GB534699A - Polymeric compounds suitable for filaments, films, coating compositions, plastics and the like - Google Patents
Polymeric compounds suitable for filaments, films, coating compositions, plastics and the likeInfo
- Publication number
- GB534699A GB534699A GB25701/39A GB2570139A GB534699A GB 534699 A GB534699 A GB 534699A GB 25701/39 A GB25701/39 A GB 25701/39A GB 2570139 A GB2570139 A GB 2570139A GB 534699 A GB534699 A GB 534699A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenol
- polyamines
- reacted
- filaments
- decamethylenediamine
- 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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/02—Polyureas
Abstract
534,699. Polyamides. DU PONT DE NEMOURS & CO., E. I. Sept. 13, 1939, No. 25701. Convention date, Sept., 15, 1938. [Class 2 (iii)] Polythioureas are formed by condensing polyamines, preferably diamines, with a thiourea-forming derivative of thiocarbonic acid until the product has an intrinsic viscosity of at least À12. The polyamines used have at least two amino groups containing hydrogen separated by at least four carbon atoms in an open chain, at least three carbon atoms in a monocylic body or at least four in a dicyclic body. Suitable condensation processes include (A) the heating of a polyamine with an ester of trithiocarbonic acid (B) the heating of carbon bisulphide with a polyamide (C) the heating of a bis (dithiocarbamate) with a diamine (D) the heating of ammonium thiocyanate of a diamine (E) The heating of a polyisothiocyanate with a polyamine. Other thiourea-forming derivatives of thiocarbonic acid that may be reacted with the polyamine include sulphanhydrates, thioamidos, acid halides, half esters, diesters (with alcohols or phenols). Specified polyamines that may be used include decamethylene,. diamine, hexamethylenediamine, diethylenetriamine, triethylenetetramine, di- (hexamethylene)-triamine, tetramethylenediamine, pentamethylenediamine, m-phenylenediamine, p - phenylenediamine, benzidine, m-toluylenediamines, 2:5-dimethyl-1:6-diaminohexane, 1:4-diaminocyclohexane, 1:10-bis (methylamino) decane, triglycoldiamine, thioglycoldiamine. Mixtures of polyamines and thiourea-forming derivatives may be used. The reaction, which may take place in the presence of a diluent such as a phenol, is preferably effected in the absence of oxygen by operating in vacuum, in the presence of an inert gas such as nitrogen, argon, helium or hydrogen or in the presence of antioxidants such as syringic acid. Excess of one reactant or small amounts of monoamines or monocarboxylic acids may be used in the reaction. The reaction vessels used may be constructed of, or lined with, glass, porcelain, enamel, silver, gold, tantalum, platinum, palladium, rhodium, alloys of platinum with palladium or rhodium and chromium-nickel steels. Catalysts such as sulphur may be used. The polythioureas may be converted in filaments by melt, wet or dry spinning and the filaments are preferably cold drawn ; they may be de-lustred, preferably by the addition of a finely divided material of different refractive index such as titanium dioxide, zinc oxide, zinc sulphide, barium sulphate, carbon black, copper phthalocyanine pigments or non-phenolic polymer clear compounds. The filaments, which may be set by steaming, may be worked up into woven or knitted fabrics and mixed fabrics with other fibres. The products may also be used in the manufacture of films, foils, sheets, ribbons, bands, rods, hollow tubes, interlayed for safety, glass and bristles. Addition of the polythiourea to a polyamide improves the properties of products therefrom. In examples: (1) decamethylenediamine or hexamethylenediamine is reacted with ethyl methyl trithiocarbonate to yield a polythiourea which may be converted into fibres direct from the melt or which may be cast into sheets by hot-pressing between plates covered with aluminium foil, the finished sheet being cold-rolled or directly sandwiched between two plates of glass and hot-pressed to yield a safety glass; (2) m-phenylenediamine is reacted with ethyl methyl trithiocarbonate in the presence or absence of phenol ; (3) decamethylenediamine is allowed to stand with ethyl methyl trithiocarbonate in the cold, dissolved in phenol and then heated ; (4) m-phenylenediamine is heated with ethyl methyl trithiocarbonate in the presence of phenol; (5) solutions of carbon disulphide and hexamethylenediamine in methanol are mixed and the precipitate obtained, after drying, is heated in the presence of phenol and of sulphur (as a catalyst)À,' (6) decamethylenediamine is reacted with dimethylhexamethylenebisdithiocarbonate in the presence of phenol ; (7) decamethylenediamine is.reacted with ammonium thiocyanate; (8) decamethylenediamine is reacted with decamethylene diisocyanate in the presence of cresol. In each example. the polymers may be. converted into filaments. Ethyl methyl trithiocarbonate is prepared by treating ethyl mercaptan with carbon di-. sulphide in the presence of aqueous potassium hydroxide and treating the. product with dimethyl sulphate. Alkyl mercaptans are prepared in the forma-. tion of the polythioureas by re-acting dialkyl trithiocarbonates with polyamines or by reacting bis(dithiocarbamates) with polyamines. Dimethylhexamethylene bis (dithiocarbamate) is prepared by treating hexamethylenediamine with carbon disulphide in the presence of aqueous potassium hydroxide and reacting the products with dimethyl sulphate.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US534699XA | 1938-09-15 | 1938-09-15 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB534699A true GB534699A (en) | 1941-03-14 |
