US4446306A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Oligomer-containing mixtures useful as fiber surface treating agents and processes for the production and use thereof
Assignee: Honeywell International Inc
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Filing: 1982-05-20
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Granted: 1984-05-01
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Expires: 2002-05-20
Abstract
Abstract A reaction between pyromellitic dianhydride (PMDA) and less than two moles of fluoroalcohol produces an intermediate with ester, free acid and anhydride groups. Reaction with an oxirane compound such as epichlorohydrin reacts at the acid sites to produce pendant hydroxyls which react with anhydride on adjacent molecules to produce oligomers. Products with fluoroalcohol:PMDA ratios of, for example, about 1:0.6 to about 1:0.85 produce treated fibers with improved retention of oil repellancy, especially when annealed at 100 DEG -130 DEG C.
Inventors
- 👤 Bryce C. Oxenrider
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 23:52
CPC Classifications
D; D06; D06M; D06M13/00; D06M13/10; D06M13/184; D06M13/207; D06M13/21; D06M13/213; D06M13/11; D06M13/192
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
98 words
A process for the production of an oligomer-containing mixture useful as a fiber surface treating agent which comprises: (a) reacting pyromellitic dianhydride with fluorinated alcohol at a mole ratio of fluorinated alcohol to pyromellitic dianhydride between about 1:0.55 and about 1:1.0 to form a partially esterified product having fluorinated ester groups, free acid groups and anhydride groups; and (b) reacting the partially esterified product with an oxirane compound selected from the group consisting of epichlorohydrin, epibromohydrin and propylene oxide in an amount sufficient to cause essentially all of the free acid groups and anhydride groups to be esterified.
Claim 2
Dependent Claim
98 words
A process for the production of an oligomer-containing mixture useful as a fiber surface treating agent which comprises: (a) reacting pyromellitic dianhydride with fluorinated alcohol at a mole ratio of fluorinated alcohol to pyromellitic dianhydride between about 1:0.55 and about 1:1.0 to form a partially esterified product having fluorinated ester groups, free acid groups and anhydride groups; and (b) reacting the partially esterified product with an oxirane compound selected from the group consisting of epichlorohydrin, epibromohydrin and propylene oxide in an amount sufficient to cause essentially all of the free acid groups and anhydride groups to be esterified.
Claim 3
Dependent Claim
34 words
The process of claim 1 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 4
Dependent Claim
39 words
The process of claim 2 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 5
Dependent Claim
12 words
The process of claim 3 wherein n is from 2 to 5.
Claim 6
Dependent Claim
10 words
The process of claim 1 conducted in N-methylpyrrolidone as solvent.
Claim 7
Dependent Claim
16 words
The process of claim 1 conducted in an aliphatic ester boiling below 150° C. as solvent.
Claim 8
Dependent Claim
24 words
The process of claim 1 or 2 or 3 or 4 or 5 wherein said mole ratio is between about 1:0.6 and about 1:0.85.
Claim 9
Dependent Claim
24 words
The process of claim 1 or 2 or 3 or 4 or 5 wherein said mole ratio is between about 1:0.65 and about 1:0.75.
Claim 10
Dependent Claim
10 words
The oligomer-containing mixture produced by the process of claims 7.
Claim 11
Dependent Claim
10 words
The oligomer-containing mixture produced by the process of claim 8.
References Cited (Backward Citations)
US4209610A
Cited
US4134839A
Cited
US4192754A
Cited
US4283292A
Cited
US4190545A
Cited
US4193880A
Cited
US4321403A
Cited
US4252982A
Cited
US4329489A
Cited
US4317736A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-05-01 | 1987-10-31 | 1988-05-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-05-01 | 1991-10-31 | 1992-05-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-05-01 | 1995-10-31 | 1996-05-01 | $7700.00 | Window Closed / Lapsed |