GB975461A - Polyether elastomers - Google Patents

Polyether elastomers

Info

Publication number
GB975461A
GB975461A GB4064261A GB4064261A GB975461A GB 975461 A GB975461 A GB 975461A GB 4064261 A GB4064261 A GB 4064261A GB 4064261 A GB4064261 A GB 4064261A GB 975461 A GB975461 A GB 975461A
Authority
GB
United Kingdom
Prior art keywords
oxide
propylene oxide
copolymer
glycidyl
mixtures
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
GB4064261A
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.)
GAETANO GIOVANNI ANDREA PIRRON
GUIDO DOMENICO RIGHI
Original Assignee
GAETANO GIOVANNI ANDREA PIRRON
GUIDO DOMENICO RIGHI
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 GAETANO GIOVANNI ANDREA PIRRON, GUIDO DOMENICO RIGHI filed Critical GAETANO GIOVANNI ANDREA PIRRON
Publication of GB975461A publication Critical patent/GB975461A/en
Expired legal-status Critical Current

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
    • C08G65/22Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
    • 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
    • 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
    • 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
    • C08G65/14Unsaturated oxiranes

Landscapes

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

Abstract

The invention comprises vulcanizable polyether elastomers composed of polymerized epoxide monomers of which at least 50 mol per cent is styrene oxide or an alkylene oxide having not more than four carbon atoms, or a halogenated derivative of alkylene oxides, the elastomer being substantially amorphous, devoid of spherulite, and having an intrinsic viscosity greater than 3.0. They are prepared by polymerizing in the presence of zinc diethyl and water, either in the absence of a diluent or in presence of one of the following: benzene, toluene, xylene, or mixtures thereof with or without a minor portion by volume of a liquid aliphatic hydrocarbon diluent, benzaldehyde, an alkaldehyde with 2 to 7 carbon atoms, or mixtures thereof, with or without dilution with dioxane or a liquid aliphatic hydrocarbon. The mole ratio of water to zinc diethyl is in the range 0.5 to 1.5:1, preferably 1:1. Specified monomers are ethylene oxide, 1,2-propylene oxide-chloropropylene oxide 1,2-butylene oxide, 2,3-butylene oxide, isobutylene oxide, styrene oxide, and mixtures thereof. A minor portion, preferably 3.5 mol per cent, of an olefinically unsaturated epoxide can be added and copolymerized with the above oxides. Specified unsaturated epoxides are 1-butene-glycidyl ether, vinyl-glycidyl-ether, vinyl-thio-ethyl-glycidyl ether, glycidyl acrylate, glycidyl methacrylate, butadiene monoxide, vinyl-cyclohexene monoxide, allyl-glycidyl ether, and mixtures thereof. Preferably 1.3 moles of zinc diethyl per 100 moles of monomer is used, but as little as 0.2 moles is required. Vulcanization of the saturated elastomer is effected by a mixture of an organic peroxide and a conventional sulphur-bearing agent. In the case of polyethers containing unsaturation a single agent is sufficient. Specified peroxides are di-cumyl peroxide, di-tertiary-butyl hydroperoxide and 2,5-bis (tert.-butyl-peroxy)-2, 5-dimethyl hexane. The examples describe the preparation of: (1) poly-propylene oxide; (2) copolymer of propylene oxide and allyl glycidyl ether; (8) copolymer of propylene oxide and butadiene monoxide; (9) copolymer of propylene oxide and vinylcyclohexene monoxide; (10) copolymer of propylene oxide and glycidyl acrylate; (12) polymer of styrene oxide; (13) polymer of butylene oxide. In examples (18)-(20) poly propylene oxide is vulcanized in presence of various quantities of di-cumyl peroxide, sulphur, phenylb -naphthaline (as antioxidant), and carbon black (as reinforcing agent). In example (21) copolymer of example (7) is vulcanized in presence of sulphur, stearic acid, zinc oxide, carbon black, tetramethyl thiuram disulphide and tellurium diethyl dithiocarbonate (the latter two being accelerators). Properties of the rubbers are also shown in the examples, and a comparison table of rubber of example (21) and several other known rubbers is given.
GB4064261A 1960-11-17 1961-11-14 Polyether elastomers Expired GB975461A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US6991560A 1960-11-17 1960-11-17

Publications (1)

Publication Number Publication Date
GB975461A true GB975461A (en) 1964-11-18

Family

ID=22091991

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4064261A Expired GB975461A (en) 1960-11-17 1961-11-14 Polyether elastomers

Country Status (3)

Country Link
BE (1) BE610449A (en)
GB (1) GB975461A (en)
NL (1) NL271539A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1873186A1 (en) * 2006-06-21 2008-01-02 Bayer MaterialScience AG Pendant acrylate and/or methacrylate-containing polyether monols and polyols

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1873186A1 (en) * 2006-06-21 2008-01-02 Bayer MaterialScience AG Pendant acrylate and/or methacrylate-containing polyether monols and polyols
CN103145972A (en) * 2006-06-21 2013-06-12 拜尔材料科学有限公司 Polyether monols and polyols containing pendant acrylate and/or methacrylate esters

Also Published As

Publication number Publication date
NL271539A (en)
BE610449A (en)

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