Sizing and desizing of cotton and polyester yarns using liquid and

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Sizing and desizing of cotton and polyester yarns using liquid and supercritical carbon dioxide with non-fluorous CO2-philes as size compounds ANU ANTONY, Anila Raj, Jyothi P Ramachandran, Resmi M. Ramakrishnan, Scott L. Wallen, and Poovathinthodiyil Raveendran ACS Sustainable Chem. Eng., Just Accepted Manuscript • DOI: 10.1021/acssuschemeng.8b02699 • Publication Date (Web): 27 Jul 2018 Downloaded from http://pubs.acs.org on July 27, 2018

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ACS Sustainable Chemistry & Engineering

Sizing and desizing of cotton and polyester yarns using liquid and supercritical carbon dioxide with non-fluorous CO2-philes as size compounds Anu Antony,a Anila Raj,a Jyothi P. Ramachandran,a Resmi M. Ramakrishnan,b Scott L. Wallenc and Poovathinthodiyil Raveendrana* a

Department of Chemistry, University of Calicut, Kerala, India- 673635. Department of Chemistry, SNGS College, Pattambi, Kerala, India- 679306. c Florida Polytechnic University, Division of Science, Arts & Mathematics, 4700 Research Way Lakeland, FL 33805-8531. * E-mail: [email protected]; Tel: (+91) 9446537724 b

KEYWORDS: Supercritical CO2, Sizing, Textile, Cotton, Polyester, Yarns. ABSTRACT: In this work, we demonstrate a completely green and economically viable sizing and desizing process for cotton and polyester yarns using liquid and supercritical CO2 as alternative solvent systems and inexpensive, non-fluorous CO2-philes as size compounds. The size performance of sucrose octaacetate (SOA), α-D-glucose pentaacetate (AGLU), and poly(ethylene glycol) (PEG) are studied. The mechanical properties of the sized yarn as well as the optical and electron microscopic studies are carried out to evaluate the quality of sizing. It is shown that SOA is the most suitable candidate as size compound as it provides the best surface coverage and improved mechanical properties for the yarn, plausibly assisted by the formation of a smooth and glassy coating of SOA on the yarn. For AGLU and SOA, complete desizing is easily effected by virtue of their complete miscibility with liquid and supercritical CO2 at low pressures. It is observed that the desizing of the PEG-sized yarn is difficult due to the poor solubility of the size in the CO2-based solvent systems. The entire size materials and the solvent can be recycled, making it a zero-pollution technology that can easily be translated into industry at an affordable cost.

INTRODUCTION Sizing and desizing of yarn are the two important processes in the textile industry with potential impact on the environment, demanding a search for environmentally benign alternative strategies. Sizing is a process employed to protect the yarn from damage during the fabric weaving. The main objectives of sizing are the protection of the surface of the yarn, improvement of its tensile strength, weight, and elasticity as well as to remove the projecting fibers that interfere with the weaving process.1 High-speed fabric weaving requires smooth yarn and this can be achieved only by proper sizing. Presently, starch and polyvinyl alcohol are the most commonly used size agents in the industry.2 Conventional method of sizing involves drawing the yarn through a concentrated, aqueous dispersion of the size and then drying it.3 This consumes tremendous amount of water and requires energy-intensive processes for drying. After the weaving process, the sized fabric material is washed with water, generating lots of waste water, causing contamination of the natural water reservoirs down the line. This is problematic, especially in developing countries like

India where the textiles industry, and, in particular, the cotton industry, is ranked as the second largest employment provider. The use of liquid and supercritical (sc) carbon dioxide as a green alternative solvent has been gaining momentum in the recent years due to its environmentally benign attributes such as non-toxicity, ease of solvent removal, and importantly, its low cost and abundance.4-9 The emission control directives around the world also encourages the use of CO2 as an industrially viable alternative solvent. These aspects have led to the utilization of this solvent in diverse industrial disciplines such as material processing, biomolecular separations, food and pharmaceutical processing, dry cleaning, polymer synthesis and processing, etc.10-14 Although the initial capital costs associated with the high-pressure equipment for compressing CO2 into a dense state are greater, a recent increase in the number of CO2-based processes reveals that the advantages of using CO2 outweighs its demerits in most cases.4 Based on the high miscibility of fluorocarbons with liquid and scCO2, Fulton and coworkers3,15 proposed in 1996 that the CO2-solvent platform can serve as an alternative medium for the sizing and desizing of yarn using fluoropolymers as size agents. However, this wonderful method couldn’t take off as

