Abstract
Citric acid (CA) can impart good anti-wrinkle properties to treated cotton fabrics, but it also causes significant strength loss and yellowing. In this paper, Trimethyl citrate was applied to anti-crease finishing of cotton fabrics. The transesterification reaction between the ester group of trimethyl citrate and the hydroxyl group of cellulose was investigated and the possible crosslinking and anti-crease mechanism was proposed. Fourier transform infrared spectroscopy (ATR-FTIR) was used to study the changes of infrared spectra of trimethyl citrate in heterogeneous transesterification of cotton fabrics. The results showed that trimethyl citrate can occur heterogeneous transesterification reaction with cellulose. The optimized procedure for treating fabrics was 0.1 mol / L of zinc acetate, 0.2 mol / L of trimethyl citrate, curing temperature of 130 °C, and curing time of 3 min. Consequently, the WRA of treated fabrics could be increased to 132°, 46.7% higher than that of untreated fabrics at 90°, and the strength retention rate (TSR) of treated fabrics could reach 85.7%. This indicates that transesterification has a potential for industrial applications.
Graphic abstract
Similar content being viewed by others
References
Annex BH (2000). Handbook of technical textiles. https://doi.org/10.1201/9781439822906
Boondaeng A et al (2021) Bio-synthesis of itaconic acid as an anti-crease finish for cellulosic fiber fabric RSC. Advances 11:25943–25950. https://doi.org/10.1039/D1RA05037K
Dehabadi VA, Buschmann H-J, Gutmann JS (2013) Durable press finishing of cotton fabrics: an overview. Text Res J 83:1974–1995. https://doi.org/10.1177/0040517513483857
Emam HE (2019b) Generic strategies for functionalization of cellulosic textiles with metal salts. Cellulose 26:1431–1447. https://doi.org/10.1007/s10570-018-2185-5
Emam HE, Darwesh OM, Abdelhameed RM (2020b) Protective cotton textiles via amalgamation of cross-linked Zeolitic imidazole frameworks. Ind Eng Chem Res 59:10931–10944. https://doi.org/10.1021/acs.iecr.0c01384
Emam HE, Ahmed HB, Gomaa E, Helal MH, Abdelhameed RM (2020) Recyclable photocatalyst composites based on Ag3VO4 and Ag2WO4 @MOF@cotton for effective discoloration of dye in visible light. Cellulose 27:7139–7155. https://doi.org/10.1007/s10570-020-03282-8
Emam HE (2019) Antimicrobial cellulosic textiles based on organic compounds. 3 Biotech. https://doi.org/10.1007/s13205-018-1562-y
Gu X, Yang CQ (1998) FT-IR and FT-raman spectroscopy study of the cyclic anhydride intermediates for esterification of cellulose: I. Formation of Anhydrides without a Catalyst Res Chem Intermed 24:979–996. https://doi.org/10.1163/156856798X00672
Hashem M, Ibrahim NA, El-Shafei A, Refaie R, Hauser P (2009) An eco-friendly – novel approach for attaining wrinkle – free/soft-hand cotton fabric. Carbohydr Polym 78:690–703
Huang C, Zhang N, Wang Q, Wang P, Yu Y, Zhou M (2021) Development of hydrophilic anti-crease finishing method for Cotton fabric using alpha-Lipoic acid without causing strength loss and formaldehyde release problem. Prog Org Coatings 151:106042. https://doi.org/10.1016/j.porgcoat.2020.106042
Ibrahim NA, Eid Basma M, El-Aziz EA, Abou Elmaaty TM, Ramadan SM (2017) Multifunctional cellulose-containing fabrics using modified finishing formulations RSC. Advances 7:33219–33230. https://doi.org/10.1039/C7RA05403C
Ibrahim NA, Abo-Shosha MH, Fahmy HM, El-Sayed ZM, Hebeish AA (2008) Hybrids for finishing cotton fabric with durable handle performance. J Mater Proc Tech 200:385–389
Ibrahim NA, Abo-Shosha MH, Elnagdy EI, Gaffar MA (2010) Eco-friendly durable press finishing of cellulose-containing fabrics. J Appl Polym Sci 84:2243–2253
Ibrahim NA, Eid BM, Sharaf SM (2019) Functional Finishes for Cotton based Textiles: Current Situation and Future Trends. Textiles and Clothing
Liu J, Wang B, Xu X, Chen J, Chen L, Yang Y (2016) Green finishing of cotton fabrics using a xylitol-extended citric acid cross-linking system on a pilot scale. ACS Sustain Chem Eng 4:1131–1138. https://doi.org/10.1021/acssuschemeng.5b01213
Liu M, Guo J, Gu Y, Gao J, Liu F (2018) Versatile imidazole-anion-derived ionic liquids with unparalleled activity for alcoholysis of polyester wastes under mild and green conditions. ACS Sustain Chem Eng 6:15127–15134. https://doi.org/10.1021/acssuschemeng.8b03591
Liu XS, Xing TL, Xu DM, Chen GQ (2012) Study on novel eco-friendly anti-creasing agents for natural silk fabric. Chinese Chem Lett 23:665–668. https://doi.org/10.1016/j.cclet.2012.04.013
Lou J, Fan X, Wang Q, Wang P, Yuan J, Yu Y (2019) Oxysucrose polyaldehyde: a new hydrophilic crosslinking reagent for anti-crease finishing of cotton fabrics. Carbohydr Res 486:107783. https://doi.org/10.1016/j.carres.2019.107783
Luo X, Cheng P, Wang W, Fu J, Gao W (2021) Established an eco-friendly cotton fabric treating process with enhancing anti-wrinkle performance. J Eng Fibers Fabr 16:15589250211003454. https://doi.org/10.1177/15589250211003454
Ma F, Hanna MA (1999) Biodiesel production: a review1journal Series #12109, agricultural research division, institute of agriculture and natural resources, University of Nebraska-Lincoln. 1. Bioresour Technol 70:1–15. https://doi.org/10.1016/S0960-8524(99)00025-5
