Abstract
Seven copolymers of maleic anhydride were hydrolyzed and impregnated into sheets of bleached softwood kraft pulps to enhance market pulp properties. Drying the impregnated pulps at 120 °C for 10 minutes, attached to the fiber surfaces up 0.16 meq of carboxyl groups per gram of dry pulp. Heating the impregnated pulps regenerates succinic anhydride moieties which can then form stable ester linkages with cellulosic hydroxyls. The pH of the impregnation solution is important. Impregnation with solutions at pH 8 gave polymer contents without repulping issues. By contrast, impregnation at pH 4 gave dried pulp sheets that were too strong to enable repulping in a paper mill. Although most of the seven copolymers were fixed to cellulose, poly(ethylene-alt-maleic anhydride) gave the highest density of carboxyl groups. The simplicity of waterborne polymers and mild drying temperatures suggests maleic anhydride copolymer treatment could be implemented in a conventional market pulp mill.
Funding source: Natural Sciences and Engineering Research Council of Canada
Award Identifier / Grant number: CRDPJ 531816-18
Funding statement: We thank the National Sciences and Engineering Research Council of Canada (NSERC CRDPJ 531816-18) and our industrial partners, Solenis Canada and Canfor for funding this project.
Acknowledgments
Drs. Anton Esser and Joel Soucy, BASF are acknowledged for supporting the inception of this project. R. H. Pelton holds the Canada Research Chair in Interfacial Technologies and J. M. Moran-Mirabal holds the Canada Research Chair in Micro- and Nanostructured Materials.
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Conflict of interest: The authors declare no conflicts of interest.
References
Ankerfors, M., Duker, E., Lindstrom, T. (2013) Topo-Chemical Modification of Fibres by Grafting of Carboxymethyl Cellulose in Pilot Scale. Nord. Pulp Pap. Res. J. 28(1):6–14.10.3183/npprj-2013-28-01-p006-014Search in Google Scholar
Barzyk, D., Page, D., Ragauskas, A. (1997a) Acidic Group Topochemistry and Fibre-to-Fibre Specific Bond Strength. J. Pulp Pap. Sci. 23(2):J59–J61.Search in Google Scholar
Barzyk, D., Page, D., Ragauskas, A. (1997b) Carboxylic Acid Groups and Fibre Bonding. In: Proc., The Fundamentals of Papermaking Materials: Transactions of the 11th Fundamental Research Symposium. Cambridge. pp. 893–907.10.15376/frc.1997.2.893Search in Google Scholar
Bianchi, E., Ciferri, A., Parodi, R., Rampone, R., Tealdi, A. (1970) Ethylene-Maleic Anhydride Copolymers and Derivatives. Potentiometric Titrations and Interactions with Polypeptides. J. Phys. Chem. 74(5):1050–1056.10.1021/j100700a014Search in Google Scholar
Chen, D. Z., Yang, C. Q., Qiu, X. Q. (2005) Aqueous Polymerization of Maleic Acid and Cross-Linking of Cotton Cellulose by Poly(Maleic Acid). Ind. Eng. Chem. Res. 44(21):7921–7927.10.1021/ie050651+Search in Google Scholar
Drach, J. E. Wet Strength Resins. US Pat. 4,391,878, 1983.Search in Google Scholar
Dubin, P. L., Strauss, U. P. (1970) Hydrophobic Bonding in Alternating Copolymers of Maleic Acid and Alkyl vinyl Ethers. J. Phys. Chem. 74(14):2842–2847.10.1021/j100708a020Search in Google Scholar
Duker, E., Ankerfors, M., Lindstrom, T., Nordmark, G. G. (2008) The Use of CMC as a Dry Strength Agent – the Interplay between CMC Attachment and Drying. Nord. Pulp Pap. Res. J. 23(1):65–71.10.3183/npprj-2008-23-01-p065-071Search in Google Scholar
Duker, E., Lindstrom, T. (2008) On the Mechanisms Behind the Ability of CMC to Enhance Paper Strength. Nord. Pulp Pap. Res. J. 23(1):57–64.10.3183/npprj-2008-23-01-p057-064Search in Google Scholar
Forsstrom, J., Torgnysdofter, A., Wagberg, L. (2005) Influence of Fibre/Fibre Joint Strength and Fibre Flexibility on the Strength of Papers from Unbleached Kraft Fibres. Nord. Pulp Pap. Res. J. 20(2):186–191.10.3183/npprj-2005-20-02-p186-191Search in Google Scholar