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an economically viable method in the textile industry, plausibly due to the high cost of the size and other potential environmental issues associated with the fluorinated size compounds. Fluorocarbons are well-known systems in terms of their miscibility with the CO2-solvent systems. A more detailed understanding of the solvent behavior of CO2 in the later years suggested that it is possible to design renewable and low-cost CO2-philes16-18 based on the ability of the carbon atom of the charge separated CO2 molecule to act as a Lewis acid (LA) and the oxygen atoms as Lewis base (LB) units, facilitating the dissolution of such molecular systems via sitespecific LA-LB interactions, often assisted by cooperative CH…O hydrogen bonds.19-21 It was also shown that many hydrocarbon-based systems can be tailored with CO2-philic functionalities such as acetate (sugar acetates, for example) moieties, leading to the identification of many inexpensive CO2philes.17,18 The enthalpy-driven high solubility of these systems in liquid and scCO2 by virtue of the CO2-specific LA-LB and C-H…O hydrogen bonds is also reflected in the unique phase behavior of peracetylated sugars reported by Enick and coworkers.22 Sugar acetates have been identified to have advantages over other CO2-philes due to its benign features such as biocompatibility, renewability and non-toxicity. Apart from these, several polymers such as poly(ethylene glycol),23 poly(vinyl acetate),24 poly(vinyl pyrrolidone)25 etc. were also identified to melt under moderate CO2 pressures by virtue of site-specific interactions between CO2 and the various solute functionalities.14,19,26,27 Among these, PEG has received special attention due to its non-toxicity, low volatility, low cost and biocompatibility and hence have found wide-spread use in pharmaceutical, food, and cosmetic industries.28,29 In this work, we demonstrate a completely green strategy for the sizing and desizing of yarns, both cotton and polyester, using CO2 as the medium along with highly CO2-philic size materials such as Sucrose Octaacetate (SOA), α-D-Glucose Pentaacetate (AGLU), and Poly(ethylene glycol) (PEG). The molecular structures of these systems are given (Figure 1). AGLU and SOA melt under moderate pressures of gas phase CO2 and are completely miscible with liquid and scCO2 and the dense CO2 solutions of these compounds can be easily used for sizing the yarns. On the other hand, the low molecular fragments polyethylene glycol (MW = 1500) melt at 35 °C under pressures of CO2 (∼90 bar) and expands further, although the CO2-melt of PEG is not completely miscible with liquid or scCO2.23 Thus, one can easily develop a CO2-melt strategy for sizing yarn by drawing the yarn through the CO2melt of PEG. The ease of solvent removal makes these strategies inherently dry and green processes, without requiring any further drying. It is demonstrated herein that the CO2-based sizing and desizing has the potential to be developed into an ideal zero-pollution technology with wider implications for the textile industry. All the size materials used are inexpensive and environmentally benign and can be completely recycled along with the solvent. MATERIALS AND METHODS SCF grade CO2 (99.9 %) was supplied by Chemix Speciality Gases and was used without any additional purification. SOA (99.8% purity), AGLU (99% purity) and PEG-1500 (bio-ultra grade) were purchased from Sigma Aldrich and was used as

received. Unsized cotton and polyester yarns were purchased from Madura coats Pvt. Ltd. The experimental set up consists of a high pressure stainless steel view cell with an internal volume of 10 cm3, fitted with a sapphire window, connected to a CO2 pump (JASCO, Japan), back pressure regulator (BPR) and a water bath. The experimental setup is illustrated (Figure S1). In a typical experiment, the cell was loaded with about 0.5 g of the size compound. Approximately 30 cm long bare yarn was inserted from the top of the cell. CO2 was pumped into the view cell to the desired pressures (at 65 bar and 25 0C for SOA and AGLU, 90 bar and 35 0C for PEG) and size compound is made completely mixed or melt with CO2 under continuous stirring. After about 5 minutes, the CO2 gas is depressurized at a constant rate of 1 bar/min using the back pressure regulator and the sized yarns obtained are collected and characterized. The same facility is used for the desizing of the sized yarns by washing the yarn with supercritical CO2 (at 90 bar and 35 0C). The size material left behind after the desizing process can be collected and reused as such.

