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    Aromatic esters of quaternary ammonium alkyl sulphonic acids and fungicidal compositions
    63.
    发明专利
    Aromatic esters of quaternary ammonium alkyl sulphonic acids and fungicidal compositions 未知

    公开(公告)号：GB964689A

    公开(公告)日：1964-07-22

    申请号：GB4130762

    申请日：1962-11-01

    Applicant: BASF AG

    Inventor： DISTLER HARRY ,  LEIBNER GERHARD ,  POMMER ERNST-HEINRICH ,  STUMMEYER HERBERT

    IPC: A01N41/08

    Abstract: The invention comprises compounds of the formula: in which Ar is an aromatic radical which may be substituted by one or more halogen atoms, alkyl, nitro, hydroxyl, acyl, formyl, methoxy, ethoxy, nitrile, acylamino or thiocyanate groups, X is hydrogen, an alkyl radical or halogen and X2 is hydrogen, R1, R2 and R3 are alkyl radicals and Y is an anion, such as I-, Cl-, Br-, CH3OSO3-, CH2 = CHSO3-, acetate or sulphate. The compounds may be made by reacting a sulphonic ester ArOSO2-CH=CH2 with a secondary amine R1.NH.R2 forming Ar.OSO2.CH2.CH2 N.R1(R2) followed by alkylation with YR3. An example describes the reaction of the phenyl ester of N-dimethyl-b -aminoethane sulphonic acid with dimethyl sulphate to form the phenyl ester of N-trimethyl b -aminoethanesulphonic acid methyl sulphate. Suitable starting materials are listed in which the phenyl nucleus is substituted as indicated above. Specification 910,377 is referred to.ALSO:Fungicidal compositions comprise a compound of the formula in which Ar is an aromatic radical which may be substituted by one or more halogen atoms, alkyl, nitro, hydroxyl, acyl, formyl, methoxy, ethoxy, nitrile, acylamino or thiocyanate groups, X1 is hydrogen, an alkyl radical or halogen and X2 is hydrogen, R1, R2 and R3 are alkyl radicals and Y is an anion, such as I-, Cl-, Br-, CH3OSO3-, CH2=CHSO3-, acetate or sulphate, with liquid or solid diluents or carriers, such as water and organic liquids or talc. Dispersing and wetting agents may be present and other active substances with acaricidal, insecticidal, ovicidal, herbicidal, fungicidal or bactericidal action may be added. Examples are given. Specification 910,377 is referred to.

    New monoazo dyes containing hydrazinyl substituted triazine residues
    65.
    发明专利
    New monoazo dyes containing hydrazinyl substituted triazine residues 未知

    公开(公告)号：GB929097A

    公开(公告)日：1963-06-19

    申请号：GB498461

    申请日：1961-02-10

    Applicant: BASF AG

    Inventor： BAUMANN HANS ,  DISTLER HARRY ,  MERKEL KARL ,  TARTTER ARNOLD ,  WEISSAUER HERMANN ,  WERNER HEINZ-ULRICH

    IPC: C09B62/085

    Abstract: 2-(4,6-Dihydrazino-1,3,5-triazinyl-2)- and 2-[4,6- di(phenylhydrazino)- 1,3,5-triazinyl- 2) -amino- 5-hydroxynaphthalene- 7-sulphonic acids are prepared by condensing cyanuric chloride with an equimolar amount of 2-amino-5-naphthol-7-sulphonic and then reacting the primary condensate with 2 molar proportions of hydrazine or phenylhydrazine. Specifications 842,802 and 872,249 are referred to.ALSO:The invention comprises monoazo dyes which contain attached by way of an amino group at least one group of formula:- wherein X is the radical of hydrazine or a substituted hydrazine and Y is a halogen atom, an amino group, a hydroxyl group, a mercapto group, the radical of hydrazine or a substituted hydrazine, or an aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic radical attached by way of an oxygen, sulphur or nitrogen atom to the triazine ring. The dyes are prepared by reacting a trihalo-s-triazine in any sequence with (a) a monoazo dye or an intermediate of such a dye containing a primary or secondary amino group and (b) hydrazine or a substituted hydrazine to form a secondary condensation product, if desired exchanging the final halogen atom by treatment with alkali, ammonia, an amine, alcohol, phenol or mercaptan or hydrazine or hydrazine derivative and when an intermediate has been used converting this into the dye by coupling. The dyes may be treated with formaldehyde to prepare the corresponding methylol compounds as described in Specifications 842,802 and 872,249 and the methylol compounds may also be etherified or esterified. Specified substituted hydrazines include methylhydrazine, N1,N-dimethylhydrazine, acetylhydrazine, phenylhydrazine and its sulphonic acids, maleic acid hydrazide, N-aminoethylurethane, 2,4,6-trihydrazino-1,3,5-triazine, aminoguanidine, hydrazo-dicarboxylic acid amide, pyrazoline, N-aminopiperazine and the compound of formula The dyes may be used to colour natural and synthetic polyamide fibres, leather, paper and, preferably, cellulose. The dyeings may be carried out in the presence of acid substances and hardenable aminoplast-forming substances, possibly together with an aldehyde or a substance yielding an aldehyde, and fixed by a heat treatment. In examples: (1) the monoazo dye 1-aminobenzene-2-sulphonic acid--->2-(8 -hydroxy - 3,6 - disulphonaphthyl - 1 - amino) -4,6-dichloro-s-triazine is reacted with an equimolar amount of hydrazine hydrate; (2) cotton fabric is padded with an aqueous solution containing the dye obtained in (1), 1,3-dimethylol -5-methylperhydrotriazone-(2) and monoammonium phosphate, squeezed out, dried and heated at 145 DEG C. for 8 minutes; (3) a cotton fabric which has been treated with a caustic soda solution is padded with a liquor containing a dyestuff, methylol or methylene ether, the tetramethyl ether of tetramethylolmelamine, the ammonium salt of polyacrylic acid, polyglycol ether, sodium isopropylnaphthalene sulphonate and a mixture of diethanolamine and triethanolamine hydrochlorides, squeezed out and dried and heated on flat frames at 145 DEG C. A dyed crease resistant fabric is obtained. Further examples of the dyes are specified.

