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    2.
    发明专利
    未知

    公开(公告)号：DE4305714A1

    公开(公告)日：1994-09-01

    申请号：DE4305714

    申请日：1993-02-25

    Applicant: HOECHST AG

    Inventor： DIETZ ERWIN DR ,  KAPAUN GUSTAV DR

    IPC: C07D235/16

    Abstract: A process for the preparation of substituted or unsubstituted 2-(cyanomethyl)benzimidazole of the formula (I) is characterised in that an o-phenylenediamine of the formula (II) in which R is C1-C4-alkyl or C1-C4-alkoxy, preferably methyl or methoxy, and n is an integer from 0 to 2, preferably 0 or 1, in particular 0, is reacted with a cyanoacetic ester of the formula (III> NC-CH2-COOR (III> in which R is unsubstituted or substituted, linear, branched or cyclic C2-C12-alkyl and in which 1 to 3 CH2 groups of the alkyl radical can be replaced in each case by oxygen, at a temperature of 150 - 175@C in a halogen-free inert solvent whose boiling point is equal to or greater than 150@C, or in a mixture of two or more such solvents, without an addition of an aromatic sulphonic acid as catalyst. Using the process according to the invention, 2-(cyanomethyl)benzimidazoles are prepared in good yields and high purity without the use of a catalyst.

    3.
    发明专利
    未知

    公开(公告)号：DE3887744D1

    公开(公告)日：1994-03-24

    申请号：DE3887744

    申请日：1988-12-20

    Applicant: HOECHST AG

    Inventor： DIETZ ERWIN DR ,  KAPAUN GUSTAV DR ,  KAPPERT MICHAEL DR ,  PROKSCHY FRANK DR ,  KROH ADOLF ,  URBAN MANFRED

    IPC: C09B1/00 ,  C08K5/03 ,  C09B3/14 ,  C09B3/22 ,  C09B3/40 ,  C09B5/16 ,  C09B5/20 ,  C09B5/48 ,  C09B5/62 ,  C09B19/02 ,  C09B47/04 ,  C09B47/12 ,  C09B57/04 ,  C09B67/20 ,  C09B69/00

    Abstract: Pigments of the formula I (I) where A is a five- or six-membered aromatic fused or unfused heterocycle which contains one to three hetero atoms from the series consisting of nitrogen and/or oxygen and/or sulfur and which is bonded to the methylene group via a carbon atom, R1 and R2 are each hydrogen, alkyl C1-C4, alkylene C2 or aryl, and together R1 and R2 may also be an aliphatic or aromatic ring, R3 is hydrogen, alkyl C1-C4+L, hydroxylkyl C1-C3 or alkylene C2, P is the radical of a polycyclic pigment or a radical of a mix-crystal of polycyclic pigments, and n is a number from 0.0001 to 0.2, are useful for pigmenting high molecular weight materials in the form of plastic materials, melts, spinning solutions, surface coatings, paints, printing inks, baking finishes of the class of the alkyd melamine resin or acrylic melamine resin finishes, two-component coatings based on polyisocyanate-crosslinkable acrylic resins and printing inks based on nitrocellulose.

    4.
    发明专利
    未知

    公开(公告)号：DE4419849A1

    公开(公告)日：1995-12-14

    申请号：DE4419849

    申请日：1994-06-07

    Applicant: HOECHST AG

    Inventor： ALFTER FRANK DR ,  DIETZ ERWIN DR ,  KAPAUN GUSTAV DR ,  SCHIESLER SIEGFRIED DR

    IPC: C07D209/44 ,  C08K5/3417 ,  C09B57/04 ,  C09D7/12 ,  D06P5/00 ,  G03G5/06 ,  C09B67/20 ,  C09D17/00 ,  C09D11/02 ,  C07D403/12 ,  C07D403/14 ,  C07D417/12 ,  C08L23/02

