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US4054553A
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Polyphenylene oxide process
Assignee: General Electric Co
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Filing: 1975-06-02
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Granted: 1977-10-18
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Expires: 1995-06-02
Abstract
Abstract A process of forming self-condensation products of a phenol under polymer-forming reaction conditions which comprises contacting a phenol with oxygen in the presence of a secondary aliphatic amine and an effective manganese chelate complex is described. The resulting polyphenylene oxide resins in combination with styrene resins provide thermoplastic compositions having improved impact strength.
Inventors
- 👤 Walter K. Olander
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 14:09
CPC Classifications
C; C08; C08G; C08G65/00; C08G65/34; C08G65/38; C08G65/44; C08L; C08L71/00; C08L71/08; C08L71/10; C08L71/12; C08L71/123
Claims Analysis
Total Claims: 6
Claim 1
Independent Claim
311 words
A process of forming self-condensation products of a phenol having the structural formula: ##STR4## where X is a substituent selected from the group consisting of hydrogen, chlorine, bromine, and iodine; R' is a monovalent constituent selected from the group consisting of hydrogen, hydrocarbon radicals, halohydrocarbon radicals having at least two carbon atoms between the halogen atoms and phenol nucleus, hydrocarbonoxy radicals, and halohydrocarbonoxy radicals having at least two carbon atoms between the halogen atoms and phenol nucleus, R" and R'" being the same as R' and, in addition, halogen under reaction conditions which comprise contacting said phenol with oxygen in the presence of a basic reaction medium, a secondary aliphatic amine, and a Type (A) or a mixture of Type (A) and Type (B) manganese chelate complexes selected from Type (A) complexes of the formulas: (L.sup.1).sub.x Mn , Type (A) where L 1 is a ligand derived from an ortho-hydroxyareneoxime of the general formula ##STR5## wherein R a is independently selected from the group consisting of hydrogen and lower alkyl radicals having from 1-5 carbon atoms, Ar is at least a divalent arene radical having at least one --OH radical and at least one ##STR6## radical attached directly to ortho-positioned arene ring carbon atoms, and an ω-hydroxyoxime of the formula ##STR7## wherein each R b , R c , R d and R e is independently selected from the group consisting of hydrogen, acyclic and cyclic organic radicals, and n is a positive integer equal to 0 or 1, Mn is the transition metal manganese, and x is a positive number at least equal to about 0.5, and selected from Type (B) complexes of the formula: (L.sup.2).sub.x Mn , Type (B) wherein L 2 is a ligand other than an L 1 ligand, Mn is the transition metal manganese, and x is a positive number at least equal to about 0.5.
Claim 2
Dependent Claim
311 words
A process of forming self-condensation products of a phenol having the structural formula: ##STR4## where X is a substituent selected from the group consisting of hydrogen, chlorine, bromine, and iodine; R' is a monovalent constituent selected from the group consisting of hydrogen, hydrocarbon radicals, halohydrocarbon radicals having at least two carbon atoms between the halogen atoms and phenol nucleus, hydrocarbonoxy radicals, and halohydrocarbonoxy radicals having at least two carbon atoms between the halogen atoms and phenol nucleus, R" and R'" being the same as R' and, in addition, halogen under reaction conditions which comprise contacting said phenol with oxygen in the presence of a basic reaction medium, a secondary aliphatic amine, and a Type (A) or a mixture of Type (A) and Type (B) manganese chelate complexes selected from Type (A) complexes of the formulas: (L.sup.1).sub.x Mn , Type (A) where L 1 is a ligand derived from an ortho-hydroxyareneoxime of the general formula ##STR5## wherein R a is independently selected from the group consisting of hydrogen and lower alkyl radicals having from 1-5 carbon atoms, Ar is at least a divalent arene radical having at least one --OH radical and at least one ##STR6## radical attached directly to ortho-positioned arene ring carbon atoms, and an ω-hydroxyoxime of the formula ##STR7## wherein each R b , R c , R d and R e is independently selected from the group consisting of hydrogen, acyclic and cyclic organic radicals, and n is a positive integer equal to 0 or 1, Mn is the transition metal manganese, and x is a positive number at least equal to about 0.5, and selected from Type (B) complexes of the formula: (L.sup.2).sub.x Mn , Type (B) wherein L 2 is a ligand other than an L 1 ligand, Mn is the transition metal manganese, and x is a positive number at least equal to about 0.5.
Claim 3
Dependent Claim
40 words
The process of claim 1 where the amine is of the formula HNR.sup.1 R.sup.2, where independently each R 1 and R 2 , singly or in combination, is selected from acyclic and cyclic organic radicals having from 1-30 carbon atoms.
Claim 4
Dependent Claim
94 words
The process of claim 1 where the amine is of the formula R.sup.5 --(NR.sup.3 R.sup.4).sub.y where at least one of R 3 is hydrogen, independently any other R 3 is hydrogen or the same as R 4 , when R 3 is other than hydrogen, independently R 3 and R 4 , singly or in combination, are the same as R 1 and R 2 , R 5 is an acyclic or cyclic polyvalent organic radical having from 4 to 30 carbon atoms, and y is a positive integer equal to at least 2.
Claim 5
Dependent Claim
20 words
The process of claim 1 where the secondary amine nitrogen grams to phenol mole ratio is from 0.035 to 1.000.
Claim 6
Dependent Claim
13 words
The process of claim 4, where the ratio is less than about 0.185.
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) | 1980-10-17 | 1981-04-18 | 1981-10-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-10-17 | 1985-04-18 | 1985-10-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-10-17 | 1989-04-18 | 1989-10-18 | $7700.00 | Window Closed / Lapsed |