Fras, L., Johansson, L. S., Stenius, P., Laine, L., Stana-Kleinschek, K., Ribitsch, V. (2005) Analysis of the Oxidation of Cellulose Fibres by Titration and Xps. Colloids Surf. A, 260(1-3):101–108.10.1016/j.colsurfa.2005.01.035Search in Google Scholar
Garnier, G., Duskova-Smrckova, M., Vyhnalkova, R., Van De Ven, T. G. M., Revol, J. F. (2000) Association in Solution and Adsorption at an Air-Water Interface of Alternating Copolymers of Maleic Anhydride and Styrene. Langmuir 16(8):3757–3763.10.1021/la991440aSearch in Google Scholar
Gu, X., Yang, C. Q. (1998) FT-IR and Ft-Raman Spectroscopy Study of the Cyclic Anhydride Intermediates for Esterification of Cellulose: I. Formation of Anhydrides without a Catalyst. Res. Chem. Intermed. 24(9):979–996.10.1163/156856798X00672Search in Google Scholar
Jewell, R. A. Carboxylated Cellulosic Fibers. Pat. US 6,471,824 B1, 2002.Search in Google Scholar
Jewell, R. A. Carboxylated Cellulosic Fibrous Web and Method of Making the Same. Pat. US 6,592,717 B 2, 2003a.Search in Google Scholar
Jewell, R. A. Method for Enhancing the Softness of a Fibrous Web. USA Pat. US 6,579,414 B2, 2003b.Search in Google Scholar
Jewell, R. A. Method of Increasing the Wet Strength of a Fibrous Sheet. Pat. US 6,579,415 B2, June 17, 2003c.Search in Google Scholar
Johnson, D. (2010) New Applications for Poly (Ethylene-Alt-Maleic Anhydride). Ph. D. Thesis. Durham University.Search in Google Scholar
Kitaoka, T., Isogai, A., Onabe, F. (1999) Chemical Modification of Pulp Fibers by TEMPO-Mediated Oxidation. Nord. Pulp Pap. Res. J. 14(4):279–284.10.3183/npprj-1999-14-04-p279-284Search in Google Scholar
Laine, J., Lindstrom, T., Bremberg, C., Glad-Nordmark, G. (2003) Studies on Topochemical Modification of Cellulosic Fibres – Part 4. Toposelectivity of Carboxymethylation and Its Effects on the Swelling of Fibres. Nord. Pulp Pap. Res. J. 18(3):316–324.10.3183/npprj-2003-18-03-p316-324Search in Google Scholar
Laine, J., Lindstrom, T., Nordmark, G., Risinger, G. (2002a) Studies on Topochemical Modification of Cellulosic Fibres – Part 3. The Effect of Carboxymethyl Cellulose Attachment on Wet-Strength Development by Alkaline-Curing Polyamide-Amine Epichlorohydrin Resins. Nord. Pulp Pap. Res. J. 17(1):57–60.10.3183/npprj-2002-17-01-p057-060Search in Google Scholar
Laine, J., Lindstrom, T., Nordmark, G. G., Risinger, G. (2000) Studies on Topochemical Modification of Cellulosic Fibres – Part 1. Chemical Conditions for the Attachment of Carboxymethyl Cellulose onto Fibres. Nord. Pulp Pap. Res. J. 15(5):520–526.10.3183/npprj-2000-15-05-p520-526Search in Google Scholar
Laine, J., Lindstrom, T., Nordmark, G. G., Risinger, G. (2002b) Studies on Topochemical Modification of Cellulosic Fibres – Part 2. The Effect of Carboxymethyl Cellulose Attachment on Fibre Swelling and Paper Strength. Nord. Pulp Pap. Res. J. 17(1):50–56.10.3183/npprj-2002-17-01-p050-056Search in Google Scholar
Lee, M. K., Biermann, C. J. (1992) Grafting of Maleic-Anhydride Copolymers onto Cellulose-Acetate and Methyl Cellulose. J. Wood Chem. Technol. 12(2):231–240.10.1080/02773819208545081Search in Google Scholar
Lepoutre, P., Hui, S., Robertson, A. (1973) The Water Absorbency of Hydrolyzed Polyacrylonitrile‐Grafted Cellulose Fibers. J. Appl. Polym. Sci. 17(10):3143–3156.10.1002/app.1973.070171017Search in Google Scholar
Lindstrom, T., Carlsson, G. (1982a) The Effect of Carboxyl Groups and Their Ionic Form During Drying on the Hornification of Cellulose Fibers. Sven. Papp.tidn. Nord. Cellul. 85(15):R146–R151.Search in Google Scholar
Lindstrom, T., Carlsson, G. (1982b) The Effect of Chemical Environment on Fiber Swelling. Sven. Papp.tidn. Nord. Cellul. 85(3):R14–R20.Search in Google Scholar
Musa, O. M. Handbook of Maleic Anhydride Based Materials. Springer, 2016.10.1007/978-3-319-29454-4Search in Google Scholar
