WO2009043301A1 - Procédé de préparation de polyol polyéther et application du produit préparé - Google Patents

Procédé de préparation de polyol polyéther et application du produit préparé Download PDF

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Publication number
WO2009043301A1
WO2009043301A1 PCT/CN2008/072559 CN2008072559W WO2009043301A1 WO 2009043301 A1 WO2009043301 A1 WO 2009043301A1 CN 2008072559 W CN2008072559 W CN 2008072559W WO 2009043301 A1 WO2009043301 A1 WO 2009043301A1
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WO
WIPO (PCT)
Prior art keywords
polyether polyol
mixture
palm oil
catalyst
initiator
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/CN2008/072559
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English (en)
Chinese (zh)
Inventor
Jun YING
Hongjin Zhai
Jue YING
Guiqin Lai
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JURONG NINGWU CHEMICAL CO Ltd
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JURONG NINGWU CHEMICAL CO Ltd
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Publication of WO2009043301A1 publication Critical patent/WO2009043301A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/48Polyethers
    • C08G18/4891Polyethers modified with higher fatty oils or their acids or by resin acids
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2603Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
    • C08G65/2615Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen the other compounds containing carboxylic acid, ester or anhydride groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2696Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the process or apparatus used
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2101/00Manufacture of cellular products

Definitions

  • the invention relates to a method for preparing an organic polymer compound, in particular to a method for preparing a polyhydroxy-containing polyether by using an oxidized olefin, a polyol compound or an amine compound as a raw material, in particular, a polyether polyether for polyurethane
  • a method for preparing an organic polymer compound in particular to a method for preparing a polyhydroxy-containing polyether by using an oxidized olefin, a polyol compound or an amine compound as a raw material, in particular, a polyether polyether for polyurethane
  • Polyether polyol is an important raw material of polyurethane materials, and its preparation method is mostly under the action of pressure, temperature and catalyst, from ethylene glycol, propylene glycol, diethylene glycol, glycerol, ethylene diamine, triethanolamine, three Isopropanolamine, toluenediamine and the like are mixed with a polyhydric alcohol (such as sucrose, sorbitol, etc.) as a starter and reacted with an alkylene oxide.
  • a polyhydric alcohol such as sucrose, sorbitol, etc.
  • the disadvantages of this preparation method are as follows: high preparation cost, large amount of oxidized olefins are required, and oxidized olefins are petrochemical products. Under the condition of increasingly tight petroleum resources, it is very important to reduce the consumption of such olefins. . Summary of the invention
  • the object of the present invention is to provide a preparation method of a polyether polyol capable of reducing the consumption of oxidized olefins and an application of the obtained product, which can save the use amount of the oxidized olefin and reduce Preparation cost;
  • the obtained polyether polyol can better meet the requirements of polyurethane material production.
  • a process for preparing a polyether polyol which is characterized in that it is obtained by reacting a co-initiator with an olefin oxide under the action of a basic catalyst. Including the following steps:
  • a mixture of palm oil or palm oil and eucalyptus oil with a polyol or an amine compound or a mixture of the two is added to the reactor as a co-initiator.
  • the weight ratio of palm oil to soybean oil is 10-100% for palm oil and 0-90% for soybean oil.
  • the weight ratio of the mixture of palm oil or palm oil to soybean oil and the polyol or amine compound or a mixture of the two in the co-initiator is: 3-95% mixture of palm oil or palm oil and soybean oil, polyol Or an amine compound or a mixture of the two is 5-97%.
  • the polyol compound is one or a mixture of sucrose, sorbitol, a-methyl glucoside, mannitol, diethylene glycol, glycerol, propylene glycol, ethylene glycol, pentaerythritol;
  • the amine compounds are ethylenediamine, monoethanolamine, diethanolamine, triethanolamine, monoisopropanolamine, and One or a mixture of isopropanolamine, triisopropanolamine, toluenediamine.
  • the catalyst is one or a mixture of potassium hydroxide, sodium hydroxide, monomethylamine, dimethylamine, trimethylamine.
  • the catalyst may also be dissolved in water to form a liquid catalyst for addition to the reactor.
  • the amount of the catalyst is from 0.2 to 21% of the co-initiator.
  • An oxidized olefin is added to the above reactor and allowed to react sufficiently.
  • the total amount of the co-initiator is 0.2 to 6 times by weight of the olefin oxide at a temperature of 90 to 155 ° C, and the pressure is maintained at 0.05 to 0.6 MPa.
  • the oxidized olefin may be one of ethylene oxide, propylene oxide and butylene oxide, or several of them; if it is several, the oxidized olefin may be added after mixing or different olefin oxides. Join in segments.
  • the above reaction product is degassed and purified to obtain a polyether polyol for polyurethane.
  • the polyether polyol has an average molecular weight of from 300 to 2,000.
  • polyether polyol prepared by the above preparation method is characterized in that: 100 parts by weight of polyether polyol, 1-4 parts of silicone oil, 0.3-4 parts of polyurethane foam molding catalyst, and polyurethane foaming agent are used in parts by weight. 0.5-50 parts, 80-350 parts of isocyanate, foamed at high speed and foamed to obtain a polyurethane foam product.
