GB871578A - Improvements in or relating to the production of polyamides - Google Patents

Improvements in or relating to the production of polyamides

Info

Publication number
GB871578A
GB871578A GB6633/58A GB663358A GB871578A GB 871578 A GB871578 A GB 871578A GB 6633/58 A GB6633/58 A GB 6633/58A GB 663358 A GB663358 A GB 663358A GB 871578 A GB871578 A GB 871578A
Authority
GB
United Kingdom
Prior art keywords
triethylamine
phenylene diamine
aromatic
chloride
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
GB6633/58A
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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
Priority claimed from US713304A external-priority patent/US3063966A/en
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB871578A publication Critical patent/GB871578A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/09—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
    • C08J3/091—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids characterised by the chemical constitution of the organic liquid
    • 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
    • C08G69/32—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids from aromatic diamines and aromatic dicarboxylic acids with both amino and carboxylic groups aromatically bound
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
    • D01F6/60—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyamides
    • D01F6/605—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyamides from aromatic polyamides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2377/00—Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such polymers
    • C08J2377/10—Polyamides derived from aromatically bound amino and carboxyl groups of amino carboxylic acids or of polyamines and polycarboxylic acids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Polyamides (AREA)
  • Artificial Filaments (AREA)

Abstract

An aromatic polyamide having an inherent viscosity in concentrated sulphuric acid at 30 DEG C. of at least 0,6 and a melting point of at least 300 DEG C. is made by reacting at a temperature below 100 DEG C. a diamine component containing at least 90 mol per cent of an aromatic diamine, any remainder being non-aromatic diamine, and a diacid halide component containing at least 90 mol per cent of an aromatic diacid halide, any remainder being non-aromatic diacid halide, the amine groups in the aromatic diamine and the acid halide groups in the aromatic diacid halide not being ortho-oriented with respect to each other or to bonds linking one aromatic ring directly or through a linking group to another aromatic ring, the substituent groups (if any) in the aromatic rings being groups which do not react with the amine or acid halide groups during polymerization and the total number of carbon atoms in substituent groups attached to any one aromatic ring not exceeding nine, in the presence of an organic acid-acceptor, in a liquid reaction medium which is a solvent for each of the reactants and the acid-acceptor and which has an average solvent/solute interaction energy with complementary model compounds representative of the polyamide less than 1100 calories per mole. The term organic "acid-acceptor" is defined as being a compound which will effectively remove acidic by-products of the reaction without itself interfering with the polymerization and containing at least one organic carbon atom. The liquid reaction medium may also function as the acid-acceptor. The model compounds are diamides free from polyamide-forming terminal groups and having specified formulae. The Specification lists large numbers of aromatic diacid halides and aromatic diamines which may be used in the process of the invention. Specified solvents include chloroform, methylene chloride, 1, 1, 2-trichloroethane, 1, 2-dichloroethane, methyl ethyl ketone, acetonitrile, tetramethylene sulphone and propionitrile. Specified solvents which act as acid-acceptors include dimethyl acetamide, N, N, N1, N1-tetramethyl urea and N-ethyl pyrrolidone. The examples describe the preparation of polyamides from: (1) m-phenylene diamine hydrochloride and isophthaloyl chloride, (2) and (8) 4-methyl-m-phenylene diamine and isophthaloyl chloride, (3), (5), (6), (14), (15) and (20) to (25) m-phenylene diamine and isophthaloyl chloride, (4) bis-(4-aminophenyl) methane and isophthaloyl chloride, (7) m-phenylene diamine and 4-chloro-isophthaloyl chloride, (9) 4-methoxy-m-phenylene diamine and isophthaloyl chloride, (10) m-phenylene diamine, isophthaloyl chloride and terephthaloyl chloride, (11) m-phenylene diamine hydrochloride, p-phenylene diamine hydrochloride and isophthaloyl chloride, (12) terephthaloyl chloride and m-phenylene diamine, (13) 4, 41-sulphonyl-diphenyl-diamine or 2, 21-bis(4-aminophenyl) propane and isophthaloyl chloride, (16) m-phenylene diamine and terephthaloyl chloride, (17) 2, 2-bis(4-aminophenyl) propane and isophthaloyl chloride, (18) p-phenylene diamine and isophthaloyl chloride and (19) p-phenylene diamine and terephthaloyl chloride in the presence of: (1) triethylamine hydrochloride and methylene chloride, (2), (6), (7) and (8) triethylamine, triethylamine hydrochloride and methylene chloride, (3) tetramethylene sulphone and N-methyl morpholine, (4) dimethyltetramethylene sulphone and diethylanaline, (5) chloroform, triethylamine and triethylamine hydrochloride, (9), (10) and (11) methylene chloride and triethylamine, (12) dimethyltetramethylene sulphone and triethylamine, (13) tetramethylene sulphone and dimethylacetamide, (14), (16) and (17) dimethyl acetamide, (15) N-methyl-a -pyrrolidone, (18) N, N, N1, N1-tetramethyl urea, (19) hexamethyl phosphoramide, (20) N-acetyl pyrrolidone, (21) N, N-tetramethylene-N1, N1-dimethyl urea, (23) triethylamine and N-methyl pyrrolidone, (24) triethylamine and dimethyl cyanamide and (25) triethylamine, triethylamine hydrochloride and acetonitrile. The products are soluble in dimethyl formamide or dimethyl acetamide and may be extruded into filaments or formed into films. Specification 871,581 and U.S.A. Specification 2,831,834 are referred to.
GB6633/58A 1957-02-28 1958-02-28 Improvements in or relating to the production of polyamides Expired GB871578A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US64292857A 1957-02-28 1957-02-28
US713304A US3063966A (en) 1958-02-05 1958-02-05 Process of making wholly aromatic polyamides

