GB830799A - Improvements in and relating to the preparation of synthetic fibre-forming polyamides and polyamides prepared thereby - Google Patents

Improvements in and relating to the preparation of synthetic fibre-forming polyamides and polyamides prepared thereby

Info

Publication number
GB830799A
GB830799A GB10936/57A GB1093657A GB830799A GB 830799 A GB830799 A GB 830799A GB 10936/57 A GB10936/57 A GB 10936/57A GB 1093657 A GB1093657 A GB 1093657A GB 830799 A GB830799 A GB 830799A
Authority
GB
United Kingdom
Prior art keywords
dimethyl
heated
refluxed
isocinchomeronate
diamine
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
GB10936/57A
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.)
MINISTRY OF INTERNAT TRADE AND
National Institute of Advanced Industrial Science and Technology AIST
Original Assignee
MINISTRY OF INTERNAT TRADE AND
Agency of Industrial Science and Technology
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 MINISTRY OF INTERNAT TRADE AND, Agency of Industrial Science and Technology filed Critical MINISTRY OF INTERNAT TRADE AND
Publication of GB830799A publication Critical patent/GB830799A/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
    • C08G69/265Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids from at least two different diamines or at least two different dicarboxylic acids
    • 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
    • C08G59/00Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/42Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
    • C08G59/4246Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof polymers with carboxylic terminal groups
    • C08G59/4269Macromolecular compounds obtained by reactions other than those involving unsaturated carbon-to-carbon bindings
    • 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
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00Compositions of epoxy resins; Compositions of derivatives of epoxy resins

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

Synthetic fibre-forming polyamides are made by condensing an aliphatic normal diprimary diamine having four to ten carbon atoms, a lower dialkyl ester of isocinchomeronic acid and a lower dialkyl ester of an aliphatic dicarboxylic acid having two to ten carbon atoms, by reacting at a temperature of 50 DEG to 150 DEG C. and than at a temperature of 200 DEG to 300 DEG C., under reduced pressure, the mols. of diamine being equal to within \sB 5 mol. per cent to the sum of mols. of isocinchomeronic acid ester and mols. of aliphatic dicarboxylic acid ester, and the molar ratio of isocinchomeronic acid ester to aliphatic dicarboxylic acid ester being in the range 30:70 to 80:20. Lower alkyls are defined as methyl, ethyl, propyl or butyl. The polymers may be made by condensing the three components together or by condensing the diamine with one of the components and then with the remaining reactant. Reaction solvents specified are methanol, ethanol, butanol, and acetone. Specified diamines are tetra-, penta-, hexa-, hepta-, octa-, nona- and decamethylene diamine. Specified dicarboxylic acids are oxalic, malonic, succinic, glutaric, adipic, pimelic, suberic, azelaic and sebacic acid. Viscosity stabilizers, e.g. aliphatic or aromatic alkyl esters, may be present in the reaction mixture. The products of the invention may be heated to temperatures 30 DEG C. above their melting-points and drawn into filaments, the filaments being drawn in hot water or air heated to 100 DEG to 150 DEG C. to three or four times their original length and annealed at 220 DEG C. for about 30 minutes. In the examples: (1) dimethyl isocinchomeronate, dimethyl adipate and hexamethylene diamine are dissolved in ethanol and heated firstly under reflux and then at 255 DEG to 265 DEG C. under reduced pressure to give a polyamide; (II) hexamethylene diamine and dimethyl isocinchomeronate are heated under reflux in ethanol, the product being reacted with diethyl oxalate to form a pre-polymer which is further heated at 235 DEG to 240 DEG C. to form a polyamide; (III) the 2-component prepolymer of Example (II) is refluxed with dimethyl adipate in ethanol, the resultant prepolymer being heated at 260 DEG to 270 DEG C. to give a polyamide; (IV) diethyl malonate and hexamethylene diamine are refluxed in methanol, dimethyl isocinchomeronate and methanol are added and the mixture refluxed and then heated under reduced pressure; (V) hexamethylene diamine and dimethyl adipate are refluxed with methanol, dimethyl isocinchomeronate is added and the refluxing continued to give a prepolymer which is further condensed by heating in the presence of nitrogen at 250 DEG to 275 DEG C. under reduced pressure; (VI) is similar to (V) but with the addition of methyl benzoate during the second reflux; (VII) tetramethylene diamine and dimethyl adipate are refluxed in ethanol, dimethyl isocinchomeronate is added and the mixture is refluxed and condensed under reduced pressure to form a polyamide; (VIII) decamethylene diamine and diethyl sebacate are refluxed in butanol, dimethyl isocinchomeronate is added and the mixture refluxed and then heated to form a polyamide; (IX) decamethylene diamine and dimethyl adipate are refluxed in ethanol, dimethyl isocinchomeronate is added and the mixture refluxed and then heated to form a polyamide; (X) hexamethylene diamine, dimethyl azelate and dimethyl isocinchomeronate are refluxed in methanol, the methanol evaporated off and the product heated to form a polyamide; (XI) hexamethylene diamine and dimethyl isocinchomeronate are refluxed in ethanol, diethyl oxalate is added and the mixture condensed to form a polyamide; and (XII) tetramethylene diamine and dimethyl azelate are refluxed in ethanol, dimethyl isocinchomeronate is added and the mixture heated to form a polyamide. The products of the examples are (I) to (III), (V) to (VII) and (IX) to (XII) spun into filaments, the filaments being (V) and (VI) drawn in boiling water and heated under strain in air at 150 DEG C.; (VII) drawn in a water bath at 80 DEG C. and heated in air at 150 DEG C.; and (XI) drawn in a water bath at 60 DEG C. and heated at 150 DEG C.
GB10936/57A 1956-06-20 1957-04-03 Improvements in and relating to the preparation of synthetic fibre-forming polyamides and polyamides prepared thereby Expired GB830799A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP1598156 1956-06-20
JP1934956 1956-07-25
JP2793956 1956-11-02

