GB984827A - - Google Patents

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Publication number
GB984827A
GB984827A GB984827DA GB984827A GB 984827 A GB984827 A GB 984827A GB 984827D A GB984827D A GB 984827DA GB 984827 A GB984827 A GB 984827A
Authority
GB
United Kingdom
Prior art keywords
unsaturated
acrylate
epoxidized
epoxy
dimethylene
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.)
Active
Application number
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.)
Publication of GB984827A publication Critical patent/GB984827A/en
Active legal-status Critical Current

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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
    • C07D303/14—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
    • C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Epoxy Compounds (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

984,827. Unsaturated epoxy esters. CONSORTIUM FUR ELEKTROCHEMISCHE INDUSTRIE G.m.b.H. July 17, 1961 [July 16, 1960], No. 25890/61. Heading C2C. Unsaturated epoxy esters of the formula RO.COR<SP>1</SP> where R is a saturated epoxidized mono- or poly-carbocyclic ring system containing at least 6 carbon atoms, and R<SP>1</SP> is a branched or unbranched alkenyl group with at the most 4 carbon atoms, are made by selective epoxidation in a known manner of an unsaturated ester of a cyclo-olefinic alcohol. Epoxidation may be effected with a peracid, e.g., peracetic acid, in the presence of an inert diluent, or with hydrogen peroxide in the presence of a carboxylic acid and a catalyst. The quantity of percompound is usually 1.05-1.2 mol. per mol. of the double bond to be epoxidized and the reaction is effected at 0-40‹ C. The starting materials may be made by esterifying unsaturated carbocyclic alcohols, e.g. cyclohexenols, dehydronorborneol, 1,4 - 5,8 - dimethylene- #<SP>6,7</SP> - octahydro - # - naphthol, tricyclo. [5,2,1,0<SP>2</SP>,<SP>6</SP>] - decene - #<SP>3,4</SP> - ol - 9, with unsaturated carboxylic acids such as acrylic, methacrylic or crotonic acid. The unsaturated esters may also be made by transesterification of unsaturated esters such as methyl acrylate, methyl methacrylate, ethyl acrylate or an ester of crotonic acid with the cyclo-olefinic alcohols in the presence of transesterification catalysts. The unsaturated acids mentioned above may also be added to carbocyclic dienes such as dicyclopentadiene, bicyclo - [2,2,1] - heptadiene, cyclohexadiene, 1,4 - 5,8 - dimethylene- #<SP>2,2-6,7</SP>-hexahydronaphthalene, in the presence of Lewis acids. In examples, (1) butyl acrylate is transesterified with tricyclo - [5,2,1,0<SP>2</SP>,<SP>6</SP>] - decene - #<SP>3</SP>,<SP>4</SP> - of - 9 in the presence of H 2 SO 4 and the acrylic ester formed is epoxidized to the acrylate of 3,4 - epoxy - tricyclo - [5,2,1,0<SP>2</SP>,<SP>6</SP>]- decanol-9; (2) methyl acrylate is transesterified with dehydronorborneol and the ester formed is epoxidized to the acrylate of 5: 6-epoxy-2-hydroxy - bicyclo - [2: 2: 1] - heptane; (3) methyl acrylate is transesterified with 1: 4: 5: 8- dimethylene - #<SP>6</SP>,<SP>7</SP> - octahydro - # - naphthol and the ester epoxidized to the acrylate of 1,4,5,8 - dimethylene - 6,7 - epoxy - decahydro- #-naphthol. Specification 935,756 is referred to.
GB984827D 1960-07-16 Active GB984827A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEC0021929 1960-07-16

Publications (1)

Publication Number Publication Date
GB984827A true GB984827A (en)

Family

ID=7017102

Family Applications (1)

Application Number Title Priority Date Filing Date
GB984827D Active GB984827A (en) 1960-07-16

Country Status (3)

Country Link
CH (1) CH410911A (en)
DE (1) DE1418698A1 (en)
GB (1) GB984827A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3807571A1 (en) * 1987-03-09 1988-09-22 Kansai Paint Co Ltd RESINABLE RESIN DIMENSIONS AT LOW TEMPERATURES
WO2001009078A1 (en) * 1999-07-28 2001-02-08 Dexter Corporation Low viscosity acrylate monomers, formulations containing same, and uses therefor
JP2006151900A (en) * 2004-11-30 2006-06-15 Daicel Chem Ind Ltd Cycloaliphatic epoxy (meth)acrylate and its preparation method

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1250726A (en) * 1984-02-25 1989-03-07 Fredrick G. Wilson Profiled sheet material
US6124483A (en) * 1996-12-23 2000-09-26 Sartomer Technology Company Process for preparing unsaturated esters containing cyclic epoxy group

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3807571A1 (en) * 1987-03-09 1988-09-22 Kansai Paint Co Ltd RESINABLE RESIN DIMENSIONS AT LOW TEMPERATURES
DE3807571C3 (en) * 1987-03-09 1998-06-10 Kansai Paint Co Ltd Silicone resin composition curable at low temperatures
WO2001009078A1 (en) * 1999-07-28 2001-02-08 Dexter Corporation Low viscosity acrylate monomers, formulations containing same, and uses therefor
US6211320B1 (en) 1999-07-28 2001-04-03 Dexter Corporation Low viscosity acrylate monomers formulations containing same and uses therefor
JP2006151900A (en) * 2004-11-30 2006-06-15 Daicel Chem Ind Ltd Cycloaliphatic epoxy (meth)acrylate and its preparation method

Also Published As

Publication number Publication date
CH410911A (en) 1966-04-15
DE1418698A1 (en) 1968-10-10

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