[go: up one dir, main page]

WO2018166413A1 - Copolyétherglycol à chaîne latérale fluorée facilement soluble, copolymerisé à partir de perfluoralkylglycidyléther et d'un éther polycyclique - Google Patents

Copolyétherglycol à chaîne latérale fluorée facilement soluble, copolymerisé à partir de perfluoralkylglycidyléther et d'un éther polycyclique Download PDF

Info

Publication number
WO2018166413A1
WO2018166413A1 PCT/CN2018/078672 CN2018078672W WO2018166413A1 WO 2018166413 A1 WO2018166413 A1 WO 2018166413A1 CN 2018078672 W CN2018078672 W CN 2018078672W WO 2018166413 A1 WO2018166413 A1 WO 2018166413A1
Authority
WO
WIPO (PCT)
Prior art keywords
glycidyl ether
fluorine
side chain
propylene oxide
ether
Prior art date
Application number
PCT/CN2018/078672
Other languages
English (en)
Chinese (zh)
Inventor
孔庆刚
施博文
王静
刘飞
Original Assignee
南京信息工程大学
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by 南京信息工程大学 filed Critical 南京信息工程大学
Publication of WO2018166413A1 publication Critical patent/WO2018166413A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular 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 only
    • C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
    • C08G65/16—Cyclic ethers having four or more ring atoms
    • C08G65/18—Oxetanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular 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 only
    • C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
    • C08G65/16—Cyclic ethers having four or more ring atoms
    • C08G65/20—Tetrahydrofuran
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular 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 only
    • C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular 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 only
    • C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
    • C08G65/223—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring containing halogens
    • C08G65/226—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring containing halogens containing fluorine

