US4252982A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Aliphatic ester solvent in esterification of carboxybenzenes
Assignee: Honeywell International Inc
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Filing: 1979-10-29
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Granted: 1981-02-24
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Expires: 1999-10-29
Abstract
Abstract An anhydride of a carboxybenzene is esterified in solution by a fluorinated alcohol, using an aliphatic ester having a boiling point between about 50 DEG C. and about 150 DEG C. as solvent. In particular, pyromellitic dianhydride is esterified in an ester such as ethyl acetate or butyl acetate to the diester/diacid by reaction with 2-(n-perfluoroalkyl)ethanols having six to twelve carbon atoms in the perfluoroalkyl groups, and the reaction mixture containing the dissolved diester/diacid is admixed with an oxirane compound of the group ethylene oxide, epichlorohydrin and glycidol whereby the carboxyl groups are esterified in the solvent by reaction with oxirane groups. The product is recovered by evaporating off the solvent and unreacted oxirane compound. The product imparts oil and/or water repellency to textiles.
Inventors
- 👤 Bryce C. Oxenrider
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 00:35
CPC Classifications
C; C07; C07C; C07C69/00; C07C69/76
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
50 words
In a process for esterification in solution of a carboxybenzene by contact of an anhydride of said carboxybenzene with a fluorinated alcohol; the improvement which comprises using a solvent consisting essentially of at least one saturated aliphatic ester having a boiling point between about 50° C. and about 150° C.
Claim 2
Dependent Claim
50 words
In a process for esterification in solution of a carboxybenzene by contact of an anhydride of said carboxybenzene with a fluorinated alcohol; the improvement which comprises using a solvent consisting essentially of at least one saturated aliphatic ester having a boiling point between about 50° C. and about 150° C.
Claim 3
Dependent Claim
36 words
Process of claim 1 wherein the alcohol is a (perfluoroalkyl)ethanol or (perfluoroalkyl)propanol having three to twelve carbon atoms in the perfluoroalkyl groups; or an (omega-perfluoroisopropoxyperfluoroalkyl)ethanol or-propanol having two to ten carbon atoms in the perfluoroalkyl groups.
Claim 4
Dependent Claim
24 words
Process of claim 2 wherein the alcohol is a mixture consisting essentially of 2-(n-perfluoroalkyl)ethanols having six to twelve carbon atoms in the perfluoroalkyl groups.
Claim 5
Dependent Claim
11 words
Process of claim 3 wherein the compound esterified is pyromellitic dianhydride.
Claim 6
Dependent Claim
82 words
In a process for esterification in solution of pyromellitic anhydride with a fluorinated alcohol to form a reaction mixture containing a diester of pyromellitic acid and reaction with an oxirane compound of the group consisting of ethylene oxide, epichlorohydrin and glycidol to esterify the remaining carboxyl groups with the epoxide groups, the improvement which comprises employing a solvent for both steps consisting essentially of at least one saturated aliphatic ester having a boiling point between about 50° C. and about 150° C.
Claim 7
Dependent Claim
82 words
In a process for esterification in solution of pyromellitic anhydride with a fluorinated alcohol to form a reaction mixture containing a diester of pyromellitic acid and reaction with an oxirane compound of the group consisting of ethylene oxide, epichlorohydrin and glycidol to esterify the remaining carboxyl groups with the epoxide groups, the improvement which comprises employing a solvent for both steps consisting essentially of at least one saturated aliphatic ester having a boiling point between about 50° C. and about 150° C.
Claim 8
Dependent Claim
12 words
Process of claim 1 or 5 wherein the solvent is ethyl acetate.
Claim 9
Dependent Claim
12 words
Process of claim 1 or 5 wherein the solvent is butyl acetate.
Claim 10
Dependent Claim
23 words
Process of claim 5 wherein the product is recovered by evaporating the solvent from the product of the reaction with the epoxide groups.
Claim 11
Dependent Claim
18 words
Process of claim 8 wherein the oxirane compound is epichlorohydrin and unreacted epichlorohydrin is evaporated with the solvent.
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) | 1984-02-24 | 1984-08-25 | 1985-02-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-02-24 | 1988-08-25 | 1989-02-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-02-24 | 1992-08-25 | 1993-02-24 | $7700.00 | Window Closed / Lapsed |