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    Production of 1,3,4-thiadiazoles
    51.
    发明专利
    Production of 1,3,4-thiadiazoles 未知

    公开(公告)号：GB989759A

    公开(公告)日：1965-04-22

    申请号：GB677763

    申请日：1963-02-20

    Applicant: BASF AG

    Inventor： WEIDINGER HANS ,  EILINGSFELD HEINZ

    IPC: C07D209/48 ,  C07D285/12 ,  C07D417/04 ,  C08K5/46 ,  C09B1/00 ,  C09B1/06 ,  C09B1/22

    Abstract: In a process for the production of 1,3,4-thiadiazoles a monothiodiacyl hydrazine having the formula in which R1 denotes a hydrogen atom or an aliphatic, cycloaliphatic, araliphatic, non-vattable aromatic or heterocyclic radical, any of which may be substituted by groups or atoms which are inert under the reaction conditions or the radical in which R denotes an alkylene or phenylene radical and R2 denotes an aliphatic, cycloaliphatic, araliphatic, non-vattable aromatic or heterocyclic radical, any of which may be substituted by groups or atoms which are inert under the reaction conditions, or the radical in which R denotes an alkylene or phenylene radical and R1 has the meaning given above, on the reaction mixture obtained by reacting an appropriate carboxylic acid hydrazide with dithiocarboxylic acids or esters thereof, thiocarboxylic acid esters, N-succinyl-thiocarboxylic amides or N - phthalythiocarboxylic amides, is heated in a solvent at 20 DEG to 150 DEG C., preferably 50 DEG to 100 DEG C. Examples relate to the preparation of 2,5-diphenyl-; 2-phenyl-5-[41 - nitrophenyl]-; 2 - phenyl - 5 - [41 - aminophenyl]-; 2 - phenyl - 5 - [21 - hydroxyphenyl]-; 2 - phenyl - 5 - [g - pyridyl] -; 2 - methyl - 5 - phenyl-; 2-cyanoethyl-5-phenyl-; 2-phenyl-5-[31 - cyano - phenyl] - ; 2 - [p - nitrophenyl] - 5 - [p - chlorophenyl] - ; 2 - phenyl - 5 - [p - chlorophenyl]- ; 2-[o-hydroxyphenyl] -5-[p-methoxyphenyl] - ; 2 - phenyl - 5 - [p - methoxyphenyl]- and 2 - phenyl - 1,3,4 - thiadiazoles and various anthraquinone dyes (see Division C4). Monothiodiacyl hydrazines employed as starting materials may be prepared by reacting carboxylic hydrazides with dithiocarboxylic acids or esters thereof, thiocarboxylic acid esters, N-succinylthiocarboxylic amides or N-phthalythiocarboxylic amides. Thiobenzoyl hydrazine is obtained by reacting thiobenzoic acid ethyl ester with benzoic acid hydrazide. N - phthalyl - p - chlorothiobenzamide is obtained by reacting phthalyl chloride with p-chlorothiobenzamide. N - phthalyl - p - methoxythiobenzamide is obtained by an analogous process. N,N1 - diphthalyldithioterephthalic diamide is obtained by reacting phthalyl chloride with dithioterephthalic diamide.ALSO:The invention comprises 2-[11-amino-21-anthraquinonyl] - 5 - phenyl - 1,3,4 - thiadiazole, 2 - [11,41 - diamino - 21 - anthraquinonyl] - 5 - phenyl - 1,3,4 - thiadiazole and the compounds of the formulae and a process from the production of 1,3,4-thiadiazoles wherein a monothiodiacylhydrazine having the general formula in which R1 denotes a hydrogen atom or an aliphatic, cycloaliphatic, araliphatic, vattable on non-vattable heterocyclic radical, any of which may be substituted by groups or atoms which are inert under the reaction conditions or the radical in which R denotes an alkylene or phenylene radical and R2 denotes an aliphatic, cycloaliphatic, aliphatic, araliphatic, vattable or non-vattable aromatic or heterocyclic radical any of which may be substituted by groups or atoms which are inert under the reaction conditions or the radical in which R denotes an alkylene or phenylene radical and R1 has the meaning given above, on the reaction mixture obtained by reacting an appropriate carboxylic acid hydrazide with dithiocarboxylic acids or esters thereof, thiocarboxylic acid esters, N-succinyl thiocarboxylic amides or N-phtholyl-thiocarboxylic amides, is heated in a solvent at 20 DEG to 150 DEG C., preferably at 50 DEG to 100 DEG C. In Example (14) 2-[11-amino-21 - anthraquinonyl] - 5 - phenyl - 1,3,4 - thiadiazole is obtained by reacting N-phthalyl thiobenzamide with 1-amino-anthraquinone-2-carboxylic acid hydrazide in the presence of N-methylpyrrolidone with subsequent addition of p-toluene sulphonic acid and heating the compound dyes cotton bluish red shades. Additional examples are furnished and starting materials listed.

