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GB627733A - Linear polyamide condensation products - Google Patents

Linear polyamide condensation products

Info

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
Application number
GB37251/46A
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.)
Wingfoot Corp
Original Assignee
Wingfoot Corp
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 Wingfoot Corp filed Critical Wingfoot Corp
Publication of GB627733A publication Critical patent/GB627733A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G69/00Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/02Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
    • C08G69/26Polyamides 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.
GB37251/46A 1946-06-07 1946-12-18 Linear polyamide condensation products Expired GB627733A (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (5)

* Cited by examiner, † Cited by third party
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

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