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    Dyes of the tetrazaporphin series and their production
    112.
    发明专利
    Dyes of the tetrazaporphin series and their production 未知

    公开(公告)号：GB926377A

    公开(公告)日：1963-05-15

    申请号：GB2736460

    申请日：1960-08-08

    Applicant: BASF AG

    Inventor： ROHLAND WERNER ,  SCHROEDEL RUDOLF ,  TARTTER ARNOLD ,  FEDERKIEL WILHELM

    Abstract: The sulphuric semiester of m- or p-amino-b -hydroxypropionyl-anilide is made by esterifying with chlorosulphonic acid m- or p-amino-b -hydroxypropionyl-anilide obtained by reducing m- or p-nitro-b -hydroxypropionyl-anilide. These are prepared by hydrolysing m- or p-nitro-b -formoxy- or acroyloxy-propionyl-anilides obtained by condensing m- or p-nitraline with b -formoxypropionyl or b -acroyloxypropionyl chlorides. The sulphuric acid semiester of p-amino-b -hydroxypropionyl-anilide is also made by treating with sulphuric acid p-amino-b -acetoxypropionyl-anilide prepared by reduction of p-nitro-b -acetoxypropionyl-anilide obtained by condensing p-nitraniline with b -acetoxypropionyl chloride.ALSO:The invention comprises dyes of the formula:-Z-(D)n where Z is a tetrazaporphin radical which may be further substituted, n is an integer from 1 to 4 and D is a radical of the formula:- where R1 is hydrogen or the radical of sulphuric acid or phosphoric acid, and particularly dyes which in the form of the free acids have the formula:- where A is a tetrazaporphin radical, n is an integer from 1 to 4, m is an integer from 0 to 4, (n+m) is an integer from 1 to 8, D is the group HO3S-O-CH2-CH2CO.NH-and E is a direct linkage, an alkylene group, a group, a -CO-NH-Q- group or an -SO2-NH-Q-group where G is arylene and Q is alkylene or arylene which may contain sulphonic acid groups. The tetrazaporphin radicals include di- and tribenzotetrazaporphins and metal or metal-free phthalocyanines. The dyes are made by treating an amide of the formula:- where R11 is hydrogen or an aliphatic, cycloaliphatic, araliphatic or aromatic radical and Y is a tetrazaporphin radical which may contain up to three additional groups and other substituents, in the presence of an at least stoichiometric amount of water with ammonia, an amine, a hydrazine or hydroxylamine and if desired esterifying the product of the formula with sulphuric acid or phosphoric acid or, when R1 is to be the radical of sulphuric acid, by treating the amide of the Formula VII(a) with 90 to 100% sulphuric acid at temperatures between 0 DEG and 100 DEG C. The dyes may also be made by reacting tetrazaporphins having n exchangeable halogen atoms, e.g. as chlormethyl, sulphonic acid halide or carboxylic acid halide groups, with amines of the formula:- where Y1 is an aryl radical containing an acylatable amino group. Examples are given. The amides of the Formula VII(a) above are made by condensing a tetrazaporphin containing amino groups with b -acyloxypropionic acid halides such as b -formoxy-, b -acetoxy- or b -acroyloxy-propionyl chlorides. The dyes dye and print foils, films and textile materials of wool, silk, polycaprolactam, linear polyamides, natural or regenerated cellulose, leather and paper in blue to green shades. The dyes containing sulphuric acid or phosphoric acid ester groups are reactive with materials of cellulose and polyvinyl alcohol.

    New azo dyes containing amido groups substituted by unsaturated radicals
    113.
    发明专利
    New azo dyes containing amido groups substituted by unsaturated radicals 未知

