US4423202A
Expired / Lapsed
US
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Process for the production of high molecular weight para ordered aromatic heterocyclic polymer
Assignee: Celanese Corp
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Filing: 1981-05-05
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Granted: 1983-12-27
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Expires: 2001-05-05
Abstract
Abstract A process for the production of para ordered aromatic heterocyclic polymer is provided. The process comprises heating a first reactant with the dichloride derivative of at least one aromatic dicarboxylic acid in polyphosphoric acid at a temperature within the range of approximately 100° C. to 250° C. until the polymerization reaction is complete. The first reactant comprises at least one aromatic diaminodiol or at least one aromatic diaminodithiol, wherein each amine group is paired with a hydroxy group or a thiol group upon adjacent carbon atoms of the aromatic nucleus. Preferably, the process of the present invention is employed in the production of para ordered aromatic polybisoxazoles wherein the first reactant comprises at least one aromatic diaminodiol. In an especially preferred embodiment, the present invention provides a process for the production of high molecular weight polyparaphenylenebenzobisoxazole, the process comprising heating 4,6-diaminoresorcinol with terephthaloyl dichloride in polyphosphoric acid.
Inventors
- 👤 Eui W. Choe
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 21:48
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/22; C08G75/00; C08G75/32
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
83 words
A process for the production of para ordered heterocyclic polymer having a number average molecular weight of at least approximately 10,000 which comprises heating a first reactant selected from the group consisting of ##STR7## their dihydrochloride salts and mixtures thereof with at least one dihalogen derivative selected from the group consisting of ##STR8## wherein X is F, Cl, Br or I, in polyphosphoric acid at a temperature within the range of approximately 100° C. to 250° C. until the polymerization reaction is complete.
Claim 2
Dependent Claim
83 words
A process for the production of para ordered heterocyclic polymer having a number average molecular weight of at least approximately 10,000 which comprises heating a first reactant selected from the group consisting of ##STR7## their dihydrochloride salts and mixtures thereof with at least one dihalogen derivative selected from the group consisting of ##STR8## wherein X is F, Cl, Br or I, in polyphosphoric acid at a temperature within the range of approximately 100° C. to 250° C. until the polymerization reaction is complete.
Claim 3
Dependent Claim
94 words
A process for the production of para ordered aromatic polybisoxazoles having a number average molecular weight of at least approximately 10,000 which comprises heating at least one aromatic diaminodiol selected from the group consisting of ##STR9## their dihydrochloride salts and mixtures thereof with at least one dihalogen derivative of at least one aromatic dicarboxylic acid selected from the group consisting of ##STR10## and mixtures thereof wherein X is F, Cl, Br or I in polyphosphoric acid at a temperature within the range of approximately 100° C. to 250° C. until the polymerization is complete.
Claim 4
Dependent Claim
94 words
A process for the production of para ordered aromatic polybisoxazoles having a number average molecular weight of at least approximately 10,000 which comprises heating at least one aromatic diaminodiol selected from the group consisting of ##STR9## their dihydrochloride salts and mixtures thereof with at least one dihalogen derivative of at least one aromatic dicarboxylic acid selected from the group consisting of ##STR10## and mixtures thereof wherein X is F, Cl, Br or I in polyphosphoric acid at a temperature within the range of approximately 100° C. to 250° C. until the polymerization is complete.
Claim 5
Dependent Claim
13 words
The process of claim 1 wherein said dihalogen derivative is the dichloride derivative.
Claim 6
Dependent Claim
17 words
The process of claim 3 further comprising the step of dehydrochlorinating the reaction mixture prior to polymerization.
Claim 7
Dependent Claim
25 words
The process of 1 wherein said para ordered aromatic heterocyclic polymer exhibits a number average molecular weight within the range of approximately 10,000 to 30,000.
Claim 8
Dependent Claim
25 words
The process of 1 wherein said para ordered aromatic heterocyclic polymer exhibits a number average molecular weight within the range of approximately 10,000 to 30,000.
Claim 9
Dependent Claim
12 words
The process of claim 1 wherein said heating is conducted by stages.
Claim 10
Dependent Claim
29 words
The process of claim 1 wherein said dihalogen derivative is employed in an amount within the range of approximately 0.8 to 1.2 mole per mole of said first reactant.
Claim 11
Dependent Claim
19 words
The process of claim 1 wherein said dihalogen derivative and said first reactant are employed in substantially equimolar amounts.
Claim 12
Dependent Claim
29 words
The process of claim 1 wherein said polyphosphoric acid is employed in an amount within the range of approximately 10 to 120 times the weight of said first reactant.