    Abstract: Novel isoindoline pigments of formula (I) are claimed, as are also (i) prepn. of (I) by reacting an isoindoline of formula (II) having nucleophilically-exchangeable gps. X and Y in the 1- and 3-positions with a cpd. of formula (III) in which the H atoms of the -CH2- gp. are CH acids so as to give an intermediate of formula (IV) which is then reacted with a benzimidazolone of formula (V); and (ii) the use of (I) in pigmenting high mol. wt. organic materials. R = CN; R = (a) CN; (b) an (un)satd. (non)aromatic 5-7 membered N, O and/or S heterocyclic ring opt. modified by condensation or bridging to further heterocyclic or isocyclic ring systems; (c) -CONR R where R and R = H or 1-4C alkyl; or (d) -CONR R where R = unsubstd. or with at least 5 1-4C alkyl, halogen, CF3, 1-4C alkoxy, carbo(m)ethoxy or carbonamide- or with one 1-4C alkyl or phenyl gp.-substd. carbonamide, NO2, 1-4C alkylamino or OH-substd. (un)satd., (non)aromatic, iso- or hetero-cyclic (N, O and/or S) 5-7-membered ring opt. modified as per the ring of (b) above; or R and R together = ring as per (b) above opt. substd. as per (d) but excluding NO2; R = H, 1-4C alkyl, phenyl, 1-4C alkoxy, halogen or 1-4C acylamino; R = H, 1-4C alkyl, halogen, CF3, MeO, EtO or NO2; m = 1, 2, 3 or 4; n = 1, 2 or 3; and R = H or 1-4C alkyl.

    6.
    发明专利
    未知

    公开(公告)号：DE19516804A1

    公开(公告)日：1996-11-14

    申请号：DE19516804

    申请日：1995-05-08

    Applicant: HOECHST AG

    Inventor： ALFTER FRANK DR ,  JUNG RUEDIGER DR ,  KAPAUN GUSTAV DR

    IPC: C09B55/00 ,  C07D403/12 ,  C09B57/04 ,  C09B67/20 ,  C09D7/12 ,  C09D11/00

    Abstract: Isoindoline pigments of formula (I) are claimed, where R and R are each CN; Q is -CO-NR R or -CO-NR R ; or R +R = R ; Q is a (non)satd. (non)aromatic 5-7-membered heterocyclic ring system, opt. modified by condensn. or bridging to other heterocyclic or isocyclic ring systems, in which the hetero-atoms are N, O and/or S; R and R are each H or 1-4C alkyl; R is Q, opt. mono- to penta-substd. by 1-4C alkyl, halogen, CF3, 1-4C alkoxy, carbo(m)ethoxy, carbonamido (opt. substd. by 1-4C alkyl or phenyl), NO2, 1-4C acylamino or OH; R is H, 1-4C alkyl, phenyl, 1-4C alkoxy, halogen or 1-4C acylamino; R is H, 1-4C alkyl, halogen, CF3, OMe, OEt or NO2; m = 1-4; n = 1-3; and R is H or 1-4C alkyl. (I) are prepd. by reacting (a) an isoindoline cpd. (II) of formula (A: X and Y are gps. X and Y capable of nucleophilic exchange in the 1- and 3-positions) with (b) a cpd. of formula R -CH2-R (III), giving a cpd. (IV) of formula (A: X is CR R ); and then (b) reacting (IV) with a quinoxalindione of formula (V), esp. a 6-aminoquinoxalindione. In (III), X is pref. imino, (hemi)acetal or ketal gp.; and Y is pref. an imino gp.. In (II), H atoms in the -CH2- gp. are CH-acids. Stage (a) is carried out at 30-60, pref. 45-55 degrees C and pH 5-9, pref. 6-8.5.

    7.
    发明专利
    未知

    公开(公告)号：DE3838814A1

    公开(公告)日：1989-07-06

    申请号：DE3838814

    申请日：1988-11-17

    Applicant: HOECHST AG

    Inventor： DIETZ ERWIN DR ,  KAPAUN GUSTAV DR ,  KAPPERT MICHAEL DR ,  PROKSCHY FRANZ DR ,  KROH ADOLF DIPL ING ,  URBAN MANFRED DIPL ING

    IPC: C09B1/00 ,  C08K5/03 ,  C09B3/14 ,  C09B3/22 ,  C09B3/40 ,  C09B5/16 ,  C09B5/20 ,  C09B5/48 ,  C09B5/62 ,  C09B19/02 ,  C09B47/04 ,  C09B47/12 ,  C09B57/04 ,  C09B67/20 ,  C09B69/00

