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Method for synthesizing polylactic acid-block-polyN-isopropyl acrylamide temperature-sensitive material

A technology of isopropylacrylamide and temperature-sensitive materials, applied in wave energy or particle radiation treatment materials, drug combinations, pharmaceutical formulations, etc. Problems such as the preparation method of N-isopropylacrylamide, to achieve the effect of mild reaction and easy operation

Inactive Publication Date: 2015-06-10
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Its disadvantages are: 1. This document does not provide the preparation method of star polylactic acid-poly N-isopropylacrylamide
2. This document is only used for the synthesis of polylactic acid-polyN-isopropylacrylamide with a linear structure, and cannot be used for refunctionalization of materials
making it limited in laboratory and industrial production
So far, star-shaped biodegradable polylactic acid-block-polyN-isopropylacrylamide temperature-sensitive materials with porphyrin as the core have not been reported

Method used

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  • Method for synthesizing polylactic acid-block-polyN-isopropyl acrylamide temperature-sensitive material
  • Method for synthesizing polylactic acid-block-polyN-isopropyl acrylamide temperature-sensitive material

Examples

Experimental program
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Embodiment 1

[0015] Embodiment 1: The preparation method of star-shaped polylactic acid-block-poly N-isopropylacrylamide temperature-sensitive material with porphyrin as the core

[0016] Tetrakis(2-hydroxyethyl)phenylporphyrin (68.4mg, 0.08mmol) was used as the initiator, DMAP (78.2mg, 0.64mmol), L-lactide (922mg, 6.4mmol) were successively added to the fully dried In the test tube, seal it with an inversion plug. After the vacuum line is operated and evacuated nitrogen for three times, add 0.2mLTHF and put it in a constant temperature oil bath at 50°C. After reacting for 24h, cool the test tube to room temperature, and dissolve the obtained solid in 5mLCH 2 Cl 2 , and settled dropwise in 50 mL of ice methanol under magnetic stirring. The product obtained after filtration was vacuum-dried at 40° C. to constant weight. Yield 931.7 mg, 87.2% yield.

[0017] Add dried star polylactic acid (SPPLA-OH) (110.4 mg, 0.01 mmol) and benzyl trithiocarbonate propionic acid (BSPA) (21.76 mg,...

Embodiment 2

[0019] Embodiment 2: The preparation method of star-shaped polylactic acid-block-poly N-isopropylacrylamide temperature-sensitive material with porphyrin as the core

[0020] The preparation of star polylactic acid (SPPLA-OH) and macromolecular chain transfer agent SPPLA-BSPA with porphyrin as the nucleus terminal hydroxylation is the same as in Example 1.

[0021] Add SPPLA-BSPA (20mg, 0.002mmol), NIPAAm (43.1mg, 0.4mmol) and AIBN (0.2mg, 0.0016mmol) into a 25ml round bottom flask, then add 0.8ml of THF to fully dissolve them. After evacuating nitrogen three times with a vacuum line, react in a constant temperature oil bath at 70° C. for 12 hours. After the reaction, cool in an ice-water bath, settle in anhydrous ether, centrifuge, take the solid, dissolve it in THF, settle with n-hexane, remove unreacted NIPAAm monomer, and centrifuge to obtain a solid product. Drying in vacuo at constant temperature to constant weight yielded 48.6 mg star-shaped polylactic acid-b...

Embodiment 3

[0022] Example 3: The preparation method of the star-shaped polylactic acid-block-poly N-isopropylacrylamide temperature-sensitive material with porphyrin as the core

[0023] The preparation of star polylactic acid (SPPLA-OH) and macromolecular chain transfer agent SPPLA-BSPA with porphyrin as the nucleus terminal hydroxylation is the same as in Example 1.

[0024] Add SPPLA-BSPA (20mg, 0.002mmol), NIPAAm (86.9mg, 0.8mmol) and AIBN (0.2mg, 0.0016mmol) into a 25ml round bottom flask, and then add 0.8ml of THF to fully dissolve them. After evacuating nitrogen three times with a vacuum line, react in a constant temperature oil bath at 70° C. for 12 hours. After the reaction, cool in an ice-water bath, settle in anhydrous ether, centrifuge, take the solid, dissolve it in THF, settle with n-hexane, remove unreacted NIPAAm monomer, and centrifuge to obtain a solid product. Vacuum drying at constant temperature to constant weight yielded 87.9 mg star-shaped polylactic acid-bl...

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Abstract

The invention discloses a method for synthesizing a polylactic acid-block-polyN-isopropyl acrylamide temperature-sensitive material, and belongs to the technical field of amphipathy block copolymers. The method comprises the following steps of: initiating ring-opening polymerization of L-lactide by using tetra(2-hydroxyethyl) phenyl porphyrin to prepare hydroxylated star-shaped polylactic acid taking porphyrin as a core terminal; carrying out esterification reaction on the hydroxylated star-shaped polylactic acid taking porphyrin as the core terminal to obtain a macromolecular chain transfer agent; and preparing a novel star-shaped polylactic acid-block-polyN-isopropyl acrylamide temperature-sensitive material from the macromolecular chain transfer agent and a temperature-sensitive N-isopropyl acrylamide monomer by using a reversible addition-fragmentation chain transfer polymerization method. According to the method, a mild polymerization condition is adopted to facilitate the preparation of the star-shaped polylactic acid-block-polyN-isopropyl acrylamide temperature-sensitive biological material with polyN-isopropyl acrylamide adjustable in length and porphyrin as a core.

Description

technical field [0001] The invention belongs to the technical field of amphiphilic block copolymers, and relates to a synthetic method of poly(lactic acid-block-poly-N-isopropylacrylamide) in the field of chemical engineering, in particular to a star-shaped polymer with porphyrin as the core Synthetic method of polylactic acid-block-poly-N-isopropylacrylamide. Background technique [0002] As we all know, amphiphilic block copolymers can self-assemble into ordered aggregates through affinity-phobic interactions in selective solvents, and have become research hotspots in the fields of drug controlled release, biomaterials, and nanoengineering. In particular, some copolymer materials with stress characteristics (photosensitivity, temperature sensitivity, and pH sensitivity) have broad development prospects in the field of targeted drug delivery as soluble or poorly soluble drugs, and even gene carriers. Poly(N-isopropylacrylamide) (PNIPAAm) and its copolymers have a lower cri...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F293/00C08G63/91C08G63/08A61K47/48A61K41/00A61P35/00
Inventor 戴晓晖王昊王志明潘建明闫永胜
Owner JIANGSU UNIV
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