GB627733A - Linear polyamide condensation products - Google Patents
Linear polyamide condensation productsInfo
- Publication number
- GB627733A GB627733A GB37251/46A GB3725146A GB627733A GB 627733 A GB627733 A GB 627733A GB 37251/46 A GB37251/46 A GB 37251/46A GB 3725146 A GB3725146 A GB 3725146A GB 627733 A GB627733 A GB 627733A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acids
- acid
- dipropionic
- arylene
- phenylene
- 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
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
Abstract
A linear polyamide is made by heating an aliphatic diamine with arylene dipropionic acids, or their derivatives, having the structural formula R1-(CH2)2-R-(CH2)2-R1, where R is an arylene radical, and R1 is COOH, CONH2, COCl or CN. The oxa- and thiaderivatives of the radical R may be used. Heating, preferably of an initially-formed salt, is continued in an inert atmosphere until the product has an intrinsic viscosity of 0.2 to 1.5, the temperature being increased periodically to keep the mass liquid. Filaments may be formed as by extrusion of the melted polyamide into a dry atmosphere or a liquid bath, and cold-drawn to between 300 and 600 per cent. The permanent set, or residual elongation at the breaking point, of these filaments is lower than in other types of polyamide, being 8.2 and 8.6 per cent in two examples. They are thus useful for fabrication with rubber as in the making of tyres, where it is desirable to have fibres with a residual elongation of less than 10 per cent. The filaments may be spun and woven into fabrics or used in the manufacture of brushes and the like or thin sheets may be extruded or solution-cast for use as wrapping films. Examples of acids are p-phenylene-, and 1,2-naphthalene-dipropionic acid and R in the above formula may be o, m and p-phenylene; the diphenylenes; the naphthylenes; the toluylenes; and their alkyl-substituted derivatives and the corresponding anthracene; phenanthrene; diphenyl and other aromatic hydrocarbon radicals. Acids derived from oxa- and thia-hydrocarbons such as diphenyl ether; diphenyl sulphide; alkoxybenzenes; and mixed aryl alkyl sulphides may be used, as may derivatives of the acids such as amides, acid anhydrides, acid chlorides, esters and nitriles. Examples of diamines are hexamethylene and decamethylene diamine; and compounds containing oxygen and sulphur such as triglycol diamine and di-(3-aminopropyl)-sulphide and their homologues. Arylene dipropionic acids may be prepared by the malonic ester synthesis from compounds of structure CH3-R-CH3 by halogenation to (BrCH2)2R, followed by condensation with ethyl malonate to give a condensed ester [(C2H5OOC)2CH-CH2]2R, which is hydrolysed to the corresponding acid, the latter being then pyrolized to split out CO2 and form the arylene dipropionic acid. They may also be prepared by Claisen condensations from halogen compounds of the type Br2-CHR-CH-Br2 which are hydrolysed to the dialdehyde OHC-R-CHO which is then condensed with ethyl acetate to give (C2H5OOC-CH=CH)2R, the latter being then hydrogenated to saturate the double bond, and hydrolysed. In specific examples polyamides from the salt of decamethylene diamine, or of hexamethylene diamine, and p-phenylene dipropionic acid, are compared in properties with polyamides from the same amines and p-phenylene diacetic acid. The Specification as open to inspection under Sect. 91 comprises also the use of acids of structure R1-(CH2)x-R-(CH2)x-R1 where x is a whole number greater than 1 and preferably from 2 to 6. This subject-matter does not appear in the Specification as accepted.ALSO:In making a linear polyamide (see Group IV (a)), an aliphatic diamine is heated with arylene dipropionic acids, or their derivatives, having the structural formula <FORM:0627733/IV (b)/1> where R is an arylene radical and R1 is COOH, CONH2, COCl or CN. The oxa- and thia-derivatives of the radical R may be used. Examples of acids are p-phenylene- and 1.2-naphthalene-dipropionic acid and R in the above formula may be o, m and p-phenylene; the diphenylenes; the naphthylenes; the toluylenes; and their alkyl-substituted derivatives and the corresponding anthracene; phenanthrene; diphenyl and other aromatic hydrocarbons radicals. Acids derived from oxa- and thia-hydrocarbons such as diphenyl ether; diphenyl sulphide; alkoxybenzenes; and mixed aryl alkyl sulphides may be used, as may derivatives of the acids such as amides, acid anhydrides, acid chlorides, esters and nitriles. Arylene dipropionic acids may be prepared by the malonic ester synthesis from compounds of structure CH3-R-CH3 by halogenation to (Br CH2)2 R