Abstract
Bio-based acrylated epoxidized jatropha oil (AEJO) was developed using a solvent-free synthetic method, and the structure of the resulting product was confirmed by Fourier transform infrared spectroscopy and proton nuclear magnetic resonance (1H NMR) spectra. Subsequently, an amphiphilic polymer emulsion AEJO-AA was prepared by emulsion polymerization using acrylic acid (AA) and AEJO. Moreover, 2, 3-dialdehyde nanocellulose (DNC) was prepared and combined with AEJO-AA emulsion as a fatliquoring agent for goatskin upper leather. The fatliquored leather shows improved mechanical strength and thermal stability. When the DNC loading is 1.5 wt%, the fatliquored leather exhibits the highest tensile strength of 24.3 MPa, tear strength of 62.2 N/mm and thermal denaturation temperature (Td) of 95.4 °C. The fogging values of the fatliquored leather satisfy the requirements of automobile seat leather. The biochemical oxygen demand (BOD5) and chemical oxygen demand results indicate that the DNC/AEJO-AA emulsion is easily biodegradable. Overall, the developed DNC/AEJO-AA emulsion provides a new strategy in the production of bio-based and ecological polymer fatliquor of leather.
Graphic abstract
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Campanella A, Zhan M, Watt P, Grous AT, Shen C, Wool RP (2015) Triglyceride-based thermosetting resins with different reactive diluents and fiber reinforced composite applications. Compos Part A-Appl S 72:192–199. https://doi.org/10.1016/j.compositesa.2015.02.009
Cossu R, Lai T, Sandon A (2012) Standardization of BOD5/COD ratio as a biological stability index for MSW. Waste Manag 32(8):1503–1508. https://doi.org/10.1016/j.wasman.2012.04.001
Ding W, Zhou J, Zeng Y, Wang YN, Shi B (2017) Preparation of oxidized sodium alginate with different molecular weights and its application for crosslinking collagen fiber. Carbohyd Polym 157:1650–1656. https://doi.org/10.1016/j.carbpol.2016.11.045
Du J, Lu S, Peng B (2016) Amphiphilic acrylate copolymer fatliquor for ecological leather: influence of molecular weight on performances. J Appl Polym Sci 133(20):43440. https://doi.org/10.1002/app.43440
Fathima NN, Baias M, Blumich B, Ramasami T (2010) Structure and dynamics of water in native and tanned collagen fibers: effect of crosslinking. Int J Biol Macromol 47(5):590–596. https://doi.org/10.1021/acs.jafc.6b04482
Fei M, Liu W, Jia A, Ban Y, Qiu R (2018) Bamboo fibers composites based on styrene-free soybean-oil thermosets using methacrylates as reactive diluents. Compos Part A-Appl S 114:40–48. https://doi.org/10.1016/j.compositesa.2018.08.007
Fei M, Liu T, Fu T, Zhang J, Wu Y, Qiu R, Liu W (2019) Styrene-free soybean oil thermoset composites reinforced by hybrid fibers from recycled and natural resources. ACS Sustain Chem Eng 7(21):17808–17816. https://doi.org/10.1021/acssuschemeng.9b04308
Hui Z, Chen X, Wang X, Qiang X, Li X, Meng L (2016) A salt-free pickling chrome tanning approach using a novel sulphonic aromatic acid structure. J Clean Prod 142(4):1741–1743. https://doi.org/10.1016/j.jclepro.2016.11.113
Jessop P (1999) Green Chemistry: theory and practice (Review). Chem Ind 1:1. https://doi.org/10.1039/B926439F
Kalyanaraman C, Devi LV, Porselvam S, Rao JR (2012) Combined advanced oxidation processes and aerobic biological treatment for synthetic fFatliquor used in tanneries. Ind Eng Chem Res 51(50):16171–16181. https://doi.org/10.1021/ie301904g
Lee KY, Aitomaki YB, Lars A, Oksman K, Alexander B (2014) On the use of nanocellulose as reinforcement in polymer matrix composites. Compos Sci Technol 105(15):15–27. https://doi.org/10.1016/j.compscitech.2014.08.032
Liu W, Chen T, Xie T, Qiu R (2016a) Soybean oil-based thermosets with N-vinyl-2-pyrrolidone as crosslinking agent for hemp fiber composites. Compos Part A-Appl S 82:1–7. https://doi.org/10.1016/j.compositesa.2015.11.035
Liu W, Xie T, Qiu R (2016b) Improvement of properties for biobased composites from modified soybean oil and hemp fibers: dual role of diisocyanate. Compos Part A-Appl S 90:278–285. https://doi.org/10.1016/j.compositesa.2016.07.018
