Perfluoroalkyl-containing complexes with sugar radicals, process for their production and their use

Perfluoroalkyl-containing metal complexes with sugar radicals of formula I

• in which
• R is a monosaccharide or oligosaccharide radical that is bonded via the 1-OH position or 1-SH position,
• Rf is a perfluorinated, straight-chain or branched carbon chain with the formula —CnF2nE, in which E is a terminal fluorine, chlorine, bromine, iodine or hydrogen atom, and n is a number from 4-30,
• K is a metal complex of formula II
• in which
• R1 is a hydrogen atom or a metal ion equivalent of atomic numbers 21-29, 31-33, 37-39, 42-44, 49 or 57-83, provided that at least two R1 are metal ion equivalents,
• R2 and R3, independently of one another, are hydrogen, C1-C7 alkyl, benzyl, phenyl, —CH2OH or —CH2OCH3, and
• U is —C6H4—O—CH2-ω-, —(CH2)1-5-ω, a phenylene group, —CH2—NHCO—CH2—CH(CH2COOH)—C6H4-ω-, —C6H4—(OCH2CH2)0-1—N(CH2COOH)—CH2-ω or a C1-C12 alkylene group or a C7-C12-C6H4—O group that is optionally interrupted by one or more oxygen atoms, 1 to 3 —NHCO groups or 1- to 3 —CONH groups and/or is substituted with 1 to 3 —(CH2)0-5COOH groups, whereby ω stands for the binding site to —CO—,
• or of formula III
• in which R1 has the above-mentioned meaning, R4 is hydrogen or a metal ion equivalent that is mentioned under R1, and U1 is —C6H4—O—CH2-ω-, whereby ω means the binding site to —CO—
• or of formula IV
• in which R1 and R2 have the above-mentioned meaning
• or of formula V A or V B
• in which R1 has the above-mentioned meaning,
• or of formula VI
• in which R1 has the above-mentioned meaning,
• or of formula VII
• in which R1 has the above-mentioned meaning, and
• U1 is —C6H4—O—CH2-ω-, whereby ω means the binding site to —CO—,
• or of formula VIII
• in which R1 the above-mentioned meaning,
• and in radical K, optionally present free acid groups optionally can be present as salts of organic and/or inorganic bases or amino acids or amino acid amides,
• G for the case that K means metal complexes II to VII, is a radical that is functionalized in at least three places and that is selected from radicals a) to j) below
• and
• G for the case that K means metal complex VIII, is a radical that is functionalized in at least three places and that is selected from k) or l),
• whereby α is the binding site of G to complex K, β is the binding site of G to radical Y and γ is the binding site of G to radical Z,
• Y is —CH2, δ-(CH2)nCO-β (whereby n=1-5), δ-CH2—CHOH—CO-β or δ-CH(CHOH—CH2OH)—CHOH—CHOH—CO-β, whereby δ is the binding site to sugar radical R and β is the binding site to radical G,
• Z stands for γ-COCH2—N(C2H5)—SO2-ξ,
• γ-COCH2—O—(CH2)2—SO2-ξ,
• or
• γ-NHCH2CH2—O—CH2CH2-ξ,
• whereby γ is the binding site of Z to radical G, and ξ is the binding site of Z to perfluorinated radical Rf,
• and
• 1 and m, independently of one another, are the whole numbers 1 or 2,
• and
• p is a whole number 1 to 4.