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US4355132A Expired / Lapsed US ⏱️ 0.0 years remaining

Anisotropic melt phase forming poly(ester-amide) derived from p-hydroxybenzoic acid, 2,6-naphthalenedicarboxylic acid, aromatic monomer capable of forming an amide linkage, and, optionally, hydroquinone and additional carbocyclic dicarboxylic acid

Assignee: Celanese Corp
•
Filing: 1981-04-07
•
Granted: 1982-10-19
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Expires: 2001-04-07
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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-dicarboxynaphthalene moiety, (c) aromatic moiety capable of forming an amide linkage in the polymer, and, optionally, (d) p-dioxyphenyl moiety and (e) other carbocyclic dicarboxyl moiety, in the proportions indicated. Preferably, the aromatic moiety capable of forming an amide linkage is derived from p-aminophenol or p-phenylenediamine. The carbocyclic dicarboxyl moiety is preferably aromatic. 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

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

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-26 08:17
CPC Classifications
C; C08; C08G; C08G69/00; C08G69/44

Claims Analysis

Total Claims: 48
Claim 1
Independent Claim 261 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, and, optionally, IV and V wherein: I is ##STR11## II is ##STR12## III 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; IV is ##STR13## V is ##STR14## where A is a divalent carbocyclic radical 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 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 20 to 70 mole percent, moiety II is present in a concentration within the range of approximately 5 to 35 mole percent, moiety III is present in a concentration within the range of approximately 5 to 35 mole percent, moiety IV is present in a concentration within the range of approximately 0 to 35 mole percent, and moiety V is present in a concentration within the range of approximately 0 to 30 mole percent, and with said poly(ester-amide) being wholly aromatic with the possible exception of said carbocyclic moiety V in the sense that each moiety present contributes at least one aromatic ring.
Claim 2
Dependent Claim 261 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, and, optionally, IV and V wherein: I is ##STR11## II is ##STR12## III 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; IV is ##STR13## V is ##STR14## where A is a divalent carbocyclic radical 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 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 20 to 70 mole percent, moiety II is present in a concentration within the range of approximately 5 to 35 mole percent, moiety III is present in a concentration within the range of approximately 5 to 35 mole percent, moiety IV is present in a concentration within the range of approximately 0 to 35 mole percent, and moiety V is present in a concentration within the range of approximately 0 to 30 mole percent, and with said poly(ester-amide) being wholly aromatic with the possible exception of said carbocyclic moiety V in the sense that each moiety present contributes at least one aromatic ring.
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 70 words
The melt processable poly(ester-amide) of claim 1 wherein the total molar concentration of moieties II and V is substantially equal to the total molar concentration of moieties III and IV and the total molar concentration of moieties II and V and the total molar concentration of moieties III and IV 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 39 words
The melt processable poly(ester-amide) of claim 1 wherein the total molar concentration of moieties II and V and the total molar concentration of moieties III and IV is each within the range of approximately 15 to 40 mole percent.
Claim 8
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 30 to 60 mole percent.
Claim 9
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 5 to 25 mole percent.
Claim 10
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 5 to 25 mole percent.
Claim 11
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 0 to 20 mole percent.
Claim 12
Dependent Claim 25 words
The melt processable poly(ester-amide) of claim 10 wherein moiety IV is present in a concentration within the range of approximately 5 to 15 mole percent.
Claim 13
Dependent Claim 25 words
The melt processable poly(ester-amide) of claim 1 wherein the divalent carbocyclic radical of moiety V 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 V comprises at least one armoatic ring.
Claim 15
Dependent Claim 25 words
The melt processable poly(ester-amide) of claim 1 wherein moiety V is present in a concentration within the range of approximately 0 to 25 mole percent.
Claim 16
Dependent Claim 25 words
The melt processable poly(ester-amide) of claim 14 wherein moiety V is present in a concentration within the range of approximately 5 to 15 mole percent.
Claim 17
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 18
Dependent Claim 11 words
A molded article comprising the melt processable poly(ester-amide) of claim 1.
Claim 19
Dependent Claim 15 words
A fiber which has been melt spun from the melt processable poly(ester-amide) of claim 1.
Claim 20
Dependent Claim 15 words
A film which has been melt extruded from the melt processable poly(ester-amide) of claim 1.
Claim 21
Dependent Claim 255 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, and, optionally, IV and V wherein: I is ##STR15## II is ##STR16## III is --Y-Ar-Z--, where Ar is a divalent radical comprising at least one aromatic ring, Y is 0, 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; IV is ##STR17## V is ##STR18## where A 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 30 to 60 mole percent, moiety II is present in a concentration within the range of approximately 5 to 25 mole percent, moiety III is present within the range of approximately 5 to 25 mole percent, moiety IV is present in a concentration within the range of approximately 0 to 20 mole percent, and moiety V is present in a concentration within the range of approximately 0 to 25 mole percent and with said poly(ester-amide) being wholly aromatic in the sense that each moiety present contributes at least one aromatic ring.
Claim 22