Definitions

  • the invention belongs to the technical field of intermediates of polymer materials, and particularly relates to a readily soluble side chain fluorine-containing copolyether glycol copolymerized by a perfluoroalkyl glycidyl ether and a polycyclic ether.
  • 3,591,547 A describes a binary copolyol ether of the following structure C compound with glycerol and propylene oxide.
  • Patent CN201110049906.9 reports a binary copolyether glycol of the following structure D compound and tetrahydrofuran.
  • Patent CN201010022447.0 reports binary copolyether diols of the following structure E compounds and F compounds.
  • fluorine-containing homopolymers and binary copolymerized fluorine-containing side chain polyether polyols all exert a special effect of weather resistance, oxidation resistance and corrosion resistance of fluorine elements on the polymer chain.
  • the fluorine group has an extremely low surface free energy, and if it covers the surface of the polymer, it can impart excellent water repellency, oil repellency, abrasion resistance, low friction coefficient and stain repellency to the polymer.
  • the patent CN2013107367731 and the patent CN201310738875.7 report the multi-ring ring-opening copolymerization of four monomers having a length of a perfluoroalkyl-substituted three-membered cyclic ether and a four- or five-membered cyclic ether.
  • the object of the present invention is to overcome the deficiencies of the prior art and to provide a soluble side chain fluorine-containing copolyether glycol which is substituted by propylene oxide and a perfluoroalkyl group.
  • a ternary cationic copolymerization of a glyceryl ether and a four-membered cyclic oxetane or a five-membered cyclic tetrahydrofuran can obtain a side chain fluorine-containing copolyether diol having a desired fluorine content, and the side chain fluorine-containing copolyether
  • the diol has excellent solubility and is easily soluble in general-purpose, non-toxic or low-toxic solvents.
  • a side chain fluorine-containing copolyether glycol obtained by substituting propylene oxide, perfluoroalkyl glycidyl ether and oxetane or tetrahydrofuran to have a molecular structure as shown in Structural Formula I:
  • R is any one of hydrogen, a saturated alkyl group, a saturated alkoxy group, a phenoxy group, and a benzyloxy group.
  • the number average molecular weight is from 1000 to 10000 g/mol, and is a colorless or light yellow transparent viscous liquid.
  • the preparation method of the above copolyether diol is prepared by copolymerization of perfluoroalkyl glycidyl ether, substituted propylene oxide and oxetane or tetrahydrofuran, and the reaction formula is represented by the following formula:
  • R is any one of hydrogen, a saturated alkyl group, a saturated alkoxy group, a phenoxy group, and a benzyloxy group.
  • the perfluoroalkyl glycidyl ether is selected from any one of the following structural compounds:
  • the substituted propylene oxide is selected from any one of the following structural compounds:
  • L is any natural number from 0 to 10.
  • the above preparation method specifically includes the following steps:
  • step (2) adding a solvent, oxetane or tetrahydrofuran, a cationic initiator and a diol initiator in a waterless and oxygen-free reactor equipped with a stirrer, at a temperature of -10 ° C to 15 ° C, into the kettle
  • the substituted propylene oxide and perfluoroalkyl glycidyl ether solution in the above step (1) is slowly added dropwise, and then at -10 ° C to 15 ° C, the polymerization reaction is carried out for 5 to 15 hours, and then 3 to 10 times of diol is added.
  • the amount of the starting material is deionized water to terminate the reaction;
  • the organic solvent in the reaction vessel is distilled off and recovered, and then 1.5 to 2.5 volumes of distilled water of the mixture after distillation is added, using sodium carbonate, sodium hydrogencarbonate, ammonium carbonate, ammonium hydrogencarbonate or sodium hydroxide.
  • the alkaline compound was neutralized to a pH of 7, the mixture was stirred and washed, and the mixture was allowed to stand for separation.
  • the aqueous phase was separated, and the oil phase was washed once again with distilled water, and allowed to stand for stratification. After the oil phase is dehydrated and dried, the solvent is removed to obtain a side chain fluorine-containing copolyether glycol.
  • the substituted propylene oxide and perfluoroalkyl glycidyl ether solution in step (2) should be added dropwise within 1 to 6 hours.
  • the solvent for dissolving the substituted propylene oxide and the perfluoroalkyl glycidyl ether in the step (1) is selected from the group consisting of dichloromethane, 1,4-dioxane, diethyl ether, tetrahydrofuran, acetone, methyl ethyl ketone, dibutyl ether One of them.
  • the cationic initiator is selected from the group consisting of 20% by mass of fuming sulfuric acid, perchloric acid, trifluoroacetic acid, trifluoromethanesulfonic acid, boron trifluoride etherate, trichloroacetic acid, phosphoric acid, trichlorination One of aluminum, titanium tetrachloride, tin tetrachloride, zinc chloride, and antimony pentachloride.
  • the diol initiator is selected from one of ethylene glycol, 1,2-propylene glycol, 1,3-propanediol, and 1,4-butanediol.
  • the present invention employs a substituted propylene oxide and a perfluoro-substituted alkyl glycidyl ether to copolymerize with one of a four-membered cyclic ether or a five-membered cyclic ether, and has the beneficial effects of: (1) by changing the perfluoro group The ratio of the substituted alkyl glycidyl ether to the three raw materials of one of the substituted propylene oxide and the four-membered cyclic ether or the five-membered cyclic ether, to synthesize the desired side chain fluorine-containing copolyether glycol with different fluorine content, Make full use of expensive fluorine raw materials; (2) because a variety of structural groups can be substituted on propylene oxide, so that the raw material structure can be selected according to the next reaction with the side chain fluorine-containing copolyether diol, One step is to copolymerize the propylene oxide monomer with the same solubility parameter
