Modification of lignin with dodecyl glycidyl ether and chlorosulfonic acid for preparation of anionic surfactant

Chen, Chang-Zhou; Li, Mingfei; Wu, Yuying; Sun, Run‐Cang

doi:10.1039/c4ra01873g

Cited by 31 publications

(20 citation statements)

References 31 publications

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“…In the first step, DETA‐terminated amide chains were branched on the lignin by reacting sebacic acid and lignin with DETA. The fourier transform infrared (FTIR) and X‐ray photoelectron spectroscopy (XPS) spectra of lignin in Figures S1 and S2 in the Supporting Information exhibit that lignin has carboxyl and hydroxyl groups, which agrees with previous report . The carboxyl groups of lignin can react with amine groups of DETA to form amide, which has been confirmed by XPS spectra in Figure S2 in the Supporting Information.…”

Section: Introductionsupporting

confidence: 90%

A Solvent‐Resistant and Biocompatible Self‐Healing Supramolecular Elastomer with Tunable Mechanical Properties

Liu

Zhu

Zhang

2017

Macro Chemistry & Physics

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to achieve self-healing ability under specific environment or external stimulus such as heat or solvent. [10][11][12][13][14] To obtain self-healing ability at room temperature, supramolecular elastomers based on small-molecule system were obtained recently. Leibler and coworkers [15,16] first synthesized a selfhealing elastomer by utilizing vegetable oil fatty acid derivatives with diethylenetriamine (DETA) and urea through a two-step reaction. The obtained material, whose glass transition temperature (T g ) was 28 °C, exhibited rubber-like behavior only if heating over 90 °C or adding 11% w/w dodecane as plasticizer, and showed a spontaneous self-healing ability at room temperature. Montarnal et. al. [17] obtained four different classes of materials by using oligocondensation of 2-aminoethylimidazolidone endcapped mixture of fatty acid with DETA and urea. Bao and co-workers [18] described an elastic nanocomposite material with the ability to rapidly self-heal at room temperature by combining a fatty tri-acid, DETA, and graphene oxide as a macrocrosslinker. Zhang and co-workers [19] obtained supramolecular elastomers through reacting linear carboxyl-terminated polydimethylsiloxane oligomers (PDMS-COOH 2 ) with DETA and urea. Our previous work [20] synthesized a self-healing supramolecular elastomer with small-molecular biological acids. The synthesized materials behaved as rubber at room temperature without additional plasticizers or crosslinkers.However, the small-molecule systems by hydrogen-bond interactions are easier to suffer from low mechanical properties and poor solvent-resistance than macromolecular systems due to the lack of molecular chain entanglement. In order to overcome this problem, hybrid networks containing covalent and hydrogen bonds were developed. These researches used epoxide (diepoxide and tetraepoxide) as manageable crosslinker to enhance mechanical properties and insolubility by controlling stoichiometries and side reactions, [21][22][23] which in turn decreased self-healing behavior. Hence, a supramolecular elastomer with self-healing behavior and solvent-resistance and tunable mechanical properties is desirable.Herein, we design a new reaction system and use sebacic acid and lignin as main raw materials to synthesize a ligninbased supramolecular elastomer (LSE). The synthesis route of Self-Healing ElastomersThe purpose of this work is to demonstrate a new design strategy to produce a self-healing supramolecular elastomer with solvent resistance and biocompatibility and tunable mechanical properties. This aim is successfully achieved by synthesizing a lignin-based supramolecular elastomer (LSE) through branching amide molecular chains on the lignin. The use of lignin effectively reduces the glass transition temperature and the degree of crystallinity of LSEs and generates urea-modified hydrogen bond groups to obtain self-healing capability. The synthesized LSEs behave as rubber and exhibit spontaneous self-healing behavior at room temperature without external stimuli. The mechanical an...

