Butanetetracarboxylic Acid Research Articles

Cellulase Treatment of Durable Press Finished Cotton Fabric: Effects on Fabric Strength, Abrasion Resistance, and Handle

Enzyme washing is commonly used as a wet process technique to improve textile handle, appearance, and other surface characteristics of cottons in the industry. In this research, we have studied the effects of cellulase treatment on tensile strength, flex abrasion resistance, and handle of cotton fabric crosslinked by a polycarboxylic acid. The fabric is first treated with cellulase (pre-curing treatment), then crosslinked by 1,2,3,4- butanetetracarboxylic acid (BTCA). The fabric is also crosslinked by BTCA first then treated with cellulase (post-curing treatment). We compare the performance of the durable press (DP) finished cottons treated with cellulase using these two different procedures, and we find that the pre-curing cellulase treatment has a more positive influence on fabric handle than the post-curing treatment, but it also causes significantly higher fabric strength loss than the post-curing treatment. We also find that the difference in wrinkle resistance of the DP finished cotton fabrics with the two treatments is not significant. Considering the fact that a DP finishing process reduces fabric strength, the pre-curing cellulase treatment method should be used only for heavy cotton fabrics with high original strength.

Effect of mercerisation and crosslinking on the dyeing properties of ramie fabric

The dyeing of ramie fabrics crosslinked with 1,2,3,4‐butanetetracarboxylic acid has been studied using a typical direct dye CI Direct Red 81. Adsorption time curves from finite baths of untreated ramie, tension‐mercerised ramie, slack‐mercerised ramie and cotton fabrics have been compared. It has been found that mercerisation improved the equilibrium adsorption and dyeing rate, while it reduced the maximum dye adsorption and equilibrium constant on ramie fabric. Crosslinking with butanetetracarboxylic acid decreased most of these parameters related to the dyeing profile, although the activation energy of dyeing was increased. A pore model approach has been used to explain the changes in dyeing properties arising from the crosslinking of ramie using butanetetracarboxylic acid.

Effect of Crosslinking Treatment on the Crystallinity, Crystallite Size, and Strength of Cotton Fibers

In this paper, cotton fibers and their fabric are treated with butanetetracarboxylic acid (BTCA) with the catalyst sodium hypophosfite (SHP) at different concentrations of treating agent and different curing temperatures. Results show that low curing temperatures and low agent concentrations have a slight effect on the reduction of crystallinity and crystallite size, but when the curing temperature is higher than 180°C and the BTCA concentration is higher than 6%, crystallite size and crystallinity decrease significantly. This may be ascribed to the acidic erosion of the surface of the crystals at high temperatures. An initial slight crystallinity loss induces high strength loss in the fabric. This is perhaps due to the initial slight reduction of crystallinity, which causes serious interfacial binding strength losses between the crystals and the amorphous regions.

Durable antimicrobial treatment of cotton fabrics using N‐(2‐hydroxy)propyl‐3‐trimethylammonium chitosan chloride and polycarboxylic acids

AbstractN‐(2‐hydroxy)propyl‐3‐trimethylammonium chitosan chloride (HTCC), a water‐soluble chitosan quaternary ammonium derivative, was used as an antimicrobial agent for cotton fabrics. HTCC has a lower minimum inhibition concentration (MIC) against Staphylococcus aureus, Klebsiella pneumoniae, and Escherichia coli compared to that of chitosan; however, the imparted antimicrobial activity is lost on laundering. Thus crosslinking agents were utilized to obtain a durable antimicrobial treatment by immobilizing HTCC. Several crosslinkers such as dimethyloldihydroxyethylene urea (DMDHEU), butanetetracarboxylic acid (BTCA), and citric acid (CA) were used with HTCC to improve the laundering durability of HTCC treatment by covalent bond formation between the crosslinker, HTCC and cellulose. The polycarboxylic acid treatment was superior to the DMDHEU treatment in terms of prolonged antimicrobial activity of the treated cotton after successive laundering. Also, the cotton treated with HTCC and BTCA showed improved durable press properties without excessive deterioration in mechanical strength or whiteness when compared to the citric acid treatment. With the addition of only 0.1% HTCC to BTCA solutions, the treated fabrics showed durable antimicrobial activity up to 20 laundering cycles. The wrinkle recovery angle and strength retention of the treated fabrics were not adversely affected with the addition of HTCC. Therefore, BTCA can be used with HTCC in one bath to impart durability of antimicrobial activity along with durable press properties to cotton fabric. © 2003 Wiley Periodicals, Inc. J Appl Polym Sci 88: 1567–1572, 2003

