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GB854958A - Copolymerising mono-epoxides with tetrahydrofurane - Google Patents

Copolymerising mono-epoxides with tetrahydrofurane

Info

Publication number
GB854958A
GB854958A GB8313/58A GB831358A GB854958A GB 854958 A GB854958 A GB 854958A GB 8313/58 A GB8313/58 A GB 8313/58A GB 831358 A GB831358 A GB 831358A GB 854958 A GB854958 A GB 854958A
Authority
GB
United Kingdom
Prior art keywords
acid
tetrahydrofurane
copolymerized
hydrocarbons
catalyst
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.)
Expired
Application number
GB8313/58A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
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 Bayer AG filed Critical Bayer AG
Publication of GB854958A publication Critical patent/GB854958A/en
Expired legal-status Critical Current

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
    • C08G65/20—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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Epoxy Compounds (AREA)

Abstract

A monoepoxide is copolymerized with tetrahydrofurane in the presence of a compound having one or more reactive hydrogen atoms and, as catalyst, an acid-activated natural or synthetic bleaching earth. Specified epoxides are ethylene, propylene, butylene, amylene, styrene and phenoxypropene oxides and epichlorhydrin. Suitable bleaching earths are natural or synthetic montmorillonite and kaolinite, e.g. as sold under the name "Tonsil". The activating acid is generally a mineral acid such as sulphuric or hydrochloric acid. By "compounds having reactive hydrogen atoms" is meant any compound which gives a positive Zerewitinoff test. Examples are mono- and poly-hydric alcohols, saturated and unsaturated organic acids, mercaptans, phenols, acid imides and enolic compounds. Polymerization is effected at room temperatures and diluents may be present, e.g. hydrocarbons, chloro-hydrocarbons, dioxane, and a liquid copolymer prepared from a previous polymerization. Elevated pressure is preferably employed. The products have molecular weights of about 300 to 5,000 or higher. The catalyst can be removed by mechanical or filtering means. Examples are given, in one of which, Example 7, propylene oxide and tetrahydrofurane are copolymerized in the presence of methacrylic acid and the unsaturated product is said to be polymerizable, e.g. with olefines. The polyglycol ethers are also useful starting materials for other plastic materials, e.g. polyurethanes, and for lubricants and fuel additives.
GB8313/58A 1957-03-14 1958-03-14 Copolymerising mono-epoxides with tetrahydrofurane Expired GB854958A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE854958X 1957-03-14

Publications (1)

Publication Number Publication Date
GB854958A true GB854958A (en) 1960-11-23

Family

ID=6788981

Family Applications (1)

Application Number Title Priority Date Filing Date
GB8313/58A Expired GB854958A (en) 1957-03-14 1958-03-14 Copolymerising mono-epoxides with tetrahydrofurane

Country Status (1)

Country Link
GB (1) GB854958A (en)