Liu W, Fei M, Ban Y, Jia A, Qiu R, Qiu J (2018) Concurrent improvements in crosslinking degree and interfacial adhesion of hemp fibers reinforced acrylated epoxidized soybean oil composites. Compos Sci Technol 160:60–68. https://doi.org/10.1016/j.compscitech.2018.03.019
Liu W, Chen T, Fei M, Qiu R, Yu D, Fu T, Qiu J (2019) Properties of natural fiber-reinforced biobased thermoset biocomposites: effects of fiber type and resin composition. Compos B Eng 171:87–95. https://doi.org/10.1016/j.compositesb.2019.04.048
Lu Y, Larock RC (2010) Novel polymeric materials from vegetable oils and vinyl monomers: preparation, properties, and applications. Chemsuschem 2(2):136–147. https://doi.org/10.1002/cssc.200800241
Lu T, Li Q, Chen W, Yu H (2014) Composite aerogels based on dialdehyde nanocellulose and collagen for potential applications as wound dressing and tissue engineering scaffold. Compos Sci Technol 94(4):132–138. https://doi.org/10.1016/j.compscitech.2014.01.020
Lyu B, Duan XB, Gao DG, Ma JZ, Hou XY, Zhang J (2015) Modified rapeseed oil/silane coupling agent-montmorillonite nanocomposites prepared by in situ method: synthesis and properties. Ind Crop Prod 70:292–300. https://doi.org/10.1016/j.indcrop.2015.03.034
Lyu B, Gao J, Ma J, Gao D, Wang H, Han X (2016) Nanocomposite based on erucic acid modified montmorillonite/sulfited rapeseed oil: preparation and application in leather. Appl Clay Sci 121–122:36–45. https://doi.org/10.1016/j.clay.2015.12.021
Lyu B, Rui C, Gao D, Ma J (2018) Chromium footprint reduction: nanocomposites as efficient pretanning agents for cowhide shoe upper leather. ACS Sustain Chem Eng 6(4):5413–5423. https://doi.org/10.1021/acssuschemeng.8b00233
Ma J, Lyu X, Gao D, Li Y, Lyu B, Zhang J (2014) Nanocomposite-based green tanning process of suede leather to enhance chromium uptake. J Clean Prod 72:120–126. https://doi.org/10.1038/srep20434
Ma J, Duan L, Lu J, Lyu B, Gao D, Wu X (2017a) Fabrication of modified hydrogenated castor oil/GPTMS-ZnO composites and effect on UV resistance of leather. Sci Rep 7(1):3742. https://doi.org/10.1038/s41598-017-03879-3
Ma J, Gao J, Wang H, Lyu B, Gao D (2017b) Dissymmetry gemini sulfosuccinate surfactant from vegetable oil: a kind of environmentally fatliquoring agent in leather industry. ACS Sustain Chem Eng 5(11):10693–10701. https://doi.org/10.1021/acssuschemeng.7b02662
Martín MMB, López JLC, Oller I, Malato S, Pérez JAS (2010) A comparative study of different tests for biodegradability enhancement determination during AOP treatment of recalcitrant toxic aqueous solutions. Ecotox Environ Safe 73(6):1189–1195. https://doi.org/10.1016/j.ecoenv.2010.07.021
Meier MA, Metzger JO, Schubert US (2008) Plant oil renewable resources as green alternatives in polymer science. J Cheminf 39(5):1788–1802. https://doi.org/10.1002/chin.200805269
Miao S, Wang P, Su Z, Zhang S (2014) Vegetable-oil-based polymers as future polymeric biomaterials. Acta Biomater 10(4):1692–1704. https://doi.org/10.1016/j.actbio.2013.08.040
Moon RJ, Martini A, Nairn J, Simonsen J, Youngblood J (2011) Cellulose nanomaterials review: structure, properties and nanocomposites. Chem Soc Rev 40(7):3941–3994. https://doi.org/10.1039/c0cs00108b
Nashy ESHA, Essa MM, Hussain AI (2012) Synthesis and application of methyl methacrylate/butyl acrylate copolymer nanoemulsions as efficient retanning and lubricating agents for chrome-tanned leather. J Appl Polym Sci 124(4):3293–3301. https://doi.org/10.1002/app.35208
Osong SH, Norgren S, Engstrand P (2016) Processing of wood-based microfibrillated cellulose and nanofibrillated cellulose, and applications relating to papermaking: a review. Cellulose 23(1):93–123. https://doi.org/10.1007/s10570-015-0798-5
Patrickios CS, Georgiou TK (2004) Covalent amphiphilic polymer networks. Curr Opin Colloid In 8(1):76–85. https://doi.org/10.1016/s1359-0294(03)00005-0
