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    Production of aromatic carboxylic acids containing reactive chlorine atoms
    21.
    发明专利
    Production of aromatic carboxylic acids containing reactive chlorine atoms 未知

    公开(公告)号：GB1082479A

    公开(公告)日：1967-09-06

    申请号：GB783266

    申请日：1966-02-23

    Applicant: BASF AG

    Inventor： HAHN ERWIN ,  SEEFELDER MATTHIAS

    IPC: C07D239/30 ,  C07D277/68 ,  C07D285/08 ,  C09B62/02

    Abstract: Acid chlorides of carboxylic acids of the general formula HOOC-Ar-X-(Cl)n, where Ar is an aryl group, X is a 5- or 6-membered heterocyclic ring which may be fused with Ar, and n is 1 or 2, may be used to prepare reactive dyes. The specified dyes have the formulae (I) (II) (III) AND (IV) ALSO:Aromatic carboxylic acids having the formula HOOC-Ar-X-(Cl)n, where Ar represents an aryl group, X is 5- or 6-membered heterocyclic ring, which may be fused with Ar, and n is 1 or 2, are prepared by heating an aromatic trichloromethyl compound of the formula Cl3C-Ar-X-(Cl)n with concentrated formic acid at 40-120 DEG C. The heterocyclic moiety may be a thiadiazole, thiazole or pyrimidine residue, the aryl moiety a phenyl, biphenyl or naphthyl radical and the fused aryl/heterocyclic moiety a benzimidazole, benzothiazole or quinoline residue. The aryl and heterocyclic nuclei may be further substituted by, e.g., sulphonic or halogen groups. Examples describe the preparation of 3-(m-carboxyphenyl) - 5 - chlorothiadiazole - 1,2,4; 3 - (p - carboxyphenyl) - 5 - chlorothiadiazole-1,2,4; 2 - (m - carboxyphenyl) - 4,6 - dichloropyrimidine; 2 - (p - carboxyphenyl) - 4,6 - dichloropyrimidine; 4 - (p - carboxyphenyl) - 2,6- dichloropyrimidine; and 4 - (m - carboxyphenyl) - 2,6 - dichloropyrimidine. The tricloromethyl starting materials are made by photochemical chlorination of the corresponding methyl compounds.

    Production of azamonomethinecyanines of the benzthiazole series
    26.
    发明专利
    Production of azamonomethinecyanines of the benzthiazole series 未知

    公开(公告)号：GB940539A

    公开(公告)日：1963-10-30

    申请号：GB2642162

    申请日：1962-07-10

    Applicant: BASF AG

    Inventor： SEEFELDER MATTHIAS ,  REPPE HANS GERHARD

    IPC: C07D277/82 ,  C08K5/47 ,  C09B23/16 ,  G03C1/12

    Abstract: Azamonomethinecyanines of the formula where R1 and R2 are hydrogen, halogen or alkyl or alkoxy with 1-12 carbon atoms, R3 is alkyl with 1-12 carbon atoms and X- is an anion, are prepared by reacting a compound with at least a stoichiometric proportion of a strong acid at 100-250 DEG C., with or without an organic diluent. Specified starting materials are 3-methyl-, 3-ethyl-, 3-butyl-, 3,6-dimethyl-, 3-methyl-6-t-butyl-, 3-methyl-6-methoxy-, 3-ethyl-6-butoxy-, 3-methyl-5-chloro-, 3,6-dimethyl-4-chloro-, and 3,6-dimethyl-4-methoxybenzthiazolone-2-imide; other R groups are listed. Specified acids are HCl, HBr, H2SO4, H3PO4, up to C4-alkyl sulphuric acids, benzenesulphonic acid, naphthalenesulphonic acid, p-toluenesulphonic acid, and methane-, ethane- and propanesulphonic acid. Specifications 447,038 and 461,668 are referred to.