    Alkane sulphonic acid esters substituted in ª -position by ether groups and their production
    66.
    发明专利
    Alkane sulphonic acid esters substituted in ª -position by ether groups and their production 未知

    公开(公告)号：GB923766A

    公开(公告)日：1963-04-18

    申请号：GB3197461

    申请日：1961-09-06

    Applicant: BASF AG

    Inventor： MUELLER WERNER ,  DISTLER HARRY ,  PALM ALBERT

    IPC: C07C309/09 ,  C07C309/68

    Abstract: The invention comprises compounds of formula R1-O-CR2R3-CHR4-SO2-O-R5 which contain at least nine carbon atoms, where R1 is a C1-C20 alkyl group, a C3-C20 alkenyl group, a cycloalkyl group with 5 to 12 carbon atoms in the ring, a C2-C12 hydroxy alkyl group, a C3-C12 alkoxyalkyl group, a C4-C23 dialkylaminoalkyl group or an alkylarylaminoalkyl group with up to 23 carbon atoms; R2-R4 are hydrogen atoms or C1-C3 alkyl groups; R5 is a C1-C18 alkyl group, a C6-C15 aryl group, a C7-C13 alkoxyaryl group, a C6-C12 halogenaryl group or a C7 thiocyanoaryl group. The invention also includes a process for making compounds of the above formula, without the restriction to 9 upon the total number of carbon atoms in their molecules, by treating the corresponding vinyl sulphonic acid ester with an excess of alcohol in the presence of 0.02-0.1 equivalent per mol. of ester of an alkali or alkaline earth metal alcoholate, a dry alkali hydroxide or a quaternary ammonium base of the formula [R1R11NR111R1111]+ OH-wherein R1, R11 and R111 are C1-C3 alkyl groups and R1111 is a C6-C10 aryl group, a C7-C9 aralkyl group or a cycloalkyl group having 5 to 12 carbon atoms in the ring. Inert solvents may be present. The temperature may be in the range -10 to 100 DEG C. but preferably the reactants are mixed at a lower temperature and slowly heated. The alcohol may be present in 1.3 times the stoichiometrical amount but is generally used in considerable excess, e.g. 2 to 8 times the stoichiometrical amount. The esters may be hydrolysed to form the free acids or salts thereof which have surface-active properties when R1 has at least 6 carbon atoms. Preferred starting esters are derived from vinylsulphonic acid, a -methylvinylsulphonic acid and 1-propene sulphonic acid and from phenols and naphthols which may contain one to three inert groups such as alkyl, alkoxy, halogen and thiocyanate groups. Typical of specified alcohols are propanol, 2-ethylhexanol, allyl alcohol, palmityl alcohol, butane-1,4-diol, dodecane-1, 12-diol, glycol monomethyl ether, triglycol, methylstearylaminoethanol, cyclopentanol, cyclooctanol, benzyl alcohol and phenylmethyl carbinol. Esters containing aryl residues in the ester group and 4-20 carbon atoms in the ether group are plasticisers for polyvinyl chloride. Examples given include the preparation of b -allyloxy-ethane sulphonic acid cresyl ester, b -nonyloxy-ethanesulphonic acid methyl ester, b (NN-dimethyl-2-aminoethoxy)-ethane sulphonic acid cresyl ester, b -cyclohexyloxyethanesulphonic acid-a -naphthyl ester, b -allyloxy-ethanesulphonic acid-2-chlorophenyl ester, and also the use of vinylsulphonic acid o-bromophenyl ester, vinylsulphonic acid p-iodophenyl ester, vinylsulphonic acid p-fluorophenyl ester and vinylsulphonic acid p-thiocyanophenyl ester.

