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US4339375A Expired / Lapsed US ⏱️ 0.0 years remaining

Poly(ester-amide) capable of forming an anisotropic melt phase derived from p-hydroxybenzoic acid, 2,6-dihydroxynaphthalene, carbocyclic dicarboxylic acid, aromatic monomer capable of forming an amide linkage, and, optionally, additional aromatic diol

Assignee: Celanese Corp
•
Filing: 1981-06-04
•
Granted: 1982-07-13
•
Expires: 2001-06-04
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Abstract

Abstract A melt processable poly(ester-amide) which is capable of forming an anisotropic melt phase is provided. The poly(ester-amide) of the present invention consists essentially of the recurring units (a) p-oxybenzoyl moiety, (b) 2,6-dioxynaphthylene moiety, (c) carbocyclic dicarboxyl moiety, (d) aromatic moiety capable of forming an amide linkage in the polymer, and optionally, (e) p-dioxyaryl moiety, in the proportions indicated. Preferably, the aromatic moiety capable of forming an amide linkage is derived from p-aminophenol or p-phenylenediamine. The resulting poly(ester-amide) exhibits a melting temperature below approximately 400° C., preferably below approximately 350° C. The poly(ester-amide) of the present invention is preferably formed by a melt polymerization technique.

Inventors

  • 👤 Gordon W. Calundann
  • 👤 Larry F. Charbonneau
  • 👤 Anthony J. East

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-26 18:27
CPC Classifications
C; C08; C08G; C08G69/00; C08G69/44

