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Chiral polyester compounds and preparation method thereof

A compound and polyester technology, applied in biochemical equipment and methods, methods based on microorganisms, microorganisms, etc., to achieve the effect of single configuration and broad application development prospects

Inactive Publication Date: 2019-05-03
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The enzymatic polymerization of chiral carbon-containing diesters and non-chiral carbon-atom diols to synthesize chiral polyesters has not yet been reported.

Method used

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  • Chiral polyester compounds and preparation method thereof
  • Chiral polyester compounds and preparation method thereof
  • Chiral polyester compounds and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Prepare a chiral polyester compound:

[0034]

[0035] 1) Weigh 1.0mmol N-benzyloxycarbonyl-L-aspartic acid dimethyl ester, 1.1mmol 1,4-butanediol and dissolve in 1.0mL toluene, add Candida antarctica lipase B (enzyme The amount used is 15% of the mass of N-benzyloxycarbonyl-L-aspartic acid dimethyl ester), pre-polymerized at normal pressure and temperature at 50°C for 24 hours, then kept the reaction temperature constant at an absolute pressure of 0.01 Polymerization reaction 48h under the condition of MPa, collect reaction product;

[0036] 2) The reaction product obtained in step 1) was dissolved in 1.0 mL of dichloromethane solution, filtered, and the filtrate was distilled under reduced pressure until viscous to obtain a polymer;

[0037] 3) The polymer obtained in step 2) was dissolved in 1.0 mL of a mixed solution of methanol and dichloromethane with a volume ratio of 5:1, and recrystallized, the macromolecular polymer was precipitated, filtered, and the filt...

Embodiment 2

[0041] Prepare a chiral polyester compound:

[0042]

[0043] 1) Weigh 1.0mmol N-benzyloxycarbonyl-L-aspartic acid dimethyl ester, 1.1mmol 1,8-octanediol and dissolve in 1.0mL toluene, add Candida antarctica lipase B (enzyme catalyst The amount used is 25% of the mass of N-benzyloxycarbonyl-L-aspartic acid dimethyl ester), pre-polymerized at normal pressure and temperature at 80°C for 24 hours, then kept the temperature constant at an absolute pressure of 0.01MPa Polymerization reaction 24h under the condition of condition, collect reaction product;

[0044] 2) The reaction product obtained in step 1) was dissolved in 1.0 mL of dichloromethane solution, filtered, and the filtrate was distilled under reduced pressure until viscous to obtain a polymer;

[0045] 3) The polymer obtained in step 2) was dissolved in 1.0 mL of a mixed solution of methanol and dichloromethane with a volume ratio of 5:1, recrystallized, and a macromolecular polymer was precipitated, filtered to obt...

Embodiment 3

[0053] Prepare a chiral polyester compound:

[0054]

[0055] 1) Weigh 1.0mmol of N-benzyl-L-aspartic acid dimethyl ester, 1.1mmol of 1,12-dodecanediol and dissolve it in 1.0mL of toluene, add Candida antarctica lipase B (enzyme catalyst The amount used is N-benzyl-L-aspartic acid dimethyl ester mass 30%), under the condition of normal pressure and temperature of 80 ℃ pre-polymerization reaction for 24h, then keep the temperature constant, under the condition of absolute pressure 0.01MPa Polymerization reaction 48h, collect reaction product;

[0056] 2) The reaction product obtained in step 1) was dissolved in 1.0 mL of dichloromethane solution, filtered, and the filtrate was distilled under reduced pressure until viscous to obtain a polymer;

[0057] 3) The polymer obtained in step 2) was dissolved in 1.0 mL of a mixed solution of methanol and dichloromethane with a volume ratio of 5:1, recrystallized, and a macromolecular polymer was precipitated, filtered to obtain 180 ...

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Abstract

The invention discloses chiral polyester compounds and a preparation method thereof. The chiral polyester compounds have structural units of N-substituted-L-aspartic acid and long-chain fatty diol, and have a structural general formula represented by a formula (I) shown in the description, wherein in the formula (I), a substituent R is benzyloxycarbonyl, t-butyloxycarboryl or benzyl; m = 2, 4, 6or 10; and n represents an integer of 30 to 105; and a substituent of the N-substituted-L-aspartic acid is the same as the substituent R in the formula (I). The method provided by the invention adoptsa diester containing a chiral carbon atom and a diol without a chiral carbon atom as raw materials for the first time, and the novel chiral polyester compounds are synthesized under the action of a candida antarctica lipase B catalyst; and the compounds have the advantage of single configuration, are environmentally-friendly biodegradable materials, and have broad application prospects.

Description

technical field [0001] The invention belongs to the technical field of polymer compounds, and in particular relates to a chiral polyester compound. Background technique [0002] Chiral polymers refer to polymers containing chiral groups in the main chain or side chain structure. They are widely found in natural products such as proteins, polysaccharides, and nucleic acids, and have irreplaceable roles in nature. Due to the asymmetric molecular structure of chiral polymers, chiral polymers often have properties that ordinary polymers do not have. For example, some chiral polymers with special structures can chelate heavy metal ions in heavy metal sewage and can be used for heavy metal sewage treatment. In recent years, artificially synthesized chiral polymers have developed rapidly, showing excellent application prospects in chiral recognition, nonlinear optics, biomedical materials, and gene therapy. At the same time, polyester materials are also a new type of polymer mate...

Claims

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Application Information

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IPC IPC(8): C08G63/685C12P7/62C12R1/72
Inventor 费正东范萍陈枫钟明强
Owner ZHEJIANG UNIV OF TECH
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