Method for the production of perylen-3,4:9,10-tetracarboxylic acid diimides and perylen-3,4:9,10-tetracarboxylic acid dianhydride and naphtalene-1,8-dicarboxylimides

    公开(公告)号:US20050131220A1

    公开(公告)日:2005-06-16

    申请号:US10510579

    申请日:2003-04-15

    CPC分类号: C09B5/62 C09B57/08

    摘要: A process for preparing perylene-3,4:9,10-tetracarboxylic diimides of the general formula I where R is C1-C30-alkyl whose carbon chain may be interrupted by one or more —O— moieties and/or which may be substituted by one or more substituents selected from the group consisting of C5-C8-cycloalkyl (which may be substituted by one or more C1-C6-alkyl substituents), phenyl or phenyl-C1-C6-alkyl (which may each be substituted by one or more C1-C18-alkyl and/or C1-C6-alkoxy substituents), —OCOR1, —N(R1)2, —SO2NH2, —SO2N(R1)2, —CON(R1)2 and —COOR1; C5-C8-cycloalkyl whose carbon skeleton may be interrupted by one or more moieties selected from the group consisting of —O—, —S— and —NR2- and/or which may be substituted by one or more C1-C6-alkyl substituents; phenyl, phenyl-C1-C6-alkyl, naphthyl or hetaryl, which may each be substituted by one or more substituents selected from the group consisting of C1-C18-alkyl, C1-C6-alkoxy, phenylazo, naphthylazo, pyridylazo, pyrimidylazo, cyano, —N(R1)2, —CON(R1)2 and —COOR1; R1 is C1-C6-alkyl, C5-C8-cycloalkyl, phenyl or phenyl-C1-C6-alkyl; R2 is C1-C6-alkyl, phenyl or phenyl-C1-C6-alkyl, by dimerizing a naphthalene-1,8-dicarboximide of the formula II comprises effecting said dimerizing in a reaction medium consisting essentially of an a polar aprotic organic solvent and an alkali metal base and subsequently reoxidizing the resulting alkali metal salt of the leuco form of the perylene-3,4:9,10-tetracarboxylic diimide in the presence of a polar solvent, and also preparation of perylene-3,4:9,10-tetracarboxylic dianhydride and naphthalene-1,8-dicarboximides.

    PREPARATION OF PERYLEN-3,4:9,10-TETRACARBOXYLIC DIANHYDRIDE AND ALSO OF NAPHTALENE-1,8-DICARBOXIMIDES
    2.
    发明申请
    PREPARATION OF PERYLEN-3,4:9,10-TETRACARBOXYLIC DIANHYDRIDE AND ALSO OF NAPHTALENE-1,8-DICARBOXIMIDES 有权
    季戊四醇3,4:9,10-四羧酸二乙酰胺的制备以及壬二酮-1,8-二氧杂环己酮的制备

    公开(公告)号:US20080161569A1

    公开(公告)日:2008-07-03

    申请号:US11955605

    申请日:2007-12-13

    IPC分类号: C07D471/00 C07D221/14

    CPC分类号: C09B5/62 C09B57/08

    摘要: A process for preparing perylene-3,4:9,10-tetracarboxylic dianhydride, comprising: dimerizing a naphthalene-1,8-dicarboximide of the formula IIa; reoxidizing the resulting alkali metal salt of the leuco form of the perylene-3,4:9,10-tetracarboxylic diimide of the formula Ia; hydrolyzing the diimide to the tetraalkali metal salt of perylene-3,4:9,10-tetracarboxylic acid in the presence of an inert organic solvent, of an alkali metal base and of water; and subjecting the tetraalkali metal salt of perylene-3,4:9,10-tetracarboxylic acid to the action of an aqueous inorganic acid to convert it into perylene-3,4:9,10-tetracarboxylic dianhydride; wherein R3 is cyclohexyl or phenyl which may each be substituted by up to three C1-C4-alkyl radicals, and the dimerizing is in a substantially homogeneous reaction medium consisting essentially of an apolar aprotic organic solvent and an alkali metal base.

    摘要翻译: 一种制备苝-3,4:9,10-四羧酸二酐的方法,包括:使式IIa的萘-1,8-二甲酰亚胺二聚化; 重新氧化得到的无水形式的式Ia的苝-3,4:9,10-四羧酸二酰亚胺的碱金属盐; 在惰性有机溶剂,碱金属碱和水的存在下将二酰亚胺水解成苝-3,4:9,10-四羧酸的四碱金属盐; 并将苝-3,4:9,10-四羧酸的四碱金属盐作为无机酸水溶液的作用,将其转化成苝-3,4:9,10-四羧酸二酐; 其中R 3是可以被至多三个C 1 -C 4 - 烷基取代的环己基或苯基,二聚是 在基本均匀的反应介质中,基本上由非极性非质子有机溶剂和碱金属碱组成。

    Preparation of perylen-3,4:9,10-tetracarboxylic dianhydride and also of naphtalene-1,8-dicarboximides
    3.
    发明授权
    Preparation of perylen-3,4:9,10-tetracarboxylic dianhydride and also of naphtalene-1,8-dicarboximides 有权
    苝-3,4:9,10-四羧酸二酐以及萘-1,8-二羧酰亚胺的制备

