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US4351918A Expired / Lapsed US ⏱️ 0.0 years remaining

Poly(ester-amide) capable of forming an anisotropic melt phase derived from 6-hydroxy-2-naphthoic acid, other aromatic hydroxyacid, carbocyclic dicarboxylic acid, and aromatic monomer capable of forming an amide linkage

Assignee: Celanese Corp
•
Filing: 1981-04-06
•
Granted: 1982-09-28
•
Expires: 2001-04-06
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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) 6-oxy-2-naphthoyl moiety, (b) other aromatic moiety derived from aromatic hydroxyacid, (c) carbocyclic dicarboxyl moiety, (d) aromatic moiety capable of forming an amide linkage in the polymer, and, optionally, (e) dioxyaryl moiety in the proportions indicated. Preferably, the 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

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

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-23 21:57
CPC Classifications
C; C08; C08G; C08G69/00; C08G69/44

Claims Analysis

Total Claims: 42
Claim 1
Independent Claim 250 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 ##STR12## II is ##STR13## where Ar is a divalent radical comprising at least one aromatic ring other than 2,6-naphthylene; III is ##STR14## 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, wherein at least some of the hydrogen atoms present upon the 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 the total molar concentration of moiety I and moiety II in the polymer is within the range of approximately 10 to 90 mole percent, with the molar ratio of moiety I:moiety II being within the range of approximately 1:9 to 9:1, and the total molar concentration of moiety IV and moiety V is substantially equal to the molar concentration of moiety III, with moiety IV being present in a concentration within the range of approximately 5 to 45 mole percent.
Claim 2
Dependent Claim 250 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 ##STR12## II is ##STR13## where Ar is a divalent radical comprising at least one aromatic ring other than 2,6-naphthylene; III is ##STR14## 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, wherein at least some of the hydrogen atoms present upon the 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 the total molar concentration of moiety I and moiety II in the polymer is within the range of approximately 10 to 90 mole percent, with the molar ratio of moiety I:moiety II being within the range of approximately 1:9 to 9:1, and the total molar concentration of moiety IV and moiety V is substantially equal to the molar concentration of moiety III, with moiety IV being present in a concentration within the range of approximately 5 to 45 mole percent.
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 56 words
The melt processable poly(ester-amide) of claim 1 consisting essentially of approximately 1 to 80 mole percent of moiety I, approximately 1 to 80 mole percent of moiety II, approximately 5 to 45 mole percent of moiety III, approximately 5 to 45 mole percent of moiety IV, and approximately 0 to 25 mole percent of moiety V.
Claim 7
Dependent Claim 29 words
The melt processable poly(ester-amide) of claim 1 wherein the total molar concentration of moiety I and moiety II is within the range of approximately 20 to 80 mole percent.
Claim 8
Dependent Claim 24 words
The melt processable poly(ester-amide) of claim 1 wherein the molar ratio of moiety I:moiety II is within the range of approximately 1:3 to 3:1.
Claim 9
Dependent Claim 28 words
The melt processable poly(ester-amide) of claim 1 wherein said divalent carbocyclic radical of moiety III comprises at least one aromatic ring or at least one divalent trans-1,4-cyclohexylene radical.
Claim 10
Dependent Claim 25 words
The melt processable poly(ester-amide) of claim 5 wherein moiety V is present in a concentration within the range of approximately 5 to 25 mole percent.
Claim 11
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 12
Dependent Claim 11 words
A molded article comprising the melt processable poly(ester-amide) of claim 1.
Claim 13
Dependent Claim 15 words
A fiber which has been melt spun from the melt processable poly(ester-amide) of claim 1.
Claim 14
Dependent Claim 15 words
A film which has been melt extruded from the melt processable poly(ester-amide) of claim 1.
Claim 15
Dependent Claim 262 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 ##STR15## II is ##STR16## where Ar is a divalent radical comprising at least one aromatic ring other than 2,6-naphthylene; III is ##STR17## where A is a divalent radical comprising at least one aromatic ring or at least one divalent 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, wherein at least some of the hydrogen atoms present upon the 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 the total molar concentration of moiety I and moiety II in the polymer is within the range of approximately 20 to 80 mole percent, with the molar ratio of moiety I:moiety II being within the range of approximately 1:3 to 3:1, and the total molar concentration of moiety IV and moiety V is substantially equal to the molar concentration of moiety III, with moiety IV being present in a concentration within the range of approximately 5 to 40 mole percent.
Claim 16
Dependent Claim 262 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 ##STR15## II is ##STR16## where Ar is a divalent radical comprising at least one aromatic ring other than 2,6-naphthylene; III is ##STR17## where A is a divalent radical comprising at least one aromatic ring or at least one divalent 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, wherein at least some of the hydrogen atoms present upon the 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 the total molar concentration of moiety I and moiety II in the polymer is within the range of approximately 20 to 80 mole percent, with the molar ratio of moiety I:moiety II being within the range of approximately 1:3 to 3:1, and the total molar concentration of moiety IV and moiety V is substantially equal to the molar concentration of moiety III, with moiety IV being present in a concentration within the range of approximately 5 to 40 mole percent.
Claim 17
Dependent Claim 23 words
The melt processable poly(ester-amide) of claim 14 which is capable of forming an anisotropic melt phase at a temperature below approximately 350° C.
Claim 18
Dependent Claim 32 words
