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    • 1. 发明授权
    • Mixed crystals of sulfonated diketopyrrolopyrroles
    • 磺化二酮吡咯并吡咯的混合晶体
    • US5380870A
    • 1995-01-10
    • US166750
    • 1993-12-14
    • Stefan HariOlof WallquistFritz HerrenThomas Eichenberger
    • Stefan HariOlof WallquistFritz HerrenThomas Eichenberger
    • C07D487/04C08K5/17C08K5/34C08K5/3412C08K5/3415C09B57/00C09B67/18C09B67/22C09B69/04
    • C07D487/04C09B67/0039C09B69/04
    • Mixed crystals of at least two different compounds of formula ##STR1## wherein A and B are each independently of the other a cation of formula ##EQU1## or N.sup.+ H(R.sub.1)(R.sub.2)(R.sub.3) M is a mono-, di- or trivalent metal cation, n is 1, 2 or 3, R.sub.1, R.sub.2 and R.sub.3 are each independently of one another hydrogen, C.sub.1 -C.sub.22 alkyl, C.sub.7 -C.sub.24 aralkyl, C.sub.5 -C.sub.6 cycloalkyl or C.sub.6 -C.sub.18 aryl, m is 0 or 1, and R is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, in which compounds of formula I that form the mixed crystals the cations A and B constitute a composite structure ##EQU2## wherein x is a value from 0.2 to 0.8, and the X-ray diffraction pattern of said mixed crystals differs from that of the corresponding compounds in which x is 1 or 0.These mixed crystals can be used as pigments for colouring organic material of high molecular weight and have exceptional properties, especially dispersibility, heat- and lightfastness.
    • 式(I)的至少两种不同的化合物的混合晶体,其中A和B各自独立地为式“阳离子”或“N + H”(R 1)(R 2)(R 3) - ,二价或三价金属阳离子,n为1,2或3,R 1,R 2和R 3各自独立地为氢,C 1 -C 22烷基,C 7 -C 24芳烷基,C 5 -C 6环烷基或C 6 -C 18芳基,m为0或 1,R是氢,C 1 -C 4烷基或C 1 -C 4烷氧基,其中形成阳离子A和B的混合晶体的式I化合物构成复合结构,其中x为0.2至0.8的值, 所述混晶的X射线衍射图与其中x为1或0的相应化合物的X射线衍射图不同。这些混合晶体可以用作高分子量有机材料着色的颜料,具有特别的性能,特别是分散性, 和耐光性。
    • 3. 发明授权
    • Monoazo compounds containing long-chain alkyl radicals
    • 含有长链烷基的单偶氮化合物
    • US4997920A
    • 1991-03-05
    • US405612
    • 1989-09-11
    • Stefan HariOlof WallquistJost von der Crone
    • Stefan HariOlof WallquistJost von der Crone
    • C07D239/88C07C245/06C07C245/10C07C255/65C07D235/26C07D263/58C07D265/36C07D277/82C08K5/00C08K5/23C08K5/34C08K5/35C08K5/46C09B29/01C09B29/20C09B29/33C09B67/20
    • C08K5/23C08K5/0041C09B29/0003C09B29/20C09B29/337C09B29/338
    • Compounds of the formulae I and II ##STR1## in which A is a radical of the formulae III, IV or V ##STR2## R.sub.1 and R.sub.4 are --H or --Cl, R.sub.2 and R.sub.5 are --H, halogen, --NO.sub.2, --CN, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 alkoxy, --CF.sub.3 or phenyloxy which is unsubstituted or substituted by one or two chlorine atoms and/or one or two methyl or methoxy groups, and R.sub.3 is alkyl having at least 10 C atoms, X is a radical of the formulae --NH--, --O--, ##STR3## n is the number 1 or 2, Y is the radical of the formulae --COO--, --OOC--, --CONH-- or --NHCO-- or a radical of the formulae ##STR4## in which R.sub.1 and R.sub.2 are as defined above, D is an aromatic heterocyclic 5- or 6-membered ring, in which the ring contains 1 or 2 N atoms and may additionally contain an O atom or S atom, Z is --H, --Br, --OCH.sub.3, --CN or --NO.sub.2 and X.sub.1 and X.sub.2, independently of one another, are --H, halogen, --CH.sub.3, --OCH.sub.3, --OC.sub.2 H.sub.5 or --NO.sub.2 and X.sub.3 is --H, --NHCO--C.sub.1 -C.sub.4 alkyl, benzoylamino or phenylcarboxamide which are each unsubstituted or substituted on the phenyl ring by one or two chlorine atoms and/or one or two methyl or methoxy groups or an --NHCO--C.sub.1 -C.sub.4 alkyl group, or X.sub.2 and X.sub.3 together with the carbon atom to which they are bound are an aromatic carbocyclic 6-membered ring or an aromatic heterocyclic 5- or 6-membered ring, in which the heterocyclic ring contains 1 or 2 N atoms and can additionally have an O atom or S atom, and Y.sub.1 is --H, --OCH.sub.3, --OC.sub.2 H.sub.5 or --NHCOCH.sub.3, with the proviso that X.sub.3 must not be H, if X is --O-- or --NH--, are highly suitable for the mass coloration of plastics, in particular of polyolefins.