Claims Analysis

Total Claims: 47
Claim 1
Independent Claim 264 words
A melt processable poly(ester-amide) capable of forming an anisotropic melt phase at a temperature below approximately 400° C. consisting essentially of recurring moieties I, II, III, IV, and, optionally, V wherein: I is ##STR10## II is ##STR11## III is ##STR12## where A is a divalent carbocyclic radical; IV is --Y--Ar--Z--, where Ar is a divalent radical comprising at least one aromatic ring, Y is O, NH, or NR, and Z is NH or NR, where R is an alkyl group of 1 to 6 carbon atoms or an aryl group; and V is --O--Ar'--O--, where Ar' is a divalent radical comprising at least one aromatic ring, other than naphthylene, wherein at least some of the hydrogen atoms present upon the rings optionally may be replaced by substitution selected from the group consisting of alkyl group of 1 to 4 carbon atoms, an alkoxy group of 1 to 4 carbon atoms, halogen, phenyl, and mixtures thereof, and wherein moiety I is present in a concentration within the range of approximately 20 to 80 mole percent, moiety II is present in a concentration within the range of approximately 5 to 30 mole percent, moiety III is present in a concentration within the range of approximately 10 to 40 mole percent, moiety IV is present in a concentration within the range of approximately 5 to 30 mole percent, and moiety V is present in a concentration within the range of approximately 0 to 20 mole percent, with the total molar concentration of moieties II, IV, and V being substantially equal to the molar concentration of moiety III.
Claim 2
Dependent Claim 264 words
A melt processable poly(ester-amide) capable of forming an anisotropic melt phase at a temperature below approximately 400° C. consisting essentially of recurring moieties I, II, III, IV, and, optionally, V wherein: I is ##STR10## II is ##STR11## III is ##STR12## where A is a divalent carbocyclic radical; IV is --Y--Ar--Z--, where Ar is a divalent radical comprising at least one aromatic ring, Y is O, NH, or NR, and Z is NH or NR, where R is an alkyl group of 1 to 6 carbon atoms or an aryl group; and V is --O--Ar'--O--, where Ar' is a divalent radical comprising at least one aromatic ring, other than naphthylene, wherein at least some of the hydrogen atoms present upon the rings optionally may be replaced by substitution selected from the group consisting of alkyl group of 1 to 4 carbon atoms, an alkoxy group of 1 to 4 carbon atoms, halogen, phenyl, and mixtures thereof, and wherein moiety I is present in a concentration within the range of approximately 20 to 80 mole percent, moiety II is present in a concentration within the range of approximately 5 to 30 mole percent, moiety III is present in a concentration within the range of approximately 10 to 40 mole percent, moiety IV is present in a concentration within the range of approximately 5 to 30 mole percent, and moiety V is present in a concentration within the range of approximately 0 to 20 mole percent, with the total molar concentration of moieties II, IV, and V being substantially equal to the molar concentration of moiety III.
Claim 3
Dependent Claim 23 words
The melt processable poly(ester-amide) of claim 1 which is capable of forming an anisotropic melt phase at a temperature below approximately 350° C.
Claim 4
Dependent Claim 32 words
The melt processable poly(ester-amide) of claim 1 which exhibits an inherent viscosity of at least approximately 1.0 dl./g. when measured at a concentration of 0.1 weight/volume percent in pentafluorophenol at 60° C.
Claim 5
Dependent Claim 32 words
The melt processable poly(ester-amide) of claim 3 which exhibits an inherent viscosity of at least approximately 2.0 dl./g. when measured at a concentration of 0.1 weight/volume percent in pentafluorophenol at 60° C.
Claim 6
Dependent Claim 45 words
The melt processable poly(ester-amide) of claim 1 wherein the total molar concentration of moieties II, IV, and V and the molar concentration of moiety III each is substantially equal to one-half of the difference between 100 mole percent and the molar concentration of moiety I.
Claim 7
Dependent Claim 25 words
The melt processable poly(ester-amide) of claim 1 wherein moiety I is present in a concentration within the range of approximately 40 to 60 mole percent.
Claim 8
Dependent Claim 25 words
The melt processable poly(ester-amide) of claim 1 wherein moiety II is present in a concentration within the range of approximately 10 to 25 mole percent.
Claim 9
Dependent Claim 25 words
The melt processable poly(ester-amide) of claim 1 wherein moiety III is present in a concentration within the range of approximately 15 to 30 mole percent.
Claim 10
Dependent Claim 25 words
The melt processable poly(ester-amide) of claim 1 wherein moiety IV is present in a concentration within the range of approximately 5 to 15 mole percent.
Claim 11
Dependent Claim 25 words
The melt processable poly(ester-amide) of claim 10 wherein moiety V is present in a concentration within the range of approximately 0 to 10 mole percent.
Claim 12
Dependent Claim 25 words
The melt processable poly(ester-amide) of claim 10 wherein moiety V is present in a concentration within the range of approximately 5 to 10 mole percent.
Claim 13
Dependent Claim 25 words
The melt processable poly(ester-amide) of claim 1 wherein the divalent carbocyclic radical of moiety III comprises at least one aromatic ring or a trans-1,4-cyclohexylene radical.
Claim 14
Dependent Claim 21 words
The melt processable poly(ester-amide) of claim 12 wherein the divalent carbocyclic radical of moiety III comprises at least one aromatic ring.
Claim 15
Dependent Claim 27 words
A molding compound comprising the melt processable poly(ester-amide) of claim 1 which incorporates approximately 1 to 60 percent by weight of a solid filler and/or reinforcing agent.
Claim 16
Dependent Claim 11 words