Figure 1. Structures of the CO2-philic size compounds: (a) SOA (b) AGLU and (c) PEG. The masses of the samples before and after sizing, and after desizing, are recorded using an analytical balance. Sizing of the cotton yarn using SOA is also performed with Acetone (Ac) and Ethyl acetate (EA) as solvents by drawing the yarn through Ac/EA dispersion of SOA (0.5 g SOA in 5 ml Ac/EA) followed by drying. Optical microscopic images of the samples are acquired using a Leica M80 stereo microscope. Surface morphologies of the samples are investigated using Carl Zeiss Gemini 300 Field-Emission Scanning Electron Microscope. Mechanical properties of the samples are measured on a Shimadzu AG-Xplus 10 kN Universal Testing Machine. In order to investigate the abrasion resistance offered by the yarn, the mechanical properties of the sized and unsized yarns were evaluated before and after the abrasion process, adopting the procedure developed by Fulton et al.3,15 The abrasion process was carried out by pulling the yarn three times over a 900 edge with corner radius of 0.5 mm.


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ACS Sustainable Chemistry & Engineering RESULTS AND DISCUSSION As discussed earlier, the main objective of this work is to examine whether it is possible to enable the sizing and desizing of yarn using inexpensive and renewable CO2-philes such as SOA, AGLU, and PEG. The experiments are carried out on cotton yarn (CY) as well as polyester yarn (PY). It is important to note that these size compounds are very different in their response to the treatment with CO2. Both SOA and AGLU belong to the same class of compounds, where the CO2-philicity is arising from the site-specific interactions between the acetate moieties and CO2. Both these size compounds are hydrophobic in nature. In fact, the self-interaction cross-section and the lattice energy of SOA are plausibly less than those for AGLU, as evidenced by the lower melting point of SOA (83 0C) than that of AGLU (109 0C), in spite of the higher molecular weight of SOA. It is interesting to note that after treatment with CO2 and the solvent removal, SOA forms a glass, while AGLU forms a crystalline material.30 In fact, it has been reported by Wallen and co-workers that SOA has a glass transition around 29 °C.31 In the case of PEG, which is generally hydrophilic, the CO2-induced deliquescence may be due to the Lewis acid (LA)-Lewis base (LB) interactions between the carbon atom of the CO2 molecule and ether oxygen of PEG. It will also be pertinent to investigate how these size materials will bind to the two entirely different classes of yarns, CY and PY. The method used for sizing is detailed in the experimental section. Three different CO2-philes are chosen as the size candidates for the sizing of both CY and PY. The desizing of these systems is also carried out later using scCO2. The choice of liquid CO2 for sizing and scCO2 for desizing is primarily due to the higher rate of diffusion in the sc state, which can help a more efficient wash of the sized yarn. The optical microscopic images of bare CY along with those after sizing with SOA (CY-SOA), AGLU (CY-AGLU) and PEG (CY-PEG) are presented (Figure 2). It is very clear that in CY-SOA, the CY has a very smooth, transparent, reasonably uniform, thick, and a glassy coating of SOA on that. The individual microfibers of CY are buried underneath the SOA coating. This may be attributed to the glass formation of SOA upon CO2-treatment. On the other hand in the case of CYAGLU, the AGLU coating has discontinuous and powdery features with the individual microfibers protruding out of the coated yarn. A thick and uniform coating was noticed for PEG, however, the PEG coating has a viscous liquid-like appearance even after the CO2 removal, plausibly due to its low lattice energy.

Figure 2. Optical microscopic images of (a) bare CY b) CY-SOA c) CY-AGLU and d) CY-PEG.

Similar sizing experiments are also carried out in the case of the PY. The optical microscopic images of PY coated with SOA (PY-SOA), AGLU (PY-AGLU), and PEG (PY-PEG) are presented (Figure 3). It is observed that the size material forms similar coatings on PY as observed in the case of CY. While SOA forms a smooth, glassy, and translucent coating on PY, AGLU forms a white, powdery coating on PY. The SOA sizing appears to be of much superior quality as compared to both AGLU and PEG.

Figure 3. Optical microscopic images of a) bare PY b) PY-SOA c) PY-AGLU and d) PY-PEG.

