Ring Carbon Is Shared By Three Of The Cyclos (e.g., Perylene Tetracarboxylic Acid Diimide, Etc.) Patents (Class 546/37)
  • Patent number: 5464841
    Abstract: A therapeutic method is provided to elevate a depressed mammalian autologous mixed lymphocyte response and to alleviate the diseases associated therewith by the administration of an effective amount of certain selective delta opioid receptor antagonists to a mammal such as a human patient in need of such treatment.
    Type: Grant
    Filed: November 8, 1993
    Date of Patent: November 7, 1995
    Inventors: Philip S. Portoghese, Burt M. Sharp, Kristin M. Linner
  • Patent number: 5459268
    Abstract: The dyes of the present invention are fluorescent substituted 3',6'-diaminoxanthenes and their reduced analogs 3',6'-diaminodihydroxanthenes, which are oxidized to the fluorescent form of the dye in situ. In their oxidized form, the dyes selectively localize within mitochondria. The dyes of the present invention include an alkylating group that is covalently attached that allows their retention in mitochondria even after cell death, fixation, and permeabilization.
    Type: Grant
    Filed: October 25, 1993
    Date of Patent: October 17, 1995
    Assignee: Molecular Probes, Inc.
    Inventors: Richard P. Haugland, Mohammad N. Malekzadeh, Yu-zhong Zhang
  • Patent number: 5453517
    Abstract: The invention relates to fluorescent and/or reactive derivatives of 1,2-bis-(2-aminophenoxyethane)-N,N,N',N'-tetraacetic acid (BAPTA) according to the formula: ##STR1## where at least one of W and X is a functional group, with or without a spacer, that terminates in an alcohol or phenol, a thiol, a haloacetamide, an alkyl halide, an amine or aniline, a carboxylic acid, an anhydride, an isocyanate, an isothiocyanate, a maleimide, or an activated ester. The BAPTA-like molecule may be further substituted, one or more times, by additional functional groups with or without spacers or by CH.sub.3, NO.sub.2, CF.sub.3, F, Cl, Br, I, or carboxylic acid derivatives or pharmaceutically acceptable salts thereof, or by indolyl or benzofuran fluorophores. The functional groups allow for subsequent covalent attachment of one or more oxygen heterocycle fluorophores (e.g. fluorescein, coumarin, rhodamine); or polymolecular assemblies (e.g.
    Type: Grant
    Filed: February 25, 1992
    Date of Patent: September 26, 1995
    Assignee: Molecular Probes, Inc.
    Inventors: Michael A. Kuhn, Richard P. Haugland
  • Patent number: 5420234
    Abstract: Bis-N-aminoimides of formula (III): ##STR1## wherein m is 0 or 1 and ##STR2## is a mono- or polycyclic aromatic radical, can be employed to produce a variety of polymers of the type produced from diamines, including polyimides having an N--N linkage; polymers can be produced having exceptionally high glass transition temperatures, but which are also soluble in organic solvents; colored polymers and electroconductive polymers and photoconductive polymers can also be produced.
    Type: Grant
    Filed: July 26, 1994
    Date of Patent: May 30, 1995
    Inventors: Allan S. Hay, Hossein Ghassemi
  • Patent number: 5359092
    Abstract: Bis-N-aminoimides of formula (III): ##STR1## wherein m is 0 or 1 and is a mono- or polycyclic aromatic radical, can be employed to produce a variety of polymers of the type produced from diamines, including polyimides having an N--N linkage; polymers can be produced having exceptionally high glass transition temperatures, but which are also soluble in organic solvents; coloured polymers and electroconductive polymers and photoconductive polymers can also be produced.
    Type: Grant
    Filed: June 2, 1993
    Date of Patent: October 25, 1994
    Inventors: Allan S. Hay, Hossein Ghassemi
  • Patent number: 5332818
    Abstract: An immunosuppressive agent which has low toxicity and which exhibits excellent effectiveness even if it is orally administered is presented. The immunosuppressive agent of the present invention is characterized in that it contains .delta.-opioid antagonist having high selectivity to .delta.-opioid receptor. The present invention also provides a process of producing a naltrindole derivative characterized by reacting naltrexone or a salt thereof with a phenylhydrazine derivative in a solvent in the presence of methanesulfonic acid.
    Type: Grant
    Filed: March 22, 1993
    Date of Patent: July 26, 1994
    Assignee: Toray Industries, Inc.
    Inventors: Hiroshi Nagase, Koji Kawai, Shu Matsumoto, Takashi Endoh, Yoshiaki Katsura, Kohei Arakawa
  • Patent number: 5319083
    Abstract: The invention relates to perylene-3,4,9,10-tetracarboxylic diimides of the formula (I) ##STR1## in which R is a 3'- and/or 4'-methoxybenzyl radical, and their preparation and use as black pigments, inter alia in paint preparations, printing inks or for the dyeing of polymers.
