Poly-perfluoroalkyl-substituted alcohols and acids, and derivatives thereof
AssigneeCiba-Geigy Corporation
InventorsMarlon Haniff, Robert Falk, Ted Deisenroth, Karl F. Mueller
Life of this patent
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Abstract
Di-, tri- and poly-perfluoroalkyl-substituted alcohols and acids and derivatives thereof are described which are prepared from perfluoroalkyl iodides and di-, tri- or polyallyl alcohols or acids. These compounds contain two or more perfluoroalkyl-iodoalkyl or perfluoroalkyl-alkenyl groups and one or two alcohol or acid groups or derivatized alcohol or acid functions. They can be reacted with isocyanates, epoxy compounds, anhydrides, acids or acid derivatives to prepare a great variety of oil- and water-repellent compositions which are useful for oil- and water-repellent treatment of textiles, glass, paper, leather and other substrates.
Claims18
An oligo-perfluoroalkyl alcohol or acid of the formula I or II
- (Q.sub.F --CH.sub.2 O).sub.b --Y--(X).sub.a (I)
- or
- Z.sub.e (--L--(U--OH).sub.d).sub.c (II)
- wherein
- Q.sub.F is Q.sub.F1 or Q.sub.F2, in which Q.sub.F1 is R.sub.F CH.sub.2 CHI-- and Q.sub.F2 is R.sub.F CH.dbd.CH--, and
- R.sub.F is a monovalent, perfluorinated, alkyl or alkenyl, straight, branched or cyclic organic radical having three to twenty fully fluorinated carbon atoms, which radical can be interrupted by divalent oxygen or sulfur atoms, with each R.sub.F radical being identical or different from the other R.sub.F radicals,
- Y is a trivalent or tetravalent organic linking group with from 1 to 20 carbon atoms, which can be interrupted by one or more polyvalent groups or hetero atoms selected from --O--, --S--, --N<,--NR.sub.1 --,--CO--,--CONR.sub.1 --, --NHCOO--,--CON<, --CO.sub.2 --, --O.sub.2 C--, --O.sub.2 CO-- and --SO.sub.2 --, in which
- R.sub.1 is hydrogen, C.sub.1 -C.sub.20 alkyl, di-C.sub.1 -C.sub.2 alkylamino-C.sub.2 -C.sub.6 alkylene, hydroxy-C.sub.1 -C.sub.5 alkylene, or C.sub.1 -C.sub.5 alkyl or hydroxy-C.sub.1 -C.sub.5 alkylene, which is substituted by pyridyl, piperidyl or cyclohexyl.
- X is OH, O--CH.sub.2 --COOH or COOH,
- a is 1 or 2,
- b is 2 or 3,
- L is O, S or NR', in which
- R' is C.sub.1 -C.sub.20 hydrocarbyl, hydroxy-C.sub.2 -C.sub.5 alkylene, carboxymethylene or U--OH, ##STR9## Z is H or a mono-, di-, tri- or tetravalent organic group of 1-40 carbon atoms which can be interrupted by one or more polyvalent groups or hetero atoms selected from --O--, --S--, --N<, --NR.sub.1 --, --CO--, --CONR.sub.1 --, --NHCOO--, --CON<, --CO.sub.2 --, --O.sub.2 C--, --O.sub.2 CO-- and --SO.sub.2 --, and can also be substituted by hydroxyl, carboxyl, carboxyalkyl or sulfonate when L is S or NR', r and q are each, independently, 0 to 10,
- c is 1 to 4,
- d is 1 to 3, with the proviso that when c and d are both 1, Z is monovalent and r is >0, and
- e is 0 or 1, with the proviso that when e is 0, d is 2 and L is S or NR'.
An acid of the formula ##STR11## where Q.sub.F is Q.sub.F1 or Q.sub.F2, in which Q.sub.F1 is R.sub.F CH.sub.2 CHI-- and Q.sub.F2 is R.sub.F CH.dbd.CH--, and R.sub.F is a monovalent, perfluorinated, alkyl or alkenyl, straight, branched or cyclic organic radical having three to twenty fully fluorinated carbon atoms, which radical can be interrupted by divalent oxygen or sulfur atoms, with each R.sub.F radical being identical or different from the other R.sub.F radicals.
Dependencies are inferred from the claim text.