GB785229A - Improvements in and relating to the production of alkylene oxide polymers - Google Patents

Improvements in and relating to the production of alkylene oxide polymers

Info

Publication number
GB785229A
GB785229A GB345455A GB345455A GB785229A GB 785229 A GB785229 A GB 785229A GB 345455 A GB345455 A GB 345455A GB 345455 A GB345455 A GB 345455A GB 785229 A GB785229 A GB 785229A
Authority
GB
Grant status
Application
Patent type
Prior art keywords
aluminium
diethyl
ethylene oxide
metal
oxide
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
GB345455A
Inventor
David Gordon Stewart
Dhafir Yusef Waddan
Edward Teggin Borrows
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.)
PETROCHEMICALS Ltd
Original Assignee
PETROCHEMICALS Ltd
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

Links

Classifications

    • 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
    • C08G65/04Macromolecular 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
    • C08G65/06Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
    • C08G65/08Saturated oxiranes
    • C08G65/10Saturated oxiranes characterised by the catalysts used
    • C08G65/12Saturated oxiranes characterised by the catalysts used containing organo-metallic compounds or metal hydrides
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D319/00Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/101,4-Dioxanes; Hydrogenated 1,4-dioxanes
    • C07D319/121,4-Dioxanes; Hydrogenated 1,4-dioxanes not condensed with other rings
    • 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
    • C08G65/04Macromolecular 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
    • C08G65/06Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
    • C08G65/08Saturated oxiranes
    • 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
    • C08G65/04Macromolecular 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
    • C08G65/06Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
    • C08G65/08Saturated oxiranes
    • C08G65/10Saturated oxiranes characterised by the catalysts 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
    • 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
    • C08G65/2642Macromolecular 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 catalyst used
    • C08G65/2645Metals or compounds thereof, e.g. salts
    • C08G65/2651Alkaline earth metals or compounds thereof
    • 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
    • C08G65/2642Macromolecular 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 catalyst used
    • C08G65/2645Metals or compounds thereof, e.g. salts
    • C08G65/2654Aluminium or boron; Compounds thereof

Abstract

Alkylene oxide polymers of high molecular weight suitable for use as thickening agents and for processing into thin water-soluble films are obtained by reacting an alkylene oxide, particularly ethylene and propylene oxide, in presence of a catalyst of formula MeRR1x, where Me is a metal of the II or III Groups of the Periodic System, particularly Mg, Al, or Zn, R is a hydrocarbon radical and R1x are x members selected from hydrogen, halogens, hydrocarbon radicals, alkoxy radicals and secondary amino radicals and x is the valency of the metal Me minus one. Examples of the catalysts are triethyl aluminium, tri-isobutyl aluminium, trioctyl aluminium, di - isobutyl aluminium hydride, diethyl aluminium ethoxide, diethyl aluminium chloride, ethyl aluminium dibutoxide, diethyl piperidyl aluminium and similar magnesium and zinc compounds. During the polymerization dioxane and the tetramer of ethylene oxide are formed and can be separated by fractionation. Reaction temperatures of 0-200 DEG C. and pressures up to 40 atmospheres are employed. The polymerization may be carried out in presence of solvents, e.g. aliphatic aromatic and chlorinated hydrocarbons or ethers. In examples: (1) gaseous ethylene oxide is passed into a solution of triethyl aluminium in benzene, the mixture being cooled and maintained at 0 DEG C. for five days; excess ethylene oxide was distilled off and the polymer precipitated by addition of petroleum ether; (6) liquid ethylene oxide in benzene and diethyl magnesium were heated at 110 DEG C. for 65 hours; (10) 1,2-propylene oxide in hexane was added dropwise to a solution of triethyl aluminium in hexane; (18) liquid ethylene oxide was added to a solution of tri-iso-butyl aluminium in benzene and heated in an autoclave at 100 DEG C. The product was diluted with benzene, unreacted oxide distilled off and the solution added to petroleum ether to precipitate the polymer. Dioxane was distilled from the filtrate and the residue was distilled to recover the cyclic tetramer.ALSO:The invention comprises the cyclic tetramer of ethylene oxide <FORM:0785229/IV (a)/1> which is obtained along with dioxane and higher polymers by polymerizing ethylene oxide in presence of catalysts of formula MeR.R1x where Me is a metal of Group II or III, R is an hydrocarbon radical and R1x and x members selected from hydrogen, halogens, hydrocarbon radicals, alkoxy radicals and secondary amino radicals, and x is the valency of the metal Me minus one. Examples of the catalysts are triethyl aluminium, tri-isobutyl aluminium, trioctyl aluminium, di-isobutyl aluminium hydride, diethyl aluminium ethoxide, diethyl aluminium chloride, ethyl aluminium dibutoxide, diethyl piperidyl aluminium, diethyl zinc, ethyl zinc butoxide, diethyl magnesium. Reaction temperatures from 0-200 DEG C. and pressures up to 40 atmospheres may be employed. The alkylene oxide, viz. ethylene oxide, is preferably added to a solution of the catalyst in benzene or diethyl ether. The resulting polymeric material may be treated to remove catalyst therefrom by precipitating the metal (Me) as hydroxide or by extracting the metal as a water-soluble salt by treatment with aqueous acid. The remaining polymeric material is preferably separated into a lower molecular weight and a higher molecular weight polymer fraction (comprising dioxane and mainly non-cyclic polymer), or the cyclic tetramer of ethylene oxide being recovered from the lower molecular weight polymer fraction.
GB345455A 1955-02-04 1955-02-04 Improvements in and relating to the production of alkylene oxide polymers Expired GB785229A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
GB345555A GB785053A (en) 1955-02-04 1955-02-04 Improvements in or relating to the production of alkylene oxide polymers
GB4016358A GB854930A (en) 1955-02-04 1958-12-12 Improvements in or relating to the production of alkylene oxide polymers
GB4086858A GB875954A (en) 1955-02-04 1958-12-18 Improvements in or relating to the production of polymeric material from monomeric epoxy compounds

