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Polyester and preparation method thereof

A technology of polyester and polymerization degree, which is applied in the direction of pharmaceutical formula, medical preparation of non-active ingredients, medical science, etc., to achieve the effect of high efficiency and good hydrophilicity

Active Publication Date: 2012-11-21
CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there have been no reports on the modification of aliphatic polyesters with serine as a raw material

Method used

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  • Polyester and preparation method thereof
  • Polyester and preparation method thereof
  • Polyester and preparation method thereof

Examples

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preparation example Construction

[0041] The present invention also provides a method for preparing the polyester having the structure of formula (I), including:

[0042] Using diethyl zinc as a catalyst, the aliphatic polyester and N-tritylserine lactone are polymerized to form a copolymer, and the aliphatic polyester is polyglycolide, polycaprolactone or polylactide;

[0043] The copolymer is mixed with trifluoroacetic acid, and reacts at 0°C to 35°C to produce a polyester having a structure of formula (I).

[0044] In the present invention, aliphatic polyester and N-tritylserine lactone are used as raw materials to prepare a polyester having a structure of formula (I). The aliphatic polyester is polyglycolide, polycaprolactone or polylactide, which can be purchased from the market. The N-tritylserine lactone is preferably prepared according to the following method:

[0045] Mixing serine and trityl chloride, reacting in an organic solvent to obtain N-tritylserine, the organic solvent being a mixed solution of dich...

Embodiment 1

[0085] Example 1 Synthesis of N-tritylserine lactone

[0086] Under the protection of nitrogen, mix 6.3g serine, 100mL dichloromethane and 26mL trimethylchlorosilane, reflux for 1h at 50℃, cool to room temperature, add a mixture consisting of 29.4mL triethylamine and 60mL dichloromethane, and warm up Reflux at 50°C for 45 minutes, cool to 0°C, then add a mixture consisting of 3.6mL methanol and 15mL dichloromethane, 8.4mL triethylamine and 16.7g trityl chloride. After stirring for 12h at room temperature, add 12mL methanol And 8.4 mL of triethylamine, stirred for 15 min to obtain a mixed solution; remove the solvent and volatile substances in the mixed solution under vacuum to obtain a light yellow substance; use 300 mL of ethyl acetate to dissolve the light yellow substance, and use 150 mL of a 5% citric acid aqueous solution with a mass concentration of 5% was washed three times, and then three times with water. The obtained solution was rotary evaporated to obtain a crude prod...

Embodiment 2

[0088] Example 2 Synthesis of poly(glycolide-serine ester)

[0089] 0.522g (4.5mmol) of glycolide, 0.1645g (0.5mmol) of N-tritylserine lactone prepared in Example 1, 1.5mL of toluene and Diethylzinc with a molar ratio of 1:100 to N-tritylserine lactone, reacted at 90°C for 12 hours, quickly cooled the reaction flask, and removed the solvent. The product was dissolved in chloroform and then settled in methanol. , And then filtered, washed, and dried to obtain poly(glycolide-N-polytritylserine ester);

[0090] Add 0.2087g of poly(glycolide-N-polytritylserine ester), 10mL of dichloromethane, 0.0125mL of trifluoroacetic acid and 0.03mL of methanol to the flame-baked reaction flask, stir to dissolve the mixture, After reacting at 0°C for 3 hours, the product was concentrated and then settled in ether to obtain poly(glycolide-serine ester), in which the molar percentage of the serine ester repeating unit was 10%.

[0091] The poly(glycolide-serine ester) was measured by gel permeation ch...

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Abstract

The invention provides a polyester with a structure in a formula (I), wherein x and y are degrees of polymerization, x is greater than or equal to 1 and less than or equal to 500, y is greater than or equal to 1 and less than or equal to 200, and x and y do not take the minimum value at the same time; n is equal to 0 or 4; when n is equal to 0, R is hydrogen or methyl; and when n is equal to 4, Ris hydrogen. The invention also provides a preparation method of the polyester with the structure in the formula (I). The invention also provides a polyester with a structure in a formula (II), wherein x and y are polymerization degrees, x is greater than or equal to 1 and less than or equal to 500, y is greater than or equal to 1 and less than or equal to 200, and x and y do not take the minimumvalue at the same time; n is equal to 0 or 4; when n is equal to 0, R is hydrogen or methyl; when n is equal to 4, R is hydrogen; and A- is the acid radical of an acid of which the acidity is stronger than that of trifluoroacetic acid. The polyester with the structure in the formula (I) or the formula (II) provided by the invention is a random copolymer of aliphatic polyester and serine ester, contains modifiable side amido, and has good hydrophilicity, biological compatibility and degradability.

Description

Technical field [0001] The invention relates to the technical field of high molecular polymers, in particular to a polyester and a preparation method thereof. Background technique [0002] Aliphatic polyesters such as polylactic acid, polyglycolide and polycaprolactone have good biocompatibility and have been clinically applied as biomedical materials in the fields of surgical repair and controlled drug release. However, aliphatic polyester itself does not have biologically active and reactive functional groups, its cell adhesion is poor, and its physical and chemical properties are difficult to control. [0003] An important way to expand the application field of aliphatic polyester is to modify aliphatic polyester to introduce reactive functional groups and improve the cell adhesion of aliphatic polyester. The metabolites that exist in organisms such as malic acid and amino acids have the characteristics of non-toxicity, good biocompatibility, and more active reactive groups, an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G63/91C08G63/685A61K47/34A61L27/18
Inventor 黄宇彬魏英景遐斌陈学思
Owner CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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