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1*, J. KOLAR 2, S. POLANC Abstract the USE OF e-PS, 2005, 2, 13-18 ISSN: 1581-9280 WWW.e-PreservationScience.org www.Morana-rtd.com published by © by M O R A N A RTD d.o.o. FULL PAPER REVIEW THE USE OF HALIDES FOR STABILISATION OF IRON GALL INK CONTAINING PAPER - THE PRO- SHORT COMMUNICATION NOUNCED EFFECT OF CATION 1* 1, 2 2 J. MALEŠIÈ , J. KOLAR M. STRLIÈ , S. POLANC 1 National and University Abstract Library, Leskoškova 12, SI- 1000 Ljubljana, Slovenia It has long been known that transitional metal ions and acids in iron gall inks induce degradation of paper support, thus endan- 2 University of Ljubljana, gering numerous historical materials. Stabilization treatment Faculty of Chemistry and should therefore consist of deacidification and addition of Chemical Technology, antioxidants that could be used for stabilization of all historical Aškerèeva 5, SI-1000 material, regardless to their iron gall ink composition. Ljubljana, Slovenia This contribution discusses the effects of various quaternary *Corresponding author: ammonium and phosphonium halides on iron gall ink corrosion [email protected] of cellulose in alkaline environment. It is demonstrated that the size of the cation affects the extent of stabilization obtained with various quaternary ammonium bromides, with the strongest stabilization achieved with tetrabutylammonium chloride, bro- mide and dodecyltrimethylammonium bromide. An addition of either tetrabutylammonium bromide or chloride did not adverse- ly affect the brightness of paper during accelerated ageing. 1. Introduction The two main processes leading to gradual degradation of cellulose in the presence of iron gall ink have been identified as acid hydroly- sis and oxidation, catalyzed by some transition metal ions present in the ink.1 Acid hydrolysis of cellulose is one of the key factors responsible for the degradation of paper during aging.2,3 A number of deacidification techniques have been developed to reduce the acidity and thus lower the rate of its deterioration. received: 01.05.2005 accepted: 14.07.2005 In addition to acids, iron gall inks contain a substantial amount of different transitional metals capable of entering the so called Fenton key words: cellulose, paper reaction or a related pseudo-Fenton reaction,4,5 where they catalyze ageing, iron gall inks, antioxi- homolytic decomposition of peroxides. During the process hydroxyl dants radicals are formed, which react rapidly with a variety of compo- unds.6 Their importance during autoxidation of cellulose has been recently demonstrated, when a correlation was established between the extent of hydroxyl radical formation and degradation of deacidi- fied model paper during ageing.7 13 www.e-PRESERVATIONScience.org In addition to iron, iron gall ink contains other increased stability of paper at 20 oC by 25-50 1,8 transition metals, most notably copper. times, while KBr and KSCN-treated papers were Compared to iron, copper exhibits a superior cat- stabilized to a limited extent and will last up to 3 alytic activity during Fenton-like reactions. The times longer than the one which was only deacidi- catalytic effects of iron and copper proved to be fied.3 additive.9 Recently, an extensive study of the production of Considering the two cellulose degradation path- oxidizing species in model aqueous systems con- ways- acid hydrolysis and oxidation, a stabilizing taining pseudo-Fenton reaction mixture and vari- treatment for iron gall ink induced decay requires ous halides and a pseudo-halide has been per- an addition of alkalis to combat acid hydrolysis of formed confirming their antioxidant properties in paper and antioxidants to inhibit oxidation. the presence of both transitional metals usually present in iron gall ink, copper25 and iron.26 A variety of antioxidants may be used to interfere with the pathway of oxidative degradation of cel- In the present study, evaluation of various halides lulose. They can be classified into two groups with respect to their stabilizing effect during age- according to the mode of action: those which ing of alkaline paper and paper containing iron interrupt the radical chain reaction, i.e. the “chain gall ink is presented. breaking” antioxidants; and “preventive” ones, which inhibit or retard the formation of free radi- 2. Experimental cals from their unstable precursors, particularly from hydroperoxides.10 2.1 Model paper Phytate (myo-inositol hexaphosphate), a complex- The model paper sample used was purified cotton linters cellulose (Whatman filter paper no. 1; ing agent, which belongs to the “preventive -2 group” of antioxidants has been widely used for 86.0 g m , degree of polymerization (DP): stabilization of iron gall ink corrosion.11 The draw- 2630 ±0.74%. back of complexing agents such as phytate is that 2.2 Model inks they are usually metal-specific. Therefore, we began an extensive survey