    公开(公告)号:US07807836B2

    公开(公告)日:2010-10-05

    申请号:US11955605

    申请日:2007-12-13

    IPC分类号: C07D471/16 C07D471/00

    CPC分类号: C09B5/62 C09B57/08

    摘要: A process for preparing perylene-3,4:9,10-tetracarboxylic dianhydride, comprising: dimerizing a naphthalene-1,8-dicarboximide of the formula IIa; reoxidizing the resulting alkali metal salt of the leuco form of the perylene-3,4:9,10-tetracarboxylic diimide of the formula Ia; hydrolyzing the diimide to the tetraalkali metal salt of perylene-3,4:9,10-tetracarboxylic acid in the presence of an inert organic solvent, of an alkali metal base and of water; and subjecting the tetraalkali metal salt of perylene-3,4:9,10-tetracarboxylic acid to the action of an aqueous inorganic acid to convert it into perylene-3,4:9,10-tetracarboxylic dianhydride; wherein R3 is cyclohexyl or phenyl which may each be substituted by up to three C1-C4-alkyl radicals, and the dimerizing is in a substantially homogeneous reaction medium consisting essentially of an apolar aprotic organic solvent and an alkali metal base.

    摘要翻译: 一种制备苝-3,4:9,10-四羧酸二酐的方法,包括:使式IIa的萘-1,8-二甲酰亚胺二聚化; 重新氧化得到的无水形式的式Ia的苝-3,4:9,10-四羧酸二酰亚胺的碱金属盐; 在惰性有机溶剂,碱金属碱和水的存在下将二酰亚胺水解成苝-3,4:9,10-四羧酸的四碱金属盐; 并将苝-3,4:9,10-四羧酸的四碱金属盐作为无机酸水溶液的作用,将其转化成苝-3,4:9,10-四羧酸二酐; 其中R 3是可以被至多三个C 1 -C 4 - 烷基取代的环己基或苯基,二聚在基本上均匀的反应介质中,其基本上由非极性非质子有机溶剂和碱金属碱组成。

    Process for producing perylene-3, 4-dicarboxylic acid imides
    5.
    发明授权
    Process for producing perylene-3, 4-dicarboxylic acid imides 有权
    生产苝-3,4-二羧酸酰亚胺的方法

    公开(公告)号:US6136976A

    公开(公告)日:2000-10-24

    申请号:US147353

    申请日:1998-12-07

    CPC分类号: C09B5/62 C07D221/18

    摘要: Perylene-3,4-dicarboximides I ##STR1## (R.sup.1 is hydrogen; C.sub.1 -C.sub.8 -alkyl; C.sub.5 -C.sub.8 -cycloalkyl; substituted or unsubstituted phenyl or naphthyl;R.sup.2 independently at each occurrence is hydrogen; C.sub.1 -C.sub.18 -alkyl, substituted or unsubstituted aryloxy, arylthio, hetaryloxy or hetarylthio)are prepared by reacting the corresponding perylene-3,4,9,10-tetracarboxylic acid or its anhydride (II) with an amide IIIR.sup.3 --CO--NHR.sup.1 III(R.sup.3 : C.sub.1 -C.sub.4 -alkyl or --NR.sup.4 R.sup.5 where R.sup.4 and R.sup.5 independently are hydrogen or one of the R.sup.1 alkyls, cycloalkyls, phenyls or naphthyls and where if two or more of R.sup.1, R.sup.4 and R.sup.5 are other than hydrogen they are identical)under superatmospheric pressure in the presence of an inert diluent and a transition metal catalyst.

    摘要翻译: PCT No.PCT / EP97 / 02761 Sec。 371 1998年12月7日第 102(e)日期1998年12月7日PCT提交1997年5月28日PCT公布。 公开号WO97 / 46533 日期1997年12月11日亚苯基-3,4-二甲酰亚胺I(R1为氢; C1-C8-烷基; C5-C8-环烷基;取代或未取代的苯基或萘基; R2各自独立地为氢; C1-C18-烷基 ,取代或未取代的芳氧基,芳硫基,杂芳氧基或杂芳硫基)通过相应的苝-3,4,9,10-四羧酸或其酸酐(II)与酰胺IIIR3-CO-NHR1 III(R3:C1- C4烷基或-NR4R5,其中R4和R5独立地是氢或R1烷基,环烷基,苯基或萘基中的一个,并且如果R 1,R 4和R 5中的两个或多个不是氢,则它们相同)在超大气压下 存在惰性稀释剂和过渡金属催化剂。

    N,N'-dimethylperylene-3,4,9,10-tetracarboxylic acid diimide pigments
suitable for water-based paints
    6.
    发明授权
    N,N'-dimethylperylene-3,4,9,10-tetracarboxylic acid diimide pigments suitable for water-based paints 失效
    适用于水性涂料的N,N'-二甲基亚丙基-3,4,9,10-四羧酸二酰亚胺颜料

    公开(公告)号:US6099636A

    公开(公告)日:2000-08-08

    申请号:US101444

    申请日:1998-07-16

    摘要: A N,N'-dimethylperylene-3,4,9,10-tetracarboxylic diimide pigment suitable for aqueous basecoats is obtainable by coating the diimide, suspended in an aqueous medium, with a carboxyl-carrying resin in the presence of 3,4-dicarboximidoperylene-9-sulfonic acid or salts thereof and with a C.sub.8 -C.sub.8 -alkyl- or-alkenylamine, isolating and drying the coated dimide and then subjecting it to dry milling.