  • the polyurethane foam molding catalyst is: N, N-dimethylcyclohexylamine, tetramethylethylenediamine, N, N, N', N'-tetramethyl-1, 3 - butanediamine, N, N'-dimethylpiperazine, triethylenediamine, triethanolamine, dimethylethanolamine, pentamethyldiphenyl and triamine, potassium oleate, stannous oleate, octanoic acid Tin and dibutyltin dilaurate may be used singly or in combination of two or more.
  • the polyurethane foaming agent is: fluorotrichloromethane, trifluorotrichloromethane, dichloromethane, difluoromethylene chloride, carbon dioxide, water, dichlorotrifluoroethane, monofluorotrichloroethane, etc. It can be used alone or in combination of two or more.
  • the technical scheme of the present invention is to use palm oil or a mixture of palm oil and soybean oil and a low molecular weight polyol as a co-initiator, or a mixture of palm oil or palm oil and soybean oil and an amine compound as a co-initiator. Or using palm oil or a mixture of palm oil and soybean oil and a blend of a polyol and an amine compound as a co-initiator, and reacting with an oxidized olefin at a certain pressure and temperature in the presence of a basic catalyst. Polyether polyol.
  • the specific process is as follows: a mixture of palm oil or palm oil and soybean oil, a low molecular weight polyol or an amine compound or a blend of a low molecular weight polyol and an amine compound, a catalyst, etc., in a reactor at 90 to 155 ° C, pressure control at 0.6MPa, adding 0.2 to 6 times the starting material (palm oil or a mixture of palm oil and soybean oil + polyol or amine compound or blend of polyol and amine compound + catalyst) The weight of the olefin oxide is reacted with the initiator. When the oxidized olefin is added, it is kept at the reaction temperature for a period of time. The reaction is carried out for a sufficient period of time, followed by a process such as degassing and refining to obtain a polyether polyol having an average molecular weight of 300 to 2,000.
  • the invention can save the use amount of the oxidized olefin, and the obtained polyether polyol can well meet the needs in the production of the polyurethane material, and the product has good dimensional stability, good fluidity and moderate viscosity.
  • the invention has the advantages that: palm oil and low-distilled polyol or amine compound are co-initiators instead of the original initiator, the production raw materials are easily available, and the consumption ratio of oxidized olefins decreases. 10%, the obtained polyether has good degradability.
  • the amount of the catalyst is 10% of the total amount of the co-initiator, and propylene oxide is added first.
  • the amount of propylene oxide is 0.5 times the total weight of the co-initiator, and the temperature is controlled at 0.5. Below MPa, when the temperature reaches 110 °C, the propylene oxide is added three times the total weight of the total initiator. Due to the exothermic reaction, the control temperature should not exceed 135 ° C, and the pressure is controlled below 0.6 MPa.
  • the amount of catalyst is 15% of the total amount of co-initiator added to the reactor, first adding propylene oxide, adding propylene oxide The amount is 0.3 times of the total weight of the co-initiator, the pressure in the heating process is controlled below 0.5 MPa, and the propylene oxide is added at a temperature of 90 ° C. The amount of propylene oxide is 5 times the total weight of the co-initiator, due to the reaction. Exothermic, the control temperature should not exceed 135 °C, and the pressure should be controlled below 0.6MPa.
  • the amount of the catalyst is 21% of the total amount of the co-initiator, and is added to the reactor to raise the temperature. When the temperature reaches 100 ° C, propylene oxide is added, and the amount of propylene oxide is 6 times of the total weight of the co-initiator.
  • the reaction is exothermic, the control temperature must not exceed 145 °C, and the pressure is controlled below 0.5 MPa.
  • the amount of catalyst is 5% of the total amount of co-initiator Adding to the reactor, heating up, starting to add olefin oxide at a temperature of 100 ° C, the amount of oxidized olefin added is 4 times the total weight of the co-initiator, wherein, propylene oxide 60%, ethylene oxide 20%, butylene oxide 20 %. Due to the exothermic reaction, the control temperature shall not exceed 135 °C and the pressure shall be controlled below 0.5 MPa.
  • the amount of catalyst is total co-initiator 5% of the amount is added to the reactor, and the temperature is raised. When the temperature reaches 100 °C, propylene oxide is added, and the amount of propylene oxide is 6 times of the total weight of the co-initiator.
  • the reaction temperature is not more than 135 °C due to the exothermic reaction. , the pressure is controlled below 0.5MPa.
  • Example 11
  • polyether polyol prepared by the preparation method of the invention takes 100 parts of polyether polyol, 1 part of silicone oil, 4 parts of polyurethane foam molding catalyst N, N-dimethylcyclohexylamine, polyurethane type
  • the foaming agent is 0.5 parts of methylene chloride and 80 parts of isocyanate. The mixture is foamed at a high speed and then foamed to obtain a polyurethane product.
  • Example 13
  • the use of the polyether polyol prepared by the preparation method of the invention comprises 100 parts of a polyether polyol, 2 parts of a silicone oil, 2 parts of a polyurethane foam molding catalyst mixture of triethylenediamine and triethanolamine, and a polyurethane type
  • the foaming agent is 20 parts of monofluorotrichloroethane and 150 parts of isocyanate. After high-speed stirring and mixing, the polyurethane product is obtained by foaming.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Polyethers (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