Claim 13
Dependent Claim
10 words
The process of claim 2 wherein said diaminodiol is 4,6-diaminoresorcinol.
Claim 14
Dependent Claim
13 words
The process of claim 2 wherein said dihalogen derivative is the dichloride derivative.
Claim 15
Dependent Claim
12 words
The process of claim 2 wherein said dihalogen derivative is terephthaloyl dichloride.
Claim 16
Dependent Claim
17 words
The process of claim 11 further comprising the step of dehydrochlorinating the reaction mixture prior to polymerization.
Claim 17
Dependent Claim
25 words
The process of claim 2 wherein said para ordered aromatic polybisoxazole exhibits a number average molecular weight within the range of approximately 10,000 to 30,000.
Claim 18
Dependent Claim
12 words
The process of claim 2 wherein said heating is conducted by stages.
Claim 19
Dependent Claim
28 words
The process of claim 2 wherein said dihalogen derivative is employed in an amount within the range of approximately 0.8 to 1.2 mole per mole of said diaminodiol.
Claim 20
Dependent Claim
18 words
The process of claim 16 wherein said dihalogen derivative and said diaminodiol are employed in substantially equimolar amounts.
Claim 21
Dependent Claim
28 words
The process of claim 2 wherein said polyphosphoric acid is employed in an amount within the range of approximately 10 to 120 times the weight of said diaminodiol.
Claim 22
Dependent Claim
116 words
A process for the production of polyparaphenylenebenzobisoxazole having a number average molecular weight of at least approximately 10,000 which exhibits an inherent viscosity of at least approximately 2.0 dl./g. when measured at a concentration of approximately 0.2 weight/volume percent in methanesulfonic acid at 25° C., said process comprising the steps of: (a) dehydrochlorinating a mixture of 4,6-diaminoresorcinol with terephthaloyl dichloride in polyphosphoric acid by heating the reaction mixture within the range of approximately 30° C. to 95° C. for a period of time sufficient to dehydrochlorinate said reaction mixture; and (b) polymerizing said reaction mixture by heating said reaction mixture within the range of approximately 100° C. to 250° C. until the polymerization reaction is complete.
Claim 23
Dependent Claim
116 words
A process for the production of polyparaphenylenebenzobisoxazole having a number average molecular weight of at least approximately 10,000 which exhibits an inherent viscosity of at least approximately 2.0 dl./g. when measured at a concentration of approximately 0.2 weight/volume percent in methanesulfonic acid at 25° C., said process comprising the steps of: (a) dehydrochlorinating a mixture of 4,6-diaminoresorcinol with terephthaloyl dichloride in polyphosphoric acid by heating the reaction mixture within the range of approximately 30° C. to 95° C. for a period of time sufficient to dehydrochlorinate said reaction mixture; and (b) polymerizing said reaction mixture by heating said reaction mixture within the range of approximately 100° C. to 250° C. until the polymerization reaction is complete.
Claim 24
Dependent Claim
14 words
The process of claim 19 wherein said 4,6-diaminoresorcinol is initially provided as the dihydrochloride.
Claim 25
Dependent Claim
14 words
The process of claim 19 wherein said dehydrochlorinating step (a) is conducted by stages.
Claim 26
Dependent Claim
21 words
The process of claim 19 wherein said dehydrochlorinating step (a) is conducted for a period of time of approximately 24 hours.
Claim 27
Dependent Claim
14 words
The process of claim 19 wherein said polymerizing step (b) is conducted by stages.
Claim 28
Dependent Claim
28 words
The process of claim 19 wherein said terephthaloyl dichloride is employed in an amount within the range of approximately 0.8 to 1.2 mole per mole of said 4,6-diaminoresorcinol.
Claim 29
Dependent Claim
18 words
The process of claim 24 wherein said terephthaloyl dichloride and said 4,6-diaminoresorcinol are employed in substantially equimolar amounts.
Claim 30
Dependent Claim
28 words
The process of claim 19 wherein said polyphosphoric acid is employed in an amount within the range of approximately 10 to 120 times the weight of said 4,6-diaminoresorcinol.
Claim 31
Dependent Claim
37 words
The process of claim 19 wherein said polyparaphenylenebenzobisoxazole exhibits an inherent viscosity within the range of approximately 2.0 to 4.0. dl./g. when measured at a concentration of approximately 0.2 weight/volume percent in methanesulfonic acid at 25° C.
References Cited (Backward Citations)
US3313783A
Cited
US4225700A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-12-26 | 1987-06-27 | 1987-12-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-12-26 | 1991-06-27 | 1991-12-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-12-26 | 1995-06-27 | 1995-12-27 | $7700.00 | Window Closed / Lapsed |