  • the problem of severe phase separation and incompatibility (3)
  • the side chain fluorine-containing copolyether glycol is easily dissolved in a non-toxic or low-toxic solvent which is industrially versatile and inexpensive, which can be largely Low processing costs, reduce pollution processing environment.
  • the side chain fluorine-containing copolyether diols provided by the present invention are extremely convenient in various subsequent uses, and the space for the use of such polyether diols is also expanded to a considerable extent.
  • the reaction was quenched by the addition of 20 ml of deionized water, and the solvent was evaporated and neutralized to neutral with sodium carbonate. It was washed with 100 mL of deionized water for 20 minutes and allowed to stand for stratification. The oil phase was again washed once with distilled water and allowed to stand for stratification. The oil phase was passed through a rotary evaporator to remove the residual solvent to obtain a crude polyether diol having a side chain fluorine-containing phase. Then, it was vacuum dried at 120 ° C under a pressure of 5 mmHg to obtain a colorless viscous liquid of the product, and the yield was 73.5%, which was measured by a GPC analyzer. g/mol, The fluorine content was 6.8%, and the side chain fluorine-containing polyether glycol was numbered CFJM-1.
  • the reaction was maintained at 0 ° C for 10 hours, and the reaction was quenched by the addition of 50 ml of deionized water.
  • the solvent was evaporated and neutralized to neutral with aqueous amine carbonate.
  • the oil phase was vacuum dried at 120 ° C under a pressure of 5 mm Hg to obtain a colorless viscous liquid with a yield of 89%, which was determined by a GPC analyzer. g/mol,
  • the fluorine content was 24.7%
  • the side chain fluorine-containing polyether glycol was numbered CFJM-3.
  • the reaction was maintained at 5 ° C for 6 hours, the reaction was terminated by the addition of 30 ml of deionized water, the solvent was distilled off, and neutralized with a sodium carbonate solution. After adding 200 mL of deionized water and stirring for 20 minutes, the mixture was allowed to stand for stratification, and the oil phase was washed once again with distilled water, and allowed to stand for stratification. The oil phase was vacuum dried at 120 ° C under a pressure of 5 mm Hg to obtain a colorless viscous liquid in a yield of 72%, which was determined by a GPC analyzer. g/mol, The fluorine content was 38.8%, and the side chain fluorine-containing polyether glycol was numbered CFJM-4.
  • the reaction was maintained at 2 ° C for 5 hours, and the reaction was quenched by the addition of 50 ml of deionized water.
  • the solvent was evaporated and neutralized with sodium bicarbonate solution to neutral.
  • the mixture was allowed to stand for stratification, and the oil phase was again washed once with distilled water, and allowed to stand for stratification.
  • a crude polyether diol having a side chain fluorine-containing phase is obtained.
  • the oil phase was vacuum dried at 120 ° C under a pressure of 5 mm Hg to obtain a colorless viscous liquid with a yield of 79%, which was determined by a GPC analyzer. g/mol,
  • the fluorine content was 17.5%
  • the side chain fluorine-containing polyether glycol was numbered CFJM-5.
  • the dioxane solution was controlled to complete in 5 hours.
  • the reaction was maintained at 10 ° C for 15 hours, and the reaction was quenched by the addition of 60 ml of deionized water.
  • the solvent was evaporated and neutralized to neutral with sodium bicarbonate.
  • the oil phase was vacuum dried at 120 ° C under a pressure of 5 mm Hg to obtain a colorless viscous liquid with a yield of 79%, which was determined by a GPC analyzer. g/mol,
  • the fluorine content was 13.7%
  • the side chain fluorine-containing polyether glycol was numbered CFJM-6.
  • Comparative Example 7 is synthesized according to the embodiment of the granted patent ZL201310738875.7
  • Embodiment 8 effect embodiment
  • the present invention employs a substituted propylene oxide and a perfluoro-substituted alkyl glycidyl ether to copolymerize with one of a four-membered cyclic ether or a five-membered cyclic ether, and has the beneficial effects of: (1) by changing the perfluoro group The ratio of the substituted alkyl glycidyl ether to the three raw materials of one of the substituted propylene oxide and the four-membered cyclic ether or the five-membered cyclic ether, to synthesize the desired side chain fluorine-containing copolyether glycol with different fluorine content, Make full use of expensive fluorine raw materials; (2) because a variety of structural groups can be substituted on propylene oxide, so that the raw material structure can be selected according to the next reaction with the side chain fluorine-containing copolyether diol, One step is to copolymerize the propylene oxide monomer with the same solubility parameter
  • the problem of severe phase separation and incompatibility (3)
  • the side chain fluorine-containing copolyether glycol is easily dissolved in a non-toxic or low-toxic solvent which is industrially versatile and inexpensive, which can be largely Low processing costs, reduce pollution processing environment.
  • the side chain fluorine-containing copolyether diols provided by the present invention are extremely convenient in various subsequent uses, and the space for the use of such polyether diols is also expanded to a considerable extent.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyethers (AREA)

