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THE FUTURE DIRECTIONS of TANNING* by ANTHONY D

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THE FUTURE DIRECTIONS of TANNING* by ANTHONY D 7 QUO VADIT CHROMIUM? THE FUTURE DIRECTIONS OF TANNING* by ANTHONY D. COVINGTON* British School of Leather Technology The University of Northampton BOUGHTON GREEN ROAD, NORTHAMPTON NN2 7AL, UK ABSTRACT La pregunta expuesta es: donde nos llevará este nuevo concepto en términos del futuro de la curtición? From leather science, a deeper understanding of the La respuesta es: a un desplazamiento paradigmático. theoretical basis of the tanning mechanism has unified the inorganic and organic chemistries of Curtición al cromo permanecerá con nosotros, pero leather making processes. The 'link-lock' mechanism en un futuro se visualizará muy diferentemente provides an explanation of present reactions and a su tecnología por hoy percibida. Opciones para la tool for future developments. transformación del proceso ya sí se pueden proponer. Es importante en este ejercicio cuestionar detalladamente The question now posed is: where does this new los aspectos convencionalmente aceptados de thinking take us, in terms of the future of tanning? esta reacción. The answer is: into a paradigm shift. Tecnologías alternativas de curtición en la era Chrome tanning will remain with us, but in the moderna pueden ahora ser desarrolladas, para future it can be viewed very differently from its producir cueros altamente estables hidrotérmicamente. currently perceived technology. Options for Aquí la teoría eslabón-cerrojo ha demostrado que tales transforming the process may now be proposed. resultados no son obtenibles con un solo reactivo, por lo Important in this exercise is to question closely the menos dos componentes de curtido son requeridos. conventionally accepted features of the reaction. Más aun, la curtición podrá ser más acertadamente formulada para que encaje con la química (o bioquímica) Alternative technologies for tanning in the modern de la reacción según su rendimiento y los requerimientos era can now be developed, to make high hydrothermal del impacto ambiental del cuero. stability leathers. Here, the link-lock theory has demonstrated that such outcomes cannot be achieved INTRODUCTION by any single conventional reagent; at least two tanning components are needed. Moreover, tanning In this paper, the principles of tanning science are applied to can be more accurately formulated to match the current tanning technologies, to assess the opportunities for chemistry (or biochemistry) of the reaction to the positive change and the options for development. Hence the performance and environmental impact requirements title: of the leather. Where is chromium (or other tanning technologies, for that matter) going? RESUMEN In the field of tanning science, the starting point is the 1 De la ciencia del cuero, un entendimiento más recently developed theory of tanning: 'link-lock'. Here, the profundo ha surgido acerca de la base teórica del outcome of any tanning reaction can be rationalised in terms of mecanismo de curtición que ha unificado las químicas the number of components in the overall process and the orgánicas e inorgánicas de los procesos de fabricación nature of relationships between the components and the del cuero. El mecanismo de 'eslabón-cerrojo' provee substrate, collagen. una explicación de las reacciones hoy conocidas y una herramienta para futuros desarrollos. The 'link' part of the reaction concerns the primary reactant, the main component that reacts directly with the collagen. All * A Technical Note based on a presentation at the XXIX IULTCS Congress and103rd annual meeting of the American Leather Chemists Association at the JW Marriott Hotel, Washington, DC, on June 22, 2007 ** Corresponding author - E-mail: [email protected] Manuscript received June 14, 2007, accepted for publication July 16, 2007 JALCA, VOL. 103, 2008 8 THE FUTURE DIRECTIONS OF TANNING tanning reactions exhibit this part of the mechanism, which may involve any or all types of reaction: hydrogen bonding, hydrophobic bonding, electrostatic interaction and covalent bonding. The effects are twofold. oFirst, the structure of the supramolecular water2 around the triple helices is modified, thereby changing the ability of the protein to spread into the interstices between the triple helices, when the helical structure begins to unravel as it denatures under hydrothermal conditions. All primary reactions produce the same outcome, with only a small variation: the observed shrinkage temperature of single component tannages is typically 75-85ºC, although some may confer even less stability because of the nature of the chemical change. The actual value achieved depends on the effect of the reaction on the entropy of activation3, which controls the rate of shrinking, reflected by the