US4473371A
Expired / Lapsed
US
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Perfluoroalkyl esters, a process for their preparation and their use as a soil-repellant agent
Assignee: Hoechst AG
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Filing: 1982-08-27
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Granted: 1984-09-25
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Expires: 2002-08-27
Abstract
Abstract Perfluoroalkyl esters of the formula ##STR1## wherein R 1 denotes C 2 -C 20 , preferably C 4 -C 14 -perfluoroalkyl or perfluoroalkoxyperfluoroalkyl, R 2 denotes C 3 -C 4 -alkylene, R 3 denotes C 2 -C 5 -ω-epoxyalkyl or C 1 -C 18 , preferably C 1 -C 5 -alkyl, which can be substituted by 1 or 2 halogen atoms, preferably chlorine atoms, by hydroxyl groups, by a group of the formula ##STR2## by 1 to 3 groups of the formula --OCO--CX═CY--COO--(CH 2 ) m --R 1 or by, in each case, one lower alkoxy, epoxy, lower acyloxy, lower alkoxycarbonyl, lower acylamino, lower hydroxylalkylthio, lower trialkylamino, lower trialkylammonium, phenyl, phenoxy or furanyl group or R 3 , in the case where b=0, also denotes C 3 -C 18 -alkenyl, which can be subsituted by hydroxyl groups or a phenyl group; C 3 -C 8 -alkynyl, which can be substituted by hydroxyl groups; cyclohexyl; phenyl, which can be substituted by 1-3 C 1 -C 8 -alkyl groups or by phenyl, or naphthyl, R 4 denotes hydrogen or methyl, R 5 denotes hydrogen or C 1 -C 4 -alkyl, X and Y denote hydrogen, halogen or C 1 -C 6 -alkyl, a denotes a number from 1 to 10, b denotes 0 or 1 and m denotes a number from 1 to 6, preferably 1 to 4, a process for their preparation and their use for providing oil and water-repellant finishing of textile material.
Inventors
- 👤 Erich Schinzel
- 👤 Emmerich Paszthory
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 14:21
CPC Classifications
D; D06; D06M; D06M15/00; D06M15/19; D06M15/21; D06M15/263; D06M15/277; D06M13/00; D06M13/10; D06M13/184; D06M13/207; D06M13/21; D06M13/213
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
209 words
A perfluoroalkyl ester of the formula (1) ##STR35## wherein R 1 denotes C 2 -C 20 -perfluoroalkyl or perfluoroalkoxyperfluoroalkyl, R 2 denotes C 3 -C 4 -alkylene, R 3 denotes C 2 -C 5 -ω-epoxyalkyl or C 1 -C 18 alkyl, which can be substituted by 1 or 2 halogen atoms by hydroxyl groups, by a group of the formula ##STR36## by 1 to 3 groups of the formula --OCO--CX═CY--COO--(CH 2 ) m --R 1 or by, in each case, one lower alkoxy, epoxy, lower acyloxy, lower alkoxycarbonyl, lower acylamino, lower hydroxylalkylthio, lower trialkylamino, lower trialkylammonium, phenyl, phenoxy or furanyl group or R 3 , in the case where b=0, also denotes C 3 -C 18 -alkenyl, which can be substituted by hydroxyl groups or a phenyl group; C 3 -C 8 -alkynyl, which can be substituted by hydroxyl groups; cyclohexyl; phenyl, which can be substituted by 1-3 C 1 -C 8 -alkyl groups or by phenyl, or naphthyl, R 4 denotes hydrogen or methyl, R 5 denotes hydrogen or C 1 -C 4 -alkyl, X and Y denote hydrogen, halogen or C 1 -C 6 -alkyl, a denotes a number from 1 to 10, b denotes 0 or 1 and m denotes a number from 1 to 6.
