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US4366299A Expired / Lapsed US ⏱️ 0.0 years remaining

Copolymers containing fluorine and their use for the water-repellent and oil-repellent treatment of various substrates

Assignee: Produits Chimiques Ugine Kuhlmann
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Filing: 1981-01-27
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Granted: 1982-12-28
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Expires: 2001-01-27
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Abstract

Abstract The invention relates to fluorinated copolymers and their application to the waterproofing and oil-resistance treatment of various substrates. These copolymers comprise by weight: (a) 35 to 98% of a monomer or monomers of the formula: <IMAGE> in which Rf is a perfluoro radical, Q is an oxygen or sulfur atom, B is a bivalent chain linked to Q by a carbon atom, one of the symbols R is a hydrogen atom and the other a hydrogen atom or an alkyl radical: (b) 1 to 15% of a monomer or monomers of the formula: <IMAGE> in which B' is an alkylene radical, R' is a hydrogen atom or an alkyl radical, R1 is an alkyl, hydroxyethyl or benzyl radical, R2 is a hydrogen atom or an alkyl, hydroxyethyl or benzyl radical or R1 and R2, together with the nitrogen atom, form a heterocyclic radical: (c) 1 to 50% of a monomer or monomers of the formula: <IMAGE> (III) in which R3, R'3, R4 and R5 are hydrogen atoms or alkyl radicals; and possibly (d) up to 10% of any other monomer. These copolymers are particularly well adapted to the waterproofing and oil-proofing of paper and similar articles.

Inventors

  • 👤 Andre L. Dessaint

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-24 13:23
CPC Classifications
D; D21; D21H; D21H21/00; D21H21/14; D21H21/16; C; C08; C08F; C08F220/00; C08F220/02; C08F220/10; C08F220/22; C08F220/24; D06; D06M; D06M15/00; D06M15/19; D06M15/21; D06M15/263; D06M15/277; D21H17/00; D21H17/20; D21H17/33; D21H17/34; D21H17/37; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/3154; Y10T428/31544

