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Preparation method of binary primary alcohol with adjustable molecular weight for bio-based polyurethane

A dibasic primary alcohol, bio-based technology, applied in the field of biomass polyurethane materials, can solve the problems of difficult separation and purification, harsh reaction conditions, low reactivity, etc., and achieve the effect of simple separation and purification, mild reaction process and high reactivity

Active Publication Date: 2021-12-03
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Chinese patent CN110746299A adopts epoxidation-ring-opening method to prepare soybean oil-based, corn oil-based, peanut oil-based and other polyols. These vegetable oil-based polyols have a large number of hydroxyl groups (functionality 6-10) and are uncontrollable. It is mainly used as a cross-linking agent in the preparation of elastomers, foams, etc., but it is difficult to prepare water-based polyurethane; in addition, there are secondary hydroxyl groups in these vegetable oil-based polyols, which have low reactivity with isocyanates
Chinese patent CN101139252A carries out alcoholysis reaction with diethanolamine and jatropha oil to obtain bio-based dibasic primary alcohols containing terminal hydroxyl groups. Although the reactivity is high, the molecular weight of such dibasic alcohols is low, and the distance between the two hydroxyl groups Too close, as the soft segment of polyurethane, it cannot play the role of extending the polymer chain, and the long carbon chain contained in it hangs on the side chain, which affects the hydrophilicity and mechanical properties of waterborne polyurethane
[0004] Although there are various types of vegetable oil-based polyols and many synthetic methods, there are few studies on vegetable oil-based primary dihydric alcohols, and most of the synthetic methods are based on chemical reactions, which have harsh reaction conditions, low yields, many by-products, and difficulties in separation and purification. And other issues

Method used

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  • Preparation method of binary primary alcohol with adjustable molecular weight for bio-based polyurethane
  • Preparation method of binary primary alcohol with adjustable molecular weight for bio-based polyurethane
  • Preparation method of binary primary alcohol with adjustable molecular weight for bio-based polyurethane

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Experimental program
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Effect test

Embodiment 1

[0023] Preparation of β- keto ester (1): 1 part of sodium hydride in mineral oil after elution added to the reactor, and then were added 8.3 parts of methyl 10- dehydrated undecene, 2.3 parts of dehydrated N, N - dimethylformamide and 4.6 parts of dehydrated dimethyl sulfoxide, nitrogen gas, at an oil bath of 45 ℃ reaction 28 h, after completion of the reaction, the product was slowly poured into dilute hydrochloric acid and the neutralized after the aqueous phase was acidic, and then poured into a separatory funnel and allowed to stand, stratification, the lower aqueous phase was discarded, washed with saturated aqueous sodium chloride was added until the aqueous phase was rendered neutral, collecting the oil phase distilled water under reduced pressure to obtain β - ketoesters, sealed from light, backup;

[0024] Preparation of bio-based diol (2): The above-described parts 1 β- keto ester, 0.42 parts of mercaptoethanol, 0.03 parts of 2,2-dimethoxy-2-phenyl acetophenone was added...

Embodiment 2

[0027] Preparation of β- keto ester (1): 2.8 parts of sodium ethoxide after elution of mineral oil added to the reactor, and then dehydrated successively added 12.3 parts of methyl oleate and 3.8 parts of dehydrated N, N- dimethyl carboxamide, purged with nitrogen, at 65 deg.] C oil bath of the reaction 20 h, after completion of the reaction, the product was slowly poured into dilute hydrochloric acid and the water and the acidic phase, and then poured into a separatory funnel in standing, stratification, the lower aqueous phase was discarded, washed with saturated aqueous sodium chloride was added until the aqueous phase was rendered neutral, the oil phase was collected under reduced pressure to remove water to obtain a β- ketoester, sealed from light, backup;

[0028] Preparation of bio-based diol (2): 2.5 parts of the above-β- keto ester, 1.2 parts of 6-mercapto-1-hexanol, 0.04 parts of 2,2-dimethoxy-2-phenyl benzene ethanone added to a quartz tube, the quartz tube was then pla...

Embodiment 3

[0031](1) Preparation of β-ketorate: 4.7 parts of the eluting mineral oil to the reactor, then add 15.3 parts of the dehydrated mustard, 5 parts dehydrated tetrahydrofuran and 15 dehydrated Diamel sulfoxide, into nitrogen, reacts in a 55 ° C oil supply 24 h, after the reaction is completed, the product is slowly poured into the dilute hydrochloric acid in progress, so that the neutralized water is acidic, and then pour it into points The liquid drain is allowed to stand, layered, discard the lower aqueous phase, add saturated brine to wash until the aqueous phase exhibits neutral, collecting the oil phase under reduced pressure to remove water, obtain keta-ketoate, seal prevent light, standby ;

[0032] (2) Preparation of biological diols: 5 parts of the above keta-ketorate, 3 parts of 11-mercapto-1-elevol, 0.08 parts of residential double methyl ether and 3 parts of dichloromethane (for Dissolved 11-mercapto-1-decolina and anti-rodium double methyl ether) Add in quartz pipe, then...

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Abstract

The invention discloses a preparation method of binary primary alcohol with adjustable molecular weight for bio-based polyurethane. Firstly, bio-based fatty acid ester containing alpha-hydrogen atoms is used as a raw material and subjected to Claisen condensation reaction in the presence of a basic catalyst and a solvent, and beta-keto ester with the molecular weight increased by one time is obtained. And then, by introducing the primary hydroxyl group into beta-keto ester and further prolonging a carbon chain under ultraviolet irradiation by utilizing a thiol-ene click reaction, the bio-based binary primary alcohol with adjustable molecular weight, a long main chain and a short side chain is obtained. The bio-based binary primary alcohol is prepared by using the natural vegetable oil derivative fatty acid ester instead of a petroleum-based monomer as a raw material, has the advantages of reproducibility, easiness in degradation and the like, and can be widely applied to manufacturing of polyurethane for leather, synthetic leather, textiles, plastics, rubber, building materials and coatings.

Description

Technical field [0001] The present invention relates to an adjustable molecular weight bio-based polyurethane prepared by a diprimary alcohols, polyurethane material is in the field of biomass. Background technique [0002] Polyurethanes are a class of a diisocyanate and a diol obtained by addition polymerization of a polymer material containing a repeating structure of a urethane bond (-NHCOO-) of. In 1937, the German Otto Bayer first discovered and made of polyurethane, then began to enter the industrial production of polyurethane and widely used. So far, polyurethane production already has a considerable scale, it will become one of the world's indispensable material. At present, the diisocyanate on the market and raw materials derived from petroleum diol are non-renewable resources, with concerns about dwindling world oil resources and the countries of petrochemical raw materials are depleted status quo, making petroleum-based products urgently needed looking for new alternat...

Claims

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Application Information

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IPC IPC(8): C07C319/18C07C323/52
CPCC07C319/18C07C67/343C07C323/52C07C69/738
Inventor 范浩军王丽向均陈意颜俊孙哲王松杭
Owner SICHUAN UNIV
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