Publications (1)

Publication Number Publication Date
GB785229A true true GB785229A (en) 1957-10-23

Family

ID=62527897

Family Applications (4)

Application Number Title Priority Date Filing Date
GB345455A Expired GB785229A (en) 1955-02-04 1955-02-04 Improvements in and relating to the production of alkylene oxide polymers
GB345555A Expired GB785053A (en) 1955-02-04 1955-02-04 Improvements in or relating to the production of alkylene oxide polymers
GB4016358A Expired GB854930A (en) 1955-02-04 1958-12-12 Improvements in or relating to the production of alkylene oxide polymers
GB4086858A Expired GB875954A (en) 1955-02-04 1958-12-18 Improvements in or relating to the production of polymeric material from monomeric epoxy compounds

Family Applications After (3)

Application Number Title Priority Date Filing Date
GB345555A Expired GB785053A (en) 1955-02-04 1955-02-04 Improvements in or relating to the production of alkylene oxide polymers
GB4016358A Expired GB854930A (en) 1955-02-04 1958-12-12 Improvements in or relating to the production of alkylene oxide polymers
GB4086858A Expired GB875954A (en) 1955-02-04 1958-12-18 Improvements in or relating to the production of polymeric material from monomeric epoxy compounds

Country Status (6)

Country Link
US (2) US2870099A (en)
BE (1) BE544935A (en)
DE (1) DE1109901B (en)
FR (1) FR1146098A (en)
GB (4) GB785229A (en)
NL (1) NL204193A (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1130599B (en) * 1958-05-29 1962-05-30 Hercules Powder Co Ltd A process for the homo- or copolymerization of monomeric epoxy compounds
DE1131021B (en) * 1958-09-26 1962-06-07 ? A process for the preparation of polyethers on Alkylenoxydbasis
DE1149534B (en) * 1959-04-13 1963-05-30 Union Carbide Corp A process for preparing Epoxydpolymerisaten
US3294848A (en) * 1963-08-05 1966-12-27 Wyandotte Chemicals Corp Surface active agents from organometallic compounds utilizing a friedelcrafts catalyst
US3321533A (en) * 1963-08-05 1967-05-23 Wyandotte Chemicals Corp Surface active agents from organometallic compounds
DE1520038B (en) * 1960-03-31 1971-07-29 Hercules Inc A process for the polymerization of epoxides
US3760005A (en) * 1971-06-02 1973-09-18 Dow Chemical Co Cyclic polyethers as catalyst activators in the alkalicatalyzed reaction of alkylene oxides
US4562272A (en) * 1981-03-27 1985-12-31 Union Carbide Corporation Process for preparing cyclic polyethers