Abstract

L'invention concerne un copolyétherglycol à chaîne latérale fluorée, facilement soluble, copolymérisé à partir d'un perfluoralkylglycidyléther et d'un éther polycyclique, préparé au moyen d'une réaction de copolymérisation entre un perfluoralkylglycidyléther, un oxyde de propylène substitué et de l'oxétanne ou du tétrahydrofuranne. La présente invention peut synthétiser des copolyétherglycols à chaîne latérale fluorées ayant différentes teneurs en fluor par changement de la proportion de la matière première, utilisant en totalité la matière première fluor ; en outre, des oxydes de propylène substitués comportant différents groupes substituants peuvent être sélectionnés en fonction de l'utilisation ultérieure de la réaction du copolyétherglycol à chaîne latérale fluorée, en résolvant le problème d'une importante séparation des phases et d'une mise en œuvre malcommode pendant la mise en œuvre des composés fluorés organiques ; en outre, ce type de copolyétherglycol à chaîne latérale fluorée est aisément soluble dans des solvants non toxiques ou à faible toxicité, universels à l'échelle industrielle et bon marché, ce qui peut grandement réduire les coûts de mise en œuvre, et réduire la pollution de l'environnement de la mise en œuvre. En résumé, le copolyétherglycol à chaîne latérale fluorée fourni par la présente invention est très commode pour différentes utilisations ultérieures, et élargit dans une très grande mesure l'espace d'utilisation de ce type de polyétherglycol.
PCT/CN2018/078672 2017-03-16 2018-03-12 Copolyétherglycol à chaîne latérale fluorée facilement soluble, copolymerisé à partir de perfluoralkylglycidyléther et d'un éther polycyclique WO2018166413A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201710155902.6 2017-03-16
CN201710155902.6A CN106832246B (zh) 2017-03-16 2017-03-16 一种由全氟烷基缩水甘油醚与多元环醚共聚的易溶侧链含氟共聚醚二醇

Publications (1)

Publication Number Publication Date
WO2018166413A1 true WO2018166413A1 (fr) 2018-09-20

Family

ID=59144808

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2018/078672 WO2018166413A1 (fr) 2017-03-16 2018-03-12 Copolyétherglycol à chaîne latérale fluorée facilement soluble, copolymerisé à partir de perfluoralkylglycidyléther et d'un éther polycyclique

Country Status (2)

Country Link
CN (1) CN106832246B (fr)
WO (1) WO2018166413A1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106832246B (zh) * 2017-03-16 2018-09-04 南京信息工程大学 一种由全氟烷基缩水甘油醚与多元环醚共聚的易溶侧链含氟共聚醚二醇
CN109337063A (zh) * 2018-10-13 2019-02-15 郑州博物馆 一种用于文物粘接剂的端羟基聚醚合成方法
CN110041818A (zh) * 2019-04-23 2019-07-23 南京信息工程大学 一种耐溶剂耐腐蚀的超疏水、疏油自清洁涂层及其制备方法
CN110003433A (zh) * 2019-04-23 2019-07-12 南京信息工程大学 一种单组分常温自交联含氟聚氨酯涂层材料及其制备方法
CN111116890A (zh) * 2019-12-12 2020-05-08 西南科技大学 聚五氟丙基缩水甘油醚及其用途和制备方法
CN117887341B (zh) * 2023-12-26 2025-08-19 安庆龙驰氟硅新材料有限公司 非硅离型剂组合物、涂布方法及其长链烷基聚醚制备方法

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2447132A1 (fr) * 2001-05-14 2002-11-21 Omnova Solutions Inc. Surfactants polymeres derives de monomeres cycliques possedant des groupes lateraux de carbone fluore
CN1861662A (zh) * 2006-05-18 2006-11-15 中国科学技术大学 一种含氟聚醚二元醇的制备方法
WO2011075177A1 (fr) * 2009-12-17 2011-06-23 Invista Technologies S.A.R.L. Procédé de fabrication d'un copolyéther glycol intégré
CN103709388A (zh) * 2013-12-27 2014-04-09 南京信息工程大学 一种全氟取代环氧乙烷与环醚的共聚二醇及其制备方法
CN103772692A (zh) * 2013-12-27 2014-05-07 南京信息工程大学 一种全氟烷基缩水甘油醚与环醚的共聚二醇及其制备方法
US20140323772A1 (en) * 2013-04-25 2014-10-30 Invista North America S.A R.L. Polyether glycol manufacturing process
CN106832246A (zh) * 2017-03-16 2017-06-13 南京信息工程大学 一种由全氟烷基缩水甘油醚与多元环醚共聚的易溶侧链含氟共聚醚二醇
CN107022072A (zh) * 2017-03-16 2017-08-08 孔庆刚 一种由全氟取代环氧乙烷与多元环醚共聚的易溶侧链含氟聚醚二醇

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101824130B (zh) * 2009-12-31 2011-05-04 广东银洋树脂有限公司 一种软段侧链含氟水性聚氨酯的制备方法

