A simple and efficient way to synthesize optically active polyamides by solution polycondensation of di-O-methyl-L-tartaryl chloride with diamines

Wu Z.; Huang Y.; Zhang C.; Zhu D.; Bian Z.; Ding M.; Gao L.; Yang Z.

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A simple and efficient way to synthesize optically active polyamides by solution polycondensation of di-O-methyl-L-tartaryl chloride with diamines

机译：通过二-O-甲基-L-酒石酰氯与二胺的溶液缩聚来合成旋光聚酰胺的简单有效方法

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摘要

A series of optically active polyamides containing di-O-methyl-L-tartaryl moieties in the main chain were synthesized by polycondensation of di-O-methyl-L-tartaryl chloride 5 with diamines and characterized by gel permeation chromatography, UV-vis, circular dichroism (CD), IR, and NMR spectroscopies. The polycondensation reaction could be carried out under mild conditions and the reaction time was short (2-3 h). The key monomer 5 prepared from L-tartaric acid via esterification, etherification, hydrolysis, and chlorination was easily purified by vacuum sublimation. These polyamides with number average molecular weights ranging from 14,000 to 35,000, displayed large optical activity in dimethyl sulfoxide solution, and their specific optical rotations oscillated between 87.2° and 210.7° depending on the structures of the diamines. The glass transition temperatures of these polyamides were in the range of 106-191°C, and the 10% mass loss occurred at temperature above 300°C. The polyamides derived from aromatic diamines exhibited higher T_g and thermal stability than those derived from aliphatic diamines.

机译：通过主链上的二-O-甲基-L-叔丁基芳基氯5与二胺的缩聚反应，合成了一系列在主链上包含二-O-甲基-L-叔丁基芳基的旋光聚酰胺，并通过凝胶渗透色谱，UV-vis，圆二色性（CD），IR和NMR光谱。缩聚反应可以在温和的条件下进行，反应时间短（2-3小时）。由L-酒石酸经酯化，醚化，水解和氯化制备的关键单体5易于通过真空升华纯化。这些数均分子量为14,000至35,000的聚酰胺，在二甲亚砜溶液中表现出较大的光学活性，并且取决于二胺的结构，它们的比旋光度在87.2°至210.7°之间振荡。这些聚酰胺的玻璃化转变温度在106-191℃的范围内，并且在高于300℃的温度下发生10％的质量损失。衍生自芳族二胺的聚酰胺比衍生自脂族二胺的聚酰胺表现出更高的T g和热稳定性。

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《Journal of Applied Polymer Science》 |2010年第6期|共10页
作者
Wu Z.; Huang Y.; Zhang C.; Zhu D.; Bian Z.; Ding M.; Gao L.; Yang Z.;
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正文语种 eng
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Di-O-methyl-L-tartaryl chloride; Optically active; Polyamides; Synthesis; Vacuum sublimation;

机译：二-O-甲基-L-酒石酰氯;光学活性;聚酰胺;合成;真空升华;

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1. A simple and efficient way to synthesize optically active polyamides by solution polycondensation of di-O-methyl-L-tartaryl chloride with diamines [J] . Wu Z., Huang Y., Zhang C., Journal of Applied Polymer Science . 2010,第6期

机译：通过二-O-甲基-L-酒石酰氯与二胺的溶液缩聚来合成旋光聚酰胺的简单有效方法
2. Synthesis and characterization of new optically active polyamides containing 2-(4-nitro-1,3-dioxoisoindolin-2-yl)succinic acid and aromatic diamines via direct polycondensation [J] . KHALIL FAGHIHI, MORTEZA ABSALAR, MOHSEN HAJIBEYGI Turkish journal of chemistry . 2010,第1期

机译：通过直接缩聚反应合成和表征包含2-（4-硝基-1,3-二氧代异吲哚-2-基）琥珀酸和芳族二胺的新型光学活性聚酰胺
3. Microwave-assisted and conventional polycondensation reaction of optically active N,N '-(4,4 '-sulphonediphthaloyl)-bis-L-leucine diacid chloride with aromatic diamines [J] . Mallakpour S., Kowsari E. Journal of Applied Polymer Science . 2004,第5期

机译：光学活性N，N'-（4,4'-磺基二邻苯二甲酰基）-双-L-亮氨酸二酰氯与芳族二胺的微波辅助和常规缩聚反应
4. Synthesis and Characterization of Novel Optically Active Poly(amide-imide)s Containging 5,5-disubstituated Hydantoin Derivatives in Main Chain by Microwave Assisted Polycondensation [C] . . -1

机译：微波辅助缩合反应合成主链含5,5-二取代乙内酰脲衍生物的新型旋光活性聚酰胺酰胺
5. OPTICALLY ACTIVE POLYAMIDES: POLY ALPHA, BETA, GAMMA, AND EPSILON-METHYL EPSILON-CAPROLACTAM. [D] . PARKER, GORDON MORSE. 1965

机译：光学活性聚酰胺：聚Alpha，BETA，γ和ε-甲基ε-己内酰胺。
6. Molten salt-supported polycondensation of optically active diacid monomers with an aromatic thiazole-bearing diamine using microwave irradiation [O] . Shadpour Mallakpour, Amin Zadehnazari 2014

机译：微波辐射使旋光性二酸单体与含芳族噻唑的二胺进行熔融盐负载缩聚
7. Molten salt-supported polycondensation of optically active diacid monomers with an aromatic thiazole-bearing diamine using microwave irradiation [O] . Shadpour Mallakpour, Amin Zadehnazari 2014

机译：使用微波辐射，熔融盐负载的光学活性二酸单体与带有芳族噻唑的二胺的缩聚反应
8. Poly-phenylated diamines and their use as polycondensation monomers in the synthesis of polyamide, poly(amide-imide), and polyimide polymers [R] . 1992

机译：聚苯基二胺及其在聚酰胺，聚酰胺酰亚胺和聚酰亚胺聚合物合成中作为缩聚单体的用途

A simple and efficient way to synthesize optically active polyamides by solution polycondensation of di-O-methyl-L-tartaryl chloride with diamines

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