Skip to main content
Log in

Optimization of Soybean Oil Based Pressure-Sensitive Adhesives Using a Full Factorial Design

  • Original Paper
  • Published:
Journal of the American Oil Chemists' Society

Abstract

Plant oils are attractive renewable feedstocks for biobased pressure-sensitive adhesives (PSAs). In this study, we investigated how the PSA adhesion properties were influenced by the compositions comprised of epoxidized soybean oil (ESO), 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate (ECHM), dihydroxyl soybean oil (DSO), rosin ester, and cationic photo initiator. When the amounts of ESO and photo-initiator were constant, the variables of ECHM, DSO, and rosin amounts and their interactions were significant in influencing PSA peel adhesion strength, with p values smaller than 0.05 under a 95% significance level. Rosin amounts with the largest coefficient of 0.94 compared to the other variables are the most determinant factors. The peel adhesion strength was higher when using relatively a lower level of ECHM and a higher level of ESO and rosin. A model with the coefficient of determination (R 2) of 95.06% was obtained to describe the relationship between the amount of resin constituents (ECHM, DSO, and rosin) and PSA peel adhesion strength in the experimental variable ranges. The optimal PSA formulation without cohesive failure was (ECHM = 0.04, DSO = 0.7, rosin = 0.7), resulting in a peel adhesion strength of 4.45 N/in. Structure–property relationships of the PSAs were established via thermal and rheological studies.

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.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. PSTC. http://www.pstc.org/. Accessed 11 June 2015

  2. Satas D (1999) Handbook of pressure sensitive adhesive technology. Satas & Associates, Warwick

    Google Scholar 

  3. Report Pm. http://www.marketsandmarkets.com/PressReleases/pressure-sensitive-adhesives.asp. Accessed 11 June 2015

  4. 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 131(17). doi:10.1002/app.40669

  5. Ozturk GI, Pasquale AJ, Long TE (2010) Melt synthesis and characterization of aliphatic low-T g polyesters as pressure sensitive adhesives. J Adhes 86:395–408

    Article  CAS  Google Scholar 

  6. Chicago A, Gutfreud K, Chicago A, Gutfreud K (1971) Pressure-sensitive adhesive tape comprising gluten hydrolypate derivatives, US Patent 3607370

  7. Gerrit E, Alexander S, Yves P, Bernard W (1997) 1996 International symposium on bacterial polyhydroxyalkanoates. NRC Research Press, Canada

    Google Scholar 

  8. Shin J, Martello M, Shrestha M, Wissinger J, Tolman W, Hillmyer M (2011) Pressure-sensitive adhesives from renewable triblock copolymers. Macromolecules 44:87–94

    Article  CAS  Google Scholar 

  9. Pu G, Dubay MR, Zhang J, Severtson SJ, Houtman CJ (2012) Polyacrylates with High Biomass Contents for Pressure-Sensitive Adhesives Prepared via Mini-emulsion Polymerization. Ind Eng Chem Res 51:12145–12149

    Article  CAS  Google Scholar 

  10. Vendamme R, Eevers W (2013) Sweet solution for sticky problems: chemoreological design of self-adhesive gel materials derived from lipid biofeedstocks and adhesion tailoring via incorporation of isosorbide. Macromolecules 46:3395–3405

    Article  CAS  Google Scholar 

  11. Vendamme R, Olaerts K, Gomes M, Degens M, Shigematsu T, Eevers W (2012) Interplay between viscoelastic and chemical tunings in fatty-acid-based polyester adhesives: engineering biomass toward functionalized step-growth polymers and soft networks. Biomacromolecules 13:1933–1944

    Article  CAS  Google Scholar 

  12. Bunker SP, Wool RP (2002) Synthesis and characterization of monomers and polymers for adhesives from methyl oleate. J Polym Sci 40:451–458

    Article  CAS  Google Scholar 

  13. Bunker S, Staller C, Willenbacher N, Wool R (2003) Miniemulsion polymerization of acrylated methyl oleate for pressure sensitive adhesives. Int J Adhes Adhes 23:29–38

    Article  CAS  Google Scholar 

  14. Wool R, Bunker S (2002) Pressure sensitive adhesives from plant oils. Google Patents

  15. Koch CA (2008) Pressure sensitive adhesives made from renewable resources and related methods. Google Patents

  16. Koch CA, Mallya P, Williams CR (2012) Pressure sensitive adhesives based on renewable resources and related methods. Google Patents

  17. Li A, Li K (2014) Pressure-sensitive adhesives based on soybean fatty acids. RSC Adv 4:21521–21530

    Article  CAS  Google Scholar 

  18. Li K, Li A (2013) Vegetable oil-based pressure sensitive adhesives. Google Patents

  19. Maaßen W, Oelmann S, Peter D, Oswald W, Willenbacher N, Meier MAR (2015) Novel insights into pressure-sensitive adhesives based on plant oils. Macromol Chem Phys 216:1609–1618

