US4358624A
Expired / Lapsed
US
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Fluorinated monophenols and diphenols and method for their preparation
Assignee: General Electric Co
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Filing: 1980-12-31
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Granted: 1982-11-09
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Expires: 2000-12-31
Abstract
Abstract Phenol reactants and fluorinated aldehydes or fluorinated ketones are reacted in the presence of organic sulfonic acid catalysts to yield fluorinated monophenols and fluorinated diphenols. Fluorinated monophenols can be isolated and reacted with additional phenol reactant in the presence of organic sulfonic acid catalysts to yield asymmetrical, as well as symmetrical, fluorinated diphenols. A preferred organic sulfonic acid catalyst is methanesulfonic acid. The novel fluorinated monophenols have a hydroxy group and a fluorinated aryl radical or fluorinated alkyl radical substituted upon the benzylic carbon atom. The novel fluorinated diphenols have at least one fluorinated aryl radical or fluorinated alkyl radical substituted upon the methylene carbon atom of the bisphenol.
Inventors
- 👤 Victor Mark
- 👤 Charles V. Hedges
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 10:23
CPC Classifications
C; C07; C07C; C07C37/00; C07C37/11; C07C37/20; C07C37/115; C07C37/16; C07C39/00; C07C39/24; C07C39/26; C07C39/367
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
73 words
A fluorinated monophenol having the general formula: ##STR13## wherein Y 1 and Y 2 are each independently selected from the group consisting of hydrogen, chlorine, bromine and alkyl radical having from 1 to about 4 carbon atoms; R is selected from the group consisting of fluorinated alkyl radical and fluorinated aryl radical; and R' is selected from the group consisting of fluorinated alkyl radical, fluorinated aryl radical, alkyl radical, aryl radical and hydrogen.
Claim 2
Dependent Claim
73 words
A fluorinated monophenol having the general formula: ##STR13## wherein Y 1 and Y 2 are each independently selected from the group consisting of hydrogen, chlorine, bromine and alkyl radical having from 1 to about 4 carbon atoms; R is selected from the group consisting of fluorinated alkyl radical and fluorinated aryl radical; and R' is selected from the group consisting of fluorinated alkyl radical, fluorinated aryl radical, alkyl radical, aryl radical and hydrogen.
Claim 3
Dependent Claim
21 words
The fluorinated monophenol of claim 1 wherein R is a fluorinated alkyl radical having from 1 to about 22 carbon atoms.
Claim 4
Dependent Claim
21 words
The fluorinated monophenol of claim 1 wherein R' is a fluorinated alkyl radical having from 1 to about 22 carbon atoms.
Claim 5
Dependent Claim
21 words
The fluorinated monophenol of claim 1 wherein R is a fluorinated aryl radical having from 6 to about 16 carbon atoms.
Claim 6
Dependent Claim
21 words
The fluorinated monophenol of claim 1 wherein R' is a fluorinated aryl radical having from 6 to about 16 carbon atoms.
Claim 7
Dependent Claim
20 words
The fluorinated monophenol of claim 1 wherein R' is an alkyl radical having from 1 to about 22 carbon atoms.
Claim 8
Dependent Claim
20 words
The fluorinated monophenol of claim 1 wherein R' is an aryl radical having from 6 to about 16 carbon atoms.
Claim 9
Dependent Claim
16 words
The fluorinated monophenol of claims 1, 2, or 3 wherein the fluorinated alkyl radical is perfluorinated.
Claim 10
Dependent Claim
16 words
The fluorinated monophenol of claims 1, 4, or 5 wherein the fluorinated aryl radical is perfluorinated.
Claim 11
Dependent Claim
10 words
The fluorinated monophenol of claim 1 wherein R' is hydrogen.
Claim 12
Dependent Claim
143 words
A fluorinated diphenol having the general formula: ##STR14## wherein R is selected from the group consisting of fluorinated alkyl radical and fluorinated aryl radical; R' is selected from the group consisting of fluorinated alkyl radical, fluorinated aryl radical, alkyl radical, aryl radical and hydrogen; and Y 1 , Y 2 , Y 3 and Y 4 are substituted upon the respective phenol groups and are each independently selected from the group consisting of hydrogen, chlorine, bromine and alkyl radical having from 1 to about 4 carbon atoms; with the proviso that when R and R' are both fluorinated alkyl radical, and when R is fluorinated alkyl radical and R' is hydrogen, the phenol group having Y 1 and Y 2 thereon, differs from the phenol group having Y 3 and Y 4 thereon, and thereby forms a fluorinated diphenol having asymmetrical phenol groups.
Claim 13
Dependent Claim
143 words
A fluorinated diphenol having the general formula: ##STR14## wherein R is selected from the group consisting of fluorinated alkyl radical and fluorinated aryl radical; R' is selected from the group consisting of fluorinated alkyl radical, fluorinated aryl radical, alkyl radical, aryl radical and hydrogen; and Y 1 , Y 2 , Y 3 and Y 4 are substituted upon the respective phenol groups and are each independently selected from the group consisting of hydrogen, chlorine, bromine and alkyl radical having from 1 to about 4 carbon atoms; with the proviso that when R and R' are both fluorinated alkyl radical, and when R is fluorinated alkyl radical and R' is hydrogen, the phenol group having Y 1 and Y 2 thereon, differs from the phenol group having Y 3 and Y 4 thereon, and thereby forms a fluorinated diphenol having asymmetrical phenol groups.
Claim 14
Dependent Claim
21 words
The fluorinated diphenol of claim 11 wherein R is a fluorinated alkyl radical having from 1 to about 22 carbon atoms.
Claim 15
Dependent Claim
21 words
The fluorinated diphenol of claim 11 wherein R' is a fluorinated alkyl radical having from 1 to about 22 carbon atoms.
Claim 16
Dependent Claim
21 words
The fluorinated diphenol of claim 11 wherein R is a fluorinated aryl radical having from 6 to about 16 carbon atoms.
Claim 17
Dependent Claim
21 words
The fluorinated diphenol of claim 11 wherein R' is a fluorinated aryl radical having from 6 to about 16 carbon atoms.
Claim 18
Dependent Claim
20 words
The fluorinated diphenol of claim 11 wherein R' is an alkyl radical having from 1 to about 22 carbon atoms.
Claim 19
Dependent Claim
20 words
The fluorinated diphenol of claim 11 wherein R' is an aryl radical having from 6 to about 16 carbon atoms.
Claim 20
Dependent Claim
16 words
The fluorinated diphenol of claims 11, 12 or 13 wherein the fluorinated alkyl radical is perfluorinated.
Claim 21
Dependent Claim
16 words
The fluorinated diphenol of claims 11, 14 or 15 wherein the fluorinated aryl radical is perfluorinated.
Claim 22
Dependent Claim
39 words
The fluorinated diphenol of claim 11 wherein the phenol group having Y 1 and Y 2 thereon, differs from the phenol group having Y 3 and Y 4 thereon, and thereby forms a fluorinated diphenol having asymmetrical phenol groups.
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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) | 1985-11-08 | 1986-05-10 | 1986-11-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-11-08 | 1990-05-10 | 1990-11-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-11-08 | 1994-05-10 | 1994-11-09 | $7700.00 | Window Closed / Lapsed |