Fluorosurfactants

A compound of formula IIIa, IIIb or IIIc

• F5S—(CH2)n—X IIIa
• F5S—CH2—CH(Hal)-(CH2)(n−1)—X IIIb
• F5S—CH═CH—(CH2)(n−1)—X IIIc
• in which
• n is an integer from the range 1 to 30;
• (Hal) is F, Cl, Br or I;
• and
• X is
• (a) an anionic polar group selected from —COOM, —SO3M, —OSO3M, —PO3M2, —OPO3M2, —(OCH2CH2)m—O—(CH2)o—COOM, —(OCH2CH2)m—O—(CH2)o—SO3M, —(OCH2CH2)m—O—(CH2)oOSO3M, —(OCH2CH2)m—O—(CH2)o—PO3M2, and —(OCH2CH2)m—O—(CH2)o—OPO3M2, in which
• M is H, an alkali metal ion, or NH4+,
• m is an integer from the range 1 to 1000, and
• o is an integer selected from 1, 2, 3 or 4;
• (b) a cationic polar group selected from —NR1R2R3+Z−, —PR1R2R3+Z−,
• in which
• R is H or C1-4-alkyl in any desired position,
• Z− is Cl−, Br−, I−, CH3SO3−, CF3SO3−, CH3PhSO3−, PhSO3−,
• R1, R2 and R3 are each, independently of one another, H, C1-30-alkyl, Ar, or —CH2Ar, and
• Ar is an unsubstituted or mono- or polysubstituted aromatic ring or fused ring system having 6 to 18 C atoms, in which, in addition, one or two CH groups are each optionally replaced by N;
• (c) a polymerizable group selected from —(OCH2CH2)mOCOCR═CH2, —(OCH2CH2)m—OCR═CH2,
• in which m is an integer from the range 0 to 1000, and
• R and R1 are each H or C1-4—;
• or
• (d) an amphoteric group selected from acetyldiamines, the N-alkylamino acids, betaines, amine oxides, and corresponding derivatives thereof;
• or a corresponding salt of a compound of formula IIIa, IIIb or IIIc,
• with the proviso that when said compound if of formula IIIa or IIIc and X is an anionic polar group of (a), then n is 4-28.

A compound of formula IIIa, IIIb or IIIc

• F5S—(CH2)n—X IIIa
• F5S—CH2—CH(Hal)-(CH2)(n−1)—X IIIb
• F5S—CH═CH—(CH2)(n−1)—X IIIc
• in which
• (Hal) is F, Cl, Br or I;
• and
• X is a nonionic polar group selected from —Cl, —O-(glycoside)o, —(OCH2CH2)m—OCH2—CHOH—CH2—OH, —(OCH2CH2)m—OCH2Ar(—NCO)p, —(OCH2CH2)m—OAr(—NCO)p, —SiR1R2Z, —SiR1Z2, —SiZ3, —COZ, —(OCH2CH2)m—SO2CH═CH2, —SO2Z, and
• m is an integer from the range 0 to 1000,
• n is an integer from the range 8 to 24,
• o is an integer from the range 1 to 10,
• p is 1 or 2,
• R1 and R2 are each, independently of one another, C1-30-alkyl, Ar, or —CH2Ar,
• Ar is an unsubstituted or mono- or polysubstituted aromatic ring or fused ring system having 6 to 18 C atoms, in which, in addition, one or two CH groups are each optionally replaced by N,
• glycoside is an etherified carbohydrate,
• all Z are each, independently of one another, —H, —Cl, —F, —NR1R2, —OR1, or —N-imidazolyl, and
• Y is Cl or F.

A compound of formula IIa, IIb or IIc

• CF3O—(CH2)n—X IIa
• CF3O—CH2—CH(Hal)-(CH2)(n−1)—X IIb
• CF3O—CH═CH—(CH2)(n−1)—X IIc
• in which
• n is an integer from the range 1 to 30,
• (Hal) is F, Cl, Br or I,
• X is (a) —COOM, —SO3M, —OSO3M, —PO3M2, —OPO3M2, —(OCH2CH2)m—O—(CH2)o—COOM, —(OCH2CH2)m—O—(CH2)o—SO3M, —(OCH2CH2)m—O—(CH2)o—OSO3M, —(OCH2CH2)m—O—(CH2)o—PO3M2, or —(OCH2CH2)m—O—(CH2)o—OPO3M2,
• M is H, an alkali metal ion, or NH4+,
• m is an integer from the range 1 to 1000, and
• o is an integer selected from 1, 2, 3 or 4,
• wherein X is not —COOH;
• (b) —NR1R2R3+Z−, —PR1R2R3+Z−,
• R is H or C1-4-alkyl in any desired position,
• Z− is Cl−, Br−, I−, CH3SO3−, CF3SO3−, CH3PhSO3−, or PhSO3−,
• R1, R2 and R3 are each, independently of one another, H, C1-30-alkyl, Ar, or —CH2Ar, and
• Ar is an unsubstituted or mono- or polysubstituted aromatic ring or fused ring system having 6 to 18 C atoms, in which, in addition, one or two CH groups are each optionally replaced by N;
• (c) —Cl, —Br, —I, —(OCH2CH2)m—OH, —O-(glycoside)o, —(OCH2CH2)m—OCH2—CHOH—CH2—OH, —(OCH2CH2)m—OCH2Ar(—NCO)p, —(OCH2CH2)m—OAr(—NCO)p, —SiR1R2Z, —SiR1Z2, —SiZ3, —COZ, —(OCH2CH2)m—SO2CH═CH2, —SO2Z, or
• m is an integer from the range 0 to 1000,
• o is an integer from the range 1 to 10,
• p is 1 or 2,
• R1 and R2 are each, independently of one another, C1-30-alkyl, Ar, or —CH2Ar,
• Ar is an unsubstituted or mono- or polysubstituted aromatic ring or fused ring system having 6 to 18 C atoms, in which, in addition, one or two CH groups are each optionally replaced by N,
• glycoside is an etherified carbohydrate,
• all Z are each, independently of one another, —H, —Cl, —F, —NR1R2, —OR1, or —N-imidazolyl, and
• Y is Cl or F;
• or
• (d) —(OCH2CH2)mOCOCR═CH2, —(OCH2CH2)m—OCR═CH2,
• m is an integer from the range 0 to 1000, and
• R and R1 are each H or C1-4-alkyl;
• or a corresponding salt of a compound of the formula IIa, IIb or IIc.

A compound of formula IIb or IIc

• CF3O—CH2—CH(Hal)-(CH2)(n−1)—X IIb
• CF3O—CH═CH—(CH2)(n−1)—X IIc
• in which
• n is an integer from the range 1 to 30,
• X is a cationic, nonionic, amphoteric or anionic polar group or a polymerizable group, and
• (Hal) is F, Cl, Br or I,
• or a corresponding salt of a compound of the formula IIb or IIc.