Bis(cyclic carbonate) based on d-mannitol, d-sorbitol and di(trimethylolpropane) in the synthesis of non-isocyanate poly(carbonate-urethane)s

Mazurek-Budzyńska, Magdalena; Rokicki, Gabriel; Drzewicz, Mateusz; Guńka, Piotr A.; Zachara, Janusz

doi:10.1016/j.eurpolymj.2016.04.021

Cited by 44 publications

(56 citation statements)

References 33 publications

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“…Mazurek-Budzynsky and al. 19 also faced a limited D-sorbitol conversion into Sorb-BisCC when reacted with DMC. These authors proposed a reactional pathway (Fig.…”

Section: Resultsmentioning

confidence: 99%

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From D-sorbitol to five-membered bis(cyclo-carbonate) as a platform molecule for the synthesis of different original biobased chemicals and polymers

Furtwengler

Avérous

2018

Sci Rep

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Bis(cyclo-carbonate) was successfully synthesized from D-sorbitol (Sorb-BisCC) through an environmentally friendly process with dimethyl carbonate (DMC) as a reactant. In agreement with green chemistry principles, solvent free reactions were catalyzed and took place at low temperature. The reaction yield was increased until 50%, with the use of 1.3.5-triazabicyclo[4.4.0]dec-5-ene as catalyst and a continuous DMC feed to limit the side-reactions or the loss of reactant by azeotropic flux with a reactional subsidiary product. The obtained Sorb-BisCC is a remarkable platform molecule which could compete with others polycyclic platform molecules (isosorbide). Sorb-BisCC can be e.g., used to synthesize different chemicals such as short and long polyols, or novel biobased non-isocyanate polyurethanes (NIPU). Two Sorb-BisCC molecules have been coupled to obtain novel cyclic diols with pendant side chains. Polyether polyols were also obtained by anionic ring opening polymerization. According to the synthesis conditions, these synthetized polyether polyols range from partially to highly cross-linked materials. Finally, NIPU were synthesized with short and biobased fatty diamines. These different modifications and synthesis highlight the versatility of the Sorb-BisCC and demonstrated its high potential as building block. Sorb-BisCC can be considered as a platform molecule to open the way to different original and biobased chemical architectures.

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“…Mazurek-Budzynsky and al. 19 also faced a limited D-sorbitol conversion into Sorb-BisCC when reacted with DMC. These authors proposed a reactional pathway (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…Mazurek-Budzynska et al . 19 also reported the synthesis of this molecule working with 10 eq. of DMC toward D-sorbitol in methanol catalyzed by potassium carbonate with a global yield of 40%.…”

Section: Introductionmentioning

confidence: 99%

From D-sorbitol to five-membered bis(cyclo-carbonate) as a platform molecule for the synthesis of different original biobased chemicals and polymers

Furtwengler

Avérous

2018

Sci Rep

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“…The synthesis of 5-membered cyclic carbonate ester of carbohydrates using phosgene or its derivatives was reported as early as in the late 60's [20,21]. Carbonation resulting in the formation of 5-membered cyclic carbonates could also be achieved through exchange reaction between dialkyl carbonates -separately prepared by coupling CO 2 and epoxides-with secondary alcohols of sugars [22,23]. We are reporting here a straightforward synthesis of 5-membered cyclic glycocarbonates directly from CO 2 .…”

Section: Synthesis Of 5-membered Cyclic Glycocarbonates and Of Their mentioning

confidence: 99%

CO2 as versatile carbonation agent of glycosides: Synthesis of 5- and 6-membered cyclic glycocarbonates and investigation of their ring-opening

Pati

Feng

Hadjichristidis

et al. 2018

Journal of CO2 Utilization

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CO 2 as versatile carbonation agent of glycosides: Synthesis of 5-and 6-membered cyclic glycocarbonates and investigation of their ring-opening Item Type Article Authors Pati, Debasis; Feng, Xiaoshuang; Hadjichristidis, Nikos; Gnanou, Yves Citation Pati D, Feng X, Hadjichristidis N, Gnanou Y (2018) CO 2 as versatile carbonation agent of glycosides: Synthesis of 5-and 6membered cyclic glycocarbonates and investigation of their ringopening.

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“…[22][23][24][25][26][27][28][29][30] Mazurek-Budzy nska et al 26 selected sugar alcohols such as D-mannitol, D-sorbitol, and di(trimethylolpropane) to prepare bis(cyclic carbonate)s and used them as monomers to prepare a variety of crosslinked poly(carbonate urethane)s. Kühnel et al 25 [22][23][24][25][26][27][28][29][30] Mazurek-Budzy nska et al 26 selected sugar alcohols such as D-mannitol, D-sorbitol, and di(trimethylolpropane) to prepare bis(cyclic carbonate)s and used them as monomers to prepare a variety of crosslinked poly(carbonate urethane)s. Kühnel et al 25 …”

Section: Introductionmentioning

confidence: 99%

Preparation of five‐membered bis(cyclic carbonate)s at atmospheric pressure for polyhydroxyurethane coatings

Dai

Tang

et al. 2019

J of Applied Polymer Sci

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Cyclic carbonates reacted with diamines or polyamines have been proposed as a greener and safer method to prepare free isocyanate polyurethane coatings. Here, five kinds of bis(cyclic carbonate)s (TDC: toluene bis(cyclic carbonate), MDC: 4,4 0diphenylmethane bis(cyclic carbonate), IPDC: isophorone bis(cyclic carbonate), HMDC: 4,4 0 -methylenebis(cyclohexyl cyclic carbonate), HDC: hexamethylene bis(cyclic carbonate)) were prepared by reacting glycerol carbonate with diisocyanate under atmospheric pressure. Their structures were verified by 1 H-NMR and 13 C-NMR. These difunctional cyclic carbonates were then reacted with several amines to prepare new polyhydroxyurethane (PHU) coatings, and the film properties were tested. It was found that PHUs based on aromatic and alicyclic structures including TDC, MDC, IPDC, and HMDC displayed high hardness but had poor flexibility and impact resistance, whereas PHUs based on aliphatic structures such as HDC exhibited good flexibility and impact resistance and low hardness. When the length of the alkyl groups in the amine curing agents increased, the impact resistance and flexibility of the PHUs increased, but their pencil hardness decreased. PHUs from TDC, MDC, and IPDC had excellent chemical resistance, but the PHUs from HMDC and HDC had less chemical resistance. Some films displayed excellent properties including 4H pencil hardness, 100 cm kg impact resistance, and excellent flexibility. Some PHUs exhibited good thermal stability, with T 5% values all above 242 C.

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Bis(cyclic carbonate) based on d-mannitol, d-sorbitol and di(trimethylolpropane) in the synthesis of non-isocyanate poly(carbonate-urethane)s

Cited by 44 publications

References 33 publications

From D-sorbitol to five-membered bis(cyclo-carbonate) as a platform molecule for the synthesis of different original biobased chemicals and polymers

From D-sorbitol to five-membered bis(cyclo-carbonate) as a platform molecule for the synthesis of different original biobased chemicals and polymers

CO2 as versatile carbonation agent of glycosides: Synthesis of 5- and 6-membered cyclic glycocarbonates and investigation of their ring-opening

Preparation of five‐membered bis(cyclic carbonate)s at atmospheric pressure for polyhydroxyurethane coatings

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