Patent US4482697A successfully refreshed from Google Patents.
US4482697A
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Process, complex and catalyst for preparation of polyphenylene oxide
Assignee: General Electric Co
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Filing: 1983-05-16
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Granted: 1984-11-13
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Expires: 2003-05-16
Abstract
Abstract Polyphenylene oxides are prepared by the oxidative coupling of monohydroxy aromatic compounds such as 2,6-xylenol in the presence of copper-halide-amine catalysts in which at least part of the amine component is an aromatic diamine such as N,N'-diphenylethylenediamine, N,N'-diphenyl-N,N'-dimethylethylenediamine, N,N'-diphenylpiperazine or N,N,N',N'-tetramethyl-o-phenylenediamine. Other amines preferably present in the catalyst are a tertiary monoamine such as dimethyl-n-butylamine and a secondary monoamine such as di-n-butylamine. These diamines are characterized by a low rate of consumption during polymerization, and the catalysts prepared therefrom are hydrolytically stable.
Inventors
- 👤 Deborah A. Haitko
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 22:16
CPC Classifications
C; C08; C08G; C08G65/00; C08G65/34; C08G65/38; C08G65/44; B; B01; B01J; B01J31/00; B01J31/16; B01J31/18; B01J31/1805; B01J2531/00; B01J2531/10; B01J2531/16
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
145 words
In a process for preparing a polyphenylene oxide which comprises oxidatively coupling a monohydroxy aromatic compound in the presence of a copper-halide-amine catlayst wherein at least one amine is a diamine, the improvement wherein said diamine has the formula ##STR4## wherein Q is a lower hydrocarbon bridging radical in which the free valence bonds are attached to adjacent carbon atoms, each of R 1 and R 2 is a hydrocarbon or substituted hydrocarbon radical containing about 1-10 carbon atoms, wherein the substitutents do not materially alter the hydrocarbon character of the radical, and each of R 3 and R 4 is hydrogen or a saturated lower aliphatic radical, or R 3 and R 4 together form a divalent saturated aliphatic radical containing 2-4 carbon atoms; one of said radicals attached to each nitrogen atom being aromatic and the balance thereof being hydrogen, aliphatic or alicyclic.
Claim 2
Dependent Claim
145 words
In a process for preparing a polyphenylene oxide which comprises oxidatively coupling a monohydroxy aromatic compound in the presence of a copper-halide-amine catlayst wherein at least one amine is a diamine, the improvement wherein said diamine has the formula ##STR4## wherein Q is a lower hydrocarbon bridging radical in which the free valence bonds are attached to adjacent carbon atoms, each of R 1 and R 2 is a hydrocarbon or substituted hydrocarbon radical containing about 1-10 carbon atoms, wherein the substitutents do not materially alter the hydrocarbon character of the radical, and each of R 3 and R 4 is hydrogen or a saturated lower aliphatic radical, or R 3 and R 4 together form a divalent saturated aliphatic radical containing 2-4 carbon atoms; one of said radicals attached to each nitrogen atom being aromatic and the balance thereof being hydrogen, aliphatic or alicyclic.
Claim 3
Dependent Claim
11 words
A process according to claim 1 wherein the halide is bromide.
Claim 4
Dependent Claim
24 words
A process according to claim 2 wherein the amine component comprises at least one tertiary monoamine, at least one secondary monoamine and said diamine.
Claim 5
Dependent Claim
24 words
A process according to claim 3 wherein the source of copper and bromide ions is a solution of cuprous oxide in aqueous hydrogen bromide.
Claim 6
Dependent Claim
43 words
A process according to claim 4 wherein the molar ratio of bromide ions to copper ions is at least about 2:1, the molar ratio of tertiary monoamine to copper is about 10-100:1 and the molar ratio of diamine to copper is about 0.4-3:1.
Claim 7
Dependent Claim
22 words
A process according to claim 5 wherein the amount of secondary monoamine is about 0.5-3 mole percent based on monohydroxy aromatic compound.
Claim 8
Dependent Claim
18 words
A process according to claim 6 wherein the tertiary monoamine is dimethyl-n-butylamine and the secondary monoamine is di-n-butylamine.
Claim 9
Dependent Claim
13 words
A process according to claim 7 wherein the monohydroxy aromatic compound is 2,6-xylenol.
Claim 10
Dependent Claim
26 words
A process according to claim 8 wherein a phase transfer agent is also present in an amount of 0.1-0.8% by weight based on monohydroxy aromatic compound.
Claim 11
Dependent Claim
26 words
A process according to claim 9 wherein the amount of catalyst is such that the mole ratio of copper to 2,6-xylenol is from 1:100 to 1:1500.
Claim 12
Dependent Claim
22 words
A process according to claim 10 wherein Q is aliphatic or alicyclic and each of R 1 and R 2 is aromatic.
Claim 13
Dependent Claim
12 words
A process according to claim 11 wherein Q is the ethylene radical.
Claim 14
Dependent Claim
16 words
A process according to claim 12 wherein each of R 1 and R 2 is phenyl.
Claim 15
Dependent Claim
16 words
A process according to claim 13 wherein each of R 3 and R 4 is hydrogen.
Claim 16
Dependent Claim
16 words
A process according to claim 13 wherein each of R 3 and R 4 is methyl.
Claim 17
Dependent Claim
17 words
A process according to claim 13 wherein R 3 and R 4 together form an ethylene radical.
Claim 18
Dependent Claim
22 words
A process according to claim 10 wherein Q is aromatic and each of R 1 and R 2 is aliphatic or alicyclic.
Claim 19
Dependent Claim
12 words
A process according to claim 17 wherein Q is the o-phenylene radical.
Claim 20
Dependent Claim
22 words
A process according to claim 18 wherein each of R 1 , R 2 , R 3 and R 4 is methyl.
Claim 21
Dependent Claim
48 words
A process according to claim 1, 3, 5, 8, 9, 12, 14, 15, 16, 18 or 19 wherein the copper and at least a portion of the halide and diamine are provided in the form of a divalent copper complex having the formula ##STR5## wherein X is halide.
Claim 22
Dependent Claim
10 words
A process according to claim 20 wherein X is bromide.
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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) | 1987-11-13 | 1988-05-14 | 1988-11-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-11-13 | 1992-05-14 | 1992-11-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-11-13 | 1996-05-14 | 1996-11-13 | $7700.00 | Window Closed / Lapsed |