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US4294957A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for preparing polyarylates

Assignee: BP Corp North America Inc
•
Filing: 1979-08-27
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Granted: 1981-10-13
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Expires: 1999-08-27
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Abstract

Abstract Described herein is a process for preparing polyarylates of improved color which comprises reacting a diester derivative of a dihydric phenol with an aromatic dicarboxylic acid in the presence of from about 10 to about 60 weight percent of at least one cycloaliphatic, substituted aromatic or heteroaromatic compound, which compounds contain at least one benzylic and/or tertiary hydrogen atom, at a temperature of from about 260° to about 350° C. Optionally, the process may be carried out in the presence of a magnesium, manganese, or zinc catalyst.

Inventors

  • 👤 Mitchell H. Berger
  • 👤 Louis M. Maresca
  • 👤 Markus Matzner

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-30 18:03
CPC Classifications
C; C08; C08G; C08G63/00; C08G63/02; C08G63/12; C08G63/16; C08G63/18; C08G63/19; C08G63/78; C08G63/81

Claims Analysis

Total Claims: 18
Claim 1
Independent Claim 209 words
A process for preparing polyarylate having a reduced viscosity of from about 0.5 to greater than 1.0 dl/gm and improved color which process comprises reacting, at a temperature of from about 260° to about 350° C.: (a) at least one diester derivative of a dihydric phenol having the following formula: ##STR7## wherein R is independently selected from an alkyl radical having from 1 to about 6 carbon atoms or cycloalkyl having from 4 to about 7 carbon atoms, y is independently selected from alkyl groups of 1 to 4 carbon atoms, chlorine, or bromine, z independently has a value of from 0 to 4, inclusive, and R' is independently selected from a divalent saturated aliphatic hydrocarbon radical having 1 to 8 carbon atoms, a cycloalkylene, or cycloalkylidene radical having up to and including 9 carbon atoms, O, S, SO, SO 2 , CO, x is 0 or 1; with (b) at least one aromatic dicarboxylic acid, in the presence of from about 10 to about 60 weight percent, based on the polyarylate produced, of at least one cycloaliphatic, substituted aromatic or heteroaromatic compound, which compounds contain at least one benzylic and/or tertiary hydrogen atom, and have a boiling point of about 150° to about 350° C. at atmospheric pressure.
Claim 2
Dependent Claim 209 words
A process for preparing polyarylate having a reduced viscosity of from about 0.5 to greater than 1.0 dl/gm and improved color which process comprises reacting, at a temperature of from about 260° to about 350° C.: (a) at least one diester derivative of a dihydric phenol having the following formula: ##STR7## wherein R is independently selected from an alkyl radical having from 1 to about 6 carbon atoms or cycloalkyl having from 4 to about 7 carbon atoms, y is independently selected from alkyl groups of 1 to 4 carbon atoms, chlorine, or bromine, z independently has a value of from 0 to 4, inclusive, and R' is independently selected from a divalent saturated aliphatic hydrocarbon radical having 1 to 8 carbon atoms, a cycloalkylene, or cycloalkylidene radical having up to and including 9 carbon atoms, O, S, SO, SO 2 , CO, x is 0 or 1; with (b) at least one aromatic dicarboxylic acid, in the presence of from about 10 to about 60 weight percent, based on the polyarylate produced, of at least one cycloaliphatic, substituted aromatic or heteroaromatic compound, which compounds contain at least one benzylic and/or tertiary hydrogen atom, and have a boiling point of about 150° to about 350° C. at atmospheric pressure.
Claim 3
Dependent Claim 20 words
A process as defined in claim 1 wherein the diester derivative of a dihydric phenol has the following formula: ##STR8##
Claim 4
Dependent Claim 12 words
A process as defined in claim 2 wherein each z is 0.
Claim 5
Dependent Claim 21 words