followed by condensation with ethyl malonate to give a condensed ester [(C2H5OOC)2CH-CH2]2R which is hydrolysed to the corresponding acid, the latter being then pyrolized to split out CO2 and form the arylene dipropionic acid. They may also be prepared by Claisen condensations from halogen compounds of the type Br2-CH-R-CH-Br2 which are hydrolysed to the dialdehyde OHC-R-CHO which is then condensed with ethyl acetate to give (C2H5OOC-CH=CH)2 R the latter being then hydrogenated to saturate the double bond, and hydrolysed. In specific examples polyamides from the salt of decamethylene diamine, or of hexamethylene diamine, and p-phenylene dipropionic acid, are compared in properties with polyamides from the same amines and p-phenylene diacetic acid. The Specification as open to inspection under Sect. 91 comprises also the use of acids of structure R1-(CH2)x-R-(CH2)x-R1, where a is a whole number greater than 1 and preferably from 2 to 6. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US627733XA | 1946-06-07 | 1946-06-07 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB627733A true GB627733A (en) | 1949-08-15 |
Family
ID=22044703
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB37251/46A Expired GB627733A (en) | 1946-06-07 | 1946-12-18 | Linear polyamide condensation products |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB627733A (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3126362A (en) * | 1964-03-24 | Synthetic linear polyamides from | ||
US3143530A (en) * | 1961-04-19 | 1964-08-04 | Union Carbide Corp | Linear polycarbonamides from piperazines and fluorene dicarboxylic acids |
US3197444A (en) * | 1960-07-13 | 1965-07-27 | Du Pont | Thermally stable polyamides from substituted aromatic dialkanoic acids |
US3335114A (en) * | 1963-09-13 | 1967-08-08 | Monsanto Co | Polycarbonamides from p-phenylenebis(dimethylacetic acid) and its derivatives |
US3475387A (en) * | 1963-08-31 | 1969-10-28 | British Nylon Spinners Ltd | Manufacture of polyamides from aromatic dicarboxylic acids |
-
1946
- 1946-12-18 GB GB37251/46A patent/GB627733A/en not_active Expired
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3126362A (en) * | 1964-03-24 | Synthetic linear polyamides from | ||
US3197444A (en) * | 1960-07-13 | 1965-07-27 | Du Pont | Thermally stable polyamides from substituted aromatic dialkanoic acids |
US3143530A (en) * | 1961-04-19 | 1964-08-04 | Union Carbide Corp | Linear polycarbonamides from piperazines and fluorene dicarboxylic acids |
US3475387A (en) * | 1963-08-31 | 1969-10-28 | British Nylon Spinners Ltd | Manufacture of polyamides from aromatic dicarboxylic acids |
US3335114A (en) * | 1963-09-13 | 1967-08-08 | Monsanto Co | Polycarbonamides from p-phenylenebis(dimethylacetic acid) and its derivatives |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US2191556A (en) | Polyamides | |
US3184436A (en) | Polycarbonamides of improved dye affinity having the benzene sulfonic acid salt moiety as an integral part of the polymer chain | |
US3142662A (en) | Modified polyamides containing the benzenesulfonate moiety | |
US2293388A (en) | Polyamides and their preparation | |
US3491042A (en) | Stabilized polyamide composition containing copper salts and metal cyanides | |
DE2802989A1 (en) | HYDROLYSIS-RESISTANT COPOLYAETHERESTERAMIDE | |
US2214442A (en) | Synthetic polymer | |
DE1795464B2 (en) | Process for the production of essentially amorphous, transparent polyamides | |
EP0327700B1 (en) | Mouldings made of aromatically processable thermoplastic polyamide | |
Bock et al. | Linear polyesters derived from vanillic acid | |
US2276437A (en) | Polymeric Materials | |
US2754284A (en) | Synthetic linear polyamides containing intralinear siloxane groups and preparation | |
DE2628776A1 (en) | DIRT-REPELLENT AGENT AND ITS USE | |
GB627733A (en) | Linear polyamide condensation products | |
US3304289A (en) | Modified polyamides having improved affinity for dyes | |
US2296555A (en) | Process for the production of synthetic polyamides | |
IE52231B1 (en) | Poly-para-phenyleneterephthalamide compositions,their preparation and their use | |
DE739001C (en) | Process for the production of polyamides suitable for plastics | |
SU1496636A3 (en) | Copolyamide | |
US2623034A (en) | Crystalline tetramethylene isophthalate polymer | |
US2281576A (en) | Polyamides and process of making same | |
KR880006286A (en) | Elastomer | |
DE1295826B (en) | Process for the production of oxidation-resistant polyamides | |
DE2449664A1 (en) | Melt formable polyamide prepn - by polycondensing naphthalene-2,6-dicarboxylic acid and amine components | |
US3485805A (en) | N-alkyl substituted polyamide elastomers |