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A kind of lignin-based polyurethane chain extender and its preparation method and application

A lignin-based, polyurethane technology, applied in the direction of biological raw materials, can solve problems such as browning, and achieve the effects of simple operation, avoiding the potential risk of cancer, high reaction selectivity and yield

Active Publication Date: 2022-05-20
NANJING TECH UNIV
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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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  • A kind of lignin-based polyurethane chain extender and its preparation method and application
  • A kind of lignin-based polyurethane chain extender and its preparation method and application
  • A kind of lignin-based polyurethane chain extender and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070]

[0071] IIIA 2,2’-Methylene(4-Methylphenol)

[0072] Accurately weigh 4-methylphenol (21.6g, 0.2mol), 40% formaldehyde solution (9.0g, 0.12mol) and p-toluenesulfonic acid (1.72g, 0.01mol) in a pressure bottle, and heat it in a water bath at 60°C Stir for 30 minutes, dilute with ethyl acetate after the reaction, extract with water and ethyl acetate, dry over anhydrous magnesium sulfate and concentrate the organic phase to obtain a viscous oily liquid (compound IIIA) with a yield of 80.3%. MSI-MS: 229.3[M+H] + .

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

[0074] Accurately weigh IIIA (11.4g, 0.05mol), chloroacetamide (5.8g, 0.0625mol), anhydrous potassium carbonate (15.5g, 0.1125mol), potassium iodide (0.83g, 0.005mol) in a 2L round bottom flask, Add 1.25L of acetone, stir at 60°C for 6h, filter after the reaction, spin the filtrate to dryness, extract with water and ethyl acetate, dry over anhydrous magnesium sulfate and concentr...

Embodiment 2

[0078]

[0079] 2A 6,6'-Methylene(2,4-Dimethylphenol)

[0080] Referring to the synthesis method of IIIA, 2,4-dimethylphenol was used instead of 4-methylphenol, and the yield reached 80.5%. MSI-MS: 257.4[M+H] + .

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

[0082] Referring to the synthetic method of IVA, the yield reaches 98.9%. MSI-MS: 371.5[M+H] + .

[0083] I-2 6,6'-Methylene(2,4-Dimethylaniline)

[0084] Referring to the synthesis method of I-1, 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 the synthesis method of IIIA, 4-methyl-2-methoxyphenol was used instead of 4-methylphenol, and the yield reached 79.2%. MSI-MS: 289.3[M+H] + .

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

[0090] Referring to the synthetic method of IVA, the yield reaches 96.4%. MSI-MS: 403.4[M+H] + .

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

[0092] Referring to the synthesis method of I-1, 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 and its preparation method and application. The lignin-based polyurethane chain extender methylene dianiline is shown in formula I. The preparation method is to crack lignin into a monomeric compound Compound III is obtained through hydroxyalkylation reaction between II and carbonyl compound, compound IV is obtained through ammoniation reaction between compound III and chloroacetamide, and compound IV is obtained through Smiles rearrangement reaction to obtain the lignin-based polyurethane chain extender methylene shown in formula I diphenylamine. The invention uses green and sustainable lignin as a raw material, avoids the potential risk of carcinogenicity of the raw material 2-chloroaniline required for the production of MOCA, reduces the dependence on fossil resources, and the product of the invention enhances the polyurethane material as a chain extender. Thermal stability, mechanical properties and anti-aging ability.

Description

technical field [0001] The invention belongs to the field of bio-based polymer materials, and in particular relates to a lignin-based polyurethane chain extender and its preparation method and application. Background technique [0002] Lignin widely exists in ferns and all higher plants in nature, forms the main component of plant skeleton together with cellulose and hemicellulose, and plays a dual role of bonding fibers and making fibers rigid. In nature, the annual output of lignin is very abundant, ranking second, second only to cellulose. Affected by the biosynthetic process, unlike cellulose, lignin molecules have repeating structural units, and their chemical structures are very complex. It is generally recognized that it is a polymer with a three-dimensional network structure connected by three phenylpropane units through ether bonds and carbon-carbon bonds. These three phenylpropane units are guaiacylpropane (G type), purple Syringylpropane (S-type) and p-hydroxyph...

Claims

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Application Information

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Patent Type & Authority Patents(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 TECH UNIV
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