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US4118374A Expired / Lapsed US ⏱️ 0.0 years remaining

Production of aromatic polyamides from dicarboxylic acid and diamine

Assignee: Sumitomo Chemical Co Ltd
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Filing: 1977-05-27
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Granted: 1978-10-03
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Expires: 1997-05-27
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Abstract

Abstract Aromatic polyamides having high polymerization degree are produced by polycondensing an arylene containing aminocarboxylic acid, or a dicarboxylic acid with an aromatic diamine in the presence of a phosphorus compound, a tertiary amine and a metal halide using N-methylpyrrolidone and/or dimethylacetamide as a solvent.

Inventors

  • 👤 Noboru Yamazaki
  • 👤 Fukuji Higashi

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-31 14:29
CPC Classifications
C; C08; C08G; C08G69/00; C08G69/02; C08G69/26; C08G69/32; C08G69/08; C08G69/12

Claims Analysis

Total Claims: 7
Claim 1
Independent Claim 503 words
In a process for producing a fiber forming aromatic polyamide by polycondensing a dicarboxylic acid of the formula, HOOC -- R.sup.2 -- COOH (II) wherein R 2 is a straight chain, branched chain or alicylic hydrocarbon radical, an aryl group with or without at least one substituent selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a phenyl group, a halogen atom, a nitro group and a cyano group, or a radical in which two or more radicals selected from the group consisting of the above-mentioned radicals are bonded through an alkylene group having 1 to 4 carbon atoms, an alkylidene group having 2 to 4 carbon atoms, --CONH-- or --SO 2 NH--, with an aromatic diamine of the formula, H.sub.2 N -- R.sup.3 -- NH.sub.2 (III) wherein R 3 is an aromatic hydrocarbon radical which may contain one or more substituents on the aromatic nuclei, said substituent being an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a phenyl group, a halogen atom, a nitro group or a cyano group, and which may contain two or more aromatic hydrocarbon radicals bonded through an alkylene group having 1 to 4 carbon atoms, an alkylidene group having 2 to 4 carbon atoms, --O--, --SO 2 --, --S--, --NH--, --NR"-- wherein R" is an alkyl group having 1 to 4 carbon atoms, --CONH--, --CO-- or --SO 2 NH--, in the presence of a phosphorus compound of the formula, R.sup.4 -- P (OR.sup.5).sub.2 (IV) wherein R 4 is OR 5 , a hydroxyl group, an alkyl group having 1 to 6 carbon atoms or an aryl group with or without at least one substituent selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a phenyl group, a halogen atom, a nitro group and a cyano group; and R 5 is an aryl group with or without at least one substituent selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a phenyl group, a halogen atom, a nitro group and a cyano group, and a teriary amine in the liquid phase, wherein the tertiary amine is used in an amount of 1 mole or more per mole of the phosphorus compound and the phosphorus compound is used in an amount of 2 moles or more per mole of the dicarboxylic acid or diamine, the improvement which comprises carrying out the polycondensation using a solvent selected from the group consisting of N-methylpyrrolidone and dimethylacetamide as the reaction medium and a metal halide selected from the group consisting of a lithium halide and a calcium halide wherein the metal halide is used in an amount of 1 to 15% by weight based on the weight of the mixture of the tertiary amine and the solvent.
Claim 2
Dependent Claim 503 words
In a process for producing a fiber forming aromatic polyamide by polycondensing a dicarboxylic acid of the formula, HOOC -- R.sup.2 -- COOH (II) wherein R 2 is a straight chain, branched chain or alicylic hydrocarbon radical, an aryl group with or without at least one substituent selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a phenyl group, a halogen atom, a nitro group and a cyano group, or a radical in which two or more radicals selected from the group consisting of the above-mentioned radicals are bonded through an alkylene group having 1 to 4 carbon atoms, an alkylidene group having 2 to 4 carbon atoms, --CONH-- or --SO 2 NH--, with an aromatic diamine of the formula, H.sub.2 N -- R.sup.3 -- NH.sub.2 (III) wherein R 3 is an aromatic hydrocarbon radical which may contain one or more substituents on the aromatic nuclei, said substituent being an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a phenyl group, a halogen atom, a nitro group or a cyano group, and which may contain two or more aromatic hydrocarbon radicals bonded through an alkylene group having 1 to 4 carbon atoms, an alkylidene group having 2 to 4 carbon atoms, --O--, --SO 2 --, --S--, --NH--, --NR"-- wherein R" is an alkyl group having 1 to 4 carbon atoms, --CONH--, --CO-- or --SO 2 NH--, in the presence of a phosphorus compound of the formula, R.sup.4 -- P (OR.sup.5).sub.2 (IV) wherein R 4 is OR 5 , a hydroxyl group, an alkyl group having 1 to 6 carbon atoms or an aryl group with or without at least one substituent selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a phenyl group, a halogen atom, a nitro group and a cyano group; and R 5 is an aryl group with or without at least one substituent selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a phenyl group, a halogen atom, a nitro group and a cyano group, and a teriary amine in the liquid phase, wherein the tertiary amine is used in an amount of 1 mole or more per mole of the phosphorus compound and the phosphorus compound is used in an amount of 2 moles or more per mole of the dicarboxylic acid or diamine, the improvement which comprises carrying out the polycondensation using a solvent selected from the group consisting of N-methylpyrrolidone and dimethylacetamide as the reaction medium and a metal halide selected from the group consisting of a lithium halide and a calcium halide wherein the metal halide is used in an amount of 1 to 15% by weight based on the weight of the mixture of the tertiary amine and the solvent.
Claim 3
Dependent Claim 38 words
A process according to claim 1, wherein the dicarboxylic acid is glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, brassylic acid, thapsic acid, α-methylglutaric acid, α-methyladipic acid, 1,4-cyclohexanedicarboxylic acid, terephthalic acid or isophthalic acid.
Claim 4
Dependent Claim 19 words
A process according to claim 1, wherein the aromatic diamine is p-phenylenediamine, m-xylylenediamine, p-xylylenediamine, bis-(4-aminophenyl)-methane, di-(4-aminophenyl) ether or 2,2-bis-[4-(4-aminophenoxy)phenyl]-propane.
Claim 5
Dependent Claim 16 words
A process according to claim 1, wherein the aromatic diamine is p-phenylenediamine, bis-(4-aminophenyl)-methane or bis-(4-aminophenyl) ether.
Claim 6
Dependent Claim 40 words
A process according to claim 1, wherein the solvent is used in a condition that a concentration of the starting dicarboxylic acid and aromatic diamine, is in a range of from 0.2 to 2.0 moles per liter of the solvent.
Claim 7
Dependent Claim 30 words
A process according to claim 1, wherein the metal halide is used in 1-15% by weight based on the weight of a mixture of the tertiary amine and the solvent.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-10-02 1982-04-03 1982-10-03 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-10-02 1986-04-03 1986-10-03 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-10-02 1990-04-03 1990-10-03 $7700.00 Window Closed / Lapsed

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