995) Investigation of the “Surface” and “Interphase” composition of adhesion promoter/thermoplastic olefin systems: the effect of adhesion promoter bake temperature. J Adhes. Google Scholar
  31. 31.
    Deetz MJ, Fahey JE, Smith BD (2001) NMR studies of hydrogen bonding interactions with secondary amide and urea groups. J Phys Org Chem. Google Scholar
  32. 32.
    Fang C, Jing Y, Zong YJ, Lin ZX (2016) Effect of N,N-dimethylacrylamide DMA on the comprehensive properties of acrylic latex pressure sensitive adhesives. Int J Adhes Adhes. Google Scholar
  33. 33.
    Czech Z, Sowa D, Kowalska J (2013) UV-crosslinkable photoreactive pressure-sensitive adhesives synthesized from butyl acrylate and 4-acryloyloxy benzophenone. Int Lett Chem Phys Astron 71:105–111Google Scholar
  34. 34.
    Lu XC, Cao G, Niu ZF, Pan QM (2014) Viscoelastic and adhesive properties of single-component thermo-resistant acrylic pressure sensitive adhesives. J Appl Polym Sci. Google Scholar
  35. 35.
    Tan HS, Li L, Chen Z, Song YH, Zheng Q (2005) Phase morphology and impact toughness of impact polypropylene copolymer. Polymer. Google Scholar
  36. 36.
    Xu K, Selby JC, Shannon MA, Economy J (2004) Adhesion mechanisms in the solid-state bonding technique using submicrometer aromatic thermosetting copolyester adhesive. J Appl Polym Sci. Google Scholar
  37. 37.
    Zhang L, Cao YJ, Wang L, Shao L, Bai YP (2016) Polyacrylate emulsion containing IBOMA for removable pressure sensitive adhesives. J Appl Polym Sci. Google Scholar
  38. 38.
    Peykova Y, Lebedeva OV, Diethert A, Muller-Buschbaum P, Willenbacher N (2011) Adhesive properties of acrylate copolymers: effect of the nature of the substrate and copolymer functionality. Int J Adhes Adhes. Google Scholar
  39. 39.
    Shui XJ, Shen YD, Fei GQ, Wang HH, Zhu K (2015) The effect of nonionic monomer HAM on properties of cationic surfactant-free acrylic/alkyd hybrid emulsion. J Appl Polym Sci. Google Scholar
  40. 40.
    Aramendia E, Barandiaran MJ, Grade J, Blease T, Asua JM (2005) Improving water sensitivity in acrylic films using surfmers. Langmuir. Google Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2018

Authors and Affiliations

  1. 1.School of Chemistry and Chemical EngineeringHarbin Institute of TechnologyHarbinChina
  2. 2.Institute of Chemical MaterialsChina Academy of Engineering PhysicsMianyangChina
  3. 3.Wuxi HIT New Material Research Institute Co., LtdWuxiChina

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