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United States Patent (19) 11) 4,425,278 Wirth Et Al

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United States Patent (19) 11) 4,425,278 Wirth Et Al United States Patent (19) 11) 4,425,278 Wirth et al. 45 Jan. 10, 1984 54) COMPLEX COMPOUNDS, PROCESS FOR 3,972,868 8/1976 Avela .......................... 260/439 RX THEIR PREPARATION, AND THEIR USE Primary Examiner-Helen M. S. Sneed (75) Inventors: Hermann O. Wirth, Bensheim; Attorney, Agent, or Firm-Luther A. R. Hall Hans-Helmut Friedrich, Lautertal, both of Fed. Rep. of Germany 57 ABSTRACT A complex compound of a metal salt or metalloid salt 73 Assignee: Ciba-Geigy Corporation, Ardsley, and an ansolvo-acid or proton-acid, of the general for N.Y. mula I 21 Appl. No.: 278,763 22) Filed: Jun. 29, 1981 . Related U.S. Application Data in which M is a m-valent cation of a metal or metalloid, a metal-oxy or metal-dioxy cation or a hydrogen atom, 62 Division of Ser. No. 938,172, Aug. 30, 1978, Pat. No. X is a n-valent anion of a n-basic inorganic proton-acid 4,336,148. or of a n-basic organic acid selected from the group of 51 Int. Cl......................... C07F 11/00; CO7F 15/04 the aliphatic and cycloaliphatic carboxylic acids with 52 U.S. C. ............................. 260/429 R; 260/429.5; up to 8 C atoms, which can be substituted by halogen 260/429.9; 260/438.1; 260/448 R; 556/482; and/or hydroxyl groups, the aromatic monocarboxylic, 568/6; 568/852 dicarboxylic and tricarboxylic acids, which may be (58) Field of Search ....... 260/429 R, 439 R, 448 AD, substituted by hydroxyl, halogen and/or nitro groups, 260/448 R, 429.5; 568/852; 556/482 the organic oxyacids of phosphorus and sulphur, the organic thioacids of phosphorus, and the mercaptans, (56) References Cited the inorganic or organic acid having a pKa value of at U.S. PATENT DOCUMENTS most 15.8 or, if M is a proton, of at most 11, Y is water 2,150,349 3/1939 van Peski et al. .......... 260/439 RX or a neutral organic molecule which can be bound 2,466,445 4/1949 Landau ... ... 260/439 R coodinatively by the cation or the anion, Z is a com 3,219,635 li/1965 Emrick ........................... 568/852 X plex-forming vicinal diol with at least 6 C atoms, p is 0 3,420,932 1/1969 Jones et al. 260/448 AD X or a value between 0 and 2, q is a value from 1 to 32, m 3,507,896 4/1970 Jones et al. .................. 260/448 AD 3,511,864 5/1970 Ugelow ....... ... 260/448 AD is an integer from 1 to 6 and, if M is a hydrogen atom, 3,629,229 12/1971 Schmank ..... ... 260/448 RX is 1 and n is an integer from 1 to 4, and mixtures of such 3,686,249 8/1972 Hartmann .................... 260/448 AD compounds. 3,901,931 8/1975 Rasberger et al. ............. 260/439 R 3,944,625 3/1976 Neal ............................ 260/439 RX 8 Claims, No Drawings 4,425,278 1. 2 scribed is their low heat stability, which results from the COMPLEX COMPOUNDS, PROCESS FOR THEIR low complexing capacity of the proposed alcohols. PREPARATION, AND THEIR USE German Offenlegungsschrift No. 2,330,906 describes nickel complexes of nickel salts of hydroxy-substituted This is a divisional of application Ser. No. 938,172, and alkyl-substituted phenylcarboxylic acids with alco filed on Aug. 30, 1978, now U.S. Pat. No. 4,336,148, hols or polyols, which complexes have good heat stabil issued on June 22, 1982. ity and are used as light stabilisers in polymers. This The present invention relates to complex compounds publication again does not tackle the problem of con of preferably inorganic salts and proton-acids or ansol verting salts, by means of one particular complexing voacids with vicinal diols, a process for their prepara 10 reagent, into products which are soluble in, for exam tion, and their use as antistatic additives in natural and ple, hydrocarbons. synthetic hydrocarbon-based polymers, lubricants and For completeness, it should be mentioned that the fuels, category of metal salts complexed with crown ethers It is known to react various inorganic salt-like com can also comprise compounds which are soluble in pounds with monofunctional or polyfunctional alco 15 non-polar, aprotic solvents. A disadvantage of these hols, the resulting compounds being described as alco complexes is that the crown ethers have a specific com hol complexes. plexing capacity for certain cations only, and that the For example, U.S. Pat. No. 3,420,932 describes reac synthesis of the crown ethers themselves is expensive tion products of basic aluminium salts with organic and uneconomical. polyhydroxy compounds; in addition to various diols, 20 It is an object of the present invention to provide a glycerol is