DE102011114650A1 - New pentafluorosulfoxy derivative useful e.g. as a surfactant, a water repellent, an oil repellent, preferably in the surface modification of textiles, paper, glass, porous building materials or adsorbents, and as an antistatic agent - Google Patents

Abstract

Pentafluorosulfoxy derivative (I), is new. Pentafluorosulfoxy derivative of formula (Z-(Ar1) n1-(O) n2-(CH 2) n3-OSF 5) (I), is new. Z : anionic substituents, preferably -COO ->M +>, -SO 3->M +>, -OSO 3->M +>, -PO 32->M +>, -OPO 32->M 2+>, -NHSO 3-M +>, -(OCH 2CH 2) qO ->M +>, -(OCH 2CH 2) qO ->M +>, -(OCH 2CH 2) q2O(CCH 2) rCOO-M +>, -(OCH 2) rCOO-M +>, -(OCH 2CH 2) 5O(CH 2) tSO 3-M +>, -(OCH 2CH 2) uO(CH 2) uOSO 3-M +>, -(OCH 2CH 2) wOCH 2) xPO 32->M 2+>-(OCH 2CH 2) yO(CH 2) 3OPO 32>-M 2+>, cationic substituents, preferably -N(R1)(R2)(R3) +>X ->, -P(R4)(R5)(R6) +>X ->, pyridinium derivative of formula (II), isoquinolinium derivative of formula (III) or (IV), neutral substituent, preferably alkyl, -OH, -O(O)C-alkyl, -(OCH 2CH 2) bOH, -O-(glycoside) c(glucoside, diglucoside, triglucoside), -OCH 2CHOHCH 2OH or -(OCH 2CH 2) dOCH 2CHOHCH 2OH, reactive substituents, preferably -(OCH 2CH 2) g(OCH 2-phenyl) hNCO, -SiR7R8W1, -SiR9W1 2, -SiW1 3, COW1, -(OCH 2CH 2) iSO 2CH=CH2, triazine derivative of formula (V), polymerizable substituents, preferably -(OCH 2CH 2) kOCOCR=CH 2, -(OCH 2CH 2) k2OCH=CH 2, epoxide derivative of formula (VI) or oxetane derivative of formula (VII); M : H +>, metal cation, preferably alkali metal cation or alkaline earth metal cation , preferably Li +>, Na +>, K +>, NH 4+>, Ca 2+>or Zn 2+>; q, q2, s, u, w, y, b, c : 1-1000; r, t, v, x, a : 1-3; R10 : H or -CH 3; X ->Cl ->, Br ->, I ->, CH 3SO 3->, methylphenyl-SO 3->or phenyl-SO 3->; R1-R6 : H, alkyl, aryl or benzyl; b, d : 1-1000; c, e, f : 1-10; R7, R8, R9 : alkyl, aryl or benzyl, preferably CH 3; W1 : H, Cl, F, NR12 2, OR12 or N-imidazoyl; R11 : Cl or F; either R12 : optionally substituted alkyl; or R12 : N+R12 2= heterocyclic group; g, i, j : 0-1000; R : H or CH 3; h : 0 or 1; k, k2, l, k3 : 0-1000; Ar1 : aromatic monocyclic or bicyclic carbon ring of 5-18 carbon; n1, n2 : 0 (preferred) or 1; and n3 : 0-1000, preferably 2-6. Independent claims are also included for: (1) the preparation of (I); (2) an agent comprising (I); and (3) an intermediate compound of formula (V1-(Ar1) n1-(O) n2-(CH 2) n3-OSF 5). V1 : H 2C=CH-, alkyl-HC=CH-, Cl, Br, I, OH, -OCH 2-phenyl, -BR13 2, -SiR13 3or -O3SR13; and R13 : alkyl, aryl, F, CF 3or phenyl-CH 3. [Image] [Image] [Image].

Description

Technical area

The present invention relates to novel compounds with OSF _{5 end} groups, their use as surface-active substances and preparation processes for these compounds.

Background of the invention

Fluorosurfactants have an outstanding ability to reduce the surface tension, for example, in the hydrophobization of surfaces z. B. of textiles, paper, glass, building materials or adsorbents is used. In addition, it is possible to use them as an interface or emulsifier or viscosity reducer in paints, varnishes or adhesives.

In general, fluorosurfactants contain perfluoroalkyl substituents which are degraded in the environment by biological and / or other oxidation processes to perfluoroalkylcarboxylic acids (PFCA's) and -sulfonic acids (PFAS's). In recent years, the accumulation of perfluoroalkylcarboxylic acids (PFCA's) and perfluoroalkylsulfonic acids (PFAS's) in nature have been a concern. PFCA's and PFAS's are highly persistent compounds whose long-chain variants (with perfluoroalkyl chains of 8 or more carbon atoms) have bioaccumulative potential. They are partly suspected of causing health damage ( GL Kennedy, Jr., JL Butenhoff, GW Olsen, JC O'Connor, AM Seacat, RG Biegel, SR Murphy, DG Farrar, Critical Review in Toxicology, 2004, 34, 351-384 ).

Sulfosuccinates and / or sulfotricarballylates with different fluorinated side chains are known in US 4,968,599 and US 4,988,610 such as US 6,890,608 described and in AR Pitt et al., Colloids and Surfaces A: Physicochemical and Engineering Aspects, 1996, 114, 321-335 ; AR Pitt, Progr. Colloid Polym. Sci, 1997, 103, 307-317 and Z.-T. Liu et al., Ind. Eng. Chem. Res. 2007, 46, 22-28 ,

The company Omnova markets polymers whose side chains have terminal CF ₃ or C ₂ F ₅ groups. In the international patent application WO 03/010128 are described perfluoroalkyl-substituted amines, acids, amino acids and thioethers having a C3-20 perfluoroalkyl group.

Out JP-A-2001/133984 are surface active compounds with perfluoroalkoxy chains known, which are suitable for use in antireflection coatings. Out JP-A-09/111286 the use of perfluoropolyether surfactants in emulsions is known.

In the older German patent application DE 102005000858 Compounds which carry at least one terminal pentafluorosulfuranyl group or at least one terminal pentafluorosulfoxy group and have a polar end group, are surface-active and are suitable as surfactants.

The sulfonic acid HO ₃ S-Ph-OSF ₅ and the carboxylic acid HOOC-Ph-OSF ₅ are known from the literature ( JR Case, R. Price, NH Ray, HL Roberts, J. Wright, J. Chem. Soc. 1962, 2107-2110 ; JR Case, HL Roberts, UK 928412, 1963 ).

Furthermore, there is a need for alternative surface-active substances, preferably with a, the conventional fluorosurfactants, comparable property profile, as well as a large chemical versatility, which preferably do not degrade during long-chain persistent fluorocarboxylic or fluorosulfonic in oxidative or reductive degradation or are preferably effective in lower dosage as conventional fluorosurfactants.

There have now been found new compounds which are suitable as surface-active substances and preferably one or more of the above-mentioned. Do not have disadvantages.

By including a reference in this application is not stated that the reference is a relevant prior art for this application.

Summary of the invention

The object of the present invention is the provision of new fluorosurfactants.

• (i) anionische Substituenten: -COO^–M⁺, -SO₃ ^–M⁺, -OSO₃ ^–M⁺, -PO₃ ^2–M⁺ ₂, -OPO₃ ^2–M⁺ ₂, -NHSO₃ ^–M⁺, -(OCH₂CH₂)_qO^–M⁺, -(OCH₂CH₂)_qqO(CH₂)_rCOO^–M⁺ -(OCH₂CH₂)_sO(CH₂)_tSO₃ ^–M⁺, -(OCH₂CH₂)_uO(CH₂)_vOSO₃ ^–M⁺, -(OCH₂CH₂)_wO(CH₂)_xPO₃ ^2–M⁺ ₂ or -(OCH₂CH₂)_yO(CH₂)_aOPO₃ ^2–M⁺ ₂, wobei: M⁺ unabhängig voneinander H⁺, ein Metallkation, bevorzugt ein Alkalimetallkation oder Erdalkalimetallkation, besonders bevorzugt Li⁺, Na⁺, K⁺, NH₄ ⁺, Ca²⁺ oder Zn²⁺ bedeutet, q, qq, s, u, w, y unabhängig voneinander 1–1000 bedeuten, r, t, v, x, a unabhängig voneinander 1, 2 oder 3 bedeuten,
• (ii) kationische Substituenten: -N(R¹R²R³)⁺X^–, -P(R⁴R⁵R⁶)⁺X^–,
  
  wobei: R_a unabhängig voneinander H oder -CH₃ bedeutet, X^– unabhängig voneinander Cl^–, Br^–, I^–, CH₃SO₃ ^–, CF₃SO₃, methylphenyl- SO₃ ^– or phenyl-SO₃ ^– bedeutet, R¹, R², R³, R⁴, R⁴, R⁶ unabhängig voneinander H, alkyl, aryl oder benzyl bedeuten,
• (iii) neutrale Substituenten: alkyl, -OH, -O(O)C-alkyl, -(OCH₂CH₂)_bOH, -O-(glycosid)_c (z. B. glucosid, diglucosid, triglucosid etc.), -OCH₂CHOHCH₂OH oder -(OCH₂CH₂)_dOCH₂CHOHCH₂OH, wobei: b, d unabhängig voneinander 1–1000 bedeuten, c, e, f unabhängig voneinander 1–10 bedeuten,
• (iv) reaktive Substituenten: -(OCH₂CH₂)_g(OCH₂-phenyl)_hNCO, -SiR⁷R⁸W, -SiR⁹W₂, -SiW₃, COW, -(OCH₂CH₂)_iSO₂CH=CH₂ or
  
  wobei: R⁷, R⁸, R⁹ unabhängig voneinander alkyl, aryl oder benzyl, bevorzugt CH₃ bedeuten, W unabhängig voneinander H, Cl, F, NR^d ₂, OR^d oder N-imidazolyl bedeutet, R_b unabhängig voneinander Cl oder F bedeuten, R^d unabhängig voneinander optional substituiertes alkyl bedeutet, wobei im Fall von NR^d ₂ beide Reste R^d zusammen mit dem Stickstoffatom, an dem sie befestigt sind, auch heterocyclyl bilden können, g, i, j unabhängig voneinander 0–1000 bedeuten, h 0 oder 1 bedeutet,
• (v) polymerisierbare Substituenten: -(OCH₂CH₂)_kOCOCR=CH₂, -(OCH₂CH₂)_kkOCH=CH₂,
  
  wobei: R unabhängig voneinander H oder CH₃ bedeutet, k, kk, I, II unabhängig voneinander 0–1000 bedeuten, Ar einen aromatischen mono- oder bicyclischen Kohlenstoffring mit 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 oder 18 C-Atomen bedeutet, n1, n2 unabhängig voneinander 0 oder 1, bevorzugt 0 bedeuten, n3 0–1000, bevorzugt 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 oder 10, besonders bevorzugt 2, 3, 4, 5 oder 6 bedeutet.

The object of the present invention was surprisingly achieved in one aspect by providing compounds of the formula (I) Z- (Ar) _n1 - (O) _n2 - (CH _{2) n3} -OSF ₅ (I) in which:
Z is selected from the group consisting of:

• (i) anionic substituents: -COO ^- M ^+, -SO ₃ ^- M ^+, -OSO ₃ ^- M ^+, -PO ₃ ^2- M ⁺ _2, -OPO ₃ ^2- M ⁺ _2, -NHSO ₃ ^- M ⁺ , - (OCH ₂ CH ₂ ) _q O ^- M ⁺ , - (OCH ₂ CH ₂ ) _qq O (CH ₂ ) _r COO ^- M ⁺ - (OCH ₂ CH ₂ ) _s O (CH ₂ ) _t SO ₃ ^- M ⁺ , - (OCH ₂ CH ₂ ) _u O (CH ₂ ) _v OSO ₃ ^- M ⁺ , - (OCH ₂ CH ₂ ) _w O (CH ₂ ) _x PO ₃ ^2- M ⁺ ₂ or - (OCH ₂ CH ₂ ) _y O (CH ₂ ) _a OPO ₃ ^2- M ⁺ ₂ , wherein: M ⁺ independently H ⁺ , a metal cation, preferably an alkali metal cation or alkaline earth metal cation, more preferably Li ⁺ , Na ⁺ , K ⁺ , NH ₄ ⁺ , Ca ²⁺ or Zn ²⁺ , q, qq, s, u, w, y independently of one another denote 1-1000, r, t, v, x, a independently of one another denote 1, 2 or 3,
• (ii) cationic substituents: -N (R ¹ R ² R ³ ) ⁺ X ^- , -P (R ⁴ R ⁵ R ⁶ ) ⁺ X ^- ,
  
  where: R _a independently of one another is H or -CH ₃ , X ^- independently of one another is Cl ^- , Br ^- , I ^- , CH ₃ SO ₃ ^- , CF ₃ SO ₃ , methylphenyl-SO ₃ ^- or phenyl-SO ₃ ^- , R ¹ , R ² , R ³ , R ⁴ , R ⁴ , R ⁶ independently of one another are H, alkyl, aryl or benzyl,
• (iii) neutral substituents: alkyl, -OH, -O (O) C-alkyl, - (OCH ₂ CH ₂ ) _b OH, -O- (glycoside) _c (eg glucoside, diglucoside, triglucoside etc.) , -OCH ₂ CHOHCH ₂ OH or - (OCH ₂ CH ₂ ) _d OCH ₂ CHOHCH ₂ OH, wherein: b, d independently of one another are 1-1000, c, e, f independently of one another denote 1-10,
• (iv) reactive substituents: - (OCH ₂ CH ₂ ) _g (OCH ₂ -phenyl) _h NCO, -SiR ⁷ R ⁸ W, -SiR ⁹ W ₂ , -SiW ₃ , COW, - (OCH ₂ CH ₂ ) _i SO ₂ CH = CH ₂ or
  
  wherein: R ⁷ , R ⁸ , R ^{9 are} independently alkyl, aryl or benzyl, preferably CH ₃ , W is independently H, Cl, F, NR ^d ₂ , OR ^d or N-imidazolyl, R _b independently of one another Cl or F, R ^d independently of one another are optionally substituted alkyl, where in the case of NR ^d ₂ both radicals R ^d together with the nitrogen atom to which they are attached can also form heterocyclyl, g, i, j independently of one another denote 0-1000 , h is 0 or 1,
• (v) polymerizable substituents: - (OCH ₂ CH ₂ ) _k OCOCR = CH ₂ , - (OCH ₂ CH ₂ ) _kk OCH = CH ₂ ,
  
  wherein: R is independently H or CH ₃ , k, kk, I, II are independently 0-1000, Ar is an aromatic mono- or bicyclic carbon ring of 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms, n1, n2 are independently 0 or 1, preferably 0, n3 0-1000, preferably 0, 1, 2, 3, 4, 5, 6, 7 , 8, 9 or 10, more preferably 2, 3, 4, 5 or 6.

The term "glycoside" means etherified carbohydrate, preferably a mono-, di-, tri- or oligoglucoside.

In a preferred embodiment, compounds of formula (I) are provided wherein n1 and n2 are 0.

worin bevorzugt a1 1–20, W OR^d und R^d alkyl bedeuten, bedeutet.In a preferred embodiment compounds of formula (I) are as defined above and above preferred embodiments provided, wherein Z is a substituent selected from the group consisting of alkyl, -SO ₃ ^- M ^+, -O (CH ₂ CH ₂ O) _a1 H , -OH, -SiW ₃ , -O (O) C-alkyl,

in which preferably a1 is 1-20, W is OR ^d and R ^{d is} alkyl.

In a preferred embodiment there are provided compounds of the formula (1) as defined above and the above preferred embodiments wherein Ar represents phenyl or naphthyl.

worin bevorzugt a1 1–20, W OR^d und R^d alkyl bedeuten, bedeutet, und Ar phenyl oder naphthyl bedeutet.In a preferred embodiment compounds of formula (I) are as defined above and above preferred embodiments provided, wherein Z is a substituent selected from the group consisting of alkyl, -SO ₃ ^- M ^+, -O (CH ₂ CH ₂ O) _a1 H _' -OH, -SiW ₃ , -O (O) C-alkyl,

wherein preferably a1 is 1-20, W is OR ^d and R ^{d is} alkyl, and Ar is phenyl or naphthyl.

