22590-66-5Relevant articles and documents
Recyclable and Malleable Epoxy Thermoset Bearing Aromatic Imine Bonds
Zhao, Shou,Abu-Omar, Mahdi M.
, (2018)
A method for preparing reprocessable epoxy thermoset is presented. The process is composed of synthesis of a bisphenol monomer bridged by an imine bond, glycidylation of the bisphenol, and cross-linking with a hardener to form thermoset. The resulting epo
Facile: In situ preparation of high-performance epoxy vitrimer from renewable resources and its application in nondestructive recyclable carbon fiber composite
Wang, Sheng,Ma, Songqi,Li, Qiong,Xu, Xiwei,Wang, Binbo,Yuan, Wangchao,Zhou, Shenghua,You, Shusen,Zhu, Jin
, p. 1484 - 1497 (2019/03/26)
Epoxy resins have been widely used in several materials including carbon fiber composites; however, they are arduous to recycle. In this study, for the first time, a Schiff base epoxy thermoset combining excellent recyclability and high performance was facilely prepared from a synthesized formyl group-containing vanillin-based monoepoxide and a diamine via in situ formation of the Schiff base structure and epoxy network. The chemical structure of the monoepoxide and its cross-linked network were characterized in detail. In addition, the thermal and mechanical properties, recyclability of the thermoset and its application in carbon fiber composite were systematically investigated. The results showed that the thermoset possessed a similar glass transition temperature of 172 °C, a tensile strength of 81 MPa and a modulus of 2112 MPa, and higher thermal stability with the degradation temperature for 5% weight loss of 323 °C and elongation at break of 15% in comparison with a bisphenol A epoxy resin. Moreover, it exhibited superior reprocessing recyclability due to the vitrimer or CAN nature of its Schiff base network. Furthermore, it could also be completely degraded under mild acidic conditions, leading to the quick and nondestructive recycling of its carbon fiber composite.
Recyclable and Malleable Epoxy Thermoset Bearing Aromatic Imine Bonds
Zhao, Shou,Abu-Omar, Mahdi M.
, p. 9816 - 9824 (2019/01/03)
A method for preparing reprocessable epoxy thermoset is presented. The process is composed of synthesis of a bisphenol monomer bridged by an imine bond, glycidylation of the bisphenol, and cross-linking with a hardener to form thermoset. The resulting epo
Epoxy thermosets from model mixtures of the lignin-to-vanillin process
Fache,Boutevin,Caillol
, p. 712 - 725 (2016/02/12)
Epoxy thermosets were prepared from mixtures of phenolics modelling the product stream of the lignin-to-vanillin process. Vanillin is one of the only mono-aromatic compounds produced on an industrial scale from lignin. This process leads to mixtures of phenolic compounds. Isolation of pure vanillin is costly both economically and environmentally. The present work demonstrates that these purification steps are not necessary in order to prepare high-performance epoxy thermosets from biomass. Model mixtures of depolymerization products of lignins from both softwood and hardwood were prepared. These mixtures were subjected in a first step to a Dakin oxidation in order to increase their phenolic functionality. In the second step, they were glycidylated to obtain mixtures of epoxy monomers. Each of the components of the mixtures was individually subjected to the same reactions to provide further insights on their reactivity. Epoxy thermosets were conveniently prepared from these epoxy monomer mixtures. These potentially bio-based epoxy thermosets displayed outstanding thermo-mechanical properties while avoiding environmentally damaging purification steps. Thus, their production could advantageously be integrated in a biorefinery as a high value added product from lignin processing.
Regioselective cleavage of 2-aryloxymethyloxiranes to 3-aryloxy-l- halogenopropan-2-ols
Maciejewski,Poltorak,Kaminska
experimental part, p. 595 - 604 (2009/12/26)
A series of new 2-ary loxymethy loxiranes prepared from epichlorohydrin and substituted phenols was subjected to nucleophilic opening of the oxirane ring. A comparison of regioselectivity and product yield for oxirane cleavage by means of aqueous hydrohalogenic acids or lithium tetrahalogenocuprates under anhydrous conditions was performed. The latter method provided very high regioselectivity for 3-aryloxy-l-halo-genopropan-2-ols as well as excellent yields.
Synthesis, β-adrenergic receptor binding and antihypertensive potential of vanillin-derived phenoxypropanolamines
Coumar, Mohane S.,Jindal, Dharam P.,Bruni, Giancarlo,Massarelli, Paola,Singh, Randhir,Sharma, Amit K.,Nandakumar,Bodhankar, Subhash L.