Cited By (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4139567A (en) * 1977-03-30 1979-02-13 E. I. Du Pont De Nemours And Company Method for preparing copolyether glycols
US4153786A (en) 1977-03-30 1979-05-08 E. I. Du Pont De Nemours And Company Method for preparing ester end-capped copolyether glycols
EP0004356A1 (en) * 1978-03-16 1979-10-03 E.I. Du Pont De Nemours And Company Polyurethanes prepared with tetrahydrofuran-alkylene oxide polymerizates having low oligomeric cyclic ether content, processes for preparing the same, and articles and fibers of the polyurethanes
EP0004536A1 (en) * 1978-03-16 1979-10-17 E.I. Du Pont De Nemours And Company Method for reducing the oligomeric cyclic ether content of a polymerizate
US4192943A (en) 1978-06-13 1980-03-11 E. I. Du Pont De Nemours And Company Method for reducing oligomeric cyclic ether content of a polymerizate
US4198464A (en) 1978-05-26 1980-04-15 Basf Wyandotte Corporation Fiber lubricants based upon ethylene oxide capped polyethers of tetrahydrofuran and ethylene oxide
US4228272A (en) 1979-03-27 1980-10-14 E. I. Du Pont De Nemours And Company Method of catalytically preparing tetrahydrofuran/alkylene oxide polymerizates using a montmorillonite clay as the catalyst
US4235751A (en) 1979-04-30 1980-11-25 E. I. Du Pont De Nemours And Company Modified montmorillonite clay catalyst
US4245004A (en) 1978-05-26 1981-01-13 Basf Wyandotte Corporation Ethoxylated polytetramethylene glycols as fiber lubricants
US4251654A (en) 1979-08-14 1981-02-17 E. I. Du Pont De Nemours And Company Copolyether glycols of tetrahydrofuran and alkylene oxides having low oligomeric cyclic ether content
US4259405A (en) 1980-01-15 1981-03-31 Basf Wyandotte Corporation Synthetic fibers lubricated with heteric copolymer of tetrahydrofuran and C3 to C4 alkylene oxide
US4329445A (en) 1979-04-30 1982-05-11 E. I. Du Pont De Nemours And Company Process for preparing a tetrahydrofuran-alkylene oxide copolymer with treated bentonite catalyst
EP0052213A1 (en) * 1980-11-14 1982-05-26 BASF Aktiengesellschaft Process for depolymerizing polytetramethylene ether glycols
US4374970A (en) 1981-07-07 1983-02-22 E. I. Du Pont De Nemours And Company Sulfur-modified copolyether glycols, a method for preparing them, and polyurethanes prepared therefrom
DE3326178A1 (en) * 1983-04-13 1984-10-18 Daicel Chemical Industries, Ltd., Sakai, Osaka POLYALKYLENAETHERGLYKOLCOPOLYMERS
EP0151766A3 (en) * 1984-01-21 1985-09-18 Basf Aktiengesellschaft Process for the preparation of carboxylic-acid diesters of polybutylene oxide-polyalkylene oxide glycols
EP0158060A1 (en) * 1984-02-28 1985-10-16 BASF Aktiengesellschaft Method of reducing the oligomeric cyclic ether content of polybutylene oxide-polyalkylene oxide glycols
US4564671A (en) * 1983-12-21 1986-01-14 Basf Aktiengesellschaft Continuous preparation of polyoxybutylene polyoxyalkylene glycols
US4585592A (en) * 1985-02-28 1986-04-29 Basf Aktiengesellschaft Reducing the content of oligomeric cyclic ethers in polyoxybutylene polyoxyalkylene glycols
US4638097A (en) * 1985-04-23 1987-01-20 Basf Aktiengesellschaft Reducing the content of cyclic oligomeric ethers in polytetramethylene ether glycols or polyoxybutylene polyoxyalkylene glycols
US4670519A (en) * 1985-02-15 1987-06-02 Basf Aktiengesellschaft Narrowing the molecular weight distribution of polytetrahydrofuran
US4728722A (en) * 1986-02-28 1988-03-01 Basf Aktiengesellschaft Preparation of polyoxybutylene polyoxyalkylene glycols having a narrow molecular weight distribution and a reduced content of oligomeric cyclic ethers
EP0241890A3 (en) * 1986-04-18 1989-03-08 BASF Aktiengesellschaft Process for the preparation of a polytetramethylene ether glycol diester having a lower colour index
US5210283A (en) * 1992-05-18 1993-05-11 Arco Chemical Technology, L.P. Synthesis of tetrahydrofuran polymers using calcined silica-alumina or beaching earth catalysts
US5218141A (en) * 1984-01-21 1993-06-08 Basf Aktiengesellschaft Preparation of polyoxybutylele polyoxyalkylene glycol dicarboxylates
US5426174A (en) * 1992-12-08 1995-06-20 Arco Chemical Technology, L.P. Hydroxy-functionalized polyoxyalkylene ether compositions derived from mixtures of C4 epoxides
US5561217A (en) * 1992-12-23 1996-10-01 Basf Aktiengesellschaft Preparation of polyether glycols
US20100267926A1 (en) * 2009-04-15 2010-10-21 Invista North America S.A.R.L Copolyether glycol manufacturing process
EP2419472A4 (en) * 2009-04-15 2013-01-23 Invista Tech Sarl PROCESS FOR THE PRODUCTION OF COPOLYETHER GLYCOL

