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Erschienen in: Cellulose 1/2011

01.02.2011

Protonation behavior of 6-deoxy-6-(2-aminoethyl)amino cellulose: a potentiometric titration study

verfasst von: Lidija Fras Zemljič, Duško Čakara, Nico Michaelis, Thomas Heinze, Karin Stana Kleinschek

Erschienen in: Cellulose | Ausgabe 1/2011

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Abstract

The protonation behavior of 6-deoxy-6-(2-aminoethyl)amino cellulose as a novel soluble aminated derivate of cellulose was studied by means of the potentiometric titration technique. The resulting proton binding isotherms exhibit two equivalent steps, which can be described by the standard macroscopic two-pK model, in which the degree of protonation is averaged over all the amine groups. In addition, a microscopic proton binding model was applied, in which the protonation sites are distinguished and the protonation free energy is expanded into an intrinsic term and an electrostatic repulsion between the primary and secondary amine groups. The protonation behavior of 6-deoxy-6-(2-aminoethyl)amino cellulose was compared with a model compound (N-methylethylenediamine).

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Literatur
Zurück zum Zitat Aksberg R, Ödberg L (1990) Adsorption of an anionic polyacrylamide on cellulosic fibers with pre-adsorbed cationic polyelectrolytes. Nord Pulp and Paper Res J 411990:168–171CrossRef Aksberg R, Ödberg L (1990) Adsorption of an anionic polyacrylamide on cellulosic fibers with pre-adsorbed cationic polyelectrolytes. Nord Pulp and Paper Res J 411990:168–171CrossRef
Zurück zum Zitat Avci D, Nuri M, Dagusan L (2002) New cationic polyelectrolytes for flocculation processes of baker’s yeast waste water. Polym Bull 48(4–5):353–359CrossRef Avci D, Nuri M, Dagusan L (2002) New cationic polyelectrolytes for flocculation processes of baker’s yeast waste water. Polym Bull 48(4–5):353–359CrossRef
Zurück zum Zitat Baumann H, Keller B, Ruzicka E (1991) Partially cationized cellulose for non-thrombogenic membrane in the presence of heparin and endothelial-cell-surface-heparansulfate (ES-HS). J Membrane Sci 61:253–268CrossRef Baumann H, Keller B, Ruzicka E (1991) Partially cationized cellulose for non-thrombogenic membrane in the presence of heparin and endothelial-cell-surface-heparansulfate (ES-HS). J Membrane Sci 61:253–268CrossRef
Zurück zum Zitat Berger J, Reist M, Mayer JM, Felt O, Peppas NA, Gurny R (2004) Structure and interactions in covalently and ionically crosslinked chitosan hydrogels for biomedical applications. Eur J Pharm Biopharm 57:19–34CrossRef Berger J, Reist M, Mayer JM, Felt O, Peppas NA, Gurny R (2004) Structure and interactions in covalently and ionically crosslinked chitosan hydrogels for biomedical applications. Eur J Pharm Biopharm 57:19–34CrossRef
Zurück zum Zitat Berlin P, Klemm D, Jung A, Liebegott H, Rieseler R, Tiller J (2003) Film-forming aminocellulose derivatives as enzyme-compatible support matrices for biosensor developments. Cellulose 10:343–367CrossRef Berlin P, Klemm D, Jung A, Liebegott H, Rieseler R, Tiller J (2003) Film-forming aminocellulose derivatives as enzyme-compatible support matrices for biosensor developments. Cellulose 10:343–367CrossRef
Zurück zum Zitat Berscht PC, Nies B, Liebendorfer A, Kreuter J (1994) Incorporation of basic fibroblast growth factor into methylpyrrolidinone chitosan fleeces and determination of the in vitro release characteristics. Biomaterials 15:593–600CrossRef Berscht PC, Nies B, Liebendorfer A, Kreuter J (1994) Incorporation of basic fibroblast growth factor into methylpyrrolidinone chitosan fleeces and determination of the in vitro release characteristics. Biomaterials 15:593–600CrossRef
