Abstract
Aminoalkylalkoxysilane copolymers (co-AAAS) have the ability to simultaneously deacidify and strengthen paper documents. Nevertheless, despite enhancing the tensile strength, they generally fail to improve the folding endurance of the degraded groundwood pulp-rich papers. Focusing on that specific type of papers, several ways to overcome their lack of reinforcement were investigated. Promoting the polymerization of AAAS using catalysts and thermal steps was one of them. A monitoring with FTIR spectroscopy showed that the thermal step was the most efficient in speeding up the hydrolysis and polycondensation of 3-aminopropylmethyldiethoxysilane (AM) monomer in aqueous solutions. The progress of the two-steps reaction in terms of degree of polymerization of AAAS polymers was then studied in-situ after heating the paper, using Cross Polarization—Magic Angle Spinning 29Si solid-state NMR, and was shown to be enhanced as well. The other optimization route explored was to stabilize the paper before treatment. Our previous research had shown that the presence of oxidized groups in paper hampered the strengthening. Sodium borohydride, a known bleaching agent in paper conservation, was used prior to the AAASs treatment to decrease the amount of carbonyls in paper. The reduction and the thermal step were compared in terms of the mechanical properties (folding endurance and tensile strength) upon AAASs treatment of several lignocellulosic papers, including three newsprints dated 1911–1923. The use of sodium borohydride led to a significant improvement of the folding endurance of the samples, an unprecedented result. It enabled at the same time to counteract the yellowing induced by the AAAS and to build a larger alkaline reserve.
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References
Ahn K, Henniges U, Banik G, Potthast A (2012) Is cellulose degradation due to β-elimination processes a threat in mass deacidification of library books? Cellulose 19:1149–1159. https://doi.org/10.1007/s10570-012-9723-3
Ahn K, Rosenau T, Potthast A (2013) The influence of alkaline reserve on the aging behavior of book papers. Cellulose 20:1989–2001. https://doi.org/10.1007/s10570-013-9978-3
Area MC, Cheradame H (2011) Paper aging and degradation: recent findings and research methods. Bio Resour 6:5307–5337. https://doi.org/10.15376/biores.6.4.5307-5337
Banik G, Bruckle I (2011) Paper and water: a guide for conservators, 1st edn. Butterworth-Heinemann, Amsterdam, New York
Bennevault-Celton V, Maciejak O, Desmazières B, Cheradame H (2010) Condensation of alkoxysilanes in alcoholic media: I oligomerization of dimethyldiethoxysilane. Polym Int 59:43–54. https://doi.org/10.1002/pi.2687
Bicchieri M, Brusa P (1997) The bleaching of paper by reduction with the borane tert-butylamine complex. Restaurator 18:1–11. https://doi.org/10.1515/rest.1997.18.1.1
Bicchieri M, Bella M, Semetilli F (1999) A quantitative measure of borane tert-butylamine complex effectiveness in carbonyl reduction of aged papers. Restaurator 20:22–29. https://doi.org/10.1515/rest.1999.20.1.22
Bicchieri M, Sementilli FM, Sodo A (2000) Application of seven borane complexes in paper conservation. Restaurator 21:213–228. https://doi.org/10.1515/REST.2000.213
Brochier Salon M-C, Bayle P-A, Abdelmouleh M et al (2008) Kinetics of hydrolysis and self condensation reactions of silanes by NMR spectroscopy. Colloids Surf A 312:83–91. https://doi.org/10.1016/j.colsurfa.2007.06.028
Brown HC, Murray KJ, Murray LJ et al (1960) Hydroboration. V. A study of convenient new preparative procedures for the hydroboration of olefins. J Am Chem Soc 82:4233–4241. https://doi.org/10.1021/ja01501a030
Brown HC, Snyder C, Rao BCS, Zweifel G (1986) Organoboranes for synthesis. 2. Oxidation of organoboranes with alkaline hydrogen peroxide as a convenient route for the cis-hydration of alkenes via hydroboration. Tetrahedron 42:5505–5510
Browning BL (1977) Analysis of paper, Enlarged 2. M. Dekker, New York
Bruice PY (2009) Essential organic chemistry, 2nd edn. Prentice Hall, Upper Saddle River, N.J.