Cited By (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4153786A (en) 1977-03-30 1979-05-08 E. I. Du Pont De Nemours And Company Method for preparing ester end-capped copolyether glycols
US4139567A (en) * 1977-03-30 1979-02-13 E. I. Du Pont De Nemours And Company Method for preparing copolyether glycols
EP0004356A1 (en) * 1978-03-16 1979-10-03 E.I. Du Pont De Nemours And Company Polyurethanes prepared with tetrahydrofuran-alkylene oxide polymerizates having low oligomeric cyclic ether content, processes for preparing the same, and articles and fibers of the polyurethanes
EP0004536A1 (en) * 1978-03-16 1979-10-17 E.I. Du Pont De Nemours And Company Method for reducing the oligomeric cyclic ether content of a polymerizate
US4245004A (en) 1978-05-26 1981-01-13 Basf Wyandotte Corporation Ethoxylated polytetramethylene glycols as fiber lubricants
US4198464A (en) 1978-05-26 1980-04-15 Basf Wyandotte Corporation Fiber lubricants based upon ethylene oxide capped polyethers of tetrahydrofuran and ethylene oxide
US4192943A (en) 1978-06-13 1980-03-11 E. I. Du Pont De Nemours And Company Method for reducing oligomeric cyclic ether content of a polymerizate
EP0006107B1 (en) * 1978-06-13 1983-11-23 E.I. Du Pont De Nemours And Company Method for reducing oligomeric cyclic ether content of a copolymerizate
US4228272A (en) 1979-03-27 1980-10-14 E. I. Du Pont De Nemours And Company Method of catalytically preparing tetrahydrofuran/alkylene oxide polymerizates using a montmorillonite clay as the catalyst
US4235751A (en) 1979-04-30 1980-11-25 E. I. Du Pont De Nemours And Company Modified montmorillonite clay catalyst
US4329445A (en) 1979-04-30 1982-05-11 E. I. Du Pont De Nemours And Company Process for preparing a tetrahydrofuran-alkylene oxide copolymer with treated bentonite catalyst
US4251654A (en) 1979-08-14 1981-02-17 E. I. Du Pont De Nemours And Company Copolyether glycols of tetrahydrofuran and alkylene oxides having low oligomeric cyclic ether content
US4259405A (en) 1980-01-15 1981-03-31 Basf Wyandotte Corporation Synthetic fibers lubricated with heteric copolymer of tetrahydrofuran and C3 to C4 alkylene oxide
EP0052213A1 (en) * 1980-11-14 1982-05-26 BASF Aktiengesellschaft Process for depolymerizing polytetramethylene ether glycols
US4374970A (en) 1981-07-07 1983-02-22 E. I. Du Pont De Nemours And Company Sulfur-modified copolyether glycols, a method for preparing them, and polyurethanes prepared therefrom
DE3326178A1 (en) * 1983-04-13 1984-10-18 Daicel Chemical Industries, Ltd., Sakai, Osaka POLYALKYLENAETHERGLYKOLCOPOLYMERS
US4564671A (en) * 1983-12-21 1986-01-14 Basf Aktiengesellschaft Continuous preparation of polyoxybutylene polyoxyalkylene glycols
EP0151766A3 (en) * 1984-01-21 1985-09-18 Basf Aktiengesellschaft Process for the preparation of carboxylic-acid diesters of polybutylene oxide-polyalkylene oxide glycols
US5218141A (en) * 1984-01-21 1993-06-08 Basf Aktiengesellschaft Preparation of polyoxybutylele polyoxyalkylene glycol dicarboxylates
EP0158060A1 (en) * 1984-02-28 1985-10-16 BASF Aktiengesellschaft Method of reducing the oligomeric cyclic ether content of polybutylene oxide-polyalkylene oxide glycols
US4670519A (en) * 1985-02-15 1987-06-02 Basf Aktiengesellschaft Narrowing the molecular weight distribution of polytetrahydrofuran
US4585592A (en) * 1985-02-28 1986-04-29 Basf Aktiengesellschaft Reducing the content of oligomeric cyclic ethers in polyoxybutylene polyoxyalkylene glycols
US4638097A (en) * 1985-04-23 1987-01-20 Basf Aktiengesellschaft Reducing the content of cyclic oligomeric ethers in polytetramethylene ether glycols or polyoxybutylene polyoxyalkylene glycols
US4728722A (en) * 1986-02-28 1988-03-01 Basf Aktiengesellschaft Preparation of polyoxybutylene polyoxyalkylene glycols having a narrow molecular weight distribution and a reduced content of oligomeric cyclic ethers
EP0241890A3 (en) * 1986-04-18 1989-03-08 BASF Aktiengesellschaft Process for the preparation of a polytetramethylene ether glycol diester having a lower colour index
US5210283A (en) * 1992-05-18 1993-05-11 Arco Chemical Technology, L.P. Synthesis of tetrahydrofuran polymers using calcined silica-alumina or beaching earth catalysts
US5426174A (en) * 1992-12-08 1995-06-20 Arco Chemical Technology, L.P. Hydroxy-functionalized polyoxyalkylene ether compositions derived from mixtures of C4 epoxides
US5561217A (en) * 1992-12-23 1996-10-01 Basf Aktiengesellschaft Preparation of polyether glycols
EP0687699A3 (en) * 1994-06-10 1996-01-17 Arco Chem Tech
US20100267926A1 (en) * 2009-04-15 2010-10-21 Invista North America S.A.R.L Copolyether glycol manufacturing process
EP2419472A4 (en) * 2009-04-15 2013-01-23 Invista Tech Sarl PROCESS FOR THE PRODUCTION OF COPOLYETHER GLYCOL
US8372946B2 (en) * 2009-04-15 2013-02-12 Invista North America S.A R.L. Copolyether glycol manufacturing process

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