Zurück zum Zitat Borkovec M, Koper GJM (1994) Ising models of polyprotic acids and bases. J Phys Chem 98:6038–6045CrossRef Borkovec M, Koper GJM (1994) Ising models of polyprotic acids and bases. J Phys Chem 98:6038–6045CrossRef
Zurück zum Zitat Borkovec M, Jönsson B, Koper GJM (2001) Ionization processes and proton binding in polyprotic systems: small molecules, proteins, interfaces and polyelectrolytes. In: Matijević E (ed) Prog Coll Pol Sci 16:99–339 Borkovec M, Jönsson B, Koper GJM (2001) Ionization processes and proton binding in polyprotic systems: small molecules, proteins, interfaces and polyelectrolytes. In: Matijević E (ed) Prog Coll Pol Sci 16:99–339
Zurück zum Zitat Borkovec M, Koper GJM, Piguet C (2006) Ion binding to polyelectrolytes. Curr Opin Colloid Interface Sci 11(5):280–289CrossRef Borkovec M, Koper GJM, Piguet C (2006) Ion binding to polyelectrolytes. Curr Opin Colloid Interface Sci 11(5):280–289CrossRef
Zurück zum Zitat Čakara D, Fras L, Bračič M, Stana Kleinschek K (2009) Protonation behaviour of cotton fabric with irreversibly adsorbed chitosan: a potentiometric titration study. Carbohyd Polym 78:36–40CrossRef Čakara D, Fras L, Bračič M, Stana Kleinschek K (2009) Protonation behaviour of cotton fabric with irreversibly adsorbed chitosan: a potentiometric titration study. Carbohyd Polym 78:36–40CrossRef
Zurück zum Zitat Culler MD, Bitman J, Thompson MJ, Robbins WE, Dutky SR (1979) Mastitis: I. In vitro antimicrobial activity of alkyl amines against mastitic bacteria. J Dairy Sci 62:584–595CrossRef Culler MD, Bitman J, Thompson MJ, Robbins WE, Dutky SR (1979) Mastitis: I. In vitro antimicrobial activity of alkyl amines against mastitic bacteria. J Dairy Sci 62:584–595CrossRef
Zurück zum Zitat Czaja W, Krystynowicz A, Bielecki Sand Brown RM (2006) Microbial cellulose. The natural power to heal wounds. Biomaterials 27(2):145–151CrossRef Czaja W, Krystynowicz A, Bielecki Sand Brown RM (2006) Microbial cellulose. The natural power to heal wounds. Biomaterials 27(2):145–151CrossRef
Zurück zum Zitat Dobrynin AV, Rubinstein M (1999) Hydrophobic polyelectrolytes. Macromolecules 32(3):915–922CrossRef Dobrynin AV, Rubinstein M (1999) Hydrophobic polyelectrolytes. Macromolecules 32(3):915–922CrossRef
Zurück zum Zitat Dobrynin AV, Rubinstein M (2005) Theory of polyelectrolytes in solutions and at surfaces. Prog Poly Sci 30(11):1049–1118CrossRef Dobrynin AV, Rubinstein M (2005) Theory of polyelectrolytes in solutions and at surfaces. Prog Poly Sci 30(11):1049–1118CrossRef
Zurück zum Zitat Dumitriu S (2002) Polymeric biomaterials, 2nd edn (revised and expanded). Marcel Dekker, Inc., New York, pp 1–213 Dumitriu S (2002) Polymeric biomaterials, 2nd edn (revised and expanded). Marcel Dekker, Inc., New York, pp 1–213
Zurück zum Zitat Gärdlund L, Norgren M, Wägberg L, Marklund A (2007) The use of polyelectrolyte complexes (PEC) as strength additives for different pulps used for production of fine paper. Nord Pulp Paper Res 22(2):210–216CrossRef Gärdlund L, Norgren M, Wägberg L, Marklund A (2007) The use of polyelectrolyte complexes (PEC) as strength additives for different pulps used for production of fine paper. Nord Pulp Paper Res 22(2):210–216CrossRef
Zurück zum Zitat Goyal S, Dhull SK, Kapoor KK (2005) Chemical and biological changes during composting of different organic wastes and assessment of composting maturity. Bioresour Technol 96:1584–1591CrossRef Goyal S, Dhull SK, Kapoor KK (2005) Chemical and biological changes during composting of different organic wastes and assessment of composting maturity. Bioresour Technol 96:1584–1591CrossRef
