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US4329489A Expired / Lapsed US ⏱️ 0.0 years remaining

Method of preparation of fluorocarbon compounds

Assignee: Honeywell International Inc
•
Filing: 1980-05-19
•
Granted: 1982-05-11
•
Expires: 2000-05-19
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Abstract

Abstract Preparation of a fluorocarbon compound used to make a soil-resistant yarn is improved by removing most of the impurities from the fluoro-carbon compound mass with heat and vacuum after the final washing step and then adding an emulsifier to the fluorocarbon compound mass so that the mass can be handled as a liquid concentrate rather than a tacky solid.

Inventors

  • 👤 Peter R. Saunders
  • 👤 Raymond J. Biron

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-04 07:48
CPC Classifications
C; C07; C07C; C07C233/00; C07C233/01; C07C233/16; C07C67/00; C07C67/08; C07C67/48; C07C67/62; C07C69/00; C07C69/76; D; D06; D06M; D06M13/00; D06M13/08

Claims Analysis

Total Claims: 18
Claim 1
Independent Claim 294 words
In the preparation, by the reaction of a perfluoroalkylethanol and pyromellitic dianhydride and subsequent conversion of pendent carboxyl groups to the alkyl ester-(CO 2 B) r , of a fluorocarbon compound having the formula ##STR4## wherein the attachment of the fluorinated radicals and the radicals CO 2 B to the nucleus is in asymmetrical positions with respect to rotation about the axis through the center of the nucleus wherein "X" is fluorine, or perfluoroalkoxy of 1 to 6 carbon atoms, and m has arithmetic mean between 2 and 20; n is zero or unity; "W" and "Y" are alkylene, cycloalkylene or alkyleneoxy radicals of combined chain length from 2 to 20 atoms; (CF 2 ) m and "Y" have each at least 2 carbon atoms in the main chain; "Z" is oxygen and p is 1, or "Z" is nitrogen and p is 2; q is an integer of at least 2 but not greater than 5; "B" is CH 2 RCHOH or is CH 2 RCHOCH 2 RCHOH where "R" is hydrogen or methyl, or "B" is CH 2 CH(OH)CH 2 Q where Q is halogen, hydroxy, or nitrile; or " B" is CH 2 CH(OH)CH 2 OCH 2 CH(OH)CH 2 Q; and r is an integer of at least 1 but not greater than q; and X(CF 2 ) m , W and Y are straight chains, branched chains or cyclic; and wherein the substituent chains of the above general formulas are the same or different, the improvement comprising removing most of the impurities from the fluorocarbon mass with heat and vacuum after the final washing step, then adding an emulsifier to the fluorocarbon compound mass so that the mass can be handled as a liquid concentrate rather than a tacky solid.
Claim 2
Dependent Claim 294 words
In the preparation, by the reaction of a perfluoroalkylethanol and pyromellitic dianhydride and subsequent conversion of pendent carboxyl groups to the alkyl ester-(CO 2 B) r , of a fluorocarbon compound having the formula ##STR4## wherein the attachment of the fluorinated radicals and the radicals CO 2 B to the nucleus is in asymmetrical positions with respect to rotation about the axis through the center of the nucleus wherein "X" is fluorine, or perfluoroalkoxy of 1 to 6 carbon atoms, and m has arithmetic mean between 2 and 20; n is zero or unity; "W" and "Y" are alkylene, cycloalkylene or alkyleneoxy radicals of combined chain length from 2 to 20 atoms; (CF 2 ) m and "Y" have each at least 2 carbon atoms in the main chain; "Z" is oxygen and p is 1, or "Z" is nitrogen and p is 2; q is an integer of at least 2 but not greater than 5; "B" is CH 2 RCHOH or is CH 2 RCHOCH 2 RCHOH where "R" is hydrogen or methyl, or "B" is CH 2 CH(OH)CH 2 Q where Q is halogen, hydroxy, or nitrile; or " B" is CH 2 CH(OH)CH 2 OCH 2 CH(OH)CH 2 Q; and r is an integer of at least 1 but not greater than q; and X(CF 2 ) m , W and Y are straight chains, branched chains or cyclic; and wherein the substituent chains of the above general formulas are the same or different, the improvement comprising removing most of the impurities from the fluorocarbon mass with heat and vacuum after the final washing step, then adding an emulsifier to the fluorocarbon compound mass so that the mass can be handled as a liquid concentrate rather than a tacky solid.
