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CN-121975119-A - Polyamide disulfide compound and preparation method and application thereof

CN121975119ACN 121975119 ACN121975119 ACN 121975119ACN-121975119-A

Abstract

The invention belongs to the technical field of organic chemistry, and particularly discloses a polyamide disulfide compound and a preparation method and application thereof. The structural formula of the polyamide disulfide compound is N is any integer between 2 and 500. The preparation method comprises the steps of mixing sulfur, dichloroacetamide compounds, organic alkali and an organic solvent, performing a first reaction, adding dibromide after the first reaction is finished, and performing a second reaction to obtain the polyamide-based dithioesters. The polymer provided by the invention has high molecular weight, good optical property and excellent mechanical property, can realize mass preparation of polyamide dithioesters, and can realize main chain editing of the polymer through ammonolysis reaction with diamine to obtain the polymonothiooxamide compounds with better thermal and mechanical properties.

Inventors

  • HU RONGRONG
  • TANG BENZHONG
  • HU YANG

Assignees

  • 华南理工大学

Dates

Publication Date
20260505
Application Date
20260325

Claims (9)

  1. 1. The polyamide-based dithioesters compound is characterized by having the following structural formula: ; wherein R 5 is selected from alkyl, 、 Or (b) R 6 is independently selected from H, alkyl or phenyl, R 7 is selected from alkyl, alkoxy, thioether group or aryl, and n is any integer between 2 and 500.
  2. 2. A kind of according to claim 1a polyamide-based disulfide compound, the polyamide disulfide compound is characterized by having the structural formula: 。
  3. 3. The method for preparing the polyamide-based disulfide compound as claimed in any one of claims 1 to 2, which is characterized by comprising the following steps: Mixing sulfur, dichloroacetamide compounds, organic alkali and organic solvent, then carrying out a first reaction, adding dibromide after the first reaction is finished, and carrying out a second reaction to obtain the polyamide-based dithioesters compound.
  4. 4. The method for producing a polyamidodisulfide compound according to claim 3, wherein the dichloroacetamide compound has the structural formula: wherein R 5 is selected from alkyl, 、 Or (b) R 6 is independently selected from H, alkyl or phenyl; The structural formula of the dibromide is as follows: The R 7 is selected from alkyl, alkoxy, thioether or aryl; The organic base comprises one or more of 4-dimethylaminopyridine, triethylamine, N-diisopropylethylamine, 1, 8-diazabicyclo [5.4.0] undec-7-ene, triethylene diamine and triisobutylamine; The organic solvent comprises one or more of dimethyl sulfoxide, N-dimethylformamide, N-dimethylacetamide, pyridine, chloroform, methanol, dichloromethane and tetrahydrofuran.
  5. 5. The method for preparing a polyamidodisulfide compound according to claim 4, wherein the molar ratio of sulfur, dichloroacetamide compound, dibromide and organic base is 1-5:0.5-2:0.5-2:2-10; the molar concentration of the dichloroacetamides compound in the first reaction system is 0.1-2 mol/L.
  6. 6. The method for producing a polyamidodisulfide compound according to any one of claims 3 to 5, wherein the temperature of the first reaction is 0 to 80 ℃ and the time is 0.2 to 24 hours.
  7. 7. The method for producing a polyamide-based disulfide compound according to claim 6, wherein the second reaction is carried out at a temperature of 0 to 60 ℃ for a time of 0.2 to 24 hours.
  8. 8. The use of a polyamidodisulfide compound according to any one of claims 1-2 in the preparation of a polythiooxamide compound.
  9. 9. The use of a polyamidodisulfide compound according to any one of claims 1 to 2 in the preparation of an optical lens.

