GB570216A - Improvement in and relating to esters of chloromaleic acid - Google Patents

Improvement in and relating to esters of chloromaleic acid

Info

Publication number
GB570216A
GB570216A GB5647/43A GB564743A GB570216A GB 570216 A GB570216 A GB 570216A GB 5647/43 A GB5647/43 A GB 5647/43A GB 564743 A GB564743 A GB 564743A GB 570216 A GB570216 A GB 570216A
Authority
GB
United Kingdom
Prior art keywords
acid
esters
butadiene
ester
copolymerized
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
GB5647/43A
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.)
Wingfoot Corp
Original Assignee
Wingfoot Corp
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 Wingfoot Corp filed Critical Wingfoot Corp
Publication of GB570216A publication Critical patent/GB570216A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F22/00Homopolymers 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 a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
    • C08F22/10Esters
    • C08F22/12Esters of phenols or saturated alcohols
    • C08F22/18Esters containing halogen
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F36/00Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C08F36/02Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
    • C08F36/04Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Aralkyl esters of monochlormaleic acid are prepared by esterification of chlormaleic acid by treating the acid or its anhydride with an aralkyl alcohol, for example, benzyl or b -phenethyl alcohol, preferably under reflux and with an acid catalyst. Other esters specified are the g -phenylpropyl, cinnamyl, a -naphthylmethyl, p-tolylethyl, and biphenylethyl diesters. Di-esters containing only one aralkyl radical are included. The esters are copolymerized with butadienes, such as butadiene-1,3 or its 2-chlor- or 2-cyano-derivative, pentadienes, such as isoprene, hexadienes, such as 2-methylpentadiene-1,3 or 2,3-dimethylbutadiene-1,3, styrenes, such as styrene or 2-chlorstyrene, vinyl chloride or bromide, acrylates or alkacrylates, such as methyl acrylate or methacrylate. Ratios of butadiene to ester of from 20 : 80 to 90 : 10 may be used. The emulsion copolymers can be milled with plasticizers and used as moulding and coating compositions. In examples: (1) chlormaleic acid and benzyl alcohol are refluxed with benzene and sulphuric acid using a water trap on the condenser to produce dibenzyl chlormaleate; (2) chlormaleic anhydride and b -phenethyl alcohol similarly give the di-b -phenethyl ester; (3) butadiene-1,3 and the dibenzyl ester in the ratio of 60 : 40 by weight are copolymerized by shaking at 38 DEG C. in the presence of a solution containing buffer, wetting agents, carbon tetrachloride, potassium cyanide, acetaldehyde, and sodium perborate to yield a rubber; (4) the di-b -phenethyl ester is copolymerized similarly with butadiene.
GB5647/43A 1942-08-25 1943-04-08 Improvement in and relating to esters of chloromaleic acid Expired GB570216A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US570216XA 1942-08-25 1942-08-25

Publications (1)

Publication Number Publication Date
GB570216A true GB570216A (en) 1945-06-27

Family

ID=22008010

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5647/43A Expired GB570216A (en) 1942-08-25 1943-04-08 Improvement in and relating to esters of chloromaleic acid

Country Status (1)

Country Link
GB (1) GB570216A (en)

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