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Amphipathic tadpole-shaped block copolymer and preparation method thereof

A block copolymer and amphiphilic technology, which is applied in the field of amphiphilic tadpole-shaped block copolymer and its preparation, can solve the problems such as no research report on amphiphilic tadpole-shaped block copolymer

Inactive Publication Date: 2017-05-31
YUNNAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the research on the copolymers of PE and PNVCL is mostly focused on the linear copolymer, and there is no literature search about the amphiphilic tadpole-shaped block of aliphatic polyester (PE) and poly(N-vinylcaprolactam) (PNVCL) Copolymer Research Reports

Method used

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  • Amphipathic tadpole-shaped block copolymer and preparation method thereof
  • Amphipathic tadpole-shaped block copolymer and preparation method thereof
  • Amphipathic tadpole-shaped block copolymer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0088] Add 0.28 g of ethylene glycol, 29.2 μL of stannous octoate, and 20 mL of ε-caprolactone (ε-CL) into a dry Schlenk flask, vacuumize and fill with nitrogen for several times, then place it in an oil bath at 100°C and stir for 14 hours. After cooling, 10 mL of ethanol was added, and the crude product was obtained by filtration. The crude product was dissolved in a small amount of THF, and co-precipitated three times with n-hexane to obtain polycaprolactone (HO-PCL-OH) with α, ω-double-terminal hydroxyl groups.

[0089] Take 4.5g HO-PCL-OH into a three-necked bottle, add 50mL CH 2 Cl 2 and 1.77mL triethylamine, in an ice-water bath, add 5mL of CH dissolved in 1.06mL 2-bromopropionyl bromide (BPB) 2 Cl 2 The solution was dripped and reacted at room temperature for 48h. Filter, add 100mLCH to the filtrate 2 Cl 2 After dilution, it was washed successively with 1.0M HCl (3×50 mL), 1.0M NaOH (3×50 mL), and 1.0M NaCl (3×50 mL) solutions, respectively. Anhydrous MgSO for or...

Embodiment 2

[0092] Take 0.42g X-PCL-X into a dry reaction bottle, add 5mL CH 2 Cl 2 make it dissolve, N 2 Under protection, 14.6 mg of n-butylamine and a small amount of tributylphosphine were added, and the reaction was stirred for 2 h. After the reaction, co-precipitate with petroleum ether 3 times. The precipitate was collected and dried at room temperature to obtain polycaprolactone (HS-PCL-SH) with α,ω-double-terminal mercapto groups, with a yield of 70%.

Embodiment 3

[0094] N 2 Under protection, 1.13g DTCA, 1.0g DCC were dissolved in 40mL CH 2 Cl 2, placed in an ice-water bath, slowly dropwise added 20 mL of CH with 0.5 g of propynyl alcohol and 60 mg of DMAP 2 Cl 2 After the solution was dropped, it was reacted in an ice-water bath for 1 h, and at room temperature for 24 h. After filtration, the filtrate was concentrated, and the residue was dissolved in ether, filtered, and the ether was distilled off to obtain a crude product. The crude product was separated by silica gel column chromatography (V 石油醚 :V 乙酸乙酯 =20:1) A thiocarbamate chain transfer agent (alknyl-CTA) with a terminal alkynyl group was obtained with a yield of 70%.

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Abstract

The invention discloses an amphipathic tadpole-shaped block copolymer and a preparation method thereof, and belongs to the technical field of the preparation of high molecular materials. Aliphatic polyester with alpha,omega-double terminal thiol and poly(N-vinyl caprolactam) with terminal alkynyl are first prepared, and then, through a thiol-yne click reaction between the aliphatic polyester and the poly(N-vinyl caprolactam), an amphipathic single tadpole-shaped block copolymer I is made; four-arm star-shaped polyester with terminal thiol and the poly(N-vinyl caprolactam) with the terminal alkynyl are prepared, and then, through a thiol-yne click reaction between the four-arm star-shaped polyester and the poly(N-vinyl caprolactam), an amphipathic double tadpole-shaped block copolymer II is made. A copper-catalysis-free thiol-yne reaction is applied to the preparation of a tadpole-shaped block copolymer; the pollution problem of a product, which is caused by the use of a copper catalyst, is solved; an obtained product is pure and is easily purified; a reaction condition is easily realized and is safe; the reaction efficiency is high; the amphipathy, the temperature responsiveness, biodegradability and the biocompatibility are integrated on the product; the amphipathic tadpole-shaped block copolymer has a wide application prospect in the field of biological medicines.

Description

technical field [0001] The invention belongs to the technical field of polymer material preparation, and specifically relates to an amphiphilic monotadpole-shaped block copolymer with a ring-shaped aliphatic polyester as the head and a linear poly(N-vinyl caprolactam) as the tail, and a two A single tadpole-shaped block copolymer headed by a cyclic aliphatic polyester and tailed by linear poly(N-vinylcaprolactam) An amphiphilic bitadpole-shaped block formed by two cyclic aliphatic polyesters sharing one carbon atom Copolymers and methods for their preparation. Background technique [0002] Cyclic polymers, including monocyclic and polycyclic polymers, are a class of polymers with special topology and special properties different from linear and branched polymers. The ring topology is also one of the structures that exist widely in nature. Studies in molecular biology and biochemistry have found that there are also some ring-shaped biomacromolecules in organisms, such as cir...

Claims

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Application Information

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IPC IPC(8): C08G81/00A61K9/107A61K47/34
CPCA61K9/0002A61K9/1075A61K47/34C08G81/00C08G2230/00
Inventor 毕韵梅李杰杨耀宗唐刚马永翠
Owner YUNNAN NORMAL UNIV
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