Claim 3
Dependent Claim 47 words
The preparation of claim 1 wherein the emulsifier is a solution consisting essentially of about 40 to 90 percent by weight of a salt of dioctyl sulfosuccinate, about 5 to 30 percent by weight of propylene glycol and about 5 to 30 percent by weight of water.
Claim 4
Dependent Claim 23 words
In the preparation of the fluorocarbon compound of claim 1 wherein the fluorocarbon compound is a mixture of pyromellitates having the structure: ##STR5##
Claim 5
Dependent Claim 39 words
The preparation of claim 3 wherein the emulsifier is a solution consisting essentially of about 70 percent by weight of sodium dioctyl sulfosuccinate, about 16 percent by weight of propylene glycol and about 14 percent by weight of water.
Claim 6
Dependent Claim 13 words
The preparation of claim 3 wherein the impurities are water, solvent and epichlorohydrin.
Claim 7
Dependent Claim 10 words
The preparation of claim 5 wherein the solvent is N-methylpyrrolidone.
Claim 8
Dependent Claim 10 words
The preparation of claim 5 wherein the solvent is dimethylformamide.
Claim 9
Dependent Claim 23 words
The preparation of claim 5 wherein the solvent is a saturated aliphatic ester having a boiling point between about 50° and 150° C.
Claim 10
Dependent Claim 31 words
The preparation of claim 1 wherein the heat is at a temperature from about 60° to about 150° C. and the vacuum is between about one Torr to seven hundred Torr.
Claim 11
Dependent Claim 15 words
The preparation of claim 1 wherein the temperature is between about 90° to 110° C.
Claim 12
Dependent Claim 15 words
The preparation of claim 1 wherein the vacuum is from between 5 to 200 Torr.
Claim 13
Dependent Claim 23 words
The preparation of claim 1 wherein the application of heat and vacuum is sufficient to lower the water content to below 1.5 percent.
Claim 14
Dependent Claim 17 words
The preparation of claim 12 wherein the water content is reduced to below one percent by weight.
Claim 15
Dependent Claim 61 words
The preparation of claim 13 wherein the molten mass of the fluorocarbon compound is allowed to cool to 75° to 95° C. and the emulsifier is added to the molten mass of fluorocarbon compound at a ratio of about 10 to 4 parts fluorocarbon compound to emulsifier by weight by stirring at 75° to 95° C. for 0.5 to 1 hour.
Claim 16
Dependent Claim 47 words
The preparation of claim 14 wherein the emulsifier is a solution consisting essentially of about 40 to 90 percent by weight of a salt of dioctyl sulfosuccinate, about 5 to 30 percent by weight of propylene glycol and about 5 to 30 percent by weight of water.
Claim 17
Dependent Claim 20 words
In the preparation of the fluorocarbon compound of claim 1, wherein the fluorocarbon compound is bis(perfluoroalkylethyl)-bis-(2-hydroxy-3-chloropropyl)-tetraester of pyromellitic acid (DSR).
Claim 18
Dependent Claim 36 words
The preparation of claim 16 wherein the emulsifier used is the same emulsifier used for adding the DSR to a spin finish for application to synthetic filaments during spinning of the molten synthetic polymer into filaments.

References Cited (Backward Citations)

US2921957A Cited
US3004061A Cited
US4193880A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1985-05-10 1985-11-09 1986-05-11 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1989-05-10 1989-11-09 1990-05-11 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1993-05-10 1993-11-09 1994-05-11 $7700.00 Window Closed / Lapsed

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