Pompe, T., Zschoche, S., Herold, N., Salchert, K., Gouzy, M.-F., Sperling, C., Werner, C. (2003) Maleic Anhydride Copolymers – a Versatile Platform for Molecular Biosurface Engineering. Biomacromolecules 4(4):1072–1079.10.1021/bm034071cSearch in Google Scholar PubMed
Ramos, A., Sousa, S., Evtuguin, D. V., Gamelas, J. a. F. (2017) Functionalized Xylans in the Production of Xylan-Coated Paper Laminates. React. Funct. Polym. 117:89–96.10.1016/j.reactfunctpolym.2017.06.006Search in Google Scholar
Rätzsch, M. (1988) Alternating Maleic Anhydride Copolymers. Prog. Polym. Sci. 13(4):277–337.10.1016/0079-6700(88)90001-9Search in Google Scholar
Saito, T., Isogai, A. (2005) Ion-Exchange Behavior of Carboxylate Groups in Fibrous Cellulose Oxidized by the TEMPO-Mediated System. Carbohydr. Polym. 61(2):183–190.10.1016/j.carbpol.2005.04.009Search in Google Scholar
Saito, T., Isogai, A. (2007) Wet Strength Improvement of TEMPO-Oxidized Cellulose Sheets Prepared with Cationic Polymers. Ind. Eng. Chem. Res. 46(3):773–780.10.1021/ie0611608Search in Google Scholar
Sjostrom, E., Janson, J., Haglund, P., Enstrom, B. (1965) The Acid Groups in Wood and Pulp as Measured by Ion Exchange. J. Polym. Sci., C Polym. Symp.. 11:221–241.10.1002/polc.5070110116Search in Google Scholar
Uhlmann, P., Skorupa, S., Werner, C., Grundke, K. (2005) Characterization of Maleic Acid/Anhydride Copolymer Films by Low-Rate Dynamic Liquid−Fluid Contact Angle Measurements Using Axisymmetric Drop Shape Analysis. Langmuir 21(14):6302–6307.10.1021/la046871uSearch in Google Scholar
Wagberg, L., Bjorklund, M. (1993) On the Mechanism Behind Wet Strength Development in Papers Containing Wet Strength Resins. Nord. Pulp Pap. Res. J. 8:53–58.10.3183/npprj-1993-08-01-p053-058Search in Google Scholar
Wågberg, L., Annergren, G. (1997) Physicochemical Characterization of Papermaking Fibres. In: The fundamentals of papermaking materials, Trans. of the XIth Fund. Res. Symp., Ed. Baker, C. F., Cambridge. pp. 1–82.10.15376/frc.1997.1.1Search in Google Scholar
Wågberg, L., Winter, L., Odberg, L., Lindstrom, T. (1987) On the Charge Stoichiometry Upon Adsorption of a Cationic Polyelectrolyte on Cellulosic Materials. Colloids Surf. 27(1-3):163–173.10.1016/0166-6622(87)80335-9Search in Google Scholar
Westland, J. A. Method and Composition for Increasing the Strength of Compositions Containing High-Bulk Fibers. Pat. US 5,755,828, May 26, 1998.Search in Google Scholar
Westland, J. A., Jewell, R. A., Neogi, A. N. Polymeric Polycarboxylic Acid Crosslinked Cellulose Fibers. Pat. US 5,998,511, 1999.Search in Google Scholar
Westland, J. A., Jewell, R. A., Neogi, A. N. Absorbent Composite Containing Polymaleic Acid Crosslinked Cellulose Fibers. Pat. US 6,184,271 B1, 2001.Search in Google Scholar
Xu, G. G., Yang, C. Q. X. (1999) Comparison of the Kraft Paper Crosslinked by Polymeric Carboxylic Acids of Large and Small Molecular Sizes: Dry and Wet Performance. J. Appl. Polym. Sci. 74(4):907–912.10.1002/(SICI)1097-4628(19991024)74:4<907::AID-APP17>3.0.CO;2-9Search in Google Scholar
Xu, Y. F., Yang, C. Q., Chen, C. M. (1999) Wet Reinforcement of Paper with High-Molecular-Weight Multifunctional Carboxylic Acid. Tappi J. 82(8):150–156.Search in Google Scholar
Yang, C. Q. (1993) Infrared Spectroscopy Studies of the Cyclic Anhydride as the Intermediate for the Ester Crosslinking of Cotton Cellulose by Polycarboxylic Acids. I. Identification of the Cyclic Anhydride Intermediate. J. Polym. Sci., Part A, Polym. Chem. 31(5):1187–1193.10.1002/pola.1993.080310514Search in Google Scholar
Yang, C. Q., Wang, X. (1996a) Formation of Cyclic Anhydride Intermediates and Esterification of Cotton Cellulose by Multifunctional Carboxylic Acids: An Infrared Spectroscopy Study. Tex. Res. J. 66(9):595–603.10.1177/004051759606600908Search in Google Scholar
Yang, C. Q., Wang, X. (1996b) Infrared Spectroscopy Studies of the Cyclic Anhydride as the Intermediate for the Ester Crosslinking of Cotton Cellulose by Polycarboxylic Acids. II. Comparison of Different Polycarboxylic Acids. J. Polym. Sci., Part A, Polym. Chem. 34(8):1573–1580.10.1002/(SICI)1099-0518(199606)34:8<1573::AID-POLA22>3.0.CO;2-4Search in Google Scholar