L'invention porte sur un procédé de préparation d'un polyol polyéther pour de la mousse de polyuréthane et sur l'application du produit préparé. Le polyol polyéther est préparé avec un coinitiateur et de l'oxyde d'alkylène par réaction sous l'action d'un catalyseur alcalin. L'huile de palme ou un mélange d'huile de palme et d'huile de soja est utilisé comme coinitiateur conjointement avec un composé polyol et/ou amine dans le réacteur ; le catalyseur et l'oxyde d'alkylène sont ajoutés dans le réacteur pour réagir à une certaine température et une certaine pression pour préparer le polyol polyéther.
PCT/CN2008/072559 2007-09-29 2008-09-27 Procédé de préparation de polyol polyéther et application du produit préparé Ceased WO2009043301A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN2007101333717A CN101173039B (zh) 2007-09-29 2007-09-29 一种聚醚多元醇的制备方法及制得产品的应用
CN200710133371.7 2007-09-29

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WO2009043301A1 true WO2009043301A1 (fr) 2009-04-09

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102617848A (zh) * 2012-04-18 2012-08-01 南宁市化工研究设计院 一种山梨醇聚醚多元醇的制备方法
CN111410738A (zh) * 2020-04-15 2020-07-14 山东蓝星东大有限公司 胺类自催化聚醚多元醇的制备方法
CN113105617A (zh) * 2021-04-12 2021-07-13 山东蓝星东大有限公司 高性能防水涂料用聚醚多元醇的制备方法
CN113698587A (zh) * 2021-09-08 2021-11-26 航锦科技股份有限公司 硬泡聚醚多元醇的制备方法
CN118186624A (zh) * 2024-05-20 2024-06-14 晋江安润纺织有限公司 一种生物基聚氨酯弹性纤维的制备方法
CN119306935A (zh) * 2024-12-18 2025-01-14 山东尚正新材料科技股份有限公司 生物基胺化改性脂肪醇聚氧乙烯醚硫酸盐的制备方法
US12325771B1 (en) 2024-05-20 2025-06-10 Jinjiang Anrun Textile Co., Ltd. Preparation method for biobased polyurethane elastic fibers