The melt processable poly(ester-amide) of claim 14 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 19
Dependent Claim 35 words
The melt processable poly(ester-amide) of claim 16 which exhibits an inherent viscosity within the range of approximately 3.0 to 9.0 dl./g. when measured at a concentration of 0.1 weight/volume percent in pentafluorophenol at 60° C.
Claim 20
Dependent Claim 56 words
The melt processable poly(ester-amide) of claim 14 consisting essentially of approximately 5 to 60 mole percent of moiety I, approximately 5 to 60 mole percent of moiety II, approximately 10 to 40 mole percent of moiety III, approximately 5 to 40 mole percent of moiety IV, and approximately 0 to 25 mole percent of moiety V.
Claim 21
Dependent Claim 29 words
The melt processable poly(ester-amide) of claim 14 wherein the total molar concentration of moiety I and moiety II is within the range of approximately 30 to 70 mole percent.
Claim 22
Dependent Claim 24 words
The melt processable poly(ester-amide) of claim 14 wherein the molar ratio of moiety I:moiety II is within the range of approximately 2:3 to 3:2.
Claim 23
Dependent Claim 20 words
The melt processable poly(ester-amide) of claim 14 wherein said divalent radical of moiety III comprises at least one aromatic ring.
Claim 24
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 25 mole percent.
Claim 25
Dependent Claim 27 words
A molding compound comprising the melt processable poly(ester-amide) of claim 14 which incorporates approximately 1 to 60 percent by weight of a solid filler and/or reinforcing agent.
Claim 26
Dependent Claim 11 words
A molded article comprising the melt processable poly(ester-amide) of claim 14.
Claim 27
Dependent Claim 15 words
A fiber which has been melt spun from the melt processable poly(ester-amide) of claim 14.
Claim 28
Dependent Claim 14 words
A film which has been extruded from the melt processable poly(ester-amide) of claim 14.
Claim 29
Dependent Claim 255 words
A melt processable poly(ester-amide) capable of forming an anisotropic melt phase at a temperature below approximately 350° C. consisting essentially of recurring moieties I, II, III, IV, and, optionally, V wherein: I is ##STR18## II is ##STR19## where Ar is a divalent radical comprising at least one aromatic ring other than 2,6-naphthylene; III is ##STR20## where A is a divalent radical comprising at least one aromatic ring; 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, wherein at least some of the hydrogen atoms present upon the 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 the total molar concentration of moiety I and moiety II in the polymer is within the range of approximately 30 to 70 mole percent, with the molar ratio of moiety I:moiety II being within the range of approximately 2:3 to 3:2, and the total molar concentration of moiety IV and moiety V is substantially equal to the molar concentration of moiety III, with moiety IV being present in a concentration within the range of approximately 5 to 35 mole percent.
Claim 30
Dependent Claim 255 words
A melt processable poly(ester-amide) capable of forming an anisotropic melt phase at a temperature below approximately 350° C. consisting essentially of recurring moieties I, II, III, IV, and, optionally, V wherein: I is ##STR18## II is ##STR19## where Ar is a divalent radical comprising at least one aromatic ring other than 2,6-naphthylene; III is ##STR20## where A is a divalent radical comprising at least one aromatic ring; 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, wherein at least some of the hydrogen atoms present upon the 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 the total molar concentration of moiety I and moiety II in the polymer is within the range of approximately 30 to 70 mole percent, with the molar ratio of moiety I:moiety II being within the range of approximately 2:3 to 3:2, and the total molar concentration of moiety IV and moiety V is substantially equal to the molar concentration of moiety III, with moiety IV being present in a concentration within the range of approximately 5 to 35 mole percent.
Claim 31
Dependent Claim 32 words
The melt processable poly(ester-amide) of claim 27 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 32
Dependent Claim 35 words
The melt processable poly(ester-amide) of claim 28 which exhibits an inherent viscosity within the range of approximately 3.0 to 9.0 dl./g. when measured at a concentration of 0.1 weight/volume percent in pentafluorophenol at 60° C.
Claim 33
Dependent Claim 55 words
The melt processable poly(ester-amide) of claim 27 consisting essentially of approximately 15 to 40 mole percent of moiety I, approximately 15 to 40 mole percent of moiety II, approximately 15 to 35 mole percent of moiety III, approximately 5 to 35 mole percent of moiety IV, and approximately 0 to 25 percent of moiety V.
Claim 34
Dependent Claim 26 words
The melt processable poly(ester-amide) of claim 30 wherein the moiety V is present in a concentration within the range of approximately 5 to 25 mole percent.
Claim 35
Dependent Claim 15 words
The melt processable poly(ester-amide) of claim 27 wherein said moiety II is a p-oxybenzoyl moiety.
Claim 36
Dependent Claim 15 words
The melt processable poly(ester-amide) of claim 27 wherein said moiety III is a terephthaloyl moiety.
Claim 37
Dependent Claim 17 words
The melt processable poly(ester-amide) of claim 27 wherein said moiety IV is derived from p-aminophenol or p-phenylenediamine.
Claim 38
Dependent Claim 15 words
The melt processable poly(ester-amide) of claim 27 wherein said moiety V is derived from hydroquinone.
Claim 39
Dependent Claim 27 words
A molding compound comprising the melt processable poly(ester-amide) of claim 27 which incorporates approximately 1 to 60 percent by weight of a solid filler and/or reinforcing agent.
Claim 40
Dependent Claim 11 words
A molded article comprising the melt processable poly(ester-amide) of claim 27.
Claim 41
Dependent Claim 15 words
A fiber which has been melt spun from the melt processable poly(ester-amide) of claim 27.
Claim 42
Dependent Claim 15 words
A film which has been melt extruded from the melt processable poly(ester-amide) of claim 27.

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) 1985-09-27 1986-03-29 1986-09-28 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1989-09-27 1990-03-29 1990-09-28 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1993-09-27 1994-03-29 1994-09-28 $7700.00 Window Closed / Lapsed

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