US4042564A
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Method for preparing polyphenylene ethers
Assignee: General Electric Co
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Filing: 1975-11-11
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Granted: 1977-08-16
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Expires: 1995-11-11
Abstract
Abstract A novel process for the preparation of polyphenylene ethers is disclosed that is based on the addition of a polyethoxylated quaternary ammonium salt to the reaction mixture.
Inventors
- 👤 James Gordy Bennett, Jr.
- 👤 Glenn Dale Cooper
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 01:07
CPC Classifications
C; C08; C08G; C08G65/00; C08G65/34; C08G65/38; C08G65/44
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
137 words
In a process for the preparation of a high-molecular weight polyphenylene ether having a degree of polymerization of at least 50 by oxidatively coupling a monovalent phenol having substitution in at least the two ortho positions and hydrogen or halogen in the para-position, using an oxygen-containing gas, a solvent and a complex catalyst comprising a metal salt and an amine as an oxidizing agent, the improvement which comprises adding to the reaction mixture from 0.001 to 0.2 percent by weight of reaction mixture a compound of the formula: ##STR4## wherein R 1 and R 2 may both be alkyl of from 6-22 carbon atoms or alkenyl of from 10-22 carbon atoms or one of R 1 and R 2 may be -(CH 2 CH 2 -o-).sub. x H; x is an integer of from 1 to 40.
Claim 2
Dependent Claim
137 words
In a process for the preparation of a high-molecular weight polyphenylene ether having a degree of polymerization of at least 50 by oxidatively coupling a monovalent phenol having substitution in at least the two ortho positions and hydrogen or halogen in the para-position, using an oxygen-containing gas, a solvent and a complex catalyst comprising a metal salt and an amine as an oxidizing agent, the improvement which comprises adding to the reaction mixture from 0.001 to 0.2 percent by weight of reaction mixture a compound of the formula: ##STR4## wherein R 1 and R 2 may both be alkyl of from 6-22 carbon atoms or alkenyl of from 10-22 carbon atoms or one of R 1 and R 2 may be -(CH 2 CH 2 -o-).sub. x H; x is an integer of from 1 to 40.
Claim 3
Dependent Claim
74 words
A process as defined in claim 1 wherein the polyphenylene ether has repeating units of the formula: ##STR5## wherein the oxygen ether atom of one unit is connected to the benzene nucleus of the next adjoining unit, n is an integer of at least 50; and Q and Q' are monovalent substituents selected from hydrogen, halogen, hydrocarbon radicals, halohydrocarbon radicals having at least two carbon atoms between the halogen atom and the phenyl nucleus.
Claim 4
Dependent Claim
14 words
A process as defined in claim 2 wherein said polyphenylene ether is poly(2,6-dimethyl-1,4-phenylene ether).
Claim 5
Dependent Claim
23 words
A process as defined in claim 3 wherein said reaction mixture also includes an alkali metal bromide or an alkaline earth metal bromide.
Claim 6
Dependent Claim
31 words
A process as defined in claim 4 wherein said reaction is carried out in the presence of a complex catalyst comprising a cupric salt or a cuprous salt and a diamine.
Claim 7
Dependent Claim
26 words
A process as defined in claim 2 wherein the compound of formula I is employed in an amount of from 0.01-0.2% by weight of monovalent phenol.
Claim 8
Dependent Claim
36 words
A process as defined in claim 5 wherein said reaction promoter is a compound of the formula: ##STR6## wherein R is alkyl of 16-18 carbon atoms and s and t are integers of from 1- 20.
Claim 9
Dependent Claim
159 words
In a process for the preparation of a high-molecular weight polyphenylene ether having a degree of polymerization of at least 50 by oxidatively coupling a monovalent phenol having substitution in at least the two ortho positions and hydrogen or halogen in the para-position, using an oxygencontaining gas, a solvent and a complex catalyst comprising a copper salt and an amine as an oxidizing agent, a copper chelating agent for the termination of the reaction after the polyphenylene ether reaches the desired molecular weight, the improvement which comprises adding to the reaction mixture, when the polyphenylene ether reaches the desired molecular weight, an extraction promoting amount of a compound of the formula: ##STR7## wherein R 1 and R 2 may both be alkyl of from 6-22 carbon atoms or alkenyl of from 6-22 carbon atoms or one of R 1 and R 2 may be -(CH 2 CH 2 -O-).sub. x H; x is an integer of from 1 to
Claim 10
Dependent Claim
159 words
In a process for the preparation of a high-molecular weight polyphenylene ether having a degree of polymerization of at least 50 by oxidatively coupling a monovalent phenol having substitution in at least the two ortho positions and hydrogen or halogen in the para-position, using an oxygencontaining gas, a solvent and a complex catalyst comprising a copper salt and an amine as an oxidizing agent, a copper chelating agent for the termination of the reaction after the polyphenylene ether reaches the desired molecular weight, the improvement which comprises adding to the reaction mixture, when the polyphenylene ether reaches the desired molecular weight, an extraction promoting amount of a compound of the formula: ##STR7## wherein R 1 and R 2 may both be alkyl of from 6-22 carbon atoms or alkenyl of from 6-22 carbon atoms or one of R 1 and R 2 may be -(CH 2 CH 2 -O-).sub. x H; x is an integer of from 1 to
Claim 11
Dependent Claim
72 words
A process as defined in claim 8 wherein the polyphenylene ether is of the formula: ##STR8## wherein the oxygen ether atom of one unit is connected to the benzene nucleus of the next adjoining unit, n is an integer of at least 50; and Q and Q' are monovalent substituents selected from hydrogen, halogen, hydrocarbon radicals, halohydrocarbon radicals having at least two carbon atoms between the halogen atom and the phenyl nucleus.