Also included within the invention are compounds which can be derived from the formula (I) by the formal insertion of an aromatic substructure, e.g. B .:

(EtO)₃Si(CH₂)OSF₅, F₅SO-(CH₂)₄-COOH; F₅SO-(CH₂)₄-SO₃H; F₅SO-(CH₂)₄-O-SO₃H F₅SO-(CH₂)₅-COOH; F₅SO-(CH₂)₅-SO₃H; F₅SO-(CH₂)₅-O-SO₃H F₅SO-(CH₂)₆-COOH; F₅SO-(CH₂)₆-SO₃H; F₅SO-(CH₂)₆-O-SO₃H F₅SO-(CH₂)₇-COOH; F₅SO-(CH₂)₇-SO₃H; F₅SO-(CH₂)₇-O-SO₃H F₅SO-(CH₂)₈-COOH; F₅SO-(CH₂)₈-SO₃H; F₅SO-(OH₂)₈-O-SO₃H F₅SO-(CH₂)₉-COOH; F₅SO-(CH₂)₉-SO₃H; F₅SO-(CH₂)₉-O-SO₃H F₅SO-(CH₂)₁₀-COOH; F₅SO-(CH₂)₁₀-SO₃H; F₅SO-(CH₂)₁₀-O-SO₃H F₅SO-(CH₂)₁₁-COOH; F₅SO-(CH₂)₁₁-SO₃H; F₅SO-(CH₂)₁₁-O-SO₃H F₅SO-(CH₂)₁₂-COOH; F₅SO-(CH₂)₁₂-SO₃H; F₅SO-(CH₂)₁₂-O-SO₃H F₅SO-(CH₂)₁₃-COOH; F₅SO-(CH₂)₁₃-SO₃H; F₅SO-(CH₂)₁₃-O-SO₃H F₅SO-(CH₂)₁₄-COOH; F₅SO-(CH₂)₁₄-SO₃H; F₅SO-(CH₂)₁₄-O-SO₃H F₅SO-(CH₂)₁₅-COOH; F₅SO-(CH₂)₁₅-SO₃H; F₅SO-(CH₂)₁₅-O-SO₃H F₅SO-(CH₂)₁₆-COOH; F₅SO-(CH₂)₁₆-SO₃H; F₅SO-(CH₂)₁₆-O-SO₃H F₅SO-(CH₂)₁₇-COOH; F₅SO-(CH₂)₁₇-SO₃H; F₅SO-(CH₂)₁₇-O-SO₃H F₅SO-(CH₂)₁₈-COOH; F₅SO-(CH₂)₁₈-SO₃H; F₅SO-(CH₂)₁₈-O-SO₃H F₅SO-(CH₂)₁₉-COOH; F₅SO-(CH₂)₁₉-SO₃H; F₅SO-(CH₂)₁₉-O-SO₃H F₅SO-(CH₂)₂₀-COOH; F₅SO-(CH₂)₂₀-SO₃H; F₅SO-(CH₂)₂₀-O-SO₃H F₅SO-(CH₂)₂₁-COOH; F₅SO-(CH₂)₂₁-SO₃H; F₅SO-(CH₂)₂₁-O-SO₃H F₅SO-(CH₂)₂₂-COOH; F₅(SO-(CH₂)₂₂-SO₃H; F₅SO-(CH₂)₂₂-O-SO₃H F₅SO-(CH₂)₂₃-COOH; F₅SO-(CH₂)₂₃-SO₃H; F₅SO-(CH₂)₂₃-O-SO₃H F₅SO-(CH₂)₂₄-COOH; F₅SO-(CH₂)₂₄-SO₃H; F₅SO-(CH₂)₂₄-O-SO₃H F₅SO-(CH₂)₄-COONa; F₅SO-(CH₂)₄-SO₃Na; F₅SO-(CH₂)₄-O-SO₃Na F₅SO-(CH₂)₅-COONa; F₅SO-(CH₂)₅-SO₃Na; F₅SO-(OH₂)₅-O-SO₃Na F₅SO-(CH₂)₆-COONa; F₅SO-(CH₂)₆-SO₃Na; F₅SO-(CH₂)₆-O-SO₃Na F₅SO-(CH₂)₇-COONa; F₅SO-(CH₂)₇-SO₃Na; F₅SO-(CH₂)₇-O-SO₃Na F₅SO-(CH₂)₈-COONa; F₅SO-(CH₂)₈-SO₃Na; F₅SO-(CH₂)₈-O-SO₃Na F₅SO-(CH₂)₉-COONa; F₅SO-(CH₂)₉-SO₃Na; F₅SO-(CH₂)₉-O-SO₃Na F₅SO-(CH₂)₁₀-COONa; F₅SO-(CH₂)₁₀-SO₃Na; F₅SO-(CH₂)₁₀-O-SO₃Na F₅SO-(CH₂)₁₁-COONa; F₅SO-(CH₂)₁₁-SO₃Na; F₅SO-(CH₂)₁₁-O-SO₃Na F₅SO-(CH₂)₁₂-COONa; F₅SO-(CH₂)₁₂-SO₃Na; F₅SO-(CH₂)₁₂-O-SO₃Na F₅SO-(CH₂)₁₃-COONa; F₅SO-(CH₂)₁₃-SO₃Na; F₅SO-(CH₂)₁₃-O-SO₃Na F₅SO-(CH₂)₁₄-COONa; F₅SO-(CH₂)₁₄-SO₃Na; F₅SO-(CH₂)₁₄-O-SO₃Na F₅SO-(CH₂)₁₅-COONa; F₅SO-(CH₂)₁₅-SO₃Na; F₅SO-(CH₂)₁₅-O-SO₃Na F₅SO-(CH₂)₁₆-COONa; F₅SO-(CH₂)₁₆-SO₃Na; F₅SO-(CH₂)₁₆-O-SO₃Na F₅SO-(CH₂)₁₇-COONa; F₅SO-(CH₂)₁₇-SO₃Na; F₅SO-(CH₂)₁₇-O-SO₃Na F₅SO-(CH₂)₁₈-COONa; F₅SO-(CH₂)₁₈-SO₃Na; F₅SO-(CH₂)₁₈-O-SO₃Na F₅SO-(CH₂)₁₉-COONa; F₅SO-(CH₂)₁₉-SO₃Na; F₅SO-(CH₂)₁₉-O-SO₃Na F₅SO-(CH₂)₂₀-COONa; F₅SO-(CH₂)₂₀-SO₃Na; F₅SO-(CH₂)₂₀-O-SO₃Na F₅SO-(CH₂)₂₁-COONa; F₅SO-(CH₂)₂₁-SO₃Na; F₅SO-(CH₂)₂₁-O-SO₃Na F₅SO-(CH₂)₂₂-COONa; F₅SO-(CH₂)₂₂-SO₃Na; F₅SO-(CH₂)₂₂-O-SO₃Na F₅SO-(CH₂)₂₃-COONa; F₅SO-(CH₂)₂₃-SO₃Na; F₅SO-(CH₂)₂₃-O-SO₃Na F₅SO-(CH₂)₂₄-COONa; F₅SO-(CH₂)₂₄-SO₃Na; F₅SO-(CH₂)₂₄-O-SO₃Na F₅SO-(Phenyl)-COOH; F₅SO-(Phenyl)-SO₃H; F₅SO-(Phenyl)-O-SO₃H F₅SO-CH₂-(Phenyl)-COOH; F₅SO-CH₂-(Phenyl)-SO₃H; F₅SO-CH₂-(Phenyl)-O-SO₃H F₅SO-CH₂-O-(Phenyl)-COOH; F₅SO-CH₂-O-(Phenyl)-SO₃H; F₅SO-CH₂-O-(Phenyl)-O-SO₃H F₅SO-(CH₂)₂-O-(Phenyl)-COOH; F₅SO-(CH₂)₂-O-(Phenyl)-SO₃H; F₅SO-(CH₂)₂-O-(Phenyl)-O-SO₃H F₅SO-(CH₂)₃-O-(Phenyl)-COOH; F₅SO-(CH₂)₃-O-(Phenyl)-SO₃H; F₅SO-(CH₂)₃-O-(Phenyl)-O-SO₃H F₅SO-(CH₂)₄-O-(Phenyl)-COOH; F₅SO-(CH₂)₄-O-(Phenyl)-SO₃H; F₅SO-(CH₂)₄-O-(Phenyl)-O-SO₃H F₅SO-(CH₂)₅-O-(Phenyl)-COOH; F₅SO-(CH₂)₅-O-(Phenyl)-SO₃H; F₅SO-(CH₂)₅-O-(Phenyl)-O-SO₃H F₅SO-(CH₂)₆-O-(Phenyl)-COOH; F₅SO-(CH₂)₆-O-(Phenyl)-SO₃H; F₅SO-(CH₂)₆-O-(Phenyl)-O-SO₃H F₅SO-(CH₂)₇-O-(Phenyl)-COOH; F₅SO-(CH₂)₇-O-(Phenyl)-SO₃H; F₅SO-(CH₂)₇-O-(Phenyl)-O-SO₃H F₅SO-(CH₂)₈-O-(Phenyl)-COOH; F₅SO-(CH₂)₈-O-(Phenyl)-SO₃H; F₅SO-(CH₂)₈-O-(Phenyl)-O-SO₃H F₅SO-(CH₂)₉-O-(Phenyl)-COOH; F₅SO-(CH₂)₉-O-(Phenyl)-SO₃H; F₅SO-(CH₂)₉-O-(Phenyl)-O-SO₃H F₅SO-(CH₂)₁₀-O-(Phenyl)-COOH; F₅SO-(CH₂)₁₀-O-(Phenyl)-SO₃H; F₅SO-(CH₂)₁₀-O-(Phenyl)-O-SO₃H F₅SO-(Phenyl)-COONa; F₅SO-(Phenyl)-SO₃Na; F₅SO-(Phenyl)-O-SO₃Na F₅SO-CH₂-(Phenyl)-COONa; F₅SO-CH₂-(Phenyl)-SO₃Na; F₅SO-CH₂-(Phenyl)-O-SO₃Na F₅SO-CH₂-O-(Phenyl)-COONa; F₅SO-CH₂-O-(Phenyl)-SO₃Na; F₅SO-CH₂-O-(Phenyl)-O-SO₃Na F₅SO-(CH₂)₂-O-(Phenyl)-COONa; F₅SO-(CH₂)₂-O-(Phenyl)-SO₃Na; F₅SO-(CH₂)₂-O-(Phenyl)-O-SO₃Na F₅SO-(CH₂)₃-O-(Phenyl)-COONa; F₅SO-(CH₂)₃-O-(Phenyl)-SO₃Na; F₅SO-(CH₂)₃-O-(Phenyl)-O-SO₃Na F₅SO-(CH₂)₄-O-(Phenyl)-COONa; F₅SO-(CH₂)₄-O-(Phenyl)-SO₃Na; F₅SO-(CH₂)₄-O-(Phenyl)-O-SO₃Na F₅SO-(CH₂)₅-O-(Phenyl)-COONa; F₅SO-(CH₂)₅-O-(Phenyl)-SO₃Na; F₅SO-(CH₂)₅-O-(Phenyl)-O-SO₃Na F₅SO-(CH₂)₆-O-(Phenyl)-COONa; F₅SO-(CH₂)₆-O-(Phenyl)-SO₃Na; F₅SO-(CH₂)₆-O-(Phenyl)-O-SO₃Na F₅SO-(CH₂)₇-O-(Phenyl)-COONa; F₅SO-(CH₂)₇-O-(Phenyl)-SO₃Na; F₅SO-(CH₂)₇-O-(Phenyl)-O-SO₃Na F₅SO-(CH₂)₈-O-(Phenyl)-COONa; F₅SO-(CH₂)₈-O-(Phenyl)-SO₃Na; F₅SO-(CH₂)₈-O-(Phenyl)-O-SO₃Na F₅SO-(CH₂)₉-O-(Phenyl)-COONa; F₅SO-(CH₂)₉-O-(Phenyl)-SO₃Na; F₅SO-(CH₂)₉-O-(Phenyl)-O-SO₃Na F₅SO-(CH₂)₁₀-O-(Phenyl)-COONa; F₅SO-(CH₂)₁₀-O-(Phenyl)-SO₃Na; F₅SO-(CH₂)₁₀-O-(Phenyl)-O-SO₃Na F₅SO-(CH₂)₄-OH; F₅SO-(CH₂)₄-(OCH₂CH₂)_m-OH; F₅SO-(CH₂)₄-(OCH₂CH₂)_m-SO₂-CH=CH₂ F₅SO-(CH₂)₅-OH; F₅SO-(CH₂)₅-(OCH₂CH₂)_m-OH; F₅SO-(CH₂)₅-(OCH₂CH₂)_m-SO₂-CH=CH₂ F₅SO-(CH₂)₆-ON; F₅SO-(CH₂)₆-(OCH₂CH₂)_m-OH; F₅SO-(CH₂)₆-(OCH₂CH₂)_m-SO₂-CH=CH₂ F₅SO-(CH₂)₇-OH; F₅SO-(CH₂)₇-(OCH₂CH₂)_m-OH; F₅SO-(CH₂)₇-(OCH₂CH₂)_m-SO₂-CH=CH₂ F₅SO-(CH₂)₈-OH; F₅SO-(CH₂)₈-(OCH₂CH₂)_m-OH; F₅SO-(CH₂)₈-(OCH₂CH₂)_m-SO₂-CH=CH₂ F₅SO-(CH₂)₉-OH; F₅SO-(CH₂)₉-(OCH₂CH₂)_m-OH; F₅SO-(CH₂)₉-(OCH₂CH₂)_m-SO₂-CH=CH₂ F₅SO-(CH₂)₁₀-OH; F₅SO-(CH₂)₁₀-(OCH₂CH₂)_m-OH; F₅SO-(CH₂)₁₀-(OCH₂CH₂)_m-SO₂-CH=CH₂ F₅SO-(CH₂)₁₁-OH; F₅SO-(CH₂)₁₁-(OCH₂CH₂)_m-OH; F₅SO-(CH₂)₁₁-(OCH₂CH₂)_m-SO₂-CH=CH₂ F₅SO-(CH₂)₁₂-OH; F₅SO-(CH₂)₁₂-(OCH₂CH₂)_m-OH; F₅SO-(CH₂)₁₂-(OCH₂CH₂)_m-SO₂-CH=CH₂ F₅SO-(CH₂)₁₃-OH; F₅SO-(CH₂)₁₃-(OCH₂CH₂)_m-OH; F₅SO-(CH₂)₁₃-(OCH₂CH₂)_m-SO₂-CH=CH₂ F₅SO-(CH₂)₁₄-OH; F₅SO-(CH₂)₁₄-(OCH₂CH₂)_m-OH; F₅SO-(CH₂)₁₄-(OCH₂CH₂)_m-SO₂-CH=CH₂ F₅SO-(CH₂)₁₅-OH; F₅SO-(CH₂)₁₅-(OCH₂CH₂)_m-OH; F₅SO-(CH₂)₁₅-(OCH₂CH₂)_m-SO₂-CH=CH₂ F₅SO-(CH₂)₁₆-OH; F₅SO-(CH₂)₁₆-(OCH₂CH₂)_m-OH; F₅SO-(CH₂)₁₆-(OCH₂CH₂)_m-SO₂-CH=CH₂ F₅SO-(CH₂)₁₇-OH; F₅SO-(CH₂)₁₇-(OCH₂CH₂)_m-OH; F₅SO-(CH₂)₁₇-(OCH₂CH₂)_m-SO₂-CH=CH₂ F₅SO-(CH₂)₁₈-OH; F₅SO-(CH₂)₁₈-(OCH₂CH₂)_m-OH; F₅SO-(CH₂)₁₈-(OCH₂CH₂)_m-SO₂-CH=CH₂ F₅SO-(CH₂)₁₉-OH; F₅SO-(CH₂)₁₉-(OCH₂CH₂)_m-OH; F₅SO-(CH₂)₁₉-(OCH₂CH₂)_m-SO₂-CH=CH₂ F₅SO-(CH₂)₂₀-OH; F₅SO-(CH₂)₂₀-(OCH₂CH₂)_m-OH; F₅SO-(CH₂)₂₀-(OCH₂CH₂)_m-SO₂-CH=CH₂ F₅SO-(CH₂)₂₁-OH; F₅SO-(CH₂)₂₁-(OCH₂CH₂)_m-OH; F₅SO-(CH₂)₂₁-(OCH₂CH₂)_m-SO₂-CH=CH₂ F₅SO-(CH₂)₂₂-OH; F₅SO-(CH₂)₂₂-(OCH₂CH₂)_m-OH; F₅SO-(CH₂)₂₂-(OCH₂OH₂)_m-SO₂-CH=CH₂ F₅SO-(CH₂)₂₃-OH; F₅SO-(CH₂)₂₃-(OCH₂CH₂)_m-OH; F₅SO-(CH₂)₂₃-(OCH₂CH₂)_m-SO₂-CH=CH₂ F₅SO-(CH₂)₂₄-OH; F₅SO-(CH₂)₂₄-(OCH₂CH₂)_m-OH; F₅SO-(CH₂)₂₄-(OCH₂CH₂)_m-SO₂-CH=CH₂ F₅SO-(CH₂)₄-(OCH₂CH₂)_m-OCOCH=CH₂; F₅SO-(CH₂)₄-(OCH₂CH₂)_m-OCH=CH₂; F₅SO-(CH₂)₄-(OCH₂CH₂)_m-OAr(NCO)_p F₅SO-(CH₂)₅-(OCH₂CH₂)_m-OCOCH=CH₂; F₅SO-(CH₂)₅-(OCH₂CH₂)_m-OCH=CH₂; F₅SO-(CH₂)₅-(OCH₂CH₂)_m-OAr(NCO)_p F₅SO-(CH₂)₆-(OCH₂CH₂)_m-OCOCH=CH₂; F₅SO-(CH₂)₆-(OCH₂CH₂)_m-OCH=CH₂; F₅SO-(CH₂)₆-(OCH₂CH₂)_m-OAr(NCO)_p F₅SO-(CH₂)₇-(OCH₂CH₂)_m-OCOCH=CH₂; F₅SO-(CH₂)₇-(OCH₂CH₂)_m-OCH=CH₂; F₅SO-(CH₂)₇-(OCH₂CH₂)_m-OAr(NCO)_p F₅SO-(CH₂)₈-(OCH₂CH₂)_m-OCOCH=CH₂; F₅SO-(CH₂)₈-(OCH₂CH₂)_m-OCH=CH₂; F₅SO-(CH₂)₈-(OCH₂CH₂)_m-OAr(NCO)_p F₅SO-(CH₂)₉-(OCH₂CH₂)_m-OCOCH=CH₂; F₅SO-(CH₂)₉-(OCH₂CH₂)_m-OCH=CH₂; F₅SO-(CH₂)₉-(OCH₂CH₂)_m-OAr(NCO)_p F₅SO-(CH₂)₁₀-(OCH₂CH₂)_m-OCOCH=CH₂; F₅SO-(CH₂)₁₀-(OCH₂CH₂)_mOCH=CH₂; F₅SO-(CH₂)₁₀-(OCH₂CH₂)_m-OAr(NCO)_p F₅SO-(CH₂)₁₁-(OCH₂CH₂)_m-OCOCH=CH₂; F₅SO-(CH₂)₁₁-(OCH₂CH₂)_m-OCH=CH₂; F₅SO-(CH₂)₁₁-(OCH₂CH₂)_m-OAr(NCO)_p F₅SO-(CH₂)₁₂-(OCH₂CH₂)_m-OCOCH=CH₂; F₅SO-(CH₂)₁₂-(OCH₂CH₂)_m-OCH=CH₂; F₅SO-(CH₂)₁₂-(OCH₂CH₂)_m-OAr(NCO)_p F₅SO-(CH₂)₁₃-(OCH₂CH₂)_m-OCOCH=CH₂; F₅SO-(CH₂)₁₃-(OCH₂CH₂)_m-OCH=CH₂; F₅SO-(CH₂)₁₃-(OCH₂CH₂)_m-OAr(NCO)_p F₅SO-(CH₂)₁₄-(OCH₂CH₂)_m-OCOCH=CH₂; F₅SO-(CH₂)₁₄-(OCH₂CH₂)_m-OCH=CH₂; F₅SO-(CH₂)₁₄-(OCH₂CH₂)_m-OAr(NCO)_p F₅SO-(CH₂)₁₅-(OCH₂CH₂)_m-OCOCH=CH₂; F₅SO-(CH₂)₁₅-(OCH₂CH₂)_m-OCH=CH₂; F₅SO-(CH₂)₁₅-(OCH₂CH₂)_m-OAr(NCO)_p F₅SO-(CH₂)₁₆-(OCH₂CH₂)_m-OCOCH=CH₂; F₅SO-(CH₂)₁₆-(OCH₂CH₂)_m-OCH=CH₂; F₅SO-(CH₂)₁₆-(OCH₂CH₂)_m-OAr(NCO)_p F₅SO-(CH₂)₁₇-(OCH₂CH₂)_m-OCOCH=CH₂; F₅SO-(CH₂)₁₇-(OCH₂CH₂)_m-OCH=CH₂; F₅SO-(CH₂)₁₇-(OCH₂CH₂)_mOAr(NCO)_p F₅SO-(CH₂)₁₈-(OCH₂CH₂)_m-OCOCH=CH₂; F₅SO-(CH₂)₁₈-(OCH₂CH₂)_m-OCH=CH₂; F₅SO-(CH₂)₁₈-(OCH₂CH₂)_m-OAr(NCO)_p F₅SO-(CH₂)₁₉-(OCH₂CH₂)_m-OCOCH=CH₂; F₅SO-(CH₂)₁₉-(OCH₂CH₂)_m-OCH=CH₂; F₅SO-(CH₂)₁₉-(OCH₂CH₂)_m-OAr(NCO)_p F₅SO-(CH₂)₂₀-(OCH₂CH₂)_m-OCOCH=CH₂; F₅SO-(CH₂)₂₀-(OCH₂CH₂)_m-OCH=CH₂; F₅SO-(CH₂)₂₀-(OCH₂CH₂)_m-OAr(NCO)_p F₅SO-(CH₂)₂₁-(OCH₂CH₂)_m-OCOCH=CH₂; F₅SO-(CH₂)₂₁-(OCH₂CH₂)_m-OCH=CH₂; F₅SO-(CH₂)₂₁-(OCH₂CH₂)_m-OAr(NCO)_p F₅SO-(CH₂)₂₂-(OCH₂CH₂)_m-OCOCH=CH₂; F₅SO-(CH₂)₂₂-(OCH₂CH₂)_m-OCH=CH₂; F₅SO-(CH₂)₂₂-(OCH₂CH₂)_m-OAr(NCO)_p F₅SO-(CH₂)₂₃-(OCH₂CH₂)_m-OCOCH=CH₂; F₅SO-(CH₂)₂₃-(OCH₂CH₂)_m-OCH=CH₂; F₅SO-(CH₂)₂₃-(OCH₂CH₂)_m-OAr(NCO)_p F₅SO-(CH₂)₂₄-(OCH₂CH₂)_m-OCOCH=CH₂; F₅SO-(CH₂)₂₄-(OCH₂CH₂)_m-OCH=CH₂; F₅SO-(CH₂)₂₄-(OCH₂CH₂)_m-OAr(NCO)_p F₅SO-(CH₂)₄-N⁺R¹R²R³Z^–; F₅SO-(CH₂)₄-P⁺R¹R²R³Z^–; F₅SO-(CH₂)₄-O-Glucosid F₅SO-(CH₂)₅-N⁺R¹R²R³Z^–; F₅SO-(CH₂)₅-P⁺R¹R²R³Z^-; F₅SO-(CH₂)₅-O-Glucosid F₅SO-(CH₂)₆-N⁺R¹R²R³Z^–; F₅SO-(CH₂)₆-P⁺R¹R²R³Z^–; F₅SO-(CH₂)₆-O-Glucosid F₅SO-(CH₂)₇-N⁺R¹R²R³Z^–; F₅SO-(CH₂)₇-P⁺R¹R²R³Z^-; F₅SO-(CH₂)₇-O-Glucosid F₅SO-(CH₂)₈-N⁺R¹R²R³Z^–; F₅SO-(CH₂)₈-P⁺R¹R²R³Z^–; F₅SO-(CH₂)₈-O-Glucosid F₅SO-(CH₂)₉-N⁺R¹R²R³Z^–; F₅SO-(CH₂)₉-P⁺R¹R²R³Z^–; F₅SO-(CH₂)₉-O-Glucosid F₅SO-(CH₂)₁₀-N⁺R¹R²R³Z^–; F₅SO-(CH₂)₁₀-P⁺R¹R²R³Z^–; F₅SO-(CH₂)₁₀-O-Glucosid F₅SO-(CH₂)₁₁-N⁺R¹R²R³Z^–; F₅SO-(CH₂)₁₁-P⁺R¹R²R³Z^–; F₅SO-(CH₂)₁₁-O-Glucosid F₅SO-(CH₂)₁₂-N⁺R¹R²R³Z^–; F₅SO-(CH₂)₁₂-P⁺R¹R²R³Z^–; F₅SO-(CH₂)₁₂-O-Glucosid F₅SO-(CH₂)₁₃-N⁺R¹R²R³Z^–; F₅SO-(CH₂)₁₃-P⁺R¹R²R³Z^–; F₅SO-(CH₂)₁₃-O-Glucosid F₅SO-(CH₂)₁₄-N⁺R¹R²R³Z^–; F₅SO-(CH₂)₁₄-P⁺R¹R²R³Z^–; F₅SO-(CH₂)₁₄-O-Glucosid F₅SO-(CH₂)₁₅-N⁺R¹R²R³Z^–; F₅SO-(CH₂)₁₅-P⁺R¹R²R³Z^–; F₅SO-(CH₂)₁₅-O-Glucosid F₅SO-(CH₂)₁₆-N⁺R¹R²R³Z^–; F₅SO-(CH₂)₁₆-P⁺R¹R²R³Z^–; F₅SO-(CH₂)₁₆-O-Glucosid F₅SO-(CH₂)₁₇-N⁺R¹R²R³Z^–; F₅SO-(CH₂)₁₇-P⁺R¹R²R³Z^–; F₅SO-(CH₂)₁₇-O-Glucosid F₅SO-(CH₂)₁₈-N⁺R¹R²R³Z^–; F₅SO-(CH₂)₁₈-P⁺R¹R²R³Z^–; F₅SO-(CH₂)₁₈-O-Glucosid F₅SO-(CH₂)₁₉-N⁺R¹R²R³Z^–; F₅SO-(CH₂)₁₉-P⁺R¹R²R³Z^–; F₅SO-(CH₂)₁₉-O-Glucosid F₅SO-(CH₂)₂₀-N⁺R¹R²R³Z^–; F₅SO-(CH₂)₂₀-P⁺R¹R²R³Z^–; F₅SO-(CH₂)₂₀-O-Glucosid F₅SO-(CH₂)₂₁-N⁺R¹R²R³Z^–; F₅SO-(CH₂)₂₁-P⁺R¹R²R³Z^–; F₅SO-(CH₂)₂₁-O-Glucosid F₅SO-(CH₂)₂₂-N⁺R¹R²R³Z^–; F₅SO-(CH₂)₂₂-P⁺R¹R²R³Z^–; F₅SO-(CH₂)₂₂-O-Glucosid F₅SO-(CH₂)₂₃-N⁺R¹R²R³Z^–; F₅SO-(CH₂)₂₃-P⁺R¹R²R³Z^–; F₅SO-(CH₂)₂₃-O-Glucosid F₅SO-(CH₂)₂₄-N⁺R¹R²R³Z^–; F₅SO-(CH₂)₂₄-P⁺R¹R²R³Z^–; F₅SO-(CH₂)₂₄-O-Glucosid In a further aspect, the object of the invention was surprisingly achieved by providing compounds selected from the group consisting of:

