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Application of novel isovanillin epoxy resin monomer in preparation of silicon-containing polymer

A silicon polymer, isovanillin technology, applied in organic chemistry and other directions, can solve the problem of unreported monomer structure research, and achieve the effects of low curing processing temperature, wide source and good biological safety.

Active Publication Date: 2022-05-10
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It can be seen that epoxy resin material monomers based on bio-based sources are gradually being developed at this stage, but there are basically no reports on the construction of new monomer structures based on bio-based isovanillin

Method used

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  • Application of novel isovanillin epoxy resin monomer in preparation of silicon-containing polymer
  • Application of novel isovanillin epoxy resin monomer in preparation of silicon-containing polymer
  • Application of novel isovanillin epoxy resin monomer in preparation of silicon-containing polymer

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Experimental program
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Effect test

Embodiment 1

[0050] The preparation of embodiment 1 intermediate B

[0051] Add sodium hydroxide (32.17g) and potassium hydroxide (48.25g) and 16mL of deionized water to a 500mL single-necked bottle in sequence, heat to 160°C within 10min, then add isovanillin (96.5g, 0.635 mol). After reacting the obtained reaction system at 160°C for 4 hours, slowly add water, dissolve it in a beaker, and then lower it to room temperature, then acidify it with phosphoric acid to adjust the pH=2, filter and wash the obtained precipitate, and finally dry the obtained solid. 92 g of product intermediate B was obtained with a yield of 86.2%.

[0052] 1 H NMR(400MHz,DMSO)δ12.50(s,1H),9.39(s,1H),7.41(dd,J=8.4,2.0Hz,1H),7.35(d,J=2.0Hz,1H),6.99 (d,J=8.5Hz,1H),3.82(s,3H).

Embodiment 2

[0053] The preparation of embodiment 2 isovanillin bio-based epoxy resin monomer

[0054] Add intermediate B (2.52g), benzyltriethylammonium chloride (TEBAC, 0.34g) and epichlorohydrin (13.8g) to a 250mL single-mouth round bottom bottle, and react at 80°C for 4.5h under magnetic stirring. Then add another part of TEBAC (0.34g) and an aqueous solution of sodium hydroxide (2.4g, the concentration is 5.0mol / L). After the addition, stir and react at room temperature for 1.5h. After the reaction is complete, add ethyl acetate to extract the organic phase. Ethyl acetate was extracted three times, and then the organic phase was combined, and the obtained organic phase was washed three times with water, then dried over anhydrous sodium sulfate, and then concentrated to obtain a mixed product containing isovanillin bio-based epoxy resin monomer. After filtering off the desiccant, the condensate was obtained by rotary evaporation. The above mixture was separated on a silica gel column,...

Embodiment 3

[0060] Weigh the isovanillin bio-based epoxy resin monomer (0.109g) represented by the formula Meng-yangIE in the reaction bottle, add curing agent D (0.097g) at 25°C, heat up to about 75°C, and the sample is in a molten state , Stir quickly to keep the material fully melted and mixed evenly. Then gradually raise the temperature to 100°C to start curing, and then maintain at this temperature for 2 hours to obtain a transparent colorless polymer material. By judging its infrared data, such as Figure 5 As shown, the infrared peaks of ethylene oxide in the original epoxy substrate (860 and 910cm -1 Equal intensity stretching vibration) disappears, indicating that the epoxy group and amine group of the epoxy resin have been completely polymerized, and at the same time due to the ring-opening process of the epoxy, the 3426cm -1 Relative to the raw material epoxy monomer, there is a large absorption, which is inferred to be caused by a large number of hydroxyl groups formed in th...

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Abstract

The invention discloses an application of a novel isovanillin epoxy resin monomer in preparation of a silicon-containing polymer, which comprises the following steps: mixing an isovanillin bio-based epoxy resin monomer as shown in a formula Meng-yangIE with an organic silicon polyamine curing agent as shown in a formula D, a formula E or a formula F, melting, and curing to obtain the novel isovanillin epoxy resin monomer. The silicon-containing polymer containing the isovanillin bio-based epoxy resin monomer as shown in the formula Meng-yangIE is obtained. According to the method, the bio-based isovanillin is used as the raw material for preparing the corresponding epoxy resin monomer material for the first time, the synthesis steps of the resin monomer are simple, the conversion rate of the reaction process is high, the source is wide, the greenization degree is high, and the biological safety of the product is high. In addition, the bio-based epoxy resin obtained through polymerization of the isovanillin epoxy resin monomer is novel in structure, and the obtained bio-based epoxy resin polymer material has low curing processing technology temperature and good heat resistance (the initial decomposition temperature ranges from 300.8 DEG C to 300.8 DEG C).

Description

technical field [0001] The invention belongs to the field of chemical industry, and in particular relates to the application of a novel isovanillin epoxy resin monomer in the preparation of silicon-containing polymers. Background technique [0002] Thermosetting epoxy resin is one of the most widely used plasticizing materials at present. Compared with thermoplastic materials, thermosetting materials have a better service temperature. Based on the high crosslinking effect of the curing agent, the formed resin material has excellent Mechanical properties, thermal properties and corrosion resistance, etc., so it is widely used in coatings, adhesives and electronic and electrical industries, multi-component composite materials and engineering technology research fields. [0003] The global annual usage of epoxy resin exceeds 10 billion US dollars, which means that the demand for resin in the market has increased sharply, but the expansion of market share has also caused the con...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D301/30C07D303/24C08G59/24C08G77/26
CPCC07D301/30C07D303/24C08G59/245C08G77/26Y02P20/584
Inventor 郭凯孟晶晶杨锐管浩李春雨李智勇
Owner NANJING UNIV OF TECH
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