Zurück zum Zitat Hashem A, Shishtawy RME (2001) Preparation and characterization of cationized cellulose for the removal of anionic dyes. Adsorpt Sci Technol 19:197–210CrossRef Hashem A, Shishtawy RME (2001) Preparation and characterization of cationized cellulose for the removal of anionic dyes. Adsorpt Sci Technol 19:197–210CrossRef
Zurück zum Zitat Hattori K, Yoshida T, Nakashima H, Premanathan M, Aragaki R, Mimura T, Kaneko Y, Yamamo N, Uryu T (1998) Synthesis of sulfonated amino polysaccharides having anti-HIV and blood anticoagulant activities. Carbohyd Res 312:1–8CrossRef Hattori K, Yoshida T, Nakashima H, Premanathan M, Aragaki R, Mimura T, Kaneko Y, Yamamo N, Uryu T (1998) Synthesis of sulfonated amino polysaccharides having anti-HIV and blood anticoagulant activities. Carbohyd Res 312:1–8CrossRef
Zurück zum Zitat Hebeish A, Hashem M, EL-Hosamy M, Abass S (2006) Cationization of linen fabric: studying the process parameters. RJTA 10(1):73–88 Hebeish A, Hashem M, EL-Hosamy M, Abass S (2006) Cationization of linen fabric: studying the process parameters. RJTA 10(1):73–88
Zurück zum Zitat Hoenich N (2006) Cellulose for medical applications: past, present, and future. BioResources 1(2):270–280 Hoenich N (2006) Cellulose for medical applications: past, present, and future. BioResources 1(2):270–280
Zurück zum Zitat Holm C, Joanny JF, Kremer K, Netz RR, Reineker P, Seidel C, Vilgis TA, Winkler RG (2004) Polyelectrolyte theory. In: Polyelectrolytes with defined molecular architecture II, vol 166. Springer, Berlin, pp 67–111 Holm C, Joanny JF, Kremer K, Netz RR, Reineker P, Seidel C, Vilgis TA, Winkler RG (2004) Polyelectrolyte theory. In: Polyelectrolytes with defined molecular architecture II, vol 166. Springer, Berlin, pp 67–111
Zurück zum Zitat Jung A, Berlin P (2005) New water-soluble and film-forming aminocellulose tosylates as enzyme support matrices with Cu2+-chelating properties. Cellulose 12:67–84CrossRef Jung A, Berlin P (2005) New water-soluble and film-forming aminocellulose tosylates as enzyme support matrices with Cu2+-chelating properties. Cellulose 12:67–84CrossRef
Zurück zum Zitat Kaputskii FN, Gert EV, Torgashov VI, Zubets OV (2005) Hydrogels for medical applications fabricated by oxidative-hydrolytic modification of cellulose. Fibre Chem 37:485–489CrossRef Kaputskii FN, Gert EV, Torgashov VI, Zubets OV (2005) Hydrogels for medical applications fabricated by oxidative-hydrolytic modification of cellulose. Fibre Chem 37:485–489CrossRef
Zurück zum Zitat Katchalsky A, Mazur J, Spitnik P (1957) Section II: polybase properties of polyvinylamine. J Polym Sci 23(104):513–532CrossRef Katchalsky A, Mazur J, Spitnik P (1957) Section II: polybase properties of polyvinylamine. J Polym Sci 23(104):513–532CrossRef
Zurück zum Zitat Koper GJM, van Genderen MHP, Elissen Roman C, Baars M, Meijer EW, Borkovec M (1997) Protonation mechanism of poly(propylene imine) dendrimers and some associated oligo amines. J Am Chem Soc 119(28):6512–6521CrossRef Koper GJM, van Genderen MHP, Elissen Roman C, Baars M, Meijer EW, Borkovec M (1997) Protonation mechanism of poly(propylene imine) dendrimers and some associated oligo amines. J Am Chem Soc 119(28):6512–6521CrossRef
Zurück zum Zitat Koper GJM, van Duijvenbode RC, Stam D, Steuerle U, Borkovec A (2003) Synthesis and protonation behavior of comblike poly(ethyleneimine). Macromolecules 36(7):2500–2507CrossRef Koper GJM, van Duijvenbode RC, Stam D, Steuerle U, Borkovec A (2003) Synthesis and protonation behavior of comblike poly(ethyleneimine). Macromolecules 36(7):2500–2507CrossRef
Zurück zum Zitat Li H, Du Y, Xu Y (2004) Adsorption and complexation of chitosan wet-end additives in papermaking systems. J Appl Polym Sci 91:2642–2648CrossRef Li H, Du Y, Xu Y (2004) Adsorption and complexation of chitosan wet-end additives in papermaking systems. J Appl Polym Sci 91:2642–2648CrossRef
