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    • 4. 发明授权
    • Mixed crystals of benzimidazolonedioxazine compounds
    • 苯并咪唑啉二恶嗪化合物的混合晶体
    • US06762299B2
    • 2004-07-13
    • US10001777
    • 2001-10-24
    • Martin U. SchmidtPeter KempterCarsten PluegRoland Born
    • Martin U. SchmidtPeter KempterCarsten PluegRoland Born
    • C07D49822
    • C09B19/02C09B67/0034
    • A mixed crystal of two or more different benzimidazolonedioxazine compounds of the formula (1) where X and X′ are identical or different and are hydrogen or halogen, R1, R1′, R2 and R2′ are identical or different and are hydrogen, C1-C18 alkyl, trifluoromethyl, C1-C18 alkylcarbonyl, C5-C6 cycloalkyl or phenyl which may be unsubstituted or substituted by one or more halogen atoms, nitro groups, trifluoromethyl, C1-C18 alkyl, C1-C18 alkoxy, C1-C18 alkylcarbonyl and/or C1-C18 alkoxycarbonyl groups. The mixed crystals are of low solubility and feature good fastness properties and red to blue colorations. The mixed crystals are suitable for pigmenting paints, plastics, printing inks, aqueous or solvent-based pigment preparations, electrophotographic toners and developers, powder coating materials, inks, preferably inkjet inks, color filters, and for coloring seed and cosmetics.
    • 其中X和X'相同或不同,为氢或卤素,R1,R1',R2和R2'的两种或更多种不同的式(1)苯并咪唑并二恶嗪化合物的混合晶体是相同或不同的,为氢,C1-C18 烷基,三氟甲基,C 1 -C 18烷基羰基,C 5 -C 6环烷基或苯基,其可以是未取代的或被一个或多个卤素原子,硝基,三氟甲基,C 1 -C 18烷基,C 1 -C 18烷氧基,C 1 -C 18烷基羰基和/ C1-C18烷氧基羰基。混晶具有低溶解度,具有良好的牢度和红至蓝色。混晶适用于着色涂料,塑料,印刷油墨,水性或溶剂型颜料制剂,电子照相色调剂和显影剂 ,粉末涂料,油墨,优选喷墨油墨,滤色器,以及用于着色种子和化妆品。
    • 5. 发明授权
    • Triphendioxazine compounds
    • 三苯并二恶嗪化合物
    • US5565563A
    • 1996-10-15
    • US349114
    • 1994-12-02
    • Bansi L. KaulPeter Kempter
    • Bansi L. KaulPeter Kempter
    • C07D498/04C07D498/22C08K5/357C09B19/02C09B69/10C07D498/14
    • C09B19/02
    • Triphendioxazine compounds of formula I, ##STR1## in which R.sub.1 and R.sub.2 are either both hydrogen or form a single chain linking the 8,9-; 9,10- or 10,11-positions, the single chain having the formula --NR.sub.5 ---(CO).sub.m --NH--, --CR.sub.5 .dbd.CH--CO--NH--, --CO--CH.sub.2 --CO--NH--, --CO--CH.dbd.CR.sub.5 --NH--, --CO--NH--CO--NH--, --CO--NH--CR.sub.6 .dbd.N--, --CR.sub.6 .dbd.N--CO--NH--, --NR.sub.5--(CO).sub.m --O--or --NH--CR.sub.5 .dbd.N--whereR.sub.5 is hydrogen, C.sub.1-4 alkyl or phenyl, R.sub.6 is hydrogen, C.sub.1-4 alkyl or phenyl;m is 1 or 2 and R.sub.3 and R.sub.4 are either both hydrogen or form a single chain linking the 1,2-, 2,3- or 3,4-positions, the single chain having a formula selected from --NR.sub.5 --(CO).sub.m --NH--, --CR.sub.5 .dbd.CH--CO--NH--, --O--CH.sub.2 --CO--NH--, --CO--CH.dbd.CR.sub.5 --NH--, --CO--NH--CO--NH--, --CONH--CR.sub.6 .dbd.N--, --CR.sub.6 .dbd.N--CO--NH--, --NR.sub.5 --(CO).sub.m --O--or --NH--CR.sub.5 .dbd.N--where the symbols R.sub.5, R.sub.6 and m are defined above andwhen R.sub.3 and R.sub.4 are in the 1,2-position and R.sub.7 is located in the 3-position orwhen R.sub.3 and R.sub.4 are in the 3,4-position and R.sub.7 is located in the 2-position orwhen R.sub.1 and R.sub.2 are in the 8,9-position and R.sub.7 is located in the 10-position orwhen R.sub.1 and R.sub.2 are in the 10,11-position and R.sub.7 is in the 9-positionthen R.sub.7 is hydrogen or C.sub.1-2 alkoxy, otherwise R.sub.7 is hydrogen, with the proviso that if R.sub.1 and R.sub.2 are hydrogen then R.sub.3 and R.sub.4 cannot be hydrogen.These compounds are useful as pigments.