    Organic nitrogen base salts of vinyl sulphonic acid
    67.
    发明专利
    Organic nitrogen base salts of vinyl sulphonic acid 未知

    公开(公告)号：GB922388A

    公开(公告)日：1963-03-27

    申请号：GB79461

    申请日：1961-01-09

    Applicant: BASF AG

    Inventor： DISTLER HARRY ,  MUELLER WERNER ,  WERNER HEINZ-ULRICH

    IPC: C07C41/16 ,  C07C209/18 ,  C07C309/20 ,  C07D213/20 ,  C07D215/10 ,  C07D215/26 ,  C07D295/02 ,  C07D295/037 ,  C07D295/04 ,  C07D521/00 ,  C08F28/00

    Abstract: Aqueous polymer dispersions are prepared from salts of vinyl sulphonic acid with organic nitrogen bases. The salts have the formula where R1 is a monovalent hydrocarbon radical which may be substituted by halogen or a hydroxyl group or acylated hydroxyl group or may contain ether linkages; R2, R3, and R4 may be as R1 or may be hydrogen; R4 may be a hydrocarbon radical substituted by a group of formula R1 and R2 may be polymethylene groups which connect the nitrogen atom of formula I with a group of formula the substituents R5, R6 and R7 being hydrogen, hydrocarbon radicals or hydroxyalkyl radicals, and A(-) an anion, particularly that of vinyl sulphonic acid; R2 and R3 may form a 5 to 7 membered heterocyclic ring with the nitrogen atom of formula I; and R1, R2 and R3 may be components of a 5 or 6 membered ring containing the nitrogen atom of formula I. In Examples A to E aqueous dispersions of copolymers are prepared from:-trimethyl-phenyl-ammonium vinyl sulphonate and n-butyl acrylate; trimethyl-cyclohexyl-ammonium vinyl sulphonate, vinyl acetate and n-butyl acrylate; methyl-triethanol-ammonium-vinyl sulphonate, vinyl propionate and n-butyl acrylate; a salt derived from vinyl sulphonic acid methyl ester and the reaction product of 1 mol. of diethylamine with 4 mols. of ethylene oxide, ethyl acrylate and vinylidene chloride; diethyl ammonium vinyl sulphonate, ethyl acrylate and acrylic acid; potassium persulphate is used to initiate the copolymerization.ALSO:The invention comprises salts of vinyl sulphonic acid with organic nitrogen bases. The salts have the formula where R1 is a monovalent hydrocarbon radical which may be substituted by halogen or a hydroxyl group or acylated hydroxyl group or may contain ether linkages; R2, R3, and R4 may be as R1 or may be hydrogen; R4 may be a hydrocarbon radical substituted by a group of formula R1 and R2 may be polymethylene groups which connect the nitrogen atom of formula I with a group of formula R5, R6 and R7 being hydrogen, hydrocarbon radicals or hydroxyalkyl radicals, and A(-) an anion, particularly that of vinyl sulphonic acid; R2 and R3 may form a 5 to 7 membered heterocyclic ring with the nitrogen atom of formula I; and R1, R2 and R3 may be components of a 5 or 6 membered ring containing the nitrogen atom of formula I. The salts may be prepared by neutralizing the nitrogen base with vinyl sulphonic acids; or by reacting the nitrogen base with a vinyl sulphonic acid ester, the hydrocarbon radical of the alcoholic component of the ester being transferred to the nitrogen atom. In examples there are prepared salts including N-methyl-8-hydroxyquinolinium vinyl sulphonate, ethyl-dimethylanilinium vinyl sulphonate, salts from ethyl and butyl esters of vinyl sulphonic acid and 4,41-bis-(dimethylamino-diphenyl)methane, trimethylcyclohexylammoniumvinyl sulphonate, salt of dimethyl palm kernel fatty amine, N-methyl-pyridinium vinyl sulphonate, N-methyl-quinolinium vinyl sulphonate, Nmethyl-vinylimidazolium vinyl sulphonate, Nmethyl-g -picolinium p vinyl sulphonate, Nmethyl-quinaldinium vinyl sulphonate; salts of vinyl sulphonic acid and pyridine, crotylamine, 4-isopropyl-aniline, a -naphthylamine, 4-methoxy-N,N- dimethylaniline, 1-hydroxy2-amino-propane, piperazine, N-methyl pyrrole, pyrazole, thiazole, oxazole, morpholine, thiomorpholine, hexamethylene imine, diphenylamine, N- methylpyrrolidine, methyl oxazolidine, alkoxyamines, alkanolamines, reaction products of alkylene oxides with amines; and salts from simple amines and diamines.

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