Synthesis and characterization of soybean oil-based waxes and their application as paraffin substitute for corrugated coating

Tao Fei; James A. Walker; Kevin L. Vickerman; Kevin L. Vickerman; Darren Jarboe; Ames, IA 50011, United States

Journal of Industrial and Engineering Chemistry, Vol.58, 113-122, February, 2018

DOI10.1016/j.jiec.2017.09.015 Export Citation

Synthesis and characterization of soybean oil-based waxes and their application as paraffin substitute for corrugated coating

Tao Fei¹, James A. Walker², Kevin L. Vickerman², Kevin L. Vickerman², Darren Jarboe³, and Ames, IA 50011, United States^{1, 3, †}

¹Department of Food Science and Human Nutrition, Iowa State University, Ames, IA 50011, United States, USA
²Department of Chemistry, Iowa State University, Ames, IA 50011, United States, USA
³Center for Crops Utilization Research, Iowa State University, Ames, IA 50011, United States, USA

E-mail:

This study focused on modifying the structure of acyl lipid to obtain waxes with desirable properties of paraffin. Structure-function relationships were investigated and established. An increase in chain length significantly increased the hardness of esters. A hydroxyl group on the end of a linear monoester chain further increased hardness. Addition of pendent hydroxyl group increased the cohesiveness of ethylene glycol mono and diesters (EGMD). Incorporating ether groups into diester also significantly increased cohesiveness. Two potential paraffin substitutes were identified. Hydrophobic particles significantly improved water resistance and wet strength of the cardboards and a coating performance competitive to paraffin was achieved.

Keywords:Soybean oil-based wax;Paraffin substitute;Structure?function relationship

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[1] Palou A, Cruz J, Blanco M, Larraz R, Frontela J, Bengoechea CM, Gonzalez JM, Alcala M, Energy Fuels, 28(2), 956 (2014)

[2] Murphy TA, Vegetable oil based wax compositions. US Patent 2004, 6,824,572.

[3] Feuge RO, Vicknair EJ, Lovegren NV, J. Am. Oil Chem. Soc., 29, 11 (1952)

[4] Pelloso TA, Roden AD, Boldt GL, Synthesis of aceto-glyceride fats. US Patent 1995, 5,434,278.

[5] Wang L, Wang T, J. Am. Oil Chem. Soc., 84, 1149 (2007)

[6] Yao L, Lio J, Wang T, Darren J, J. Am. Oil Chem. Soc., 90, 1063 (2013)

[7] Park SJ, Jin FL, Lee JR, Macromol. Rapid Commun., 25(6), 724 (2004)

[8] Chen R, Zhang C, Kessler MR, J. Appl. Polym. Sci. 132 (2014) 41213, doi:http://dx.doi.org/10.1002/APP.41213.

[9] Ferdous K, Uddin R, Uddin R, Khan M, Islam M, Chem. Eng. Sci., 1(4), 62 (2011)

[10] Abes M, Narine S, Chem. Phys. Lipids, 149, 14 (2007)

[11] Callinan T, Crimi J, Mcgee H, Parks A, Schwartz P, US Patent 1964, 3,129,104.

[12] Bouzidi L, Li SJ, Di Biase S, Rizvi SQ, Dawson P, Narine SS, Ind. Eng. Chem. Res., 51(45), 14892 (2012)

[13] Yao L, Wang T, J Am. Oil Chem. Soc., 89, 155 (2012)

[14] Someya T, Stretchable Electrons 2012, Section 7.1.2.

[15] Levitt M, Perutz MF, J. Mol. Biol., 201, 751 (1988)

[16] Perutz MF, Philos. Trans. R. Soc. Lond. Ser. A-Math. Phys. Eng. Sci., 345, 105 (1993)

[17] Brinkley R, Gupta R, AIChE J. 47 (4) (2001) 948, doi:http://dx.doi.org/10.1002/aic.69047041.

[18] Clayden J, Greeves N, Warren S, Organic Chemistry, Oxford University Press, 2001 p. 129.

[19] Sunder JM, Kapole SA, Deshpande S, Super hydrophobic and antistatic composition. U.S. Patent Application 2015, EP2950940 A1.

[20] Depablo J, Biddy M, Nanoparticle modified lubricants and waxes with enhanced properties. U.S. Patent Application 2009, US20090053268 A1.

[21] Hwang HS, Kim S, Singh M, Winkler-Moser JK, Liu SX, J. Am. Oil Chem. Soc., 89, 639 (2012)

[22] Jana S, Martini S, J. Am. Oil Chem. Soc., 93, 543 (2016)

[23] Alexia B, Edmund D, Marangoni A, J. Am. Oil Chem. Soc., 91, 885 (2014)