    • 其中A是式III,IV或V的基团,其中A是式(I)的化合物,其中A是式III,IV或V的基团(III) (V)R 1和R 4是-H或-Cl,R 2和R 5是-H,卤素,-NO 2,-CN,C 1 -C 4 - 烷基,C 1 -C 4烷氧基,-CF 3或苯氧基,其未被取代或被 一个或两个氯原子和/或一个或两个甲基或甲氧基,并且R 3是具有至少10个C原子的烷基,X是式-NH-,-O-, 的基团 > + TR n是数字1或2,Y是式-COO-,-OOC-,-CONH-或-NHCO-的基团或式(IMAGE)+ TR 其中R1和R2如上定义,D是芳族杂环的5或6元环,其中环含有1或2个N原子,并且可以另外含有O原子或S原子,Z是-H, - Br,-OCH 3,-CN或-NO 2,X 1和X 2彼此独立地是-H,卤素,-CH 3,-OCH 3,-OC 2 H 5或-NO 2,X 3是-H,-NHCO-C 1 -C 4烷基, 苯甲酰氨基或苯基 甲酰胺,其各自未被取代或在苯环上被一个或两个氯原子和/或一个或两个甲基或甲氧基或-NHCO-C 1 -C 4烷基取代,或X 2和X 3与它们所在的碳原子一起 结合的是芳族碳环6元环或芳族杂环5或6元环,其中杂环含有1或2个N原子,并且可以另外具有O原子或S原子,Y 1是-H, - OCH 3,-OC 2 H 5或-NHCOCH 3,条件是如果X为-O-或-NH-,则X3不能为H,高度适用于塑料,特别是聚烯烃的大量着色。
    • 4. 发明授权
    • Disazo compounds containing long-chain alkyl ester radicals or
alkylamide radicals
    • 含有长链氨基酸酯或碱性氨基酸的灭菌化合物
    • US5071967A
    • 1991-12-10
    • US654140
    • 1991-02-11
    • Stefan HariJost von der Crone
    • Stefan HariJost von der Crone
    • C08K5/22C08K5/23C09B27/00C09B29/15C09B33/147C09B33/153C09B43/32
    • C09B43/32C08K5/235C09B27/00C09B29/106C09B33/153
    • Compounds of the formula I ##STR1## in which R is a radical of the formula --OR.sub.5 or --NHR.sub.5, A is a radical of the formula II or III ##STR2## in which B is a radical of the formula ##STR3## in which n is the number 1 or 2, R.sub.1 and R.sub.3 independently of one another are --H or Cl, R.sub.2 and R.sub.4 independently of one another are --H, halogen, --NO.sub.2, --CN, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, --CF.sub.3, C.sub.2 -C.sub.5 alkoxycarbonyl, or --CONH-phenyl, --NHCO-phenyl or phenyloxy which is unsubstituted or substituted on the phenyl nucleus by one or two chlorine atoms or one or two methyl, methoxy or ethoxy groups, R.sub.5 is alkyl having at least 10 C atoms, R.sub.6 and R.sub.7 independently of one another are --H, halogen, --NO.sub.2, --CN, --CF.sub.3, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, R.sub.8 is --H, --Cl, --Br, --CH.sub.3 or --OCH.sub.3 and X is --H, --Br, --OCH.sub.3, --CN or --NO.sub.2, are particularly suitable as pigments for coloring polyolefins.