In the case of PEG, the coating is more of a semi-solid type as observed in the “starching” using water. While SOA provides a thick glassy coating with stronger protection to the yarn, the greasy coating formed by PEG might be of some use from a mechanical perspective, by reducing friction during the weaving process. In the case of PY, both SOA and PEG give smooth, translucent coatings with complete coverage of the individual microfibers of the yarn while the AGLU coating is less effective. In order to evaluate the nature of the coatings more closely, SEM images of the unsized and sized yarns are recorded to investigate the degree of encapsulation and the uniformity of the coating. The SEM image of bare CY, CY-SOA, CYAGLU and CY-PEG are shown (Figure 4). In the case of bare



CY, the individual fibers are clearly visible and they are projecting out. Also, some small pores are observed on the smooth SOA coating on CY, plausibly due to the bubble formations as a result of the evolution of CO2 from the CO2-melt of SOA.

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sessment on how the sizing has improved the suitability of the yarns for the weaving process. The results of the mechanical properties of the bare, sized CYs and sized PYs are summarized (Table 1). Size Compound

Tensile Strength (N/mm2)

Percentage Elongation

Young’s Modulus (N/mm2) before abrasion

Young’s Modulus (N/mm2) after abrasion

232.0

10.7

17.8

15.8

CY-SOA

472.4

15.0

31.7

26.4

CY-AGLU

362.9

11.7

31.0

17.6

CY

CY-PEG

271.0

14.0

19.3

16.2

PY

723.6

16.1

45.0

41.6

PY-SOA

1156.5

16.4

72.1

65.7

PY-AGLU

1019.2

16.6

61.1

48.4

PY-PEG

871.9

16.8

54.0

49.3

Figure 4. FE-SEM images of a) bare CY b) CY-SOA c) CYAGLU and d) CY-PEG.

On the other hand, AGLU has successfully penetrated into the yarn structure, but appears to be just a filler material without much binding to the yarn. In CY-PEG also, a thick coating is observed without any of the individual fibers protruding out. SEM of PY, PY-SOA, PY-AGLU and PY-PEG are shown (Figure 5) and are revealing a smooth, uniform coating for PY-SOA without any of the microfibers being projected outside. SOA appears to strongly adhere to the yarn surface and has also penetrated between the individual fibers. Coating with AGLU is not very effective as observed in the earlier cases, in terms of the encapsulation efficiency. In PY-AGLU, individual fibers are clearly visible even after the coating. Both SOA and PEG encapsulate the PY better than AGLU. Among the trio, SOA was found to be superior to its counterparts in terms of coating on PY.

Figure 5. FE-SEM images of (a) bare PY (b) PY-SOA (c) PYAGLU and (d) PY-PEG.

Mechanical properties such as Tensile strength, % Elongation, and Young’s modulus are measured for CY-SOA, CY-AGLU, CY-PEG, PY-SOA, PY-AGLU, and PY-PEG to make an as-

Table 1. Mechanical properties of the bare and sized yarns. Sizing with all the three size candidates resulted in an increase in the tensile strength for both CYs and PYs. Among these, tensile strength is found to be the highest for the SOA-coated yarn, followed by AGLU and finally, PEG. The tensile strength is almost doubled for the CY-SOA while an enhancement of 60% is observed for the tensile strength of the PY-SOA system. All the three compounds have improved the mechanical properties of the yarns (CY and PY) as evident from the values of the Young’s modulus for each material. From the analysis of the data on mechanical properties, it is also evident that the % elongation of all the sized yarns is higher than the corresponding bare yarn. The results also reveal that although all the three size compounds stiffened the yarns, SOA showed the best response as a sizing agent, both in the case of CY and PY. In all the three cases, the abrasion process caused a reduction in the Young’s modulus, although the abrasion had minimal effects in the case of the SOA-sizing. In the case of AGLU, the stiffness of the yarn has been reduced significantly after abrasion. This may be due to the poor surface coverage of the size on the surface of the yarn as evidenced by the SEM images. For both SOAand PEG –sizing, the surface coverage of the size on the yarn is almost complete and one would expect similar stiffness characteristics and abrasion resistance in both the cases. However, there are significant differences between these two size compounds. In the case of SOA, the stiffness of the yarn has increased considerably after sizing and it also shows high resistance to abrasion, plausibly due to the formation of the glassy SOA coating and improved binding of the size with the yarns. On the other hand, although the surface coverage of the PEG on the yarn is observed to be good, the waxy nature of the coating results in low stiffness and abrasion resistance as compared to SOA. It can be summarized from the UTM measurements that while all the three CO2-philes considered here are suitable size candidates for textile industry in terms of strength, stiffness and % elongation, SOA is the most suitable