    New water-soluble dyes containing substituted acylamino groups
    52.
    发明专利
    New water-soluble dyes containing substituted acylamino groups 未知

    公开(公告)号：GB958746A

    公开(公告)日：1964-05-27

    申请号：GB1432762

    申请日：1962-04-13

    Applicant: BASF AG

    Inventor： EILINGSFELD HEINZ ,  LUETZEL GERHARD ,  ROHLAND WERNER ,  TARTTER ARNOLD ,  WEIDINGER HANS ,  WEISSAUER HERMANN

    IPC: C07D233/56 ,  C09B1/36 ,  C09B43/00 ,  C09B47/08 ,  C09B69/00

    Abstract: The invention comprises dyes of the general formula: in which D denotes the radical of a dye of the azo, anthraquinone or phthalocyanine series, Y denotes a linear or branched unsubstituted or substituted alkylene group having at least two carbon atoms, R1 denotes a hydrogen atom or an alkyl, hydroxyalkyl, halo alkyl, cyanoalkyl, cycloalkyl, aralkyl or aryl radical, R2 denotes a hydrogen atom or an alkyl radical, R3 denotes an aliphatic hydrocarbon radical which may be substituted and/or polyvalent, Z denotes an unsubstituted or substituted ethylene or vinylene group, n denotes a whole number which is greater than 1 and X\sKX denotes an anion of a mineral acid, preferably a chloride or bromide ion. The characteristic heterocyclic radical in the dyes may be derived from polyvinylimidazole. In Examples (4) and (8) anthraquinones of the formula: are reacted with polyvinylimidazole to obtain blue and red dyes and in Example (11) b -chloropropionyl-p-amino-anilide is reacted with polyvinylimidazole and the product is diazotised and coupled with 1-hydroxynaphthalene-4-sulphonic acid to obtain a red dye.ALSO:The invention comprises any dye of the general formula in which D denotes the radical of a dye of the azo, anthraquinone or phthalocyanine series, Y denotes a linear or branched unsubstituted or substituted alkylene group having at least two carbon atoms, R1 denotes a hydrogen atom or an alkyl, hydroxyalkyl, haloalkyl, cyanoalkyl, cycloalkyl, aralkyl or aryl radical, R2 denotes a hydrogen atom or an alkyl radical, R3 denotes an aliphatic hydrocarbon radical which may be substituted and/or polyvalent, Z denotes an unsubstituted or substituted ethylene or vinylene group, n denotes a whole number which is greater than or equal to 1 and X(-) denotes an anion of a mineral acid, preferably a chloride or bromide ion and processes for the preparation thereof wherein (a) a dye or dye intermediate of the general formula in which D1 denotes the radical of a water-soluble dye of the azo, anthraquinone, or phthalocyanine series or the radical of an intermediate of such a dye and A denotes a chlorine or bromine atom is reacted with a compound of the general formula and when a dye intermediate has been used is completed into a dye by diazotization and (or coupling or by condensation or (b) a dye or dye intermediate of the general formula is reacted with an acid halide containing a cation of the general formula and when a dye intermediate has been used the reaction product is completed into a dye by diazotization and/or coupling or by condensation. The initial dyes or dye intermediates preferably contain one or more water-solubilizing groups, e.g. sulphonic, sulphonamide or sulphone groups, The characteristic heterocyclic radical in the dyes may be derived from such compounds as N-vinylimidazole or the N-methyl or N-ethyl derivatives thereof, polyvinylimidazole and N-hydroxyethyl-2-ethylimidazoline. Halo-alkylcarbonamide groups specified are derived from a - and b -bromo- and chloro-propionamides, a -, b - and g -bromo or chlorobutyramides. Among the many starting materials specified are azo dyes such as 1-aminobenzene - 4 - sulphonic acid --> 2 - (b -chloro - propionylamino) - 5 - hydroxynaphtholene - 7 - sulphonic acid and 1 - amino - 3 - (b - chloropropionylamino) - benzene --> 1 - (4-sulphophenyl) - 3 - methylpyrazolone, 1,4-diaminoanthraquinone - 2 - sulphonic acid, reaction products of 1-amino-4-bromanthraquinone - 2 - sulphonic - or 2 - carboxylic acid with aromatic amines such as 1,4-diaminobenzene, 1,3 - diaminobenzene - 4 - sulphonic acid, 4,41 - diamino - diphenylsulphide - 2,21-disulphonic acid, 4,41 - diaminostilbene - 2,21-disulphonic acid, 4,41-diaminodiphenylamine, or aliphatic diamines such as ethylene or propylene diamines, reaction products of leuco-1,4 - diamino - or - dihydroxyanthraquinones with aromatic diamines, e.g. 1,4-diaminobenzene - 2 - sulphonic acid. Examples of suitable pthalocyanine starting materials are mono-, di- or tetrachlorophthalocyanine, tetraphenylsulphonyl - copper phthalocyanine, tetramino - copper phthalocyanine di -, tri - and tetrasulphonic acids, reaction products of halomethyltetrazaporphins with amino phenols or aminophenolsulphonic acids and reaction products of aromatic or aliphatic primary or secondary diamines or their sulphonic acids with tetrazaporphinsulphonic acid halides. Acid binding agents may be employed in the reactions. The dyes are suitable for dyeing and printing materials of wool, silk, synthetic polyamides, polyurethanes, leather and natural or regenerated cellulose. In dyeing cellulose a process including treatment with basic substances and steam or hot air may be used. Examples are furnished.