(EtO) ₃ Si (CH ₂ ) OSF ₅ , F ₅ SO (CH _{2) 4} -COOH; F ₅ SO- (CH ₂ ) ₄ -SO ₃ H; F ₅ SO- (CH ₂ ) ₄ -O-SO ₃ H F ₅ SO (CH _{2) 5} -COOH; F ₅ SO- (CH ₂ ) ₅ -SO ₃ H; F ₅ SO- (CH ₂ ) ₅ -O-SO ₃ H F ₅ SO (CH _{2) 6} -COOH; F ₅ SO- (CH ₂ ) ₆ -SO ₃ H; F ₅ SO- (CH ₂ ) ₆ -O-SO ₃ H F ₅ SO (CH _{2) 7} -COOH; F ₅ SO- (CH ₂ ) ₇ -SO ₃ H; F ₅ SO- (CH ₂ ) ₇ -O-SO ₃ H F ₅ SO (CH _{2) 8} -COOH; F ₅ SO- (CH ₂ ) ₈ -SO ₃ H; F ₅ SO- (OH ₂ ) ₈ -O-SO ₃ H F ₅ SO (CH _{2) 9} -COOH; F ₅ SO- (CH ₂ ) ₉ -SO ₃ H; F ₅ SO- (CH ₂ ) ₉ -O-SO ₃ H F ₅ SO (CH _{2) 10} -COOH; F ₅ SO- (CH ₂ ) ₁₀ -SO ₃ H; F ₅ SO- (CH ₂ ) ₁₀ -O-SO ₃ H F ₅ SO (CH _{2) 11} -COOH; F ₅ SO- (CH ₂ ) ₁₁ -SO ₃ H; F ₅ SO- (CH ₂ ) ₁₁ -O-SO ₃ H F ₅ SO (CH _{2) 12} -COOH; F ₅ SO- (CH ₂ ) ₁₂ -SO ₃ H; F ₅ SO- (CH ₂ ) ₁₂ -O-SO ₃ H F ₅ SO (CH _{2) 13} -COOH; F ₅ SO- (CH ₂ ) ₁₃ -SO ₃ H; F ₅ SO- (CH ₂ ) ₁₃ -O-SO ₃ H F ₅ SO (CH _{2) 14} -COOH; F ₅ SO- (CH ₂ ) ₁₄ -SO ₃ H; F ₅ SO- (CH ₂ ) ₁₄ -O-SO ₃ H F ₅ SO (CH _{2) 15} -COOH; F ₅ SO- (CH ₂ ) ₁₅ -SO ₃ H; F ₅ SO- (CH ₂ ) ₁₅ -O-SO ₃ H F ₅ SO (CH _{2) 16} -COOH; F ₅ SO- (CH ₂ ) ₁₆ -SO ₃ H; F ₅ SO- (CH ₂ ) ₁₆ -O-SO ₃ H F ₅ SO (CH _{2) 17} -COOH; F ₅ SO- (CH ₂ ) ₁₇ -SO ₃ H; F ₅ SO- (CH ₂ ) ₁₇ -O-SO ₃ H F ₅ SO (CH _{2) 18} -COOH; F ₅ SO- (CH ₂ ) ₁₈ -SO ₃ H; F ₅ SO- (CH ₂ ) ₁₈ -O-SO ₃ H F ₅ SO (CH _{2) 19} -COOH; F ₅ SO- (CH ₂ ) ₁₉ -SO ₃ H; F ₅ SO- (CH ₂ ) ₁₉ -O-SO ₃ H F ₅ SO (CH _{2) 20} -COOH; F ₅ SO- (CH ₂ ) ₂₀ -SO ₃ H; F ₅ SO- (CH ₂ ) ₂₀ -O-SO ₃ H F ₅ SO (CH _{2) 21} -COOH; F ₅ SO- (CH ₂ ) ₂₁ -SO ₃ H; F ₅ SO- (CH ₂ ) ₂₁ -O-SO ₃ H F ₅ SO (CH _{2) 22} -COOH; F ₅ (SO- (CH ₂ ) ₂₂ -SO ₃ H; F ₅ SO- (CH ₂ ) ₂₂ -O-SO ₃ H F ₅ SO (CH _{2) 23} -COOH; F ₅ SO- (CH ₂ ) ₂₃ -SO ₃ H; F ₅ SO- (CH ₂ ) ₂₃ -O-SO ₃ H F ₅ SO (CH _{2) 24} -COOH; F ₅ SO- (CH ₂ ) ₂₄ -SO ₃ H; F ₅ SO- (CH ₂ ) ₂₄ -O-SO ₃ H F ₅ SO- (CH ₂ ) ₄ -COONa; F ₅ SO- (CH ₂ ) ₄ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₄ -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₅ -COONa; F ₅ SO- (CH ₂ ) ₅ -SO ₃ Na; F ₅ SO- (OH ₂ ) ₅ -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₆ -COONa; F ₅ SO- (CH ₂ ) ₆ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₆ -O-SO ₃ Na F ₅ SO (CH _{2) 7} -COONa; F ₅ SO- (CH ₂ ) ₇ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₇ -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₈ -COONa; F ₅ SO- (CH ₂ ) ₈ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₈ -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₉ -COONa; F ₅ SO- (CH ₂ ) ₉ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₉ -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₁₀ -COONa; F ₅ SO- (CH ₂ ) ₁₀ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₁₀ -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₁₁ -COONa; F ₅ SO- (CH ₂ ) ₁₁ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₁₁ -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₁₂ -COONa; F ₅ SO- (CH ₂ ) ₁₂ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₁₂ -O-SO ₃ Na F ₅ SO (CH _{2) 13} COONa; F ₅ SO- (CH ₂ ) ₁₃ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₁₃ -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₁₄ -COONa; F ₅ SO- (CH ₂ ) ₁₄ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₁₄ -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₁₅ -COONa; F ₅ SO- (CH ₂ ) ₁₅ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₁₅ -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₁₆ -COONa; F ₅ SO- (CH ₂ ) ₁₆ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₁₆ -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₁₇ -COONa; F ₅ SO- (CH ₂ ) ₁₇ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₁₇ -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₁₈ -COONa; F ₅ SO- (CH ₂ ) ₁₈ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₁₈ -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₁₉ -COONa; F ₅ SO- (CH ₂ ) ₁₉ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₁₉ -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₂₀ -COONa; F ₅ SO- (CH ₂ ) ₂₀ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₂₀ -O-SO ₃ Na F ₅ SO (CH _{2) 21} COONa; F ₅ SO- (CH ₂ ) ₂₁ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₂₁ -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₂₂ -COONa; F ₅ SO- (CH ₂ ) ₂₂ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₂₂ -O-SO ₃ Na F ₅ SO (CH _{2) 23} COONa; F ₅ SO- (CH ₂ ) ₂₃ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₂₃ -O-SO ₃ Na F ₅ SO (CH _{2) 24} COONa; F ₅ SO- (CH ₂ ) ₂₄ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₂₄ -O-SO ₃ Na F ₅ SO (phenyl) -COOH; F ₅ SO- (phenyl) -SO ₃ H; F ₅ SO- (phenyl) -O-SO ₃ H F ₅ SO-CH ₂ - (phenyl) -COOH; F ₅ SO-CH ₂ - (phenyl) -SO ₃ H; F ₅ SO-CH ₂ - (phenyl) -O-SO ₃ H F ₅ SO-CH ₂ -O- (phenyl) -COOH; F ₅ SO-CH ₂ -O- (phenyl) -SO ₃ H; F ₅ SO-CH ₂ -O- (phenyl) -O-SO ₃ H F ₅ SO- (CH ₂ ) ₂ -O- (phenyl) -COOH; F ₅ SO- (CH ₂ ) ₂ -O- (phenyl) -SO ₃ H; F ₅ SO- (CH ₂ ) ₂ -O- (phenyl) -O-SO ₃ H F ₅ SO- (CH ₂ ) ₃ -O- (phenyl) -COOH; F ₅ SO- (CH ₂ ) ₃ -O- (phenyl) -SO ₃ H; F ₅ SO- (CH ₂ ) ₃ -O- (phenyl) -O-SO ₃ H F ₅ SO- (CH ₂ ) ₄ -O- (phenyl) -COOH; F ₅ SO- (CH ₂ ) ₄ -O- (phenyl) -SO ₃ H; F ₅ SO- (CH ₂ ) ₄ -O- (phenyl) -O-SO ₃ H F ₅ SO- (CH ₂ ) ₅ -O- (phenyl) -COOH; F ₅ SO- (CH ₂ ) ₅ -O- (phenyl) -SO ₃ H; F ₅ SO- (CH ₂ ) ₅ -O- (phenyl) -O-SO ₃ H F ₅ SO- (CH ₂ ) ₆ -O- (phenyl) -COOH; F ₅ SO- (CH ₂ ) ₆ -O- (phenyl) -SO ₃ H; F ₅ SO- (CH ₂ ) ₆ -O- (phenyl) -O-SO ₃ H F ₅ SO- (CH ₂ ) ₇ -O- (phenyl) -COOH; F ₅ SO- (CH ₂ ) ₇ -O- (phenyl) -SO ₃ H; F ₅ SO- (CH ₂ ) ₇ -O- (phenyl) -O-SO ₃ H F ₅ SO- (CH ₂ ) ₈ -O- (phenyl) -COOH; F ₅ SO- (CH ₂ ) ₈ -O- (phenyl) -SO ₃ H; F ₅ SO- (CH ₂ ) ₈ -O- (phenyl) -O-SO ₃ H F ₅ SO (CH _{2) 9} -O- (phenyl) -COOH; F ₅ SO- (CH ₂ ) ₉ -O- (phenyl) -SO ₃ H; F ₅ SO- (CH ₂ ) ₉ -O- (phenyl) -O-SO ₃ H F ₅ SO- (CH ₂ ) ₁₀ -O- (phenyl) -COOH; F ₅ SO- (CH ₂ ) ₁₀ -O- (phenyl) -SO ₃ H; F ₅ SO- (CH ₂ ) ₁₀ -O- (phenyl) -O-SO ₃ H F ₅ SO (phenyl) -COONa; F ₅ SO- (phenyl) -SO ₃ Na; F ₅ SO- (phenyl) -O-SO ₃ Na F ₅ SO-CH ₂ - (phenyl) -COONa; F ₅ SO-CH ₂ - (phenyl) -SO ₃ Na; F ₅ SO-CH ₂ - (phenyl) -O-SO ₃ Na F ₅ SO-CH ₂ -O- (phenyl) -COONa; F ₅ SO-CH ₂ -O- (phenyl) -SO ₃ Na; F ₅ SO-CH ₂ -O- (phenyl) -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₂ -O- (phenyl) -COONa; F ₅ SO- (CH ₂ ) ₂ -O- (phenyl) -SO ₃ Na; F ₅ SO- (CH ₂ ) ₂ -O- (phenyl) -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₃ -O- (phenyl) -COONa; F ₅ SO- (CH ₂ ) ₃ -O- (phenyl) -SO ₃ Na; F ₅ SO- (CH ₂ ) ₃ -O- (phenyl) -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₄ -O- (phenyl) -COONa; F ₅ SO- (CH ₂ ) ₄ -O- (phenyl) -SO ₃ Na; F ₅ SO- (CH ₂ ) ₄ -O- (phenyl) -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₅ -O- (phenyl) -COONa; F ₅ SO- (CH ₂ ) ₅ -O- (phenyl) -SO ₃ Na; F ₅ SO- (CH ₂ ) ₅ -O- (phenyl) -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₆ -O- (phenyl) -COONa; F ₅ SO- (CH ₂ ) ₆ -O- (phenyl) -SO ₃ Na; F ₅ SO- (CH ₂ ) ₆ -O- (phenyl) -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₇ -O- (phenyl) -COONa; F ₅ SO- (CH ₂ ) ₇ -O- (phenyl) -SO ₃ Na; F ₅ SO- (CH ₂ ) ₇ -O- (phenyl) -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₈ -O- (phenyl) -COONa; F ₅ SO- (CH ₂ ) ₈ -O- (phenyl) -SO ₃ Na; F ₅ SO- (CH ₂ ) ₈ -O- (phenyl) -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₉ -O- (phenyl) -COONa; F ₅ SO- (CH ₂ ) ₉ -O- (phenyl) -SO ₃ Na; F ₅ SO- (CH ₂ ) ₉ -O- (phenyl) -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₁₀ -O- (phenyl) -COONa; F ₅ SO- (CH ₂ ) ₁₀ -O- (phenyl) -SO ₃ Na; F ₅ SO- (CH ₂ ) ₁₀ -O- (phenyl) -O-SO ₃ Na F ₅ SO (CH _{2) 4} -OH; F ₅ SO- (CH ₂ ) ₄ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₄ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 5} -OH; F ₅ SO- (CH ₂ ) ₅ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₅ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 6} -one; F ₅ SO- (CH ₂ ) ₆ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₆ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 7} OH; F ₅ SO- (CH ₂ ) ₇ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₇ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 8} -OH; F ₅ SO- (CH ₂ ) ₈ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₈ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 9} -OH; F ₅ SO- (CH ₂ ) ₉ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₉ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 10} -OH; F ₅ SO- (CH ₂ ) ₁₀ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₁₀ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 11} -OH; F ₅ SO- (CH ₂ ) ₁₁ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₁₁ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 12} -OH; F ₅ SO- (CH ₂ ) ₁₂ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₁₂ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 13} -OH; F ₅ SO- (CH ₂ ) ₁₃ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₁₃ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 14} -OH; F ₅ SO- (CH ₂ ) ₁₄ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₁₄ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 15} -OH; F ₅ SO- (CH ₂ ) ₁₅ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₁₅ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 16} -OH; F ₅ SO- (CH ₂ ) ₁₆ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₁₆ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 17} -OH; F ₅ SO- (CH ₂ ) ₁₇ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₁₇ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 18} -OH; F ₅ SO- (CH ₂ ) ₁₈ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₁₈ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 19} -OH; F ₅ SO- (CH ₂ ) ₁₉ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₁₉ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 20} -OH; F ₅ SO- (CH ₂ ) ₂₀ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₂₀ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 21} -OH; F ₅ SO- (CH ₂ ) ₂₁ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₂₁ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 22} -OH; F ₅ SO- (CH ₂ ) ₂₂ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₂₂ - (OCH ₂ OH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 23} -OH; F ₅ SO- (CH ₂ ) ₂₃ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₂₃ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 24} -OH; F ₅ SO- (CH ₂ ) ₂₄ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₂₄ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO- (CH ₂ ) ₄ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₄ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₄ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₅ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₅ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₅ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₆ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₆ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₆ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₇ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₇ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₇ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₈ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₈ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₈ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₉ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₉ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₉ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₁₀ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₀ - (OCH ₂ CH ₂ ) _m OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₀ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₁₁ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₁ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₁ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₁₂ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₂ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₂ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₁₃ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₃ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₃ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₁₄ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₄ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₄ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₁₅ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₅ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₅ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₁₆ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₆ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₆ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₁₇ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₇ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₇ - (OCH ₂ CH ₂ ) _m OAr (NCO) _p F ₅ SO- (CH ₂ ) ₁₈ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₈ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₈ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₁₉ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₉ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₉ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₂₀ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₂₀ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₂₀ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₂₁ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₂₁ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₂₁ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₂₂ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₂₂ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₂₂ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₂₃ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₂₃ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₂₃ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₂₄ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₂₄ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₂₄ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₄ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₄ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₄ -O-glucoside F ₅ SO- (CH ₂ ) ₅ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₅ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₅ -O-glucoside F ₅ SO- (CH ₂ ) ₆ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₆ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₆ -O-glucoside F ₅ SO- (CH ₂ ) ₇ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₇ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₇ -O-glucoside F ₅ SO- (CH ₂ ) ₈ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₈ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₈ -O-glucoside F ₅ SO- (CH ₂ ) ₉ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₉ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₉ -O-glucoside F ₅ SO- (CH ₂ ) ₁₀ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₀ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₀ -O-glucoside F ₅ SO- (CH ₂ ) ₁₁ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₁ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₁ -O-glucoside F ₅ SO- (CH ₂ ) ₁₂ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₂ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₂ -O-glucoside F ₅ SO- (CH ₂ ) ₁₃ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₃ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₃ -O-glucoside F ₅ SO- (CH ₂ ) ₁₄ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₄ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₄ -O-glucoside F ₅ SO- (CH ₂ ) ₁₅ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₅ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₅ -O-glucoside F ₅ SO- (CH ₂ ) ₁₆ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₆ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₆ -O-glucoside F ₅ SO- (CH ₂ ) ₁₇ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₇ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₇ -O-glucoside F ₅ SO- (CH ₂ ) ₁₈ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₈ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₈ -O-glucoside F ₅ SO- (CH ₂ ) ₁₉ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₉ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₉ -O-glucoside F ₅ SO- (CH ₂ ) ₂₀ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₂₀ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₂₀ -O-glucoside F ₅ SO- (CH ₂ ) ₂₁ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₂₁ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₂₁ -O-glucoside F ₅ SO- (CH ₂ ) ₂₂ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₂₂ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₂₂ -O-glucoside F ₅ SO- (CH ₂ ) ₂₃ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₂₃ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₂₃ -O-glucoside F ₅ SO- (CH ₂ ) ₂₄ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₂₄ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₂₄ -O-glucoside