Family
ID=21984471
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB25701/39A Expired GB534699A (en) | 1938-09-15 | 1939-09-13 | Polymeric compounds suitable for filaments, films, coating compositions, plastics and the like |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB534699A (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2816879A (en) * | 1951-11-15 | 1957-12-17 | Du Pont | Process for preparing polyureas utilizing immiscible phases |
US3046254A (en) * | 1960-06-02 | 1962-07-24 | Toyo Koatsu Ind Inc | Method for the preparation of polyureas |
US3054777A (en) * | 1958-05-16 | 1962-09-18 | Toyo Koatsu Ind Inc | Linear polyureas |
US3133897A (en) * | 1959-03-30 | 1964-05-19 | Toyo Koatsu Ind Inc | Production of polyurea copolymers from an alkylene diamine, a heteromembered alkylene diamine and a urea |
CN108570149A (en) * | 2017-06-21 | 2018-09-25 | 华南理工大学 | A kind of multicomponent polymerization of isonitrile, sulphur and amine prepares the method for polythiourea and the application of the polythiourea |
CN110551274A (en) * | 2019-08-06 | 2019-12-10 | 中山大学 | Intrinsic self-repairing and recyclable polythiourea polymer and preparation method and application thereof |
-
1939
- 1939-09-13 GB GB25701/39A patent/GB534699A/en not_active Expired
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2816879A (en) * | 1951-11-15 | 1957-12-17 | Du Pont | Process for preparing polyureas utilizing immiscible phases |
US3054777A (en) * | 1958-05-16 | 1962-09-18 | Toyo Koatsu Ind Inc | Linear polyureas |
US3133897A (en) * | 1959-03-30 | 1964-05-19 | Toyo Koatsu Ind Inc | Production of polyurea copolymers from an alkylene diamine, a heteromembered alkylene diamine and a urea |
US3046254A (en) * | 1960-06-02 | 1962-07-24 | Toyo Koatsu Ind Inc | Method for the preparation of polyureas |
CN108570149A (en) * | 2017-06-21 | 2018-09-25 | 华南理工大学 | A kind of multicomponent polymerization of isonitrile, sulphur and amine prepares the method for polythiourea and the application of the polythiourea |
CN108570149B (en) * | 2017-06-21 | 2020-05-22 | 华南理工大学 | Method for preparing polythiourea by multicomponent polymerization of isonitrile, sulfur and amine and application of polythiourea |
CN110551274A (en) * | 2019-08-06 | 2019-12-10 | 中山大学 | Intrinsic self-repairing and recyclable polythiourea polymer and preparation method and application thereof |
CN110551274B (en) * | 2019-08-06 | 2020-06-16 | 中山大学 | Intrinsic self-repairing and recyclable polythiourea polymer and preparation method and application thereof |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE745684C (en) | Process for the production of highly condensed polyamides from diamines and carbonic acid | |
US2191556A (en) | Polyamides | |
US2244192A (en) | Preparation of polyamides | |
US2284637A (en) | Polymeric carbamates and their preparation | |
US2208095A (en) | Process of producing insoluble condensation products containing sulphur and nitrogen | |
US2245129A (en) | Process for preparing linear polyamides | |
US2190770A (en) | Synthetic linear polyamides | |
US2292443A (en) | Process for preparing polymeric polyamides | |
DE1595089A1 (en) | Process for the production of deformable polyamide esters and molded articles from polyimides | |
DE1161007B (en) | Manufacture of synthetic resin films or threads | |
DE2951778A1 (en) | ISOMORPHIC COPOLYMERISATES OF EPSILON -CAPROLACTONE WITH 1,5-DIOXEPAN-2-ON AND THEIR USE | |
US2293388A (en) | Polyamides and their preparation | |
GB534699A (en) | Polymeric compounds suitable for filaments, films, coating compositions, plastics and the like | |
US2214442A (en) | Synthetic polymer | |
US2276437A (en) | Polymeric Materials | |
US2181663A (en) | Diurethane-diamine polymeric materials | |
US2313871A (en) | Polythiourea | |
US2660574A (en) | Process for the production of polyurethanes | |
DE2655620A1 (en) | PROCESS FOR MANUFACTURING AROMATIC POLYMERS | |
DE2737084A1 (en) | THERMOPLASTIC POLYSILOXANE ELASTOMERS | |
US3009764A (en) | Method of making polyurethane thread and thread produced by such method | |
US2281576A (en) | Polyamides and process of making same | |
US3645981A (en) | Process for preparing polythioureas | |
DE1720984A1 (en) | Polyamides and processes for their manufacture | |
DE2339865A1 (en) | POLYAMIDE CONCENTRATES CONTAINING SULFONATE GROUPS |