GB1011315A - Stabilisers for acrylic or methacrylic esters - Google Patents

Stabilisers for acrylic or methacrylic esters

Info

Publication number
GB1011315A
GB1011315A GB44620/63A GB4462063A GB1011315A GB 1011315 A GB1011315 A GB 1011315A GB 44620/63 A GB44620/63 A GB 44620/63A GB 4462063 A GB4462063 A GB 4462063A GB 1011315 A GB1011315 A GB 1011315A
Authority
GB
United Kingdom
Prior art keywords
butyl
tert
methoxyphenol
ditert
sec
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
GB44620/63A
Inventor
Richard Loversidge
Leonard Louis Pearson
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries 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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB44620/63A priority Critical patent/GB1011315A/en
Priority to DE1468118A priority patent/DE1468118C3/en
Priority to US408745A priority patent/US3356663A/en
Priority to DK552864AA priority patent/DK130068B/en
Priority to ES0305906A priority patent/ES305906A1/en
Priority to NL6413111A priority patent/NL134846C/xx
Priority to SE13584/64A priority patent/SE338983B/xx
Priority to CH1453364A priority patent/CH439752A/en
Priority to FR994717A priority patent/FR1418373A/en
Publication of GB1011315A publication Critical patent/GB1011315A/en
Priority to BE786375A priority patent/BE786375Q/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
    • C08F2/00—Processes of polymerisation
    • C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
    • 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
    • C07C67/62—Use of additives, e.g. for stabilisation
    • 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
    • C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
    • C08F2/40—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation using retarding agents
    • 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
    • C08F20/12—Esters of monohydric alcohols or phenols
    • 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
    • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
    • C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polymerisation Methods In General (AREA)

Abstract

Stabilizers for acrylic and methacrylic esters comprising 4-alkoxy phenol with less than 4 carbon atoms in the 4-alkoxy group and substituted in one or both the 2 and 6 positions by a sec. or tert. alkyl group containing at least 4 carbon atoms (see Division C2), are present during polymerization of the esters. Examples describe the polymerization of methyl methacrylate syrups containing 2,6-di-tert.-butyl-4-methoxy - phenol, and 2,21 - dihydroxy - 3,31-di - tert. - butyl - 5,51 - dimethoxy - diphenylmethane using benzoyl peroxide and a ,a -azo-di-isobutyro-nitrile as catalysts. Other stabilizers mentioned are 2-tert.-butyl-4-methoxyphenol and 2-sec.-butyl-4-methoxyphenol.ALSO:Stabilizers for acrylic and methacrylic esters comprise a 4-alkoxyphenol containing fewer than 4 carbon atoms in the alkoxy groups, and substituted on one or both of the 2 and 6 positions with a secondary or tertiary alkyl group containing at least 4 carbon atoms. 4-Methoxy phenols are preferred, e.g. 2-tert-butyl - 2,6 - ditert - butyl-, and 2 - sec - butyl - 4-methoxyphenols; and others have a tert-alkyl in the 2-position and 2-hydroxy-3-tert alkyl-5-alkoxyphenyl methyl in the 6-position, e.g. 2,21 - dihydroxy - 3,31 - ditert - butyl - 5,51-dimethoxy - diphenylmethane. Examples describe the stabilization of methyl methacrylate by 2,6 - ditert - butyl - 4 - methoxyphenol; 2,21-dihydroxy - 3,31 - ditert - butyl - 5,5 - dimethoxy - diphenyl methane; 2 - sec - butyl - 4 - methoxyphenol; 2 - tert - butyl - 4 - methoxy phenol; n-butyl methacrylate with 2,6-di-tert-butyl - 4 - methoxyphenol; ethyl acrylate with 2,6 - ditert - butyl - 4 - methoxyphenol, and n-butyl acrylate with 2,6-ditert-butyl-4-methoxyphenol. The esters may be polymerized in the presence of the stabilizer.
GB44620/63A 1963-11-12 1963-11-12 Stabilisers for acrylic or methacrylic esters Expired GB1011315A (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
GB44620/63A GB1011315A (en) 1963-11-12 1963-11-12 Stabilisers for acrylic or methacrylic esters
DE1468118A DE1468118C3 (en) 1963-11-12 1964-11-03 Alkyl acrylate or methacrylate stabilized against polymerization
US408745A US3356663A (en) 1963-11-12 1964-11-04 Stabilized monomers with alkoxyphenols
DK552864AA DK130068B (en) 1963-11-12 1964-11-09 Stabilized monomer material containing an alkyl acrylate or an alkyl methacrylate.
NL6413111A NL134846C (en) 1963-11-12 1964-11-11
ES0305906A ES305906A1 (en) 1963-11-12 1964-11-11 Procedure for the stabilization of acrylic monomers. (Machine-translation by Google Translate, not legally binding)
SE13584/64A SE338983B (en) 1963-11-12 1964-11-11
CH1453364A CH439752A (en) 1963-11-12 1964-11-11 Durable mixture containing acrylic or methacrylic esters
FR994717A FR1418373A (en) 1963-11-12 1964-11-12 Stabilized monomers
BE786375A BE786375Q (en) 1963-11-12 1972-07-17 STABILIZED MONOMERS

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB44620/63A GB1011315A (en) 1963-11-12 1963-11-12 Stabilisers for acrylic or methacrylic esters
GB1778664 1964-04-29

Publications (1)

Publication Number Publication Date
GB1011315A true GB1011315A (en) 1965-11-24

Family

ID=26252924

Family Applications (1)

Application Number Title Priority Date Filing Date
GB44620/63A Expired GB1011315A (en) 1963-11-12 1963-11-12 Stabilisers for acrylic or methacrylic esters

Country Status (9)

Country Link
US (1) US3356663A (en)
BE (1) BE786375Q (en)
CH (1) CH439752A (en)
DE (1) DE1468118C3 (en)
DK (1) DK130068B (en)
ES (1) ES305906A1 (en)
GB (1) GB1011315A (en)
NL (1) NL134846C (en)
SE (1) SE338983B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021244894A1 (en) * 2020-06-05 2021-12-09 Basf Se Polymerization inhibitors

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4216257A (en) * 1979-04-20 1980-08-05 Minnesota Mining And Manufacturing Company Strip material for forming flexible backed fasteners
US4542231A (en) * 1983-07-05 1985-09-17 Celanese Corporation Stabilized ethylenically unsaturated organic compositions
US4590301A (en) * 1984-10-24 1986-05-20 Barnes-Hind, Inc. Polymerization inhibitors
JPH0694437B2 (en) * 1989-03-16 1994-11-24 チッソ株式会社 Method for producing and storing alkylene glycol monosorbate
US6271281B1 (en) 1999-08-26 2001-08-07 Medennium, Inc. Homopolymers containing stable elasticity inducing crosslinkers and ocular implants made therefrom
WO2022230915A1 (en) * 2021-04-28 2022-11-03 三菱ケミカル株式会社 Methyl methacrylate-containing composition and methyl methacrylate polymer production method

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021244894A1 (en) * 2020-06-05 2021-12-09 Basf Se Polymerization inhibitors

Also Published As

Publication number Publication date
CH439752A (en) 1967-07-15
DE1468118B2 (en) 1976-07-22
BE786375Q (en) 1972-11-16
SE338983B (en) 1971-09-27
NL6413111A (en) 1965-05-13
DK130068C (en) 1975-05-26
NL134846C (en) 1972-03-15
DE1468118C3 (en) 1978-09-07
US3356663A (en) 1967-12-05
DK130068B (en) 1974-12-16
ES305906A1 (en) 1965-04-16
DE1468118A1 (en) 1969-03-13

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