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Method for preparing hydrogel material based on 1,4-cyclohexane/phthalic acid

A technology of phthalic acid and cyclohexane, which is applied in the field of preparation of hydrogel materials, can solve the problems of difficult preparation of hydrogels, harsh and complex synthesis conditions, etc., and achieve good biocompatibility and rapid gelation , good water absorption effect

Inactive Publication Date: 2010-10-20
SHANGHAI JIAO TONG UNIV
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  • Abstract
  • Description
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  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the harsh and complex synthetic conditions of this type of gel system, and the selectivity of gel formation only in response to enzymes, it is not easy to prepare hydrogels
Therefore, there are also great limitations in future applications.

Method used

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  • Method for preparing hydrogel material based on 1,4-cyclohexane/phthalic acid
  • Method for preparing hydrogel material based on 1,4-cyclohexane/phthalic acid
  • Method for preparing hydrogel material based on 1,4-cyclohexane/phthalic acid

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0037] SDiAcNHPhCOCH 2 CH 2 Synthesis of OH

[0038] a) Synthesis of 1,4-cyclohexanedicarboxylic acid chloride SDiAcCl

[0039] 1,4-cyclohexanedicarboxylic acid (4.0 g, 20 mmol) and SOCL 2 (12ml) mixed in a flask. Heated to reflux for 6 hours to obtain a yellow transparent solution. Rotary evaporation to remove residual SOCl 2 , to obtain an oil, and then placed in the refrigerator (-4 ° C) to obtain a pale yellow solid sample.

[0040] b) Synthesis of SDiAcNHPhCOMe

[0041]

[0042] At 0 °C, SDiAcCl (4 mmol) in anhydrous CH 2 Cl 2 solution was added to HCl.NH 2 -L-Ph-OMe(9mmol) and Et 3 N (3ml) in 30ml anhydrous CH 2 Cl 2 solution. The reaction was allowed to warm slowly to room temperature and stirred for 6 hours. The resulting precipitate was collected by vacuum filtration and washed with ethanol. Yield (46%). 1 H-NMR (DMSO): δ1.32(m.4H); δ1.78(m.4H); δ2.17(s.2H); δ2.71(d.2H); δ2.88(d.2H ); δ3.62 (s.6H); δ4.41 (s.2H); δ7.22 (m.Ph, 10H), δ7.96 (s.2H).

...

example 2

[0050] Synthesis of SDiAcNHPhCOhistamine

[0051]

[0052] 1-Hydroxybenzotriazole monohydrate (HOBT) (Mw 135, 1.32 mmol, 2.2 times) and SDiAcNHPhCOOH (0.6 mmol) were dissolved in 5 ml of DMSO solution at room temperature. Dissolve 1,1'-carbonyldiimidazole CDI (Mw 162, 1.32 mmol, 2.2 times) in 1 ml DMSO, and then add dropwise to the above solution. Then stir for 2 hours.

[0053] Histamine (1.32 mmol, 2.2 times) was dissolved in 1 ml DMSO, then added dropwise to the above mixed solution and stirred at room temperature for 24 hours. After the reaction was completed, the reaction mixture was poured into 20 ml of water, filtered to obtain the precipitated part, and then washed with water and methanol respectively. The precipitated fraction was collected and dried in vacuo. A pale yellow solid powder was obtained with a yield of 75%. 1 H-NMR (DMSO): δ1.36(m.4H); δ1.75(m.4H); δ2.13(s.2H); δ2.75(d.2H); δ2.68(d.2H ); δ4.54 (s.2H); δ6.89 (s.2H); δ7.12 (m.Ph, 10H); δ7.44 (s.2H);...

example 3

[0055] Synthesis of SDiAcNHSCOLysine

[0056] a) Synthesis of SDiAcNHSCOMe

[0057]

[0058] At 0 °C, SDiAcCl (4 mmol) in anhydrous CH 2 Cl 2 solution was added to HCl.NH 2 -L-Methine-OMe (9mmol) and Et 3 N (3ml) in 30ml anhydrous CH 2 Cl 2 solution. The reaction was allowed to warm slowly to room temperature and stirred for 6 hours. The resulting precipitate was collected by vacuum filtration and washed with ethanol. Yield (80%). 1 H-NMR (DMSO): δ1.37(m.4H); δ1.72(m.4H); δ2.03(m, 10H, SCH 3 +CH 2 ); δ2.61(m, 4H, SCH 2 );δ2.23(s.4H);δ2.72(d.2H);δ2.78(d.2H);δ3.62(s.6H);δ4.56(s.2H)δ8.10( s.2H).

[0059] b) Synthesis of SDiAcNHSCOOH

[0060]

[0061] SDiAcNHSCOMe (0.6 mmol) was added to MeOH (10 ml) and 2M NaOH at 0°C. The reaction mixture was slowly warmed to room temperature and stirred for 4 hours. Dilute with water and adjust the pH of the solution to less than 4 with 6M HCl. The resulting precipitate is collected and dried in vacuo. Yield 81%.

[0062...

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Abstract

A method for preparing a hydrogel material based on 1,4-cyclohexane / phthalic acid belongs to the technical field of hydrogel materials and comprises the following steps: (1) the 1,4-cyclohexane / phthalic acid SDiAc carries out chlorination reaction with sulfoxide chloride SOCl2 to generate SDiAcCl; (2) 1 part of SDiAcCl prepared in the step (1) is taken to carry out amidation reaction with 2.2 parts of amino acid (NH2RCOCH3) under methyl protection to generate SDiAcNHRCOCH3 and then methyl protection is removed to generate SDiAcNHRCOOH; and (3) 1 part of SDiAcNHRCOOH prepared in the step (2) is taken to carry out acylation reaction with 2.2 parts of compound molecules containing amino groups or hydroxyl groups (Y) to generate the hydrogel material SDiAcNHRCOY. The preparation method is simple and convenient, and the obtained hydrogel has good biocompatibility and is degradable.

Description

technical field [0001] The invention relates to a preparation method in the technical field of hydrogel materials, in particular to a preparation method of hydrogel materials based on 1,4-cyclohexane / phthalic acid. Background technique [0002] The application of new hydrogel materials with different structures and properties in cell tissue culture has aroused great interest. Currently, tissue engineering hydrogels are mainly divided into two categories: natural hydrogels and synthetic polymer hydrogels. However, natural biomaterials have problems such as low mechanical strength, pathogen transmission, and the difficulty of preparing polymers into hydrogels, which limit the application of these materials in the field of cell tissue engineering in the future. [0003] The use of low molecular weight compounds and water to form nanofiber hydrogels has made some progress in solving the above problems, which is of particular significance for the study of cell tissue culture. T...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/63C07C231/12C07D233/64
Inventor 冯传良张荻
Owner SHANGHAI JIAO TONG UNIV
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