Abstract
Organic pigments are prone to aggregate, resulting in decreasing of their properties. Therefore, pigment dispersants are demanded to have both high adsorption capacity and aggregation inhibiting property for pigment particles. In the present study, the suitability of cellulose nanofibers (CNFs) as a dispersant for quinacridone, a common red–violet organic pigment, was investigated. Quinacridone particles were well adsorbed on the CNFs. Scanning electron microscopy images of the quinacridone–CNF mixtures showed that the quinacridone primary particles were stacked along the cellulose fibers, and the aggregations were inhibited. In addition, the size of the quinacridone particles had an effect on their color. The interactions of quinacridone and cellulose were investigated by Fourier transform infrared (FTIR) and solution-state nuclear magnetic resonance (NMR) spectroscopies. FTIR spectra of the quinacridone–CNF mixtures indicated the intermolecular interactions between quinacridone and cellulose. Because quinacridone and CNFs were insoluble in the NMR solvents, gel-state NMR spectroscopy, which has been used for the whole plant cell wall analysis, was conducted on them. Consequently, whole signals arising from quinacridone and cellulose were enabled to be assigned, and the coupling constant of quinacridone has reported for the first time. The nuclear Overhauser effect spectroscopy (NOESY)-NMR spectrum of the quinacridone–CNF mixture revealed both NH group and aromatic moiety of quinacridone were interacted with glucose unit. The former was considered to be related to hydrogen bonding, and the latter to CH–π interactions. These specific interactions might contribute to achieve the high adsorption capacity of CNFs for quinacridone.
Graphic abstract
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Agbo C, Acheampong C, Liping Z, Li M, Wang D, Shaohai F (2019) Synthesis and application of novel dispersant using a dichlorotriazine azo moiety and Dodecan-1-ol. Prog Org Coat 127:1–7. https://doi.org/10.1016/j.porgcoat.2018.09.031
Balea A, Monte MC, de la Fuente E, Negro C, Blanco Á (2017) Application of cellulose nanofibers to remove water-based flexographic inks from wastewaters. Environ Sci Pollut Res 24:5049–5059. https://doi.org/10.1007/s11356-016-8257-x
Balea A, Monte MC, Fuente E, Sanchez-Salvador JL, Blanco A, Negro C (2019) Cellulose nanofibers and chitosan to remove flexographic inks from wastewaters. Environ Sci Water Res Technol 5:1558–1567. https://doi.org/10.1039/c9ew00434c
Chen P, Liu GJ, Wang Y, Zhang SXA (2016) A stable aggregate system of silyl ether substituted quinacridone and its aggregation-state changes induced by fluoride-ions: inspiration for a dual guaranteed strategy for probe design. RSC Adv 6:25986–25991. https://doi.org/10.1039/c6ra01487a
Colom X, Carrillo F, Nogués F, Garriga P (2003) Structural analysis of photodegraded wood by means of FTIR spectroscopy. Polym Degrad Stab 80:543–549. https://doi.org/10.1016/S0141-3910(03)00051-X
Del Puerto E, Domingo C, Garcia Ramos JV, Sanchez-Cortes S (2014) Adsorption study and detection of the high performance organic pigments quinacridone and 2,9-dimethylquinacridone on Ag nanoparticles by surface-enhanced optical spectroscopy. Langmuir 30:753–761. https://doi.org/10.1021/la403625u
Ding L, Jiang Y, Wang B, Li Y, Mao Z, Xu H, Zhong Y, Zhang L, Sui X (2018a) A waterborne bio-based polymer pigment: colored regenerated cellulose suspension from waste cotton fabrics. Cellulose 25:7369–7379. https://doi.org/10.1007/s10570-018-2068-9
Ding Y, Ye M, Han A, Zang Y (2018b) Preparation and characterization of encapsulated C.I. pigment yellow 12 via ball-milling and mini-emulsion polymerization. Prog Org Coat 117:69–75. https://doi.org/10.1016/j.porgcoat.2018.01.009
Elgammal M, Schneider R, Gradzielski M (2016) Development of self-curable hybrid pigment inks by miniemulsion polymerization for inkjet printing of cotton fabrics. Dye Pigment 133:467–478. https://doi.org/10.1016/j.dyepig.2016.06.033