Yang, C. Q., Xu, Y. (1998) Paper Wet Performance and Ester Crosslinking of Wood Pulp Cellulose by Poly(Carboxylic Acids). J. Appl. Polym. Sci. 67(4):649–658.10.1002/(SICI)1097-4628(19980124)67:4<649::AID-APP8>3.0.CO;2-QSearch in Google Scholar
Yang, C. Q., Xu, Y., Wang, D. (1996) FT-IR Spectroscopy Study of the Polycarboxylic Acids Used for Paper Wet Strength Improvement. Ind. Eng. Chem. Res. 35(11):4037–4042.10.1021/ie960207uSearch in Google Scholar
Supplemental Material
The online version of this article offers supplementary material (https://doi.org/10.1515/npprj-2021-0005).
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Articles in the same Issue
- Frontmatter
- Chemical pulping
- Visualization of multiscale ring formation in a rotary kiln
- Chemical and morphological characterization and pulping of Casuarina equisetifolia
- Effect of polysulfide pulping process on the energy balance of softwood and hardwood kraft pulp mills
- Bleaching
- Assessment of Q(OP)D(PO) bleachability of softwood kraft pulp
- Mechanical pulping
- The effect of process design on refiner pulp quality control performance
- Paper technology
- Carboxylated bleached kraft pulp from maleic anhydride copolymers
- Sustainable coatings on paper for enhancing barrier properties based on hemicellulose
- Coating
- Fold cracking of coated papers: investigation on automated computer-aided visual assessment method
- The effect of paper coatings containing biopolymer binder and different natural pigments on printability
- Nanotechnology
- Adsorption of biopolymers onto nanocelluloses for the fabrication of hollow microcapsules
- Facile fabrication of superhydrophobic filter paper with improved durability and water repellency
- Evaluation of mulberry branch waste as raw material for nanocellulose synthesis: effects of the synthesis method on product properties
- Chemical technology/modifications
- Tailoring the physical characteristics of solution blown cellulosic nonwovens by various post-treatments
- Miscellaneous
- Refining pulp for tensile strength
- Application of sequencing batch biofilm reactor (SBBR) to recycled paper mill effluent treatment
- Bar forces in pulp refiners
Articles in the same Issue
- Frontmatter
- Chemical pulping
- Visualization of multiscale ring formation in a rotary kiln
- Chemical and morphological characterization and pulping of Casuarina equisetifolia
- Effect of polysulfide pulping process on the energy balance of softwood and hardwood kraft pulp mills
- Bleaching
- Assessment of Q(OP)D(PO) bleachability of softwood kraft pulp
- Mechanical pulping
- The effect of process design on refiner pulp quality control performance
- Paper technology
- Carboxylated bleached kraft pulp from maleic anhydride copolymers
- Sustainable coatings on paper for enhancing barrier properties based on hemicellulose
- Coating
- Fold cracking of coated papers: investigation on automated computer-aided visual assessment method
- The effect of paper coatings containing biopolymer binder and different natural pigments on printability
- Nanotechnology
- Adsorption of biopolymers onto nanocelluloses for the fabrication of hollow microcapsules
- Facile fabrication of superhydrophobic filter paper with improved durability and water repellency
- Evaluation of mulberry branch waste as raw material for nanocellulose synthesis: effects of the synthesis method on product properties
- Chemical technology/modifications
- Tailoring the physical characteristics of solution blown cellulosic nonwovens by various post-treatments
- Miscellaneous
- Refining pulp for tensile strength
- Application of sequencing batch biofilm reactor (SBBR) to recycled paper mill effluent treatment
- Bar forces in pulp refiners