    • 其中R为式-OR5或-NHR5基团的式I化合物(Ⅰ)化合物,A为式II或III的基团。 )其中B是式为“IMAGE”的基团,其中n为数1或2,R 1和R 3彼此独立地为-H或Cl,R 2和R 4彼此独立地为-H,卤素, - NO 2,-CN,C 1 -C 4烷基,C 1 -C 4烷氧基,-CF 3,C 2 -C 5烷氧基羰基或-CONH-苯基,-NHCO-苯基或苯氧基,其在苯基上被未取代或取代一个或两个氯原子或一个或 两个甲基,甲氧基或乙氧基,R5是具有至少10个C原子的烷基,R 6和R 7彼此独立地是-H,卤素,-NO 2,-CN,-CF 3,C 1 -C 4烷基或C 1 -C 4烷氧基,R 8是 -H,-Cl,-Br,-CH 3或-OCH 3,X为-H,-Br,-OCH 3,-CN或-NO 2,特别适合作为着色聚烯烃的颜料。
    • 5. 发明授权
    • Mono and disazo compounds based on b-hydroxy-naphthoic acid derivatives
or acetoacetarylide derivatives containing long-chain alkyl ester or
alkylamide radicals
    • 基于b-羟基 - 萘甲酸衍生物或含有长链烷基酯或烷基酰胺基团的乙酰乙酰胺衍生物的单和二重氮化合物
    • US4946948A
    • 1990-08-07
    • US401349
    • 1989-08-31
    • Stefan HariFridolin Babler
    • Stefan HariFridolin Babler
    • C08K5/00C08K5/23C09B29/15C09B33/147C09B33/153C09B43/124
    • C09B33/147C08K5/0041C08K5/235C09B29/103C09B33/153C09B43/124
    • Compounds of formula I: ##STR1## wherein R is a radical of the formula --OR.sub.3 or --NHR.sub.3, A is a radical of formula II or III: ##STR2## B is a radical of the formula ##STR3## n is the number 1 or 2, R.sub.1 is --H or --Cl, R.sub.2 is --H, halogen, --NO.sub.2, --CN, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, --CF.sub.3, C.sub.2 -C.sub.5 alkoxycarbonyl or --CONH-phenyl, --NHCO-phenyl or phenoxy which is unsubstituted or substituted on the phenyl ring by one or two chlorine atoms or one or two methyl, methoxy or ethoxy groups, R.sub.3 is alkyl containing at least 10 C atoms, R.sub.4 and R.sub.5 are each independently of the other --H, halogen, --NO.sub.2, --CN, --CF.sub.3, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, R.sub.6 is --H, --Cl, --Br, --CH.sub.3 or --OCH.sub.3 and X is --H, --Br, --OCH.sub.3, --CN or --NO.sub.2, are suitable as pigments, especially for coloring polyolefins, as well as novel intermediates of the formula ##STR4## wherein n is the number 1 or 2, R is a radical of the formula --OR.sub.3 or --NHR.sub.3, R.sub.1 is --H or --Cl, R.sub.2 is --H, halogen, --NO.sub.2, --CN, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, --CF.sub.3, C.sub.2 -C.sub.5 alkoxycarbonyl or --CONH-phenyl, --NHCO-phenyl or phenoxy which is unsubstituted or substituted on the phenyl ring by one or two chlorine atoms or one or two methyl, methoxy or ethoxy groups, R.sub.3 is alkyl containing at least 10 C atoms, X is --H, --Br, --OCH.sub.3, --CN or --NO.sub.2 and Q is --OH or halogen.
    • 式I化合物:其中R是式-OR3或-NHR3基团,A是式II或III的基团:(III)B是 式中的基团+图像n为数1或2,R 1为-H或-Cl,R 2为-H,卤素,-NO 2,-CN,C 1 -C 4烷基,C 1 -C 4烷氧基 ,-CF 3,C 2 -C 5烷氧基羰基或-CONH-苯基,-NHCO-苯基或苯氧基,其在苯环上未被取代或被一个或两个氯原子或一个或两个甲基,甲氧基或乙氧基取代,R3是含有 至少10个C原子,R 4和R 5各自独立地为H,卤素,-NO 2,-CN,-CF 3,C 1 -C 4烷基或C 1 -C 4烷氧基,R 6为-H,-Cl,-Br, -CH 3或-OCH 3,X是-H,-Br,-OCH 3,-CN或-NO 2,适合作为颜料,特别是用于着色聚烯烃,以及下式的新型中间体:其中n为数1 或2,R是式-OR 3或-NHR 3的基团,R 1是-H或-Cl,R 2是-H,卤素,-NO 2,-CN,C 1 -C 4烷基,C 1 -C 4烷氧基,-CF 3, C2 -C 5烷氧基羰基或-CONH-苯基,-NHCO-苯基或苯氧基,其在苯环上未被取代或被一个或两个氯原子或一个或两个甲基,甲氧基或乙氧基取代,R3是含有至少10个C原子的烷基 ,X是-H,-Br,-OCH 3,-CN或-NO 2,Q是-OH或卤素。
    • 9. 发明授权
    • Disazo pigments containing acylamino groups
    • 含有酰氨基的双偶氮颜料
    • US4062838A
    • 1977-12-13
    • US686431
    • 1976-05-14
    • Georg CsehStefan Hari
    • Georg CsehStefan Hari
    • C09B33/153C09B33/14
    • C09B33/153
    • Disazo pigments of the formula ##STR1## wherein A denotes a phenylene or naphthylene radical, R denotes an aryl, alkyl or alkenyl group optionally substituted by halogen atoms, by hydroxyl, alkoxy or alkylmercapto groups containing 1-6 C atoms, by alkoxycarbonyl groups containing 2-6 C atoms or cyano, aryl, aryloxy, arylmercapto or heterocyclic radicals, or denotes a heterocyclic radical, and the X and Y denote H atoms or substituents which do not confer solubility in water are useful for coloring plastics lacquers and printing inks in yellow to orange shade of good fastness properties.