Description

Polyamide disulfide compound and preparation method and application thereof Technical Field The invention relates to the technical field of organic chemistry, in particular to a polyamide disulfide compound and a preparation method and application thereof. Background The sulfur-containing polymer material has excellent optical performance, dynamic characteristic and unique enrichment capability for heavy metal ions, and is a polymer material with very good development prospect. However, the structure types of sulfur-containing polymers are severely limited by limited synthetic methods. On the other hand, considering that each functional group has its own unique functional characteristics, the new structure of bonding two functional groups will further enrich the functional characteristics of the polymer material, which is rarely embodied in the development of sulfur-containing polymer structures. Therefore, a simple, gentle and efficient polymerization process to synthesize sulfur-containing polymers having various functional motifs is urgently needed. Polythioesters are one of the typical sulfur-containing polymers that have good optical properties, mechanical properties, and degradability characteristics. However, polydithioesters having more sulfur atoms have been rarely reported, mainly by converting polyesters to polydithioesters using Lawson's reagent, or by first forming a salt of the disulfide with benzyl chloride and elemental sulfur followed by nucleophilic substitution with bromide. Meanwhile, elemental sulfur, which is a byproduct in petroleum refining, has the characteristics of stability, low toxicity, low cost and the like, and has been widely used for preparing sulfur-containing polymers such as polythioamide, polythiourea, polythiophene and the like. Therefore, how to provide an economic and efficient preparation method, which directly converts elemental sulfur into polydithioester and introduces other functional elements into the polymer to enrich the structural library of sulfur-containing polymer, is a problem to be solved in the art. In addition, polymer backbone editing has become one of the methods of adjusting the lifecycle of polymer materials. Therefore, enriching the structure of sulfur-containing polymers and adjusting the life cycle of materials by using a main chain editing strategy is also a problem to be solved urgently by those skilled in the art. Disclosure of Invention In view of the above, the present invention provides a polyamide disulfide compound, a preparation method and an application thereof, so as to solve the problem of limited synthesis method and types of sulfur-containing polymers. In order to achieve the above purpose, the invention adopts the following technical scheme: polyamide-based diamine a thioester-type compound, wherein the sulfur-containing compound, the structural formula of the amido dithioesters compound is as follows: ; wherein R 5 is selected from alkyl, 、Or (b)R 6 is independently selected from H, alkyl or phenyl, R 7 is selected from alkyl, alkoxy, thioether group or aryl, and n is any integer between 2 and 500. Preferably, the structural formula of the polyamide-based disulfide compound is as follows: 。 Another object of the present invention is to provide a method for preparing a polyamidodisulfide compound, comprising the steps of: Mixing sulfur, dichloroacetamide compounds, organic alkali and organic solvent, then carrying out a first reaction, adding dibromide after the first reaction is finished, and carrying out a second reaction to obtain the polyamide-based dithioesters compound. Preferably, the structural formula of the dichloroacetamides compound is as follows: wherein R 5 is selected from alkyl, 、Or (b)R 6 is independently selected from H, alkyl or phenyl; The structural formula of the dibromide is as follows: The R 7 is selected from alkyl, alkoxy, thioether or aryl; The organic base comprises one or more of 4-dimethylaminopyridine, triethylamine, N-diisopropylethylamine, 1, 8-diazabicyclo [5.4.0] undec-7-ene, triethylene diamine and triisobutylamine; The organic solvent comprises one or more of dimethyl sulfoxide, N-dimethylformamide, N-dimethylacetamide, pyridine, chloroform, methanol, dichloromethane and tetrahydrofuran. Preferably, the molar ratio of the sulfur, the dichloroacetamide compound, the dibromide and the organic base is 1-5:0.5-2:0.5-2:2-10; the molar concentration of the dichloroacetamides compound in the first reaction system is 0.1-2 mol/L. Preferably, the temperature of the first reaction is 0-80 ℃ and the time is 0.2-24 hours. Preferably, the temperature of the second reaction is 0-60 ℃ and the time is 0.2-24 h. Still another object of the present invention is to provide an application of a polyamidodithioesters compound in preparing a monothiooxamide compound. Still another object of the present invention is to provide an application of a polyamidodisulfide compound in the preparation of an optical lens. Com