首页> 外国专利> 4 - (2H - naphtho bracket on 1,2 - d bracket to triazole - 2 - y) - 2 - stilbencarbonsaeureester and their use as brighteners

4 - (2H - naphtho bracket on 1,2 - d bracket to triazole - 2 - y) - 2 - stilbencarbonsaeureester and their use as brighteners

机译:4-(2H-萘括号在1,2-d括号中的三唑-2-y)-2-stilbencarbonsaeureester及其用作增白剂

摘要

The invention comprises fluorescent naphthotriazoles of the formula: FORM:0944265/C2/1 wherein R1 and R2 represent hydrogen, halogen such as fluorine, chlorine and bromine, C1-4 alkyl, C1-6 alkoxy or cycloalkoxy, and R3 represents alkyl, monohydroxyalkyl, dihydroxyalkyl, trihydroxyalkyl, dialkylaminoalkyl, aryl (optionally substituted by chlorine, bromine, fluorine, alkyl or alkoxy), hexamethyleneiminoN-ethyl or morpholino-N-alkyl or piperidino-N-alkyl in which the alkyl group contains from 1 to 4 carbon atoms. The naphthotriazoles may be prepared by diazotizing a stilbene of the formula: FORM:0944265/C2/2 coupling the product with 2-naphthylamine, oxidizing the resulting monazo dye to a triazole, converting the free carboxylic group to an acid chloride group by treatment with thionyl chloride and finally reacting the acid chloride group with an appropriate phenol, dialkylamino-alkanol, heterocyclic-substituted alkanol or mono-, di-, tri-, or tetra-hydric alcohol. Alternatively, compounds of the formula: FORM:0944265/C2/3 may be formed from the free carboxylic acid via the acid chloride, the nitro group in the resulting ester reduced to an amino group, the resulting compound diazotized, coupled with 2-naphthylamine and finally oxidized to the required triazole.ALSO:Polyethylene terephthalate is brightened by adding to the starting mixture of dimethyl terephthalate and ethylene glycol, or to a low polymer obtained therefrom, a fluorescent naphthotriazole of the formula: FORM:0944265/C3/1 wherein R1 and R2 represent hydrogen, halogen such as fluorine, chlorine and bromine, C1-4 alkyl, C1-6 alkoxy or cycloalkoxy, and R3 represents alkyl, monohydroxyalkyl, dihydroxyalkyl, trihydroxyalkyl, dialkylaminoalkyl, aryl (optionally substituted by chlorine, bromine, fluorine, alkyl or alkoxy), hexamethyleneimino-N-ethyl or morpholino-N-alkyl or piperidino-N-alkyl in which the alkyl group contains from 1 to 4 carbon atoms.ALSO:Monazo dyestuffs are prepared by diazotizing a stilbene of the formula FORM:0944265/C3/1 wherein R1 and R2 represent hydrogen, halogen such as fluorine, chlorine and bromine, C1-4 alkyl, C1-6 alkoxy or cycloalkoxy, and coupling the product with 2-naphthylamine. Alternatively, further monazo dyestuffs are formed