A molded article comprising the melt processable poly(ester-amide) of claim 1.
Claim 17
Dependent Claim 15 words
A fiber which has been melt spun from the melt processable poly(ester-amide) of claim 1.
Claim 18
Dependent Claim 15 words
A film which has been melt extruded from the melt processable poly(ester-amide) of claim 1.
Claim 19
Dependent Claim 266 words
A melt processable poly(ester-amide) capable of forming an anisotropic melt phase at a temperature below approximately 400° C. consisting essentially of recurring moieties I, II, III, IV, and, optionally V wherein: I is ##STR13## II is ##STR14## III is ##STR15## where A is a divalent carbocyclic radical; IV is --Y--Ar--Z--, where Ar is a divalent radical comprising at least one aromatic ring, Y is O, NH, or NR, and Z is NH or NR, where R is an alkyl group of 1 to 6 carbon atoms or an aryl group; and V is --O--Ar'--O--, where Ar' is a divalent radical comprising at least one aromatic ring, other than naphthylene, wherein at least some of the hydrogen atoms present upon the aromatic rings optionally may be replaced by substitution selected from the group consisting of an alkyl group of 1 to 4 carbon atoms, an alkoxy group of 1 to 4 carbon atoms, halogen, phenyl, and mixtures thereof, and wherein moiety I is present in a concentration within the range of approximately 40 to 60 mole percent, moiety II is present in a concentration within the range of approximately 10 to 25 mole percent, moiety III is present in a concentration within the range of approximately 15 to 30 mole percent, moiety IV is present in a concentration within the range of approximately 5 to 15 mole percent, and moiety V is present in a concentration within the range of approximately 0 to 10 mole percent, with the total molar concentration of moieties II, IV, and V being substantially equal to the molar concentration of moiety III.
Claim 20
Dependent Claim 266 words
A melt processable poly(ester-amide) capable of forming an anisotropic melt phase at a temperature below approximately 400° C. consisting essentially of recurring moieties I, II, III, IV, and, optionally V wherein: I is ##STR13## II is ##STR14## III is ##STR15## where A is a divalent carbocyclic radical; IV is --Y--Ar--Z--, where Ar is a divalent radical comprising at least one aromatic ring, Y is O, NH, or NR, and Z is NH or NR, where R is an alkyl group of 1 to 6 carbon atoms or an aryl group; and V is --O--Ar'--O--, where Ar' is a divalent radical comprising at least one aromatic ring, other than naphthylene, wherein at least some of the hydrogen atoms present upon the aromatic rings optionally may be replaced by substitution selected from the group consisting of an alkyl group of 1 to 4 carbon atoms, an alkoxy group of 1 to 4 carbon atoms, halogen, phenyl, and mixtures thereof, and wherein moiety I is present in a concentration within the range of approximately 40 to 60 mole percent, moiety II is present in a concentration within the range of approximately 10 to 25 mole percent, moiety III is present in a concentration within the range of approximately 15 to 30 mole percent, moiety IV is present in a concentration within the range of approximately 5 to 15 mole percent, and moiety V is present in a concentration within the range of approximately 0 to 10 mole percent, with the total molar concentration of moieties II, IV, and V being substantially equal to the molar concentration of moiety III.
Claim 21
Dependent Claim 23 words
The melt processable poly(ester-amide) of claim 18 which is capable of forming an anisotropic melt phase at a temperature below approximately 350° C.
Claim 22
Dependent Claim 32 words
The melt processable poly(ester-amide) of claim 18 which exhibits an inherent viscosity of at least approximately 1.0 dl./g. when measured at a concentration of 0.1 weight/volume percent in pentafluorophenol at 60° C.
Claim 23
Dependent Claim 35 words
The melt processable poly(ester-amide) of claim 20 which exhibits an inherent viscosity within the range of approximately 3.0 to 8.0 dl./g. when measured at a concentration of 0.1 weight/volume percent of pentafluorophenol at 60° C.
Claim 24
Dependent Claim 45 words
The melt processable poly(ester-amide) of claim 18 wherein the total molar concentration of moieties II, IV, and V and the molar concentration of moiety III each is substantially equal to one-half of the difference between 100 mole percent and the molar concentration of moiety I.
Claim 25
Dependent Claim 25 words
The melt processable poly(ester-amide) of claim 18 wherein moiety I is present in a concentration within the range of approximately 50 to 60 mole percent.
Claim 26
Dependent Claim 25 words
The melt processable poly(ester-amide) of claim 18 wherein moiety II is present in a concentration within the range of approximately 15 to 25 mole percent.
Claim 27
Dependent Claim 25 words
The melt processable poly(ester-amide) of claim 18 wherein moiety III is present in a concentration within the range of approximately 20 to 30 mole percent.
Claim 28
Dependent Claim 25 words
The melt processable poly(ester-amide) of claim 18 wherein moiety IV is present in a concentration within the range of approximately 5 to 10 mole percent.
Claim 29
Dependent Claim 25 words
The melt processable poly(ester-amide) of claim 18 wherein moiety V is present in a concentration within the range of approximately 5 to 10 mole percent.
Claim 30
Dependent Claim 25 words
The melt processable poly(ester-amide) of claim 18 wherein the divalent carbocyclic radical of moiety III comprises at least one aromatic ring or a trans-1,4-cyclohexylene radical.
Claim 31
Dependent Claim 21 words
The melt processable poly(ester-amide) of claim 18 wherein the divalent carbocyclic radical of moiety III comprises at least one aromatic ring.
Claim 32
Dependent Claim 27 words
