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US4295976A
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Fluorinated anti-stain and soil release finishes
Assignee: Produits Chimiques Ugine Kuhlmann
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Filing: 1976-09-28
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Granted: 1981-10-20
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Expires: 1996-09-28
Abstract
Abstract New fluorinated telomerization products are disclosed which are products produced by the reaction of: a. one mole of an ester of one or more acids of the formula HS-A(COOH)n (I) with one or more polyols, and b. 1 to 5 moles of one or more compounds possessing at least one ethylenic bond, one at least of these compounds conforming to the general formula <IMAGE> (II) In formulae (I) and (II), A represents a hydrocarbon radical which may contain atoms of oxygen, nitrogen, phosphorus, sulphur or halogen, n is a whole number from 1 to 4, Rf is a perfluorinated chain containing 1 to 20 carbon atoms, B is a bivalent chain, one of the symbols R represents a hydrogen atom and the other a hydrogen atom or an alkyl group containing 1 to 4 carbon atoms. These products when applied to substrates, such as textile fabrics, confer on them a permanent anti-stain and soil release finish while permitting easy elimination of soil by washing.
Inventors
- 👤 Andre L. Dessaint
- 👤 Jean Perronin
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 22:12
CPC Classifications
D; D06; D06M; D06M15/00; D06M15/19; D06M15/21; D06M15/244; C; C08; C08G; C08G65/00; C08G65/02; C08G65/32; C08G65/329; C08G65/334; C08G65/3342; D06M13/00; D06M13/244; D06M13/248; D06M13/252; D06M15/263; D06M15/277; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/3154; Y10T442/00; Y10T442/20; Y10T442/2164; Y10T442/2172
Claims Analysis
Total Claims: 35
Claim 1
Independent Claim
206 words
A fluorinated telomerization product consisting of the reaction product of: (a) one mole of an ester of one or more polyols with one or more acids of the general formula: HS--A(COOH).sub.n (I) wherein A represents an aliphatic or cyclic hydrocarbon radical and n is a whole number from 1 to 4, and (b) 1 to 5 moles of one or more compounds possessing at least one ethylene bond, at least one of these compounds corresponding to the general formula: ##STR17## wherein Rf represents a perfluorinated chain, straight or branched, containing 1 to 20 carbon atoms, one of the sybmols R is hydrogen and the other is hydrogen or alkyl containing 1 to 4 carbon atoms; and Rf--B--is a residue selected from the group consisting of the residues of following formulae: ##STR18## wherein x is a whole number between 1 and 20; y is a whole number from 1 to 4; z is a whole number from 1 to 10; R' is hydrogen, alkyl with 1 to 10 carbon atoms, cycloalkyl with 5 to 12 carbon atoms or hydroxyalkyl with 2 to 4 carbon atoms; R", R''', X and X' are the same or different and each represents hydrogen or alkyl with 1 to 4 carbon atoms.
Claim 2
Dependent Claim
206 words
A fluorinated telomerization product consisting of the reaction product of: (a) one mole of an ester of one or more polyols with one or more acids of the general formula: HS--A(COOH).sub.n (I) wherein A represents an aliphatic or cyclic hydrocarbon radical and n is a whole number from 1 to 4, and (b) 1 to 5 moles of one or more compounds possessing at least one ethylene bond, at least one of these compounds corresponding to the general formula: ##STR17## wherein Rf represents a perfluorinated chain, straight or branched, containing 1 to 20 carbon atoms, one of the sybmols R is hydrogen and the other is hydrogen or alkyl containing 1 to 4 carbon atoms; and Rf--B--is a residue selected from the group consisting of the residues of following formulae: ##STR18## wherein x is a whole number between 1 and 20; y is a whole number from 1 to 4; z is a whole number from 1 to 10; R' is hydrogen, alkyl with 1 to 10 carbon atoms, cycloalkyl with 5 to 12 carbon atoms or hydroxyalkyl with 2 to 4 carbon atoms; R", R''', X and X' are the same or different and each represents hydrogen or alkyl with 1 to 4 carbon atoms.
Claim 3
Dependent Claim
17 words
A fluorinated product according to claim 1 in which the acid of formula (I) is thioglycollic acid.