    Levelling agents for sulphur and vat dyeings
    27.
    发明专利
    Levelling agents for sulphur and vat dyeings 未知

    公开(公告)号：GB920149A

    公开(公告)日：1963-03-06

    申请号：GB3816361

    申请日：1961-10-25

    Applicant: BASF AG

    Inventor： HARTMARK BJARNE ,  REPPE HANS-GERHARD ,  ROKOHL RUDOLF ,  SEEFELDER MATTHIAS

    IPC: D06P1/22 ,  D06P1/30 ,  D06P1/52

    Abstract: Water-soluble polyamides are derived from (a) an aliphatic, cycloaliphatic or aromatic polyamine or a heterocyclic compound which contains at least two acylatable nitrogen atoms and (b) an a ,b -unsaturated carboxylic acid, an aliphatic polycarboxylic acid, an aliphatic polycarboxylic acid containing one or more hetero atoms or functional derivatives of these such as halides, anhydrides, amides or esters which are capable of amide formation. They are employed as levelling agents in dyeing with vat and sulphur dyes (see Group IV(c)). Specified (a) are phenylene diamines, xylylene diamines, toluylene diamines, 4,41-diaminodiphenylmethane, N,N1-di-(sec-butyl)-p-phenylene diamine, 1,5-naphthylene diamine and their hydrogenation products, 2-methylpiperazine, 2,5-diethylpiperazine and especially polyamines of the general formula: wherein R1 and R3 are hydrogen, alkyl or hydroxyalkyl radicals of 1-4 C-atoms or, when x is 2 and n is 0, together represent an ethylene radical; R2 is a hydrogen, alkyl or hydroxy-alkyl radical of 1-4 C-atoms; x and y are integers from 1 to 6 and n is an integer from 0 to 20, the sum of x and n being greater than or equal to 2. Especially preferred compounds of this type are ethylene diamine, hydroxyethyl-ethylene diamine, hexamethylene diamine, di-(aminopropyl)-ethylene diamines, diethylene triamine, N-propyl-diethylene diamine, triethylene tetramine, dipropylene triamine, tripropylene tetramine, N-methyl-dipropylene triamine, di-(ethylaminoethyl)-amine and piperazine. The specified compounds (b) are the acids: acrylic, methacrylic, crotonic, tiglic, malonic, succinic, glutaric, adipic, pimelic, suberic, maleic and fumaric also dipropyl ether-g ,g 1-dicarboxylic acid, thiodibutyric acid, ethylene diamine tetraacetic acid and nitrilotriacetic acid. The watersoluble polyamides may be prepared by condensing substances (a) with substances (b) in the presence or absence of inert solvents such as glycerol, polyglycols of b.p. above 160 DEG C. and tetrahydronaphthalene at 180 DEG -200 DEG C. for 30-60 minutes. The preferred proportions of reactants are chosen so that there are 1 to 1,5 1 DEG and/or 2 DEG amino groups for each carboxyl group or when using an unsaturated acid 1 to 1,5 1 DEG and/or 2 DEG amino groups for each carboxyl group and each reactive double bond. When using a ,b -unsaturated carboxylic acids small amounts of polymerization inhibitors such as hydroquinone and methylene blue may be added. The condensation of amines with acid halides may be carried out at room temperature in the presence of a proton acceptor such as pyridine or a 3 DEG aliphatic amine. The polyamides so formed have mean molecular weights of 600 to 1,500. Examples of the preparation of a number of compounds using some of the above-named reactants are given.ALSO:Water-soluble polyamides are derived from (a) an aliphatic, cycloaliphatic or aromatic polyamine or a heterocyclic compound which contains at least two acylatable nitrogen atoms and (b) an a ,b -unsaturated carboxylic acid, an aliphatic polycarboxylic acid, an aliphatic polycarboxylic acid containing one or more hetero atoms or functional derivatives of these such as halides, anhydrides, amides or esters which are capable of amide formation. They are employed as levelling agents in dyeing with vat and sulphur dyes (see Group IV(c)). Specified (a) are phenylene diamines, xylylene diamines, toluylene diamines, 4,41-diaminodiphenylmethane, N,N1-di-(sec-butyl)-p-phenylene diamine, 1,5-naphthylene diamine and their hydrogenation products, 2-methylpiperazine, 2,5-diethylpiperazine and especially polyamines of the general formula: Wherein R1 and R3 are hydrogen, alkyl or hydroxyalkyl radicals of 1-4 C-atoms or, when x is 2 and n is 0, together represent an ethylene radical; R2 is a hydrogen, alkyl or hydroxyalkyl radical of 1-4 C-atoms; x and y are integers from 1 to 6 and n is an integer from 0 to 20, the sum of x and n being greater than or equal to 2. Especially preferred compounds of this type are ethylene diamine, hydroxyethyl-ethylene diamine, hexamethylene diamine, di-(aminopropyl)-ethylene diamine, diethylene triamine, N-propyl-di-ethylene diamine, triethylene tetramine, di-propylene triamine, tripropylene tetramine, N-methyl-dipropylene triamine, di-(ethylamino-ethyl)-amine and piperazine. The specified compounds (b) are the acids: acrylic, methacrylic, crotonic, tiglic, malonic, succinic, glutaric, adipic, pimelic, suberic, maleic and fumaric also dipropyl ether-g ,g 1-dicarboxylic acid, thiodibutyric acid, ethylene diamine tetra-acetic acid and nitrilotriacetic acid. The water-soluble polyamides may be prepared by condensing substances (a) with substances (b) in the presence or absence of inert solvents such as glycerol, polyglycols of b.p. above 160 DEG C. and tetrahydronaphthalene at 180-200 DEG C. for 30-60 minutes. The preferred proportions of reactants are chosen so that there are 1 to 1.5 1 DEG and/or 2 DEG amigo groups for each carboxyl group or when using an unsaturated acid 1 to 1.5 1 DEG and/or 2 DEG amino groups for each carboxyl group and each reactive double bond. When using a ,b -unsaturated carboxylic acids small amounts of polymerization inhibitors such as hydroquinone and methylene blue may be added. The condensation of amines with acid halides may be carried out at room temperature in the presence of a proton acceptor such as pyridine or a 3 DEG aliphatic amine. The polyamides so formed have mean molecular weights of 600 to 1500. Examples of the preparation of a number of compounds using some of the above-named reactants are given.ALSO:Levelling agents for use in dyeing natural or regenerated cellulose or wool with vat or sulphur dyestuffs comprise water-soluble polyamides derived from (a) an aliphatic, cycloaliphatic or aromatic polyamine or a heterocyclic compound containing at least two acylatable nitrogen atoms and (b) an a ,b -unsaturated carboxylic acid or an aliphatic carboxylic acid which may contain one or more hetero atoms or a functional derivative of these which is capable of amide formation (see Groups IV(a) and IV(b)). The levelling agents are soluble in alkaline medium and may be applied at a concentration of 0,2-1,0 g./l. during or subsequently to dyeing. Shading, i.e. adding further small amounts of dye to the hot vat during dyeing, may be effectively accomplished. Also present in the dye-bath may be conventional dispersing agents and protective colloids. Examples are given of the dyeing of viscose staple yarn, cotton yarn and cotton knitted and woven fabrics.