Families Citing this family (70)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3127371A (en) * 1964-03-31 Polymerization of oxirane
US3078280A (en) * 1963-02-19 Thehx molecule and process of making
BE566483A (en) * 1957-04-05
NL226437A (en) * 1957-04-08
US3271328A (en) * 1957-07-30 1966-09-06 Union Carbide Corp Polymerization of epoxides in the presence of aluminum alkylate as catalyst
US2916463A (en) * 1958-01-02 1959-12-08 Monsanto Chemicals Crystalline polystyrene oxide homopolymers
US3219591A (en) * 1958-05-29 1965-11-23 Hercules Powder Co Ltd Organoaluminum oxide catalyst composition
US3288750A (en) * 1958-07-03 1966-11-29 Gen Tire & Rubber Co Polymerization of phenyl glycidyl ether
US3031439A (en) * 1958-11-06 1962-04-24 Union Carbide Corp Co-polymerization of alkylene oxide and vinyl epoxy compounds
GB937164A (en) * 1958-11-24 1963-09-18 Gen Tire & Rubber Co Polymerization of alkylene oxides
US3100750A (en) * 1958-11-26 1963-08-13 Union Carbide Corp Process for polymerization of vicinal epoxides
US3062755A (en) * 1958-12-29 1962-11-06 Union Carbide Corp Polymerization of epoxides
US3167519A (en) * 1958-12-29 1965-01-26 Union Carbide Corp Polymerization of epoxides
US3116271A (en) * 1959-01-30 1963-12-31 Fmc Corp Polymerization of esters of acrylic and methacrylic acid
US3135705A (en) * 1959-05-11 1964-06-02 Hercules Powder Co Ltd Polymeric epoxides
US3135706A (en) * 1959-05-11 1964-06-02 Hercules Powder Co Ltd Polymeric epoxides
US3032445A (en) * 1959-06-24 1962-05-01 Union Carbide Corp Tobacco smoke filters
US3030316A (en) * 1959-06-29 1962-04-17 Union Carbide Corp Polymerization of epoxides
US3030315A (en) * 1959-06-29 1962-04-17 Union Carbide Corp Polymerization of epoxides
US3275598A (en) * 1959-07-01 1966-09-27 Union Carbide Corp Polymerization of oxirane monoepoxides in the presence of an organometallic compoundand an alcohol
US3399149A (en) * 1959-07-01 1968-08-27 Union Carbide Corp Polymerization of oxirane monoepoxides using an organometallic compound with water as cocatalysts
US3398119A (en) * 1959-07-01 1968-08-20 Union Carbide Corp Polymerization of oxirane monoepoxides using an organometallic compound with a phenolas cocatalysts
US3058922A (en) * 1959-09-30 1962-10-16 Hercules Powder Co Ltd Polymers of methallyl chloride epoxide
US3284374A (en) * 1960-03-05 1966-11-08 Nippon Carbide Kogyo Kk Process for polymerizing olefin oxides with a catalyst consisting of an organozinc compound and an amine
NL263069A (en) * 1960-03-31
US3205183A (en) * 1960-04-08 1965-09-07 Hercules Powder Co Ltd Process for preparing polymeric oxetanes using hydrocarbonaluminum chelates as catalysts
US3218269A (en) * 1960-05-13 1965-11-16 Hercules Powder Co Ltd Polymerization of epoxides with an alkylaluminum-trialkyl orthovanadate catalyst
GB914614A (en) * 1960-06-01 1963-01-02 Gen Electric Co Ltd Improvements in or relating to nuclear fuel elements
US3214387A (en) * 1960-06-10 1965-10-26 Union Carbide Corp Preparation of catalysts for the polymerization of epoxides
US3058923A (en) * 1960-07-01 1962-10-16 Hercules Powder Co Ltd Polymerization of epihalohydrins
US3065187A (en) * 1960-07-26 1962-11-20 Hercules Powder Co Ltd Poly(2, 3-epoxybutane)
US3355400A (en) * 1960-09-26 1967-11-28 Union Carbide Corp Polyether-lignin compositions
DE1302610B (en) * 1961-01-18 The General Tire & Rubber Co
GB1009953A (en) * 1961-05-25 1965-11-17 Sumitomo Chemical Co Method for polymerizing olefin oxides
BE619439A (en) * 1961-06-29
US3354097A (en) * 1961-06-29 1967-11-21 Hercules Inc Unsupported film of poly
NL280936A (en) * 1961-07-14
US3244646A (en) * 1962-01-04 1966-04-05 Socony Mobil Oil Co Inc Polymerization of epoxides using as catalyst a metal alkoxide-phosphorous acid reaction product
US3205207A (en) * 1962-01-29 1965-09-07 Hercules Powder Co Ltd Sulfur vulcanizable oxetane and oxetane-oxirane copolymers
US3178389A (en) * 1962-04-19 1965-04-13 Goodrich Co B F Non-scorching curable carboxylic polymer compositions
