Efficient synthesis of diallyl esters of the furan series from fructose and preparation of copolymers on their basis

Klushin, Victor A.; Кашпарова, В. П.; Kashparov, I. S.; Chus, Yu. A.; Chizhikova, A. A.; Molodtsova, Tatyana; Smirnova, Nina

doi:10.1007/s11172-019-2456-9

Cited by 4 publications

(8 citation statements)

References 36 publications

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“…The PS/DCF and PMMA/DCF copolymers containing 1-2.5% wt. DCF partially retain their solubility in chlorinated hydrocarbons (chloroform, methylene chloride), similar to FDCA diallyl ether copolymers [13]. When the content of DCF ≥ 2.5% wt.…”

Section: Resultsmentioning

confidence: 83%

“…copolymers have a cross-linked structure and swell to a certain limit, but do not dissolve, therefore, can be used as water absorbers [3,21]. With an increase in the DCF content to 10%, the number of crosslinks in the polymer increases [13], the limiting swelling decreases several times to no more than 200%. It makes them suitable for use as ion-exchange resins [22].…”

Section: Resultsmentioning

confidence: 99%

“…2,5-furandicarboxylic acid (FDCA) was prepared by HMF oxidation [12]. Based on FDCA, a new allyl monomers of diallyl-5,5-oxybis-(methylene)bis[furan-2-carboxylate] (DADF) and diallylfuran-2,5-dicarboxylate (DAF) were synthesized and their radical copolymerization with butyl methacrylate was studied [13].…”

Section: Introductionmentioning

confidence: 99%

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2,5–furandicarboxylic Acid Dicinamil Ether and New Copolymers on Its Basis

Кашпарова¹,

Klushin²,

Andreeva³

et al. 2020

IVKKT

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A method for the synthesis of dicinamyl ester of 2,5-furandicarboxylic acid (DCF) a new unsaturated compound of the furan series and potential monomer for producing copolymers with various vinyl compounds and based on them a new generation of construction and ion-exchange materials has been developed. DCF does not form homopolymers as in bulk as in solution (toluene solvent). However, DCF is actively copolymerized with styrene, methyl methacrylate, methacrylic and acrylic acids to form cross-linked polymers with varying degrees of crosslinking. The copolymerization constants of DCF with all investigated vinyl compounds were determined. The DCF copolymers are enriched with comonomer units for all ratios of the components in the initial reaction mixture. They are statistical, and the comonomer units in the macromolecule are randomly arranged. Copolymers with styrene or methyl methacrylate have higher mechanical strength compared to polystyrene and polymethyl methacrylate. Copolymers containing carboxyl groups and 10-20 % wt. crosslinking agent exhibit good ion-exchange properties with respect to heavy metals. The equilibrium adsorption amount of Cu2+ onto ion-exchange сopolymers (221-234 mg/g) was almost twice as large as that onto Amberlite IRC-748 (120.0 mg/g). Materials with a crosslinking agent content of 2.5-5% wt. form polymer gels with high water absorption. Materials containing 2.5 % wt. crosslinking agent (≥ 1400 % for copolymer DCF /acrylic acid and ≥ 1700 for copolymer DCF/methacrylic acid) are showed maximum swelling. These materials can be recommended as water absorbers.

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Section: Resultsmentioning

confidence: 83%

Section: Resultsmentioning

confidence: 99%

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2,5–furandicarboxylic Acid Dicinamil Ether and New Copolymers on Its Basis

Кашпарова¹,

Klushin²,

Andreeva³

et al. 2020

IVKKT

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“…This effect of crosslinker content may be explained by restrained mobility of the macromolecular chains in tighter gel structures. Another explanation for the lower swelling capacity of highly crosslinked resins (Figure 2 c) is that the increasing crosslink density lowers the average chain lengths between the crosslinks (Figure 2 f), thereby reducing the free spaces between macromolecular chains and interfering with their accessibility to the penetrating water molecules [14d, 32] . It should be noted that AAc/DAF‐1 and AAc/DADF‐1 are partially soluble in water (10–15 %), which can be attributed to the formation of star polymers with DAF or DADF cores and poly(AAc) arms [29] .…”

Section: Resultsmentioning

confidence: 99%

“…Recently, great attention has been given to monomers and polymers produced from bio‐based platform chemicals; for example, 5‐hydroxymethylfurfural (HMF) [24] . However, furan‐based monomers with unsaturated side chains for the use in homo‐ and copolymerizations are rare, and reports on them are few [14d, 25] . Divinyl and diallyl esters derived from 2,5‐dihydroxymethylfuran (DHMF) [26] were shown to produce cyclic polymers, rather than linear or branched.…”

Section: Introductionmentioning

confidence: 99%

New Bio‐Based Furanic Materials Effectively Absorb Metals from Water and Exert Antimicrobial Activity

Klushin

Кашпарова

Chizhikova

et al. 2021

Chemistry A European J

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Development of sustainable bio‐based materials for removal of toxic contaminants from water is a high priority goal. Novel bio‐based binary and ternary copolymers with enhanced ion‐exchange, adsorption and antibacterial properties were obtained by using plant biomass‐derived diallyl esters of furandicarboxylic acid (FDCA) as crosslinking agents and easily available vinyl monomers. The synthesized copolymer materials showed higher sorption capacities for NiII, CoII and CuII compared to the commercial ion‐exchange resins, and they maintained their high metal adsorption capacities for over 10 cycles of regeneration. The synthesized copolymer gels containing 1–5 wt % of the crosslinker showed excellent water absorption capacities. The synthesized copolymers with 1 % crosslinker content showed swelling ratios high enough to also act as moisture absorbents. Synthesized copolymers with crosslinker content of 10 wt % performed as contact‐active antibacterials by inhibiting the growth of Gram‐positive (S. aureus) and Gram‐negative bacteria (E. coli, K. pneumonia) in suspension tests.

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