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US4515640A
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Fluoroaliphatic-thio,-sulfinyl, or sulfonyl substituted bicycloaliphatic amic acid amine salts, and compositions and use thereof
Assignee: Novartis Corp
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Filing: 1983-06-13
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Granted: 1985-05-07
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Expires: 2003-06-13
Abstract
Abstract Fluoroaliphatic-thio,-sulfinyl and -sulfonyl substituted bicycloaliphatic amic acid amine salts of the formula: ##STR1## where R f is perfluoroalkyl, R' is alkylene optionally interrupted by --O--, --S-- or ##STR2## where R a is hydrogen or alkyl, Y is lower alkylene or --O--, n is 0-2, R 1 and R 2 are independently hydrogen, lower alkyl, hydroxy lower alkyl or together with the nitrogen to which they are attached, represented morpholino, R 3 , R 4 and R 5 are independently hydrogen, lower alkyl, or hydroxy lower alkyl, R 6 is lower alkyl, carboxy lower alkyl, sulfo lower alkyl, hydroxy lower alkyl, benzyl or together with R 5 and the nitrogen to which they are attached represent morpholino, and R is hydrogen or methyl are provided. These salts applied in the form of aqueous solutions, dispersions or emulsions are useful in rendering cellulosic and natural and synthetic polyamide materials oil and water repellent.
Inventors
- 👤 Jurgen Kaschig
- 👤 Eduard K. Kleiner
- 👤 Karl F. Mueller
- 👤 Thomas W. Cooke
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 16:32
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/77; C07D307/93
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
190 words
A fluoroaliphatic substituted bicycloaliphatic amic acid amine salt of the formula ##STR20## wherein R f is straight or branched chain perfluoroalkyl of 4 to 18 carbon atoms or perfluoroalkoxy-perfluoroalkyl of 4 to 18 carbon atoms; R' is straight or branched chain alkylene of 1 to 12 carbon atoms, alkylenethioalkylene of 2 to 12 carbon atoms, alkyleneoxyalkylene of 2 to 12 carbon atoms, a alkyleneiminoalkylene of 2 to 12 carbon atoms where the imino nitrogen atom contains as a third substitutent, hydrogen or alkyl of 1 to 6 carbon atoms; n is 0, 1 or 2; Y is lower alkylene or --O--; R 1 and R 2 are independently hydrogen, lower alkyl, hydroxy-lower alkyl, or together with the nitrogen to which they are attached, represent morpholino; R 3 , R 4 and R 5 independently represent hydrogen, lower alkyl, or hydroxy-lower alkyl, R 6 is lower alkyl, benzyl, lower alkyl substituted by hydroxy, carboxy or sulfo, or together with R 5 and the nitrogen to which they are attached represent morpholino; R is hydrogen or methyl; and wherein the R f --R'--S(O) n -- group is in the 5- or 6-position.
Claim 2
Dependent Claim
190 words
A fluoroaliphatic substituted bicycloaliphatic amic acid amine salt of the formula ##STR20## wherein R f is straight or branched chain perfluoroalkyl of 4 to 18 carbon atoms or perfluoroalkoxy-perfluoroalkyl of 4 to 18 carbon atoms; R' is straight or branched chain alkylene of 1 to 12 carbon atoms, alkylenethioalkylene of 2 to 12 carbon atoms, alkyleneoxyalkylene of 2 to 12 carbon atoms, a alkyleneiminoalkylene of 2 to 12 carbon atoms where the imino nitrogen atom contains as a third substitutent, hydrogen or alkyl of 1 to 6 carbon atoms; n is 0, 1 or 2; Y is lower alkylene or --O--; R 1 and R 2 are independently hydrogen, lower alkyl, hydroxy-lower alkyl, or together with the nitrogen to which they are attached, represent morpholino; R 3 , R 4 and R 5 independently represent hydrogen, lower alkyl, or hydroxy-lower alkyl, R 6 is lower alkyl, benzyl, lower alkyl substituted by hydroxy, carboxy or sulfo, or together with R 5 and the nitrogen to which they are attached represent morpholino; R is hydrogen or methyl; and wherein the R f --R'--S(O) n -- group is in the 5- or 6-position.