Hao Z, Iqbal A (1997) Some aspects of organic pigments. Chem Soc Rev 26:203–213. https://doi.org/10.1039/cs9972600203
Holding AJ, Mäkelä V, Tolonen L, Sixta H, Kilpeläinen I, King AWT (2016) Solution-state one- and two- dimensional NMR spectroscopy of high-molecular-weight cellulose. Chemsuschem 9:880–892. https://doi.org/10.1002/cssc.201501511
Hosoya T, Kawamoto H, Saka S (2006) Thermal stabilization of levoglucosan in aromatic substances. Carbohydr Res 341:2293–2297. https://doi.org/10.1016/j.carres.2006.06.014
Isogai A (2015) Structural characterization and modifications of surface-oxidized cellulose nanoiber. J Jpn Pet Inst 58:365–375. https://doi.org/10.1627/jpi.58.365
Iwamoto S, Yamamoto S, Lee SH, Endo T (2014) Solid-state shear pulverization as effective treatment for dispersing lignocellulose nanofibers in polypropylene composites. Cellulose 21:1573–1580. https://doi.org/10.1007/s10570-014-0195-5
Klemm D, Kramer F, Moritz S, Lindström T, Ankerfors M, Gray D, Dorris A (2011) Nanocelluloses: a new family of nature-based materials. Angew Chem Int Ed 50:5438–5466. https://doi.org/10.1002/anie.201001273
Lin F, You Y, Yang X, Jiang X, Lu Q, Wang T, Huang B, Lu B (2017) Microwave-assisted facile synthesis of TEMPO-oxidized cellulose beads with high adsorption capacity for organic dyes. Cellulose 24:5025–5040. https://doi.org/10.1007/s10570-017-1473-9
Mansfield SD, Kim H, Lu F, Ralph J (2012) Whole plant cell wall characterization using solution-state 2D NMR. Nat Protoc 7:1579–1589. https://doi.org/10.1038/nprot.2012.064
Medronho B, Romano A, Miguel MG, Stigsson L, Lindman B (2012) Rationalizing cellulose (in)solubility: reviewing basic physicochemical aspects and role of hydrophobic interactions. Cellulose 19:581–587. https://doi.org/10.1007/s10570-011-9644-6
Miyamoto H, Yuguchi Y, Rein DM, Cohen Y, Ueda K, Yamane C (2016) Structure of cellulose/direct dye complex regenerated from supercritical water. Cellulose 23:2099–2115. https://doi.org/10.1007/s10570-016-0900-7
Nomura T, Kawamoto H, Saka S (2017) Pyrolysis of cellulose in aromatic solvents: reactivity, product yield, and char morphology. J Anal Appl Pyrolysis 126:209–217. https://doi.org/10.1016/j.jaap.2017.06.006
Oh SY, Yoo DI, Shin Y, Kim HC, Kim HY, Chung YS, Park WH, Youk JH (2005) Crystalline structure analysis of cellulose treated with sodium hydroxide and carbon dioxide by means of X-ray diffraction and FTIR spectroscopy. Carbohydr Res 340:2376–2391. https://doi.org/10.1016/j.carres.2005.08.007
Paulus EF, Leusen FJJ, Schmidt MU (2007) Crystal structures of quinacridones. CrystEngComm 9:131–143. https://doi.org/10.1039/b613059c
Saito Y, Endo T, Ando D, Nakatsubo F, Yano H (2018) Influence of drying process on reactivity of cellulose and xylan in acetylation of willow (Salix schwerinii E. L. Wolf) kraft pulp monitored by HSQC-NMR spectroscopy. Cellulose 25:6319–6331. https://doi.org/10.1007/s10570-018-2034-6
Salzillo T, Rivalta A, Castagnetti N, D’Agostino S, Masino M, Grepioni F, Venuti E, Brillante A, Girland A (2019) Spectroscopic identification of quinacridone polymorphs for organic electronics. CrystEngComm 21:3702–3708. https://doi.org/10.1039/c9ce00070d
Sytnyk M, Głowacki ED, Yakunin S, Voss G, Schöfberger W, Kriegner D, Stangl J, Trotta R, Gollner C, Tollabimazraehno S, Romanazzi G, Bozkurt Z, Havlicek M, Sariciftci NS, Heiss W (2014) Hydrogen-bonded organic semiconductor micro- and nanocrystals: from colloidal syntheses to (opto-)electronic devices. J Am Chem Soc 136:16522–16532. https://doi.org/10.1021/ja5073965
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
There are not conflict of interest to declare.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Saito, Y., Iwamoto, S., Hontama, N. et al. Dispersion of quinacridone pigments using cellulose nanofibers promoted by CH–π interactions and hydrogen bonds. Cellulose 27, 3153–3165 (2020). https://doi.org/10.1007/s10570-020-02987-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10570-020-02987-0