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Section: Introductionsupporting

confidence: 90%

A Solvent‐Resistant and Biocompatible Self‐Healing Supramolecular Elastomer with Tunable Mechanical Properties

Liu

Zhu

Zhang

2017

Macro Chemistry & Physics

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“…The general trend supports the fact that grafting DGE to KL increased the molecular weight of lignin. At a lower DGE/KL ratio, DGE might only attach to the carboxylic‐OH group, given that the reaction between the carboxylic‐OH and glycidyl ether groups occurred first due to the relatively high acidity of carboxylic‐OH groups in lignin . However, at a higher DGE/KL ratio, DGE was also grafted to lignin at the phenolic‐OH reactive site, leading to a reduction in phenolic‐OH group content and an increase in molecular weight.…”

Section: Resultsmentioning

confidence: 99%

“…KL and MKL were modified with DGE as described in the literature . In a 250 mL round‐bottom three‐neck glass flask equipped with a mechanical stirrer, 2 g of lignin was dissolved under vigorous stirring (400 rpm) in 80 mL DMSO.…”

Section: Methodsmentioning

confidence: 99%

Modification of Kraft Lignin with Dodecyl Glycidyl Ether

Alwadani

Fatehi

2019

ChemistryOpen

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Kraft lignin (KL) is extensively produced in industry but is mainly burned as fuel. To broaden its use, KL was grafted with dodecyl glycidyl ether to alter its thermal properties. The reaction of KL with dodecyl glycidyl ether (DGE) was analyzed using nuclear magnetic resonance (NMR), Fourier infrared spectroscopy (FT‐IR) and elemental analysis. Alternatively, KL was methylated to mask its phenolic hydroxy groups to investigate how phenolic hydroxy groups impact the grafting of the alkyl chain of DGE onto lignin (methylated Kraft lignin, MKL). The methylation facilitated the molecular weight enhancement and thermal stability reduction of Kraft lignin via grafting with DGE. The influence of grafting alkyl chains on the structural and thermal properties of KL and MKL was studied using thermogravimetric analysis and differential scanning calorimetry analysis. Our data suggest that, due to their high molecular weights and lower glass transition temperatures, the produced lignin derivatives may be promising feedstocks for composite production.

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“…Lignocellulosic materials containing cellulose, hemicelluloses, and lignin are of great interest. Lignin, which is the most abundant aromatic polymer in nature and is largely present in the cell walls of vascular plants and woody tissues, together with cellulose and hemicelluloses, has attracted much attention recently because of its biodegradability, renewability, and nontoxic. Generally, lignin is cogenerated in the pulp and papermaking industries and biofuel production processes; more than 70 million tons are produced just from papermaking .…”

Section: Introductionmentioning

confidence: 99%

Effect of the maleation of lignosulfonate on the mechanical and thermal properties of lignosulfonate/poly(ε‐caprolactone) blends

Wang

Yang

Zou

2015

J of Applied Polymer Sci

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Maleated lignosulfonate (MLS) produced by esterification with maleic anhydride and unmodified lignosulfonate [in the form of lignosulfonic acid (LS)] were incorporated into poly(e-caprolactone) (PCL) via melt-blending. The obtained MLS/PCL composites and LS/PCL composites were characterized by Fourier transform infrared (FTIR) spectroscopy, differential scanning calorimetry (DSC), thermogravimetric (TG) analysis, and electronic universal testing. The FTIR and DSC results show that the interactions between MLS and PCL were stronger than those between LS and PCL, whereas the TG analysis indicated that the LS/PCL composite was more thermally stable than the MLS/PCL composite. The tensile strength of the MLS/PCL blends remained at about 18 MPa when the MLS content reached 50 wt %; this was about 1.7 times larger than that of the LS/PCL blend. The Young's modulus was also enhanced; this indicated an improvement in the mechanical properties. The results show that the maleation of lignosulfonate was beneficial for enhancing the mechanical properties of these blends.

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Modification of lignin with dodecyl glycidyl ether and chlorosulfonic acid for preparation of anionic surfactant

Abstract: Improving the surface activity of lignin through chemical modification for preparation of anionic surfactant.

Cited by 31 publications

References 31 publications

A Solvent‐Resistant and Biocompatible Self‐Healing Supramolecular Elastomer with Tunable Mechanical Properties

A Solvent‐Resistant and Biocompatible Self‐Healing Supramolecular Elastomer with Tunable Mechanical Properties

Modification of Kraft Lignin with Dodecyl Glycidyl Ether

Effect of the maleation of lignosulfonate on the mechanical and thermal properties of lignosulfonate/poly(ε‐caprolactone) blends

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