    摘要翻译: PCT No.PCT / EP97 / 00064 Sec。 371日期:1998年7月16日 102(e)1998年7月16日PCT 1997年1月9日PCT PCT。 公开号WO97 / 26301 日期1997年7月24日适用于底漆水溶液的N,N'-二甲基亚丙基-3,4,9,10-四羧酸二酰亚胺颜料可通过在存在下将羧基载体树脂悬浮于含水介质中的二酰亚胺 的3,4-二羧基亚苯基-9-磺酸或其盐和C8-C8-烷基 - 或 - 链烯基胺,分离并干燥涂覆的二聚体,然后将其进行干研磨。

    Sulfonated monoazo colorant lake obtained by di-azo coupling of
5-acetylamino-2-aminobenzene-1-sulfonic acid with
1-(3'-sulfophenyl)-3-methylphyrazol-5-one
    9.
    发明授权
    Sulfonated monoazo colorant lake obtained by di-azo coupling of 5-acetylamino-2-aminobenzene-1-sulfonic acid with 1-(3'-sulfophenyl)-3-methylphyrazol-5-one 失效
    通过5-乙酰氨基-2-氨基苯-1-磺酸与1-(3'-磺基苯基)-3-甲基吡唑-5-酮的偶氮偶合获得的磺化单偶氮染料色淀

    公开(公告)号:US4594411A

    公开(公告)日:1986-06-10

    申请号:US617155

    申请日:1984-06-06

    申请人: Georg Henning

    发明人: Georg Henning

    摘要: This invention relates to a method of dyeing thermoplastics with sulfonated monoazo colorant lakes having a sulfophenyl pyrazole substituent, of general formula ##STR1## wherein R is CH.sub.3 or COO.sup.- ; X is Cl, CH.sub.3, CH.sub.3 O, C.sub.2 H.sub.5 O, C.sub.2 H.sub.5 CONH, NH.sub.2 CONH, C.sub.6 H.sub.5 CONH, CH.sub.3 SO.sub.2 NH, C.sub.6 H.sub.5 SO.sub.2 NH, CH.sub.3 CONH, or hydrogen; Y is hydrogen, Cl, or CH.sub.3 ; Z is hydrogen or Cl, n is 0, 1 or 2; and Me.sup.+ is one equivalent of a cation selected from the group consisting of NH.sub.4.sup.+, Li.sup.+, K.sup.+, Na.sup.+, 1/2Sr.sup.2+, 1/2Mn.sup.2+, 1/2Ni.sup.2+, 1/2Ba.sup.2+, 1/2Mg.sup.2+ and 1/2Ca.sup.2+ ; with the proviso that if R is COO.sup.-, the additional equivalent charge is compensated by a further equivalent of said or another cation. These compounds, which are insoluble in organic solvents and sparingly soluble in water, are useful as lakes with good pigmentary characteristics and possessing very good lightfastness in plastics, such as polyolefins, polyvinyl chloride, polystyrene, and ABS. They are also useful in surface coatings, and particularly suitable for coloring thermoplastics. Noteworthy is their good plasticizer fastness, their high stability to heat and the absence of blooming they produce when used.

    摘要翻译: 本发明涉及一种通过具有通式(I)的磺酰基苯基吡唑取代基的磺化单偶氮染料盐染色热塑性塑料的方法,其中R是CH 3或COO-; X是Cl,CH 3,CH 3 O,C 2 H 5 O,C 2 H 5 CONH,NH 2 CONH,C 6 H 5 CONH,CH 3 SO 2 NH,C 6 H 5 SO 2 NH,CH 3 CONH或氢; Y是氢,Cl或CH 3; Z是氢或Cl,n是0,1或2; 和Me +是选自NH4 +,Li +,K +,Na +,1 / 2Sr2 +,1 / 2Mn2 +,1 / 2Ni2 +,1 / 2Ba2 +,1 / 2Mg2 +和1 / 2Ca2 +的阳离子的1当量。 条件是如果R是COO-,则额外的等效电荷由另外的等价的所述阳离子补偿。 这些不溶于有机溶剂并微溶于水的化合物可用作具有良好颜料特征的湖泊,并且在塑料如聚烯烃,聚氯乙烯,聚苯乙烯和ABS中具有非常好的耐光性。 它们也可用于表面涂层,特别适用于着色热塑性塑料。 值得注意的是它们具有良好的增塑剂坚牢度,它们对热的高稳定性和使用时不产生起霜。