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 425 words
A fluorinated copolymer which comprises: (a) 35 to 98% by weight of one or more polyfluorinated monomers of the formula: ##STR17## in which Rf represents perfluoroalkyl with a straight or branched chain containing 2 to 20 carbon atoms, Q represents oxygen or sulfur, B represents a bivalent chain selected from: ##STR18## --(CH 2 ) p --, --(CH 2 ) p --O--(CH 2 ) r --, --(CH 2 ) p --S--(CH 2 ) r --, --(CH 2 ) p --(OCH 2 CH 2 ) r --, --(CH 2 ) p --SO 2 --(CH 2 ) r --, --CH═CH--(CH 2 ) p --, ##STR19## --COO--(CH 2 ) p -- or ##STR20## in which p is a whole number from 1 to 20, q is a whole number from 1 to 4, r is a whole number from 1 to 20, R 6 is hydrogen, alkyl containing 1 to 10 carbon atoms, cycloalkyl containing 5 to 12 carbon atoms, hydroxyalkyl containing 2 to 4 carbon atoms, aryl or aryl substituted by alkyl containing 1 to 6 carbon atoms, R 7 is hydrogen or alkyl containing 1 to 4 carbon atoms, X, X', Y and Y' are the same or different and each represents hydrogen or alkyl containing 1 to 4 carbon atoms, one of the symbols R represents hydrogen and the other hydrogen or alkyl containing 1 to 4 carbon atoms; (b) 1 to 15% by weight of one or more monomers of the formula: ##STR21## in which B' represents linear or branched alkylene containing 1 to 4 carbon atoms, R' represents hydrogen or alkyl containing 1 to 4 carbon atoms, R 1 represents alkyl containing 1 to 18 carbon atoms, hydroxyethyl or benzyl, R 2 represents hydrogen or alkyl containing 1 to 18 carbon atoms, hydroxyethyl or benzyl or R 1 and R 2 together with the nitrogen form morpholino, piperidino or pyrrolidinyl-1; (c) 1 to 50% by weight of one or more pyrrolidone monomers of the formula: ##STR22## in which R 3 , R' 3 , R 4 and R 5 are the same or different and each represents hydrogen or alkyl containing 1 to 4 carbon atoms; and (d) up to 10% by weight of a monomer other than the monomers of formulae (I), (II) and (III), which is copolymerizable with said monomers of formulae (I), (II) and (III), and, optionally, its salt form obtained by salifying with an acid having a dissociation constant or first dissociation constant greater than 10 -5 , or its form obtained by quaternizing by means of a quaternizing agent.
Claim 2
Dependent Claim 425 words
A fluorinated copolymer which comprises: (a) 35 to 98% by weight of one or more polyfluorinated monomers of the formula: ##STR17## in which Rf represents perfluoroalkyl with a straight or branched chain containing 2 to 20 carbon atoms, Q represents oxygen or sulfur, B represents a bivalent chain selected from: ##STR18## --(CH 2 ) p --, --(CH 2 ) p --O--(CH 2 ) r --, --(CH 2 ) p --S--(CH 2 ) r --, --(CH 2 ) p --(OCH 2 CH 2 ) r --, --(CH 2 ) p --SO 2 --(CH 2 ) r --, --CH═CH--(CH 2 ) p --, ##STR19## --COO--(CH 2 ) p -- or ##STR20## in which p is a whole number from 1 to 20, q is a whole number from 1 to 4, r is a whole number from 1 to 20, R 6 is hydrogen, alkyl containing 1 to 10 carbon atoms, cycloalkyl containing 5 to 12 carbon atoms, hydroxyalkyl containing 2 to 4 carbon atoms, aryl or aryl substituted by alkyl containing 1 to 6 carbon atoms, R 7 is hydrogen or alkyl containing 1 to 4 carbon atoms, X, X', Y and Y' are the same or different and each represents hydrogen or alkyl containing 1 to 4 carbon atoms, one of the symbols R represents hydrogen and the other hydrogen or alkyl containing 1 to 4 carbon atoms; (b) 1 to 15% by weight of one or more monomers of the formula: ##STR21## in which B' represents linear or branched alkylene containing 1 to 4 carbon atoms, R' represents hydrogen or alkyl containing 1 to 4 carbon atoms, R 1 represents alkyl containing 1 to 18 carbon atoms, hydroxyethyl or benzyl, R 2 represents hydrogen or alkyl containing 1 to 18 carbon atoms, hydroxyethyl or benzyl or R 1 and R 2 together with the nitrogen form morpholino, piperidino or pyrrolidinyl-1; (c) 1 to 50% by weight of one or more pyrrolidone monomers of the formula: ##STR22## in which R 3 , R' 3 , R 4 and R 5 are the same or different and each represents hydrogen or alkyl containing 1 to 4 carbon atoms; and (d) up to 10% by weight of a monomer other than the monomers of formulae (I), (II) and (III), which is copolymerizable with said monomers of formulae (I), (II) and (III), and, optionally, its salt form obtained by salifying with an acid having a dissociation constant or first dissociation constant greater than 10 -5 , or its form obtained by quaternizing by means of a quaternizing agent.
Claim 3
Dependent Claim 56 words
A copolymer according to claim 1 comprising 69 to 93% by weight of one or more polyfluorinated monomers of formula (I), 5 to 11% by weight of one or more monomers of formula (II), 2 to 20% by weight of one or more monomers of formula (III), and 0 to 5% by weight of another monomer.
Claim 4
Dependent Claim 20 words
A copolymer according to claim 2 comprising 7 to 10% by weight of one or more monomers of formula (II).
Claim 5
Dependent Claim 18 words
A copolymer according to claim 1, 2 or 3 in which the monomer of formula (III) is N-vinyl-2-pyrrolidone.
Claim 6
Dependent Claim 108 words
A copolymer according to claim 4 in which the polyfluoro monomer or monomers have the formula: ##STR23## in which Rf and R have the same significance as in claim 1, p represents a whole number from 1 to 20, q represents a whole number from 1 to 4, R 6 represents hydrogen or alkyl containing 1 to 10 carbon atoms, cycloalkyl containing 5 to 12 carbon atoms, hydroxyalkyl containing 2 to 4 carbon atoms, aryl or aryl substituted by alkyl containing 1 to 6 carbon atoms, X, X', Y and Y' are the same or different and each represents hydrogen or alkyl containing 1 to 4 carbon atoms.
Claim 7
Dependent Claim 19 words
A copolymer according to claim 5 obtained from a mixture of monomers of formula (IV) having different Rf radicals.
Claim 8
Dependent Claim 16 words
A copolymer according to claim 6 in which the monomer of formula (II) is dimethylaminoethyl methacrylate.
Claim 9
Dependent Claim 16 words
A copolymer according to claim 5 in which the monomer of formula (II) is dimethylaminoethyl methacrylate.
Claim 10
Dependent Claim 16 words
A copolymer according to claim 4 in which the monomer of formula (II) is dimethylaminoethyl methacrylate.

References Cited (Backward Citations)

US3455889A Cited
US3474079A Cited
GB1190106A Cited
US3910862A Cited
US3838104A Cited
US4127711A Cited
US4147851A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1985-12-27 1986-06-28 1986-12-28 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1989-12-27 1990-06-28 1990-12-28 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1993-12-27 1994-06-28 1994-12-28 $7700.00 Window Closed / Lapsed

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