GB401653A - Improvements in or relating to the manufacture of plastic masses from methacrylic acid esters - Google Patents

Improvements in or relating to the manufacture of plastic masses from methacrylic acid esters

Info

Publication number
GB401653A
GB401653A GB1240232A GB1240232A GB401653A GB 401653 A GB401653 A GB 401653A GB 1240232 A GB1240232 A GB 1240232A GB 1240232 A GB1240232 A GB 1240232A GB 401653 A GB401653 A GB 401653A
Authority
GB
United Kingdom
Prior art keywords
methacrylic acid
ester
ethyl ester
acetate
esters
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
GB1240232A
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.)
Roehm and Haas GmbH
Original Assignee
Roehm and Haas 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 Roehm and Haas GmbH filed Critical Roehm and Haas GmbH
Priority to GB1240232A priority Critical patent/GB401653A/en
Publication of GB401653A publication Critical patent/GB401653A/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
    • C08F20/00Homopolymers 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
    • C08F20/02Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10Esters
    • C08F20/12Esters of monohydric alcohols or phenols
    • 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
    • C08F265/00Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C08F265/04Macromolecular 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
    • C08F265/06Polymerisation of acrylate or methacrylate esters on to polymers thereof

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Laminated Bodies (AREA)

Abstract

Plastic masses are prepared by incorporating wholly or partially polymerized methacrylic acid methyl ester or ethyl ester with one another or with one or more additional substance at any stage in the polymerization which may be effected if desired in solution or in aqueous emulsion and with the aid of catalysts. The term additional substance includes softeners such as phthalic, tartaric, phosphoric and stearic acid esters, acetin, drying and non-drying oils, camphor and naphthalene, hardeners such as paraformaldehyde, plastifiers, products of methacrylic acid or its derivatives differing from those which form the basic constituents of the mass such as methacrylic acid nitrile, polyvinyl alcohols, organic and inorganic vinyl esters such as vinyl acetate and chloride, vinyl ethers, vinyl ketones, olefines and diolefines such as styrene or butadiene, cellulose derivatives such as cellulose acetates, nitrocellulose, methyl, ethyl and benzyl cellulose, natural resins, such as copal, dammar, colophonium and shellac, artificial resins such as condensation product of formaldehyde and phenol or urea, p-toluene sulphonamide resins, and fillers such as zinc oxide, ferric oxide, kaolin, talc, lampblack, organic and inorganic colouring matters. Suitable catalysts for polymerization are oxygen or substances developing oxygen such as the peroxides of sodium, barium or hydrogen, benzoyl peroxide and uranyl acetate. Solvents include hydrocarbons of the benzine and benzene series, ethylene chloride, chloroform, trichlorethylene, chlorobenzene, alcohol, ether, dioxane, acetone, cyclohexanone, ethyl acetate and amyl acetate. The products may be used for the manufacture of films, lacquers, varnishes, glass substitutes and in the production of knife handles, umbrella handles, billiard balls, penholders, tiles, electric insulating materials, artificial silk, leather and guttapercha, bandaging materials, lacquers for leather and bases for pasty colours. In examples: (1) polymerized methacrylic acid and ethyl ester, which may be polymerized by heat, light or with benzoyl superoxide, is mixed with dibutyl tartrate and dissolved in ethyl acetate. By evaporation of the solvent from the solution on bands, films or plates are obtained suitable for use as boiler linings, protective coatings and gas-tight materials. (2) Powdered polymerized methacrylic acid ethyl esters is mixed with dibutyl phthalate and pressed to a transparent mass from which plates or sheets may be obtained by slicing. (3) Methacrylic acid and ethyl esters and blown linseed oil are polymerized in presence of a solvent such as ethy acetate by means of benzoyl peroxide to yield a leather substitute. (4) Polymethacrylic ethyl ester is blended with linoxyn with or without the addition of a phenol-formaldehyde condensation product and the diphthalic acid ester of ethylene glycol monoethylether. (6) Films suitable as photographic films or foli are prepared by evaporating a solution of polymethacrylic acid ethyl ester and nitrocellulose in acetic ester. (7) A product suitable for the manufacture of oilcloth is prepared by evaporating a solution of acetone of polymethacrylic acid ethyl ester, colophonium or other natural or synthetic resins, and softeners. (8) Methacrylic acid ethyl ester, linoxyn, kaolin, and the diphthalic acid ester of ethylene glycol monomethyl ether are heated together to yield a film which may be applied to fabrics to produce oilcloth or gas-tight materials. (9) A mixture of methacrylic acid ethyl ester and nitrile is polymerized by means of benzoylperoxide, mixed with lampblack and used, in the manufacture of gramophone records. (10) A mixture of methacrylic acid methyl ester, methyl cellulose, a phenolformaldehyde condensation product and ferric oxide is polymerized in the presence of a solvent for the product such as acetone. (11) A solution of methacrylic acid methyl ester and nitrile and vinyl acetate in acetic esters is polymerized by means of sodium peroxide and mixed, after removal of the solvent, with sulphur and kaolin. (12) A mixture of a solution of cellulose acetate in acetone and polymerized methacrylic acid methyl ester in benzene is used for the production of artificial silk. (13) Lacquers are prepared from polymethacrylic acid methyl esters, dibutyl phthalate and benzene