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Poly-p-phenylene ethene diamine/hexamethylene diamine copolymer and preparation method thereof

A technology of polyethylene terephthalamide and ethylene phthalamide is applied in the field of polyethylene terephthalamide/hexamethylene diamine copolymer and its preparation, and can solve the problems of prepolymerization and solidification. Phase polycondensation has problems such as high equipment requirements, high ionic liquid cost, and complex synthesis process, so as to achieve the effects of low monomer ratio requirements, high product yield and high melting point

Inactive Publication Date: 2010-05-19
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] U.S. Patent US2002183479A1 reported that a prepolymer was generated under high temperature and high pressure with butylenediamine terephthalate, hexamethylenediamine terephthalate and water, and then solid-phase polycondensation was carried out under high temperature and vacuum to form polyterephthalene Formamide butanediamine / hexamethylenediamine copolymer (PA4T / 6T), the melting point of this polymer is higher than 300°C, but the cost of raw material 1,4-butanediamine is high, the source is small, and prepolymerization and solid-state polycondensation High requirements for equipment
U.S. Patent No. 4,072,664A has reported that 1,2-ethylenediamine reacts with p-nitrobenzoyl chloride to obtain a dinitro compound, and through a reduction reaction, the aromatic diamine containing ethylenediamine structure is obtained, and is mixed with p-nitrobenzoyl chloride in different proportions. Amines are mixed, and then reacted with terephthaloyl chloride to prepare terephthalamide p-phenylene diamine copolymers. The fibers of this polymer have good mechanical properties, but the synthesis process is complicated and the cost is high
Chang Jing and Feng Lianfang from Zhejiang University obtained high-viscosity PA6T by polycondensation of hexamethylenediamine terephthalate in ionic liquids, but the cost of ionic liquids was high and the effect became poor after recycling

Method used

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  • Poly-p-phenylene ethene diamine/hexamethylene diamine copolymer and preparation method thereof
  • Poly-p-phenylene ethene diamine/hexamethylene diamine copolymer and preparation method thereof
  • Poly-p-phenylene ethene diamine/hexamethylene diamine copolymer and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0045] Example 1, 20.3g terephthaloyl chloride and 2g N, N-dimethylformamide were dissolved in 200g hexane to form acid chloride solution; 3.0g 1,2-ethylenediamine, 5.8g 1,6- Hexamethylenediamine, 10.6g sodium carbonate and 200g deionized water are added in the reactor that has stirrer, thermometer and reflux condenser, solid is dissolved completely; Slowly add to the reactor, and then stir for 1 hour; add 200g deionized water, distill and recover the solvent at a temperature of 60-90°C; centrifuge the reaction mixture, concentrate and crystallize the liquid to obtain the by-product salt, and wash the solid , purified with acetone, and dried to obtain polyethylene terephthalamide / hexamethylenediamine copolymer, with a yield of 85%, and intrinsic viscosity [η]=0.64dL·g -1 .

Embodiment 2

[0046]Example 2, 20.3g terephthaloyl chloride and 20g N,N-dimethylacetamide were dissolved in 600g pentane to form acid chloride solution; 0.3g 1,2-ethylenediamine, 11.02g 1,6- Hexamethylenediamine, 13.8g salt of wormwood and 500g deionized water are added in the reactor that has stirrer, thermometer and reflux condenser, solid is dissolved completely; Slowly add it to the reactor, and then stir for 2 hours; add 600g deionized water, distill and recover the solvent at a temperature of 30-60°C; centrifuge the reaction mixture, concentrate and crystallize the liquid to obtain the by-product salt, and wash the solid , purified with acetone, and dried to obtain polyethylene terephthalamide / hexamethylenediamine copolymer, with a yield of 91%, and intrinsic viscosity [η]=0.38dL·g -1 .

Embodiment 3

[0047] Example 3, 20.3g terephthaloyl chloride and 1g dimethyl sulfoxide were dissolved in 100g methylene chloride to form an acid chloride solution; 1.2g 1,2-ethylenediamine, 9.28g 1,6-hexanediamine , 8g of sodium hydroxide and 100g of deionized water were added to a reactor with a stirrer, a thermometer and a reflux condenser to completely dissolve the solid; under cooling in a cold water bath, slowly add the above prepared acid chloride solution within 0.5 hours Add 100g of deionized water, distill and recover the solvent at a temperature of 30-60°C; centrifuge the reaction mixture, concentrate and crystallize the liquid to obtain the by-product salt, wash the solid and purify it with acetone , dry, obtain polyethylene terephthalamide / hexamethylenediamine copolymer, yield 83%, intrinsic viscosity number [η]=0.58dL·g -1 .

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Abstract

The invention relates to a poly-p-phenylene ethene diamine / hexamethylene diamine copolymer and a preparation method thereof, which is characterized by comprising the following steps of: dissolving 20.3 parts of paraphthaloyl chloride and 1-30 parts of auxiliary agent in 100-1000 parts of organic solvent to prepare into acyl chloride solution; adding 0.3-5.7 parts of 1,2- ethene diamine, 0.58-11.02 parts of 1,6-ethene diamine, 8-13.8 parts of alkaline compound and 800-1200 parts of deionized water into a reactor with a stirrer, a thermometer and a reflux condenser to be completely dissolved; under the cooling of a cooling bath, adding the prepared acyl chloride solution slowly into the reactor within 0.5-2 hours and then stirring and reacting for 1-3 hours; adding 100-1000 parts of deionized water; distilling and recycling solvent at the 30-90 DEG C; centrifugating and separating reactive mixture; concentrating and crystallizing the liquid to obtain by-product salt; washing ,purifying by using acetone and drying the solid to obtain the poly-p-phenylene ethene diamine / hexamethylene diamine copolymer. The intrinsic viscosity[Eta]of the copolymer is equal to 0.30-0.80dL*g-1, the melting point Tm is 340-380 DEG C, and the initial thermal decomposition temperature Td is 390-440 DEG C.

Description

technical field [0001] The invention relates to a polyethylene terephthalamide / hexamethylene diamine copolymer and a preparation method thereof, belonging to the field of polymer synthesis. Background technique [0002] Semi-aromatic polyamides with aryl and aliphatic chains in the molecular main chain have both excellent heat resistance and processing properties, and are a class of engineering plastics with excellent performance. In the series of semi-aromatic polyamides synthesized from terephthalic acid and its derivatives and aliphatic diamines, as the number of carbon atoms in the diamine molecules decreases, the thermal properties of the polymers improve, but the processability becomes worse. Polyhexamethylene terephthalamide (PA6T) and polynonanediamine terephthalamide (PA9T) can be melt-processed, with a melting point higher than 300°C, and polyethylene terephthalamide (PA2T) and polyparaphthalamide Butylenediamide phthalamide (PA4T) cannot be melt processed. Among...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G69/26C08G69/28C08G69/46
Inventor 杨杰张美林龙盛如牛鹏飞张刚王孝军
Owner SICHUAN UNIV