All of the compounds generically or explicitly disclosed above, including the preferred subset (s) of the formula (I) disclosed herein and explicitly disclosed compounds, are hereinafter referred to as compounds of the invention or compounds of the invention.

The nomenclature used herein to define compounds, particularly compounds of the invention, is generally based on the rules of the IUPAC organization for chemical compounds, and in particular organic compounds.

The terms given to illustrate the above compounds of the invention, unless otherwise specified in the specification or claims, always have the following meanings:
The term "unsubstituted" means that the corresponding radical, group or moiety has no substituents.

The term "substituted" means that the corresponding group, group or moiety has one or more substituents. When a group has a plurality of substituents, and a variety of different substituents are given, the substituents are independently selected and need not be equal to each other.

The terms "alkyl" or "A" and other groups having the prefix "alk" for the purposes of this invention refer to acyclic saturated or unsaturated hydrocarbon radicals which may be branched or straight chain and preferably have 1 to 30 carbon atoms, ie C ₁ - C ₃₀ alkanylyl, C ₂ -C ₃₀ -alkenyls and C ₂ -C ₃₀ -alkynyls. Alkenyls have at least one CC double bond and alkynyls at least one CC triple bond. Alkynyls may also have at least one CC double bond. Examples of suitable alkyl radicals are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neo-pentyl, tert-pentyl, 2- or 3-methylpentyl , n-hexyl, 2-hexyl, isohexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, n-icosanyl , n-docosanyl, ethylenyl (vinyl), propenyl (-CH ₂ CH = CH ₂ ; -CH = CH-CH ₃ , -C (= CH ₂ ) -CH ₃ ), butenyl, pentenyl, hexenyl, heptenyl, octenyl, Octadienyl, octadecenyl, octadec-9-enyl, icosenyl, icos-11-enyl, (Z) -iscos-11-enyl, docosenyl, docos-13-enyl, (Z) -docos-13-enyl, ethynyl, propynyl ( -CH ₂ -C≡CH, -C≡C-CH ₃ ), butynyl, pentynyl, hexynyl, heptynyl, octynyl. Particularly preferred is C _1-4 alkyl. A C _1-4 alkyl radical is, for example, a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl.

The term "cycloalkyl" for the purposes of this invention refers to saturated and partially unsaturated non-aromatic cyclic hydrocarbon groups / radicals having from 1 to 3 rings having from 3 to 20, preferably from 3 to 12, most preferably from 3 to 8, carbon atoms. The cycloalkyl radical can also be part of a bicyclic or polycyclic system in which, for example, the cycloalkyl radical via (any) possible (s) and desired (s) ring member (s) having an aryl, heteroaryl or heterocyclyl as here is defined condensed. The bond to the compounds of the general formula can take place via any possible ring member of the cycloalkyl radical. Examples of suitable cycloalkyl radicals are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclodecyl, cyclohexenyl, cyclopentenyl and cyclooctadienyl. Particularly preferred are C ₃ -C 9 cycloalkyl and C ₄ -C ₈ cycloalkyl. A C ₄ -C ₈ -cycloalkyl radical is z. For example, a cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl.