    Type: Grant
    Filed: December 16, 1992
    Date of Patent: June 7, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Helmut Troster
  • Patent number: 5280121
    Abstract: Compounds of formula ##STR1## wherein R is C.sub.7 -C.sub.21 alkyl, C.sub.4 -C.sub.18 alkenyl, C.sub.5 -C.sub.12 cycloalkyl or C.sub.5 -C.sub.6 cycloalkyl-substituted C.sub.1 -C.sub.4 alkyl,R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each independently of one another hydrogen, chloro, bromo, methyl or methoxy,Z is a direct bond or --O--, --S--, --NH--, --CO--, --SO.sub.2 -- or --NHCO--, andn is 0 or 1.These compounds have excellent suitability as pigments for coloring organic material of high molecular weight, especially polyvinyl chloride, polyolefins and paints.
    Type: Grant
    Filed: June 30, 1992
    Date of Patent: January 18, 1994
    Assignee: Ciba-Geigy Corporation
    Inventor: Stefan Hari
  • Patent number: 5278168
    Abstract: Biological applications of synthetic and natural alkaloids derived from the tunicate Eudistoma sp. are disclosed. A method regulating cell growth includes contacting one or more cells with an effective concentration of a compound for regulating cell growth. These compounds include: Segoline A, Segoline B, Isosegoline A, Norosegoline, Debromoshermilamine, Eilatin, 4-methylpyrido[2,3,4-kl] acridine, pyrido[2,3,4-kl]acridine, 1-acetyl-2,6-dimethylpyrido[2,3,4-kl]acridine, and derivatives and combinations of these compounds. An effective concentration range for using these compounds can range from approximately 0.1 .mu.M to 100 .mu.M. The effective concentration range for Eilatin, the most potent of these compounds is from 0.01 .mu.M to 0.99 .mu.M, and the effective concentration range for the other compounds of the present invention is from about 1.0 .mu.M to 100 .mu.M.
    Type: Grant
    Filed: August 3, 1992
    Date of Patent: January 11, 1994
    Assignee: The Research Foundation of State Univeristy of New York
    Inventors: Ilan Spector, Nava R. Shochet, Yoel Kashman, Amira Rudi
  • Patent number: 5264034
    Abstract: Pigment preparations consisting essentially of (a) at least one pigment based on perylene-3,4,9,10-tetracarboxylic dianhydride or on corresponding monoimides or diimides of tetracarboxylic acid monoanhydride, or a halogenation product thereof, (b) at least one pigment dispergent based on perylene-3,4,9,10-monoimide substituted on one or both imide nitrogen atoms by alkylene or arylene sulphonic or carboxylic acid groups or on corresponding diimides of tetracarboxylic acid monoanhydride, or a halogenation product thereof. The dispergents used appreciably enhance the key properties of perylene pigments, such as dispersibility, coloring power, stability to flocculation, transparency, rheological behavior and surface properties of the application medium. These new preparations are suitable for the pigmentation of high-quality lacquers and synthetic resins.
    Type: Grant
    Filed: March 6, 1992
    Date of Patent: November 23, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Erwin Dietz, Manfred Urban
  • Patent number: 5248774
    Abstract: Perylenetetracarboxylic diimides which contain a radical in the same molecule on one imide nitrogen which acts as an anion but contain a radical on the other imide nitrogen which acts as a cation, and on this basis form inner salts, are available by reaction of sulfo-containing alkylamines with perylenetetracarboxylic monoanhydride monoalkylaminoalkylimides or by reaction of alkylaminoalkylamines with perylenetetracarboxylic monoanhydride monosulfoalkylimides. As a result of their characteristic structural principle, these novel perylene compounds have excellent dispersing properties, in particular for pigments of the same chemical classes of compounds and can even be used themselves as pigments (colorants) depending on the substituent.
    Type: Grant
    Filed: March 20, 1992
    Date of Patent: September 28, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Erwin Dietz, Manfred Urban
  • Patent number: 5247088
    Abstract: This invention relates to a novel process for the continuous preparation of perylenetetracarboxylic diimides by fusion of a naphthalimide in a mixture of an alkali metal hydroxide and, optionally, an alkali metal carboxylate to form an initial leuko condensation product that is subsequently oxidized in an aqueous medium to form the perylenetetracarboxylic diimide.
    Type: Grant
    Filed: July 30, 1991
    Date of Patent: September 21, 1993
    Assignee: Miles Inc.
    Inventor: Thomas R. Flatt
  • Patent number: 5212312
    Abstract: Dyes of the formula ##STR1## in which F is the radical of an indigoid dye, of a benzothioxanthene or of an aromatic dye which contains at least 4 alicyclic and/or heterocyclic, fused six-membered rings and at least two ring keto groups and is not water-soluble, R.sub.1 is a substituted or unsubstituted C.sub.1-4 -alkyl radical, a substituted or unsubstituted cycloalkyl radical, a substituted or unsubstituted aryl radical or a radical of the formula--A--Qwhere A is a substituted or unsubstituted C.sub.1-4 -alkylene radical and Q is a basic radical, which may be quaternised, and R.sub.2 is hydrogen or a substituted or unsubstituted C.sub.1-4 -alkyl radical, or in which R.sub.1 and R.sub.2 together with the ##STR2## group are a phthalimide radical, and R.sub.3 is hydrogen, a substituted or unsubstituted C.sub.1-4 -alkyl radical, a substituted or unsubstituted aryl radical, a C.sub.1-4 -alkoxycarbonyl radical or a N,N-di-C.sub.1-4 -alkylcarboxamide radical and n is 1, 2, 3 or 4.