Surface chemical analysis of 1,2,3,4-butanetetracarboxylic acid modified cotton

Time-of-Flight Secondary Ion Mass Spectrometry (ToF-SIMS) and X-ray Photoelectron Spectroscopy (XPS) have been used to characterise butanetetracarboxylic acid (BTCA) powder and BTCA modified cotton fibre surface. The wash durability of crease resist BTCA finish at the cotton surface has been demonstrated and enhanced binding of sodium cations to the carboxyl rich fibre surface observed. Similarly increased affinity of copper ions to the polycarboxylic acid treated cotton was observed. Domestic laundering of the copper impregnated BTCA fabric in a perborate containing detergent produced increased strength loss relative to comparably laundered unmodified cotton and DMDHEU treated cotton fabric.

Two‐step durable press treatment of cotton fabric

In this paper cotton fabrics were treated by two different methods with polycarboxylic acids (citric acid and butanetetracarboxylic acid) for durable press performance. The first was a two‐step method in which the fabric was initially treated with citric acid and then treated by butanetetracarboxylic acid. The other was a mixed method in which the fabric was treated with a solution containing the two mixed polycarboxylic acids. Following the treatments, the wrinkle recovery angle, strength and strength retention of the resulting fabric were measured and compared.

Durable press finish of cotton fabric using malic acid as a crosslinker

It has been considered that malic acid,α-hydroxy succinic acid, could not form crosslinks in the cellulosic materials unless activated by other polycarboxylic acids such as butanetetracarboxylic acid or citric acid because there are only two carboxylic acids per molecule available for the formation of one anhydride intermediate. However we found that the dicarboxylic malic acid with sodium hypophosphite catalyst without the addition of other crosslinkers was able to improve wrinkle resistance of cotton up to 294° (dry WRA) and 285° (wet WRA), which is a measure of crosslinking level in cotton.1H FT-NMR, FT-IR and GPC analysis indicated the in-situ formation of an trimericα, β-malic acid with a composition of 1:3 through the esterification between hydroxyl group and one of carboxylic groups in malic acid during curing. The crosslinking of cotton was attributed to the trimericα, β-malic acid, a tetracarboxylic acid, which can form two anhydride rings during curing. The influence of crosslinking conditions such as concentrations of malic acid and catalyst, pH of the formulation bath, and curing temperature were investigated in terms of imparted wrinkle resistance and whiteness. The addition of reactive polyurethane resin in the formulation slightly increased the mechanical strength retention of crosslinked fabric coupled with additional increase in wrinkle resistance.

An FTIR Study of Anhydride Formation on Heating Butane Tetracarboxylic Acid in the Presence of Various Catalysts

Polycarboxylic acids containing more than three carboxylic acid groups react with hydroxyl groups in cotton cellulose and crosslink cotton through stable ester bonds. The aim of this research is to use variable temperature diffuse reflectance infrared spectros copy to study anhydride formation from the thermal dehydration reaction of 1,2,3,4- butanetetracarboxylic acid (BTCA) in the presence of one of three catalysts—sodium carbonate, sodium hypophosphite, and cyanamide. An environmental chamber equipped with a temperature controller is attached to the infrared spectrometer to obtain diffuse reflectance spectra at elevated temperatures and ambient pressure. With this spectroscopic method, the temperature profile of anhydride formation from BTCA in the presence of a particular catalyst is clearly visible.