US3194772A (en) * 1962-09-21 1965-07-13 Olin Mathieson Process for copolymerizing tetrahydrofuran with an epoxide monomer
US3313740A (en) * 1962-09-26 1967-04-11 Gen Tire & Rubber Co Expoxide polymerization catalysts, their preparation and their use
US3251784A (en) * 1962-10-18 1966-05-17 Wyandotte Chemicals Corp Production of high molecular weight oxide polymers using organometallic catalyst and halogen cocatalyst
US3489728A (en) * 1963-03-27 1970-01-13 Union Carbide Corp Process of preparing polymers of 1,2-alkylene sulfides
US3337487A (en) * 1963-07-29 1967-08-22 Hercules Inc Reactive end-group polymers and preparation thereof
US3444102A (en) * 1963-09-21 1969-05-13 Seitetsu Kagaku Co Ltd Process for the production of a high molecular weight polymer of an epoxide using a three component catalyst comprising an organozinc compound,an organomagnesium compound and water
US3427259A (en) * 1963-10-16 1969-02-11 Union Carbide Corp Polymerizing of oxirane monoepoxides in the presence of a reaction product of an organometallic compound and a polyoxyalkylene glycol
US3497463A (en) * 1963-10-28 1970-02-24 Dow Chemical Co Polymerization of alkylene oxides with catalyst system comprising a hindered amine
US3234251A (en) * 1963-11-29 1966-02-08 Union Carbide Corp Polymerization catalysts which are the solid reaction products of organo-metallic compounds and ketones
NL137358C (en) * 1963-12-13
US3280045A (en) * 1964-02-26 1966-10-18 Hercules Inc Process for polymerizing epoxides with an alkyl aluminum compound
US3311570A (en) * 1964-03-27 1967-03-28 Hercules Inc Polymers and copolymers of 1, 1, 1-trihalo-3, 4-epoxybutanes
US3362918A (en) * 1964-06-09 1968-01-09 Uniroyal Inc Method of polymerizing and copolymerizing propylene oxide
US3399150A (en) * 1964-10-15 1968-08-27 Nippon Oil Co Ltd Process for polymerizing olefin oxides and catalyst compositions comprising an organo-metallic compound with a metal carbonate or sulfate therefor
US3332913A (en) * 1964-11-02 1967-07-25 Union Carbide Corp Thermally stable copolymers of aldehydes and epoxides
US3455847A (en) * 1965-08-25 1969-07-15 Maruzen Petrochem Co Ltd Polymerization of epoxides using a new catalyst derived from the reaction of organozinc with nitroso compound
US3337477A (en) * 1965-10-20 1967-08-22 Hercules Inc Diol of poly(cyclohexene oxide)
US3462379A (en) * 1965-12-02 1969-08-19 Dow Chemical Co Purification of poly(alkylene oxides)
US3459685A (en) * 1967-03-28 1969-08-05 Jefferson Chem Co Inc Polymerization of cyclic alkylene oxides with catalyst systems of a polymeric aluminum alcoholate and an organometallic
US3448064A (en) * 1967-08-21 1969-06-03 Jefferson Chem Co Inc Polymerization of alkylene oxides using a binary catalyst system containing an organometallic compound and boric acid
US3422040A (en) * 1967-08-21 1969-01-14 Jefferson Chem Co Inc Catalytic polymerization of cyclic alkylene oxides
US3496238A (en) * 1967-11-20 1970-02-17 Wyandotte Chemicals Corp Method of preparing low molecular weight isotactic polypropylene glycols and catalyst system therefor
US4511742A (en) * 1982-08-30 1985-04-16 The B. F. Goodrich Company Extraction of oligomers from polymers of epihalohydrin
US4568774A (en) * 1982-09-02 1986-02-04 Vista Chemical Company Catalysts for alkoxylation reactions
US4650853A (en) * 1985-11-15 1987-03-17 The Dow Chemical Company Process of polymerizing epoxides in solvent mixtures to form granular polymer products
CA1318740C (en) * 1987-04-17 1993-06-01 Simon Hsiao-Pao Yu Copolymers of ethylene oxide as antistatic additives
US6369159B1 (en) 1987-05-13 2002-04-09 Pdm Holdings Corp. Antistatic plastic materials containing epihalohydrin polymers
GB0305817D0 (en) * 2003-03-13 2003-04-16 Ic Innovations Ltd Polymerisation initiators
WO2015077211A1 (en) * 2013-11-22 2015-05-28 Dow Global Technologies Llc Zinc catalyst / additive system for the polymerization of epoxide monomers
KR20160089380A (en) * 2013-11-22 2016-07-27 다우 글로벌 테크놀로지스 엘엘씨 Zinc catalyst/additive system for the polymerization of epoxide monomers