by reducing the nitro group in compounds of the formula FORM:0944265/C3/2 wherein R3 represents alkyl, monohydroxyalkyl, dihydroxyalkyl, trihydroxyalkyl, dialkylaminoalkyl, aryl (optionally substituted by chlorine, bromine, fluorine, alkyl or alkoxy), hexamethyleneimino - N - ethyl or morpholinoN-alkyl or piperidino - N - alkyl in which the alkyl group contains from 1 to 4 carbon atoms, diazotizing the resulting amino compound and coupling it with 2-naphthylamine.ALSO:Nylon, polyethylene teraphthalate and polyacrylonitrile in the form of films, fibres and fabrics are brightened by treatment with a fluorescent naphthotriazole of the formula:- FORM:0944265/D1-D2/1 wherein R1 and R2 represent hydrogen, halogen such as fluorine, chlorine and bromine, C1-4 alkyl, C1-6 alkoxy or cycloalkoxy, and R3 represents alkyl, monohydroxyalkyl, dihydroxyalkyl, trihydroxyalkyl, dialkylaminoalkyl, aryl (optionally substituted by chlorine, bromine, fluorine, alkyl or alkoxy), hexamethyleneimino-N-ethyl or morpholino-N-alkyl or piperidino-N-alkyl in which the alkyl group contains from 1 to 4 carbon atoms. The fluorescent naphthotriazoles may be applied to the materials to be brightened from a dimethylformamide solution to which has been added a small amount of an aqueous polyoxyethylene surfactant.
机译:本发明包括下式的荧光萘三唑:其中R 1和R 2代表氢,卤素如氟,氯和溴,C 1-4烷基,C 1-6烷氧基或环烷氧基,并且R 3代表烷基。 ,单羟烷基,二羟烷基,三羟烷基,二烷基氨基烷基,芳基(可选地被氯,溴,氟,烷基或烷氧基取代),六亚甲基亚氨基N-乙基或吗啉代-N-烷基或哌啶子基-N-烷基,其中烷基包含1至4碳原子。萘并三唑可以通过将式:的二苯乙烯重氮化而制得,该产物与2-萘胺偶合,将所得的单偶氮染料氧化为三唑,将游离的羧基转化为酰氯。用亚硫酰氯处理,最后使酰氯基团与适当的苯酚,二烷基氨基-链烷醇,杂环取代的链烷醇或一,二,三或四羟基醇反应。或者,可以由游离羧酸经由酰氯形成式:的化合物,将所得酯中的硝基还原为氨基,将所得的化合物重氮化,再与2偶联。 -萘胺,最后氧化成所需的三唑。ALSO:聚对苯二甲酸乙二酯通过向对苯二甲酸二甲酯和乙二醇的起始混合物中或从中得到的低聚物中加入下式的荧光萘三唑而增亮:,其中R 1和R 2代表氢,卤素,例如氟,氯和溴,C 1-4烷基,C 1-6烷氧基或环烷氧基,并且R 3代表烷基,单羟基烷基,二羟基烷基,三羟基烷基,二烷基氨基烷基,芳基(可选地被氯取代) ,溴,氟,烷基或烷氧基),六亚甲基亚氨基-N-乙基或吗啉代-N-烷基或哌啶子基-N-烷基,其中烷基包含1-4个碳原子。制备ALSO:单偶氮染料d。通过将式的二苯乙烯重氮化,其中R1和R2代表氢,卤素如氟,氯和溴,C1-4烷基,C1-6烷氧基或环烷氧基,并将产物与2-萘胺。备选地,通过还原式的化合物中的硝基来形成其他的偶氮染料,其中R3代表烷基,单羟基烷基,二羟基烷基,三羟基烷基,二烷基氨基烷基,芳基(任选地被氯,溴,氟,烷基或烷氧基),六亚甲基亚氨基-N-乙基或吗啉代N-烷基或哌啶子基-N-烷基,其中烷基含1-4个碳原子,将重氮化的氨基化合物重氮化并将其与2-萘胺偶联.ALSO:尼龙,薄膜,纤维和织物形式的聚对苯二甲酸乙二醇酯和聚丙烯腈可通过以下通式的荧光萘三唑处理来增亮:-其中R1和R2代表氢,卤素,例如氟,氯和溴,C 1-4烷基,C 1-6烷氧基或环烷氧基,且R 3表示烷基,单羟基烷基,二羟基烷基,三羟基烷基,二烷基氨基烷基,芳基(可选地被氯,溴,f氟,烷基或烷氧基),六亚甲基亚氨基-N-乙基或吗啉代-N-烷基或哌啶子基-N-烷基,其中烷基包含1-4个碳原子。可以将荧光萘三唑从已添加了少量水性聚氧乙烯表面活性剂的二甲基甲酰胺溶液施用于待增亮的材料。

著录项

  • 公开/公告号DE1419334B2

    专利类型

  • 公开/公告日1973-03-08

    原文格式PDF

  • 申请/专利权人

    申请/专利号DE19621419334

  • 发明设计人

    申请日1962-03-30

  • 分类号C07D55/04;

  • 国家 DE

  • 入库时间 2022-08-23 07:14:38

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