mentioned. These products, obtained by complexed heat-stable compound of a metal salt or direct reaction of the basic aluminium salts with the metalloid salt, and of a proton-acid or ansolvo-acid, polyhydroxy compounds, have the disadvantage that which is soluble even in non-polar aprotic solvents and they are only soluble in polar protic solvents, for exam which is an effective antistatic additive in this solvent, ple alcohols, but not in non-polar aprotic solvents, for 25 in lubricants or in polymers. A further object of the example aliphatic or aromatic hydrocarbons. This be present invention is to provide a general process for the haviour may be explained, for example, by the fact that preparation of this complex compound. in the reaction described complex polymers are pro The present invention relates to complex compounds duced via the formation of an alcoholate, as is stated to of a metal salt of metalloid salt and an ansolvo-acid or be the case for a similar process in German Patent Spec proton-acid, which have the composition I ification No. 1,468,537, column 4, lines 10-21. The products described in the latter patent are also sparingly M".Xmp Y.qZ (I) soluble in alcohols but only dispersible in a polar or ganic solvent, for example a halogenated hydrocarbon. in which M is a m-valent cation of a metal or metalloid, Anal. Chemie 41 (II), 1456-58 (1969) discloses that 35 a metal-oxy or metal-dioxy cation or a hydrogen atom, barium hydroxide forms alcoholates with diglycerol X is a n-valent anion of a n-basic inorganic proton-acid and that residual free hydroxyl groups of the diglycerol or of a n-basic organic acid selected from the group of can form chelate bonds with the barium cation. As a the aliphatic and cycloaliphatic carboxylic acids with result of the strongly polar character of the ligand, these up to 8 C atoms, which can be substituted by halogen chelated alcohols are also virtually insoluble in hydro 40 and/or hydroxyl groups, the aromatic monocarboxylic, carbons. dicarboxylic and tricarboxylic acids, which may be Kim. Tekknol. Topal. Masel, 11, 25-28 (1974), de substituted by hydroxyl, halogen and/or nitro groups, scribes the reaction of molybdenum pentachloride with the organic oxyacids of phosphorus and sulphur, the C12-C14-1,2-diols, alcoholates being formed as the reac organic thioacids of phosphorus, and the mercaptans, tion products, with elimination of hydrogen halide. 45 the inorganic or organic acid having a pKa value of at Alcoholates from diols and molybdenum halides are most 15.8 or, if M is a proton, of at most 11, Y is water also described in German Patent Specification No. or a neutral organic molecule which can be bound coor 954,448. These alcoholates are soluble in mineral oils. A dinatively by the cation or the anion, Z is a complex disadvantage of these compounds is that active constitu forming vicinal diol with at least 6 C atoms, p is 0 or a ents of the compound, in the present case the halogen 50 value between 0 and 2, q is a value from 1 to 32, m is an atoms, are replaced as a result of the formation of the integer from 1 to 6 and, if M is a hydrogenatom, is 1 and alcoholate. n is an integer from 1 to 4, and mixtures of such com J. inorg. nucl. Chem., 34,357-59 (1972) discloses that pounds. lanthanum perchlorates in aqueous solution can form The composition I only comprises monomeric salts; complexes with polyols, for example glycerol. These 55 hence, in the part MnXn of the formula, the subscript complexes again are insoluble in non-polar aprotic sol indices n and m are always 1 if the superscript indices m Vents. and n are identical. However, in the monomeric salts X Reaction products of, for example, lead oxide, fatty can be a polymeric anion. acids or higher carboxylic acids and alkoxy-alcohols, The m-valent cation is preferably derived from a for example 2-ethoxyethanol, or polyols, for example metal of group la to 8a and 1b to 5b of the periodic table sorbitol, are described, in French Patent Specification of the elements, the lanthanides, uranium, plutonium or No. 2,264,082, as oil-soluble metal complexes. The solu the metalloids boron, silicon, germanium and antimony. bility of these products results from the carbon-rich acid In the present application, valency is to be understood portion and from the alkoxyalkanol or polyol. Accord as the number m of electrons which a metal can release, ingly, this patent does not tackle the problem of con 65 with formation of a metal ion carrying an m-fold verting salts, by means of only one complexing reagent, charge, and is familiar to those skilled in the art.
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