GB612311A - Improvements in or relating to the production of polymerisable esters - Google Patents

Improvements in or relating to the production of polymerisable esters

Info

Publication number
GB612311A
GB612311A GB9580/45A GB958045A GB612311A GB 612311 A GB612311 A GB 612311A GB 9580/45 A GB9580/45 A GB 9580/45A GB 958045 A GB958045 A GB 958045A GB 612311 A GB612311 A GB 612311A
Authority
GB
United Kingdom
Prior art keywords
substituted succinic
allyl alcohol
succinic acid
anhydride
esters
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
GB9580/45A
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.)
Lewis Berger and Sons Ltd
Original Assignee
Lewis Berger and Sons 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 Lewis Berger and Sons Ltd filed Critical Lewis Berger and Sons Ltd
Priority to GB9580/45A priority Critical patent/GB612311A/en
Publication of GB612311A publication Critical patent/GB612311A/en
Expired legal-status Critical Current

Links

Classifications

    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
    • H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
    • H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
    • H01B3/44—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes vinyl resins; acrylic resins
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F18/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
    • C08F18/02—Esters of monocarboxylic acids
    • C08F18/12—Esters of monocarboxylic acids with unsaturated alcohols containing three or more carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Organic Insulating Materials (AREA)
  • Macromonomer-Based Addition Polymer (AREA)

Abstract

Allyl or 2-methyl allyl alcohol esters of a mono-substituted succinic acid or anhydride in which the substituent is an organic radicle containing not less than three carbon atoms are polymerized to oils or soft resins. The substituted succinic acid or anhydride may be produced by the addition reaction of maleic anhydride with a non-conjugated poly-unsaturated organic compound such as a non-conjugated terpene or a drying oil fatty acid or an ester thereof, or with an aromatic hydrocarbon having a saturated aliphatic or carbocyclic side chain, e.g. with toluene which yields benzyl succinic acid. The substituent may also be unsaturated, e.g. an alkenyl radicle. Polymerization catalysts, e.g. benzoyl peroxide may be present. The products may be used in bonding, electrical insulating, impregnating and surface coating compositions. Fabricated products such as brake linings or plywood may be produced by using the polymerized esters as bonding agents. In examples (2) and (4) the addition products obtained by heating maleic anhydride with dipentene and raw linseed oil respectively are esterified with allyl alcohol in the presence of a small amount of p-toluene sulphonic acid and polymerised in the presence of benzoyl peroxide at 130 DEG -140 DEG C.; (3) a mixture of monoalkenyl substituted succinic anhydrides containing alkenyl groups with from 8 to 10 carbon atoms is refluxed with allyl alcohol in the presence of a small amount of p-toluene sulphonic acid and polymerised at 140 DEG C. in the presence of benzoyl peroxide. Specifications 500,348, 552,095, 612,312 and German Specification 607,380 are referred to. The Provisional Specification refers also to Specification 552,228.ALSO:Polymerizable esters are prepared by esterifying with allyl or 2-methyl allyl alcohol, a mono-substituted succinic acid or anhydride in which the substituent is an organic radicle containing not less than three carbon atoms or by effecting an alcoholysis reaction between a lower alkyl ester of said substituted succinic acid and allyl or methallyl alcohol. The substituted succinic acid or anhydride may be produced by the addition reaction of maleic anhydride with a non-conjugated poly-unsaturated organic compound such as a non-conjugated terpene or a drying oil fatty acid or an ester thereof, or with an aromatic hydrocarbon having a saturated aliphatic or carbocyclic side chain, e.g. with toluene which yields benzyl succinic acid. The substituent may also be unsaturated, e.g. an alkenyl radicle. The products vary from oils to soft resins of the character of balsams and can be used in bonding compositions, electrical insulating compositions and in varnish impregnating and surface coating compositions. Fabricated products such as brake linings or plywood may be produced by using the polymerized esters as bonding agents. In examples: (1) allyl alcohol is added to the adduct obtained by heating dimethyl maleate and the methyl esters of linseed oil fatty acids, the diallyl ester of the maleate adduct being produced by alcoholysis, (2) and (4) the addition products obtained by heating maleic anhydride with dipentene and raw linseed oil respectively are esterified with allyl alcohol in the presence of a small amount of p-toluene sulphonic acid; (3) a mixture of mono-alkenyl substituted succinic anhydrides containing alkenyl groups with from 8 to 10 carbon atoms is refluxed with allyl alcohol in the presence of a small amount of p-toluene sulphonic acid. The purified ester is a light yellow oil. Specifications 500,348, 552,095, 612,312 and German Specification 607,380 are referred to. The Provisional Specification refers also to Specification 552,228.
GB9580/45A 1945-04-17 1945-04-17 Improvements in or relating to the production of polymerisable esters Expired GB612311A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB9580/45A GB612311A (en) 1945-04-17 1945-04-17 Improvements in or relating to the production of polymerisable esters

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB9580/45A GB612311A (en) 1945-04-17 1945-04-17 Improvements in or relating to the production of polymerisable esters

Publications (1)

Publication Number Publication Date
GB612311A true GB612311A (en) 1948-11-11

Family

ID=9874741

Family Applications (1)

Application Number Title Priority Date Filing Date
GB9580/45A Expired GB612311A (en) 1945-04-17 1945-04-17 Improvements in or relating to the production of polymerisable esters

Country Status (1)

Country Link
GB (1) GB612311A (en)

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