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Full-bio-based aryl diamine chain extender as well as preparation method and application thereof

A base aryl diamine chain extender, base aryl diamine technology, applied in the field of all bio-based aryl diamine chain extenders and its preparation, can solve the problem of structure containing halogen, molecular structure easily absorbed by human body, carcinogenic Effect and other issues, to achieve the effect of improving tensile strength, avoiding dependence on fossil resources, and high reaction selectivity

Pending Publication Date: 2022-06-07
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the problem that MOCA contains halogens in its structure, and its molecular structure is easily absorbed by the human body to cause carcinogenic effects has always been concerned by people.

Method used

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  • Full-bio-based aryl diamine chain extender as well as preparation method and application thereof
  • Full-bio-based aryl diamine chain extender as well as preparation method and application thereof
  • Full-bio-based aryl diamine chain extender as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-5

[0084] To the reaction bottle was added p-hydroxybenzaldehyde (20mmol, 2.44g), acetone (10mmol, 0.58g), the solvent was methanol 50mL, and the catalyst 1mmol was DBU, TBD, NaOH, CaO and alkaline ionic liquids, respectively + [NH 3 CH 2 CH 2 OH][CH 3 COO] - The reaction was reacted at 70 °C for 3h, the reaction liquid was taken for HPLC detection, the conversion rate and yield were shown in Table 2 below, the reaction liquid was filtered or directly concentrated after the reaction was completed, water and ethyl acetate were added for extraction, and the organic phase was separated for column chromatography purification (ethyl acetate / n-hexane = 1:1 gradient elution), that is, compound III1 was obtained. 1 H NMR(400MHz,CDCl 3 )7.70(d,J＝16Hz,2H),7.57(dd,J＝6.7,2Hz,4H),7.05(d,J＝16Hz,2H),6.83(dd,J＝6.7,2Hz,4H)； 13 C NMR(100MHz,CDCl 3 )δ115.8,123.3,127.8,130.6,142.2,157.7,188.6.MSI-MS:289.3[M+Na] + 。

[0085] Table 2 Example 1-5 Catalytic reaction efficiency of different catalysts

[00...

Embodiment 6

[0088]Metal-free catalyzed phenol hydroxylamine reaction process: weigh III1 (10mmol, 2.66g), chloroacetylamide (20mmol, 1.87g), anhydrous potassium carbonate (25mmol, 3.45g), potassium iodide (1mmol, 0.27g) in a 1L round bottom flask, add 700mL acetone, stirred at 60 °C for 6h, filtered after the end of the reaction, filtrate dried, water and ethyl acetate extraction, anhydrous magnesium sulfate dried and concentrated organic phase, The recrystallization of chloroacetamide product V1 was obtained, and the yield was 98.2%. 1 H NMR(400MHz,DMSO-d6)δ7.82(d,2H),7.68(dd,4H),7.28(s,4H),7.03(d,2H),6.88(dd,4H),4.64(s,4H). 13 C NMR(100MHz,DMSO-d6)δ74.2,114.2,123.3,127.5,130.2,142.2,157.6,170.5,189.3.MSI-MS:403.3[M+Na] + 。

[0089] Accurately weigh the chloroacetamide product (10mmol, 3.80g), potassium hydroxide (40mmol, 2.24g) in a microwave reaction bottle, add 150mL dimethyl sulfoxide (DMSO) and 50mL N, N-dimethacrylamino (DMPU), microwave heating at 180 °C for 2h, after the reaction end...

Embodiment 7

[0091]Metal-catalyzed phenol hydroxylamine reaction process: accurately weigh compound III1 (0.133g, 0.5mmol), Reney nickel (0.05g, 0.85mmol) and tert-pentanol 25ml in the reactor, into 10 bar ammonia, 170 °C reaction for 18h. After the end of the reaction, the reaction solution was tested by HPLC, and the yield was 96.0%. After the reaction is finished, the filtrate is drained, and the column chromatography (ethyl acetate / n-hexane) is separated and purified.

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Abstract

The invention discloses a full-bio-based aryl diamine chain extender and a preparation method and application thereof.The structure of the full-bio-based aryl diamine chain extender is shown in the formula I. The preparation method of the full-bio-based aryl diamine chain extender comprises the steps that a lignin oxidative depolymerization monomer compound shown in the formula II and a bio-based ketone compound shown in the formula IV are subjected to an aldol condensation reaction, and a compound III is obtained; and carrying out phenolic hydroxyl amination reaction on the compound III to obtain the full-bio-based aryl diamine as shown in the formula I. The product disclosed by the invention can be used for replacing a traditional diamine chain extender to be used for preparing a polyurethane elastomer, and the tensile strength, the tensile elastic modulus and the thermal stability of a polyurethane material are improved.

Description

Technical field [0001] The present invention belongs to the field of bio-based polymer materials, specifically relates to a whole bio-based aryl diamine chain expander and preparation method and application thereof. Background [0002] Lignocellulosic biomass is considered a renewable alternative source of carbon and consists mainly of cellulose, hemicellulose and lignin. Lignin is an irregular aromatic biopolymer that accounts for 15%-30% of lignocellulose biomass and is a component of the cell wall of terrestrial plants. Lignin has an aromatic structure and is therefore considered a renewable source of carbon from a considerable source of aromatic compounds. However, the use of lignin has been limited to energy recovery, and most biorefining processes degrade lignin, including unstable ether bond breaks (such as β-O-4 bonds) and reaction intermediates form C-C bonds by breaking bonds, and the synthesized degraded lignin is usually incinerated to generate heat and electricity du...

Claims

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Application Information

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IPC IPC(8): C07C225/22C07C221/00C07C45/74C07C49/255C08G18/67C08G18/42
CPCC07C225/22C07C221/00C07C45/74C08G18/675C08G18/4277C07C2601/08C07C2601/14C08G18/4825C08G18/10C07C231/12C07C49/248C07C49/252C07C235/06Y02P20/54
Inventor 沈涛张博朱晨杰应汉杰黎明晖李明庄伟胡瑞佳杨朋朋
Owner NANJING UNIV OF TECH
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