Bisphenol A type poly sulfuric acid (ammonia) ester compound and synthetic method thereof

A technology of ester compounds and synthesis methods, applied in the field of polysulfate (ammonia) ester compounds, new type bisphenol A type polysulfate (ammonia) ester compounds and their synthesis, can solve difficult and no substantive basic reactions Break through and restrict the development and application of polyester materials, and achieve the effects of low environmental pollution, excellent mechanical properties, and good alkali resistance

Active Publication Date: 2014-09-24
内蒙古图微新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In addition, due to the inherent difficulty in developing new basic polymerization reactions, polyester has been developed for decades, but so far there has been no substantial breakthrough in basic reactions, which fundamentally limits the development and application of polyester materials.

Method used

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  • Bisphenol A type poly sulfuric acid (ammonia) ester compound and synthetic method thereof
  • Bisphenol A type poly sulfuric acid (ammonia) ester compound and synthetic method thereof
  • Bisphenol A type poly sulfuric acid (ammonia) ester compound and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Example 1、 Bisphenol A type polysulfate -1 with a degree of polymerization of 10~50 ( PSE-1 )Synthesis

[0044] (1) Synthesis of bisphenol A dioxysulfonyl fluoride: Dissolve 22.8 kg (100 mol) of bisphenol A (scientific name: 2,2-bis(4-hydroxyphenyl)propane) in 5 L of dichloromethane or chloroform Add 10.1 kg (100 mol) of triethylamine, and then carefully and continuously introduce sulfonyl fluoride gas. React at 25°C for 12 hours. After the reaction is complete, simply concentrate and filter to obtain 2,2-bis(4-oxysulfonyl fluorophenyl) propane as a white solid product of dioxysulfonyl fluoride (English) The full name is 4,4'-(propane-2,2-diyl)bis(4,1-phenylene) disulfofluoridate]) 38.5 kg, yield: 98%.

[0045] NMR analysis data of the synthesized product: 1 H NMR (300 MHz, CDCl 3 ): δ 7.24-7.32(m, 8 H), 1.70 (s, 6 H); 13 C NMR (75 MHz, CDCl 3 ): 150.4, 148.2, 128.7, 120.6, 42.9, 30.7; 19 F NMR (282 MHz, CDCl 3 ): δ +37.47;

[0046] High resolution mass spectrometry da...

Embodiment 2

[0058] Example 2 、 Bisphenol A polysulfate -1 with a degree of polymerization of 10~50 ( PSE-1 ) Solvent-free synthesis

[0059] (1) Synthesis of bisphenol A dioxysulfonyl fluoride: the same as in Example 1.

[0060] (2) Bisphenol A polysulfate -1 ( PSE-1 ) Synthesis: Under the protection of nitrogen, dissolve 3.92 kg (10 mol) of the synthesized bisphenol A dioxysulfonyl fluoride in an equal molar amount of trimethylsilyl protected bisphenol 3.73 kg (10 mol) liquid , Add 10% molar amount (1.0 mol) of the catalyst 1,8-diazabicyclo(5.4.0)undec-7-ene ( DBU ), react for 6 hours under mechanical stirring at 50°C, add water to the mixture to terminate the reaction, separate the precipitated polymer product, extract with ethanol and dry to obtain 5.31 g of bisphenol A polysulfate as a white solid, with a yield of 69 %. The infrared spectrum of the polymer is shown in Figure 1. The performance indicators of the polymerization product are as follows:

[0061] Weight average molecular we...

Embodiment 3

[0067] Example 3、 Bisphenol A type polysulfate-2 with a degree of polymerization of 200~300 ( PSE-2 )Synthesis

[0068] (1) Synthesis of bisphenol A dioxysulfonyl fluoride: the same as in Example 1.

[0069] (2) The degree of polymerization is 200~300 bisphenol A type polysulfate-1 ( PSE-2 )Synthesis

[0070] Under the protection of nitrogen, dissolve 3.92 kg (10 mol) of bisphenol A dioxysulfonyl fluoride prepared in step (1) and 3.73 kg (10 mol) of trimethylsilyl-protected bisphenol in 500 mL of N- Methylpyrrolidone ( NMP ), add 10% molar (1.0 mol) of catalyst DBU (1,8-diazabicyclo(5.4.0)undec-7-ene), react for 12 hours under mechanical stirring at 25℃, then pour the mixture into water to terminate the reaction, separate the precipitated polymer product, and extract it with ethanol After extraction and drying, 6.38 g of white solid bisphenol A polysulfate was obtained with a yield of 83%. Figure 2 shows the infrared spectrum of the polymer. The performance indicators of the p...

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Abstract

The present invention discloses a bisphenol A type poly sulfuric acid (ammonia) ester compound, and belongs to the technical field of polymers. The bisphenol A type poly sulfuric acid (ammonia) ester compound is prepared as follows: using bisphenol A dioxygen sulfonyl fluoride as a raw material for reacting with trialkyl silicon group-protected bisphenol or diamine in the presence of an inert gas for protection and a catalyst at 30-120 DEG C for 3 to 36 hours; and pouring the reaction mixture into water to precipitate a polymerization product, namely the bisphenol A type poly sulfuric acid (ammonia) ester compound. The bisphenol A type poly sulfuric acid (ammonia) ester compound has excellent mechanical properties, dielectric properties, tolerance and wear resistance, and has broad application prospects in aerospace, electronic communications, electromechanical and microelectronic industries. In addition, the high reaction activity bisphenol A type dioxygen sulfonyl fluoride compound is used as a polyester synthetic raw material, and compared with a traditional polyester process, the reaction condition is mild and easy to control, the reaction process is simple and easy to operate; the after treatment process is simple, the environmental pollution is less, and the bisphenol A type poly sulfuric acid (ammonia) ester compound is favorable to industrial production.

Description

technical field [0001] The invention belongs to the technical field of polymer materials, and relates to a polysulfate (ammonia) ester compound, in particular to a novel bisphenol A polysulfate (ammonia) ester compound and a synthesis method thereof. Background technique [0002] Polyester is an important chemical synthetic material, widely used in fiber, packaging, engineering plastics, medical materials and other fields. Driven by technological progress and market demand, the global polyester industry has developed rapidly in the past 20 years. Compared with other polymer synthetic materials, polyester has the advantages of low energy consumption, less pollution, simple synthesis route, and recyclable products. Polycarbonate PC is a kind of high molecular polyester material containing carbonate groups in the molecular chain. Since the German Bayer company first successfully researched PC in 1953 and realized industrial production in 1958, polycarbonate and its derivative ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G75/00
Inventor 陈元文朱金城王惠荣
Owner 内蒙古图微新材料科技有限公司
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