Marae IS, Sharmoukh W, Bakhite EA, Moustafa OS, Abbady MS, Emam HE (2021) Durable fluorescent cotton textile by immobilization of unique tetrahydrothienoisoquinoline derivatives. Cellulose 28:5937–5956. https://doi.org/10.1007/s10570-021-03871-1
Meher LC, Vidya Sagar D, Naik SN (2006) Technical aspects of biodiesel production by transesterification—a review. Renew Sustain Energy Review 10:248–268. https://doi.org/10.1016/j.rser.2004.09.002
Mh A, Mhe A, Ea C, Mmgfa B, Hmf A (2011) Improving easy care properties of cotton fabric via dual effect of ester and ionic crosslinking. Carbohydr Polym 86:1692–1698
Nikles DE, Farahat MS (2005) New motivation for the depolymerization products derived from poly(ethylene terephthalate) (PET) waste: a review. Macromol Mater Eng. https://doi.org/10.1002/mame.200400186
Patil NV, Netravali AN (2020) Multifunctional sucrose acid as a ‘green’ crosslinker for wrinkle-free cotton fabrics. Cellulose 27:5407–5420. https://doi.org/10.1007/s10570-020-03130-9
Peng H, Yang CQ, Wang S (2012) Nonformaldehyde durable press finishing of cotton fabrics using the combination of maleic acid and sodium hypophosphite. Carbohyd Polym 87:491–499. https://doi.org/10.1016/j.carbpol.2011.08.013
Schramm C, Amann A (2019) Formaldehyde-free, crease-resistant functionalization of cellulosic material modified by a hydrolyzed dicarboxylic acid based alkoxysilane/melamine finishing system. Cellulose 26:4641–4654. https://doi.org/10.1007/s10570-019-02391-3
Shamshuddin S, Nagaraju N (2007) Liquid phase transesterification of methyl salicylate and phenol over solid acids: kinetic studies. J Mol Catal Chem 273:55–63. https://doi.org/10.1016/j.molcata.2007.03.066
Tang P, Ji B, Sun G (2016) Whiteness improvement of citric acid crosslinked cotton fabrics: H2O2 bleaching under alkaline condition. Carbohydr Polym 147:139–145. https://doi.org/10.1016/j.carbpol.2016.04.007
Tomke PD et al (2017) Lipase-ultrasound assisted synthesis of polyesters. Ultrason Sonochem 38:496–502. https://doi.org/10.1016/j.ultsonch.2017.03.051
Vanneste M (2014) Easy care finishes for textiles.
Wang Y et al (2017) Effect of anti-creasing component on properties of two-ply cotton yarn. Cellulose 24:3073–3082. https://doi.org/10.1007/s10570-017-1304-z
Wang H, Zhang C, Chu X, Zhu P (2020) Mechanism of Antiwrinkle finishing of cotton fabrics using mixed polycarboxylic acids. Int J Polym Sci 2020:3876595. https://doi.org/10.1155/2020/3876595
Welch CM, Peters JG (2002) Effect of an epoxysilicone in durable press finishing with citric acid. Aatcc Rev 2:21–24
Yang CQ (2001) FTIR Spectroscopy study of ester crosslinking of cotton cellulose catalyzed by sodium hypophosphite. Textile Res J 71:201–206. https://doi.org/10.1177/004051750107100303
Yang CQ, Wang X (1998) Formation of five-membered cyclic anhydride intermediates by polycarboxylic acids thermal analysis and Fourier transform infrared spectroscopy. J Appl Polym Sci 70(13):2711–2718
Yao W, Wang B, Ye T, Yang Y (2013) Durable press finishing of cotton fabrics with citric acid: enhancement of whiteness and wrinkle recovery by Polyol extenders. Ind Eng Chem Res 52:16118–16127. https://doi.org/10.1021/ie402747x
Yatagai M, Takahashi Y (2005) Effect of Citric Acid DP Finishing on Soiling with Particulate Soil of Cotton Fabric. Aatcc Rev 5:17–21
Yoshida T (1971) Mechanism and kinetics of transesterification reaction. J Ind Chem [Japan ] 74:1476
Yousef S, Tatariants M, Tichonovas M, Kliucininkas L, Lukošiūtė S-I, Yan L (2020) Sustainable green technology for recovery of cotton fibers and polyester from textile waste. J Clean Prod 254:120078. https://doi.org/10.1016/j.jclepro.2020.120078
Funding
No funding was received.
Author information
Authors and Affiliations
Contributions
The submission has been received explicitly from all co-authors. And authors whose names appear on the submission have contributed sufficiently to the scientific work and therefore share collective responsibility and accountability for the results.
Corresponding author
Ethics declarations
Conflict of interest
The authors declare that they have no conflict of interest.
Human and animal participate
This article does not contain any studies with human participants or animals performed by any of the authors.
Informed consent
Informed consent was obtained from all individual participants included in the study.
Ethical Statement
I certify that this manuscript is original and has not been published and will not be submitted elsewhere for publication while being considered by Cellulose. And the study is not split up into several parts to increase the quantity of submissions and submitted to various journals or to one journal over time. No data have been fabricated or manipulated (including images) to support your conclusions. No data, text, or theories by others are presented as if they were our own.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Yu, X., Dai, X., Pan, J.J. et al. Transesterification reaction and application in anti-wrinkle finishing of cotton fabrics. Cellulose 28, 11183–11197 (2021). https://doi.org/10.1007/s10570-021-04197-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10570-021-04197-8