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    • 22. 发明授权
    • Anthraquinone compounds and process for preparing same
    • 蒽醌化合物及其制备方法
    • US4098793A
    • 1978-07-04
    • US836087
    • 1977-09-23
    • Giuseppe RibaldoneRenato GrecuCamillo PaffoniGiuseppe Sironi
    • Giuseppe RibaldoneRenato GrecuCamillo PaffoniGiuseppe Sironi
    • C09B1/44C09B1/516C09B1/54D06P1/24C07D285/10
    • D06P1/24C09B1/44C09B1/516C09B1/542
    • The present invention relates to a new class of compounds belonging to the anthraquinone series, having the general formula: ##STR1## wherein R, R', R", R'", R' are indifferently H or Chlorine, ##STR2## Such compounds exhibit a color varying from yellow to violet depending on the nature and position of substituents R, R', R", R'", R'.sup.v and, in virtue of their excellent stability characteristics, they are particularly useful as pigments and vat dyes.This invention relates furthermore to the preparation of compounds having general formula (I) and to the utilization thereof, particularly in the following applications:Pigmentation of plastic materials, such as polyvinyl chloride, polystyrene, polyolefins, polymethylmethacrylate, polycarbonates and ABS copolymers (acrylonitrile-butadiene-styrene);Pigmentation of varnishes, stoving enamels, inks and pastes for the printing of textiles;Vat dyeing of cellulose fibres such as cotton, flax, rayon.BACKGROUND OF THE INVENTIONAs far as it is known, the anthraquinone derivatives of 1,2,5-thiadiazole-3,4-dicarboxylic acid of formula (I), which are the object of the present invention, are not described in the Art.The prior Art, however not directly pertinent, generically describes dyestuffs of the anthraquinone series deriving from dicarboxylic acids, for example benzenic, pyridinic, aliphatic acids etc.OBJECTS OF THE INVENTIONIt is an object of this invention to provide a new class of anthraquinone compounds of general formula (I), having useful applications in the field of the pigments and of the vat dyes. Another object is to provide a process for preparing same.GENERAL DESCRIPTION OF THE INVENTIONThese and still other objects, that will more clearly appear to those skilled in the Art from the following description, are achieved by compounds having general formula (I), prepared by means of a process characterized in that the dichloride of 1,2,5-thiadiazole-3,4-dicarboxylic acid (II) is reacted with 1-aminoanthraquinone or substituted derivatives (III) thereof according to a substantially stoichiometric molar ratio, in the presence of an inert solvent, at a temperature ranging from 100.degree. to about 170.degree. C.The reaction can be schematically represented by the following equation (1): ##STR3## wherein R', R", R'", R'.sup.v have the meaning already specified; HCl forms and liberates as a gas from the reacting mixture. It is not necessary, therefore, to employ basic substances to neutralize hydrochloric acid. As mentioned hereinbefore, the reaction is conducted in an inert solvent and at a temperature comprised between 100.degree. and about 170.degree. C, preferably between 120.degree. and about 150.degree. C.1-aminoanthraquinones (III) employable in the present invention are in particular:1-aminoanthraquinone, 1-amino-4-hydroxyanthraquinone, 1-amino-4-benzamidoanthraquinone, 1-amino-5-benzamidoanthraquinone, 1-amino-4-(p-acetamidoanilino)-anthraquinone, 1-amino-4-(p-toluidino)-anthraquinone, 1-amino-5-methoxyanthraquinone, 1-amino-2-phenoxy-4-hydroxyanthraquinone, 1-amino-2,4-dibromoanthraquinone, 1-amino-2-bromo-4-hydroxyanthraquinone, 1-amino-6,7-dichloroanthraquinone etc.As inert solvent it is possible to use chlorobenzene, the various dichlorobenzenes and trichlorobenzenes, and nitrobenzenes.The time required for the reaction varies from 2 to 8 hours, depending on the reaction temperature and on the type of 1-aminoanthraquinones utilized. The molar ratio is practically stoichiometric, that is: 2 moles of anthraquinone compound (III) for 1 mole of dichloride (II).The raw materials necessary for the process according to this invention are easily available, as 1-aminoanthraquinone