GB991453A - Epoxy alcohols and ethers - Google Patents

Epoxy alcohols and ethers

Info

Publication number
GB991453A
GB991453A GB3159361A GB3159361A GB991453A GB 991453 A GB991453 A GB 991453A GB 3159361 A GB3159361 A GB 3159361A GB 3159361 A GB3159361 A GB 3159361A GB 991453 A GB991453 A GB 991453A
Authority
GB
United Kingdom
Prior art keywords
compounds
alkyl
hydroxy
acid
formula
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
GB3159361A
Inventor
Angus John Duke
Bryan Dobinson
Lawrence Stewart Ainslie Smith
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.)
BASF Schweiz AG
Ciba ARL Ltd
Original Assignee
Ciba AG
Ciba ARL 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
Application filed by Ciba AG, Ciba ARL Ltd filed Critical Ciba AG
Priority to GB3159361A priority Critical patent/GB991453A/en
Publication of GB991453A publication Critical patent/GB991453A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
    • C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/14—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by free hydroxyl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
    • C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
    • C07D303/26—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds having one or more free hydroxyl radicals
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/24—Di-epoxy compounds carbocyclic

Landscapes

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

Abstract

The invention comprises mixtures of compounds of the general formula <FORM:0991453/C2/1> having an infra-red absorption band at about 850 cm.-1 but not at about 780 cm.-1, wherein R is hydrogen, alkyl, hydroxy alkyl, hydroxy alkoxyalkyl, polyhydroxyalkyl or hydroxy (polyalkoxy) alkyl, and in particular the mixtures of the above formula wherein R is H, CH3, CH2CH2OH which are made by reacting a mixture of compounds of the general formula <FORM:0991453/C2/2> wherein R1 is as above defined or acylated hydroxy, with a hypohalous acid, an acyl hypohalite, or a compound or mixture giving rise to hypohalous acid or acyl hypohalite under the conditions of the reaction and treating the halohydrin or halohydrin ester formed with a base. The preferred reagent is hypochlorous acid liberated in situ from a hypochlorite, preferably in the presence of a carboxylic acid, optionally in the presence of a surface-active agent. Specially useful is tertiary butyl hypochlorite in the presence of acetic or formic acid. The oxirane ring closure may be effected by the use of an alkali metal or alkaline earth metal oxide or hydroxide or quaternary ammonium hydroxide. The examples give synthesis of the mixtures of the compounds of Formula I wherein R is H, CH2CH2OH, CH3 using tertiary butyl hypochlorite/glacial acetic acid and effecting ring closure with alkali metal hydroxide, and of compounds of the formula I wherein R is H, starting with compounds of the Formula II wherein R1 is -CO.H and H using aqueous sodium hypochlorite in the presence of an emulsifying agent and hexoic, octoic or sulphuric acid in the halohydrin stage. The I.R. spectra of the products of the invention are compared with the isomeric ones obtained by the use of per-acids. Specification 991,452 is referred to.ALSO:Hardenable compositions comprise as reactive diluent a mixture of the 9 and 10 substituted dicyclopentadiene epoxides of the general formula <FORM:0991453/C3/1> wherein R is H, alkyl, hydroxyalkyl, hydroxyalkoxyalkyl, polyhydroxyalkyl or hydroxy-(polyalkoxy)-alkyl, said compounds showing an infra-red absorption band at about 850 cm.-1 but not at about 780 cm.-1, together with one or more di- or poly-epoxides and one or more hardening agents, many of which are listed. Specification 991,452 is referred to.
GB3159361A 1961-09-01 1961-09-01 Epoxy alcohols and ethers Expired GB991453A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3159361A GB991453A (en) 1961-09-01 1961-09-01 Epoxy alcohols and ethers

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3159361A GB991453A (en) 1961-09-01 1961-09-01 Epoxy alcohols and ethers

Publications (1)

Publication Number Publication Date
GB991453A true GB991453A (en) 1965-05-05

Family

ID=10325455

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3159361A Expired GB991453A (en) 1961-09-01 1961-09-01 Epoxy alcohols and ethers

Country Status (1)

Country Link
GB (1) GB991453A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4622349A (en) * 1983-02-07 1986-11-11 Union Carbide Corporation Blends of epoxides and monoepoxides
US4814361A (en) * 1983-02-07 1989-03-21 Union Carbide Corporation Blends of epoxides and monoepoxides

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4622349A (en) * 1983-02-07 1986-11-11 Union Carbide Corporation Blends of epoxides and monoepoxides
US4814361A (en) * 1983-02-07 1989-03-21 Union Carbide Corporation Blends of epoxides and monoepoxides

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