Burgess HD (1988) Practical considerations for conservation bleaching. JIIC-CG 13:11–26
Calvini P, Gorassini A (2002) FTIR: deconvolution spectra of paper documents. Restaurator 23:48–66. https://doi.org/10.1515/REST.2002.48
Casey JP (1961) Pulp and paper: chemistry and chemical technology III: paper testing and converting, 2nd edn. Interscience Publishers Ltd., New York
Chojnowski J, Cypryk M (2000) Synthesis of linear polysiloxanes. In: Jones RG, Ando W, Chojnowski J (eds) Silicon-containing polymers: the science and technology of their synthesis and applications. Springer, Netherlands, Dordrecht, pp 3–41
Colby MW, Osaka A, Mackenzie JD (1988) Temperature dependence of the gelation of silicon alkoxides. J Non-Cryst Solids 99:129–139. https://doi.org/10.1016/0022-3093(88)90465-6
Daher C, Fabre-Francke I, Balcar N et al (2018) Consolidation of degraded polyurethane foams by means of polysiloxane mixtures: polycondensation study and application treatment. Polym Degrad Stab 158:92–101. https://doi.org/10.1016/j.polymdegradstab.2018.10.029
Dupont A-L, Egasse C, Morin A, Vasseur F (2007) Comprehensive characterisation of cellulose- and lignocellulose-degradation products in aged papers: capillary zone electrophoresis of low-molar mass organic acids, carbohydrates, and aromatic lignin derivatives. Carbohydr Polym 68:1–16. https://doi.org/10.1016/j.carbpol.2006.07.005
Dupont A-L, Lavédrine B, Cheradame H (2010) Mass deacidification and reinforcement of papers and books VI–Study of aminopropylmethyldiethoxysilane treated papers. Polym Degrad Stab 95:2300–2308
Ďurovič M, Zelinger J (1993) Chemical processes in the bleaching of paper in library and archival collections. Restaurator 14:78–101. https://doi.org/10.1515/rest.1993.14.2.78
Ferrandin-Schoffel N, Haouas M, Martineau-Corcos C et al (2020) Modeling the reactivity of aged paper with aminoalkylalkoxysilanes as strengthening and deacidification agents. ACS Appl Polym Mater 2:1943–1953. https://doi.org/10.1021/acsapm.0c00132
Ferrandin-Schoffel N, Martineau-Corcos C, Piovesan C et al (2021) Stability of lignocellulosic papers strengthened and deacidified with aminoalkylalkoxysilanes. Polym Degrad Stab 183:109413. https://doi.org/10.1016/j.polymdegradstab.2020.109413
Fox FJ, Noren RW, Krankkala GE (1978) Catalyst for condensation of hydrolyzable silanes and storage stable compositions thereof. United States Patent 4,101,513
Graminski EL, Parks EJ, Toth EE (1979) The effects of temperature and moisture on the accelerated aging of paper. Durability of macromolecular materials. American Chemical Society, pp 341–355
Havlínová B, Katuščák S, Petrovičová M et al (2009) A study of mechanical properties of papers exposed to various methods of accelerated ageing. Part I. The effect of heat and humidity on original wood-pulp papers. J Cult Herit 10:222–231. https://doi.org/10.1016/j.culher.2008.07.009
Heinze T, El Seoud OA, Koschella A (2018) Structure and properties of cellulose and its derivatives. Cellulose derivatives. Springer International Publishing, Cham, pp 39–172
Hemmingson JA, Morgan KR (1990) ACP/MAS carbon-13 NMR study of photodegraded newsprint. Holzforschung 44:127–131. https://doi.org/10.1515/hfsg.1990.44.2.127
Henniges U, Potthast A (2009) Bleaching revisited: impact of oxidative and reductive bleaching treatments on cellulose and paper. Restaurator 30:294–320. https://doi.org/10.1515/rest.017
Hey M (1977) Paper bleaching: its simple chemistry and working procedures. Pap Conserv 2:10–23. https://doi.org/10.1080/03094227.1977.9638494
Lienardy A, Van Damme P (1988) A bibliographical survey of the bleaching of paper. Restaurator 9:178–198. https://doi.org/10.1515/rest.1988.9.4.178
Massiot D, Fayon F, Capron M et al (2002) Modelling one- and two-dimensional solid-state NMR spectra: modelling 1D and 2D solid-state NMR spectra. Magn Reson Chem 40:70–76. https://doi.org/10.1002/mrc.984
Monredon-Senani S (2004) Interaction organosilanes/silice de précipitation du milieu hydro-alcoolique au milieu aqueux. Thesis, Paris, p 6
Moropoulou A, Zervos S (2003) The immediate impact of aqueous treatments on the strength of paper. Restaurator 24:160–177. https://doi.org/10.1515/REST.2003.160
Müller EMK, Henniges U, Brückle I (2019) Retreatment of a print damaged by excessive sodium borohydride bleaching. Restaur Int J Preserv Libr Arch Mater 40:123–137. https://doi.org/10.1515/res-2019-0001
Pellizzi E, Lattuati-Derieux A, de d’EspinoseLacaillerie J-B et al (2012) Reinforcement properties of 3-aminopropylmethyldiethoxysilane and N-(2-Aminoethyl)-3-aminopropylmethyldimethoxysilane on polyurethane ester foam. Polym Degrad Stab 97:2340–2346. https://doi.org/10.1016/j.polymdegradstab.2012.07.031