    Water-soluble azo dyes
    59.
    发明专利
    Water-soluble azo dyes 未知

    公开(公告)号：GB1011985A

    公开(公告)日：1965-12-01

    申请号：GB515563

    申请日：1963-02-08

    Applicant: BASF AG

    Inventor： WEIDINGER HANS ,  EILINGSFELD HEINZ

    IPC: C09B62/085

    Abstract: The invention comprises dyes of the general formula in which R denotes a hydrogen atom and R1 denotes a group of the general formula -N = NF, or conversely R denotes a group of the general formula -N = N-F and R1 denotes a hydrogen atom, F being a radical of a compound capable of coupling and containing one or two sulphonic groups and processes from the preparation thereof wherein diazotized 2 - phenyl - 4 - (3 - or 4 - aminophenylamino) - 6 - chloro - 1,3,5 - triazine is coupled with a compound containing one or two sulphonic acid groups and being capable of coupling with diazotized compounds to form azo dyes. In examples, 2-phenyl-4-(3-aminophenylamino) - 6 - chloro - 1,3,5 - triazine is diazotized and coupled with 1-(2-chloro-5-sulphophenyl) - 3 - methylpyrazole - (5) or with 1 - hydroxynaphthalene - 4 - sulphonic acid (1,2); whilst 2 - phenyl - 4 - (4 - aminophenylamino) - 6 - chloro - 1,3,5 - triazine is diazotized and coupled with 1-(2-chloro-5-sulphophenyl) - 3 - methylpyrazolone - (5). The dyes dye native and /or regenerated cellulose. The diazo components are prepared by the process of Specification 1,011,984.

    Production of thiocarboxylic acid esters
    60.
    发明专利
    Production of thiocarboxylic acid esters 未知

    公开(公告)号：GB976057A

    公开(公告)日：1964-11-25

    申请号：GB1500263

    申请日：1963-04-17

    Applicant: BASF AG

    Inventor： WEIDINGER HANS ,  EILINGSFELD HEINZ

    Abstract: Thioesters (I) are obtained by first treating at between -10 and +40 DEG C. in presence of an organic solvent or amidedichloride (II) with a compound R2XH and then reacting the intermediate so formed at between -10 and +60 DEG C. in an inert solvent with hydrogen sulphide. In the formulae, R1 is H, a C1-4 aliphatic radical, a C6-8 cycloaliphatic radical or a C6-14 carboxylic aromatic radical; R2 is C1-4 alkyl (optionally bearing carboxyl) or C6-8 carbocyclic aryl, R3 and R4 are C1-3 alkyl or with N constitute part of a C5 or C6 heterocyclic ring and X is O or S. Details are given for the preparation of the required amide, dichlorides (II) from the corresponding amides and phosgene.

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