    Abstract: Pigments of the formula I (I) where A is a five- or six-membered aromatic fused or unfused heterocycle which contains one to three hetero atoms from the series consisting of nitrogen and/or oxygen and/or sulfur and which is bonded to the methylene group via a carbon atom, R1 and R2 are each hydrogen, alkyl C1-C4, alkylene C2 or aryl, and together R1 and R2 may also be an aliphatic or aromatic ring, R3 is hydrogen, alkyl C1-C4+L, hydroxylkyl C1-C3 or alkylene C2, P is the radical of a polycyclic pigment or a radical of a mix-crystal of polycyclic pigments, and n is a number from 0.0001 to 0.2, are useful for pigmenting high molecular weight materials in the form of plastic materials, melts, spinning solutions, surface coatings, paints, printing inks, baking finishes of the class of the alkyd melamine resin or acrylic melamine resin finishes, two-component coatings based on polyisocyanate-crosslinkable acrylic resins and printing inks based on nitrocellulose.

    8.
    发明专利
    未知

    公开(公告)号：DE59400419D1

    公开(公告)日：1996-08-22

    申请号：DE59400419

    申请日：1994-02-16

    Applicant: HOECHST AG

    Inventor： DIETZ ERWIN DR ,  KAPAUN GUSTAV DR

    IPC: C07D235/16

    Abstract: A process for the preparation of substituted or unsubstituted 2-(cyanomethyl)benzimidazole of the formula (I) is characterised in that an o-phenylenediamine of the formula (II) in which R is C1-C4-alkyl or C1-C4-alkoxy, preferably methyl or methoxy, and n is an integer from 0 to 2, preferably 0 or 1, in particular 0, is reacted with a cyanoacetic ester of the formula (III> NC-CH2-COOR (III> in which R is unsubstituted or substituted, linear, branched or cyclic C2-C12-alkyl and in which 1 to 3 CH2 groups of the alkyl radical can be replaced in each case by oxygen, at a temperature of 150 - 175@C in a halogen-free inert solvent whose boiling point is equal to or greater than 150@C, or in a mixture of two or more such solvents, without an addition of an aromatic sulphonic acid as catalyst. Using the process according to the invention, 2-(cyanomethyl)benzimidazoles are prepared in good yields and high purity without the use of a catalyst.

    9.
    发明专利
    未知

    公开(公告)号：DE58906443D1

    公开(公告)日：1994-01-27

    申请号：DE58906443

    申请日：1989-10-24

    Applicant: HOECHST AG

    Inventor： DIETZ ERWIN DR ,  KAPAUN GUSTAV DR ,  SCHIESSLER SIEGFRIED DR

    IPC: C09B57/12

    Abstract: In the context of the conventional condensation of naphthalene- 1,4,5,8-tetracarboxylic acid with 1,2-diaminobenzene, the napthoylene- bis-benzimidazole isomers formed are obtained together in the cis and transform. In practice, there was the object of shifting the isomer ratio of the mixture obtained, i.e. of increasing the yield of the desired trans product and of reducing the yield of the cis product. At the same time, there was the necessity to develop a preparation process which optimised the yield and improved the waste water situation. This object is achieved according to the invention in that the starting compounds are subjected to a precondensation at 60 DEG to 110 DEG C in aqueous medium using virtually stoichiometric initial amounts and the condensation is then completed in a second step at 130 DEG to 180 DEG C.

    10.
    发明专利
    未知

    公开(公告)号：DE3836674A1

    公开(公告)日：1990-05-03

    申请号：DE3836674

    申请日：1988-10-28

    Applicant: HOECHST AG

    Inventor： DIETZ ERWIN DR ,  KAPAUN GUSTAV DR ,  SCHIESSLER SIEGFRIED DR

    IPC: C09B57/12

    Abstract: In the context of the conventional condensation of naphthalene- 1,4,5,8-tetracarboxylic acid with 1,2-diaminobenzene, the napthoylene- bis-benzimidazole isomers formed are obtained together in the cis and transform. In practice, there was the object of shifting the isomer ratio of the mixture obtained, i.e. of increasing the yield of the desired trans product and of reducing the yield of the cis product. At the same time, there was the necessity to develop a preparation process which optimised the yield and improved the waste water situation. This object is achieved according to the invention in that the starting compounds are subjected to a precondensation at 60 DEG to 110 DEG C in aqueous medium using virtually stoichiometric initial amounts and the condensation is then completed in a second step at 130 DEG to 180 DEG C.

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