The term "heterocyclyl" for the purposes of this invention refers to a mono- or polycyclic system having 3 to 20, preferably 5 or 6 to 14 ring atoms containing carbon atoms and 1, 2, 3, 4, or 5 heteroatoms, especially nitrogen, oxygen and / or sulfur which are the same or different. The cyclic system may be saturated or mono- or polyunsaturated, but not aromatic. In a cyclic system consisting of at least two rings, the rings may be fused or linked spiro or otherwise. Such "heterocyclyl" radicals can be linked via any ring member. The term "heterocyclyl" also encompasses systems in which the heterocycle is part of a bi- or polycyclic saturated, partially unsaturated and / or aromatic system, as is the case when the heterocycle has any desired and possible ring member of the heterocyclyl radical "Aryl", "cycloalkyl", "heteroaryl" or "heterocyclyl" group as defined herein. The binding to the compounds of the general formula can be effected via any possible ring member of the heterocyclyl radical. Examples of suitable "heterocyclyl" radicals are pyrrolidinyl, thiapyrrolidinyl, piperidinyl, piperazinyl, oxapiperazinyl, oxapiperidinyl, oxadiazolyl, tetrahydrofuryl, imidazolidinyl, thiazolidinyl, tetrahydropyranyl, morpholinyl, tetrahydrothiophenyl, dihydropyranyl, indolinyl, indolinylmethyl, imidazolidinyl, 2-azabicyclo [2.2. 2] octanyl.

The term "aryl" for the purposes of this invention refers to a mono- or polycyclic aromatic hydrocarbon system having 3 to 14, preferably 5 to 14, more preferably 6 to 10 carbon atoms. The term "aryl" also includes systems in which the aromatic cycle is part of a bi- or polycyclic saturated, partially unsaturated and / or aromatic system, as is the case when the aromatic cycle is over any desired and possible ring member of the aryl radical having an "aryl", "cycloalkyl", "heteroaryl" or "heterocyclyl" group as defined herein. The bond to the compounds of the general formula can be made via any possible ring member of the aryl radical. Examples of suitable "aryl" radicals are phenyl, biphenyl, naphthyl, 1-naphthyl, 2-naphthyl and anthracenyl, but also indanyl, indenyl or 1,2,3,4-tetrahydronaphthyl. The most preferred aryl is phenyl.

The term "heteroaryl" for the purposes of this invention refers to a 3-15, preferably 5-14, more preferably 5-, 6- or 7-membered mono- or polycyclic aromatic hydrocarbon radical containing at least 1, optionally also contains 2, 3, 4 or 5 heteroatoms, preferably nitrogen, oxygen and / or sulfur, wherein the heteroatoms are the same or different. The number of nitrogen atoms is preferably 0, 1, 2 or 3 and that of the oxygen and sulfur atoms is independently 0 or 1. The term "heteroaryl" also includes systems in which the aromatic cycle is part of a bi- or polycyclic saturated, partially unsaturated and / or aromatic system, as is the case when the aromatic cycle is over any desired and possible ring member of the heteroaryl group having an "aryl", "cycloalkyl", "heteroaryl" or "heterocyclyl" group as herein is defined condensed. The binding to the compounds of the general formula can be effected via any possible ring member of the heteroaryl radical. Examples of suitable "heteroaryl" radicals are acridinyl, benzodioxinyl, benzimidazolyl, benzisoxazalyl, benzodioxolyl, benzofuranyl, benzothiadiazolyl, benzothiazolyl, benzothienyl, benzoxazolyl, carbazolyl, cinnolinyl, dibenzofuranyl, dihydrobenzothienyl, furanyl, furazanyl, furyl, imidazolyl, indazolyl, indolinyl, indolizinyl, Indolyl, isobenzylfuranyl, isoindolyl, isoquinolinyl, isoquinolyl, isothiazolyl, isoxazolyl, naphthyridinyl, oxadiazolyl, oxazolyl, phenazinyl, phenothiazinyl, phenoxazinyl, phthalazinyl, pteridinyl, purinyl, pyrazinyl, pyrazolyl, pyridazinyl, pyridinyl, pyridyl, pyrimidinyl, pyrimidyl, pyrrolyl, quinazolinyl, Quinolinyl, quinolyl, quinoxalinyl, tetrazolyl, thiadiazolyl, thiazolyl, thienyl, thiophenyl, triazinyl, triazolyl.

For the purposes of the present invention, the terms "alkylcycloalkyl", "cycloalkylalkyl", "alkylheterocyclyl", "heterocyclylalkyl", "alkylaryl", "arylalkyl", "alkylheteroaryl" and "heteroarylalkyl", the alkyl, cycloalkyl, heterocyclyl, aryl and heteroaryl are each as defined above and the cycloalkyl, Heterocyclyl, aryl and heteroaryl via an alkyl radical, preferably C ₁ -C ₈ alkyl, particularly preferably C ₁ -C ₄ alkyl radical is bonded to the compounds of the general formula.

The term "alkyloxy" or "alkoxy" for the purposes of this invention refers to an alkyl radical as defined above attached to an oxygen atom. The binding to the compounds of the general formula takes place via the oxygen atom. Examples are methoxy, ethoxy and n-propyloxy, propoxy, isopropoxy. Preference is given to "C ₁ -C ₄ -alkyloxy" with the specified number of carbon atoms.

The term "cycloalkyloxy" or "cycloalkoxy" for the purposes of this invention refers to a cycloalkyl radical as defined above attached to an oxygen atom. The binding to the compounds of the general formula takes place via the oxygen atom. Examples are cyclopropyloxy cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cycloheptyloxy, cyclooctyloxy. Preferred is "C ₃ -C ₉ cycloalkyloxy" having the specified number of carbon atoms.

The term "heterocyclyloxy" for the purposes of this invention refers to a heterocyclyl radical as defined above attached to an oxygen atom. The binding to the compounds of the general formula takes place via the oxygen atom. Examples are pyrrolidinyloxy, thiapyrrolidinyloxy, piperidinyloxy, piperazinyloxy.

The term "aryloxy" for the purposes of this invention refers to an aryl radical as defined above attached to an oxygen atom. The binding to the compounds of the general formula takes place via the oxygen atom. Examples are phenyloxy, 2-naphthyloxy, 1-naphthyloxy, biphenyloxy, indanyloxy. Preferred is phenyloxy.

The term "heteroaryloxy" for the purposes of this invention refers to a heteroaryl radical as defined above attached to an oxygen atom. The binding to the compounds of the general formula takes place via the oxygen atom. Examples are pyrrolyloxy, thienyloxy, furyloxy, imidazolyloxy, thiazolyloxy.

The term "carbonyl" or "carbonyl moiety" for the purposes of this invention refers to a -C (O) group.

The term "alkylcarbonyl" for the purposes of this invention refers to an "alkyl C (O) -" group wherein alkyl is as defined herein.

The term "alkoxycarbonyl" or "alkyloxycarbonyl" for the purposes of this invention refers to an "alkyl-O-C (O) -" group wherein alkyl is as defined herein.

The term "alkoxyalkyl ^" for the purposes of this invention refers to an "alkyl-O-alkyl" group wherein alkyl is as defined herein.

The term "haloalkyl ^" for the purposes of this invention refers to an alkyl group as defined herein which contains at least one carbon atom substituted with at least one halogen as defined herein.

The term "halogen", "halogen atom", "halo substituent" or "Hal" for the purposes of this invention refers to one or optionally a plurality of fluoro (F, fluoro), bromo (Br, bromo), chloro ( Cl, chloro) or iodine atoms (I, iodo). The terms "dihalo", "trihalogen" and "perhalo" refer to two, three or four substituents, respectively, wherein each substituent may be independently selected from the group consisting of fluoro, chloro, bromo and iodo. "Halogen" preferably means a fluorine, chlorine or bromine atom. Fluorine is particularly preferred when the halogens are substituted on an alkyl (haloalkyl) or alkoxy group (e.g., CF ₃ and CF ₃ O).

The term "hydroxyl" or "hydroxy" refers to an OH group.

The compounds of the present invention may be prepared by methods known to those skilled in the literature.

• (a) Umwandeln des Substituenten U einer Verbindung der Formel (II) U-(Ar)_n1-(O)_n2-(CH₂)_n3-OSF₅ (II) wobei U F, Cl, Br, I oder OH bedeutet und Ar, n1, n2 und n3 die oben angegebene Bedeutung besitzen, in einen Substituenten Z einer Verbindung der Formel (1) Z-(Ar)_n1–(O)_n2–(CH₂)_n3-OSF₅ (I) wobei Z, Ar, n1, n2 und n3 die oben angegebene Bedeutung besitzen, z. B. durch Oxidation, Veresterung oder S_N2-Reaktion, und optional
• (b) Umwandeln eines Substituenten Z mit oben angegebener Bedeutung in einen anderen Substituenten Z mit oben angegebener Bedeutung, z. B. durch Ersetzen einer Hydroxyl-Gruppe durch eine -O(CH₂CH₂O)_nH Gruppe oder Einführung einer Natriumsulfat-Gruppe.

In a further aspect, the object of the invention was surprisingly achieved by providing a process for the preparation of compounds of the invention comprising the steps:

• (a) converting the substituent U of a compound of the formula (II) U- (Ar) _n1 - (O) _n2 - (CH _{2) n3} -OSF ₅ (II) where UF, Cl, Br, I or OH and Ar, n1, n2 and n3 have the abovementioned meaning, into a substituent Z of a compound of the formula (1) Z- (Ar) _n1 - (O) _n2 - (CH _{2) n3} -OSF ₅ (I) wherein Z, Ar, n1, n2 and n3 have the abovementioned meaning, z. By oxidation, esterification or S _N2 reaction, and optionally
• (B) converting a substituent Z as defined above into another substituent Z as defined above, z. By replacing a hydroxyl group with a -O (CH ₂ CH ₂ O) _n H group or introducing a sodium sulfate group.

• – eine Oberflächenaktivität, die der konventioneller Kohlenwasserstoff-Tenside hinsichtlich Effizienz und/oder Effektivität gleich oder überlegen ist,
• – biologische und/oder abiotische Abbaubarkeit der Substanzen ohne Bildung persistenter perfluorierter Abbauprodukte wie PFOA (Perfluoroctansäure) oder PFOS (Perfluoroctansulfonat). Die biologische und abiotische Abbaubarkeit der erfindungsgemäßen Substanzen ist erheblich besser, da der Kohlenwasserstoffteil leicht metabolisiert werden kann. Die letztendlich verbleibende Pentafluorschwefelsäure ( K. Seppelt, Angew. Chem. 1976, 88, 56–59 ) fragmentiert spontan zu SOF₄ und HF und wird schließlich zu HF und Schwefelsäure hydrolysiert.
• – schwache Schaumbildung,
• – gute Verarbeitbarkeit in Formulierungen und/oder
• – Lagerstabilität.

Advantages of the compounds according to the invention can be in particular:

• A surface activity equal or superior to conventional hydrocarbon surfactants in terms of efficiency and / or effectiveness,
• - biological and / or abiotic degradability of the substances without formation of persistent perfluorinated degradation products such as PFOA (perfluorooctanoic acid) or PFOS (perfluorooctanesulfonate). The biological and abiotic degradability of the substances according to the invention is considerably better, since the hydrocarbon part can be easily metabolized. The final remaining pentafluorosulphuric acid ( K. Seppelt, Angew. Chem. 1976, 88, 56-59 ) fragments spontaneously to SOF ₄ and HF and is finally hydrolyzed to HF and sulfuric acid.
• - weak foaming,
• Good processability in formulations and / or
• - storage stability.

The compounds according to the invention preferably have a particular surface activity.

A second object of the present invention is the use of compounds according to the invention as surfactants, for example for improving the flow behavior and the wetting power of coating formulations.

In this case, the preferred embodiments of the compounds according to the invention described above can be used particularly advantageously. The compounds according to the invention can also be used as mixtures of isomers (mixtures of constitution and / or isomers of isomers). In particular, diastereomeric and / or enantiomeric mixtures are possible.

Areas of use are, for example, the use of the compounds according to the invention as additives in surface coating preparations, such as paints, lacquers, protective coatings, special coatings in electronic or semiconductor applications (for example, photoresists, top anti-reflective coatings, bottom anti-reflective coatings) or in optical applications (eg B. photographic coatings, coatings of optical elements) or in additive formulations for the addition of appropriate preparations.

The compounds according to the invention for the application are usually incorporated in appropriately designed preparations. Corresponding agents containing at least one compound according to the invention are likewise provided by the present invention. Such agents preferably contain a carrier suitable for the respective intended use, as well as optionally further active ingredients and / or optionally adjuvants. Preferred agents are color and lacquer preparations and printing inks.

• – Polykondensationsharze wie Alkydharze, gesättigt/ungesättigte Polyester,
• – Polyamide/imide, Silikonharze; Phenolharze; Harnstoffharze und Melaminharze,
• – Polyadditionsharze wie Polyurethane und Epoxidharze,
• – Polymerisationsharze wie Polyolefine, Polyvinylverbindungen und Polyacrylate.

In addition, water-based coating formulations containing at least one of the compounds according to the invention alone or in a mixture with other surfactants are also the subject of the present invention. Coating formulations based on the following synthetic film formers are preferably used:

• Polycondensation resins such as alkyd resins, saturated / unsaturated polyesters,
• - polyamides / imides, silicone resins; Phenol resins; Urea resins and melamine resins,
• Polyaddition resins such as polyurethanes and epoxy resins,
• - Polymerization resins such as polyolefins, polyvinyl compounds and polyacrylates.

In addition, the compounds of the invention are also suitable for use in paints based on natural substances and modified natural products. Preference is given to lacquers based on oils, polysaccharides such as starch and cellulose and also based on natural resins such as cyclic oligoterpenes, polyterpenes and / or shellac. The compounds according to the invention can be used both in physically curing (thermoplastics) and in crosslinking (elastomers and duromers) aqueous coating systems. The compounds according to the invention preferably improve the flow and wetting properties of the coating systems.

Another area of use of the compounds according to the invention lies in production processes of polymers, in particular of fluoropolymers. Important technical methods for the preparation of fluoropolymers such. B. polytetrafluoroethylene (PTFE) are z. B. emulsion and suspension polymerization. Suspension and emulsion polymerization processes are common polymerization processes well known to those skilled in the art. In suspension and emulsion polymerization processes, the system always contains at least four components: (predominantly) water-insoluble monomer, water, dispersant or emulsifier and initiator. The implementation of said polymerization is familiar to the expert. In this process, the polymer is prepared in an autoclave containing water or the corresponding, usually gaseous, monomers, initiators, surfactants and other auxiliaries, with stirring and constant temperature and pressure control. The compounds according to the invention are suitable as surfactants to keep the very hydrophobic fluoropolymer droplets or particles dispersed in the aqueous solution.

In addition, the compounds of the present invention can be used in water repellents, oil repellents, wetting agents, stain and soil protectants, stain releases, antifoggants, lubricants, defoamers, deaerators, drying accelerators, abrasion and mechanical durability improvers, and antistatics, especially in the treatment of textiles (in particular clothing, carpets and rugs, upholstery coverings in furniture and automobiles) and hard surfaces (in particular kitchen surfaces, sanitary facilities, tiles, glass), non-woven textile materials, leather goods, papers and cartons, wood and wood-based materials, mineral substrates such as Stone, cement, concrete, plaster, ceramics (glazed and unglazed bricks, stoneware, porcelain) and glasses, as well as for plastics and metallic substrates. For metallic substrates, the use in anticorrosion agents is additionally the subject matter of the claims. For plastics and molds for plastics processing, the use in mold release agents is additionally subject matter of the claims. In the case of detergents and stain removers, the use as detergents or soil emulsifying and dispersing agents is additionally the subject matter of the claims.

Furthermore, the compounds of the invention can be used as antimicrobial agent, in particular as a reagent for the antimicrobial surface modification.

Another area of use of the compounds according to the invention is additives or additive formulations in printing inks, having one or more of the following functions: defoamer, deaerator, friction control agent, wetting agent, leveling agent, pigment compatibility improver, printing resolution improver, drying accelerator.

The compounds according to the invention can also be used as foam stabilizers and / or to support film formation, in particular in aqueous film-forming fire-extinguishing foams, both synthetic and protein-based, also for alcohol-resistant formulations (AFFF and AFFF-AR, FP, FFFP and FFFP-AR).

