GB630632A - New polymerisable compositions and polymers thereof - Google Patents

New polymerisable compositions and polymers thereof

Info

Publication number
GB630632A
GB630632A GB13636/47A GB1363647A GB630632A GB 630632 A GB630632 A GB 630632A GB 13636/47 A GB13636/47 A GB 13636/47A GB 1363647 A GB1363647 A GB 1363647A GB 630632 A GB630632 A GB 630632A
Authority
GB
United Kingdom
Prior art keywords
esters
mixture
methacrylic
glycols
acid
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
GB13636/47A
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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 EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB630632A publication Critical patent/GB630632A/en
Expired legal-status Critical Current

Links

Classifications

    • FMECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F17STORING OR DISTRIBUTING GASES OR LIQUIDS
    • F17CVESSELS FOR CONTAINING OR STORING COMPRESSED, LIQUEFIED OR SOLIDIFIED GASES; FIXED-CAPACITY GAS-HOLDERS; FILLING VESSELS WITH, OR DISCHARGING FROM VESSELS, COMPRESSED, LIQUEFIED, OR SOLIDIFIED GASES
    • F17C13/00Details of vessels or of the filling or discharging of vessels
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/08Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • 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
    • C08F22/1006Esters of polyhydric alcohols or polyhydric phenols, e.g. ethylene glycol dimethacrylate

Abstract

Copolymers are prepared by the polymerization of the methacrylic di-esters of a mixture of glycols having the general formula HO-(CH2-CH2-O)nH, where n is an integer generally from 1 to 20, said mixture of glycols having an average molecular weight between 185 and 275 and preferably between 185 and 215. The comonomeric compositions are prepared by esterification of an appropriate mixture of the glycols with the acid (see Group IV (b)) or by mixing the performed esters. Polymerization may be effected by the action of heat, light, ozone, peroxy compounds and the like and in bulk, aqueous dispersion or emulsion or in a suitable solvent. Prior to polymerization, there may be added to the mixture other monomers or their polymers or copolymers such as acrylic and alkacrylic esters, for example methylacrylate, methyl-, ethyl- and butyl-methacrylate and methyl ethacrylate, and their derivatives; vinyl esters, for example vinyl acetate; vinyl halides, for example vinyl chloride and vinyl ester-halides; and cellulose derivatives, for example cellulose nitrate and acetate; also pigments, dyes, fillers, polymerization inhibitors and activators and solvents. The comonomer compositions may be cast into shaped articles possessing high heat distortion temperatures; they may be used in the construction of shoe stiffeners and to form scratch-resistant surface coatings on optical pieces; also they yield laminating and bonding compositions for bonding plywood and fibrous materials, e.g. glass fibres. In examples: (1) methacrylic di-esters of a mixture of polyethylene glycols (average M.W. 200) are heated with benzoyl peroxide to form a hard transparent copolymer; (2) a 50 : 50 mixture of the methacrylic di-esters of diethylene glycol and of a mixture of polyethylene glycols (average M.W. 400) is polymerized in a glass cell by means of heat in the presence of benzoyl peroxide. The properties of the resulting sheet are compared with those of sheets obtained similarly from the methacrylic di-esters of diethylene glycol and of mixtures of polyethylene glycols having average molecular weights of 180, 281, 324 and 400 respectively. Specification 423,790 is referred to.ALSO:Methacrylic di-esters are prepared by reacting a mixture of glycols having the formula HO-(CH2-CH2-O)nH, wherein n is an integer generally from 1 to 20, said mixture of glycols having an average molecular weight between 185 and 270, with methacrylic acid using the proportions to yield di-esters. The reaction may be carried out in a hydrocarbon solution using for example, benzene, hexane, heptane, toluene or methyl cyclohexane, in the presence of an acid catalyst such as sulphuric acid or p-toluene sulphonic acid and a polymerization inhibitor, for example hydroquinone, resorcinol or pyrogallol. If desired, the solution may be treated with activated carbon and a filter aid to remove resinous material and improve the colour. The mixture of esters, which may also be made by mixing preformed esters, may be polymerized to a co-polymer (see Group IV (a)). In an example, a mixture of polyethylene glycols of average molar weight 200\sB15 is heated with methacrylic acid in benzene solution in presence of sulphuric acid and hydroquinone in a flask equipped for removal of the water of esterification and return of the benzene carrier and the reaction product is worked up by aqueous sodium hydroxide and water washing and distillation to remove solvent so yielding a comonomeric mixture of methacrylic di-esters of the glycols. Specification 423,790 is referred to.
GB13636/47A 1946-05-21 1947-05-21 New polymerisable compositions and polymers thereof Expired GB630632A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US630632XA 1946-05-21 1946-05-21

Publications (1)

Publication Number Publication Date
GB630632A true GB630632A (en) 1949-10-18

Family

ID=22046670

Family Applications (1)

Application Number Title Priority Date Filing Date
GB13636/47A Expired GB630632A (en) 1946-05-21 1947-05-21 New polymerisable compositions and polymers thereof

Country Status (1)

Country Link
GB (1) GB630632A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4295762A (en) * 1979-02-21 1981-10-20 Nalco Chemical Company Grouting-soil conditioning systems using polyoxyethylene diacrylates
EP0331845A2 (en) * 1988-03-07 1989-09-13 Hoechst Celanese Corporation Accelerated preparation of acrylate esters

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4295762A (en) * 1979-02-21 1981-10-20 Nalco Chemical Company Grouting-soil conditioning systems using polyoxyethylene diacrylates
EP0331845A2 (en) * 1988-03-07 1989-09-13 Hoechst Celanese Corporation Accelerated preparation of acrylate esters
EP0331845A3 (en) * 1988-03-07 1991-06-05 Hoechst Celanese Corporation Accelerated preparation of acrylate esters

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