Zurück zum Zitat Liesene J (2009) Synthesis of water-soluble cationic cellulose derivatives with tertiary amino groups. Cellulose 17:167–172CrossRef Liesene J (2009) Synthesis of water-soluble cationic cellulose derivatives with tertiary amino groups. Cellulose 17:167–172CrossRef
Zurück zum Zitat Lim SH, Hudson SM (2004) Synthesis and antimicrobial activity of a water-soluble chitosan derivative with a fiber-reactive group. Carbohyd Res 339(2):313–319CrossRef Lim SH, Hudson SM (2004) Synthesis and antimicrobial activity of a water-soluble chitosan derivative with a fiber-reactive group. Carbohyd Res 339(2):313–319CrossRef
Zurück zum Zitat Manning GS (1981) Limiting laws and counterion condensation in polyelectrolyte solutions. 6. Theory of the titration curve. J Phys Chem US 85(7):870–877CrossRef Manning GS (1981) Limiting laws and counterion condensation in polyelectrolyte solutions. 6. Theory of the titration curve. J Phys Chem US 85(7):870–877CrossRef
Zurück zum Zitat Marcus RA (1954) Titration of polyelectrolytes at higher ionic strengths. J Phys Chem US 58(8):621–623CrossRef Marcus RA (1954) Titration of polyelectrolytes at higher ionic strengths. J Phys Chem US 58(8):621–623CrossRef
Zurück zum Zitat Mesquita JP, Donnici LC, Pereira FV (2010) Biobased nanocomposites from layer by-layer assembly of cellulose nanowhiskers with chitosan. Biomacromolecules 11:473–480CrossRef Mesquita JP, Donnici LC, Pereira FV (2010) Biobased nanocomposites from layer by-layer assembly of cellulose nanowhiskers with chitosan. Biomacromolecules 11:473–480CrossRef
Zurück zum Zitat Montplaisir D, Daneault C, Chabot B (2008) Surface composition of grafted thermomechanical pulp through XPS measurements. BioResources 3(4):1118–1129 Montplaisir D, Daneault C, Chabot B (2008) Surface composition of grafted thermomechanical pulp through XPS measurements. BioResources 3(4):1118–1129
Zurück zum Zitat Muzzarelli RAA (2009) Chitins and chitosan for the repair of wound skin, nerve, cartilage and bone. Carbohyd Polym 76:167–182CrossRef Muzzarelli RAA (2009) Chitins and chitosan for the repair of wound skin, nerve, cartilage and bone. Carbohyd Polym 76:167–182CrossRef
Zurück zum Zitat Muzzarelli RAA, Mattioli-Belmonte M, Tietz C, Biagini R, Ferioli G, Brunelli MA, Fini M, Giardino R, Ilari P, Biagini G (1994) Stimulatory effect on bone formation exerted by a modified chitosan. Biomaterials 15:1075–1081CrossRef Muzzarelli RAA, Mattioli-Belmonte M, Tietz C, Biagini R, Ferioli G, Brunelli MA, Fini M, Giardino R, Ilari P, Biagini G (1994) Stimulatory effect on bone formation exerted by a modified chitosan. Biomaterials 15:1075–1081CrossRef
Zurück zum Zitat Myllytie P, Salmi J, Laine J (2009) The influence of pH on the adsorption and interaction of chitosan with cellulose. BioResources 4(4):1647–1662 Myllytie P, Salmi J, Laine J (2009) The influence of pH on the adsorption and interaction of chitosan with cellulose. BioResources 4(4):1647–1662
Zurück zum Zitat Packham RF (2007) The laboratory evaluation of polyelectrolyte flocculants. Brit Polym J 4(4):305–315CrossRef Packham RF (2007) The laboratory evaluation of polyelectrolyte flocculants. Brit Polym J 4(4):305–315CrossRef
Zurück zum Zitat Pecse A, Jordane AA, Carluci G, Cintio A (2005) Articles comprising caionic polysaccharides and acidic pH buffering means. US Patent Application Publication:0124799 A1 Pecse A, Jordane AA, Carluci G, Cintio A (2005) Articles comprising caionic polysaccharides and acidic pH buffering means. US Patent Application Publication:0124799 A1
