GB1018776A - Polymeric materials and their preparation - Google Patents

Polymeric materials and their preparation

Info

Publication number
GB1018776A
GB1018776A GB2845963A GB2845963A GB1018776A GB 1018776 A GB1018776 A GB 1018776A GB 2845963 A GB2845963 A GB 2845963A GB 2845963 A GB2845963 A GB 2845963A GB 1018776 A GB1018776 A GB 1018776A
Authority
GB
United Kingdom
Prior art keywords
monoepoxide
diene
reacting
propylene oxide
epoxy
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
GB2845963A
Inventor
Eric Frow
Alec Victor Mercer
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.)
Shell Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij BV
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 Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Priority to GB2845963A priority Critical patent/GB1018776A/en
Priority to FR981863A priority patent/FR1401803A/en
Priority to BE650621D priority patent/BE650621A/xx
Priority to NL6408118A priority patent/NL6408118A/xx
Publication of GB1018776A publication Critical patent/GB1018776A/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
    • 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
    • C08G18/50—Polyethers having heteroatoms other than oxygen
    • C08G18/5003—Polyethers having heteroatoms other than oxygen having halogens
    • C08G18/5006—Polyethers having heteroatoms other than oxygen having halogens having chlorine and/or bromine atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/02—Preparation of ethers from oxiranes
    • C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/04—Saturated ethers
    • C07C43/12—Saturated ethers containing halogen
    • C07C43/126—Saturated ethers containing halogen having more than one ether bond
    • 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
    • C08G65/14—Unsaturated oxiranes
    • 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
    • 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
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
    • C08G65/323—Polymers modified by chemical after-treatment with inorganic compounds containing halogens
    • C08G65/3233—Molecular halogen

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Inorganic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Epoxy Resins (AREA)

Abstract

Poly-dihaloethers are prepared by reacting a vicinal epoxy compound which contains olefinic linkage with a nucleating agent and reacting the resulting polyether with either chlorine or bromine. The polyether polyol may also be an interpolymer of the olefinically unsaturated epoxy reactant and a saturated epoxy reactant. Suitable unsaturated epoxy compounds are aliphatic, alicyclic and glycidyl ethers; preferred are butadiene monoepoxide, 1,2-epoxy-2-methyl but-3-ene, diallyl monoepoxide, allylglycidyl ether, 1,2 - epoxycyclododeca - 5,9-diene and vinylcyclohexene monoepoxide. Suitable nucleating agents are polyhydric alcohols and phenols, and amines. Propylene oxide is the preferred saturated epoxide but others are specified. The examples describe the copolymerization of propylene oxide, using glycerol as initiator, with (1)-(3) allyl glycidyl ether, and (4) 1,2-epoxycyclododecane 5,9-diene; the products are brominated. The polydihaloethers may be reacted with polyisocyanates and polythioisocyanates to form foamed and non-foamed fire-retardant polyurethanes, preferably using the "one-shot" process. In Examples (5)-(11) the polydibromoethers of (1)-(4) are converted to polyurethane foams by reacting with p,p1-diphenylmethanediisocyanate in the presence of water and trichlorofluoromethane, triethylamine, triethylenediamine and a silicone oil.ALSO:Polydihaloethers are prepared by copolymerizing an olefinic unsaturated epoxy compound with a saturated vicinal epoxide in the presence of a nucleating agent and reacting the resulting polyether with either chlorine or bromine. Suitable unsaturated epoxy compounds are aliphatic, alicyclic and glycidyl ethers; preferred are butadiene monoepoxide, 1,2 - epoxy - 2 - methylbut - 3 - ene, diallyl monoepoxide, allylglycidyl ether, 1,2 - epoxycyclododecane - 5,9 - diene and vinylcyclohexene monoepoxide. Suitable nucleating agents are polyhydric alcohols and phenols, and amines. Propylene oxide is the preferred saturated epoxide, but others are specified. The examples describe the copolymerization of propylene oxide with (1)-(3) allyl glycidyl ether, and (4) 1,2 - epoxycyclododecane - 5,9 - diene, using glycerol as a nucleating agent; the products are brominated to form the corresponding poly-dibromo ethers.
GB2845963A 1963-07-18 1963-07-18 Polymeric materials and their preparation Expired GB1018776A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
GB2845963A GB1018776A (en) 1963-07-18 1963-07-18 Polymeric materials and their preparation
FR981863A FR1401803A (en) 1963-07-18 1964-07-16 Process for the preparation of a poly-dihaloether and use in polyurethanes
BE650621D BE650621A (en) 1963-07-18 1964-07-16
NL6408118A NL6408118A (en) 1963-07-18 1964-07-16

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2845963A GB1018776A (en) 1963-07-18 1963-07-18 Polymeric materials and their preparation

Publications (1)

Publication Number Publication Date
GB1018776A true GB1018776A (en) 1966-02-02

Family

ID=10275964

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2845963A Expired GB1018776A (en) 1963-07-18 1963-07-18 Polymeric materials and their preparation

Country Status (3)

Country Link
BE (1) BE650621A (en)
GB (1) GB1018776A (en)
NL (1) NL6408118A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011012230A (en) * 2009-07-06 2011-01-20 Asahi Organic Chemicals Industry Co Ltd Foamable composition for polyurethane foam and polyurethane foam
CN109265673A (en) * 2018-09-26 2019-01-25 南京林业大学 A kind of organosilicon modified polyether polyalcohol and its preparation method and application

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2553087B1 (en) * 1983-10-07 1985-11-29 Atochem CHLORO-BROMINATED POLYHYDROXYL COMPOUNDS, THEIR MANUFACTURING PROCESS AND THEIR APPLICATION TO RIGID FOAMS OF FLAME RETARDANT POLYURETHANES

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011012230A (en) * 2009-07-06 2011-01-20 Asahi Organic Chemicals Industry Co Ltd Foamable composition for polyurethane foam and polyurethane foam
CN109265673A (en) * 2018-09-26 2019-01-25 南京林业大学 A kind of organosilicon modified polyether polyalcohol and its preparation method and application
CN109265673B (en) * 2018-09-26 2020-03-31 南京林业大学 Organic silicon modified polyether polyol and preparation method and application thereof

Also Published As

Publication number Publication date
NL6408118A (en) 1965-01-19
BE650621A (en) 1965-01-18

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