GB958979A - New epoxy-ethers and their manufacture and use - Google Patents

New epoxy-ethers and their manufacture and use

Info

Publication number
GB958979A
GB958979A GB2171861A GB2171861A GB958979A GB 958979 A GB958979 A GB 958979A GB 2171861 A GB2171861 A GB 2171861A GB 2171861 A GB2171861 A GB 2171861A GB 958979 A GB958979 A GB 958979A
Authority
GB
United Kingdom
Prior art keywords
epoxy
aliphatic
alcohol
olefinic
dimetheno
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
GB2171861A
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.)
Consortium fuer Elektrochemische Industrie GmbH
Original Assignee
Consortium fuer Elektrochemische Industrie GmbH
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 Consortium fuer Elektrochemische Industrie GmbH filed Critical Consortium fuer Elektrochemische Industrie GmbH
Publication of GB958979A publication Critical patent/GB958979A/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
    • 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
    • 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
    • C07D303/28—Ethers with hydroxy compounds containing oxirane rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/15—Heterocyclic compounds having oxygen in the ring
    • C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
    • C08K5/1515—Three-membered rings

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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises saturated asym -metrical epoxy-ethers ROR1 in which R represents a 5:6-epoxybicyclo-[2,2,1]-heptyl, a 3:4-epoxytricyclo-[5,2,1,02:6]-decyl or 6:7-epoxy-1:4:5:8-dimetheno-decahydronaphthyl group and R1 represents an epoxidated unbranched or branched alkyl radical, particularly epoxypropyl, epoxybutyl or epoxyethyl hexyl. The novel compounds may be made by epoxidation of an aliphatic unbranched or branched alkenyl ether of dehydro-norborneol, tricyclo [5,2,1,02:6]-decen-D 3:4-ol-9, or 2-hydroxy-1:4:5:8-dimetheno-D 6:7 -octahydronaphthalene. The epoxidation may be effected with per-acids, e.g. peracetic, in an inert solvent, or with hydrogen peroxide in the presence of a carboxylic acid and an acid catalyst, with hydrogen peroxide in the presence of bases and catalysts such as sodium tungstate, and also with organic percompounds such as t-butyl hydroperoxide. Temperatures of 0 DEG to 40 DEG C. are suitable. The unsaturated ether starting materials may be made by etherifying the appropriate polyolic olefinic alcohol with an aliphatic unsaturated alcohol, e.g., allyl alcohol, crotyl alcohol, or 2-ethylhexanol. The ethers are also made by reacting alcoholates of the polycyclic olefinic alcohols with appropriate aliphatic olefinic chlorides, such as allyl chloride, crotyl chloride or 3-chlorobutene-1, or by reacting the alcohols with the chlorides in the presence of strong bases. Another method comprises reacting the aliphatic olefinic alcohols with dicyclopentadiene, bicycloheptadiene or 1:4; 5:8-dimetheno-D 2:3; 6:7-hexahydronaphthalene in the presence of a Lewis acid. Detailed examples are given.ALSO:Epoxy compounds of the formula ROR1 wherein R represents a 5:6-epoxybicyclo-[2, 2, 1]-heptyl, a 3,4-epoxy-tricyclo-[5, 2, 1, 02:6], decyl or 6, 7-epoxy-1, 4, 5, 8-dimethano-decahydronaphthyl group and R1 represents an epoxidated unbranched or branched alkyl radical, are hardened with known hardening agents for epoxy resins, for example anhydrides of polybasic carboxylic acids. In examples, the 2:3-epoxybutyl ether of 3:4-epoxytricyclo [5, 2, 1, 02:6] decanol-9 is hardened with pyromellitic anhydride, or maleic anhydride with the addition of ethylene glycol, pentaerythritol or trimethylol propane.
GB2171861A 1960-06-15 1961-06-15 New epoxy-ethers and their manufacture and use Expired GB958979A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEC0021694 1960-06-15

Publications (1)

Publication Number Publication Date
GB958979A true GB958979A (en) 1964-05-27

Family

ID=7017053

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2171861A Expired GB958979A (en) 1960-06-15 1961-06-15 New epoxy-ethers and their manufacture and use

Country Status (4)

Country Link
CH (1) CH411848A (en)
DE (1) DE1418696A1 (en)
GB (1) GB958979A (en)
NL (1) NL265790A (en)

Also Published As

Publication number Publication date
CH411848A (en) 1966-04-30
DE1418696A1 (en) 1968-10-10
NL265790A (en)

Similar Documents

Publication Publication Date Title
US2485160A (en) Process for the epoxidation of esters of oleic and linoleic acids
GB1119476A (en) Molybdenum catalyst and manufacture thereof
GB880937A (en) New epoxy carbonate esters
US3042686A (en) Epoxydicyclopentyl alcohols and process for preparing same
US3927116A (en) Bicyclo{8 2.2.1{9 {0 Hept-5(6)-yl compounds
GB1123960A (en) Organosilicon epoxides
US2692271A (en) Method of epoxidation
GB958979A (en) New epoxy-ethers and their manufacture and use
GB904549A (en) Preparation of epoxy ethers and formation of cured resinous products therefrom
US2774774A (en) In situ epoxidation of oleic acid using formic acid
GB873868A (en) Epoxy esters derived from cyclopentadienes
GB938353A (en) Improvements in and relating to epoxy polycyclic compounds
GB932960A (en) New acetals containing epoxide groups
US3459775A (en) Bicyclo(2.2.1)hept-5(6)-yl compounds
US3558665A (en) Epoxidized peroxides
GB1002185A (en) Improvements in and relating to epoxy resins
GB944408A (en) New epoxides, process for their preparation, and compositions containing them
GB943925A (en) Mixtures of compounds containing epoxide groups, their production and their uses
ES275223A1 (en) Curable mistures of diepoxy compounds and dicarboxylic acid anhydrides
US2883396A (en) Hemiacetal ester epoxides
GB956698A (en) New polyepoxides, their preparation and their use
GB922206A (en) Process for the preparation of oxirane derivatives
GB784187A (en) Steroids
GB919190A (en) New glycidyl ethers containing at least two epoxide groups and process for their preparation
US2998432A (en) Ethylene oxide adducts of epoxycontaining fatty acids