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Aromatic polyamides containing ether linkages and process for producing same

Assignee: Hitachi Ltd
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Filing: 1979-07-05
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Granted: 1981-07-14
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Expires: 1999-07-05
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Abstract

Abstract A heat-resistant polyamide polymer having melt-moldability is obtained by reacting an aromatic diamine having the general formula: <IMAGE> R1-R4:H, Cl, CH3 R5-R6:H, CH3, CH5, C3H7 with an equivalent amount of aromatic dicarboxylic acid dihalide in an organic solvent in the presence of an aqueous solution of an alkali-metal hydroxide. When an equimolar mixture of terephthalic acid dihalide and isophthalic dihalide is reacted with the diamine, polyamide polymers with good melt-moldability are obtained.

Inventors

  • 👤 Ken Nanaumi
  • 👤 Fusaji Shoji
  • 👤 Hisashi Kohkame
  • 👤 Susumu Era

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-04 19:54
CPC Classifications
C; C08; C08G; C08G69/00; C08G69/02; C08G69/26; C08G69/32

Claims Analysis

Total Claims: 17
Claim 1
Independent Claim 208 words
An aromatic polyamide polymer produced by polymerization of an aromatic diamine having the general formula: ##STR3## wherein R 1 through R 4 are the same or different, and are members selected from the group consisting of H, Cl and CH 3 , and wherein R 5 and R 6 are the same or different, and are the members selected from the group consisting of H, CH 3 , C 2 H 5 and C 3 H 7 , the total carbon number of R 5 and R 6 being no greater than 4; with an equivalent amount of a mixture of terephthalic acid dichloride and isophthalic acid dichloride in molar proportions of from 80:20 to 20:80, said polymer having a reduced viscosity of 0.3 to 1.5 dl/g, and initial weight loss temperature of 380° C. or above, and an initial flow temperature of at least 80° C. lower than the initial weight loss temperature, whereby said aromatic polyamide polymer has melt moldability, in which said polymer is obtained by reacting said diamine and said mixture in a water-immiscible, chemically inert, organic solvent in the presence of an aqueous solution of an alkali-metal hydroxide or carbonate in an amount sufficient to neutralize an acidic substance generated in the reaction.
Claim 2
Dependent Claim 208 words
An aromatic polyamide polymer produced by polymerization of an aromatic diamine having the general formula: ##STR3## wherein R 1 through R 4 are the same or different, and are members selected from the group consisting of H, Cl and CH 3 , and wherein R 5 and R 6 are the same or different, and are the members selected from the group consisting of H, CH 3 , C 2 H 5 and C 3 H 7 , the total carbon number of R 5 and R 6 being no greater than 4; with an equivalent amount of a mixture of terephthalic acid dichloride and isophthalic acid dichloride in molar proportions of from 80:20 to 20:80, said polymer having a reduced viscosity of 0.3 to 1.5 dl/g, and initial weight loss temperature of 380° C. or above, and an initial flow temperature of at least 80° C. lower than the initial weight loss temperature, whereby said aromatic polyamide polymer has melt moldability, in which said polymer is obtained by reacting said diamine and said mixture in a water-immiscible, chemically inert, organic solvent in the presence of an aqueous solution of an alkali-metal hydroxide or carbonate in an amount sufficient to neutralize an acidic substance generated in the reaction.
Claim 3
Dependent Claim 31 words
