GB467492A - Condensation products of methacrylamide and formaldehyde - Google Patents
Condensation products of methacrylamide and formaldehydeInfo
- 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
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
- 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
- C08F20/52—Amides or imides
- C08F20/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F20/56—Acrylamide; Methacrylamide
-
- 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
- C08F8/00—Chemical modification by after-treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Moulding By Coating Moulds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymerisation Methods In General (AREA)
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.
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)
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)
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 |
DE3277539D1 (en) * | 1981-06-01 | 1987-12-03 | American Cyanamid Co | 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 |
US5120531A (en) * | 1990-04-06 | 1992-06-09 | The Procter & Gamble Company | Hair styling conditioners |
US5120532A (en) * | 1990-04-06 | 1992-06-09 | The Procter & Gamble Company | Hair styling shampoos |
-
1935
- 1935-11-11 GB GB3115035A patent/GB467492A/en not_active Expired
- 1935-11-11 GB GB1400437A patent/GB467402A/en not_active Expired
Cited By (14)
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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