Furthermore, the compounds according to the invention can be used as additives in polymeric materials (plastics) with one or more of the following functions: lubricants, internal friction reducers, UV stabilizers, water repellents, oil repellents, stain and soil protectants, fillers, flame retardants , Migration inhibitor (especially against migration of plasticizers), anti-fogging agents.

In addition, the compounds according to the invention are also suitable for use as additives in liquid media for cleaning, etching, reactive modification and / or substance deposition on metal surfaces (in particular electroplating and anodization) or semiconductor surfaces (in particular for semiconductor photolithography: developer, stripper, edge Bead Remover, etching and cleaning agents), suitable as a wetting agent and / or improvers of the quality of deposited films.

In addition, the compounds useful according to the invention as surfactant for washing and cleaning applications, as well as for use as additives / surfactants in cosmetic products such. Hair and body care products (eg shampoos, hair conditioners and hair conditioners), foam baths, creams or lotions having one or more of the following functions: emulsifiers, wetting agents, foaming agents, lubricants, antistatic agents, skin fats resistance enhancers.

The compounds of the invention further comprise the use as additives in herbicides, pesticides and fungicides having one or more of the following functions: substrate wetting agent, adjuvant, foam inhibitor, dispersing agent, emulsion stabilizer.

In addition, the compounds according to the invention can also be used as additives in deicing or anti-icing agents.

In addition, the compounds of the invention are useful as additives in ore processing formulations, particularly flotation and leaching solutions, having one or more of the following functions: wetting agents, foaming agents, foam inhibitors, and as additives in petroleum source stimulation agents, with one or more of the following Functions: Wetting agent, foaming agent, emulsifier.

Another area of use of the compounds according to the invention is the use as additives in adhesives, with one or more of the following functions: wetting agent, penetrating agent, substrate adhesion promoter, defoamer.

Furthermore, the compounds according to the invention can be used as additives in lubricants and hydraulic fluids, with one or more of the following functions: wetting agent, corrosion inhibitor. In the case of lubricants, the use as a dispersant (in particular for fluoropolymer particles) is additionally the subject of the claims.

Also, the compounds of the invention may be used as additives in putties and fillers, with one or more of the following functions: water repellents, oil repellents, soil protectants, weatherability improvers, UV stabilizers, silicone bleed-off agents.

All uses of compounds according to the invention to be used according to the invention are the subject of the present invention. The particular use of surfactants for the stated purposes is known to the person skilled in the art, so that the use of the compounds to be used according to the invention causes no problems. The compounds of the formula (I) are preferably used in color and lacquer preparations and in the production processes of polymers, in particular of fluoropolymers.

In a further aspect, the object of the invention was surprisingly achieved by providing the use of compounds of the invention as surfactants, as hydrophobing or Oleophobiermittel, in particular in the surface modification of textiles, paper, glass, porous building materials or adsorbents, as an antistatic agent, in particular in the treatment of Textiles such as clothing, carpets and rugs, upholstery coverings in furniture and automobiles, non-woven textile materials, leather goods, papers and cartons, wood and wood-based materials, mineral substrates such as stone, cement, concrete, plaster, ceramics, such as glazed and unglazed bricks , Stoneware, porcelain, and glasses, as well as for plastics and metallic substrates, as additives in surface coating formulations, such as printing inks, paints, paints, coatings, photographic coatings, special coatings for semiconductor photolithography, such as photoresists, top antirefle ctive coatings, bottom antireflective coatings, or in additive formulations for the addition of appropriate preparations, as a foam stabilizer and / or to aid film formation, in particular in fire-extinguishing foams, as an interface mediator or emulsifier, in particular for the production of fluoropolymers, or as an antimicrobial agent, in particular as a reagent for the antimicrobial surface modification.

In a further aspect, the object of the invention was surprisingly achieved by providing an agent containing at least one compound of the invention.

In a preferred embodiment, an agent containing at least one compound of the invention is provided, characterized in that a carrier suitable for the respective intended use and optionally further specific active substances are contained.

In a preferred embodiment, an agent as set forth above is provided characterized in that the agent is paint and lacquer preparations, fire-extinguishing agents, lubricants, detergents and cleaners, de-icers or water repellents for textile finishing or glass treatment.

In a further aspect, the object of the invention was surprisingly achieved by providing intermediates according to formula (III) V (Ar) _n1 - (O) _n2 - (CH _{2) n3} -OSF ₅ (III) in which:
V is selected from the group consisting of H ₂ C = CH-, alkyl-HC = CH, Cl, Br, I, OH, -OCH ₂ -phenyl, -BR ₂ , -SiR ₃ , -O ₃ SR, wherein R is alkyl, aryl, F, CF ₃ , phenyl-CH ₃ ,
Ar is an aromatic mono- or bicyclic carbon ring having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms,
n1, n2 independently of one another denote 0 or 1, preferably 0,
n3 0-1000, preferably 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, particularly preferably 2, 3, 4, 5 or 6 means.

Brief description of the illustrations

1 shows the biodegradability of the test substance 30 (% DOC decrease).

2 shows the release of sulfate and fluoride (ppm) for test substance 30,

3 shows the release of sulfate and fluoride (%) for test substance 30.

In addition to the preferred compounds mentioned in the description, their use, compositions and methods, further preferred combinations of the subject matters of the invention are disclosed in the claims.

The disclosures in the cited references are hereby also expressly incorporated into the disclosure of the present application.

The following examples further illustrate the present invention without limiting the scope of protection. In particular, the features, properties and advantages of the compounds and reaction conditions underlying the examples in question are also applicable to other substances and compounds not mentioned in detail but covered by the scope of protection, unless otherwise stated elsewhere. Incidentally, the invention is embodied in the entire claimed area and is not limited to the examples mentioned here.

Examples

General Synthetic Methods

• (1) Addition von SF₅OCl ( C. J. Schack, R. D. Wilson, J. S. Muirhead, S. N. Cohz, J. Am. Chem. Soc. 1969, 91, 2907–2911 ) an Olefine. Auf diesem Weg ist z. B. der vielseitige Synthesebaustein F₅SOCH₂CH₂Cl erhältlich ( L. R. Anderson, D. E. Young, D. E. Gould, R. Juurik-Hogan, D. Neuchterlein, W. B. Fox, J. Org. Chem. 1970, 35, 3730–3733 ).
• (2) Nukleophile Substitution von z. B. Triflaten mit TAS⁺ F₅SO^– ( W. Heilemann, R. Mews, S. Pohl, W. Saak, Chem. Ber. 1989, 122, 427–432 ). Die Substitutionsreaktion selbst ist nicht beschrieben, aber es ist zu erwarten, daß die Reaktivität des F₅SO-Anions vergleichbar mit der von CF₃O^– ist ( G. L. Trainor, J. Carbohydr. Chem. 1985, 4, 545–563 ).

The aliphatic OSF ₅ group is in principle accessible by two methods.

• (1) addition of SF ₅ OCl ( CJ Schack, RD Wilson, JS Muirhead, SN Cohz, J. Am. Chem. Soc. 1969, 91, 2907-2911 ) of olefins. On this way is z. B. the versatile synthesis building block F ₅ SOCH ₂ CH ₂ Cl available ( LR Anderson, DE Young, DE Gould, R. Juurik-Hogan, D. Neuchterlein, WB Fox, J. Org. Chem. 1970, 35, 3730-3733 ).
• (2) nucleophilic substitution of e.g. B. Triflates with TAS ⁺ F ₅ SO ^- ( W. Heilemann, R. Mews, S. Pohl, W. Saak, Chem. Ber. 1989, 122, 427-432 ). The substitution reaction itself is not described, but it is expected that the reactivity of the F ₅ SO anion is comparable to that of CF ₃ O ^- ( GL Trainor, J. Carbohydr. Chem. 1985, 4, 545-563 ).

Aromatic OSF ₅ compounds are accessible by reaction of the corresponding aromatic with F ₅ SOOSF ₅ ( JR Case, R. Price, NH Ray, HL Roberts, J. Wright, J. Chem. Soc. 1962, 2107-2110 ; JR Case, HL Roberts, UK 928412, 1963 ). The OSF ₅ group is very robust and the aromatic can be further derivatized analogously to the corresponding OCF ₃ compounds.

A) Synthesebeispiele

16: Zu einer Mischung von 80 mmol 15, 200 mmol getrocknetem K₂CO₃ und 300 ml CH₂C1₂ werden bei 0°C 100 mmol Trifluormethansulfonsäureanhydrid getropft. Man rührt 4 h nach, arbeitet wie üblich wäßrig auf und chromatographiert über Kieselgel (Pentan). Ausbeute 63% 16.

17: Eine Mischung von 20 mmol 16 und 25 mmol TAS⁺OSF₅ ^– (TAS⁺ = Tris(dimethylamino)sulfonium) in 100 ml Acetonitril wird 1 h bei –20°C gerührt. Dann läßt man auf Raumtemperatur kommen, rührt weitere 18 h, arbeitet wäßrig auf und chromatographiert über Kieselgel (Pentan). Ausbeute 54% 17.

18: 20 mmol 17 in 400 ml THF werden in Gegenwart von 2 g 5% Pd-C bei RT und Normaldruck bis zum Ende der Wasserstoffaufnahme hydriert. Man filtriert über Celite vom Katalysator ab, und reinigt das Produkt durch fraktionierte Destillation. Ausbeute 92% 18, farbloses Öl.

19: Eine Lösung von 100 mmol 18 in 200 ml Toluol wird unter Eiskühlung mit 120 mmol PBr₃ versetzt und für 3 h zum Rückfluß erhitzt. Man läßt abkühlen und arbeitet wie üblich wäßrig auf. Das Rohprodukt wird destillativ gereinigt. Ausbeute: 62% 19, farbloses Öl.

20: Eine Mischung von 10 mmol 19 und 30 ml Pyridin wird für 2 h zum Sieden erhitzt. Man engt im Vakuum ein und fällt den Rückstand mit Diethylether aus. Ausbeute: 89% 20, blaßrosa Feststoff.

21: Eine Lösung von 100 mmol 18, 100 mmol Acrylsäure, 105 mmol DCC (N,N'-Dicyclohexylcarbodiimid) und 5 mmol DMAP (4-(N,N-Dimethylamino)pyridin) in 300 ml THF wird 18 h bei RT gerührt. Man gießt in Wasser und arbeitet wie üblich wäßrig auf. Das Rohprodukt wird durch Chromatographie (Kieselgel; Pentan) gereinigt. Ausbeute: 87% 21, farbloses Öl.

22: Eine Mischung von 100 mmol 19 und 150 mmol Dicyclohexylamin wird für 18 h auf 180°C erhitzt. Das Produkt wird abdestilliert, gegen Ende bei verringertem Druck und erhöhter Temperatur. Das Rohprodukt wird durch fraktionierte Desillation gereinigt. Ausbeute: 68% 22, farbloses Öl.

23: Eine Lösung von 10 mmol 22 und 20 mmol Triethoxysilan in 80 ml CH₂Cl₂ wird mit 16 mg H₂PtCl₆·6H₂O in 1 ml iso-Propanol versetzt und 4 d bei RT gerührt. Nach beendeter Umsetzung wird das Produkt destillativ gereinigt. Ausbeute: 73% 23, farbloses Öl.

28: In einer Vakuumapparatur wird zu einer Lösung von 3.0 g (22 mmol) 24 in 10 ml trockenem CH₃CN 2,7 g (22 mmol) OSF₄ (25) einkondensiert. Die Suspension läßt man 1 h bei –30°C rühren, danach wird die Mischung langsam auf die Raumtemperatur erwärmt. Zu dem so (22 mmol) pregenerierten Salz 26 (Q⁺-OSF₅ ^–) wurden bei –10°C 6.3 g (22 mmol) 27 langsam zugegeben. Danach wird für 1 h bei 0°C und dann 12 h bei Raumtemperatur gerührt. Das Gemisch wird mit Et₂O extrahiert und die organische Phase mit Wasser gewaschen. Die organische Phase wird über Na₂SO₄ getrocknet, das Lösungsmittel abgezogen und im Hochvakuum getrocknet. Der Rückstand wird durch Silicagel filtriert (Laufmittel: Hexan/CHCl₃). Das Eluat wird eingeengt. Man erhält ein farbloses Öl. Ausbeute 4,2 g (68%) 28. Sdp. 225°C.
¹⁹F-NMR δ (CDCl₃) = AB₄X System: 77,57 (F^A, 1F, m mit übergeordnetem q), 59,37 (F⁸, 4F, m mit übergeordnetem d).
¹H-NMR δ (CDCl₃) = 5,81 (m, 1H, CH), 4,97 (m, 2H, CH₂), 4,36 (t, 2H, CH₂), 2,04 (m, 2H, CH₂), 1,70 (m, 2H, CH₂), 1,33 (m, 12H, CH₂).
HRMS: gef. 282,10768 ber. 282,10885 C₁₀H₁₉F₅OS 29: Darstellung von Thioessigsäure-S-(10-(pentafluorosulfanyloxy)decyl)ester

The compounds according to the invention can be prepared analogously to the corresponding CF ₃ or OCF ₃ derivatives by methods known to the person skilled in the art. General synthesis scheme

A) Synthesis examples

16: To a mixture of 80 mmol 15, 200 mmol of dried K ₂ CO ₃ and 300 ml of CH ₂ C1 ₂ are added dropwise at 0 ° C 100 mmol trifluoromethanesulfonic anhydride. The mixture is stirred for 4 h, worked up in the usual aqueous and chromatographed on silica gel (pentane). Yield 63% 16.

17: A mixture of 20 mmol 16 and 25 mmol TAS ⁺ OSF ₅ ^- (TAS ⁺ = tris (dimethylamino) sulfonium) in 100 ml acetonitrile is stirred for 1 h at -20 ° C. Then allowed to come to room temperature, stirred for a further 18 h, worked up in water and chromatographed on silica gel (pentane). Yield 54% 17.

18:20 mmol 17 in 400 ml of THF are hydrogenated in the presence of 2 g of 5% Pd-C at RT and normal pressure until the end of the hydrogen uptake. The mixture is filtered through Celite from the catalyst, and the product is purified by fractional distillation. Yield 92% 18, colorless oil.

19: A solution of 100 mmol of 18 in 200 ml of toluene is added under ice-cooling with 120 mmol of PBr ₃ and heated to reflux for 3 h. Allow to cool and works as usual on water. The crude product is purified by distillation. Yield: 62% 19, colorless oil.

20: A mixture of 10 mmol of 19 and 30 ml of pyridine is heated to boiling for 2 h. It is concentrated in vacuo and the residue is precipitated with diethyl ether. Yield: 89% 20, pale pink solid.

21: A solution of 100 mmol of 18, 100 mmol of acrylic acid, 105 mmol of DCC (N, N'-dicyclohexylcarbodiimide) and 5 mmol of DMAP (4- (N, N-dimethylamino) pyridine) in 300 ml of THF is stirred at RT for 18 h , It is poured into water and worked up as usual on water. The crude product is purified by chromatography (silica gel, pentane). Yield: 87% 21, colorless oil.

22: A mixture of 100 mmol 19 and 150 mmol dicyclohexylamine is heated to 180 ° C for 18 h. The product is distilled off, towards the end at reduced pressure and elevated temperature. The crude product is purified by fractional distillation. Yield: 68% 22, colorless oil.

23: A solution of 10 mmol of 22 and 20 mmol of triethoxysilane in 80 ml of CH ₂ Cl ₂ is admixed with 16 mg of H ₂ PtCl ₆ .6H ₂ O in 1 ml of isopropanol and stirred for 4 d at RT. After completion of the reaction, the product is purified by distillation. Yield: 73% 23, colorless oil.

