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Evaluation of crosslinking effect of different polycarboxylic acids with cellulose by acid–base titration and anti-wrinkle performance

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Abstract

Low-molecular-weight copolymers of maleic acid and acrylic acid (P(MA–AA)), itaconic acid and acrylic acid (P(IA–AA)), and trans-aconitic acid and acrylic acid (P(TAA–AA)) were prepared and employed as the crosslinking agents for modification of cotton fabrics. The ester crosslinking effect of cellulose by P(MA–AA), P(IA–AA), and P(TAA–AA) was evaluated and compared with that by the most investigated polycarboxylic acids (PCAs), citric acid (CA) and 1,2,3,4-butanetetracarboxylic acid (BTCA). In detail, the Arrhenius activation energy (Ea) of esterification crosslinking reaction of cellulose with different PCAs was obtained by an acid–base titration method. The data displayed the order of Ea for different PCAs as P(TAA–AA) < P(MA–AA) < P(IA–AA) < BTCA < CA, therefore, P(TAA–AA) indicates the highest reactivity with cellulose. The percentage of carboxylic groups in PCAs esterifying with hydroxyl groups on cellulose and the wrinkle recovery angle of fabrics treated in similar conditions were measured to examine the order of Ea. Evidence proved that P(TAA–AA) showed the highest percentage of carboxylic groups participating in esterification with cellulose in the conditions of 180 °C × 2 min, which corresponds to the lowest Ea of P(TAA–AA). Besides, the distribution of PCA molecules inside cellulose fibers was evaluated by Confocal Raman microscopy. Raman depth mapping images of PCA-treated fibers provide an insight into the diffusion behavior of crosslinking agents in cellulose.

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References

  • Cai Z, Ji B, Yan K, Zhu Q (2019) Investigation on reaction sequence and group site of citric acid with cellulose characterized by FTIR in combination with two-dimensional correlation spectroscopy. Polymers 11:1–13

    Google Scholar 

  • Dai Y, Xu H, Zhong Y, Zhang L, Sui X, Feng X, Wang B, Mao Z (2020a) Study on the effect of different dyeing systems on the interaction of multi-component reactive dyes by Raman spectroscopy. Color Technol 00:1–10

    Google Scholar 

  • Dai Y, Yang B, Ding Y, Xu H, Wang B, Zhang L, Chen Z, Sui X, Feng X, Zhong Y, Mao Z (2020b) Real-time monitoring of multicomponent reactive dye adsorption on cotton fabrics by Raman spectroscopy. Spectrochim Acta A Mol Biomol Spectrosc 230:118051

    Article  CAS  Google Scholar 

  • Dai Y, Zhou P, Xu H, Zhong Y, Wang B, Zhang L, Sui X, Feng X, Mao Z (2021) Confocal Raman depth imaging tracking on the diffusion process of single and two-component reactive dyes in a single viscose fiber. Dyes Pigments 188:109160

    Article  CAS  Google Scholar 

  • Gao H (2004) Organic chemistry. Higher Education Press, Beijing

    Google Scholar 

  • Harifi T, Montazer M (2012) Past, present and future prospects of cotton cross-linking: new insight into nano particles. Carbohydr Polym 88:1125–1140

    Article  CAS  Google Scholar 

  • Hu H, Dong X, Tang W, Yao J, He J (2018) Effects of molecular structures of poly-carboxylic acids on crosslinking reaction. Dye Finis 01:0001–0005

    CAS  Google Scholar 

  • Ji B, Yan K, Sun G (2016) Investigation on functional properties of 1,2,3,4-butanetetracarboxylic acid cross-linked fabrics impacted by molecular structures and chemical affinity of catalysts. Ind Eng Chem Res 55:5216–5222

    Article  CAS  Google Scholar 

  • Liang T, Yan K, Zhao T, Ji B (2020) Synthesis of a low-molecular-weight copolymer by maleic acid and acrylic acid and its application for the functional modification of cellulose. Cellulose 27:5665–5675

    Article  CAS  Google Scholar 

  • Liang T, Yan K, Zhao T, Liu Y, Ji B (2021a) High strength retention of cellulose fibers crosslinking with synthesized low-molecular-weight copolymers of itaconic acid and acrylic acid. Cellulose 28:1167–1178

