PhSGBL polymer, and preparation method and application thereof

A bicyclic lactone and polymer technology, which is applied in the field of bicyclic lactone polymer and its preparation and application, can solve the problems of small polymer molecular weight, poor impact resistance, and reduced hydrophilicity, and achieve narrow molecular weight distribution, Broaden application scenarios and controllable molecular weight

Active Publication Date: 2019-10-08
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Although polyester materials are widely used in drug carriers, commercial packaging, surgical repair materials, etc. due to their excellent properties, polyester materials also have many disadvantages: (1) The relative molecular weight of the polymer is small and the distribution is wide, making The strength of the material is reduced, the glass transition temperature is low, the brittleness is high, and the impact resistance is poor, so it cannot meet the requirements of wide application (Table 1); (2) The presence of ester bonds in polyester materials leads to the hydrophilicity of materials It is bound to be reduced, resulting in a reduction in its biocompatibility, which leads to rejection in the body; (3) expensive; (4) the degradation cycle is difficult to control

Method used

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  • PhSGBL polymer, and preparation method and application thereof
  • PhSGBL polymer, and preparation method and application thereof
  • PhSGBL polymer, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] The preparation of embodiment 1PPhSGBL

[0069] 1) Synthesis of phenylsulfur chloride (PhSCl)

[0070] At 0°C, diphenyl disulfide (10 g, 45.8 mmol) and triethylamine (0.65 ml, 4.6 mmol) were dissolved in 75 ml of benzene and stirred under argon atmosphere for 15 min. Then, sulfonyl chloride (14.73g, 110mmol) was dissolved in 110mol of dichloromethane, and slowly added dropwise to the above solution. After the dropwise addition, the mixture was continuously stirred for 1h and the reaction was stopped. The reaction solution was concentrated by rotary evaporation to remove the solvent, and then subjected to vacuum distillation (0.75 torr, 50° C.) to obtain phenylsulfur chloride as an orange liquid (10.7 g, yield: 81.7%). Above synthetic route is as follows:

[0071]

[0072] 2) Synthesis of lactone monomer PhSGBL

[0073] 3-cyclohexene-1-carboxylic acid (7g, 55mmol) and triethylamine (7.7ml, 55mmol) were dissolved in 50ml of dichloromethane at room temperature, stirr...

Embodiment 2

[0081] The random copolymer synthesis of embodiment 2PPhSGBL and CL

[0082] In the glove box, according to the scale [CL] 0 / [PhSGBL] 0 =0 / 100, 20 / 80, 40 / 60, 60 / 40, 80 / 20, 100 / 0 (when the endpoint value is 0, it means that the reaction monomer is not contained) the monomer PhSGBL (0.4g, 1.71mmol), ε-caprolactone (the amount added is calculated according to the proportion), organic base 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) (9.52mg, 0.0684mmol), initiator ethylenedi Alcohol (EG) (1.91ml, 0.0342mmol) and 1ml solvent dichloromethane (DCM) were added to the reaction vessel, the reaction temperature was 30°C, and the reaction was stopped after stirring for 13-15h.

[0083] After the reaction, it was dissolved with 2ml of tetrahydrofuran (THF), then dropped into glacial ether to settle, obtained by suction filtration, and dried in a vacuum oven at 40°C for 12 hours to obtain random copolyesters with different proportions of PhSGBL and CL. Above synthetic route is as follows:...

Embodiment 3

[0089] Embodiment 3 contains the synthesis of sulfoxide or sulfone polymer

[0090] Polyester PPhSGBL (100mg, M n =16000, ), 20ml of solvent chloroform (DCM) were added to the reaction vessel, the reaction temperature was set at 25°C, and the oxidant m-chloroperoxybenzoic acid (m-CPBA) was gradually added to it, stirring for 10-15min after each addition, and at the same time according to In the above method, multiple groups of parallel experiments were performed, and different amounts of oxidants were added to each group, and then a small amount of reaction solution was taken for FT-IR testing, as shown in Figure 11 as shown. Figure 11 Among them, the molar ratios of oxidant and PPhSGBL corresponding to the top-down curve are 0:1, 0.27:1, 0.54:1, 0.81:1, 1.08:1, 1.35:1, 1.62:1, 1.89:1, 2.16:1, 2.43:1, 2.70:1, in the picture, 1041.5cm -1 The peak at is the characteristic peak of S=O bond, 1303.8cm -1 The peak at is the characteristic peak of the O=S=O bond, and the resu...

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Abstract

The invention relates to a polymerization method of PhSGBL and an application of the prepared polyester. The PPHSGL prepared by the method is controllable in molecular weight and narrow in molecular weight distribution index. A sulfoxide or sulfone polymer can be further prepared by utilizing oxidation performance of the polymer. The PHSGBL has acid degradation performance and thermal depolymerization recovery performance simultaneously. The invention also provides a method for copolymerizing the PHSGBL and epsilon-caprolactone (CL) to obtain a random copolymer.

Description

technical field [0001] The invention relates to the technical field of polymer preparation, in particular to a bicyclic lactone polymer and its preparation and application. Background technique [0002] Polyester refers to a polymer with ester group chain (-COOH-) in the main chain, and aliphatic polyester is an important class of biodegradable polymer materials. They can be chemically degraded in water, body fluids or other solvents, that is, simple ester bond hydrolysis or enzymatic degradation and chain scission. Because of their good biocompatibility and biodegradability, these materials have been widely used. As early as the 1970s, the U.S. FDA has approved its clinical use. Taking advantage of its degradable and absorbed characteristics in the body, it can be used in the repair field and the carrier of drug sustained release systems, such as wound sutures; processed into The polyester material of the film can be used for commercial packaging; it can also be used as a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G63/688C08G63/78C08G75/18C08G75/20
CPCC08G63/6882C08G63/78C08G75/18C08G75/20
Inventor 潘向强吴金安朱健朱秀林
Owner SUZHOU UNIV
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