Patent US4294957A successfully refreshed from Google Patents.
US4294957A
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Process for preparing polyarylates
Assignee: BP Corp North America Inc
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Filing: 1979-08-27
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Granted: 1981-10-13
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Expires: 1999-08-27
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.
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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 |