GB467492A - Condensation products of methacrylamide and formaldehyde - Google Patents

Condensation products of methacrylamide and formaldehyde

Info

Publication number
GB467492A
GB467492A GB3115035A GB3115035A GB467492A GB 467492 A GB467492 A GB 467492A GB 3115035 A GB3115035 A GB 3115035A GB 3115035 A GB3115035 A GB 3115035A GB 467492 A GB467492 A GB 467492A
Authority
GB
United Kingdom
Prior art keywords
formaldehyde
methacrylamide
aqueous
esters
solution
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
GB3115035A
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
Publication of GB467492A publication Critical patent/GB467492A/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
    • C08F20/52Amides or imides
    • C08F20/54Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • C08F20/56Acrylamide; Methacrylamide
    • 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
    • C08F8/00Chemical modification by after-treatment

Abstract

Methacrylamide, mixtures thereof with one or more acrylic or vinyl compounds, or corresponding polymers, are condensed with formaldehyde, which may be in aqueous or other solution, as vapour, or as paraformaldehyde. Polymerization and condensation may take place simultaneously. The acrylic or vinyl compounds include vinyl chloride or acetate; styrene; acrylic nitrile; methyl, ethyl, butyl or amyl acrylate; or methacrylic compounds. There may be incorporated one or more polyhydric alcohols, e.g. glycol, glycerol; metal salts, e.g. aluminium formate, acetate or sulphate, or zinc chloride; softening agents, e.g. acetins, phthalic esters, adipic esters drying and non-drying oils, fats, waxes, and fatty acids; cellulose compounds, e.g. ethers and esters; natural and artificial resins, e.g. urea-, phenol-, and p-toluenesulphonamidealdehyde resins; rubber, e.g. latex; gelatine, glue, or starch. The products may be used as glass substitutes and interlayers for safety glass; moulded, cut, or turned articles; lacquers; textile assistants; thickening agents, e.g. for dyes; protective colloids for latex; gelatine substitutes, e.g. for photographic or printing purposes; electrical insulation and cable casings; adhesives; gas-impermeable fabrics, e.g. for gas-masks; medical purposes, e.g. palates, plaster; artificial leather, artificial silk; gramophone records. Films of the products may be used alone, e.g. for membranes and tubes; be applied to other films, especially those non-permeable to water, e.g. of cellulose ester, especially celluloid, of polyvinyl esters, polystyrene, polyacrylic or polymethacrylic esters, of interpolymers and mixtures of polymers; or be used as intermediate layers coated with other materials, e.g. polyacrylic ester, and may contain a solvent for the coatings. In examples: (1) an aqueous solution of polymethacrylamide, glycerine, formaldehyde, boric acid, and aluminium formate is heated, then poured on to a glass plate to produce films or slabs; (2) methacrylamide is heated with paraformaldehyde in toluene solution; (3), (4), a film is prepared by evaporating an aqueous solution of polymethacrylamide and glycerine, and is (3) immersed in aqueous formaldehyde, (4) suspended in formaldehyde vapour; (5) aqueous formaldehyde and methacrylamide solutions are heated together; (6) methacrylamide is polymerized in aqueous solution in the presence of hydrogen peroxide, and treated with aqueous formaldehyde; (7) methacrylamide and butyl acrylate are polymerized in ethyl, propyl or butyl alcohol solution in the presence of benzoyl peroxide, and the polymer treated with paraformaldehyde, (instead of an alcohol, there may be used a ketone, e.g. acetone, methyl ethyl ketone); (8) a film of the polymer of example 7 treated with paraformaldehyde gave an alcohol-soluble film, insolubilized by treatment with aqueous formaldehyde. Specification 467,402 is referred to. According to the Provisional Specification interpolymers may be prepared with polymerizable, unsaturated organic compounds in general; and there may be added to the products polyvinyl alcohol, polyacrylic and polymethacrylic acids and esters.ALSO:Protective colloids for latex may be prepared from methacrylamide, mixtures thereof with one or more acrylic or vinyl compounds, or corresponding polymers by condensation with formaldehyde, which may be in aqueous or other solution, as vapour, or as parafommaldehyde. Specification 467,402, is referred to.
GB3115035A 1935-11-11 1935-11-11 Condensation products of methacrylamide and formaldehyde Expired GB467492A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1400437A GB467402A (en) 1935-11-11 1935-11-11 Improvements in or relating to the manufacture and use of interpolymers of methacrylic acid amide