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE597496C (en) * 1929-11-27 1934-05-25 Ig Farbenindustrie Ag A process for the preparation of polymerization products of AEthylenoxyds
GB646292A (en) * 1946-08-31 1950-11-22 Bataafsche Petroleum Extreme pressure lubricant
FR1007707A (en) * 1948-03-23 1952-05-09 Basf Ag A process for producing polymers of alkylene oxides
BE510597A (en) * 1951-05-31
US2706189A (en) * 1952-06-05 1955-04-12 Dow Chemical Co Solid polymers of propylene oxide

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1130599B (en) * 1958-05-29 1962-05-30 Hercules Powder Co Ltd A process for the homo- or copolymerization of monomeric epoxy compounds
DE1131021B (en) * 1958-09-26 1962-06-07 ? A process for the preparation of polyethers on Alkylenoxydbasis
DE1149534B (en) * 1959-04-13 1963-05-30 Union Carbide Corp A process for preparing Epoxydpolymerisaten
DE1520038B (en) * 1960-03-31 1971-07-29 Hercules Inc A process for the polymerization of epoxides
US3294848A (en) * 1963-08-05 1966-12-27 Wyandotte Chemicals Corp Surface active agents from organometallic compounds utilizing a friedelcrafts catalyst
US3321533A (en) * 1963-08-05 1967-05-23 Wyandotte Chemicals Corp Surface active agents from organometallic compounds
US3760005A (en) * 1971-06-02 1973-09-18 Dow Chemical Co Cyclic polyethers as catalyst activators in the alkalicatalyzed reaction of alkylene oxides
US4562272A (en) * 1981-03-27 1985-12-31 Union Carbide Corporation Process for preparing cyclic polyethers

Also Published As

Publication number Publication date Type
GB785053A (en) 1957-10-23 application
US2870100A (en) 1959-01-20 grant
GB854930A (en) 1960-11-23 application
DE1109901B (en) 1961-06-29 application
BE544935A (en) 1900-01-01 grant
NL204193A (en) 1900-01-01 application
GB875954A (en) 1961-08-23 application
US2870099A (en) 1959-01-20 grant
FR1146098A (en) 1957-11-06 grant

Similar Documents

Publication Publication Date Title
US3761458A (en) Polymerization process and products
US3290277A (en) Amino-containing block polymers of ethylene and alpha-alkyl styrene
US3347840A (en) Polymerization process
US3222326A (en) Polymers of alkylene thioethers
US4542199A (en) Process for the preparation of polyolefins
US2551813A (en) Free radical addition of h2s to olefins
US2721189A (en) Polymeric bicyclo-(2, 2, 1)-2-heptene
US2985633A (en) Polymerization of ethylene with organoboron compounds treated with oxygen
US5308815A (en) Heterogeneous methylaluminoxane catalyst system
US4314912A (en) High efficiency, high temperature catalyst for polymerizing olefins
US3644315A (en) Moisture-curable polymers
US3097194A (en) Process for preparing phosphorylated elastomeric copolymers of ethylene and propylene
US4777219A (en) Carboxylate containing modified acrylamide polymers
US3701763A (en) Process for polymerization of olefins and catalysts therefor
US4006101A (en) Polymerization of olefins and catalysts therefor
US3718636A (en) Catalysts and process for the polymerization of olefins
US2799668A (en) Novel polymers of ethylene and bicyclo (2.2.1)-2-heptenes
US3394118A (en) Polymerization catalyst and process
US3932307A (en) Tetra(neophyl) zirconium and its use in process for the polymerization of olefins
US3629216A (en) Process for the polymerization of olefins
US2959607A (en) Higher aluminum alkyls and products therefrom
US4011383A (en) Tetra(neophyl) zirconium and its use in process for the polymerization of olefins
US3050471A (en) Polymerization catalyst
US3046255A (en) Process for preparing polycarbonates
US3272786A (en) Polymerization process using chain-transfer agents