Publications (1)

Publication Number Publication Date
GB830799A true GB830799A (en) 1960-03-23

Family

ID=29424877

Family Applications (1)

Application Number Title Priority Date Filing Date
GB10936/57A Expired GB830799A (en) 1956-06-20 1957-04-03 Improvements in and relating to the preparation of synthetic fibre-forming polyamides and polyamides prepared thereby

Country Status (3)

Country Link
CH (1) CH372467A (en)
DE (1) DE1096602B (en)
GB (1) GB830799A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1520195B1 (en) * 1963-05-25 1971-05-19 Kanegafuchi Spinning Co Ltd METHOD FOR MANUFACTURING COMPOSED POLYAMIDES AND THEIR USE FOR CRIMPED CONJUGATED POLYAMIDE FIBERS
EP2135891A3 (en) * 2008-05-28 2012-01-18 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Polyamide and method for its manufacture
CN116253872A (en) * 2021-12-10 2023-06-13 上海凯赛生物技术股份有限公司 High-temperature-resistant polyamide resin and preparation method thereof

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1570330A1 (en) * 1965-01-23 1969-12-11 Witten Gmbh Chem Werke Process for the preparation of mixed polyamides of oxalic acid with isophthalic acid and terephthalic acid in fine-grained form

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1520195B1 (en) * 1963-05-25 1971-05-19 Kanegafuchi Spinning Co Ltd METHOD FOR MANUFACTURING COMPOSED POLYAMIDES AND THEIR USE FOR CRIMPED CONJUGATED POLYAMIDE FIBERS
EP2135891A3 (en) * 2008-05-28 2012-01-18 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Polyamide and method for its manufacture
DE102008025029B4 (en) * 2008-05-28 2019-05-23 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Polyamide and process for its preparation
CN116253872A (en) * 2021-12-10 2023-06-13 上海凯赛生物技术股份有限公司 High-temperature-resistant polyamide resin and preparation method thereof

Also Published As

Publication number Publication date
CH372467A (en) 1963-10-15
DE1096602B (en) 1961-01-05

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