Publications (1)

Publication Number Publication Date
GB467492A true GB467492A (en) 1937-06-11

Family

ID=10033255

Family Applications (2)

Application Number Title Priority Date Filing Date
GB3115035A Expired GB467492A (en) 1935-11-11 1935-11-11 Condensation products of methacrylamide and formaldehyde
GB1400437A Expired GB467402A (en) 1935-11-11 1935-11-11 Improvements in or relating to the manufacture and use of interpolymers of methacrylic acid amide

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB1400437A Expired GB467402A (en) 1935-11-11 1935-11-11 Improvements in or relating to the manufacture and use of interpolymers of methacrylic acid amide

Country Status (1)

Country Link
GB (2) GB467492A (en)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2680110A (en) * 1952-04-17 1954-06-01 American Cyanamid Co Copolymers of nu-methylol acrylamide
DE953916C (en) * 1942-10-22 1956-12-06 Bayer Ag Process for improving the shrinkage resistance of molded products made of polyacrylic acid nitrile
DE956890C (en) * 1954-04-03 1957-01-24 Basf Ag Process for the production of water-soluble macromolecular methylol compounds from copolymers
DE1054710B (en) * 1956-03-01 1959-04-09 Basf Ag Process for the production of etherified condensation products
DE1060596B (en) * 1956-03-01 1959-07-02 Basf Ag Process for the production of etherified condensation products
DE1094455B (en) * 1959-07-23 1960-12-08 Basf Ag Process for the production of stable, water-soluble, powder-form copolymers containing N-methylol groups
US2978437A (en) * 1957-06-12 1961-04-04 Pittsburgh Plate Glass Co Water-insoluble condensation products of aldehydes and acrylamide interpolymers
US3037963A (en) * 1955-02-24 1962-06-05 Pittsburgh Plate Glass Co Resinous materials
US3079434A (en) * 1958-11-21 1963-02-26 Pittsburgh Plate Glass Co Method of making water insoluble unsaturated amides
US3118853A (en) * 1955-02-24 1964-01-21 Pittsburgh Plate Glass Co Compositions comprising a carboxylic acid amide interpolymer and an adduct of a hydroxyl-containing polymer and a carboxylic acid anhydride
US3247139A (en) * 1962-01-02 1966-04-19 Pittsburgh Plate Glass Co Interpolymers of etherified aldehydemodified carboxylic acid amides
US3271479A (en) * 1961-12-21 1966-09-06 Pittsburgh Plate Glass Co Resinous compositions of carboxylic amide interpolymers and unsaturated ester polymers
DE1242370B (en) * 1961-04-05 1967-06-15 DeSOTO CHEMICAL - COA TINGS, Inc, Chicago, 111 (V St A) Process for the step production of copolymers containing alkylol groups