, p. 903 - 909 (2008/12/23)
Synthesis of vanillin-derived phenoxypropanolamines is carried out by condensing 4-hydroxy-3-methoxybenzaldehyde (vanillin) 1 with epichlorohydrin, followed by treatment with iso-propylamine or tert-butylamine to open the epoxy ring. Percentage inhibition of [3H]dihydroalprenolol binding to both β1- and β2-adrenergic receptors by the newly synthesized compounds is assessed in vitro using turkey erythrocyte membrane (β1) and lung homogenate of rats (β2). Formyl derivatives 8 and 9 showed maximum inhibitory effect in binding assay and are non-selective similar to propranolol. On the other-hand, aldoxime compounds 10 and 11 have preference for β1adrenergic receptors similar to atenolol. Also four of the compounds 8-11 are evaluated for their anti-hypertensive potential, in left renal artery ligation and fructose induced hypertension models. 4-(3-tert-Butylamino-2-hydroxy-propoxy)-3-methoxy- benzaldehyde oxime 11 shows antihypertensive effect better than propranolol.
The new generation dihydropyridine type calcium blockers, bearing 4-phenyl oxypropanolamine, display α-/β-adrenoceptor antagonist and long-acting antihypertensive activities
Liang, Jhy-Chong,Yeh, Jwu-Lai,Wang, Chia-Sui,Liou, Shwu-Fen,Tsai, Chieh-Ho,Chen, Ing-Jun
, p. 719 - 730 (2007/10/03)
A new series of dihydropyridine derivatives, bearing oxypropanolamine moiety on phenyl ring at the 4-position of the dihydropyridine base, were prepared. Oxypropanolamine was synthesized by replacing the phenolic OH of vanillin or other compounds, having a phenyl aldehyde group, with epichlorohydrin, followed by cleavaging the obtained epoxide compounds with tert-butylamine, n-butylamine or 2-methoxy-1-oxyethylamino benzene (guaiacoxyethylamine), respectively. Obtained various oxypropanolamine compounds, still remaining a phenyl aldehyde moiety, were then performed by Hantzsch condensation reaction with methylacetoacetate or ethylacetoacetate, respectively, to give our new series of dihydropyridine linked with the 4-phenyl ring. These compounds were evaluated for inotropic, chronotropic, and aorta contractility that associated with calcium channel and adrenoceptor antagonist activities. Dihydropyridine derivatives that with oxypropanolamine side chain on their 4-phenyl ring associated α-/β-adrenoceptor blocking activities created a new family of calcium entry and the third generation β-adrenoceptor blockers. Optimizing this research to obtain more potent α-/β-adrenoceptor blocking and long-acting antihypertensive oxypropanolamine on the 4-phenyl ring of dihydropyridine series compounds was thus accomplished and classified as third generation dihydropyridine type calcium channel blockers, in comparison with previous short-acting type nifedipine and long-acting type amlodipine. We concluded that compounds 1a, 1b and 1g showed not only markedly high calcium-antagonistic activity but also the highest antihypertensive effect; compounds 1b, 1c, 1f, 1g, 1i and 1j induced sustained antihypertensive effects are major and attributed to their calcium entry and α-adrenoceptor blocking activities in the blood vessel due to their introduction of 2-methoxy, 1-oxyethylamino benzene moiety in the side chain on the 4-phenyl ring of dihydropyridine. Bradycardiac effects of all the compounds 1a-1j resulted from calcium entry and β-adrenoceptor blocking, which attenuate the sympathetic activation-associated reflex tachycardia in the heart. We selected compound 1b as candidate compound for further pharmacological and pre-clinical evaluation studies.
A new aspect of view in synthesizing new type β-adrenoceptor blockers with ancillary antioxidant activities
Huang, Yeun-Chih,Wu, Bin-Nan,Yeh, Jwu-Lai,Chen, Sheue-Jiun,Liang, Jyh-Chong,Lo, Yi-Ching,Chen, Ing-Jun
, p. 1739 - 1746 (2007/10/03)
A series of vanilloid-type β-adrenoceptor blockers derived from traditional Chinese herbal medicines were synthesized and tested for their antioxidant and adrenoceptor antagonistic activities. They all possessed significant β-adrenoceptor blocking activities under in vitro experiments and radioligand binding assays. In addition, some compounds were further examined in in vito tests and produced antagonist effects matching that of propranolol and labetalol by measurements of antagonism toward (-)isoproterenol-induced tachycardia and (-)phenylephrine-induced pressor responses in anesthetized rats. Furthermore, all of the compounds had antioxidant effects inherited from their original structures. In conclusion, compound 11 had the most potent β-adrenoceptors blocking activity, 12 and 13 possessed high cardioselectivity, whereas 14, 15 and 16 possessed additional α-adrenoceptor blocking activity and 15 is the most effective antioxidant of all. the antioxidant activity may be due to their @α and β unsaturated side chain at position 1 and ortho-substituted methoxy moiety on 4-phenoxyethylamine. Copyright