Zurück zum Zitat Ravi Kumar MNV (2000) A review of chitin and chitosan applications. React Funct Polym 46:1–27CrossRef Ravi Kumar MNV (2000) A review of chitin and chitosan applications. React Funct Polym 46:1–27CrossRef
Zurück zum Zitat Rodríguez R, Alvarez-Lorenzo C, Concheiro A (2003) A Cationic cellulose hydrogels: kinetics of the cross-linking process and characterization as pH-/ion-sensitive drug delivery systems. J Control Release 86(2–3):253–265CrossRef Rodríguez R, Alvarez-Lorenzo C, Concheiro A (2003) A Cationic cellulose hydrogels: kinetics of the cross-linking process and characterization as pH-/ion-sensitive drug delivery systems. J Control Release 86(2–3):253–265CrossRef
Zurück zum Zitat Smith RM, Martell AE (1989) Critical stability constants, vol 6. Plenum Press, New York Smith RM, Martell AE (1989) Critical stability constants, vol 6. Plenum Press, New York
Zurück zum Zitat Swerin A, Wägberg L (1994) Size exclusion chromatography for characterisation of cationic polyelectrolytes used in papermaking. Nordic Pulp Paper Res J 411994:18–26CrossRef Swerin A, Wägberg L (1994) Size exclusion chromatography for characterisation of cationic polyelectrolytes used in papermaking. Nordic Pulp Paper Res J 411994:18–26CrossRef
Zurück zum Zitat Swerin A, Odberg L, Lindström T (1990) Deswelling of hardwood kraft pulp fibres by cationic polymers. Nordic Pulp Paper Res J 411990:188–196CrossRef Swerin A, Odberg L, Lindström T (1990) Deswelling of hardwood kraft pulp fibres by cationic polymers. Nordic Pulp Paper Res J 411990:188–196CrossRef
Zurück zum Zitat Szakacs Z, Kraszni M, Noszal B (2004) Determination of microscopic acid–base parameters from NMR-pH titrations. Anal Bioanal Chem 378(6):1428–1448CrossRef Szakacs Z, Kraszni M, Noszal B (2004) Determination of microscopic acid–base parameters from NMR-pH titrations. Anal Bioanal Chem 378(6):1428–1448CrossRef
Zurück zum Zitat Ulrich S, Laguecir A, Stoll S (2005) Titration of hydrophobic polyelectrolytes using Monte Carlo simulations. J Chem Phys 122(9):094911–094919CrossRef Ulrich S, Laguecir A, Stoll S (2005) Titration of hydrophobic polyelectrolytes using Monte Carlo simulations. J Chem Phys 122(9):094911–094919CrossRef
Zurück zum Zitat Van Duijvenbode RC, Rajanayagam A, Koper GJM, Borkovec M, Paulus W, Steuerle U, Haussling L (1999) Influence of the distance between ionizable groups on the protonation behavior of various hexaamines. Phys Chem Chem Phys 1(24):5649–5652CrossRef Van Duijvenbode RC, Rajanayagam A, Koper GJM, Borkovec M, Paulus W, Steuerle U, Haussling L (1999) Influence of the distance between ionizable groups on the protonation behavior of various hexaamines. Phys Chem Chem Phys 1(24):5649–5652CrossRef
Zurück zum Zitat Wu M, Kuga S (2006) Cationization of cellulose fabrics by polyallyamine binding. J Appl Polym Sci 100:1668–1672CrossRef Wu M, Kuga S (2006) Cationization of cellulose fabrics by polyallyamine binding. J Appl Polym Sci 100:1668–1672CrossRef
Zurück zum Zitat Yang S, Fu S, Li X, Zhore Y, Zhan H (2010) Preparation of salt-sensitive and antibacterial hydrogel based on quaternized cellulose. BioResources 5(2):1114–1125 Yang S, Fu S, Li X, Zhore Y, Zhan H (2010) Preparation of salt-sensitive and antibacterial hydrogel based on quaternized cellulose. BioResources 5(2):1114–1125
Metadaten
Titel
Protonation behavior of 6-deoxy-6-(2-aminoethyl)amino cellulose: a potentiometric titration study
verfasst von
Lidija Fras Zemljič
Duško Čakara
Nico Michaelis
Thomas Heinze
Karin Stana Kleinschek
Publikationsdatum
01.02.2011
Verlag
Springer Netherlands
Erschienen in
Cellulose / Ausgabe 1/2011
Print ISSN: 0969-0239
Elektronische ISSN: 1572-882X
DOI
https://doi.org/10.1007/s10570-010-9467-x

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