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Lignin-based polyurethane chain extender as well as preparation method and application thereof

A lignin-based and polyurethane technology, applied in the direction of biological raw materials, can solve the problem of browning, etc., and achieve the effect of simple operation, reduced dependence, and enhanced thermal stability

Active Publication Date: 2021-11-19
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the disadvantage of this chain extender is that it turns brown after melting, and is only suitable for the preparation of dark high-performance PUR products.

Method used

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  • Lignin-based polyurethane chain extender as well as preparation method and application thereof
  • Lignin-based polyurethane chain extender as well as preparation method and application thereof
  • Lignin-based polyurethane chain extender as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070]

[0071] IIIa 2,2'-methylene (4-methylphenol)

[0072] Accurately weigh 4-methylphenol (21.6 g, 0.2 mol), 40% formaldehyde solution (9.0 g, 0.12 mol) and p-toluenesulfonic acid (1.72 g, 0.01 mol) in the pressure resistant bottle, 60 ° C water bath heating After stirring for 30 minutes, the reaction was diluted with ethyl acetate, water and ethyl acetate were extracted, dried off in anhydrous sulfate, and the organic phase was concentrated, and the viscous oil liquid (Compound IIIA) was obtained, and the yield was 80.3%. MSI-MS: 229.3 [M + H] + .

[0073] IVA 2,2 '- (((methylene (4-methyl-2,1-phenyl)) bis ((oxygen)) double acetamide

[0074] Accurately weigh IIIa (11.4 g, 0.05 mol), chloroacetamide (5.8 g, 0.0625 mol), potassium anhydrous carbonate (15.5 g, 0.1125 mol), potassium iodide (0.83 g, 0.005 mol) in a 2L round bottom flask, 1.25L acetone, 60 ° C for 6 h, after the end of the reaction, ol drying, water and ethyl acetate extraction, dried anhydrous sulfate, and con...

Embodiment 2

[0078]

[0079] 2A 6,6'-methylene (2,4-dimethylphenol)

[0080] Referring to IIIA synthesis, 2,4-dimethylphenol replace 4-methylphenol, yield of 80.5%. MSI-MS: 257.4 [M + H] + .

[0081] 2B 2, 2 '- (((methylene (4,6-dimethyl-2,1-phenyl)) bis ((oxygen)) double acetamide

[0082] The yield is 98.9% with reference to the IVA synthesis method. MSI-MS: 371.5 [M + H] + .

[0083] I-2 6,6'-methylene (2,4-dimethyl ketaniline)

[0084] Referring to I-1 synthesis method, the yield is 98.4%. MSI-MS: 255.4 [M + H] + .

Embodiment 3

[0086]

[0087] 3A 6,6'-methylene (2-methoxy-4-methylphenol)

[0088] Referring to IIIa synthesis, 4-methyl-2-methoxyphenol replace 4-methylphenol, yield of 79.2%. MSI-MS: 289.3 [M + H] + .

[0089] 3B 2, 2 '- (((methylene (6-methoxy-4-methyl-2,1-phenyl)) bis ((oxygen)) double acetamide

[0090] The yield is 96.4% with reference to the IVA synthesis method. MSI-MS: 403.4 [M + H] + .

[0091] I-3 6,6'-methylene (2-methoxy-4-methylhniline)

[0092] Referring to I-1 synthesis, the yield is 97.6%. MSI-MS: 287.3 [M + H] + .

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Abstract

The invention discloses a lignin-based polyurethane chain extender as well as a preparation method and an application thereof, methylene diphenylamine of the lignin-based polyurethane chain extender is shown as a formula I. The preparation method comprises the following steps: carrying out a hydroxyalkylation reaction on a lignin cracking monomer compound II and a carbonyl compound to obtain a compound III; performing an ammonification reaction on the compound III and chloroacetamide to obtain a compound IV, and performing a Smiles rearrangement reaction on the compound IV to obtain the lignin-based polyurethane chain extender methylene diphenylamine shown in the formula I. According to the invention, green and sustainable lignin is used as a raw material, the carcinogenic potential risk of 2-chloroaniline as a raw material required for producing MOCA is avoided, the dependence on fossil resources is reduced, and the product as a chain extender enhances the thermal stability, mechanical properties and aging resistance of a polyurethane material.

Description

Technical field [0001] The present invention belongs to the field of biological high molecular material, and more particularly to a lignin-based polyurethane chain extender and a preparation method thereof. Background technique [0002] Lignin is widely present in nature, in all higher plants, together with cellulose and hemicellulose, forming the main ingredients of the plant skeleton, and bonded fibers and a double role that makes fibers. In nature, the annual output of lignin is very rich, the second bit is second only to cellulose. Affected by the biosynthesis process, lignin molecules are unlike a duplicate structural unit with cellulose, the chemical structure is very complicated. It is generally recognized that it is a three-dimensional mesh structure of three phenylene cells through ether bonds and carbon bonds, which are censorstrum propylene (G), purple Climbyl propane (S type) and a hydroxyphenylpropane (H type) structural unit. Lignin molecules have a variety of funct...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G18/10C08G18/32
CPCC08G18/10C08G18/3243Y02P30/20
Inventor 朱晨杰黎明晖应汉杰沈涛张博胡瑞佳庄伟李明陈彦君柳东牛欢青杨朋朋
Owner NANJING UNIV OF TECH
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