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2816882A (en) * 1957-12-17 Ymeric surface active agents
US2533166A (en) * 1945-10-16 1950-12-05 Gen Aniline & Film Corp Process for polymerizing watersoluble polyacrylamides and poly-alpha-substituted acrylamides
BE468665A (en) * 1945-10-16
BE476083A (en) * 1946-07-22
GB655615A (en) * 1946-10-31 1951-07-25 American Cyanamid Co Improvements in or relating to polymerizable compositions
US2594579A (en) * 1948-08-14 1952-04-29 Borden Co Polystyrene interpolymers convertible to the infusible and insoluble state
CH283908A (en) * 1949-11-16 1952-06-30 Bayer Ag Method for taking impressions, in particular for dental purposes.
US2901468A (en) * 1952-11-08 1959-08-25 Wacker Chemie Gmbh Process for manufacturing nitrogen-containing polymerizates insoluble in water
DE954197C (en) * 1953-08-22 1956-12-13 Basf Ag Process for the production of high molecular weight, water-soluble products from methacrylic acid amide or its mixtures with unsaturated carboxylic acid amides
CA1178003A (en) * 1981-06-01 1984-11-20 Chi-Fei Ling Process for sizing textile materials
US5019377A (en) * 1987-12-11 1991-05-28 The Procter & Gamble Company Low glass transistion temperature adhesive copolymers for use in hair styling products
US4963348A (en) * 1987-12-11 1990-10-16 The Procter & Gamble Company Styling agents and compositions containing the same
DE3811053A1 (en) * 1988-03-31 1989-10-12 Basf Ag THERMAL-RESISTANT, TRANSPARENT THERMOPLASTIC SHAPED MATERIAL, METHOD FOR THEIR PRODUCTION AND THEIR USE
US5104642A (en) * 1990-04-06 1992-04-14 The Procter & Gamble Company Hair styling compositions containing particular hair styling polymers and non-aqueous solvents
US5120532A (en) * 1990-04-06 1992-06-09 The Procter & Gamble Company Hair styling shampoos
US5120531A (en) * 1990-04-06 1992-06-09 The Procter & Gamble Company Hair styling conditioners

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE953916C (en) * 1942-10-22 1956-12-06 Bayer Ag Process for improving the shrinkage resistance of molded products made of polyacrylic acid nitrile
US2680110A (en) * 1952-04-17 1954-06-01 American Cyanamid Co Copolymers of nu-methylol acrylamide
DE956890C (en) * 1954-04-03 1957-01-24 Basf Ag Process for the production of water-soluble macromolecular methylol compounds from copolymers
US3037963A (en) * 1955-02-24 1962-06-05 Pittsburgh Plate Glass Co Resinous materials
US3118852A (en) * 1955-02-24 1964-01-21 Pittsburgh Plate Glass Co Compositions comprising a carboxylic acid amide interpolymer and a hydroxyl-containing polymer
US3118853A (en) * 1955-02-24 1964-01-21 Pittsburgh Plate Glass Co Compositions comprising a carboxylic acid amide interpolymer and an adduct of a hydroxyl-containing polymer and a carboxylic acid anhydride
DE1054710B (en) * 1956-03-01 1959-04-09 Basf Ag Process for the production of etherified condensation products
DE1060596B (en) * 1956-03-01 1959-07-02 Basf Ag Process for the production of etherified condensation products
US2978437A (en) * 1957-06-12 1961-04-04 Pittsburgh Plate Glass Co Water-insoluble condensation products of aldehydes and acrylamide interpolymers
US3079434A (en) * 1958-11-21 1963-02-26 Pittsburgh Plate Glass Co Method of making water insoluble unsaturated amides
DE1094455B (en) * 1959-07-23 1960-12-08 Basf Ag Process for the production of stable, water-soluble, powder-form copolymers containing N-methylol groups
DE1242370B (en) * 1961-04-05 1967-06-15 DeSOTO CHEMICAL - COA TINGS, Inc, Chicago, 111 (V St A) Process for the step production of copolymers containing alkylol groups
US3271479A (en) * 1961-12-21 1966-09-06 Pittsburgh Plate Glass Co Resinous compositions of carboxylic amide interpolymers and unsaturated ester polymers
US3247139A (en) * 1962-01-02 1966-04-19 Pittsburgh Plate Glass Co Interpolymers of etherified aldehydemodified carboxylic acid amides

Also Published As

Publication number Publication date
GB467402A (en) 1937-06-11

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