    Article  Google Scholar 

  20. Maassen W, Meier MAR, Willenbacher N (2016) Unique adhesive properties of pressure sensitive adhesives from plant oils. Int J Adhes Adhes 64:65–71

    Article  CAS  Google Scholar 

  21. Li Y, Sun XS (2014) Di-hydroxylated soybean oil polyols with varied hydroxyl values and their influence on uv-curable pressure sensitive adhesives. J Am Oil Chem Soc 91:1425–1432

    Article  CAS  Google Scholar 

  22. Li Y, Wang D, Sun XS (2015) Oxirane cleavage kinetics of epoxidized soybean oil by water and uv-polymerized resin adhesion properties. J Am Oil Chem Soc 92:121–131

    Article  CAS  Google Scholar 

  23. Ahn BK, Kraft S, Wang D, Sun XS (2011) Thermally stable transparent, pressure-sensitive adhesives from epoxidized and dihydroxyl soybean oil. Biomacromolecules 12:1839–1843

    Article  CAS  Google Scholar 

  24. Ahn BK, Sung J, Kim N, Kraft S, Sun XS (2013) UV-curable pressure-sensitive adhesives derived from functionalized soybean oils and rosin ester. Polym Int 62:1293–1301

    Article  CAS  Google Scholar 

  25. Sun XS, Ahn BK, Wang D (2013) Pressure sensitive adhesives, coatings, and films from plant oils. Google Patents

  26. Li Y, Wang D, Sun XS (2015) Copolymers from epoxidized soybean oil and lactic acid oligomers for pressure-sensitive adhesives. Rsc Adv 5:27256–27265

    Article  CAS  Google Scholar 

  27. Li Y, Sun XS (2015) Polyols from epoxidized soybean oil and alpha hydroxyl acids and their adhesion properties from UV polymerization. Int J Adhes Adhes 63:1–8

    Article  Google Scholar 

  28. Li Y, Sun XS (2015) Camelina oil derivatives and adhesion properties. Ind Crops Prod 73:73–80

    Article  Google Scholar 

  29. Li YH, Sun XS (2015) Synthesis and characterization of acrylic polyols and polymers from soybean oils for pressure-sensitive adhesives. Rsc Adv 5:44009–44017

    Article  CAS  Google Scholar 

  30. Crivello JV, Varlemann U (1995) Mechanistic study of the reactivity of 3,4-epoxycyclohexyl methyl 3′,4′-epoxycyclohexancarboxylate in photoinitiated cationic polymerizations. J Polym Sci 33:2473–2486

    Article  CAS  Google Scholar 

  31. Warwel S, Fehling E, Kunz M (2001) Photoinitiated cationic oligomerization of terminal and internal epoxides. Eur J Lipid Sci Technol 103:133–140

    Article  CAS  Google Scholar 

  32. Sung J, Li Y, Sun XS (2015) Plasticization effects of dihydroxyl soybean oil improve flexibilities of epoxy-based films for coating applications. J Appl Polym Sci 132(14). doi:10.1002/app.41773

  33. Crivello JV (1999) The discovery and development of onium salt cationic photoinitiators. J Polym Sci 37:4241–4254

    Article  CAS  Google Scholar 

  34. Crivello JV, Liu SS (2000) Photoinitiated cationic polymerization of epoxy alcohol monomers. J Polym Sci 38:389–401

    Article  CAS  Google Scholar 

  35. Gafvert E, Shao LP, Karlberg AT, Nilsson U, Nilsson JLG (1994) Contact allergy to resin acid hydroperoxides—hapten binding via free-radicals and epoxides. Chem Res Toxicol 7:260–266

    Article  CAS  Google Scholar 

  36. Wetzel F (1957) Rosin and rosin derivatives in pressure-sensitive adhesives. Rubber Age 82:291–295

    CAS  Google Scholar 

  37. Dahlquist CA (1966) Tack. Adhesion, fundamentals and practice. Maclaren and Sons Ltd, England, pp 143–151

    Google Scholar 

  38. Chang EP (1997) Viscoelastic properties of pressure-sensitive adhesives. J Adhes 60:233–248

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This is Contribution No. 16-185-J from the Kansas Agricultural Experimental Station. Financial support was provided by the USDA-NIFA Biomass Research and Development Initiative program (Grant No. 2012-10006-20230).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Xiuzhi Susan Sun.

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Li, Y., Chou, SH., Qian, W. et al. Optimization of Soybean Oil Based Pressure-Sensitive Adhesives Using a Full Factorial Design. J Am Oil Chem Soc 94, 713–721 (2017). https://doi.org/10.1007/s11746-017-2966-2

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11746-017-2966-2

Keywords

Navigation