GB826831A - Pentachlorophenyl acrylate and its polymers and co-polymers - Google Patents

Pentachlorophenyl acrylate and its polymers and co-polymers

Info

Publication number
GB826831A
GB826831A GB21602/58A GB2160258A GB826831A GB 826831 A GB826831 A GB 826831A GB 21602/58 A GB21602/58 A GB 21602/58A GB 2160258 A GB2160258 A GB 2160258A GB 826831 A GB826831 A GB 826831A
Authority
GB
United Kingdom
Prior art keywords
ester
solution
copolymerized
propanol
sodium
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
GB21602/58A
Inventor
Gerhard Faerber
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.)
Cavity GmbH
Original Assignee
Deutsche Solvay Werke 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 Deutsche Solvay Werke GmbH filed Critical Deutsche Solvay Werke GmbH
Priority to GB21602/58A priority Critical patent/GB826831A/en
Publication of GB826831A publication Critical patent/GB826831A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/22—Esters containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/62—Halogen-containing esters
    • C07C69/65—Halogen-containing esters of unsaturated acids
    • C07C69/653—Acrylic acid esters; Methacrylic acid esters; Haloacrylic acid esters; Halomethacrylic acid esters

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

The invention comprises pentachlorophenyl acrylate which may be prepared by adding acrylic acid chloride to a solution of sodium pentachlorophenolate in excess of an anhydrous alcohol and separating the ester from the reaction mixture. The reaction preferably takes place in methanol, ethanol, or propanol at 0-60 DEG C. In examples (10-12) pentachlorophenol is dissolved in a solution of sodium in anhydrous methanol and acrylyl chloride added at temperatures up to 65 DEG C., the yield decreases with increased reaction temperatures; (13) pentachlorophenol is heated with sodium hydroxide solution, the water azeotropically removed with xylene, the residue dissolved in anhydrous methanol and acrylyl chloride added at 50 DEG C.; (14) sodium pentachlorophenolate is dissolved is n-propanol, the solution dehydrated by azeotropically distilling off any water with the n-propanol and acrylyl chloride added at 55-60 DEG C. The ester may be polymerized or copolymerized with other olefinic monomers.ALSO:The invention comprises a homopolymer of pentachlorophenyl acrylate or a copolymer of the ester with a polymerizable olefinically unsaturated monomer. The homopolymer, which may be prepared by heating in the presence or absence of the usual catalysts, contains 55.3% aromatically bound chlorine. The ester may be copolymerized with styrenes, acrylonitrile, allyl compounds or vinyl or acrylic esters by heating in the presence of a catalyst such as benzoyl peroxide or cyclohexanone peroxide. The copolymers may be subsequently heated to give improved heat stabilities. In examples, pentachlorophenyl acrylate is homopolymerized and copolymerized with styrene, acrylonitrile and methyl methacrylate.
GB21602/58A 1958-07-05 1958-07-05 Pentachlorophenyl acrylate and its polymers and co-polymers Expired GB826831A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB21602/58A GB826831A (en) 1958-07-05 1958-07-05 Pentachlorophenyl acrylate and its polymers and co-polymers

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB21602/58A GB826831A (en) 1958-07-05 1958-07-05 Pentachlorophenyl acrylate and its polymers and co-polymers

Publications (1)

Publication Number Publication Date
GB826831A true GB826831A (en) 1960-01-20

Family

ID=10165677

Family Applications (1)

Application Number Title Priority Date Filing Date
GB21602/58A Expired GB826831A (en) 1958-07-05 1958-07-05 Pentachlorophenyl acrylate and its polymers and co-polymers

Country Status (1)

Country Link
GB (1) GB826831A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3932321A (en) 1973-06-18 1976-01-13 Japan Synthetic Rubber Company Limited Flame-retardant polymer composition
EP0267460A1 (en) * 1986-10-25 1988-05-18 Hoechst Aktiengesellschaft Transparent polymers
US4939219A (en) * 1988-02-01 1990-07-03 Kansai Paint Company, Limited Coating compositions for preventing adhesion of aquatic organisms

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3932321A (en) 1973-06-18 1976-01-13 Japan Synthetic Rubber Company Limited Flame-retardant polymer composition
EP0267460A1 (en) * 1986-10-25 1988-05-18 Hoechst Aktiengesellschaft Transparent polymers
US4939219A (en) * 1988-02-01 1990-07-03 Kansai Paint Company, Limited Coating compositions for preventing adhesion of aquatic organisms

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