Preparation of high performance bio-based benzoxazine resin through a green solvent-free strategy for shape memory application

Sha, Xin-Long; Yuan, Li; Liang, Guozheng; Gu, Aijuan

doi:10.1016/j.polymer.2020.122673

Cited by 39 publications

(34 citation statements)

References 64 publications

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“…To reduce the carbon foot print, exploration of non-petrochemical feedstocks that are obtained naturally or in bio-wastes is actively sought both as solvent or solvent-free reactions [ 84 ]. These include cardanol (C) [ 85 , 86 , 87 , 88 , 89 , 90 ]; guaiacol (G) [ 89 , 91 , 92 ]; eugenol [ 93 , 94 ]; isoeugenol [ 95 ]; vanillin (V) [ 96 , 97 , 98 ]; umbelliferone (U) [ 99 ]; catechol [ 100 ]; cinnamic, ferulic, coumaric [ 101 , 102 ] and phloretic acid [ 101 , 103 , 104 ]; magnolol [ 105 ]; resveratrol [ 106 ]; humic acid (coal origin) [ 107 ]; daidzein [ 108 ]; naringenin [ 109 ]; arbutin-linked phenol [ 110 ]; levulinic acid based diphenolic acid [ 111 , 112 ]; sesamol [ 113 ]; apigenin [ 84 ] and amines such as stearylamine [ 93 ], dopamine [ 114 ], furfuryl amine (fa) [ 95 , 115 ], aminolysed poly(ethylene terephthalate) [ 116 ] and isomannide diamine (ima) [ 89 ], as shown in Figure 3 .…”

Section: Classification Of Benzoxazine Monomersmentioning

confidence: 99%

Review on the Accelerated and Low-Temperature Polymerization of Benzoxazine Resins: Addition Polymerizable Sustainable Polymers

et al. 2021

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Due to their outstanding and versatile properties, polybenzoxazines have quickly occupied a great niche of applications. Developing the ability to polymerize benzoxazine resin at lower temperatures than the current capability is essential in taking advantage of these exceptional properties and remains to be most challenging subject in the field. The current review is classified into several parts to achieve this goal. In this review, fundamentals on the synthesis and evolution of structure, which led to classification of PBz in different generations, are discussed. Classifications of PBzs are defined depending on building block as well as how structure is evolved and property obtained. Progress on the utility of biobased feedstocks from various bio-/waste-mass is also discussed and compared, wherever possible. The second part of review discusses the probable polymerization mechanism proposed for the ring-opening reactions. This is complementary to the third section, where the effect of catalysts/initiators has on triggering polymerization at low temperature is discussed extensively. The role of additional functionalities in influencing the temperature of polymerization is also discussed. There has been a shift in paradigm beyond the lowering of ring-opening polymerization (ROP) temperature and other areas of interest, such as adaptation of molecular functionality with simultaneous improvement of properties.

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Section: Classification Of Benzoxazine Monomersmentioning

confidence: 99%

Review on the Accelerated and Low-Temperature Polymerization of Benzoxazine Resins: Addition Polymerizable Sustainable Polymers

et al. 2021

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“…Due to the cross‐linking reaction involving double bonds in isoeugenol‐based benzoxazine, at the same time, the integration of flexible long chains and rigid groups also endows the resins with shape memory property 165 . Combined with the Schiff base reaction between aldehyde group and polyether amine 166 or copolymerization with epoxidized vegetable oil, 167 vanillin‐based shape memory resins were developed as well. Moreover, with the assistant of Schiff base reaction, Ishida et al 168 designed a bio‐resourced benzoxazine with long chain ethers, which was successfully applied in surfactant agent.…”

Section: Bio‐based Benzoxazine Resinmentioning

confidence: 99%

Recent development on bio‐based thermosetting resins

Liu

Zhang

Shun

et al. 2021

Journal of Polymer Science

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Due to the rapid depletion of crude oil and serious environmental pollution, the synthesis of polymers from renewable resource is becoming more and more important. Up to now, a great variety of biomass and bio-based platform compounds have been taken to prepare the polymers. However, as two representative thermosetting resins, epoxy and benzoxazine resin derived from renewable feedstocks only obtain limited attention compared with the popular bio-based plastics, including PLA, PBAT and PHBV etc. The reason might be that the properties of previously reported thermosetting resins directly obtained from biomass are usually unsatisfied, and their application fields are limited. In this paper, the latest development on the synthesis of highperformance bio-based epoxy and polybenzoxazine resins are reviewed. In addition, to further broaden their applications, the functionalization strategies are also summarized. The objective of this work is to help us fully aware the present situation of bio-based thermosetting resins and then promote their faster development, especially practical application.

