Polythioetherimide and preparation method thereof

A technology of polythioetherimide and phthalimide, which is applied in the field of preparation of new polythioetherimide, which can solve the problem of difficulty in controlling the equimolar equivalent of dichloromonomers and the easy oxidation and deliquescence of anhydrous alkali metal sulfides , high requirements for preparation conditions, etc., to achieve the effects of saving preparation costs, simple and easy operation and production, and reasonable and practical technology

Inactive Publication Date: 2009-09-16
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the preparation conditions of the anhydrous alkali metal sulfide used in the coupling polymerization reaction with dichlorophthalimide are very demanding, and the anhydrous alkali metal sulfide is easy to oxidize and deliquescence, and the equimolar amount of the dichloromonomer during the reaction The equivalent is difficult to control, so it is necessary to further optimize the preparation conditions and find a simple and stable preparation process for large-scale industrial production

Method used

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  • Polythioetherimide and preparation method thereof
  • Polythioetherimide and preparation method thereof
  • Polythioetherimide and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Add 32.86g (0.18mol) 4-chlorophthalic anhydride, 3.65g (0.02mol) 3-chlorophthalic anhydride, 400mL glacial acetic acid into a dry and clean 1L three-necked flask, stir to dissolve and add 19.83g (0.1mol) 4,4 '-Diaminodiphenylmethane, heated to 140°C for reflux reaction for 24 hours, cooled to room temperature and filtered the obtained filter cake, washed three times with distilled water, and vacuum-dried at 120°C to obtain 48.52g of crude product of dichlorophthalimide, yield 92%. The crude product was recrystallized from a mixed solvent of toluene and N,N-dimethylacetamide (4:1, v / v) and used for the next step of polymerization. Under an argon atmosphere, add 7.9107g (0.015mol) of the above dichloromonomer, 0.4800g (0.015mol) of sulfur, 1.3241g (0.035mol) of sodium borohydride, 1.7954g (0.032mol) of hydrogen hydride into a dry and clean 500mL three-necked flask Potassium oxide, 0.4439g (0.004mol) calcium chloride and 150mL N,N-dimethylacetamide, stirred and heated to ...

Embodiment 2

[0036] Add 91.28g (0.50mol) 4-chlorophthalic anhydride, 91.28g (0.50mol) 3-chlorophthalic anhydride, 100.12g (0.5mol) 4,4'-diaminodiphenyl ether into a dry and clean 500mL three-necked flask, Slowly heated up to 260°C under vacuum to form a homogeneous melt, stirred and reacted for 4 hours, and then cooled to room temperature to obtain 259.38 g of crude bischlorophthalimide, with a yield of 98%. The crude product can be directly used in the next polymerization reaction. In a dry and clean 500mL three-necked flask, add 10.5872g (0.020mol) of the above dichloro monomer, 0.6602g (0.0206mol) of sulfur, 0.9600g (0.04mol) of sodium hydride, 2.8471g (0.0206mol) of potassium carbonate, 0.2120g ( 0.005mol) lithium chloride and 180mL N-methylpyrrolidone, stirred and heated to 80°C for 24 hours, then added 0.3092g (0.0012mol) N-phenyl-3-chlorophthalimide and reacted for 4 hours After cooling to room temperature, the reaction solution was slowly poured into 2L distilled water and stirred...

Embodiment 3

[0038] Add 109.54g (0.60mol) 4-chlorophthalic anhydride, 36.51g (0.20mol) 3-chlorophthalic anhydride, 1600mL glacial acetic acid into a dry and clean 3L three-necked flask, stir to dissolve and add 90.53g (0.40mol) 3,3 '-Dimethyl-4,4'-diaminodiphenylmethane, heat up to 130°C and reflux for 30 hours, cool to room temperature, pour it into 6L distilled water and stir for 3 hours, filter the filter cake and wash it with distilled water Three times, vacuum drying at 120° C. yielded 208.84 g of a crude product of dichlorophthalimide, with a yield of 94%. The crude product was recrystallized from dimethyl sulfoxide and used in the next polymerization reaction. Under a nitrogen atmosphere, add 2.7772g (0.005mol) of the above-mentioned dichloromonomer, 0.1600g (0.005mol) of sulfur, 0.4504g (0.005mol) of paraformaldehyde, 0.5299g (0.005mol) of carbonic acid into a dry and clean 100mL three-necked flask Sodium, 0.0530g (0.0012mol) lithium chloride, 50mL hexamethylphosphoric triamide, s...

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Abstract

The invention relates to polythioetherimide and a preparation method thereof. The method is characterized by comprising the following steps: mono-substituted phthalic anhydride isomer with structural formula II is adopted as a reaction material to react with organic diamine NH2RNH2 with half mol equivalent weight at the temperature of about 100 DEG C to about 350 DEG C to generate binary-substituted phthalimide; then binary-substituted phthalimide and sulfur with about equimolar equivalent weight are subjected to coupling polymerization reaction at the temperature of about 60 DEG C to about 260 DEG C under the existence of reducing agent, catalyst and reaction auxiliary agent to generate polythioetherimide resin with structural formula I; and the molecular weight of the resin can be adjusted by end capping agent. The preparation method can greatly reduce the preparation cost and reaction steps, the whole process is more reasonable and practical, and the obtained resin has superior comprehensive properties such as good heat resistance, mechanical properties, melting processing property and the like, can be widely applied in the related fields such as high-temperature resistant engineering plastics, films, adhesives, enameled wires, foamed plastics, fiber, advanced composite materials and the like; in the structural formula II, A substituent is chlorine atom or nitro at 3-bit or 4-bit; and in the structural formula I, R is substituted or unsubstituted organic group.

Description

technical field [0001] The invention belongs to the technical field of polythioetherimide and related preparation methods, and in particular relates to a novel polythioetherimide prepared by using chlorinated phthalic anhydride or nitrophthalic anhydride isomers as raw materials and using sulfur as a coupling agent amine method. Background technique [0002] Polythioetherimide is usually prepared by reacting thioether-containing aromatic tetra-acid dianhydride with aliphatic or aromatic diamine. Since the flexible unit of thioether bond is introduced into the rigid polyimide main chain, this type of polymer In addition to good thermomechanical properties, it also has the characteristics of good solubility, low melt viscosity and melt processability. It is a very promising thermoplastic heat-resistant polymer material. Therefore, the synthesis of diphenyl sulfide-type tetra-acid dianhydrides and corresponding polythioetherimides has attracted people's attention very early. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/10C08G75/02C08G75/0222C08G75/0263
Inventor 方省众胡本林严庆丁孟贤
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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