or polymethacrylic acid ethyl esters, methyl glycol phthalate, ethyl acetate and titanium dioxide. Specifications 355,712, [Group IV], 358,534, and 371,812, [Group V], are referred to. Reference has been directed by the Comptroller to Specification 395,687, [Group IV].ALSO:Plastic masses are prepared by incorporating wholly or partially polymerised methacrylic acid methyl ester or ethyl ester with one another and/or with one or more additional substance at any stage in the polymerisation which may be effected if desired in solution or in aqueous emulsion and with the aid of catalysts. The term additional substance includes softeners such as phthalic, tartaric, phosphoric and stearic acid esters, acetin, drying and non-drying oils, camphor and naphthalene, hardeners such as paraformaldehyde, plastifiers, products of methacrylic acid or its derivatives differing from those which form the basic constituents of the mass such as methacrylic acid nitrile, polyvinyl alcohols, organic and inorganic vinyl esters such as vinyl acetate and chloride, vinyl ethers, vinyl ketones, olefines and diolefines such as styrene or butadiene, cellulose derivatives such as cellulose acetates, nitrocellulose, methyl, ethyl and benzyl cellulose, natural resins, such as copal, dammar, colophonium and shellac, artificial resins such as condensation product of formaldehyde and phenol or urea, p-toluene sulphonamide resins, and fillers such as zinc oxide, ferric oxide, kaolin, talc, lampblack, organic and inorganic colouring matters. Suitable catalysts for polymerisation are oxygen or substances developing oxygen such as the peroxides of sodium, barium or hydrogen, benzoyl peroxide and uranyl acetate. Solvents include hydrocarbons of the benzine and benzene series, ethylene chloride, chloroform, trichloroethylene, chlorobenzene, alcohol, ether, dioxane, acetone, cyclohexanone, ethyl acetate and amyl acetate. The products may be used for the manufacture of films, lacquers, varnishes, glass substitutes and in the production of knife handles, umbrella handles, billiard balls, penholders, tiles, electric insulating materials, artificial silk, leather and guttapercha, bandaging materials, lacquers for leather and bases for pasty colours. In examples (1) polymerised methacrylic acid ethyl ester, which may be polymerised by heat, light or with benzoyl superoxide, is mixed with dibutyl tartrate and dissolved in ethyl acetate. By evaporation of the solvent from the solution on bands films or plates are obtained suitable for use as boiler linings, protective coatings and gas tight materials. (2) Powdered polymerised methacrylic acid ethyl ester is mixed with dibutyl phthalate and pressed to a transparent mass from which plates or sheets may be obtained by slicing. (3) Methacrylic acid ethyl ester and blown linseed oil are polymerised in presence of a solvent such as ethyl acetate by means of benzoyl peroxide to yield a leather substitute. (4) Polymethacrylic acid ethyl ester is blended with linoxyne with or without the addition of a phenol-formaldehyde condensation product and the diphthalic acid ester of ethylene glycol monoethyl ether. (6) Films suitable as photographic films or foliae are prepared by evaporating a solution of polymethacrylic acid ethyl ester and nitro cellulose in acetic ester. (7) A product suitable for the manufacture of oil cloth is prepared by evaporating a solution in acetone of polymethacrylic acid ethyl ester, colophonium or other natural or synthetic resins, and softeners. (8) Methacrylic acid ethyl ester, linoxyne, kaolin and the diphthalic acid ester of ethylene glycol monomethyl ether are heated together to yield a film which may be applied to fabrics to produce oil cloth or gas tight materials. (9) A mixture of methacrylic acid ethyl ester and nitrile is polymerised by means of benzoyl peroxide, mixed with lampblack and used, if desired, in the manufacture of gramophone records. (10) A mixture of methacrylic acid methyl ester, methyl cellulose, a phenol-formaldehyde condensation product and ferric oxide is polymerised in the presence of a solvent for the product such as acetone. (11) A solution of methacrylic acid methyl ester and nitrile and vinyl acetate in acetic esters is polymerised by means of sodium peroxide and mixed, after removal of the solvent, with sulphur and kaolin. (12) A mixture of a solution of cellulose acetate in acetone and polymerised methacrylic acid methyl ester in benzene is used for the production of artificial silk. (13) Lacquers are prepared from polymethacrylic acid methyl esters, dibutyl phthalate and benzene or polymethacrylic acid ethyl esters, methyl glycol phthalate, ethyl acetate and titanium dioxide. Specifications 355,712, 358,534, and 371,812, [Group V], are referred to. Reference has been directed by the Comptroller to Specification 395,687.ALSO:Plastic masses are prepared by incorporating wholly or partially polymerised methacrylic acid methyl ester or ethyl ester with one another and/or with one or more additional substance at any stage in the polymerisation which may be effected if desired in solution or in aqueous emulsion and with the aid of catalysts. The term additional substance includes softeners such as phthalic, tartaric, phosphoric and stearic acid esters, acetin, drying and non-drying oils, camphor and naphthalene, hardeners such as paraformaldehyde, plastifiers, products of methacrylic acid or its derivatives differing from those which form the basic constituents of the mass such as methacrylic acid nitrile, polyvinyl alcohols, or
GB1240232A 1932-04-29 1932-04-29 Improvements in or relating to the manufacture of plastic masses from methacrylic acid esters Expired GB401653A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1240232A GB401653A (en) 1932-04-29 1932-04-29 Improvements in or relating to the manufacture of plastic masses from methacrylic acid esters