and the substituted derivatives (III) thereof are commercial products usually employed as intermediates for dyestuffs and pigments.As to the dichloride of 1,2,5-thiadiazole-3,4-dicarboxylic acid (II), such product is known since long and is obtained, according to known techniques, by chlorination with SOCl.sub.2 of the monopotassium salt of 1,2,5-thiadiazole-3,4-dicarboxylic acid, that is, in its turn, a known compound.According to an effective embodiment, the present invention is conducted by operating in practice as follows: the dichloride of 1,2,5-thiadiazole-3,4-dicarboxylic acid (II) and the 1-aminoanthraquinone or its substituted derivatives (III) are heated, after mixing in the inert solvent, to 100.degree.-170.degree. C, preferably to 120.degree.-150.degree. C, until the anthraquinone compound (III) has thoroughly disappeared.The thin layer chromatography is useful for this check.At the end of the reaction the reaction mixture is filtered, preferably in hot conditions, and the pigment cake is then washed with the reaction solvent and successively with methanol until the washings result colourless.The pigments obtained according to this invention are substances exhibiting a colour varying from yellow to violet and characterized by a high insolubility in the common organic solvents and by a high melting point, generally higher than 300.degree. C.To impart the particular desired applicative characteristics to the products so obtained it is impossible to utilize the grinding, for example in a ball mill, or the precipitation from sulphuric acid and in general the techniques already known.Also for the dyeing of plastic materials, of varnishing products and for the vat dyeing the pigments of the present invention are consistent with the conventional techniques.Due to the simple preparation conditions and applicative characteristics of the obtained pigments, the present invention appears particularly advantageous.Preparation and application of the present invention will be now described more in detail in the following examples, which are given, however, by way of example only.
    • 本发明涉及一类属于蒽醌系列的化合物,具有以下通式:其中R,R',R“,R”',R'为无差异的H或氯,
    • 27. 发明授权
    • Organic dyes containing silane groups and process for preparing same
    • 含有硅烷基团的有机染料及其制备方法
    • US4609404A
    • 1986-09-02
    • US524083
    • 1983-08-17
    • Antonio MarracciniFilippo M. CarliniAntonio PasqualeGiorgio Maranzana
    • Antonio MarracciniFilippo M. CarliniAntonio PasqualeGiorgio Maranzana
    • C09B1/467C09B1/516C09B1/54C09B1/58C09B69/00C09C1/28C09C1/36
    • C09B69/008C09B1/467C09B1/516C09B1/547C09B1/585
    • This invention relates to organic dyes containing silane groups; composite pigments obtainable by grafting said dyes onto an inorganic substrate; and, the respective processes for preparing said dyes and composite pigments.The dyes have general formula: ##STR1## wherein R.sub.1 and R.sub.2, which may be equal or different, are selected from the group consisting of H, --NH.sub.2, --NHR wherein R is an alkyl group having from 1 to 4 carbon atoms or a phenyl group, --NHCOCH.sub.3, --NHCOC.sub.6 H.sub.5, --NO.sub.2, a halogen, --OH, --O--C.sub.6 H.sub.5 and --S--C.sub.6 H.sub.5 ; n is a number selected from 3, 4 and 5; W is selected from the group consisting of an alkyl group having from 1 to 4 carbon atoms and a phenyl group; Y is an alkoxy group having from 1 to 4 carbon atoms; q is a number selected from 0 and 1; X is 3 and m is a number selected from 0, 1, 2 and 3 when q is 0; x is 2 and m is a number selected from 0, 1 and 2 when q is 1. The composite pigments obtained from said dyes are employed in the painting products, air enamels and stoving enamels, in the pigmentation of plastic materials, in the inks and in the printing of fabrics.
    • 本发明涉及含有硅烷基团的有机染料; 通过将所述染料接枝到无机基材上可获得的复合颜料; 以及制备所述染料和复合颜料的各个方法。 染料具有以下通式:其中R 1和R 2可以相同或不同,选自H,-NH 2,-NHR,其中R是具有1至4个碳原子的烷基 原子或苯基,-NHCOCH 3,-NHCOC 6 H 5,-NO 2,卤素,-OH,-O-C 6 H 5和-S-C 6 H 5; n是选自3,4和5的数字; W选自具有1至4个碳原子的烷基和苯基; Y是具有1至4个碳原子的烷氧基; q是选自0和1的数字; 当q为0时,X为3,m为选自0,1,2和3的数; x为2,当q为1时,m为选自0,1和2的数字。由所述染料得到的复合颜料用于油墨,空气搪瓷和烘烤搪瓷,在油墨着色中,在油墨中 和织物的印花。