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2447132A1 (fr) * 2001-05-14 2002-11-21 Omnova Solutions Inc. Surfactants polymeres derives de monomeres cycliques possedant des groupes lateraux de carbone fluore
CN1861662A (zh) * 2006-05-18 2006-11-15 中国科学技术大学 一种含氟聚醚二元醇的制备方法
WO2011075177A1 (fr) * 2009-12-17 2011-06-23 Invista Technologies S.A.R.L. Procédé de fabrication d'un copolyéther glycol intégré
US20140323772A1 (en) * 2013-04-25 2014-10-30 Invista North America S.A R.L. Polyether glycol manufacturing process
CN103709388A (zh) * 2013-12-27 2014-04-09 南京信息工程大学 一种全氟取代环氧乙烷与环醚的共聚二醇及其制备方法
CN103772692A (zh) * 2013-12-27 2014-05-07 南京信息工程大学 一种全氟烷基缩水甘油醚与环醚的共聚二醇及其制备方法
CN106832246A (zh) * 2017-03-16 2017-06-13 南京信息工程大学 一种由全氟烷基缩水甘油醚与多元环醚共聚的易溶侧链含氟共聚醚二醇
CN107022072A (zh) * 2017-03-16 2017-08-08 孔庆刚 一种由全氟取代环氧乙烷与多元环醚共聚的易溶侧链含氟聚醚二醇

Also Published As

Publication number Publication date
CN106832246B (zh) 2018-09-04
CN106832246A (zh) 2017-06-13

Similar Documents

Publication Publication Date Title
WO2018166413A1 (fr) Copolyétherglycol à chaîne latérale fluorée facilement soluble, copolymerisé à partir de perfluoralkylglycidyléther et d'un éther polycyclique
CA2464643C (fr) Procedes de production d'un compose comportant un groupe fluorosulfonyle et un compose obtenu a partir du compose comportant un groupe fluorosulfonyle
US4163115A (en) Preparation of esters of poly-(tetramethylene ether) glycol
JP3989548B2 (ja) 環式エーテルの重合法
JPH0613605B2 (ja) 分子末端に不飽和基を含有する分子量分布の狭いポリアルキレンオキシド
CN108659212B (zh) 一种含氟聚醚二元醇的制备方法
US20090030175A1 (en) Process for producing fluoropolymer by ring-opening polymerization of fluorinated epoxy compound
KR102613107B1 (ko) 고체 전해질 및 전지
CN109180937A (zh) 一种制备脂肪族聚硫醚的方法
JP2008138219A (ja) フッ素化アリルエーテル重合体の製造方法
JPWO2002064648A1 (ja) 含フッ素化合物、含フッ素ポリマー及びその製造方法
US9796812B2 (en) Polymers and processes for preparing the polymers
JPS63154736A (ja) オリゴオキシエチレン側鎖を有するポリエーテル共重合体の製法
US3205183A (en) Process for preparing polymeric oxetanes using hydrocarbonaluminum chelates as catalysts
CN107022072B (zh) 一种由全氟取代环氧乙烷与多元环醚共聚的易溶侧链含氟聚醚二醇
JPS584053B2 (ja) シヨクバイトシテ ｈｍｆ６ サンノ トリアルキルオキソニウムエンオ モチイル エピハロヒドリンノ ジユウゴウホウホウ
JP2003509510A (ja) 親二酸化炭素性化合物及びその合成方法
CN110105540A (zh) 一种缩水甘油酯型自固化环氧树脂的制备方法
CN114133553B (zh) 一种具有交替多嵌段结构的3,3-双叠氮甲基氧杂环丁烷-乙二醇含能共聚醚及其合成方法
US2873258A (en) Polymerization process for olefin oxides
Umezawa et al. Copolymerization of 3, 3, 3-trifluoro-1, 2-epoxypropane with 1, 2-epoxypropane using organozinc compounds
US3752777A (en) Polymers of 2-(fluorophenyl)-hexafluoro-2-propyl glycidyl ether
US3183210A (en) Polymerization of aldehyde by organometallic compound
CN117887062B (zh) 一种可控合成低分子量窄分布聚醚多元醇的方法
US3272889A (en) Epoxide copolymers

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 18767387

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 18767387

Country of ref document: EP

Kind code of ref document: A1