of antioxidants that Two inks, denoted “Ink 0” and “Ink 70”, were could be used for stabilization of all historical used. Both inks were composed of deionised materials, regardless of the iron gall ink composi- water, 31.4 g L-1 of gum arabic (Fluka, Buchs), tion. A selection of antioxidants has been made 49.2 g L-1 of tannic acid (Riedel de Haen, Seelze) taking into account possible discoloration of the and 0.15 mol L-1 of transitional metal from cop- paper or the ink. Antioxidants should also be sta- per(II) sulphate pentahydrate (Riedel de Haen, ble during the conditions of accelerated ageing Seelze) and iron(II) sulphate heptahydrate (Riedel and reasonably harmless or non-toxic. de Haen, Seelze) in molar ratios Cu(II):Fe(II) ions of 0.0 in Ink 0 or 0.7 in Ink 70. Halides such as iodide, bromide and thiocyanate are well known antioxidants which act as radical 2.3 Sample preparation scavengers. They react with hydroxyl radicals in a wide temperature and pH range.12-14 The rate Whatman filter paper was immersed for a few constants for reaction of hydroxyl radicals with seconds into a solution of the selected ink, dilut- -1 iodide and thiocyanate ions are nearly diffusion ed with a solution of gum arabic (31.4 g L ) in controlled,14 while the relative rate constants for deionised water (1:1 (V/V) ratio for gum arabic reaction of hydroxyl radicals with bromide ions solution for Ink 0 and 4:1 ratio for gum arabic in are more than ten times lower.12-15 In acidic solu- case of Ink 70). Wet samples were then pressed tions, bromide and iodide are also capable of cat- between blotting papers and air-dried. alyzing heterolytic decomposition of peroxi- After 1 day of pre-ageing at 70 °C and 50% RH, des.16-18 the samples were immersed for 1 h into a 0.01 mol L-1 aqueous solutions of Ca(HCO ) and air Potassium iodide has been long recognized as an 3 2 effective stabilization agent during oxygen dried. Antioxidants were added by immersing the bleaching of kraft pulps19 or oxygen pulping.20,21 paper samples for 20 min either in an aqueous or The results presented in the literature demon- a dichloromethane solution of various halides in strate an effective stabilization of paper in alka- concentrations as indicated in Table 1. line environment by the addition of iodide,22,23 2.4 Analytical methodology thiocyanate and bromide.24 While iodide and thio- cyanate induce discoloration of paper, this was Colourimetric measurements of paper samples not observed when sodium bromide was added to were performed with a Minolta CM-3610d diffuse 24 the paper. Addition of potassium iodide to the reflectance spectrophotometer with the specular Whatman paper containing calcium carbonate component excluded. The reflectance was meas- 14 Halides for stabilisation of iron gall inks, e-PS, 2005, 2, 13-18 © by M O R A N A RTD d.o.o. Chemical name Formula Solvent c Solubility (mol L-1) (water) Quaternary ammonium bromides Tetramethylammonium bromide Me NBr H O0.03+ 4 2 Tetraethylammonium bromide Et NBr H O0.03+ 4 2 Tetrapropylammonium bromide Pr NBr H O0.03+ 4 2 Tetrabutylammonium bromide Bu NBr H O0.03 4 2 CH Cl 0.3 + 2 2 Benzyltributylammonium bromide BnBu NBr H O0.03 3 2 CH Cl 0.03 + 2 2 Dodecyltrimethylammonium bromide (C H )Me NBr H O0.03 12 25 3 2 CH Cl 0.3 + 2 2 Tetraoctylammonium bromide (C H ) NBr CH Cl 0.03 - 8 17 4 2 2 Tetraheptylammonium bromide (C H ) NBr CH Cl 0.3 - 7 15 4 2 2 Trimethyloctylammonium bromide Me (C H )NBr CH Cl 0.3 + 3 8 17 2 2 Tetradecylammonium bromide (C H ) NBr CH Cl 0.3 - 10 21 4 2 2 Tetradodecylammonium bromide (C H ) NBr CH Cl 0.3 - 12 25 4 2 2 Quaternary phosphonium bromides Methyltriphenylphosphonium bromide MePh PBr H O0.03+ 3 2 Benzyltriphenylphosphonium bromide BnPh PBr CH Cl 0.03 - 3 2 2 Butyltriphenylphosphonium bromide BuPh PBr CH Cl 0.03 - 3 2 2 Alkali bromide Potassium bromide KBr H O0.03+ 2 Quaternary ammonium chloride Tetrabutylammonium chloride Bu NCl CH Cl 0.3 + 4 2 2 Table 1: Various halides evaluated in the study. Concentration and the solvent used are indicated, as well as their solubility in water (+ soluble and - insoluble). ured relative to Minolta standard. Typical R.S.D. alyst and halide antioxidants demonstrated that was below ±1% (n = 3). the antioxidant activity depend on the size of the cation introduced with the halide. Regardless of Viscometric determinations of the degree of poly- whether Cu(II) or Fe(II) was used, the most pro- merization were performed according to the stan- nounced antioxidant activity was exhibited by the 27 -1 dard procedure, using 1 mol L diethylenedi- quaternary ammonium bromide with the longest aminecupric hydroxide solvent (Carlo Erba) pre- alkyl chain.25,26 pared according to the standard procedure.28 DP was calculated from the intrinsic viscosity meas- 3.1 Effect of aqueous treatments with antioxi- urements using the equation29 DP0.85 = 1.1·[η].
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