    公开(公告)号：GB916697A

    公开(公告)日：1963-01-23

    申请号：GB3145060

    申请日：1960-09-13

    Applicant: BASF AG

    Inventor： ROHLAND WERNER ,  LUDSTECK DIETER ,  MUELLER ROLAND ,  FEDERKIEL WILHELM

    IPC: C09B62/006

    Abstract: 1-Aminobenzene - 4 - sulphonic acid (3,4-dichlorobutene-(2)yl amide) is obtained by reacting 1 - acetyl-aminobenzene-4-sulphonic acid chloride with 1 - acetylamino - 3,4 - dichlorbutene-(2) and hydrolysing the product with aqueous hydrochloric acid. The hydrochloride of 1-amino-3,4-dichlorbutene-(2) is obtained by reacting 1,3,4-trichlorbutene-(2) with hexamethylenetetramine and treating a methanol solution of the product with hydrogen chloride. The hydrochlorides of other aminohalogenbutenes-(2) and -butines-(2) are stated to be prepared by analogous methods. The amine of the formula is obtained as sulphate by reacting 1-aminobutine-2-(ol)-(4) with 1-acetylaminobenzene-4-sulphonic acid, treating the product with hydrogen chloride and finally sulphuric acid. Such compounds are employed as intermediates in the preparation of azo dyes (see Group IV(c)).ALSO:The invention comprises azo dyes of the formula [A-N=N-B-]-(X-NH-CH2-Y-CH2-Q)n in which A represents the radical of a diazotisable amine of the benzene, naphthalene, azobenzene, benzeneazonaphthalene or heterocyclic series, B represents the radical of a compound capable of coupling of the benzene, naphthalene, acetoacetic acid ester, acetoacetic acid anilide, benzeneazonaphthalene or heterocyclic series, X represents a -CO- or -SO2- radical, Y represents one of t he radicals -C=C-, -CH=CH-, -CH=CCl-, -CH=CBr- and -CCl= CCl-, Q represents a halogen atom, an -OSO3H radical or a radical of the formula Z represents a halogen atom or the group HSO4 and n represents 1 or 2, and a process for the preparation thereof wherein one mol of an azo dye of the formula [A-N=N-B-]-(-X-D)n is reacted with n mols of an amine of the general formula H2N-CH2-Y-CH2-Q or a diazotised amine of the general formula (Q-CH2-Y-CH2-NH-X-)p-A-NH2 is coupled with a compound capable of coupling of the general formula H-B-(X-NH-CH2-Y-CH2-Q)n-p and the reaction product is optionally reacted with a pyridine, A. B, X, Y and Q and n having the meanings given above, D representing a halogen atom and p representing 0, 1 or 2. Heterocyclic compounds specified for use as starting materials include pyrazolones, quinolines and thiazoles. The amines from which the unsaturated amido groups may be derived include such compounds as 1-amino-4-chloro- and -4-bromo-butine-(2)-, 1-amino-4-chloro- and 4-bromo-butene-(2), 1-amino-3,4-dichlorobutene and 1-amino-2.3.4-trichlorobutene. The products of the invention may be used to dye natural cellulose, e.g. cotton, or regenerated cellulose, animal fibres, e.g. wool and silk, synthetic polyamides, e.g. nylon and synthetic polyesters, e.g. polyethylene terephthalate and hexahydroterephthalate. The examples illustrate the preparation of the dyes, including preparation on the fibre and their use in dyeing processes generally.

    Process for the production of n-substituted ª--hydroxypropionyl amides and their esters with strong oxygencontaining acids
    114.
    发明专利
    Process for the production of n-substituted ª--hydroxypropionyl amides and their esters with strong oxygencontaining acids 未知