28: In a vacuum apparatus, 2.7 g (22 mmol) of OSF ₄ (25) are condensed into a solution of 3.0 g (22 mmol) of 24 in 10 ml of dry CH ₃ CN. The suspension is allowed to stir for 1 h at -30 ° C, then the mixture is slowly warmed to room temperature. To the thus (22 mmol) pregenerated salt 26 (Q ⁺ -OSF ₅ ^- ) 6.3 g (22 mmol) of 27 were slowly added at -10 ° C. The mixture is then stirred for 1 h at 0 ° C and then for 12 h at room temperature. The mixture is extracted with Et ₂ O and the organic phase washed with water. The organic phase is dried over Na ₂ SO ₄ , the solvent is stripped off and dried under high vacuum. The residue is filtered through silica gel (eluent: hexane / CHCl ₃ ). The eluate is concentrated. A colorless oil is obtained. Yield 4.2 g (68%) 28. Bp 225 ° C.
¹⁹ F-NMR δ (CDCl ₃ ) = AB ₄ X system: 77.57 (F ^A , 1 F, m with superordinate q), 59, 37 (F ⁸ , ₄ F, m with superordinate d).
¹ H-NMR δ _(CDCl3) = 5.81 (m, 1H, CH), 4.97 (m, 2H, CH _2), 4.36 (t, 2H, CH _2), 2.04 (m , 2H, CH ₂ ), 1.70 (m, 2H, CH ₂ ), 1.33 (m, 12H, CH ₂ ).
HRMS: gef. 282,10768 ber. 282,10885 C ₁₀ H ₁₉ F ₅ OS 29: Preparation of thioacetic acid S- (10- (pentafluorosulfanyloxy) decyl) ester

5 ml of dried hexane are added under nitrogen to a heated, nitrogen-filled Schlenk tube, and 1.04 g (3.54 mmol) of the OSF ₅ alkene, 0.514 g (6.75 mmol) of freshly distilled thioacetic acid stored under N ₂ and a spatula tip of AlBN are added. Subsequently, the contents of the Schlenk vessel is degassed and heated under N ₂ in the closed state overnight at 60 ° C. Thereafter, the excess of thioacetic acid and the solvent hexane is removed in vacuo. Kugelrohr distillation of the residue gives a colorless product.

Substance: C ₁₂ H ₂₃ F ₅ O ₂ S ₂ ; M = 358.43 g / mol

analytics:
¹ H-NMR (500 MHz, CDCl ₃ )
4.32 (t); 2.84 (t); 2.30 (s); 1.80-1.20 (m) ppm.

¹³ C-NMR (126 MHz; _CDCl3)
195.89; 74.16; 30.53; 29.47; 29.25; 29.08; 28.99; 28.91; 28.80; 28.72; 25.29 ppm.

¹⁹ F-NMR (470 MHz; _CDCl3)
-28.8 (quint); -47.2 (d) ppm. Figure 30: Preparation of 10- (pentafluorosulfanyloxy) decylsulfonic acid, sodium salt

In a 25 ml round bottom flask with reflux condenser 3.0 g (8.4 mmol) of thioacetic acid S- (10- (pentafluorosulfanyloxy) decyl) ester and 7 ml of glacial acetic acid are presented. The mixture was heated to 60 ° C. by means of an oil bath, and a mixture of 1.42 g (38.1 mmol) of 92% H ₂ O ₂ (1.02 ml) and 5 ml of glacial acetic acid was slowly added dropwise by means of a dropping funnel. After a reaction time of 45 minutes, about 3 g (35.7 mmol) of NaHCO _{3 were added} to bind the resulting strong acid, and the volatile components were removed in vacuo. 3 g of the residue was dissolved in 37 ml of methanol and the undissolved residue was filtered off. The resulting solution was mixed with 60 ml of diethyl ether, the crystalline precipitate was filtered off with suction and dried in an evacuated desiccator. The filtrate was concentrated by rotary evaporation, the residue was taken up in 10 ml of methanol and precipitated again with 60 ml of ether, so that a second fraction of the product could be recovered.

Substance: C ₁₀ H ₂₀ F ₅ NaO ₄ S ₂ ; M = 386.38 g / mol

analytics:
¹ H-NMR (500 MHz, CD ₃ OD)
4.43 (t); 2.82-2.75 (m); 1.83-1.65 (m); 1.48-1.30 (m) ppm.

¹³ C-NMR (126 MHz, CD ₃ OD)
76.20; 52.76; 30.53; 30.47; 30.42; 30.14; 30.00; 29.87; 26.52; 26.05 ppm.

¹⁹ F NMR (470 MHz, CD ₃ OD)
-29.7 (quint); -48.3 (d) ppm.

MS (API) m / z: 363 [M-Na]; 212; 143rd

B) Determination of the static surface tension

For the test substance 30, the surface tensions γ of aqueous solutions with different concentrations were determined. device Tensiometer from Sinterface (model PAT1) Temperature of the measuring solutions room temperature measurement method Measurement of the surface tension on the hanging drop against air

The following values were found: c [%] γ [mN / m] 0.009 58.5 0.09 47.4 0.9 35.4

The test substance 30 is clearly surface-active.

C) degradation properties

As a preliminary / preliminary test, the determination of the inherent biodegradability of the test substance 30 according to the Zahn-Wellens / EMPA test ( OECD Guidelines for Testing of Chemicals, Method 302B, pages 1-8, adopted 17 July 1992 ) with unadapted activated sludge ["sludge (inoculum)"] from a wastewater treatment plant.

A mixture containing the test substance, mineral nutrients and a relatively large amount of activated sewage sludge (1 g / L dry matter) in an aqueous medium was shaken and aerated at 20-25 ° C in diffused light for up to 28 days.

The process of biodegradability was monitored by DOC determination in filtered samples taken daily or at other intervals. The ratio of deleted DOC (blank controls corrected) to initial DOC after each time interval was expressed as percent biodegradability at the time of sampling. Specific analysis of inorganic parameters such as fluoride ion and sulfate by ion chromatography was also performed.

Results:

The Zahn-Wellens test showed that test compound 30 was 76% biodegradable after 28 days - based on a Dissolved Organic Carbon (DOC) decrease. In addition, the formation of a considerable amount of inorganic fluoride and sulfate at the end of the test period was observed. The results are an indication of the partial mineralization of the SF ₅ O and SO _{S groups} during the test phase (see 1 to 3 ). Duration (d) Degradation (%) mg / fluoride mg / l sulphate 0 0 0.0 0.0 0.13 0 0.5 0.0 1 1 4.0 3.0 2 2 8.9 4.0 3 -4 14.0 13.0 6 19 26.5 40.0 7 20 27.9 47.0 8th 21 30.2 58.0 9 24 34.1 58.0 10 28 41.7 63.0 13 50 37.9 74.0 14 52 39.8 77.0 16 58 43.1 86.0 22 70 54.2 104.0 27 75 62.0 114.0 28 76 62.8 114.0 31 75 61.8 119.0 34 78 66.5 120.0 Duration (d) Fluoride (%) Sulfate (%) 0 0 0 0.13 0 0 1 3 1 2 8th 2 3 12 6 6 23 17 7 24 20 8th 26 25 9 29 25 10 36 27 13 33 31 14 34 33 16 37 36 22 47 44 27 53 48.3 28 54 48.3 31 53 50.4 34 57 50.8

QUOTES INCLUDE IN THE DESCRIPTION

This list of the documents listed by the applicant has been generated automatically and is included solely for the better information of the reader. The list is not part of the German patent or utility model application. The DPMA assumes no liability for any errors or omissions.

Cited patent literature

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Claims (12)

Compounds according to Formal (I) Z- (Ar) _n1 - (O) _n2 - (CH _{2) n3} -OSF ₅ (I) wherein: Z is ausgewält from the group consisting of: (i) anionic substituents: -COO ^- M ^+, -SO ₃ ^- M ^+, -OSO ₃ ^- M ^+, -PO ₃ ^2- M ⁺ _2, -OPO ₃ ^{2 -} M ⁺ ₂ , -NHSO ₃ ^- M ⁺ , - (OCH ₂ CH ₂ ) _q O ^- M ⁺ , - (OCH ₂ CH ₂ ) _qq O (CH ₂ ) _r COO ^- M ⁺ , - (OCH ₂ CH ₂ ) _s O (CH ₂ ) _t SO ₃ ^- M ⁺ , - (OCH ₂ CH ₂ ) _u O (CH ₂ ) _u OSO ₃ ^- M ⁺ , - (OCH ₂ CH ₂ ) _w O (CH ₂ ) _x PO ₃ ^2- M ⁺ ₂ or - (OCH ₂ CH ₂ ) _y O (CH ₂ ) ₃ OPO ₃ ^2- M ⁺ ₂ , wherein: M ⁺ independently is H ⁺ , a metal cation, preferably an alkali metal cation or alkaline earth metal cation, more preferably Li ⁺ , Na ⁺ , K ⁺ , NH ₄ ⁺ , Ca ²⁺ or Zn ²⁺ , q, qq, s, u, w, y independently of one another denote 1-1000, r, t, v, x, a independently of one another , 2 or 3, (ii) cationic substituents: -N (R ¹ R ² R ³ ) ⁺ X ^- , -P (R ⁴ R ⁵ R ⁵ ) ⁺ X ^- ,

wherein: R _{a is} independently H or -CH ₃ , X ^- independently of one another are Cl ^- , Br ^- , I ^- , CH ₃ SO ₃ ^- , CF ₃ SO ₃ ^- , methylphenyl-SO ₃ ^- or phenyl-SO ₃ ^- R ¹ , R ² , R ³ , R ⁴ , R ⁴ , R ⁶ independently of one another are H, alkyl, aryl or benzyl, (iii) neutral substituents: alkyl, -OH, -O (O) C-alkyl, (OCH ₂ CH ₂ ) _b OH, -O- (glycoside) _c (eg glucoside, diglucoside, triglucoside etc.), -OCH ₂ CHOHCH ₂ OH or - (OCH ₂ CH ₂ ) _d OCH ₂ CHOHCH ₂ OH wherein: b, d are independently 1-1000, c, e, f are independently 1-10, (iv) reactive substituents: - (OCH ₂ CH ₂ ) _g (OCH ₂ -phenyl) _h NCO, -SiR ⁷ R ⁸ W, -SiR ⁹ W ₂ , -SiW ₃ , COW, - (OCH ₂ CH ₂ ) _i SO ₂ CH = CH ₂ or

wherein: R ⁷ , R ⁸ , R ^{9 are} independently alkyl, aryl or benzyl, preferably CH ₃ , W is independently H, Cl, F, NR ^d ₂ , OR ^d or N-imidazolyl, R _b independently of one another Cl or F, R ^d independently of one another are optionally substituted alkyl, where in the case of NR ^d ₂ both radicals R ^d together with the nitrogen atom to which they are attached can also form heterocyclyl, g, i, j independently of one another denote 0-1000 , h is 0 or 1, (v) polymerizable substituents: - (OCH ₂ CH ₂ ) _k OCOCR = CH ₂ , - (OCH ₂ CH ₂ ) _kk OCH = CH ₂ ,

in which: R independently of one another is H or CH ₃ , k, kk, I, II independently of one another denote 0-1000, Ar is an aromatic mono- or bicyclic carbon ring having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 C atoms, n1, n2 independently of one another 0 or 1, preferably 0, n3 is 0-1000, preferably 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, particularly preferably 2, 3, 4, 5 or 6. Compounds according to claim 1, wherein n1 and n2 represent 0. Compounds according to one or more of claims 1 to 2, wherein Z is a substituent selected from the group consisting of alkyl, -SO ₃ ^- M ^+, -O (CH ₂ OH ₂ O) _a1 H, -OH, -SiW _3, - O (O) C-alkyl,

in which preferably a1 is 1-20, W is OR ^d and R ^{d is} alkyl. Compounds according to one or more of claims 1 and 3, wherein Ar represents phenyl or naphthyl. Compounds according to one or more of claims 1 to 4, wherein Z is a substituent selected from the group consisting of alkyl, -SO ₃ ^- M ^+, -O (CH ₂ CH ₂ O) _a1 H, -OH, -SiW _3, - O (O) C-alkyl,

wherein preferably a1 is 1-20, W is OR ^d and R ^{d is} alkyl, and Ar is phenyl or naphthyl. Compounds according to one or more of claims 1 to 5 selected from the group consisting of:

