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GB1109920A - Esters of itaconic acid and polymeric derivatives thereof - Google Patents

Esters of itaconic acid and polymeric derivatives thereof

Info

Publication number
GB1109920A
GB1109920A GB5012765A GB5012765A GB1109920A GB 1109920 A GB1109920 A GB 1109920A GB 5012765 A GB5012765 A GB 5012765A GB 5012765 A GB5012765 A GB 5012765A GB 1109920 A GB1109920 A GB 1109920A
Authority
GB
United Kingdom
Prior art keywords
itaconic acid
esters
itaconate
ethylene group
alkyl
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
GB5012765A
Inventor
Michael Edgar Hall
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.)
Pfizer Ltd
Original Assignee
Pfizer 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 Pfizer Ltd filed Critical Pfizer Ltd
Priority to GB5012765A priority Critical patent/GB1109920A/en
Priority to GB1371666A priority patent/GB1140087A/en
Priority to DE19661593278 priority patent/DE1593278A1/en
Priority to FR85048A priority patent/FR1502314A/en
Publication of GB1109920A publication Critical patent/GB1109920A/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
    • C08F22/00—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 a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
    • C08F22/10—Esters
    • C08F22/12—Esters of phenols or saturated alcohols
    • C08F22/20—Esters containing oxygen in addition to the carboxy oxygen
    • 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
    • C08F22/00—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 a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof

Landscapes

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

Abstract

Polymers or copolymers of novel esters of itaconic acid of formula <FORM:1109920/C3/1> where R is an ethylene group or an alkyl or aryl substituted ethylene group and n is 1 or 2 specifically (2 - hydroxyethyl) (2 - [hydroxyethoxy]ethyl) itaconate and (2-hydroxypropyl)-(2 - [2 - hydroxypropoxy] propyl) itaconate (see Division C2) are prepared by conventional methods. Ethylene, propylene, isobutylene, styrene, butadiene, methyl and ethyl acrylates and methacrylates, acrylic acid, itaconic acid, acrylonitrile, and vinyl esters of carboxylic acids may be the comonomers, and the presence of the hydroxyl groups allows cross-linking with resins such as urea- and melamine-formaldehyde resins or condensation with di- or polycarboxylic acids to give unsaturated polyester resins or with di- or poly-isocyanates to give unsaturated polyurethane polymers. Examples describe the copolymerization of the esters with styrene and butadiene, and methyl methacrylate with emulsion technique using an aq. mixture of the monomers, potassium persulphate, sodium bisulphite and sodium hydroxide and emulsifiers to give stable emulsions suitable as paint vehicles or as paper coating agents.ALSO:Esters of itaconic acid of formula <FORM:1109920/C2/1> where R is an ethylene group or an alkyl- or aryl-substituted ethylene group and n is 1 or 2, specifically (2-hydroxyethyl)(2-[2-hydroxyethoxy]ethyl)itaconate and (2-hydroxypropyl)(2-[2-hydroxypropoxy]propyl)itaconate are prepared by reacting an excess of three molar proportions of ethylene or an alkyl- or aryl-substituted ethylene oxide with itaconic acid in the presence of a lithium catalyst. Lithium chloride, bromide, iodide, sulphate, acetate, benzoate, hydroxide or hydride may be used and an inhibitor such as p-methoxyphenol added. The compounds may be homo- or copolymerized (see Division C3).
GB5012765A 1965-11-25 1965-11-25 Esters of itaconic acid and polymeric derivatives thereof Expired GB1109920A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
GB5012765A GB1109920A (en) 1965-11-25 1965-11-25 Esters of itaconic acid and polymeric derivatives thereof
GB1371666A GB1140087A (en) 1965-11-25 1966-03-29 Esters of itaconic acid
DE19661593278 DE1593278A1 (en) 1965-11-25 1966-11-24 Process for the preparation of itaconic acid esters
FR85048A FR1502314A (en) 1965-11-25 1966-11-25 Novel esters of itaconic acid, polymers of these esters, and processes for their preparation

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB5012765A GB1109920A (en) 1965-11-25 1965-11-25 Esters of itaconic acid and polymeric derivatives thereof
GB1371666A GB1140087A (en) 1965-11-25 1966-03-29 Esters of itaconic acid
GB4822266 1966-10-27

Publications (1)

Publication Number Publication Date
GB1109920A true GB1109920A (en) 1968-04-18

Family

ID=27257024

Family Applications (2)

Application Number Title Priority Date Filing Date
GB5012765A Expired GB1109920A (en) 1965-11-25 1965-11-25 Esters of itaconic acid and polymeric derivatives thereof
GB1371666A Expired GB1140087A (en) 1965-11-25 1966-03-29 Esters of itaconic acid

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB1371666A Expired GB1140087A (en) 1965-11-25 1966-03-29 Esters of itaconic acid

Country Status (3)

Country Link
DE (1) DE1593278A1 (en)
FR (1) FR1502314A (en)
GB (2) GB1109920A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2851614A1 (en) * 1978-11-29 1980-06-04 Synthopol Chemie Dr Koch METHOD FOR PRODUCING HYDROXYL GROUP-COPOLYMERISATS SOLUBLE IN ORGANIC SOLVENTS USING AN ESTERIALIZATION CATALYST

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2907997C2 (en) * 1979-03-01 1982-04-15 Hoechst Ag, 6000 Frankfurt Process for the preparation of curable copolymers
JPH02212455A (en) * 1989-02-14 1990-08-23 Ube Ind Ltd Itaconic acid monoester compound and adhesive containing same compound

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2851614A1 (en) * 1978-11-29 1980-06-04 Synthopol Chemie Dr Koch METHOD FOR PRODUCING HYDROXYL GROUP-COPOLYMERISATS SOLUBLE IN ORGANIC SOLVENTS USING AN ESTERIALIZATION CATALYST

Also Published As

Publication number Publication date
FR1502314A (en) 1967-11-18
GB1140087A (en) 1969-01-15
DE1593278A1 (en) 1970-04-30

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