Fixation of Chitosan on Cross-Linked Cellulose Fabrics with Polycarboxylic Acids

Fixation of chitosan on cellulosic fabrics with using a cross-linking reaction of polycarboxylic acid has been investigated. Cotton fabrics that was cross-linked with polycarboxylic acid such as citric acid (CA) and butanetetracarboxylic acid (BTCA) showed to have appreciable amount of free carboxylic acid residues on the fabric that came from the polycarboxylic acid without participating the cross-linking reaction. Chitosan could be fixed on the fabric with good fastness to acid washing by padding and following curing process. Relatively high wrinkle recovery characteristics of the cross-linked and chitosan fixed fabric was obtained. The fixation of the chitosan on cotton fabric could also be done by the simpler process that consists of padding of mixture of polycarboxylic acid and chitosan onto untreated cotton fabric followed by high-temperature curing. With this process, simultaneous chitosan fixation could be achieved with the cross-linking reaction of polycarboxylic acid with cotton substrate. Intermolecular ester linkage formation by the polycarboxylic acid was suggested by the FTIR measurements.

Formation of five-membered cyclic anhydride intermediates by polycarboxylic acids: Thermal analysis and Fourier transform infrared spectroscopy

Butanetetracarboxylic acid (BTCA) has been used as the most effective nonformaldehyde crosslinking agent for cotton and wood pulp cellulose. Our previous research has indicated that a polycarboxylic acid esterifies cellulose in two steps: the formation of a five-membered cyclic anhydride intermediate by the dehydration of two adjacent carboxyl groups, and the reaction between cellulose and the anhydride intermediate to form an ester linkage. In this research, we investigated the formation of carboxylic anhydrides by BTCA and other polycarboxylic acids in powder forms, and as finishes applied to cotton fabric using thermal gravimetry, differential scanning calorimetry, and Fourier transform infrared spectroscopy. We found that BTCA and other polycarboxylic acids in powder forms start to form five-membered cyclic carboxylic anhydrides when the temperature reaches the vicinity of their melting points. The formation of carboxylic anhydride is accelerated above the melting points. We also found that BTCA forms anhydrides at lower temperatures when it is applied to cotton fabric as a finish. An increase in temperature increases both the amount of anhydride and the amount of ester formed on the cotton fabric. © 1998 John Wiley & Sons, Inc. J Appl Polym Sci 70: 2711–2718, 1998

Mechanical Strength of Durable Press Finished Cotton Fabrics

Severe tensile strength loss is the major disadvantage of durable press finished cotton fabrics. Such strength losses have been attributed to two main factors: acid-catalyzed depolymerization and crosslinking of cellulose molecules. In this research, we inves tigate the effects of acid degradation and cellulose crosslinking on the tensile strength of cotton fabric crosslinked by polycarboxylic acids. Multifunctional carboxylic acids such as butanetetracarboxylic acid (BTCA) are used as nonformaldehyde crosslinking agents for cotton fabrics. The strength loss caused by acid degradation is an irreversible process, and the magnitude of the loss is determined by the curing temperature and time, the dissociation constants of the acid, and the concentration and pH of the acid solution applied to the fabric. Crosslinking of cellulose molecules by a polycarboxylic acid causes a reversible fabric strength loss, which increases as the degree of crosslink ing increases. The magnitude of tensile strength loss caused by acid degradation and that by crosslinking for cotton fabrics treated with BTCA is measured. Losses caused by crosslinking can be restored after the ester crosslinking is hydrolyzed under alkaline conditions.

Durable press finishing of cotton with polycarboxylic acids. II. Ester crosslinking of cotton with dithiosuccinic acid derivative ofS-triazine

The preparation of an alternative polycarboxylic acid to replace the most promising but expensive crosslinking reagent butanetetracarboxylic acid (BTCA) was reported in Part I.1 Part II studies the efficiency of the crosslinking of cotton with the dithiosuccinic acid derivative of s-triazine (HDTST). Diffuse Reflectance infrared (DR FTIR) spectroscopy in combination with wrinkle recovery angle measurements (WRA) were used to analyse the efficiency of cotton cellulose crosslinking. Energy Dispersive X-ray analysis (EDX) of the polycarboxylic acid-finished cotton fabric was performed to study sulphur distribution. © 1997 John Wiley & Sons, Inc. J Appl Polym Sci 66: 171–177, 1997