Claim 4
Dependent Claim
19 words
A fluorinated product according to claim 2 obtained by starting from a monoester of thioglycollic acid with a polyol.
Claim 5
Dependent Claim
19 words
A fluorinated product according to claim 2 obtained by starting with a diester of thioglycollic acid with a polyol.
Claim 6
Dependent Claim
15 words
A fluorinated product according to claim 1 in which the polyol is a poly(oxyalkylene) glycol.
Claim 7
Dependent Claim
26 words
A fluorinated product according to claim 1 in which the polyol is a condensate of the alkylene oxide with a polyol, an amine or an aminoalcohol.
Claim 8
Dependent Claim
16 words
A fluorinated product according to claim 1 in which Rf contains 2 to 10 carbon atoms.
Claim 9
Dependent Claim
20 words
A fluorinated product according to claim 1 in which x is 2 or 4 and y is 1 or 2.
Claim 10
Dependent Claim
14 words
A fluorinated product according to claim 1 in which both R are hydrogen atoms.
Claim 11
Dependent Claim
140 words
A fluorinated telomerization product consisting of the reaction product of: (a) one mole of an ester of thioglycolic acid with one or more polyols, and (b) 1 to 5 moles of one or more compounds of the formula: ##STR19## wherein Rf represents a perfluorinated chain, straight or branched, containing 1 to 20 carbon atoms; one of the symbols R is hydrogen and the other is hydrogen or alkyl containing 1 to 4 carbon atoms; x is a whole number between 1 and 20; y is a whole number from 1 to 4; R' is hydrogen, alkyl with 1 to 20 carbon atoms, cycloalkyl with 5 to 12 carbon atoms or hydroxyalkyl with 2 to 4 carbon atoms; and R", R''', X and X' are the same or different and each represents hydrogen or alkyl with 1 to 4 carbon atoms.
Claim 12
Dependent Claim
140 words
A fluorinated telomerization product consisting of the reaction product of: (a) one mole of an ester of thioglycolic acid with one or more polyols, and (b) 1 to 5 moles of one or more compounds of the formula: ##STR19## wherein Rf represents a perfluorinated chain, straight or branched, containing 1 to 20 carbon atoms; one of the symbols R is hydrogen and the other is hydrogen or alkyl containing 1 to 4 carbon atoms; x is a whole number between 1 and 20; y is a whole number from 1 to 4; R' is hydrogen, alkyl with 1 to 20 carbon atoms, cycloalkyl with 5 to 12 carbon atoms or hydroxyalkyl with 2 to 4 carbon atoms; and R", R''', X and X' are the same or different and each represents hydrogen or alkyl with 1 to 4 carbon atoms.
Claim 13
Dependent Claim
29 words
A composition for treating a surface to render said surface stain resistant comprising an effective amount of a fluorinated product as defined in claim 1 in a liquid medium.
Claim 14
Dependent Claim
30 words
A composition for treating a textile to render said textile resistant to soiling comprising an effective amount of a fluorinated product as defined in claim 1 in a solvent medium.
Claim 15
Dependent Claim
28 words
A composition for treating a surface to render the surface oil and water repellant comprising a fluorinated product as defined in claim 1 in an inert vehicle therefore.
Claim 16
Dependent Claim
134 words
A process for the preparation of fluorinated telomerization product comprising reacting one mole of an ester of one or more polyols with one or more acids of the general formula HS--A(COOH).sub.n where A represents an aliphatic or cyclic hydrocarbon radical which may contain atoms of oxygen, nitrogen, sulphur or halogen and n is a whole number from 1 to 4, and 1 to 5 moles of one or more compounds possessing at least one ethylene bond, at least one of these compounds corresponding to the general formula ##STR20## where Rf represents a perfluorinated chain, straight or branched, containing 1 to 20 carbon atoms, B is a bivalent chain, one of the symbols R is a hydrogen atom and the other is a hydrogen atom or an alkyl group containing 1 to 4 carbon atoms.