Claim 12
Dependent Claim
14 words
A process as defined in claim 8 wherein said polyphenylene ether is poly(2,6-dimethyl-1,4-phenylene ether).
Claim 13
Dependent Claim
23 words
A process as defined in claim 10 wherein said reaction mixture also includes an alkali metal bromide or an alkaline earth metal bromide.
Claim 14
Dependent Claim
29 words
A process as defined in claim 10 wherein said reaction mixture is carried out in the presence of a complex catalyst comprising a cupric salt and a secondary amine.
Claim 15
Dependent Claim
26 words
A process as defined in claim 8 wherein the compound of formula I is employed in an amount of 10-200 parts per million parts of solvent.
Claim 16
Dependent Claim
37 words
A process as defined in claim 8 wherein after the addition of the chelating agent and the compound of formula I, the polyphenylene ether resin is recovered from the reaction mixture by the addition of a non-solvent.
Claim 17
Independent Claim
110 words
A method of enhancing the phase separation upon addition of water of a mixture of a polyphenylene ether reaction solvent and an antisolvent for a polyphenylnene ether reaction mixture, said method comprising adding to the polyphenylene ether reaction mixture, before addition of the antisolvent for said polyphenylene ether, of from 0.001-0.2 percent by weight of reaction mixture of a compound of the formula: ##STR9## wherein R 1 and R 2 may both be alkyl of from 6-22 carbon atoms or alkenyl of from 6-22 carbon atoms or one of R 1 and R 2 may be -(CH 2 CH 2 -O-) x H; x is an integer of from 1-40.
Claim 18
Independent Claim
110 words
A method of enhancing the phase separation upon addition of water of a mixture of a polyphenylene ether reaction solvent and an antisolvent for a polyphenylnene ether reaction mixture, said method comprising adding to the polyphenylene ether reaction mixture, before addition of the antisolvent for said polyphenylene ether, of from 0.001-0.2 percent by weight of reaction mixture of a compound of the formula: ##STR9## wherein R 1 and R 2 may both be alkyl of from 6-22 carbon atoms or alkenyl of from 6-22 carbon atoms or one of R 1 and R 2 may be -(CH 2 CH 2 -O-) x H; x is an integer of from 1-40.
Claim 19
Independent Claim
114 words
A method of carrying out the phase separation of a mixture of polyphenylene ether reaction solvent and an antisolvent, said method comprising adding to said mixture from 10 to 200 parts per million parts of polyphenylene ether reaction solvent of a compound of the formula: ##STR10## wherein R 1 and R 2 may both be alkyl of from 6-22 carbon atoms or alkenyl of from 6- 22 carbon atoms or one of R 1 and R 2 may be -(CH 2 CH 2 -O-) x H; x is an integer of from 1 to 40; adding water, then allowing the solvent and antisolvent to resolve into distinct phases and thereafter decanting the respective layers.
Claim 20
Independent Claim
114 words
A method of carrying out the phase separation of a mixture of polyphenylene ether reaction solvent and an antisolvent, said method comprising adding to said mixture from 10 to 200 parts per million parts of polyphenylene ether reaction solvent of a compound of the formula: ##STR10## wherein R 1 and R 2 may both be alkyl of from 6-22 carbon atoms or alkenyl of from 6- 22 carbon atoms or one of R 1 and R 2 may be -(CH 2 CH 2 -O-) x H; x is an integer of from 1 to 40; adding water, then allowing the solvent and antisolvent to resolve into distinct phases and thereafter decanting the respective layers.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-08-15 | 1981-02-14 | 1981-08-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-08-15 | 1985-02-14 | 1985-08-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-08-15 | 1989-02-14 | 1989-08-16 | $7700.00 | Window Closed / Lapsed |