Quantitative Analysis of the Nonformaldehyde Durable Press Finish on Cotton Fabric: Acid-Base Titration and Infrared Spectroscopy

Butanetetracarboxylic acid (BTCA) has been a promising nonformaldehyde durable press finish for cotton fabrics to replace N-methyol reagents. Acid-base titration and Fourier transform infrared (FT-IR) spectroscopy are applied as quantitative analytical techniques to determine the amount of BTCA applied to cotton fabric and the amount of ester formed on the fabric after a curing process. Acid-base equilibria of BTCA are discussed. We find that FT-IR spectroscopy is a reliable quantitative analytical technique for quantifying BTCA and its ester on cotton fabric when the calibration standards are established by acid-base titration. Calibration curves and regression equations are pre sented. To determine the amount of ester formed on the finished cotton fabric using FT-IR spectroscopy, it is necessary to use a sodium hydroxide solution to quantitatively convert carboxyl to carboxylate. The acid-base equilibria associated with this procedure are also discussed.

Formaldehyde-free zein fiber—preparation and investigation

A novel dry-spinning method for the preparation of zein fiber without using formaldehyde is presented. The fiber thus obtained had good stability to boiling aqueous acetic acid solution with breaking tenacity and elongation of 1.0 g/d and 30%, respectively. Citric acid and butanetetracarboxylic acid were used as nonformaldehyde crosslinking agents for the preparation of zein fiber successfully. Using polycarboxylic acids have advantages such as no toxicity and low sensitivity to the variation of processing conditions over formaldehyde containing stabilizers. The effects of crosslinking before and after stretching on improvement of fiber properties were discussed. Fiber morphological structure was also examined by means of wide angle x-ray diffraction and sonic velocity. © 1996 John Wiley & Sons, Inc.

Formaldehyde‐free zein fiber—preparation and investigation

A novel dry-spinning method for the preparation of zein fiber without using formaldehyde is presented. The fiber thus obtained had good stability to boiling aqueous acetic acid solution with breaking tenacity and elongation of 1.0 g/d and 30%, respectively. Citric acid and butanetetracarboxylic acid were used as nonformaldehyde crosslinking agents for the preparation of zein fiber successfully. Using polycarboxylic acids have advantages such as no toxicity and low sensitivity to the variation of processing conditions over formaldehyde containing stabilizers. The effects of crosslinking before and after stretching on improvement of fiber properties were discussed. Fiber morphological structure was also examined by means of wide angle x-ray diffraction and sonic velocity. © 1996 John Wiley & Sons, Inc.

Effect of Catalyst on the Pore Structure and Performance of Cotton Cellulose Crosslinked with Butanetetracarboxylic Acid

Pore structures of cotton crosslinked with butanetetracarboxylic acid (BTCA) and different catalysts were assessed. The catalysts included NaH2PO2.H 2O, Na- H2PO 3.2.5H2O, Na2HPO3.5H2O, NaH2PO4.H2O, Na2HPO4, Na4P2O7, and Na2CO3. Treatments were applied to all-cotton printcloth using a pad-dry-cure process. Textile performance properties were determined for the treated fabrics. Pore size dis tribution was assessed on Wiley milled fabric using a reverse gel permeation chro matographic technique. The water soluble molecular probes employed were sugars and ethylene glycols. Plots were prepared of V, , the accessible internal water, versus the molecular diameters of the probes. In addition, internal structure differences were elucidated by moisture regain, considered to be a measure of the internal surface of the cotton fiber in the conditioned state, and water of imbibition, a measure of internal volume in the water-swollen state. There were definite patterns in textile performance with the different catalysts. The total volume in residual small pores was inversely related to the resilience level achieved, and retained breaking strength was directly related to the volume in residual small pores. Patterns with respect to abrasion resistance were more complex. Because BTCA add-ons were comparable, the data suggest that the more effective catalysts, NaH2PO2 and NaH2PO3, are effecting either a greater number of crosslinks in the cotton or producing crosslinks that differ in actual structure.