An aromatic polyamide according to claim 1, wherein said diamine is at least one member selected from the group consisting of 4,4'-di(p-aminophenoxy)diphenylmethane; 4,4'-di(p-aminophenoxy)-3,3'-dichlorodiphenylmethane; 4,4'-di(p-aminophenoxy)-3,3'-dimethyldiphenylmethane; 4,4'-di(p-aminophenoxy)-3,3',5,5'-tetramethyldiphenylmethane; 4,4'-di(p-aminophenoxy)-diphenylpropane-(2,2); 4,4'-di(p-aminophenoxy)-3,3'-dichlorodiphenylpropane-(2,2); 4,4'-di(p-aminophenoxy)-3,3'-dimethyldiphenylpropane-(2,2); 4,4'-di(p-aminophenoxy)-3,3'-dimethyldiphenylpropane-(2,2); and 4,4'-di(p-aminophenoxy)-3,3'-dichlorodiphenylpentane-(3,3).
Claim 4
Dependent Claim 23 words
An aromatic polyamide polymer according to claim 1, wherein the mixture is an equimolar mixture of terephthalic acid dichloride and isophthalic acid dichloride.
Claim 5
Dependent Claim 13 words
An aromatic polyamide polymer according to claim 2, wherein said diamine is 4,4'-di(p-aminophenoxy)diphenylpropane-(2,2).
Claim 6
Dependent Claim 242 words
A process for preparing an aromatic polymer which comprises: reacting an aromatic diamine having the general formula: ##STR4## wherein R 1 through R 4 are the same or different, and are members selected from the group consisting of H, Cl and CH 3 , and R 5 and R 6 are the same or different, and are members selected from the group consisting of H, CH 3 , C 2 H 5 , C 3 H 7 , the total carbon number of R 5 and R 6 being no greater than 4, with a mixture of terephthalic acid dichloride and isophthalic acid dichloride in molar proportions of from 80:20 to 20:80 dissolved in a water-immiscible organic solvent which is chemically inert to said diamine and mixture as well as to the polyamide polymer and is capable of dissolving said diamine and mixture in the presence of an aqueous solution of an alkali-metal hydroxide or carbonate in an amount sufficient to neutralize an acidic substance generated in the reaction, under agitation at a temperature of 40° C. or below for a time sufficient to provide the polyamide polymer with a reduced viscosity of 0.3 to 1.5 dl/g, an initial weight loss temperature of 380° C. or above, and an initial flow temperature of at least 100° C. lower than the initial weight loss temperature; and recovering the resulting polyamide polymer from the reaction system, whereby said polyamide polymer has a melt moldability.
Claim 7
Dependent Claim 242 words
A process for preparing an aromatic polymer which comprises: reacting an aromatic diamine having the general formula: ##STR4## wherein R 1 through R 4 are the same or different, and are members selected from the group consisting of H, Cl and CH 3 , and R 5 and R 6 are the same or different, and are members selected from the group consisting of H, CH 3 , C 2 H 5 , C 3 H 7 , the total carbon number of R 5 and R 6 being no greater than 4, with a mixture of terephthalic acid dichloride and isophthalic acid dichloride in molar proportions of from 80:20 to 20:80 dissolved in a water-immiscible organic solvent which is chemically inert to said diamine and mixture as well as to the polyamide polymer and is capable of dissolving said diamine and mixture in the presence of an aqueous solution of an alkali-metal hydroxide or carbonate in an amount sufficient to neutralize an acidic substance generated in the reaction, under agitation at a temperature of 40° C. or below for a time sufficient to provide the polyamide polymer with a reduced viscosity of 0.3 to 1.5 dl/g, an initial weight loss temperature of 380° C. or above, and an initial flow temperature of at least 100° C. lower than the initial weight loss temperature; and recovering the resulting polyamide polymer from the reaction system, whereby said polyamide polymer has a melt moldability.
Claim 8
Dependent Claim 37 words
A process for preparing an aromatic polyamide polymer according to claim 5, wherein said aromatic diamine is at least one member selected from the group consisting of 4,4'-di(p-aminophenoxy)-diphenylmethane, 4,4'-di(p-aminophenoxy)-3,3'-dichlorodiphenylmethane, 4,4'-di(p-aminophenoxy)-3,3'-dimethyldiphenylmethane, 4,4'-di(p-aminophenoxy)-3,3',5,5'-tetramethyldiphenylmethane, 4,4'-di(p-aminophenoxy) diphenylpropane-(2,2),4,4'-di(p-aminophenoxy)-3,3'-dichlorodiphenylpropane-(2,2),4,4'-di(p-aminophenoxy)-3,3'-dimethyldiphenylpropane-(2,2), 4,4'-di(p-aminophenoxy)-3,3', 5,5'-tetramethyldiphenylpropane-(2,2), and 4,4'-di(p-aminophenoxy)-3,3'-dichlorodiphenylpentane-(3,3).