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“…Alternatively, another synthetic strategy is to convert mono‐functional benzoxazines into bi‐functional benzoxazines by coupling reaction, but mono‐functional benzoxazines must contain reactive functional groups that facilitate coupling reactions between each pair of mono‐functional benzoxazines and coupling agents. In this way, several bi‐functional benzoxazines were respectively synthesized by amidation reaction of a primary amine‐containing mono‐functional benzoxazine with isophthaloyl dichloride, [13,14] by esterification reaction of a mono‐functional hydroxyl‐containing benzoxazine with terephthaloyl dichloride, [15] by nucleophilic addition−elimination reaction of a mono‐functional hydroxyl‐containing benzoxazine with octafluorocyclopentene, [8] by hydrosilylation of a mono‐functional o ‐allylphenol‐based benzoxazine with 1,1,3,3‐tetramethyldisiloxane, [16] and by imidization reaction of a benzaldehyde‐containing mono‐functional benzoxazine with an amine‐terminated polyether, [17] and a tri‐functional benzoxazine was prepared through isocyanate–hydroxyl reaction of a mono‐functional isocyanate‐containing benzoxazine with glycerol [18] …”

Section: Introductionmentioning

confidence: 99%

“…Recently, a series of bi‐functional benzoxazines with flexible chains were synthesized, and the corresponding polybenzoxazines show thermally induced shape memory effect (SME) [11,16,17,19–21] . Though the SME is not an intrinsic property of these polybenzoxazines, an appropriate combination of a molecular structure and a thermomechanical programming would make them exhibit SME.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Dynamic Mechanical Properties, and Shape Memory Effect of Poly(benzoxazine‐ether‐urethane)s

Wang

et al. 2021

ChemistrySelect

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Two series of poly(benzoxazine‐ether‐urethane)s (PBEUs) are prepared through thermally activated ring‐opening polymerization (ROP) of bi‐functional benzoxazines containing ether‐urethane moieties. The bi‐functional benzoxazines are synthesized through coupling reaction of hydroxyl‐containing mono‐functional monomers based on phenol, o‐allylphenol, o‐cresol, p‐cresol, diglycolamine, and paraformaldehyde with 1,6‐hexamethylene diisocyanate (HDI) and 2,4‐toluene diisocyanate (TDI), respectively. The ROP temperature of each HDI‐based benzoxazine is higher than that of the counterpart based on TDI, and they are in descending order ortho‐, para‐, and unsubstituted phenol for both series. Due to the difference in structure symmetry between the two series monomers, the variation of polymerization rate with temperature of each TDI‐based benzoxazine is different from that of the counterpart based on HDI. The ortho‐ and para‐substituted‐phenol‐based PBEUs show lower glass transition temperatures than that of the phenol‐based counterpart. In the vicinity of the glass transition temperature, the HDI‐based PBEUs exhibit thermally induced one‐way dual‐shape memory effect.

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Preparation of high performance bio-based benzoxazine resin through a green solvent-free strategy for shape memory application

Cited by 39 publications

References 64 publications

Review on the Accelerated and Low-Temperature Polymerization of Benzoxazine Resins: Addition Polymerizable Sustainable Polymers

Review on the Accelerated and Low-Temperature Polymerization of Benzoxazine Resins: Addition Polymerizable Sustainable Polymers

Recent development on bio‐based thermosetting resins

Synthesis, Dynamic Mechanical Properties, and Shape Memory Effect of Poly(benzoxazine‐ether‐urethane)s

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