    Improvements in the production of ethinyl ionol
    29.
    发明专利
    Improvements in the production of ethinyl ionol 未知

    公开(公告)号：GB852945A

    公开(公告)日：1960-11-02

    申请号：GB556459

    申请日：1959-02-18

    Applicant: BASF AG

    Inventor： PASEDACH HEINRICH ,  SEEFELDER MATTHIAS

    Abstract: A process for the production of ethinyl ionol comprises reacting ionone with acetylene in the presence of monosodium acetylide in a solvent which dissolves in each part by volume at least 10 parts by volume of acetylene. Normal and elevated pressures may be employed. Solvents specified include tetrahydrofurane, dioxane, dimethylformal, diethyl formal, dimethyl and dibutyl acetals of acetaldehyde glycol dimethyl, diethyl and methyl ethyl ethers, ethers of diglycols and higher polyglycols, dimethyl-formamide, N-methylpyrrolidone, N.N-dimethyl urethane, N-methyl pyrrolidine and N-methylmorpholine. Auxiliary solvents such as diethyl ether, benzene and toluene may also be employed. The catalyst may be formed under the reaction conditions e.g. from sodium, sodamide, sodium hydride, disodium acetylide or organometallic sodium compounds such as phenyl sodium and the sodium derivative of naphthalene. Examples relating to the production of ethinyl b -ionol are furnished and the corresponding ethinyl a -ionol is stated to be prepared by analogous processes.

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