(EtO) ₃ Si (CH ₂ ) ₅ OSF ₅ , F ₅ SO (CH _{2) 4} -COOH; F ₅ SO- (CH ₂ ) ₄ -SO ₃ H; F ₅ SO- (CH ₂ ) ₄ -O-SO ₃ H F ₅ SO (CH _{2) 5} -COOH; F ₅ SO- (CH ₂ ) ₅ -SO ₃ H; F ₅ SO- (CH ₂ ) ₅ -O-SO ₃ H F ₅ SO (CH _{2) 6} -COOH; F ₅ SO- (CH ₂ ) ₆ -SO ₃ H; F ₅ SO- (CH ₂ ) ₆ -O-SO ₃ H F ₅ SO (CH _{2) 7} -COOH; F ₅ SO- (CH ₂ ) ₇ -SO ₃ H; F ₅ SO- (CH ₂ ) ₇ -O-SO ₃ H F ₅ SO (CH _{2) 8} -COOH; F ₅ SO- (CH ₂ ) ₈ -SO ₃ H; F ₅ SO- (OH ₂ ) ₈ -O-SO ₃ H F ₅ SO (CH _{2) 9} -COOH; F ₅ SO- (CH ₂ ) ₉ -SO ₃ H; F ₅ SO- (CH ₂ ) ₉ -O-SO ₃ H F ₅ SO (CH _{2) 10} -COOH; F ₅ SO- (CH ₂ ) ₁₀ -SO ₃ H; F ₅ SO- (CH ₂ ) ₁₀ -O-SO ₃ H F ₅ SO (CH _{2) 11} -COOH; F ₅ SO- (CH ₂ ) ₁₁ -SO ₃ H; F ₅ SO- (CH ₂ ) ₁₁ -O-SO ₃ H F ₅ SO (CH _{2) 12} -COOH; F ₅ SO- (CH ₂ ) ₁₂ -SO ₃ H; F ₅ SO- (CH ₂ ) ₁₂ -O-SO ₃ H F ₅ SO (CH _{2) 13} -COOH; F ₅ SO- (CH ₂ ) ₁₃ -SO ₃ H; F ₅ SO- (CH ₂ ) ₁₃ -O-SO ₃ H F ₅ SO (CH _{2) 14} -COOH; F ₅ SO- (CH ₂ ) ₁₄ -SO ₃ H; F ₅ SO- (CH ₂ ) ₁₄ -O-SO ₃ H F ₅ SO (CH _{2) 15} -COOH; F ₅ SO- (CH ₂ ) ₁₅ -SO ₃ H; F ₅ SO- (CH ₂ ) ₁₅ -O-SO ₃ H F ₅ SO (CH _{2) 16} -COOH; F ₅ SO- (CH ₂ ) ₁₆ -SO ₃ H; F ₅ SO- (CH ₂ ) ₁₆ -O-SO ₃ H F ₅ SO (CH _{2) 17} -COOH; F ₅ SO- (CH ₂ ) ₁₇ -SO ₃ H; F ₅ SO- (CH ₂ ) ₁₇ -O-SO ₃ H F ₅ SO (CH _{2) 18} -COOH; F ₅ SO- (CH ₂ ) ₁₈ -SO ₃ H; F ₅ SO- (CH ₂ ) ₁₈ -O-SO ₃ H F ₅ SO (CH _{2) 19} -COOH; F ₅ SO- (CH ₂ ) ₁₉ -SO ₃ H; F ₅ SO- (CH ₂ ) ₁₉ -O-SO ₃ H F ₅ SO (CH _{2) 20} -COOH; F ₅ SO- (CH ₂ ) ₂₀ -SO ₃ H; F ₅ SO- (CH ₂ ) ₂₀ -O-SO ₃ H F ₅ SO (CH _{2) 21} -COOH; F ₅ SO- (CH ₂ ) ₂₁ -SO ₃ H; F ₅ SO- (CH ₂ ) ₂₁ -O-SO ₃ H F ₅ SO (CH _{2) 22} -COOH; F ₅ SO- (CH ₂ ) ₂₂ -SO ₃ H; F ₅ SO- (CH ₂ ) ₂₂ -O-SO ₃ H F ₅ SO (CH _{2) 23} -COOH; F ₅ SO- (CH ₂ ) ₂₃ -SO ₃ H; F ₅ SO- (CH ₂ ) ₂₃ -O-SO ₃ H F ₅ SO (CH _{2) 24} -COOH; F ₅ SO- (CH ₂ ) ₂₄ -SO ₃ H; F ₅ SO- (CH ₂ ) ₂₄ -O-SO ₃ H F ₅ SO- (CH ₂ ) ₄ -COONa; F ₅ SO- (CH ₂ ) ₄ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₄ -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₅ -COONa; F ₅ SO- (CH ₂ ) ₅ -SO ₃ Na; F ₅ SO- (OH ₂ ) ₅ -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₆ -COONa; F ₅ SO- (CH ₂ ) ₆ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₆ -O-SO ₃ Na F ₅ SO (CH _{2) 7} -COONa; F ₅ SO- (CH ₂ ) ₇ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₇ -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₈ -COONa; F ₅ SO- (CH ₂ ) ₈ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₈ -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₉ -COONa; F ₅ SO- (CH ₂ ) ₉ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₉ -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₁₀ -COONa; F ₅ SO- (CH ₂ ) ₁₀ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₁₀ -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₁₁ -COONa; F ₅ SO- (CH ₂ ) ₁₁ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₁₁ -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₁₂ -COONa; F ₅ SO- (CH ₂ ) ₁₂ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₁₂ -O-SO ₃ Na F ₅ SO (CH _{2) 13} COONa; F ₅ SO- (CH ₂ ) ₁₃ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₁₃ -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₁₄ -COONa; F ₅ SO- (CH ₂ ) ₁₄ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₁₄ -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₁₅ -COONa; F ₅ SO- (CH ₂ ) ₁₅ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₁₅ -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₁₆ -COONa; F ₅ SO- (CH ₂ ) ₁₆ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₁₆ -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₁₇ -COONa; F ₅ SO- (CH ₂ ) ₁₇ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₁₇ -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₁₈ -COONa; F ₅ SO- (CH ₂ ) ₁₈ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₁₈ -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₁₉ -COONa; F ₅ SO- (CH ₂ ) ₁₉ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₁₉ -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₂₀ -COONa; F ₅ SO- (CH ₂ ) ₂₀ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₂₀ -O-SO ₃ Na F ₅ SO (CH _{2) 21} COONa; F ₅ SO- (CH ₂ ) ₂₁ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₂₁ -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₂₂ -COONa; F ₅ SO- (CH ₂ ) ₂₂ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₂₂ -O-SO ₃ Na F ₅ SO (CH _{2) 23} COONa; F ₅ SO- (CH ₂ ) ₂₃ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₂₃ -O-SO ₃ Na F ₅ SO (CH _{2) 24} COONa; F ₅ SO- (CH ₂ ) ₂₄ -SO ₃ Na; F ₅ SO- (CH ₂ ) ₂₄ -O-SO ₃ Na F ₅ SO (phenyl) -COOH; F ₅ SO- (phenyl) -SO ₃ H; F ₅ SO- (phenyl) -O-SO ₃ H F ₅ SO-CH ₂ - (phenyl) -COOH; F ₅ SO-CH ₂ - (phenyl) -SO ₃ H; F ₅ SO-CH ₂ - (phenyl) -O-SO ₃ H F ₅ SO-CH ₂ -O- (phenyl) -COOH; F ₅ SO-CH ₂ -O- (phenyl) -SO ₃ H; F ₅ SO-CH ₂ -O- (phenyl) -O-SO ₃ H F ₅ SO- (CH ₂ ) ₂ -O- (phenyl) -COOH; F ₅ SO- (CH ₂ ) ₂ -O- (phenyl) -SO ₃ H; F ₅ SO- (CH ₂ ) ₂ -O- (phenyl) -O-SO ₃ H F ₅ SO- (CH ₂ ) ₃ -O- (phenyl) -COOH; F ₅ SO- (CH ₂ ) ₃ -O- (phenyl) -SO ₃ H; F ₅ SO- (CH ₂ ) ₃ -O- (phenyl) -O-SO ₃ H F ₅ SO- (CH ₂ ) ₄ -O- (phenyl) -COOH; F ₅ SO- (CH ₂ ) ₄ -O- (phenyl) -SO ₃ H; F ₅ SO- (CH ₂ ) ₄ -O- (phenyl) -O-SO ₃ H F ₅ SO- (CH ₂ ) ₅ -O- (phenyl) -COOH; F ₅ SO- (CH ₂ ) ₅ -O- (phenyl) -SO ₃ H; F ₅ SO- (CH ₂ ) ₅ -O- (phenyl) -O-SO ₃ H F ₅ SO- (CH ₂ ) ₆ -O- (phenyl) -COOH; F ₅ SO- (CH ₂ ) ₆ -O- (phenyl) -SO ₃ H; F ₅ SO- (CH ₂ ) ₆ -O- (phenyl) -O-SO ₃ H F ₅ SO- (CH ₂ ) ₇ -O- (phenyl) -COOH; F ₅ SO- (CH ₂ ) ₇ -O- (phenyl) -SO ₃ H; F ₅ SO- (CH ₂ ) ₇ -O- (phenyl) -O-SO ₃ H F ₅ SO- (CH ₂ ) ₈ -O- (phenyl) -COOH; F ₅ SO- (CH ₂ ) ₈ -O- (phenyl) -SO ₃ H; F ₅ SO- (CH ₂ ) ₈ -O- (phenyl) -O-SO ₃ H F ₅ SO (CH _{2) 9} -O- (phenyl) -COOH; F ₅ SO- (CH ₂ ) ₉ -O- (phenyl) -SO ₃ H; F ₅ SO- (CH ₂ ) ₉ -O- (phenyl) -O-SO ₃ H F ₅ SO- (CH ₂ ) ₁₀ -O- (phenyl) -COOH; F ₅ SO- (CH ₂ ) ₁₀ -O- (phenyl) -SO ₃ H; F ₅ SO- (CH ₂ ) ₁₀ -O- (phenyl) -O-SO ₃ H F ₅ SO (phenyl) -COONa; F ₅ SO- (phenyl) -SO ₃ Na; F ₅ SO- (phenyl) -O-SO ₃ Na F ₅ SO-CH ₂ - (phenyl) -COONa; F ₅ SO-CH ₂ - (phenyl) -SO ₃ Na; F ₅ SO-CH ₂ - (phenyl) -O-SO ₃ Na F ₅ SO-CH ₂ -O- (phenyl) -COONa; F ₅ SO-CH ₂ -O- (phenyl) -SO ₃ Na; F ₅ SO-CH ₂ -O- (phenyl) -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₂ -O- (phenyl) -COONa; F ₅ SO- (CH ₂ ) ₂ -O- (phenyl) -SO ₃ Na; F ₅ SO- (CH ₂ ) ₂ -O- (phenyl) -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₃ -O- (phenyl) -COONa; F ₅ SO- (CH ₂ ) ₃ -O- (phenyl) -SO ₃ Na; F ₅ SO- (CH ₂ ) ₃ -O- (phenyl) -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₄ -O- (phenyl) -COONa; F ₅ SO- (CH ₂ ) ₄ -O- (phenyl) -SO ₃ Na; F ₅ SO- (CH ₂ ) ₄ -O- (phenyl) -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₅ -O- (phenyl) -COONa; F ₅ SO- (CH ₂ ) ₅ -O- (phenyl) -SO ₃ Na; F ₅ SO- (CH ₂ ) ₅ -O- (phenyl) -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₆ -O- (phenyl) -COONa; F ₅ SO- (CH ₂ ) ₆ -O- (phenyl) -SO ₃ Na; F ₅ SO- (CH ₂ ) ₆ -O- (phenyl) -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₇ -O- (phenyl) -COONa; F ₅ SO- (CH ₂ ) ₇ -O- (phenyl) -SO ₃ Na; F ₅ SO- (CH ₂ ) ₇ -O- (phenyl) -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₈ -O- (phenyl) -COONa; F ₅ SO- (CH ₂ ) ₈ -O- (phenyl) -SO ₃ Na; F ₅ SO- (CH ₂ ) ₈ -O- (phenyl) -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₉ -O- (phenyl) -COONa; F ₅ SO- (CH ₂ ) ₉ -O- (phenyl) -SO ₃ Na; F ₅ SO- (CH ₂ ) ₉ -O- (phenyl) -O-SO ₃ Na F ₅ SO- (CH ₂ ) ₁₀ -O- (phenyl) -COONa; F ₅ SO- (CH ₂ ) ₁₀ -O- (phenyl) -SO ₃ Na; F ₅ SO- (CH ₂ ) ₁₀ -O- (phenyl) -O-SO ₃ Na F ₅ SO (CH _{2) 4} -OH; F ₅ SO- (CH ₂ ) ₄ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₄ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 5} -OH; F ₅ SO- (CH ₂ ) ₅ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₅ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 6} -one; F ₅ SO- (CH ₂ ) ₆ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₆ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 7} OH; F ₅ SO- (CH ₂ ) ₇ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₇ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 8} -OH; F ₅ SO- (CH ₂ ) ₈ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₈ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 9} -OH; F ₅ SO- (CH ₂ ) ₉ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₉ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 10} -OH; F ₅ SO- (CH ₂ ) ₁₀ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₁₀ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 11} -OH; F ₅ SO- (CH ₂ ) ₁₁ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₁₁ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 12} -OH; F ₅ SO- (CH ₂ ) ₁₂ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₁₂ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 13} -OH; F ₅ SO- (CH ₂ ) ₁₃ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₁₃ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 14} -OH; F ₅ SO- (CH ₂ ) ₁₄ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₁₄ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 15} -OH; F ₅ SO- (CH ₂ ) ₁₅ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₁₅ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 16} -OH; F ₅ SO- (CH ₂ ) ₁₆ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₁₆ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 17} -OH; F ₅ SO- (CH ₂ ) ₁₇ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₁₇ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 18} -OH; F ₅ SO- (CH ₂ ) ₁₈ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₁₈ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 19} -OH; F ₅ SO- (CH ₂ ) ₁₉ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₁₉ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 20} -OH; F ₅ SO- (CH ₂ ) ₂₀ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₂₀ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 21} -OH; F ₅ SO- (CH ₂ ) ₂₁ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₂₁ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 22} -OH; F ₅ SO- (CH ₂ ) ₂₂ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₂₂ - (OCH ₂ OH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 23} -OH; F ₅ SO- (CH ₂ ) ₂₃ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₂₃ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO (CH _{2) 24} -OH; F ₅ SO- (CH ₂ ) ₂₄ - (OCH ₂ CH ₂ ) _m -OH; F ₅ SO- (CH ₂ ) ₂₄ - (OCH ₂ CH ₂ ) _m -SO ₂ -CH = CH ₂ F ₅ SO- (CH ₂ ) ₄ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₄ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₄ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₅ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₅ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₅ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₆ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₅ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₆ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₇ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₇ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₇ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₈ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₈ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₈ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₉ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₉ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₉ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₁₀ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₀ - (OCH ₂ CH ₂ ) _m OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₀ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₁₁ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₁ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₁ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₁₂ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₂ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₂ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₁₃ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₃ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₃ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₁₄ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₄ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₄ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₁₅ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₅ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₅ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₁₆ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₆ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₆ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₁₇ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₇ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₇ (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₁₈ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₈ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₈ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₁₉ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₉ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₁₉ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₂₀ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₂₀ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₂₀ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₂₁ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₂₁ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₂₁ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₂₂ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₂₂ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₂₂ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₂₃ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₂₃ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₂₃ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₂₄ - (OCH ₂ CH ₂ ) _m -OCOCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₂₄ - (OCH ₂ CH ₂ ) _m -OCH = CH ₂ ; F ₅ SO- (CH ₂ ) ₂₄ - (OCH ₂ CH ₂ ) _m -OAr (NCO) _p F ₅ SO- (CH ₂ ) ₄ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₄ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₄ -O-glucoside F ₅ SO- (CH ₂ ) ₅ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₅ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₅ -O-glucoside F ₅ SO- (CH ₂ ) ₆ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₆ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₆ -O-glucoside F ₅ SO- (CH ₂ ) ₇ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₇ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₇ -O-glucoside F ₅ SO- (CH ₂ ) ₈ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₈ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₈ -O-glucoside F ₅ SO- (CH ₂ ) ₉ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₉ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₉ -O-glucoside F ₅ SO- (CH ₂ ) ₁₀ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₀ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₀ -O-glucoside F ₅ SO- (CH ₂ ) ₁₁ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₁ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₁ -O-glucoside F ₅ SO- (CH ₂ ) ₁₂ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₂ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₂ -O-glucoside F ₅ SO- (CH ₂ ) ₁₃ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₃ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₃ -O-glucoside F ₅ SO- (CH ₂ ) ₁₄ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₄ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₄ -O-glucoside F ₅ SO- (CH ₂ ) ₁₅ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₅ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₅ -O-glucoside F ₅ SO- (CH ₂ ) ₁₆ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₆ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₆ -O-glucoside F ₅ SO- (CH ₂ ) ₁₇ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₇ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₇ -O-glucoside F ₅ SO- (CH ₂ ) ₁₈ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₈ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₈ -O-glucoside F ₅ SO- (CH ₂ ) ₁₉ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₉ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₁₉ -O-glucoside F ₅ SO- (CH ₂ ) ₂₀ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₂₀ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₂₀ -O-glucoside F ₅ SO- (CH ₂ ) ₂₁ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₂₁ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₂₁ -O-glucoside F ₅ SO- (CH ₂ ) ₂₂ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₂₂ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₂₂ -O-glucoside F ₅ SO- (CH ₂ ) ₂₃ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₂₃ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₂₃ -O-glucoside F ₅ SO- (CH ₂ ) ₂₄ -N ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₂₄ -P ⁺ R ¹ R ² R ³ Z ^- ; F ₅ SO- (CH ₂ ) ₂₄ -O-glucoside Use of compounds according to one or more of claims 1 to 6 as surfactants, as water repellents or Oleophobiermittel, in particular in the surface modification of textiles, paper, glass, porous building materials or adsorbents, as an antistatic agent, in particular in the treatment of textiles, such as clothing, carpets and carpets, upholstery coverings in furniture and automobiles, non-woven textile materials, leather goods, papers and cardboard, wood and wood-based materials, mineral substrates such as stone, cement, concrete, plaster, ceramics, such as glazed and unglazed bricks, earthenware, porcelain, and Glasses, as well as for plastics and metallic substrates, as additives in surface coating compositions, such as printing inks, paints, paints, lacquers, photographic coatings, special coatings for semiconductor photolithography, such as photoresists, top anti-reflective coatings, bottom anti-reflective coatings, or in additive for the purpose of additization of corresponding preparations, as a foam stabilizer and / or to support film formation, in particular in fire-extinguishing foams, as an interface mediator or emulsifier, in particular for the production of fluoropolymers, or as an antimicrobial agent, in particular as a reagent for antimicrobial surface modification, Process for the preparation of compounds according to one or more of Claims 1 to 6, comprising the steps: (a) conversion of the substituent U of a compound of the formula (II) U- (Ar) _n1 - (O) _n2 - (CH _{2) n3} -OSF ₅ (II) where UF, Cl, Br, I or OH and Ar, n1, n2 and n3 have the abovementioned meaning, into a substituent Z of a compound of the formula (I) Z- (Ar) _n1 - (O) _n2 - (CH _{2) n3} -OSF ₅ (I) wherein Z, Ar, n1, n2 and n3 have the abovementioned meaning, z. By oxidation, esterification or S _N2 reaction, and optionally (b) converting a substituent Z as defined above into another substituent Z as defined above, e.g. By replacing a hydroxyl group with a -O (CH ₂ CH ₂ O) _n H group or introducing a sodium sulfate group. Composition containing at least one compound according to one or more of claims 1 to 6. Composition according to claim 9, characterized in that a carrier suitable for the respective intended use and optionally further specific active substances are contained. Agent according to claim 9 or 10, characterized in that the agent is paint and lacquer preparations, fire-extinguishing agents, lubricants, detergents and cleaners, de-icers or water repellents for textile finishing or glass treatment. Intermediate compounds according to formula (III) V (Ar) _n1 - (O) _n2 - (CH _{2) n3} -OSF ₅ (III) wherein: V is selected from the group consisting of H ₂ C = CH-, alkyl-HC = CH-, Cl, Br, I, OH, -OCH ₂ -phenyl, -BR ₂ , -SiR ₃ , -O ₃ SR where R is alkyl, aryl, F, CF ₃ , phenyl-CH ₃ , Ar is an aromatic mono- or bicyclic carbon ring of 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16 , 17 or 18 carbon atoms, n1, n2 independently of one another denote 0 or 1, preferably 0, n3 0-1000, preferably 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, particularly preferably 2, 3, 4, 5 or 6 means.

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