Claim 2
Dependent Claim
209 words
A perfluoroalkyl ester of the formula (1) ##STR35## wherein R 1 denotes C 2 -C 20 -perfluoroalkyl or perfluoroalkoxyperfluoroalkyl, R 2 denotes C 3 -C 4 -alkylene, R 3 denotes C 2 -C 5 -ω-epoxyalkyl or C 1 -C 18 alkyl, which can be substituted by 1 or 2 halogen atoms by hydroxyl groups, by a group of the formula ##STR36## by 1 to 3 groups of the formula --OCO--CX═CY--COO--(CH 2 ) m --R 1 or by, in each case, one lower alkoxy, epoxy, lower acyloxy, lower alkoxycarbonyl, lower acylamino, lower hydroxylalkylthio, lower trialkylamino, lower trialkylammonium, phenyl, phenoxy or furanyl group or R 3 , in the case where b=0, also denotes C 3 -C 18 -alkenyl, which can be substituted by hydroxyl groups or a phenyl group; C 3 -C 8 -alkynyl, which can be substituted by hydroxyl groups; cyclohexyl; phenyl, which can be substituted by 1-3 C 1 -C 8 -alkyl groups or by phenyl, or naphthyl, R 4 denotes hydrogen or methyl, R 5 denotes hydrogen or C 1 -C 4 -alkyl, X and Y denote hydrogen, halogen or C 1 -C 6 -alkyl, a denotes a number from 1 to 10, b denotes 0 or 1 and m denotes a number from 1 to 6.
Claim 3
Dependent Claim
126 words
A perfluoroalkyl ester of the formula (1) as claimed in claim 1 wherein R 1 denotes a group of the formula C 1 F 21+1 -, a group of the formula H(C 2 F 4 ) n --, or a group of the formula (CF 3 ) 2 CFO(CF 2 ) o --, 1 denotes the numbers 6, 8, 10, 12 and 14, n denotes the numbers 1, 2, 3 and 4 and o denotes whole numbers from 2 to 8, b=0, X and Y denote hydrogen atoms, and R 3 denotes straightchain or branched C 2 --C 8 -alkyl, which can be substituted by hydroxyl groups, chlorine atoms, 1 to 3 groups of the formula --OCO--CX═CY--COO--(CH 2 ) m --R 1 or the epoxide group.
Claim 4
Dependent Claim
56 words
A perfluoroalkyl ester of the formula (1) as claimed in claim 1, wherein: R 1 denotes C 4 -C 14 -perfluoroalkyl or perfluoroalkoxyperfluoroalkyl; R 3 denotes said epoxyalkyl or C 1 -C 5 alkyl, which can be substituted by hydroxy groups or by one or two chlorine atoms; m denotes a number from 1 to 4.
Claim 5
Dependent Claim
22 words
A perfluoroalkyl ester of the formula (1) as claimed in claim 1, wherein X and Y denote hydrogen atoms arranged in trans-positions.
Claim 6
Dependent Claim
17 words
A perfluoroalkyl ester as claimed in claim 2, wherein X and Y denote hydrogens arranged in trans-positions.
Claim 7
Dependent Claim
101 words
A process for the preparation of a perfluoroalkyl ester of the formula (1) of claim 1 which comprises reacting 1 mole of maleic anhydride with 1 mole of a perfluorinated alcohol or alkoxyalcohol of the formula R.sub.1 --(CH.sub.2).sub.m --OH, chlorinating the thus-obtained hemiester of maleic acid, of fumaric acid, or of mixtures of these acids, and reacting the resulting acid chloride, in the presence of a base, with an alcohol of the formula ##STR37## or reacting the hemiester of maleic acid, of fumaric acid, or the mixture of said hemiesters with an epoxide, with resulting formation of a perfluoroalkyl β-hydroxyalkyl ester.
Claim 8
Dependent Claim
29 words
A method for providing oil- and water-repellant finishing of textile material comprising the step of applying a perfluoroalkyl ester of formula (1) of claim 1 to the textile material.
Claim 9
Dependent Claim
17 words
A method according to claim 7 wherein the said perfluoroalkyl ester is applied in an impregnation step.
References Cited (Backward Citations)
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1987-09-25 | 1988-03-26 | 1988-09-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-09-25 | 1992-03-26 | 1992-09-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-09-25 | 1996-03-26 | 1996-09-25 | $7700.00 | Window Closed / Lapsed |