    • 其中A表示亚苯基或亚萘基,R表示任选被卤素原子取代的芳基,烷基或烯基,含1-6个碳原子的羟基,烷氧基或烷基巯基,通过含有 2-6个C原子或氰基,芳基,芳氧基,芳基巯基或杂环基,或表示杂环基,X和Y表示H原子或不赋予溶于水的取代基可用于着色塑料漆和印刷油墨 黄色至橙色,色牢度好。
    • 10. 再颁专利
    • Amine salts of azo pigments based on pyrazolone derivatives
    • 基于吡唑啉酮衍生物的偶氮颜料的胺盐
    • USRE35359E
    • 1996-10-22
    • US312209
    • 1994-09-26
    • Stefan HariGeorg Cseh
    • Stefan HariGeorg Cseh
    • C08K5/34C08K5/3442C08K5/3445C08K5/41C08K5/42C08L101/00C09B29/01C09B29/46C09B29/50C09B69/04C09B29/03C09B29/10D06P1/44D06P5/00
    • C09B29/0007C09B29/366C09B69/045
    • Compounds of formula ##STR1## wherein a and b are each independently of the other halogen, --CH.sub.3, --C.sub.2 H.sub.5, --OC.sub.2 H.sub.5 or the group of formula --NHCO--C.sub.1 -C.sub.4 alkyl, c and d are each independently of the other hydrogen, halogen, --CH.sub.3, --C.sub.2 H.sub.5, --OCH.sub.3, --OC.sub.2 H.sub.5 or the group of formula --NHCO--C.sub.1 -C.sub.4 alkyl, and R.sup.1 is --CH.sub.3, phenyl, --COOCH.sub.3, --COOC.sub.2 H.sub.5, --NHCO--C.sub.1 --C.sub.4 alkyl or --CONH--C.sub.1 -C.sub.4 alkyl, and R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are each independently hydrogen, C.sub.1 -C.sub.4 alkyl, unsubstituted or substituted by a chlorine atom or a --OH group, or are C.sub.7 -C.sub.9 aralkyl, C.sub.6 -C.sub.8 cycloalkyl, phenyl or phenyl which is substituted by 1 to 3 halogen atoms or methyl or methoxy groups, or is a heterocyclic radical of the benzimidazole, benzoxazole, benzthiazole or pyridine series, or R.sup.3 and R.sup.4, together with the linking nitrogen atom, are a pyrrolidine, imidazolidine, piperidine, piperazine or morpholine radical, or R.sup.3, R.sup.4 and R.sup.5, together with the linking nitrogen atom, are a pyrrole, pyridine, picoline, pyrazine, quinoline or isoquinoline radical, are most suitable for coloring high molecular organic material.
    • 式(I)的化合物其中a和b各自独立于其它卤素,-CH 3,-C 2 H 5,-OC 2 H 5或式-NHCO-C 1 -C 4烷基基团,c和d各自独立地为另一个 氢,卤素,-CH 3,-C 2 H 5,-OCH 3,-OC 2 H 5或式-NHCO-C 1 -C 4烷基的基团,并且R 1是-CH 3,苯基,-COOCH 3,-COOC 2 H 5,-NHCO-C 1 -C 4烷基或-CONH C 1 -C 4烷基,R 2,R 3,R 4和R 5各自独立地为氢,未被取代或被氯原子或-OH基取代的C 1 -C 4烷基,或者是C 7 -C 9芳烷基,C 6 -C 8环烷基,苯基或苯基, 被1〜3个卤素原子取代或甲基或甲氧基,或者是苯并咪唑,苯并恶唑,苯并噻唑或吡啶系列的杂环基,或R3和R4与连接氮原子一起是吡咯烷,咪唑烷,哌啶,哌嗪 或吗啉基,或R 3,R 4和R 5与连接氮原子一起为吡咯,吡啶,甲基吡啶,吡嗪,喹啉或异喹啉基, 最适合着色高分子有机材料。