A process as defined in claim 1 wherein the aromatic dicarboxylic acid is a mixture of isophthalic acid and terephthalic acid.
Claim 6
Dependent Claim 24 words
A process as defined in claim 4 wherein the isophthalic acid to terephthalic acid ratio in the mixture is about 25:75 to about 100:0.
Claim 7
Dependent Claim 18 words
A process as defined in claim 1 wherein the temperature is between about 275° to about 295° C.
Claim 8
Dependent Claim 45 words
A process as defined in claim 1 wherein the cycloaliphatic compound is of the following formulae: ##STR9## wherein R 1 is independently alkyl of 1 to 6 carbon atoms, cycloalkyl of 6 to 18 carbon atoms, and a is an integer of 1 or 2.
Claim 9
Dependent Claim 114 words
A process as defined in claim 1 wherein the substituted aromatic compound is of the following formulae: ##STR10## wherein R 2 is independently alkyl of 1 to 6 carbon atoms, cycloalkyl of 6 to 18 carbon atoms and aralkyl or alkaryl of 7 to 18 carbon atoms and wherein the carbon atom of R 2 attached directly to the benzene nucleus has 1 or 2 attached hydrogen atoms, and b is an integer of 1 to 6; ##STR11## wherein R 3 is independently alkyl of 1 to 6 carbon atoms, cycloalkyl of 6 to 18 carbon atoms, c is an integer of 1 or 2, and n is an integer of 1 to 6.
Claim 10
Dependent Claim 23 words
A process as defined in claim 8 wherein the substituted aromatic compound is selected from xylene, cumene, diethylbenzene, diisopropyl benzene, tetrahydronaphthalene, or decahydronaphthalene.
Claim 11
Dependent Claim 72 words
A process as defined in claim 1 wherein the heteroaromatic compound is of the following formula: ##STR12## wherein A is S, O, or --CH═N--, R 4 is independently alkyl of 1 to 6 carbon atoms, or cycloalkyl of 6 to 18 carbon atoms wherein the carbon atom of R 4 attached directly to the heteroaromatic nucleus has 1 or 2 attached hydrogen atoms, and d is an integer of 1 or 2.
Claim 12
Dependent Claim 21 words
A process as defined in claim 1 wherein the polyarylate has a reduced viscosity of from about 0.6 to about 0.8.
Claim 13
Dependent Claim 29 words
A process as defined in claim 1 wherein the cycloaliphatic, substituted aromatic or heteroaromatic compound is present in an amount of from about 25 to about 40 weight percent.
Claim 14
Dependent Claim 189 words
A process for preparing a polyarylate having a reduced viscosity of from about 0.5 to greater than 1.0 dl/gm which process comprises reacting at a temperature of from about 260° to about 350° C.: (a) an acid anhydride based on an acid containing from 2 to 8 carbon atoms; (b) at least one dihydric phenol having the following formula: ##STR13## wherein y is independently selected from alkyl groups of 1 to 4 carbon atoms, chlorine or bromine, z independently has a value of from 0 to 4, inclusive, R' is independently selected from a divalent saturated hydrocarbon radical having 1 to 8 carbon atoms, a cycloalkylene or cycloalkylidene radical having up to and including 9 carbon atoms, O, S, SO, SO 2 , Co, x is 0 or 1; and (c) at least one aromatic dicarboxylic acid, in the presence of from about 10 to about 60 weight percent, based on the polyarylate produced, of at least one cycloaliphatic, substituted aromatic or heteroaromatic compound, which compounds contain at least one benzylic and/or tertiary hydrogen, and have a boiling point of about 150° to about 350° C. at atmospheric pressure.
Claim 15
Dependent Claim 189 words
A process for preparing a polyarylate having a reduced viscosity of from about 0.5 to greater than 1.0 dl/gm which process comprises reacting at a temperature of from about 260° to about 350° C.: (a) an acid anhydride based on an acid containing from 2 to 8 carbon atoms; (b) at least one dihydric phenol having the following formula: ##STR13## wherein y is independently selected from alkyl groups of 1 to 4 carbon atoms, chlorine or bromine, z independently has a value of from 0 to 4, inclusive, R' is independently selected from a divalent saturated hydrocarbon radical having 1 to 8 carbon atoms, a cycloalkylene or cycloalkylidene radical having up to and including 9 carbon atoms, O, S, SO, SO 2 , Co, x is 0 or 1; and (c) at least one aromatic dicarboxylic acid, in the presence of from about 10 to about 60 weight percent, based on the polyarylate produced, of at least one cycloaliphatic, substituted aromatic or heteroaromatic compound, which compounds contain at least one benzylic and/or tertiary hydrogen, and have a boiling point of about 150° to about 350° C. at atmospheric pressure.
