Poly (hydroxyl) p-phenylene benzimidazole-benzoxazole PBIO liquid crystal copolymer and monomer, preparation and application thereof

A technology of benzodiimidazole and benzoxazole, which is applied in the preparation of amino compounds, organic compounds, carboxylates, etc., can solve the problems of difficult processing into fibers, complicated process, and complicated process, and achieves a solution The effect of strong equipment capacity, improved heat resistance and good spinnability

Inactive Publication Date: 2019-05-17
金宁人 +3
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] 1) The process of manufacturing ABAA is complicated, the production capacity is low, and the expansion of application is limited due to high price
[0014] Due to the long preparation process and complicated process, the price of AB-type monomer is relatively high, and the price reduction of the prepared PBO fiber is not large, and it is difficult to reach 1800 yuan / kg or below: it can only be used for special occasions of national defense and military industry, especially for It is more suitable for the preparation of co-condensation composite fibers that need to ensure the integrity of PBO chain links, and cannot meet the urgent needs of cost-effective expansion applications in industrial and civil fields
[0015] 2) The lack and improvement of compounding, light resistance and compression performance caused by the molecular structure of PBO itself
[0022] Although the price of PDBI has been greatly reduced to 80% of PBO fiber, its initial decomposition temperature is 470°C, and the temperature at 10% weight loss is only 508.3°C; and the spinnability of the liquid crystal stock solution is not good, and it is difficult to process into fibers Larger, and the liquid crystal stock solution has strong adhesion (including with stainless steel equipment), it is very difficult to clean the kettle

Method used

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  • Poly (hydroxyl) p-phenylene benzimidazole-benzoxazole PBIO liquid crystal copolymer and monomer, preparation and application thereof
  • Poly (hydroxyl) p-phenylene benzimidazole-benzoxazole PBIO liquid crystal copolymer and monomer, preparation and application thereof
  • Poly (hydroxyl) p-phenylene benzimidazole-benzoxazole PBIO liquid crystal copolymer and monomer, preparation and application thereof

Examples

Experimental program
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preparation example Construction

[0081] The preparation of embodiment 1 formula II compound salt monomer

[0082] (1) Preparation of compound salt monomer DHTAB (1,2,4,5-tetraaminobenzene of 2,5-dihydroxyterephthalic acid)

[0083]

[0084] Add 200g deoxygenated water, 10.697g Na 2 CO 3 (0.1009mol) and 9.98g (0.0504mol) of 2,5-dihydroxyterephthalic acid (DHTA), stirred and heated to 70 ° C to be dissolved into a light brown transparent solution, under the protection of nitrogen, add 14.34g (0.0505 mol) 1,2,4,5-tetraaminobenzene hydrochloride (TABH), after the addition is completed, stir at 70-80°C for 15 minutes, then slowly cool to room temperature, filter, and wash the wet filter cake with 30mL deoxygenated water, and filter to dryness , and vacuum-dried at 70°C to obtain 15.43 g (0.0459 mol) of 1,2,4,5-tetraaminobenzene compound salt (DHTAB) of 2,5-dihydroxyterephthalic acid, with a yield of 91.09% based on DHTA. FT-IR (KBr) see attached Figure 1-a .

[0085] (2) Preparation of compound salt monome...

Embodiment 2

[0091] Example 2 DH-PBIO 4 (poly2,5-dihydroxy-p-phenylenebenzodiimidazole-2,5-benzoxazole) and its monofilament fiber

[0092]

[0093] Sequentially add P into the glass polymerization reaction column 2 o 5 Mass concentration is 85.3% polyphosphoric acid (PPA) 18.0g and P 2 o 5 3.40g, turn on the spiral stirring, and raise the temperature to 100°C and control the speed of 350r / min to stir for 30min and wait for P 2 o 5 After the reaction dissolves, pass N 2 Slowly add 2.69g of DHTAB and 2.45g of AHBA (mol ratio 1:2, mass ratio 0.523:0.477) in sequence under protection for 3 minutes, after adding, slowly rise to 152°C with stirring for 20 minutes and yellow-green fluorescence appears, keep warm at 152-155°C React for 10 minutes to golden yellow liquid crystal filaments, then stir and polymerize at 156-165°C for 30 minutes until bronze filaments are formed. When the speed drops significantly to 200r / min or below, the polymerization reaction is over, and the stirring is ...

Embodiment 3

[0110] Example 3 DH-PBIO 3 (poly2,5-dihydroxy-p-phenylenebenzodiimidazole-2,6-benzoxazole) and its monofilament fiber

[0111]

[0112] Sequentially add P into the glass polymerization reaction column 2 o 5 Mass concentration is 85.3% polyphosphoric acid (PPA) 18.0g and P 2 o 5 3.40g, turn on the spiral stirring, and raise the temperature to 100°C and control the speed of 350r / min to stir for 30min and wait for P 2 o 5 After the reaction dissolves, pass N 2 Slowly add 2.69g of DHTAB and 2.45g of HABA (mol ratio 1:2, mass ratio 0.523:0.477) successively under protection for 3 minutes, after adding, slowly rise to 152°C with stirring for 20 minutes and yellow-green fluorescence appears, keep warm at 152-155°C React for 10 minutes to golden yellow liquid crystal filaments, then stir and polymerize at 156-165°C for 30 minutes until bronze filaments are formed. When the speed drops significantly to 200r / min or below, the polymerization reaction is over, and the stirring is...

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Abstract

The invention discloses a poly (hydroxyl) p-phenylene benzimidazole-benzoxazole PBIO liquid crystal copolymer and monomer, preparation and application thereof. The invention provides a compound salt monomer (II), wherein k is equal to 0, 1 or 2; and the compound salt monomer has certain antioxidant performance. The compound salt monomer is prepared by compound reaction of BB type monomer hydrochloride (IV) and AA type monomer (V), and is economical and convenient. According to the poly (hydroxyl) p-phenylene benzimidazole-benzoxazole PBIO liquid crystal copolymer (I), wherein m/n=2. The PBIO liquid crystal copolymer is prepared by taking a AB type monomer (III) and the compound salt monomer (II) as raw materials through a copolycondensation reaction, no corrosive gas is generated in the process, the polymerization speed is high, the production capacity is high, and the implementation is convenient. The PBIO liquid crystal copolymer has good spinnability and heat resistance, and can beused for preparing PBIO alloy fibers with good light resistance, heat resistance and composite compression resistance. (Please see the specification for the formula).

Description

technical field [0001] The invention relates to a kind of poly(hydroxyl) p-phenylene benzodiimidazole-benzoxazole PBIO liquid crystal copolymer and its monomer, preparation and application. Background technique [0002] Since 1998, PBO fiber has been exclusively produced by Toyobo Corporation of Japan according to formula (1) polycondensation and spinning monopoly (trade name Zylon), and has imposed a technical blockade and product ban on China. It is mainly sold to Europe, America and Japan as military supplies, and the price is as high as 3000 yuan / kg. [0003] [0004] Due to the difficulty in the source of the monomer 4,6-diaminoresorcinol hydrochloride (DARH), the HCl removal time of the process of formula (1)>30h, and the complicated semi-continuous polymerization operation, the industrialization process is extremely difficult. Although Toyobo also adopts the patented technology of making compound salt TDH first and then preparing PBO fiber by self-condensation,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/00C07C211/50C07C51/41C07C63/28C07C65/05C08G73/06D01F6/78
Inventor 金宁人陈汉庚金菁张建庭
Owner 金宁人
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