Dependent Claim 255 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, and, optionally, IV and V wherein: I is ##STR15## II is ##STR16## III is --Y-Ar-Z--, where Ar is a divalent radical comprising at least one aromatic ring, Y is 0, 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; IV is ##STR17## V is ##STR18## where A 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 30 to 60 mole percent, moiety II is present in a concentration within the range of approximately 5 to 25 mole percent, moiety III is present within the range of approximately 5 to 25 mole percent, moiety IV is present in a concentration within the range of approximately 0 to 20 mole percent, and moiety V is present in a concentration within the range of approximately 0 to 25 mole percent and with said poly(ester-amide) being wholly aromatic in the sense that each moiety present contributes at least one aromatic ring.
Claim 23
Dependent Claim 23 words
The melt processable poly(ester-amide) of claim 20 which is capable of forming an anisotropic melt phase at a temperature below approximately 350° C.
Claim 24
Dependent Claim 32 words
The melt processable poly(ester-amide) of claim 20 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 25
Dependent Claim 35 words
The melt processable poly(ester-amide) of claim 22 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 26
Dependent Claim 70 words
The melt processable poly(ester-amide) of claim 20 wherein the total molar concentration of moieties II and V is substantially equal to the total molar concentration of moieties III and IV and the total molar concentration of moieties II and V and the total molar concentration of moieties III and IV each is substantially equal to one-half of the difference between 100 mole percent and the molar concentration of moiety I.
Claim 27
Dependent Claim 39 words
The melt processable poly(ester-amide) of claim 20 wherein the total molar concentration of moieties II and V and the total molar concentration of moieties III and IV each is within the range of approximately 20 to 35 mole percent.
Claim 28
Dependent Claim 25 words
The melt processable poly(ester-amide) of claim 20 wherein moiety I is present in a concentration within the range of approximately 40 to 60 mole percent.
Claim 29
Dependent Claim 25 words
The melt processable poly(ester-amide) of claim 20 wherein moiety II is present in a concentration within the range of approximately 10 to 25 mole percent.
Claim 30
Dependent Claim 25 words
The melt processable poly(ester-amide) of claim 20 wherein moiety III is present in a concentration within the range of approximately 10 to 15 mole percent.
Claim 31
Dependent Claim 25 words
The melt processable poly(ester-amide) of claim 20 wherein moiety IV is present in a concentration within the range of approximately 0 to 15 mole percent.
Claim 32
Dependent Claim 25 words
The melt processable poly(ester-amide) of claim 29 wherein moiety IV is present in a concentration within the range of approximately 5 to 15 mole percent.
Claim 33
Dependent Claim 25 words
The melt processable poly(ester-amide) of claim 20 wherein moiety V is present in a concentration within the range of approximately 5 to 15 mole percent.
Claim 34
Dependent Claim 27 words
A molding compound comprising the melt processable poly(ester-amide) of claim 20 which incorporates approximately 1 to 60 percent by weight of a solid filler and/or reinforcing agent.
Claim 35
Dependent Claim 11 words
A molded article comprising the melt processable poly(ester-amide) of claim 20.
Claim 36
Dependent Claim 15 words
A fiber which has been melt spun from the melt processable poly(ester-amide) of claim 20.
Claim 37
Dependent Claim 15 words
A film which has been melt extruded from the melt processable poly(ester-amide) of claim 20.
Claim 38
Dependent Claim 293 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 (optional), and V wherein: I is ##STR19## II is ##STR20## III 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; IV is ##STR21## V is ##STR22## where A 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 10 to 15 mole percent, moiety IV is present in a concentration within the range of approximately 0 to 15 mole percent, and moiety V is present in a concentration within the range of approximately 5 to 15 mole percent, with the total molar concentration of moieties II and V being substantially equal to the total molar concentration of moieties III and IV and with the total molar concentration of moieties II and V and the total molar concentration of moieties III and IV each being within the range of approximately 20 to 30 mole percent.
Claim 39
Dependent Claim 293 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 (optional), and V wherein: I is ##STR19## II is ##STR20## III 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; IV is ##STR21## V is ##STR22## where A 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 10 to 15 mole percent, moiety IV is present in a concentration within the range of approximately 0 to 15 mole percent, and moiety V is present in a concentration within the range of approximately 5 to 15 mole percent, with the total molar concentration of moieties II and V being substantially equal to the total molar concentration of moieties III and IV and with the total molar concentration of moieties II and V and the total molar concentration of moieties III and IV each being within the range of approximately 20 to 30 mole percent.
Claim 40
Dependent Claim 32 words
The melt processable poly(ester-amide) of claim 36 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 41
Dependent Claim 35 words
The melt processable poly(ester-amide) of claim 37 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 42
Dependent Claim 25 words
The melt processable poly(ester-amide) of claim 36 wherein moiety IV is present in a concentration within the range of approximately 5 to 15 mole percent.
Claim 43
Dependent Claim 16 words
The melt processable poly(ester-amide) of claim 36 wherein moiety III is derived from p-aminophenol or p-phenylenediamine.
Claim 44
Dependent Claim 14 words
The melt processable poly(ester-amide) of claim 36 wherein moiety V is a terephthaloyl moiety.
Claim 45
Dependent Claim 27 words
A molding compound comprising the melt processable poly(ester-amide) of claim 36 which incorporates approximately 1 to 60 percent by weight of a solid filler and/or reinforcing agent.
Claim 46
Dependent Claim 11 words
A molded article comprising the melt processable poly(ester-amide) of claim 36.
Claim 47
Dependent Claim 15 words
A fiber which has been melt spun from the melt processable poly(ester-amide) of claim 36.
Claim 48
Dependent Claim 15 words
A film which has been melt extruded from the melt processable poly(ester-amide) of claim 36.

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) 1985-10-18 1986-04-19 1986-10-19 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1989-10-18 1990-04-19 1990-10-19 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1993-10-18 1994-04-19 1994-10-19 $7700.00 Window Closed / Lapsed

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