    Article  CAS  Google Scholar 

  • Liang T, Yan K, Zhao T, Ji B (2021b) Preparation of multiple-reactive-site and flexible crosslinking agent with transaconitic acid and acrylic acid and its application for three-dimensional crosslinking of cellulose. Text Res J. https://journals.sagepub.com/doi/10.1177/00405175211067823

  • Luo X, Shao D, Xu C, Wang Q, Gao W (2019) An eco-friendly way to whiten yellowish anti-wrinkle cotton fabrics using TBCC-activated peroxide low-temperature post-bleaching. Cellulose 26:3575–3588

    Article  CAS  Google Scholar 

  • Luo X, Shao D, Xu C, Wang Q, Gao W (2020) Whitening citric acid treated cotton fabrics by a TBCC-activated peroxide post-bleaching. Cellulose 27:5367–5376

    Article  CAS  Google Scholar 

  • Qi H, Zhao C, Qing F, Yan K, Sun G (2016) Antiwrinkle finishing of cotton fabrics with 5-(carbonyloxysuccinic)-benzene-1,2,4-tricarboxylic acid: comparison with other acids. Ind Eng Chem Res 55:11850–11856

    Article  CAS  Google Scholar 

  • Schramm C (2020) High temperature ATR-FTIR characterization of the interaction of polycarboxylic acids and organotrialkoxysilanes with cellulosic material. Spectrochim Acta A Mol Biomol Spectrosc 243:118815

    Article  CAS  Google Scholar 

  • Schramm C, Rinderer B, Bobleter O (1997) Kinetic data for the crosslinking reaction of polycarboxylic acids with cellulose. J Soc Dyers Colour 113(12):346–349

    Article  CAS  Google Scholar 

  • Schramm C, Rinderer B (1999a) Influence of additives on the formation of unsaturated PCAs produced during durable-press curing with citric acid. J Soc Dyers Colour 115:306–311

    CAS  Google Scholar 

  • Schramm C, Rinderer B (1999b) Optimizing citric acid DP finishing to minimize fabric yellowing. Text Chem Color 31:23–27

    CAS  Google Scholar 

  • Yan K (2009) Dyeing and finishing process and principle, vol 1. China Textile & Apparel Press, Hong Kong

    Google Scholar 

  • Yang CQ (1991) FT-IR spectroscopy study of the ester crosslinking mechanism of cotton cellulose. Text Res J 61:433–440

    Article  CAS  Google Scholar 

  • Yang CQ, Bakshi GD (1996) Quantitative analysis of the nonformaldehyde durable press finish on cotton fabric: acid-base titration and infrared spectroscopy. Text Res J 66(6):377–384

    Article  CAS  Google Scholar 

  • Yang CQ, Wang X (1996) Formation of cyclic anhydride intermediates and esterification of cotton cellulose by multifunctional carboxylic acids: an infrared spectroscopy study. Text Res J 66:595–603

    Article  CAS  Google Scholar 

  • Yang CQ, Wang D (2000) Evaluating ester crosslinking of cotton fabric by a polycarboxylic acid using acid-base titration. Text Res J 77(7):615–620

    Article  Google Scholar 

  • Yang CQ, Wang X, Kang I (1997) Ester crosslinking of cotton fabric by polymeric carboxylic acids and citric acid. Text Res J 67:334–342

    Article  CAS  Google Scholar 

  • Yang B, Dai Y, Zhong Y, Zhang L, Xu H, Wang B, Sui X, Feng X, Chen Z, Mao Z (2020) A study of the diffusion behaviour of reactive dyes in cellulose fibres using confocal Raman microscopy. Color Technol 136:503–511

    Article  CAS  Google Scholar 

  • Zhao M, Zhou X (2005) Kinetics of esterification reaction of cotton fabric polymerization-crosslinking system. Proc Nation Symp Finish Print Dye 6:9–12

    CAS  Google Scholar 

Download references

Acknowledgments

This research was funded by the National Natural Science Foundation of China (51803025), the Fundamental Research Funds for the Central Universities (2232020D-21), the State Key Laboratory of Bio-Fibers and Eco-Textiles (KF2020213), and the State Key Laboratory of New Textile Materials and Advanced Processing Technologies (FZ2020010).

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Correspondence to Bolin Ji.

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Liang, T., Yan, K., Zhao, T. et al. Evaluation of crosslinking effect of different polycarboxylic acids with cellulose by acid–base titration and anti-wrinkle performance. Cellulose 29, 4229–4241 (2022). https://doi.org/10.1007/s10570-022-04525-6

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