    公开(公告)号：GB915457A

    公开(公告)日：1963-01-16

    申请号：GB2736360

    申请日：1960-08-08

    Applicant: BASF AG

    Inventor： ROHLAND WERNER ,  SCHROEDEL RUDOLF ,  TARTTER ARNOLD ,  FEDERKIEL WILHELM

    IPC: C07F9/09 ,  C09B43/00 ,  C09B62/473

    Abstract: N-substituted b -hydroxy-propionamides and esters thereof of formula R1-O-CH2-CH2-CO-NH-Y (I) wherein R1 is hydrogen or the radical of sulphuric, phosphoric or an arylsulphonic acid and Y is a substituted aromatic radical are prepared by (a) partially saponifying an esterified b -hydroxypropionylamide of formula R11-CO-O-CH2-CH2-CO-NH-Y (II wherein R11 is a C1-C4 aliphatic radical with ammonia, an amine, a hydrazine, hydroxylamine or mixtures thereof preferably in the presence of a solvent and, if desired, esterifying the resultant b -hydroxypropionamide with an appropriate acid; (b) heating a compound of formula II wherein R11 is hydrogen with a C1-C5 aliphatic alcohol and if desired esterifying the resultant b -hydroxypropionamide with an appropriate acid or (c) reacting a compound of formula II with 90 to 100% sulphuric acid at 0 DEG -100 DEG C. to give the esters of formula HO3S-O-CH2-CH2-CO-NH-Y The compounds may be used in the preparation of azo dyes (see Group IV(c)). In examples: (1) m- or p-nitroaniline is condensed with diacrylic acid chloride to give diacrylic acid m- or p-nitroanilide which is treated with ammonia in methanol to give b -hydroxypropionyl-m-or-p-nitroanilide which is reduced to b -hydroxypropionyl-m-or-p-aminoanilide and esterified with chlorosulphonic acid to give the sulphuric acid ester of b -hydroxypropionyl - m-or-p - aminoanilide (b -hydroxypropionyl-p-nitroanilide is also converted into its p-toluene-sulphonic acid ester); (2) as in (1) p-chloroaniline is converted successively into diacrylic acid p-chloroanilide and b -hydroxypropionyl-p-chloroanilide; (3) 2-methoxy-4-nitroaniline or 2-amino-5-naphthol-7-sulphonic acid is acylated with b -acetoxypropionylchloride to give the corresponding amide which is treated as in (1) to give b -hydroxypropionyl-(4-nitro-2-methoxyphenyl)amide, which is reduced to b -hydroxypropionyl - (4 - amino - 2 methoxyphenyl)-amide, and 2 - b hydroxypropionylamino-5 - naphthol - 7 - sulphonic acid; (4) m- or p-nitroaniline are acylated with b -formyloxypropionyl chloride to give b -formyl oxypropionyl-m- or p-nitroanilide which is treated as in (1) to yield b -hydroxypropionylm- or p-nitroanilide; (5) b -formyloxypropionylp-nitroanilide or -2-methoxy-4-nitroanilide is refluxed in methanol to give b -hydroxypropionyl-(4-nitro- or 4-nitro-2-methoxy-phenyl) amide; (6) hydrogenation of b -formyloxypropionyl-p-nitroanilide with Raney nickel and hydrogen in methanol solution under pressure gives b -hydroxypropionyl-p-aminoanilide; (7) b -formyloxy- or -acetoxy-propionyl-p-nitroanilide is reduced to b -formyloxy- or -acetoxypropionyl-p-aminoanilide which is reacted with sulphuric acid to give the sulphuric acid ester of b -hydroxypropionyl-p-aminoanilide; (8) as in (7) the b -acetoxypropionyl derivative of 2-amino-5-naphthol-7-sulphonic acid is converted into the sulphuric ester of 2-b -hydroxypropionylamino-5-naphthol-7-sulphonic acid.ALSO:Monoazo dyes containing b -hydroxypropionamide groups and ester derivatives thereof of formula R1-O-CH2-CH2-CO-NH-Y wherein R1 is hydrogen or the radical of phosphoric, an arylsulphonic or, preferably, sulphuric acid and Y is a monoazo dye residue are prepared by (a) partially saponifying an esterified b -hydroxypropionamide of formula R11-CO-O-CH2-CH2-CO-NH-Y (II) wherein R11 is a C1-C4 aliphatic radical with ammonia, an amine, a hydrazine, hydroxylamine or mixtures thereof, preferably in the presence of a solvent and, if desired, esterifying the resultant b -hydroxypropionamide; (b) heating a compound of formula II wherein R11 is hydrogen with a C1-C5 aliphatic alcohol and if desired esterifying the resultant b -hydroxypropionamide or (c) reacting a compound of formula II with 90 to 100% sulphuric acid at 0 DEG -100 DEG C. to give the esters of formula HO3S-O-CH2-CH2-CO-NH-Y. The dyes may also be prepared in the usual way from diazo and/or coupling components containing the groups, prepared by the above methods (see Group IV(b)). The invention also comprises the dyes of formulae:- 1-phenyl-3-methyl-5-pyrazolone; (2) the aminoazo dye obtained by saponification of the dye 1-amino-4-acetylaminobenzene --> 1-naphthol-4-sulphonic acid is acylated with diacrylic acid chloride, the acyl derivative treated with ammonia to give the b -hydroxypropionylamino-derivative which is esterified with chlorosulphonic or sulphuric acid; (3) the aminoazo dye used in (2) is reacted with b -formyloxypropionyl chloride and the acyl derivative is refluxed with methanol to give the b -hydroxypropionylamino-azo dye which may be esterified with sulphuric acid or heated with sulphuric acid to give the sulphuric acid ester. Further examples are given.

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