    • 式I的三苯并二恶嗪化合物,其中R 1和R 2都是氢或形成连接8,9-的单链; 9,10-或10,11-位,具有式-NR 5 - (CO)m -NH-,-CR 5 = CH-CO-NH-,-CO-CH 2 -CO-NH-, - CO-CH = CR5-NH-,-CO-NH-CO-NH-,-CO-NH-CR6 = N-,-CR6 = N-CO-NH-,-NR5-(CO)mO-或-NH -CR5 = N-,其中R5是氢,C1-4烷基或苯基,R6是氢,C1-4烷基或苯基; m为1或2,且R 3和R 4均为氢或形成连接1,2-,2,3-或3,4-位的单链,具有选自-NR 5 - (CO) m-NH-,-CR5 = CH-CO-NH-,-O-CH2-CO-NH-,-CO-CH = CR5-NH-,-CO-NH-CO-NH-,-CONH-CR6 = N-,-CR6 = N-CO-NH-,-NR5-(CO)mO-或-NH-CR5 = N-,其中符号R5,R6和m如上定义,当R3和R4为1时, 2位和R7位于3位,或者当R3和R4位于3,4位,R7位于2位时,或者当R1和R2位于8,9位时,R7为 位于10位或当R1和R2为10,11位,R7为9位时,则R7为氢或C1-2烷氧基,否则R7为氢,条件是如果R1和R2为 氢然后R3和R4不能是氢。 这些化合物可用作颜料。
    • 7. 发明授权
    • Triphendioxazine compounds
    • 三苯并二恶嗪化合物
    • US06617453B1
    • 2003-09-09
    • US09718278
    • 2000-11-22
    • Bansi Lal KaulPatrick BoeglinPeter Kempter
    • Bansi Lal KaulPatrick BoeglinPeter Kempter
    • C07D49822
    • C07D498/22C09B19/02
    • The triphendioxazine compounds of the general formula (I) in which the rings labeled A in positions 1,2-, 2,3- or 3,4- and 8,9-, 9,10- or 10,11- carry a linearly or angularly fused heterocyclic ring containing at least one nitrogen atom which is substituted or unsubstituted, with the proviso that compounds with only unsubstituted nitrogen atoms and symmetrically disubstituted compounds with C1-2alkyl and unsubstituted phenyl substituents are excluded, are outstanding pigments and are notable over the closest comparable pigments in particular for better migration, light and solvent fastnesses, better heat stability and enhanced colouring power and also better dispersibility and capability to be brought into pigment form. The invention also relates to a process for preparing these triphendioxazine compounds which is characterized by a cyclization step conducted in the presence of manganese dioxide and concentrated sulphuric acid.
    • 通式(I)的三苯并二恶嗪化合物其中1,2-,2,3-或3,4-和8,9-,9,10-或10,11位上标记为A的环具有线性 或含有至少一个被取代或未取代的氮原子的角稠合杂环,条件是不包括仅具有未取代的氮原子和具有C 1-2烷基和未被取代的苯基取代基的对称二取代化合物的化合物是优异的颜料,并且在 特别是用于更好的迁移,轻和耐溶剂牢度,更好的热稳定性和增强的着色能力以及更好的分散性和能够进入颜料形式的最接近的可比颜料。本发明还涉及一种制备这些三苯并二恶嗪化合物的方法,其特征在于 在二氧化锰和浓硫酸存在下进行环化步骤。
    • 8. 发明授权
    • Process for preparing new crystal polymorphs of a methyl-substituted benzimidazolone-dioxazine pigment
    • 制备甲基取代的苯并咪唑酮 - 二恶嗪颜料的新晶体多晶型物的方法
    • US06620931B2
    • 2003-09-16
    • US10047829
    • 2001-10-22
    • Martin U. SchmidtPeter KempterRoland Born
    • Martin U. SchmidtPeter KempterRoland Born
    • C07D49822
    • C07D498/22C09B19/02
    • Process for phase conversion of a methyl-substituted, benzimidazolone-fused dioxazine pigment of composition C22H12Cl2N6O4 having the formula (1) or of an isomer or tautomer thereof, which comprises treating the pigment of formula (1) with certain organic solvents. In the course of this phase conversion, 4 novel crystal polymorphs are formed which are called phases II, IV, V and VI and are characterized by means of their X-ray powder diagrams. The novel polymorphs are of low solubility and feature good fastness properties and violet colorations. The novel crystal polymorphs are suitable for pigmenting coating materials, plastics, printing inks, aqueous or solvent-based pigment preparations, electrophotographic toners and developers, powder coating materials, inks, preferably inkjet inks, and color filters, and for coloring seed.
