Non-isocyanate polyurethane preparation method

A non-isocyanate and polyurethane technology, applied in the field of bio-based material synthesis, can solve the problems of poor modifiability, consumption of fossil raw materials, and few kinds of raw materials, and achieve the effect of many kinds and strong modifiability.

Inactive Publication Date: 2019-02-19
QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In view of the excessive consumption of fossil raw materials in the current preparation process of non-isocyanate polyurethane monomers, and the problems of few types of raw materials and poor modifiability, the present invention provides a preparation method of non-isocyanate polyurethane, comprising the following steps:

Method used

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  • Non-isocyanate polyurethane preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Embodiment 1. The method for preparing non-isocyanate polyurethane with mevalonolactone as substrate.

[0042] 1) Preparation of polyol derivatives: ethylenedithiol-bridged mevalonate propylamine dimer.

[0043] a. mevalonate to prepare allylamine mevalonate: mevalonate 1.0g (7.7mmol, 1eq), 3-aminopropene 4.4g (10eq) were dissolved in 30mL of dry m-xylene , stirred and reacted at 100° C. for 2 h. After the reaction was complete, the solvent was removed under reduced pressure to obtain a crude product. The crude product was separated by column chromatography to obtain 1.3 g of pure allylamine mevalonate with a yield of 90.3%. The reaction equation is:

[0044] b. Preparation of ethylenedithiol bridged mevalonate propylamine dimer: 1.0g (5.3mmol, 1eq) of mevalonate allylamine prepared in a, ethanedithiol 0.246g (0.5eq) It was dissolved in 30 mL of dry dichloromethane, placed in a dark environment, stirred and reacted at 25°C for 10 h under ultraviolet light irradiatio...

Embodiment 2

[0051] Embodiment 2. The method for preparing non-isocyanate polyurethane with mevalonolactone as substrate.

[0052] 1) Preparation of polyol derivative ethylenediamine-bridged mevalonate dimer: take 1.0g (7.7mmol, 1.0eq) of mevalonate, dissolve 0.23g (0.5eq) of ethylenediamine in 30mL and dry In m-xylene, stirred and reacted at 100°C for 2 hours, after the reaction was complete, the solvent was removed under reduced pressure to obtain a crude product, which was separated by column chromatography to obtain 2.1 g of pure ethylenediamine-bridged mevalonic acid dimer, producing Rate 85.0%. The reaction equation is as follows:

[0053]

[0054] 2) Preparation of ethylenediamine-bridged six-membered ring carbonate dimer

[0055] Dissolve 2.0 g (6.3 mmol, 1 eq) of the ethylenediamine-bridged mevalonic acid dimer prepared in step 1) in 20 mL of dry dichloromethane, and cool the mixture to 0° C. under nitrogen protection, then Add 5 g of excess dimethyl carbonate to the mixed s...

Embodiment 3

[0059] Embodiment 3. The method for preparing non-isocyanate polyurethane with mevalonolactone as substrate.

[0060] 1) Preparation of polyolefin derivative triallyl mevalonate:

[0061] Dissolve 1.0 g (7.7 mmol, 1 eq) of mevalonate and 1.8 g (3 eq) of 3-chloropropene in 30 mL of dry tetrahydrofuran, add 1.0 g of NaOH, and reflux at 80°C for 2 h. After the reaction was over, 50 mL of ice water was added to the reaction solution, followed by extraction with dichloromethane, rinsing with 100 mL of ultrapure water three times, Na 2 SO 4 After drying, the solvent was removed under reduced pressure to obtain 2.0 g of triallyl mevalonic acid with a yield of 96.9%. The reaction equation is as follows:

[0062]

[0063] 2) Preparation of tricyclic carbonate mevalonate polyurethane precursor.

[0064] Take 2.0 g (7.5 mmol, 1 eq) of triallyl mevalonic acid prepared in step 1) and dissolve it in 30 mL of tetrahydrofuran, add 5.0 g of silver-loaded silica nanospheres, react at 80°...

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Abstract

The invention relates to a non-isocyanate polyurethane preparation method, and belongs to the field of bio-based material synthesis. In order to produce a renewable polyurethane material, bil-mevalonic acid or mevalonic acid or mevalonolactone serves as a substrate, an intermediate product polyatomic alcohol or polybasic carboxylic acid or multi-olefins or a derivative of polyatomic alcohol or polybasic carboxylic acid or multi-olefins is prepared; the obtained intermediate product is subjected to oxidation or carbon dioxide addition or a dehydration condensation reaction for preparation, anda non-isocyanate polyurethane precursor polycyclic carbonate is obtained; then polycyclic carbonate and a diamine compound are adopted for preparation, and a non-isocyanate polyurethane monomer is obtained. The method is suitable for large-scale production of non-isocyanate polyurethane.

Description

technical field [0001] The invention relates to the field of bio-based material synthesis, in particular to a method for preparing non-isocyanate polyurethane. Background technique [0002] The raw materials for the preparation of polyurethane materials mainly rely on traditional fossil products such as polyacids, polyols, and polyamines. Most of these raw materials are non-renewable. Therefore, it is of long-term and important significance to find renewable raw materials for polyurethane synthesis. Traditional polyurethane materials are usually prepared by polymerizing polyols and isocyanate, and isocyanate is a highly toxic substance that is very harmful to the human body and does not conform to the development direction of safety and environmental protection. Therefore, exploring the synthesis of non-isocyanate polyurethanes has great appeal in recent years. The literature (RSC Advances, 2013, 3, 4110) reviews the general synthesis methods of non-isocyanate polyurethanes...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G71/04
CPCC08G71/04
Inventor 赵立军赵晓辉咸漠邓理尹衍龙董文锦
Owner QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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