Claim 9
Dependent Claim 27 words
A process for preparing an aromatic polyamide polymer according to claim 5, wherein the mixture is an equimolar mixture of terephthalic acid dichloride and isophthalic acid dichloride.
Claim 10
Dependent Claim 35 words
A process for preparing an aromatic polyamide polymer according to claim 5, wherein said solvent is a member selected from the group consisting of cyclohexanone, diisobutylketone, acetophenone, p-methylacetophenone, p-methoxyacetophenone, methylene dichloride, dichloroethane, chloroform and nitrobenzene.
Claim 11
Dependent Claim 43 words
A process for preparing an aromatic polyamide polymer according to claim 5, wherein up to 50% of said diamine is replaced by at least one member selected from the group consisting of p-phenylenediamine, m-phenylenediamine, 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenyl ether, 4,4'-diaminodiphenylsulfone, 4,4'-diaminodiphenyl sulfide, 4,4'-diaminodiphenylpropane-(2,2), and 1,5-diaminonaphthalene.
Claim 12
Dependent Claim 86 words
A melt-moldable aromatic polyamide polymer, which is a polycondensation product of an aromatic diamine selected from the group consisting of 4,4'-di(p-aminophenoxy)diphenylpropane-(2,2), 4,4'-di(p-aminophenoxy)-3,3',5,5'-tetramethyldiphenylmethane, 4,4'-di(p-aminophenoxy)-3,3'-dichlorodiphenylpropane-(2,2), and 4,4'-di(p-aminophenoxy)-3,3'-dimethyldiphenylpropane-(2,2), with an equivalent amount of a mixture of terephthalic acid dichloride and isophthalic acid dichloride in molar proportions of from 80:20 to 20:80, said polycondensation product having a reduced viscosity of 0.55 to 0.9, an initial weight loss temperature of 380° C. or above, and an initial flow temperature of at least 100° C. lower than the initial weight loss temperature.
Claim 13
Dependent Claim 86 words
A melt-moldable aromatic polyamide polymer, which is a polycondensation product of an aromatic diamine selected from the group consisting of 4,4'-di(p-aminophenoxy)diphenylpropane-(2,2), 4,4'-di(p-aminophenoxy)-3,3',5,5'-tetramethyldiphenylmethane, 4,4'-di(p-aminophenoxy)-3,3'-dichlorodiphenylpropane-(2,2), and 4,4'-di(p-aminophenoxy)-3,3'-dimethyldiphenylpropane-(2,2), with an equivalent amount of a mixture of terephthalic acid dichloride and isophthalic acid dichloride in molar proportions of from 80:20 to 20:80, said polycondensation product having a reduced viscosity of 0.55 to 0.9, an initial weight loss temperature of 380° C. or above, and an initial flow temperature of at least 100° C. lower than the initial weight loss temperature.
Claim 14
Dependent Claim 31 words
A melt-moldable aromatic polyamide polymer according to claim 10, wherein up to 50% of said diamine is replaced by a member selected from the group consisting of m-phenylene diamine and 4,4'-diaminodiphenylether.
Claim 15
Dependent Claim 24 words
A melt-moldable polyamide polymer according to claim 10, wherein the mixture of said terephthalic acid dichloride and isophthalic acid dichloride is an equimolar mixture.
Claim 16
Dependent Claim 13 words
A melt-molded article consisting of the polyamide polymer as defined in claim 11.
Claim 17
Dependent Claim 13 words
A melt-molded article consisting of the polyamide polymer as defined in claim 12.

References Cited (Backward Citations)

GB871578A Cited
CH389243A Cited
CH435732A Cited
US3354125A Cited
US3505288A Cited
US3503931A Cited
US3663517A Cited
DE2007796A1 Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-07-13 1985-01-12 1985-07-14 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-07-13 1989-01-12 1989-07-14 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-07-13 1993-01-12 1993-07-14 $7700.00 Window Closed / Lapsed

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