Synthesis of 1, 2, 3, 4-butanetetracarboxylic acid from the irradiation of aqueous succinic acid

This paper deals with the action of ionizing radiation on diluted aqueous solutions of succinic acid in order to synthesize 1, 2, 3, 4- butanetetracarboxylic acid. This compound has a variety of industrial and agricultural applications. The chemical synthesis of this compound involves several steps. In contrast the radiation-induced synthesis can be achieved in one step and with a good yield. The results obtained show that one of the most important reactions was the demerization of the target compound yielding the tetracarboxylic acid.

Effect of Preswelling Treatments on the Properties of Cotton Fibers Crosslinked with 1,2,3,4 Butanetetracarboxylic Acid

Relations were studied between fiber structure and mechanical properties of cotton fibers crosslinked with 1,2,3,4 butanetetracarboxylic acid (BTCA). BTCA was either applied directly to the fibers (NPT) or after they had received a swelling treatment with caustic soda (MER), liquid ammonia (LAT), or monomethylamine (MMA). In some instances BTCA was applied before the caustic treated fibers had been dried (NDMER). The water retention value (WRV) of MER fibers was markedly higher than that of NPT, LAT, or MMA fibers. After BTCA treatment, however, the WRV of MER fibers fell sharply, but that of MMA or LAT samples did not. Thus the WRV s of BTCA MER and NDMER fibers approached those of MMA and LAT products. The breaking force of BTCA fibers approached the same value at high BTCA contents, with or without mercerization or methylamine preswelling. It appeared that LAT cotton might retain greater strength than the other samples at high BTCA contents. The breaking extensions of BTCA fibers that had received a preswelling treatment were higher than those of fibers that had not been pretreated. Properties of MER and NDMER BTCA fibers were similar, even though it appeared that the BTCA was more uniformly distributed in the NDMER fibers. The breaking twist angle ( BTA ) was determined as a measure of brit tleness ; the BTA relation with extension for the BTCA samples was similar to a previously determined relation for cotton treated with dimethyloldihydroxyethyleneurea.

Alkali Metal Salts of Hydroxy Acids as Catalysts in Durable Press Finishing with Butanetetracarboxylic Acid

Alkali metal salts of hydroxy acids have been investigated as catalysts for esterification cross-linking of cotton with 1,2,3,4-butanetetracarboxylic add to produce cotton fabrics with smooth drying properties. Of the sodium salts of several acids studied, the sodium citrates produce fabrics with the best appearance properties. The sodium citrates serve both as donors of citric acid for cross-linking and of sodium ions for catalysis of the esterification of cotton cellulose by the two polycarboxylic acids. Although the use of citric acid as an extender for the more expensive butanetracarboxylic acid has been reported in non-formaldehyde finishing of cotton fabrics for smooth drying properties the catalyst used was sodium hypophosphite. Comparisons are made between fabrics finished with the phosphorus-containing system and the butanetetracarboxylic acid/sodium citrate systems. Textile properties, fabric whiteness, effect of pad bath pH, and extent of esterification are discussed.

Pore Structure of Cotton Fabrics Crosslinked with Formaldehyde-Free Reagents

Pore structures of cotton fabric crosslinked with several formaldehyde-free durable press reagents are elucidated, and results are compared with those for the industry standard, DMDHEU (dimethyloldihydroxyethyleneurea). The formaldehyde-free reagents were BTCA (butanetetracarboxylic acid), DHDMI (dihydroxydimethylimidazolidinone), and the glyoxal/glycol system; the fabric was an 80 × 80 cotton print-cloth. Treatments were designed to impart the same degree of conditioned wrinkle recovery (WRA) to the fabric. A reverse gel permeation chromatographic technique was used to follow changes in pore size distribution. Columns were prepared by settling water slurries of the ground cotton in a conventional manner. Two series of water soluble solutes, which were series of oligomeric sugars and ethylene glycols, were used to study the elution characteristics of the unmodified and crosslinked samples. Internal structure differences were also elucidated by means of moisture regain, considered to be a measure of the internal surface of the cotton fiber in the conditioned state, and water of imbibition, a measure of internal volume in the water-swollen state. Formaldehyde-free crosslinking reagents effect a lower level of collapse of the internal pore structure of the cotton fiber than does DMDHEU at generally comparable levels of resilience.