Piovesan C, Dupont A-L, Fabre-Francke I et al (2014) Paper strengthening by polyaminoalkylalkoxysilane copolymer networks applied by spray or immersion: a model study. Cellulose 21:705–715. https://doi.org/10.1007/s10570-013-0151-9
Piovesan C, Fabre-Francke I, Dupont A-L et al (2017) The impact of paper constituents on the efficiency of mechanical strengthening by polyaminoalkylalkoxysilanes. Cellulose 24:5671–5684. https://doi.org/10.1007/s10570-017-1513-5
Piovesan C, Fabre-Francke I, Nguyen T-P et al (2018a) Application de traitements à base de polyaminoalkylalcoxysilanes pour la désacidification et le renforcement simultanés de documents anciens sur papier. Support/Tracé 18:106–116
Piovesan C, Fabre-Francke I, Paris-Lacombe S et al (2018b) Strengthening naturally and artificially aged paper using polyaminoalkylalkoxysilane copolymer networks. Cellulose 25:6071–6082. https://doi.org/10.1007/s10570-018-1955-4
Piovesan C (2016) Elaboration de traitements de conservation à base de réseaux de polysiloxanes pour le renforcement et la désacidification simultanés adaptables à différents papiers : exemple des papiers de presse. Cergy-Pontoise
Richardson C, Saunders D (2007) Acceptable light damage: a preliminary investigation. Stud Conserv 52:177–187. https://doi.org/10.1179/sic.2007.52.3.177
Rocha J, Klinowski J (1990) 29Si and 27Al magic-angle-spinning NMR studies of the thermal transformation of kaolinite. Phys Chem Minerals 17:179–186. https://doi.org/10.1007/BF00199671
Sève R (1997) Physique de la couleur: de l’apparence colorée à la technique colorimétrique. Dunod, Paris
Socrates G (2004) Infrared and Raman characteristic group frequencies: tables and charts, 3rd edn. Wiley-Blackwell, Chichester
Souguir Z, Dupont A-L, d’Espinose de Lacaillerie J-B et al (2011) Chemical and physicochemical investigation of an aminoalkylalkoxysilane as strengthening agent for cellulosic materials. Biomacromolecules 12:2082–2091. https://doi.org/10.1021/bm200371u
Souguir Z, Dupont A-L, Fatyeyeva K et al (2012) Strengthening of degraded cellulosic material using a diamine alkylalkoxysilane. RSC Adv 2:7470–7478. https://doi.org/10.1039/c2ra20957h
Tang LC (1986) Stabilization of paper through sodium borohydride treatment. In: historic textile and paper materials, pp 427–441
Torry SA, Campbell A, Cunliffe AV, Tod DA (2006) Kinetic analysis of organosilane hydrolysis and condensation. Int J Adhes Adhes 26:40–49. https://doi.org/10.1016/j.ijadhadh.2005.03.008
Walker ERH (1976) The functional group selectivity of complex hydride reducing agents. Chem Soc Rev 5:23–50. https://doi.org/10.1039/cs9760500023
Whitmore PM, Bogaard J (1994) Determination of the cellulose scission route in the hydrolytic and oxidative degradation of paper. Restaurator 15:26–45. https://doi.org/10.1515/rest.1994.15.1.26
Williams JC (1981) A review of paper quality and paper chemistry. Libr Trends 30(2):203–224
Zhang Z (1997) Catalytic effect of aluminum acetylacetonate on hydrolysis and polymerization of methyltrimethoxysilane. Langmuir 13:473–476. https://doi.org/10.1021/la960771+
Zhang Z, Sakka S (1999) Hydrolysis and polymerization of dimethyldiethoxysilane, methyltrimethoxysilane and tetramethoxysilane in presence of aluminum acetylacetonate. A complex catalyst for the formation of siloxanes. J Sol-Gel Sci Technol 16:209–220. https://doi.org/10.1023/A:1008761002205
Zhang Z, Tanigami Y, Terai R (1995) Catalytic effect of acetylacetonates on gel formation of CH3SiO32. J Non-Cryst Solids 191:304–310. https://doi.org/10.1016/0022-3093(95)00316-9
Acknowledgments
The participation of the Bibliothèque Nationale de France is acknowledged. Sabrina Paris-Lacombe, Camille Piovesan, Alice Gimat and Oulfa Belhadj (CRC) are warmly thanked for their contribution and for fruitful discussions.
Funding
This research was supported by the Paris Seine Graduate School Humanities, Creation, Heritage, Investissements d’Avenir ANR-17-EURE-0021—Foundation for Cultural Heritage Science. Charlotte Martineau-Corcos has received financial support from the Paris Ile-de-France Region—DIM “Respore”.
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NF-S: Conceptualization, Investigation, Validation, Visualization, Writing—original draft. A-LD: Funding acquisition, Project administration, Resources, Conceptualization, Investigation, Supervision, Writing—review and editing. CM-C: Investigation. OF: Funding acquisition, Project administration, Conceptualization, Investigation, Supervision, Writing—review and editing.
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Ferrandin-Schoffel, N., Dupont, AL., Martineau-Corcos, C. et al. Routes to improve the strengthening of paper with aminoalkylalkoxysilanes. Cellulose 30, 539–556 (2023). https://doi.org/10.1007/s10570-022-04906-x
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DOI: https://doi.org/10.1007/s10570-022-04906-x