conventionally measured shrinkage temperature. Part of Figure 1: The tanning chemistry of oxazolidine: N-methyl derivatives. the modification is the nature of the primary interaction: the weaker the interaction, the lower the hydrothermal TABLE I stability, but the upper limit to the hydrothermal stability is defined by the strongest interaction, covalent bonding. Contributions to the hydrothermal The degree of structure or additional bonding introduced stability of semi alum leather.8 by the tanning reaction has only a second order effect on the hydrothermal stability: regardless of the type of Reaction Ts (ºC) ∆Ts (ºC) structure imposed by this reaction, the hydrothermal none 65 - stability is limited. Al(III) tanning 75 10 oSecond, the presence of the tanning agent modifies the Tara 80 15 shrinking reaction. The ease with which the triple helix Tara + Al(III) 115 50 can unravel into the region between triple helices depends on the resistance offered by the intervening chemical reaction occurs with the carboxyl's of the collagen and not species. The mechanism of the shrinking reaction is with the phenolic hydroxyls.5 Therefore, the characteristics independent of the chemistry of tanning1, so the effect of of the outcomes of the reactions are individual, rather the single tanning species is to hinder the outcome of than combined. unravelling. This view is consistent with the observation o The second reagent may interact with the first, but still that any tanning reaction from a single component, which have no effect on the outcome of the combined process. can only cause the linking effect, will confer the same For example, in the combined tanning effect of metal, such moderate hydrothermal stability increase. Qualitatively, as aluminium(III) and hydrolysable vegetable tannin, it is the effect of the primary reactant is to interfere with the known that the semi metal reaction is dependent on the unravelling process, as the collagen converts from the polyphenol being applied to the collagen first, followed by helical structure into the random coil structure. Hence the the aluminium salt, see below. However, if the polyphenol similarity of outcome. In addition, the interaction is applied after the metal salt, this will result in complexation between the tanning species and the supramolecular water of the metal by the polyphenol, but the outcome is modifies the shrinking process, giving rise to the observed characteristic of independent reactions.6 small variations in the moderate hydrothermal stability resulting from the single component reaction. The o The second reagent may react with the first reagent, outcome of the linking step is independent of the ability of creating a new tanning reaction; in other words the the tanning agent to crosslink. From the work of Das interaction is synergistic. This refers to the situation when Gupta4, mono-functional oxazolidine and bi-functional the observed effect on the hydrothermal stability is greater oxazolidine confer the same shrinkage temperature, about than the sum of the contributions: 80ºC, see Fig. 1. ∆Ts obs > ∆Ts 1 + ∆Ts 2 The 'lock' part of the mechanism refers to the action of a second component in the tannage. The second reaction can where ∆Ts refers to the effect (rise) in shrinkage temperature take several forms, as follows. conferred by the tannage. Note, if the sides of the equation are o The second tanning reaction may be independent of the equal, the effects of the tanning reactions are independent and first tanning reaction. For example, in chromium(III) additive (to some extent), as described above. If the observed retanning after vegetable tanning, regardless of the polyphenol shrinkage temperature change is less than the sum of the type, hydrolysable or condensed, the chromium(III) fixation contributions, the reactions are antagonistic ie one interferes with JALCA, VOL. 103, 2008 THE FUTURE DIRECTIONS OF TANNING 9 the other, to decrease its effect. An example is the combination of hydrolysable vegetable tannin and aldehyde: the available sites on the gallic acid or ellagic acid moieties are unreactive to aldehydic attack and reaction, so the aldehydic reaction with collagen inhibits reaction between the polyphenol and the protein.7 Known cases of high hydrothermal stability exhibit positive interaction, which can be illustrated using the semi alum process, shown in Table I, in which the polyphenol is tara, a hydrolysable gallotannin. Figure 2: Interactions between collagen and aluminium. 11 The difference between the observed shrinkage temperature and high levels of vegetable tannin, hydrolysable or condensed. It the calculated sum of the contributions (here, 50 - (10 + 15) = 25) can be further postulated that there must be some of this structural is indicative of the magnitude of the effect in creating a new water remaining in
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