Claim 17
Dependent Claim
134 words
A process for the preparation of fluorinated telomerization product comprising reacting one mole of an ester of one or more polyols with one or more acids of the general formula HS--A(COOH).sub.n where A represents an aliphatic or cyclic hydrocarbon radical which may contain atoms of oxygen, nitrogen, sulphur or halogen and n is a whole number from 1 to 4, and 1 to 5 moles of one or more compounds possessing at least one ethylene bond, at least one of these compounds corresponding to the general formula ##STR20## where Rf represents a perfluorinated chain, straight or branched, containing 1 to 20 carbon atoms, B is a bivalent chain, one of the symbols R is a hydrogen atom and the other is a hydrogen atom or an alkyl group containing 1 to 4 carbon atoms.
Claim 18
Dependent Claim
17 words
The process of claim 14 wherein the reaction is carried out in the presence of a catalyst.
Claim 19
Dependent Claim
31 words
A process according to claim 14 wherein the reaction is carried out in the presence of 0.01 to 5% of catalyst in relation to the weight of the ethylenic compound used.
Claim 20
Dependent Claim
29 words
A process according to claim 14 wherein the reaction is carried out at a pH between 2 and 11 inclusive and at a temperature between 40 and 120° C.
Claim 21
Dependent Claim
33 words
A method for the treatment of fabrics to render said fabric oil repellant and water repellant comprising applying to said fabrics a continuous coating of a fluorinated compound as defined in claim 1.
Claim 22
Dependent Claim
33 words
A method for the treatment of paper to render said paper oil repellant and water repellant comprising applying to said paper a continuous coating of a fluorinated compound as defined in claim 1.
Claim 23
Dependent Claim
33 words
A method for the treatment of wood to render said wood oil repellant and water repellant comprising applying to said wood a continuous coating of a fluorinated compound as defined in claim 1.
Claim 24
Dependent Claim
33 words
A method for the treatment of leather to render said leather oil repellant and water repellant comprising applying to said leather a continuous coating of a fluorinated compound as defined in claim 1.
Claim 25
Dependent Claim
32 words
A method for the treatment of metal to render said metal oil repellant and water repellant comprising applying to said metal a continuous coating of a fluorinated compound as defined claim 1.
Claim 26
Dependent Claim
33 words
A method for the treatment of masonry to render said masonry oil repellant and water repellant comprising applying to said masonry a continuous coating of a fluorinated compound as defined in claim 1.
Claim 27
Dependent Claim
33 words
A method for the treatment of glass to render said glass oil repellant and water repellant comprising applying to said glass a continuous coating of a fluorinated compound as defined in claim 1.
Claim 28
Dependent Claim
33 words
A method for the treatment of porcelain to render said porcelain oil repellant and water repellant comprising applying to said porcelain a continuous coating of a fluorinated compound as defined in claim 1.
Claim 29
Dependent Claim
33 words
A method for the treatment of plastic to render said plastic oil repellant and water repellant comprising applying to said plastic a continuous coating of a fluorinated compound as defined in claim 1.
Claim 30
Dependent Claim
36 words
A method for the treatment of painted surface to render said painted surface oil repellant and water repellant comprising applying to said painted surface a continuous coating of a fluorinated compound as defined in claim 1.
Claim 31
Dependent Claim
33 words
A method for the treatment of cardboard to render said cardboard oil repellant and water repellant comprising applying to said cardboard a continuous coating of a fluorinated compound as defined in claim 1.
Claim 32
Dependent Claim
13 words
The process of claim 14 wherein Rf contains 2 to 10 carbon atoms.
Claim 33
Dependent Claim
24 words
The process of claim 16 wherein the amount of catalyst is 0.1 to 1.5% in relation to the weight of the ethylenic compound used.
Claim 34
Dependent Claim
15 words
The process of claim 17 wherein the reaction temperature is between 50° and 90° C.
Claim 35
Dependent Claim
16 words
A surface having applied thereto a coating of a fluorinated compound as defined in claim 1.
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) | 1984-10-19 | 1985-04-20 | 1985-10-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-10-19 | 1989-04-20 | 1989-10-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-10-19 | 1993-04-20 | 1993-10-20 | $7700.00 | Window Closed / Lapsed |