Claim 16
Dependent Claim 253 words
A process for preparing a polyarylate having a reduced viscosity of from about 0.5 to greater than 1.0 dl/gm, which process comprises the following steps: I. forming a polyarylate prepolymer having a reduced viscosity of from about 0.1 to about 0.4 dl/gm, by reacting: (a) at least one diester derivative of a dihydric phenol having the following formula: ##STR14## wherein R is independently an alkyl radical having from 1 to about 6 carbon atoms, or cycloalkyl having from 4 to about 7 carbon atoms, y is independently selected from alkyl groups of 1 to 4 carbon atoms, chlorine, or bromine, z independently has a value of from 0 to 4, inclusive, and R' is independently selected from a divalent saturated aliphatic hydrocarbon radical having 1 to 8 carbon atoms, a cycloalkylene, or cycloalkylidene radical having up to and including 9 carbon atoms, O, S, SO, SO 2 , CO, x is 0 or 1; with (b) at least one aromatic dicarboxylic acid, in the presence of from about 10 to about 60 weight percent, based on the polyarylate produced, of at least one cycloaliphatic, substituted aromatic or heteroaromatic compound, which compounds contain at least one benzylic and/or tertiary hydrogen, and have a boiling point of about 150° to about 350° C. at atmospheric pressure. II. Heating the prepolymer so formed at a temperature of from about 300° to 350° C. for a period of time sufficient to form a polyarylate having a reduced viscosity of from about 0.5 to greater than 1.0 dl/g.
Claim 17
Dependent Claim 253 words
A process for preparing a polyarylate having a reduced viscosity of from about 0.5 to greater than 1.0 dl/gm, which process comprises the following steps: I. forming a polyarylate prepolymer having a reduced viscosity of from about 0.1 to about 0.4 dl/gm, by reacting: (a) at least one diester derivative of a dihydric phenol having the following formula: ##STR14## wherein R is independently an alkyl radical having from 1 to about 6 carbon atoms, or cycloalkyl having from 4 to about 7 carbon atoms, y is independently selected from alkyl groups of 1 to 4 carbon atoms, chlorine, or bromine, z independently has a value of from 0 to 4, inclusive, and R' is independently selected from a divalent saturated aliphatic hydrocarbon radical having 1 to 8 carbon atoms, a cycloalkylene, or cycloalkylidene radical having up to and including 9 carbon atoms, O, S, SO, SO 2 , CO, x is 0 or 1; with (b) at least one aromatic dicarboxylic acid, in the presence of from about 10 to about 60 weight percent, based on the polyarylate produced, of at least one cycloaliphatic, substituted aromatic or heteroaromatic compound, which compounds contain at least one benzylic and/or tertiary hydrogen, and have a boiling point of about 150° to about 350° C. at atmospheric pressure. II. Heating the prepolymer so formed at a temperature of from about 300° to 350° C. for a period of time sufficient to form a polyarylate having a reduced viscosity of from about 0.5 to greater than 1.0 dl/g.
Claim 18
Dependent Claim 21 words
A process as defined in claim 14 wherein the prepolymer is heated in step (II) in a vented extruder under vacuum.

References Cited (Backward Citations)

US2595343A Cited
US3317464A Cited
US3329653A Cited
US3225003A Cited
US3684766A Cited
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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-10-12 1985-04-13 1985-10-13 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-10-12 1989-04-13 1989-10-13 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-10-12 1993-04-13 1993-10-13 $7700.00 Window Closed / Lapsed

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