Publications (1)

Publication Number Publication Date
GB871578A true GB871578A (en) 1961-06-28

Family

ID=27094145

Family Applications (2)

Application Number Title Priority Date Filing Date
GB6636/58A Expired GB871581A (en) 1957-02-28 1958-02-28 Polyamide structures and process for their production
GB6633/58A Expired GB871578A (en) 1957-02-28 1958-02-28 Improvements in or relating to the production of polyamides

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB6636/58A Expired GB871581A (en) 1957-02-28 1958-02-28 Polyamide structures and process for their production

Country Status (6)

Country Link
BE (1) BE565266A (en)
CH (2) CH426262A (en)
DE (2) DE1420681B2 (en)
FR (2) FR1199459A (en)
GB (2) GB871581A (en)
NL (1) NL108288C (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1929713A1 (en) * 1968-06-12 1970-02-12 Du Pont Anisotropic spinning solutions of aromatic polyamides
DE1795541A1 (en) * 1966-06-13 1972-02-10 Du Pont Polyamides, mixed polyamides and methods of making the same
JPS5012485B1 (en) * 1967-12-27 1975-05-12
FR2320963A1 (en) * 1975-08-15 1977-03-11 Hitachi Ltd POLYMERIZATION PROCESS FOR PREPARING AROMATIC POLYAMIDES CONTAINING ETHER GROUPS

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3049518A (en) * 1960-03-31 1962-08-14 Du Pont Polyamides from n, n'-bis (3-aminophenyl)-isophthalamide
DE1239430B (en) * 1963-09-18 1967-04-27 Hoechst Ag Process for the production of threads from beta-polyamides
USRE30352E (en) 1966-06-13 1980-07-29 E. I. Du Pont De Nemours And Company Optically anisotropic aromatic polyamide dopes
IL39187A (en) * 1971-04-28 1976-02-29 Du Pont Polyamide fibers and films and their preparation
DE2313308A1 (en) * 1973-03-17 1974-09-19 Hoechst Ag PROCESS FOR MANUFACTURING FABRICS, FIBERS AND FILMS FROM AROMATIC POLYAMIDES
US4162275A (en) * 1973-07-26 1979-07-24 E. I. Du Pont De Nemours And Company Flame-resistant fiber
US4118374A (en) 1974-09-09 1978-10-03 Sumitomo Chemical Company, Limited Production of aromatic polyamides from dicarboxylic acid and diamine
AU500143B2 (en) * 1974-12-27 1979-05-10 Teijin Ltd Fiber or film-forming copolyamide
NL157327C (en) * 1975-02-21 1984-05-16 Akzo Nv PROCESS FOR PREPARING POLY-P-PHENYLENE DEPHALAMIDE.
JPS5569649A (en) * 1978-11-21 1980-05-26 Teijin Ltd Aromatic polyamide composition
KR950014523B1 (en) * 1991-04-29 1995-12-05 주식회사 코오롱 Aromatic polyamide pulp and preparation method thereof
EP0567987A1 (en) * 1992-04-30 1993-11-03 Hoechst Aktiengesellschaft Process for the production of meta-aramide fibers
EP0567998A1 (en) * 1992-04-30 1993-11-03 Hoechst Aktiengesellschaft Process for the preparation of spinnable meta-aramides

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB737184A (en) * 1951-08-29 1955-09-21 Celanese Corp Production of polyamides

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1795541A1 (en) * 1966-06-13 1972-02-10 Du Pont Polyamides, mixed polyamides and methods of making the same
JPS5012485B1 (en) * 1967-12-27 1975-05-12
DE1929713A1 (en) * 1968-06-12 1970-02-12 Du Pont Anisotropic spinning solutions of aromatic polyamides
DE1929694A1 (en) * 1968-06-12 1970-09-03 Du Pont Mass and items made from it
DE1929694B2 (en) 1968-06-12 1976-04-22 E.I. du Pont de Nemours 'and Co., Wilmington, Del. (V.St.A.) OPTICALLY ANISOTROPIC MASSES OF AROMATIC POLYAMIDES
FR2320963A1 (en) * 1975-08-15 1977-03-11 Hitachi Ltd POLYMERIZATION PROCESS FOR PREPARING AROMATIC POLYAMIDES CONTAINING ETHER GROUPS
US4278786A (en) * 1975-08-15 1981-07-14 Hitachi, Ltd. Aromatic polyamides containing ether linkages and process for producing same

Also Published As

Publication number Publication date
CH426262A (en) 1966-12-15
NL108288C (en)
GB871581A (en) 1961-06-28
BE565266A (en) 1958-08-28
CH438572A (en) 1967-06-30
DE1420681B2 (en) 1971-09-30
DE1282843B (en) 1968-11-14
DE1420681A1 (en) 1968-10-10
FR1199459A (en) 1959-12-14
FR1199458A (en) 1959-12-14

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