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CN101173039B (zh) * 2007-09-29 2010-04-14 句容市宁武化工有限公司 一种聚醚多元醇的制备方法及制得产品的应用
CN101314638B (zh) * 2008-07-09 2010-06-02 句容市宁武化工有限公司 循环利用水资源的聚醚多元醇的制备方法
CN101684171B (zh) * 2008-09-27 2012-11-14 上海联合气雾制品灌装有限公司 用可再生原料制备单组分聚氨酯泡沫
CN101392054B (zh) * 2008-10-31 2010-08-11 句容市宁武化工有限公司 一种甘油基聚醚多元醇的制备方法
CN101974149B (zh) * 2010-10-21 2012-07-25 句容宁武新材料发展有限公司 一种聚醚多元醇的制备方法
JP2016501281A (ja) * 2012-11-20 2016-01-18 ビーエーエスエフ ソシエタス・ヨーロピアBasf Se 天然油を主原料とするポリエーテルエステルポリオールの製造方法及び硬質ポリウレタンフォームにおけるその使用方法
CN104311811A (zh) * 2014-10-11 2015-01-28 淄博德信联邦化学工业有限公司 改性生物基聚醚多元醇及其制备方法
CN104448292A (zh) * 2014-12-09 2015-03-25 淄博德信联邦化学工业有限公司 高效加固料用聚醚多元醇及其制备方法
CN107955151A (zh) * 2017-11-10 2018-04-24 广州市友聚米新材料有限公司 一种生物基改性硬泡多元醇的制备方法
CN107903388A (zh) * 2017-11-28 2018-04-13 山东诺威新材料有限公司 用于矿用注浆料的硬泡聚醚多元醇及制备方法
US10479862B2 (en) * 2017-12-07 2019-11-19 Covestro Llc Amine based polymer polyol stabilizers
CN109306057B (zh) * 2018-09-29 2020-12-15 山东一诺威新材料有限公司 Ocf专用聚醚多元醇的制备方法

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CN1887929A (zh) * 2006-07-24 2007-01-03 句容市宁武化工有限公司 聚氨酯泡沫用聚醚多元醇的制备方法及制得产品的应用
CN101173039A (zh) * 2007-09-29 2008-05-07 句容市宁武化工有限公司 一种聚醚多元醇的制备方法及制得产品的应用

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CN1887929A (zh) * 2006-07-24 2007-01-03 句容市宁武化工有限公司 聚氨酯泡沫用聚醚多元醇的制备方法及制得产品的应用
CN101173039A (zh) * 2007-09-29 2008-05-07 句容市宁武化工有限公司 一种聚醚多元醇的制备方法及制得产品的应用

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102617848A (zh) * 2012-04-18 2012-08-01 南宁市化工研究设计院 一种山梨醇聚醚多元醇的制备方法
CN111410738A (zh) * 2020-04-15 2020-07-14 山东蓝星东大有限公司 胺类自催化聚醚多元醇的制备方法
CN111410738B (zh) * 2020-04-15 2023-06-02 山东蓝星东大有限公司 胺类自催化聚醚多元醇的制备方法
CN113105617A (zh) * 2021-04-12 2021-07-13 山东蓝星东大有限公司 高性能防水涂料用聚醚多元醇的制备方法
CN113698587A (zh) * 2021-09-08 2021-11-26 航锦科技股份有限公司 硬泡聚醚多元醇的制备方法
CN118186624A (zh) * 2024-05-20 2024-06-14 晋江安润纺织有限公司 一种生物基聚氨酯弹性纤维的制备方法
US12325771B1 (en) 2024-05-20 2025-06-10 Jinjiang Anrun Textile Co., Ltd. Preparation method for biobased polyurethane elastic fibers
CN119306935A (zh) * 2024-12-18 2025-01-14 山东尚正新材料科技股份有限公司 生物基胺化改性脂肪醇聚氧乙烯醚硫酸盐的制备方法

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