    • 具有式(1)的组合物C 22 H 12 Cl 2 N 6 O 4的甲基取代的苯并咪唑酮稠合二恶嗪颜料或其异构体或互变异构体的相转化方法,其包括用某些有机溶剂处理式(1)的颜料。 的相变,形成4个新的晶体多晶型物,称为II,IV,V和VI相,其特征在于它们的X射线粉末图。新型多晶型物具有低溶解度和特征,具有良好的牢度和紫色 新型晶体多晶型适用于着色涂料,塑料,印刷油墨,水性或溶剂型颜料制剂,电子照相色调剂和显影剂,粉末涂料,油墨,优选喷墨油墨和滤色剂,以及着色种子。
    • 9. 发明授权
    • Triphendioxazine compounds
    • 三苯并二恶嗪化合物
    • US06355795B1
    • 2002-03-12
    • US09583973
    • 2000-05-31
    • Patrick BoeglinBansi Lal KaulPeter Kempter
    • Patrick BoeglinBansi Lal KaulPeter Kempter
    • C07D49822
    • C07D498/22C09B19/02
    • The triphendioxazine compounds of the general formula (I) in which the rings labelled A in positions 1,2-, 2,3- or 3,4- and 8,9-, 9,10- or 10,11- carry a linearly or angularly fused heterocyclic ring containing at least one nitrogen atom which is substituted or unsubstituted, with the proviso that compounds with only unsubstituted nitrogen atoms and symmetrically disubstituted compounds with C1-2alkyl and unsubstituted phenyl substituents are excluded, are outstanding pigments and are notable over the closest comparable pigments in particular for better migration, light and solvent fastnesses, better heat stability and enhanced coloring power and also better dispersibility and capability to be brought into pigment form. The invention also relates to a process for preparing these triphendioxazine compounds which is characterized by a cyclization step conducted in the presence of manganese dioxide and concentrated sulphuric acid.
    • 通式(I)的三苯并二恶嗪化合物其中1,2-,2,3-或3,4-和8,9-,9,10-或10,11位上标记为A的环具有线性 或含有至少一个被取代或未取代的氮原子的角稠合杂环,条件是不包括仅具有未取代的氮原子和具有C 1-2烷基和未被取代的苯基取代基的对称二取代化合物的化合物是优异的颜料,并且在 特别是用于更好的迁移,轻和耐溶剂牢度,更好的热稳定性和增强的着色能力以及更好的分散性和能够进入颜料形式的最接近的可比颜料。本发明还涉及一种制备这些三苯并二恶嗪化合物的方法,其特征在于 在二氧化锰和浓硫酸存在下进行环化步骤。
    • 10. 发明授权
    • Triphendioxazine compounds
    • 三苯并二恶嗪化合物
    • US06255482B1
    • 2001-07-03
    • US09175139
    • 1998-10-19
    • Patrick BoeglinBansi Lal KaulPeter Kempter
    • Patrick BoeglinBansi Lal KaulPeter Kempter
    • C07D49804
    • C07D498/22C09B19/02
    • The triphendioxazine compounds of the general formula (I) in which the rings labelled A in positions 1,2-, 2,3- or 3,4- and 8,9-, 9,10- or 10,11- carry a linearly or angularly fused heterocyclic ring containing at least one nitrogen atom which is substituted or unsubstituted, with the proviso that compounds with only unsubstituted nitrogen atoms and symmetrically disubstituted compounds with C1-2alkyl and unsubstituted phenyl substituents are excluded, are outstanding pigments and are notable over the closest comparable pigments in particular for better migration, light and solvent fastnesses, better heat stability and enhanced colouring power and also better dispersibility and capability to be brought into pigment form. The invention also relates to a process for preparing these triphendioxazine compounds which is characterized by a cyclization step conducted in the presence of manganese dioxide and concentrated sulphuric acid.
    • 通式(I)的三苯并二恶嗪化合物其中1,2-,2,3-或3,4-和8,9-,9,10-或10,11位上标记为A的环具有线性 或含有至少一个被取代或未取代的氮原子的角稠合杂环,条件是不包括仅具有未取代的氮原子和具有C 1-2烷基和未被取代的苯基取代基的对称二取代化合物的化合物是优异的颜料,并且在 特别是用于更好的迁移,轻和耐溶剂牢度,更好的热稳定性和增强的着色能力以及更好的分散性和能够进入颜料形式的最接近的可比颜料。本发明还涉及一种制备这些三苯并二恶嗪化合物的方法,其特征在于 在二氧化锰和浓硫酸存在下进行环化步骤。