Patent US4414277A successfully refreshed from Google Patents.
US4414277A
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US
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Mixtures comprising fluorinated pyromellitate oligomers useful as surfactants and processes for the production and use thereof
Assignee: Honeywell International Inc
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Filing: 1982-08-30
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Granted: 1983-11-08
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Expires: 2002-08-30
Abstract
Abstract A process for the production of oligomeric mixtures useful as surfactants is disclosed. The initial step of the process comprises reacting pyromellitic dianhydride with a fluoroalcohol using a mole ratio of about one mole pyromellitic dianhydride per two moles of fluoroalcohol to produce an intermediate which contains two fluorinated ester moieties and two free acid moieties. Thereafter, the intermediate diester-diacid is reacted with an excess of an oxirane compound such as epichlorohydrin, epibromohydrin or propylene oxide wherein said oxirane compound reacts with the free acid moieties to produce ester moieties containing a primary or secondary alcohol moiety. In the final step of the process, additional pyromellitic dianhydride is added to the reaction mixture so that the alcohol moieties may react with anhydride moieties to produce ester linking groups (between pyromellitate nuclei) and additional free acid moieties capable of reacting with the oxirane compound.
Inventors
- 👤 Bryce C. Oxenrider
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 13:08
CPC Classifications
D; D06; D06M; D06M13/00; D06M13/10; D06M13/184; D06M13/207; D06M13/21; D06M13/213; D06M13/11; D06M13/192; Y; Y10; Y10T; Y10T428/00; Y10T428/29; Y10T428/2913; Y10T428/2915; Y10T428/2933; Y10T428/2938; Y10T428/2964; Y10T428/2967; Y10T428/2969
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
158 words
A process for the production of an organic mixture useful as a fiber surface modifying agent wherein said mixture comprises oligomeric compounds and wherein said process comprises: (a) reacting pyromellitic dianhydride with fluorinated alcohol at a mole ratio of about two moles of fluorinated alcohol per mole of pyromellitic dianhydride to produce a pyromellitate having two fluorinated ester moieties and two carboxylic acid moieties; (b) reacting said pyromellitate of step (a) with an excess of an oxirane compound selected from the group consisting of epichlorohydrin, epibromohydrin, and propylene oxide in the presence of additional pyromellitic dianhydride to produce said organic mixture comprising oligomeric compounds; wherein said oxirane compounds react with said carboxylic acid moieties to produce an ester having a primary or secondary alcohol, and wherein said alcohol reacts with said additional pyromellitic dianhydride to produce ester-linking moieties and carboxylic acid moieties capable of reacting with said oxirane compound to produce additional esters having primary or secondary alcohols.
Claim 2
Dependent Claim
158 words
A process for the production of an organic mixture useful as a fiber surface modifying agent wherein said mixture comprises oligomeric compounds and wherein said process comprises: (a) reacting pyromellitic dianhydride with fluorinated alcohol at a mole ratio of about two moles of fluorinated alcohol per mole of pyromellitic dianhydride to produce a pyromellitate having two fluorinated ester moieties and two carboxylic acid moieties; (b) reacting said pyromellitate of step (a) with an excess of an oxirane compound selected from the group consisting of epichlorohydrin, epibromohydrin, and propylene oxide in the presence of additional pyromellitic dianhydride to produce said organic mixture comprising oligomeric compounds; wherein said oxirane compounds react with said carboxylic acid moieties to produce an ester having a primary or secondary alcohol, and wherein said alcohol reacts with said additional pyromellitic dianhydride to produce ester-linking moieties and carboxylic acid moieties capable of reacting with said oxirane compound to produce additional esters having primary or secondary alcohols.
Claim 3
Dependent Claim
35 words
A process according to claim 1 wherein said excess pyromellitic dianhydride is added to a reaction medium in said step (b) when about 50% to about 100% of the carboxylic acid moieties have been esterified.
Claim 4
Dependent Claim
35 words
A process according to claim 2 wherein said excess pyromellitic dianhydride is added to a reaction medium in said step (b) when about 85% to about 95% of the carboxylic acid moieties have been esterified.
Claim 5
Dependent Claim
26 words
A process according to claim 1 wherein said additional pyromellitic dianhydride is added to a reaction medium in said step (b) simultaneously with the oxirane compound.
Claim 6
Dependent Claim
40 words
The process of claim 1 or 2 or 3 or 4 wherein said fluorinated alcohol is of the formula: CF 3 (CF 2 ) p R'OH wherein R' is alkylene of 2-6 carbons and p is an integer of 3-15.
Claim 7
Dependent Claim
39 words
The process of claim 5 wherein said fluorinated alcohol is a mixture of compounds of the formula CF 3 CF 2 (CF 2 CF 2 ) n CH 2 CH 2 OH with n being from 1 to 6.
Claim 8
Dependent Claim
12 words
The process of claim 6 wherein n is from 2 to 5.
Claim 9
Dependent Claim
10 words
The process of claim 7 conducted in N-methylpyrrolidone as solvent.
Claim 10
Dependent Claim
20 words
The process of claim 7 conducted in an aliphatic ester solvent having a boiling point less than about 150° C.
Claim 11
Dependent Claim
16 words
The oligomer-containing mixture produced by the process of claims 1 or 2 or 3 or 4.
Claim 12
Dependent Claim
37 words
A method of treating a polyamide or polyester fiber which comprises applying to the fiber the oligomer-containing mixture of claim 10 and annealing the treated fiber at a temperature between about 40° C. and about 160° C.
Claim 13
Dependent Claim
20 words
The method of claim 11 wherein the annealing is conducted at a temperature between about 100° C. and 140° C.
Claim 14
Dependent Claim
12 words
A polyamide fiber having applied thereto the oligomer-containing mixture of claim 10.
Claim 15
Dependent Claim
12 words
A polyester fiber having applied thereto the oligomer-containing mixture of claim 10.
Claim 16
Dependent Claim
29 words
A process according to claim 1 or 2 or 3 or 4 wherein said step (b) is conducted at a temperature between about 20° C. and about 80° C.
Claim 17
Dependent Claim
13 words
A process according to claim 15 wherein said temperature is about 55° C.
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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) | 1986-11-07 | 1987-05-09 | 1987-11-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-11-07 | 1991-05-09 | 1991-11-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-11-07 | 1995-05-09 | 1995-11-08 | $7700.00 | Window Closed / Lapsed |