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1240232A GB401653A (en) 1932-04-29 1932-04-29 Improvements in or relating to the manufacture of plastic masses from methacrylic acid esters

Publications (1)

Publication Number Publication Date
GB401653A true GB401653A (en) 1933-10-30

Family

ID=10003918

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1240232A Expired GB401653A (en) 1932-04-29 1932-04-29 Improvements in or relating to the manufacture of plastic masses from methacrylic acid esters

Country Status (1)

Country Link
GB (1) GB401653A (en)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE745131C (en) * 1935-10-04 1944-02-26 Rheinische Draht Und Kabelwerk Telecommunication field cable with normal overall thickness of the conductor sheathing
US2427847A (en) * 1940-04-06 1947-09-23 Goodrich Co B F Pyrophosphates in emulsion polymerization
US2496935A (en) * 1940-06-07 1950-02-07 Wingfoot Corp Copolymers of butadiene and monocyclic terpene alcohol esters of acrylic acids
DE756596C (en) * 1940-10-15 1951-04-02 Westfaelische Metall Ind Ag Li Cover lens for vehicle signal lights made of transparent or translucent synthetic resin or a similar elastic material
DE747596C (en) * 1935-02-21 1952-09-22 Roehm & Haas G M B H Process for polymerizing vinyl, acrylic and methacrylic compounds
DE900612C (en) * 1934-09-17 1953-12-28 Ici Ltd Process for the production of granular or spherical polymerisation products
DE964476C (en) * 1935-07-19 1957-05-23 Elastic Stop Nut Corp Pressed reflector, especially for traffic signs
DE976769C (en) * 1953-12-29 1965-09-23 Licentia Gmbh Record mass
DE1264653B (en) * 1958-11-28 1968-03-28 Ici Ltd Production of sliding coatings on metal sheets to be deformed

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE900612C (en) * 1934-09-17 1953-12-28 Ici Ltd Process for the production of granular or spherical polymerisation products
DE747596C (en) * 1935-02-21 1952-09-22 Roehm & Haas G M B H Process for polymerizing vinyl, acrylic and methacrylic compounds
DE964476C (en) * 1935-07-19 1957-05-23 Elastic Stop Nut Corp Pressed reflector, especially for traffic signs
DE745131C (en) * 1935-10-04 1944-02-26 Rheinische Draht Und Kabelwerk Telecommunication field cable with normal overall thickness of the conductor sheathing
US2427847A (en) * 1940-04-06 1947-09-23 Goodrich Co B F Pyrophosphates in emulsion polymerization
US2496935A (en) * 1940-06-07 1950-02-07 Wingfoot Corp Copolymers of butadiene and monocyclic terpene alcohol esters of acrylic acids
DE756596C (en) * 1940-10-15 1951-04-02 Westfaelische Metall Ind Ag Li Cover lens for vehicle signal lights made of transparent or translucent synthetic resin or a similar elastic material
DE976769C (en) * 1953-12-29 1965-09-23 Licentia Gmbh Record mass
DE1264653B (en) * 1958-11-28 1968-03-28 Ici Ltd Production of sliding coatings on metal sheets to be deformed

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