A molding compound comprising the melt processable poly(ester-amide) of claim 18 which incorporates approximately 1 to 60 percent by weight of a solid filler and/or reinforcing agent.
Claim 33
Dependent Claim 11 words
A molded article comprising the melt processable poly(ester-amide) of claim 18.
Claim 34
Dependent Claim 15 words
A fiber which has been melt spun from the melt processable poly(ester-amide) of claim 18.
Claim 35
Dependent Claim 15 words
A film which has been melt extruded from the melt processable poly(ester-amide) of claim 18.
Claim 36
Dependent Claim 275 words
A melt processable poly(ester-amide) capable of forming an anisotropic melt phase at a temperature below approximately 400° C. consisting essentially of recurring moieties I, II, III, IV, and, optionally, V wherein: I is ##STR16## II is ##STR17## III is ##STR18## where A is a divalent radical comprising at least one aromatic ring or a trans-1,4-cyclohexylene radical; IV is --Y--Ar--Z--, where Ar is a divalent radical comprising at least one aromatic ring, Y is O, NH, or NR, and Z is NH or NR, where R is an alkyl group of 1 to 6 carbon atoms or an aryl group; and V is --O--Ar'--O--, where Ar' is a divalent radical comprising at least one aromatic ring, other than naphthylene, wherein at least some of the hydrogen atoms present upon the aromatic rings optionally may be replaced by substitution selected from the group consisting of an alkyl group of 1 to 4 carbon atoms, an alkoxy group of 1 to 4 carbon atoms, halogen, phenyl, and mixtures thereof, and wherein moiety I is present in a concentration within the range of approximately 50 to 60 mole percent, moiety II is present in a concentration within the range of approximately 15 to 25 mole percent, moiety III is present in a concentration within the range of approximately 20 to 30 mole percent, moiety IV is present in a concentration within the range of approximately 5 to 10 mole percent, and moiety V is present in a concentration within the range of approximately 0 to 10 mole percent, with the total molar concentration of moieties II, IV, and V being substantially equal to the molar concentration of moiety III.
Claim 37
Dependent Claim 275 words
A melt processable poly(ester-amide) capable of forming an anisotropic melt phase at a temperature below approximately 400° C. consisting essentially of recurring moieties I, II, III, IV, and, optionally, V wherein: I is ##STR16## II is ##STR17## III is ##STR18## where A is a divalent radical comprising at least one aromatic ring or a trans-1,4-cyclohexylene radical; IV is --Y--Ar--Z--, where Ar is a divalent radical comprising at least one aromatic ring, Y is O, NH, or NR, and Z is NH or NR, where R is an alkyl group of 1 to 6 carbon atoms or an aryl group; and V is --O--Ar'--O--, where Ar' is a divalent radical comprising at least one aromatic ring, other than naphthylene, wherein at least some of the hydrogen atoms present upon the aromatic rings optionally may be replaced by substitution selected from the group consisting of an alkyl group of 1 to 4 carbon atoms, an alkoxy group of 1 to 4 carbon atoms, halogen, phenyl, and mixtures thereof, and wherein moiety I is present in a concentration within the range of approximately 50 to 60 mole percent, moiety II is present in a concentration within the range of approximately 15 to 25 mole percent, moiety III is present in a concentration within the range of approximately 20 to 30 mole percent, moiety IV is present in a concentration within the range of approximately 5 to 10 mole percent, and moiety V is present in a concentration within the range of approximately 0 to 10 mole percent, with the total molar concentration of moieties II, IV, and V being substantially equal to the molar concentration of moiety III.
Claim 38
Dependent Claim 32 words
The melt processable poly(ester-amide) of claim 34 which exhibits an inherent viscosity of at least approximately 1.0 dl./g. when measured at a concentration of 0.1 weight/volume percent in pentafluorophenol at 60° C.
Claim 39
Dependent Claim 35 words
The melt processable poly(ester-amide) of claim 35 which exhibits an inherent viscosity within the range of approximately 3.0 to 8.0 dl./g. when measured at a concentration of 0.1 weight/volume percent in pentafluorophenol at 60° C.
Claim 40
Dependent Claim 25 words
The melt processable poly(ester-amide) of claim 34 wherein moiety V is present in a concentration within the range of approximately 5 to 10 mole percent.
Claim 41
Dependent Claim 21 words
The melt processable (poly(ester-amide) of claim 34 wherein the divalent carbocyclic radical of moiety III comprises at least one aromatic ring.
Claim 42
Dependent Claim 16 words
The melt processable poly(ester-amide) of claim 34 wherein moiety IV is derived from p-aminophenol or p-phenylenediamine.
Claim 43
Dependent Claim 14 words
The melt processable poly(ester-amide) of claim 34 wherein moiety V is derived from hydroquinone.
Claim 44
Dependent Claim 27 words
A molding compound comprising the melt processable poly(ester-amide) of claim 34 which incorporates approximately 1 to 60 percent by weight of a solid filler and/or reinforcing agent.
Claim 45
Dependent Claim 11 words
A molded article comprising the melt processable poly(ester-amide) of claim 34.
Claim 46
Dependent Claim 15 words
A fiber which has been melt spun from the melt processable poly(ester-amide) of claim 34.
Claim 47
Dependent Claim 15 words
A film which has been melt extruded from the melt processable poly(ester-amide) of claim 34.

References Cited (Backward Citations)

US3859251A Cited
US4182842A Cited
US4272625A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1985-07-12 1986-01-11 1986-07-13 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1989-07-12 1990-01-11 1990-07-13 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1993-07-12 1994-01-11 1994-07-13 $7700.00 Window Closed / Lapsed

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