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ACS Sustainable Chemistry & Engineering size material in terms of the quality of the coating and the mechanical properties. Both the optical microscopy as well SEM studies show that the hairiness of the yarns has been reduced upon sizing due to the surface coverage with the size. In this case also, SOA provides the best protection to the yarn as revealed by the optical and SEM images. A comparison between the CO2-solvent system and the conventional solvents such as Acetone (Ac) and Ethyl Acetate (EA) for the sizing process is also made using SOA as the size material. The optical microscopic and SEM images (Figure 6) of CY sized with SOA using ethyl acetate (CY-SOA-EA) and acetone (CY-SOA-Ac) revealed that although SOA is highly soluble in both Ac and EA, it does not form a uniform and good coating with these conventional solvents and the SOA does not bind effectively to the yarn as observed in the case of the CO2 solvent system.

most easily available among the sugar acetates, provides a strong basis for the transformation of the process into an industrial technology. CONCLUSIONS AND OUTLOOK In this work, we have investigated the possibility of utilizing liquid and scCO2 as a green alternative medium for the sizing and desizing of both cotton and polyester yarns for textile industry using inexpensive, non-fluorous, CO2-philes. We considered three size compounds, viz., SOA, AGLU, and PEG, by virtue of their CO2-philic nature. Among the systems studied, SOA is found to be the most ideal candidate as a size material for the CO2-based processing. Sizing of both cotton and polyester yarns with SOA resulted in a smooth, uniform, and glassy coating and improved mechanical properties of the yarn as required for weaving. Overall, the results clearly indicate that the combination of SOA as an inexpensive and environmentally benign size material and liquid and scCO2 as a green solvent system can be developed into a transformational technology for the textiles industry with zero pollution since both the size and the solvent can be easily and completely recycled. Since SOA is a very inexpensive agricultural product, the technology can be made economically viable.

ASSOCIATED CONTENT Supporting Information Table S1. Mass determination studies Figure S1. Schematic diagram of the experimental set up Figure S2. SEM images of desized yarns “This material is available free of charge via the Internet at http://pubs.acs.org.” Figure 6. Sizing using conventional solvents: (a) & (b) Optical microscopic images of CY-SOA-EA and CY-SOA-Ac; (c) & (d) FE-SEM images of CY-SOA-EA and CY-SOA-Ac.

Finally, sizing was gravimetrically estimated by measuring the mass of the bare yarn prior to and after coating with the size compound. Finally, the yarn was washed with scCO2 (at 90 bar and 35 0C) to remove the size compound and reweighed. An increase in the mass of the yarn upon coating is observed (Table S1). It also shows that the sugar acetates can be completely washed off during the desizing process using scCO2. It can also be concluded from the SEM images (Figure S2) that desizing using scCO2 is very effective for SOA and AGLU sized yarns. Since PEG is not completely miscible with liquid and scCO2, the complete desizing of the PEG-sized yarn is rather difficult, posing a major disadvantage in using this system as a size compound in the textiles industry. It is interesting to note that while AGLU and SOA are equally miscible with liquid and scCO2, SOA forms a much better and smooth coating on the yarn. As can be seen from the optical images, the SOA forms a transparent and continuous coating on the yarn, removing the hairiness of the yarn. The mechanical properties are also much more superior for the SOA coated yarns. One of the plausible reasons is the formation of the SOA glass upon its CO2-treatment while such glass formation is absent in the case of AGLU.31 Better controls on such coatings can be achieved by superior process controls in the engineering designs. In any case, SOA being the cheapest and the

AUTHOR INFORMATION Corresponding Author Professor Dr. Poovathinthodiyil Raveendran

Department of Chemistry, University of Calicut, Kerala, India-673 635 E-mail: [email protected]; Tel: (+91) 9446537724

Funding Sources Kerala State Council for Science, Technology & Environment (KSCSTE)

ACKNOWLEDGEMENT The authors gratefully acknowledge a Project funding from the Kerala State Council for Science, Technology & Environment (KSCSTE) under the SRS scheme. AA thanks UGC for a JRF. Central Sophisticated Instrumentation Facility(CSIF), University of Calicut, and the National Institute of Technology (NIT), Calicut are acknowledged for providing the analytical facilities.

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TOC: An economically viable and environmentally responsible route for the sizing and desizing of cotton and polyester yarns using liquid and supercritical carbon dioxide as solvent and non- fluorous CO2- philes as the size compounds.


Sizing and desizing of cotton and polyester yarns using liquid and

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