Claim 3
Dependent Claim
100 words
A compound according to claim 1, wherein R f is perfluoroalkyl of 6 to 14 carbon atoms, R' is alkylene of 1 to 6 carbon atoms, n is 0 or 2, Y is methylene or ethylene, R 1 is hydrogen or hydroxy-lower alkyl, R 2 is hydroxy-lower alkyl, or R 1 and R 2 taken together are morpholino, R 3 , R 4 and R 5 are independently hydrogen, lower alkyl or hydroxy-lower alkyl, R 6 is hydroxy-lower alkyl or together with R 5 and the nitrogen to which they are attached represent morpholino; and R is hydrogen or methyl.
Claim 4
Dependent Claim
29 words
A compound according to claim 1 wherein R 1 , R 2 , R 5 and R 6 are hydroxy-lower alkyl and R 3 and R 4 are hydrogen.
Claim 5
Dependent Claim
20 words
A compound according to claim 3, wherein R 1 , R 2 , R 5 and R 6 are hydroxyethyl.
Claim 6
Dependent Claim
29 words
A compound according to claim 2, wherein R 1 , R 2 , R 5 and R 6 are hydroxy-lower alkyl and R 3 and R 4 are hydrogen.
Claim 7
Dependent Claim
20 words
A compound according to claim 5 wherein R 1 , R 2 , R 5 and R 6 are hydroxyethyl.
Claim 8
Dependent Claim
95 words
A compound according to claim 1, wherein R f is 6 to 12 carbon atoms, R' is alkylene of 2 to 4 carbon atoms, n is O, Y is methylene, R 1 is hydrogen or hydroxyethyl, R 2 is hydroxyethyl, or R 1 and R 2 taken together with the nitrogen to which they are attached represent morpholino, R 3 and R 4 are hydrogen, R 5 is hydrogen or hydroxyethyl, R 6 is hydroxyethyl or taken together with R 5 and the nitrogen to which they are attached represent morpholino, and R is hydrogen.
Claim 9
Dependent Claim
20 words
A compound according to claim 7, wherein R 1 , R 2 , R 5 and R 6 are hydroxyethyl.
Claim 10
Dependent Claim
18 words
An aqueous emulsion concentrate containing 5% to 50% by weight of the amine salt according to claim 1.
Claim 11
Dependent Claim
18 words
An aqueous emulsion concentrate containing 5% to 50% by weight of the amine salt according to claim 2.
Claim 12
Dependent Claim
18 words
An aqueous emulsion concentrate containing 5% to 50% by weight of the amine salt according to claim 7.
Claim 13
Dependent Claim
77 words
An aqueous emulsion or dispersion for topical application to a cellulosic or natural or synthetic polyamide substrate, to render the substrate oil and water repellant comprising (a) 0.01 to 5% by weight of the amine salt according to claim 1; (b) 0 to 3% by weight emulsifier; (c) 0 to 5% by weight filler, water repellant assistant, bacteriostat, coloring agent or surface conditioner adjuvant; (d) 0 to 10% by weight sizing agent, and (e) the remainder water.
Claim 14
Dependent Claim
18 words
An aqueous emulsion or dispersion according to claim 12, containing 0.001 to 3% by weight of said emulsifier.
Claim 15
Dependent Claim
16 words
An aqueous emulsion or dispersion according to claim 13, wherein the emulsifier is a non-ionic emulsifier.
Claim 16
Dependent Claim
18 words
An aqueous emulsion or dispersion according to claim 12, containing 0.01 to 5% by weight of said adjuvant.
Claim 17
Dependent Claim
26 words
An aqueous emulsion or dispersion for topical application to a cellulosic substrate, according to claim 12, containing 0.01 to 10% by weight of said sizing agent.
Claim 18
Dependent Claim
66 words
An aqueous emulsion for the internal sizing of paper pulp, to render the same oil and water repellent, comprising (a) 0.0005 to 0.1% by weight of an amine salt according to claim 1; (b) 0.00001 to 0.05% by weight emulsifier; (c) 0 to 5% by weight filler, bacteriostat, fungicide, coloring agent or surface conditioner adjuvant; (d) 0 to 10% sizing agent; and (e) the remainder water.
Claim 19
Dependent Claim
13 words
An emulsion according to claim 17, wherein the emulsifier is a nonionic emulsifier.
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) | 1988-05-06 | 1988-11-05 | 1989-05-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-05-06 | 1992-11-05 | 1993-05-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-05-06 | 1996-11-05 | 1997-05-07 | $7700.00 | Window Closed / Lapsed |