Pei Z, Zhang J (2013) One-step acrylation of soybean oil (SO) for the preparation of SO-based macromonomers. Green Chem 15(3):641–645. https://doi.org/10.1039/C3GC36961G
Petrović ZS (2008) Polyurethanes from vegetable oils. Polym Rev 48(1):109–155. https://doi.org/10.1080/15583720701834224
Raquez JM, Deléglise M, Lacrampe MF, Krawczak P (2010) Thermosetting (bio) materials derived from renewable resources: a critical review. Prog Polym Sci 35(4):487–509. https://doi.org/10.1016/j.progpolymsci.2010.01.001
Sakai K, Kobayashi Y, Saito T, Isogai A (2016) Partitioned airs at microscale and nanoscale: thermal diffusivity in ultrahigh porosity solids of nanocellulose. Sci Rep 6:20434. https://doi.org/10.1038/srep20434
Wang X, Guo X, Wang H, Guo P (2016a) Effect of linear-hyperbranched amphiphilic phosphate esters on the collagen fibers. J. Agr. Food. Chem. 65(1):104–116. https://doi.org/10.1021/acs.jafc.6b04482
Wang B, Mireles K, Rock M, Li Y, Thakur VK, Gao D, Kessler MR (2016b) Synthesis and preparation of bio-based ROMP thermosets from functionalized renewable isosorbide derivative. Macromol Chem Phys 217(7):871–879. https://doi.org/10.1002/macp.201500506
Williams CK, Hillmyer MA (2008) Polymers from renewable resources: a perspective for a special issue of polymer reviews. Polym Rev 48(1):1–10. https://doi.org/10.1080/15583720701834133
Wu X, Robert J, Martini A (2014) Tensile strength of Iβ crystalline cellulose predicted by molecular dynamics simulation. Cellulose 21(4):2233–2245. https://doi.org/10.1007/s10570-014-0325-0
Yang H, Chen D, Van VT (2015) Preparation and characterization of sterically stabilized nanocrystalline cellouse obtained by period ate oxidation of cellouse fibers. Cellulose 22(3):1743–1752. https://doi.org/10.1007/s10570-015-0584-4
Yuri K, Tsuguyuki S, Akira I (2015) Aerogels with 3D ordered nanofiber skeletons of liquid-crystalline nanocellulose derivatives as tough and transparent insulators. Angew Chem Int Edit 53(39):10253. https://doi.org/10.1002/anie.201406635
Zhang C, Garrison TF, Madbouly SA, Kessler MR (2017) Recent advances in vegetable oil-based polymers and their composites. Prog Polym Sci 71:91–143. https://doi.org/10.1016/j.progpolymsci.2016.12.009
Zhang Y, Li Y, Thakur VK, Gao Z, Kessler MR (2018a) High performance thermosets with tailored properties derived from methacrylated eugenol and epoxy-Based vinyl ester, polym. Int. 67(5):544–549. https://doi.org/10.1002/pi.5542
Zhang Y, Li Y, Thakur VK, Wang L, Gu J, Gao Z, Fan B, Wu Q, Kessler MR (2018b) Bio-based reactive diluents as sustainable replacements for styrene in MAESO resin. RSC Adv 8(25):13780–13788. https://doi.org/10.1039/c8ra00339d
Zhang Y, Thakur VK, Li Y, Garrison TF, Kessler MR (2018c) Soybean-oil-based thermosetting resins with methacrylated vanillyl alcohol as bio-based, low-viscosity comonomer. Macromol Mater Eng 303(1):1700278. https://doi.org/10.1002/mame.201700278
Acknowledgments
This work was supported by The Key Research Project of Shaanxi Province (2020GY-258), National Demonstration Center for Experimental Light Chemistry Engineering Education (Shaanxi University of Science &Technology, 2018QGSJ02-14). Jianzhong Ma was responsible for leading the preparation of this manuscript. Tiantian Wang, Shuai Yu, Yuehong Zhang and Bin Lyu all made substantial contributions to the study design, analysis, interpretation, writing and revision of the manuscript. All authors provided approval for publication and we appreciate the assistance of Zhenhua Tian for NMR analysis.
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
Conflict of interest
All the authors declare that they have no conflict of interest.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Ma, J., Wang, T., Yu, S. et al. Preparation and application of dialdehyde nanocellulose reinforced jatropha oil based polymer emulsions as leather fatliquors. Cellulose 28, 331–346 (2021). https://doi.org/10.1007/s10570-020-03494-y
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10570-020-03494-y