    Type: Grant
    Filed: September 22, 1986
    Date of Patent: May 18, 1993
    Assignee: Ciba-Geigy AG
    Inventors: Jean-Marie Adam, Athanassios Tzikas
  • Patent number: 5180828
    Abstract: Compounds and methods for detecting the incorporation of a hapten into a protein or macromolecules are disclosed. The compounds comprise haptens bound directly or indirectly to a chromophoric group and a macromolecules-reactive group, whereby incorporation of the hapten into a protein or other macromolecules may be detected. The disclosure includes a compound of the formula: ##STR1## wherein n.sub.1 is 1, 2, 3, 4, 5, 6 or 7;n.sub.2 is 0, 1, 2, 3, 4, 5, 6 or 7;R.sub.1 is either a carboxytetramethyl-rhodamyl, sulforhodamyl101, or dinitrophenylaminohexanoyl group; andR.sub.2 is --CO.sub.2 H, --NH.sub.
    Type: Grant
    Filed: April 9, 1992
    Date of Patent: January 19, 1993
    Assignee: Molecular Devices Corporation
    Inventors: Vartan Ghazarossian, Viola T. Kung, Robert F. Zuk
  • Patent number: 5154770
    Abstract: Perylenetetracarbimide mix-crystal pigments in the crystal lattice of the .alpha.-modification of N,N'-bis-3',5'-dimethylphenylperylenetetracarbimide of the formula (1) comprising 99-70 mole percent of the symmetrical diimide of the formula (1) and correspondingly 1-30 mole percent of the asymmetrically substituted diimide of the formula (2) ##STR1## process for their preparation and their use for coloring organic polymers.
    Type: Grant
    Filed: September 19, 1990
    Date of Patent: October 13, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ernst Spietschka, Helmut Troster
  • Patent number: 5151516
    Abstract: Perylimides useful as monomers have the formula ##STR1## wherein R.sup.1 is C.sub.1 -C.sub.20 -alkyl which may be interrupted by one or more oxygen atoms or is substituted phenyl,R.sup.2 has the meanings hydrogen, chlorine or substituted or unsubstituted phenoxy independently of one another in its four appearances,X is a chemical bond or a radical of the formula ##STR2## where R.sup.3 and R.sup.4 are each independently of the other hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or halogen m is 1 or 2, and n is 0 or 1,Y is C.sub.6 -C.sub.14 -alkylene which may be interrupted by one or more oxygen atoms or by one or more imino or C.sub.1 -C.sub.4 -alkylimino groups, andZ is vinyl, acryloyloxy or acryloxylamino.
    Type: Grant
    Filed: October 12, 1990
    Date of Patent: September 29, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Karin H. Beck, Karl-Heinz Etzbach, Hans-Werner Schmidt
  • Patent number: 5145964
    Abstract: Brilliant and easily dispersible perylene-3,4,9,10-tetracarboxydiimide pigments of high color strength and N-alkyl derivatives thereof having 1 to 4 carbon atoms per alkyl group can be prepared by subjecting finely divided crude pigments to a treatment by means of a mixture of water and an organic solvent from the class of alcohols, ketones, carboxylic acids or carboxylic esters.
    Type: Grant
    Filed: February 28, 1991
    Date of Patent: September 8, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Detlef-Ingo Schutze, Dietmar Muller
  • Patent number: 5123966
    Abstract: In the art of pigmenting high molecular weight organic materials there is a long-felt need for high-hiding organic red pigments, in particular yellowish red pigments, which are increasingly used to replace the ecologically unsafe inorganic red pigments. However, this gap in the market cannot be satisfactorily filled by using the tetrachloroperylenetetracarboximide pigments known for the aforementioned purpose.According to the invention, it has now been found that a chlorine content of .ltoreq.25% in such chlorinated perylimides confers remarkable coloristic properties on the pigments thus produced, so that these pigments are superior in hiding powder and masstone to the tetrachloroperylimide compounds described. Accordingly, the invention is directed to high-hiding red pigments of the type of the halogenated perylenetetracarboximides containing up to 4 chlorine atoms, whose chlorine content is 15-25% and which are present as mixed crystal pigments in the .beta.
    Type: Grant
    Filed: December 12, 1990
    Date of Patent: June 23, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Erwin Dietz, Manfred Urban
  • Patent number: 5122306
    Abstract: Compositions adapted to be reacted with hydrogen peroxide to provide chemiluminescent light are disclosed wherein the fluorescer is a perylene derivative.
    Type: Grant
    Filed: June 19, 1990
    Date of Patent: June 16, 1992
    Assignee: American Cyanamid Company
    Inventors: Andre Van Moer, Jacques Ladyjensky
  • Patent number: 5110931
    Abstract: Prepration of N,N'-dimethylperylene-3,4,9,10-tetracarboxylic diimide (DMP) ##STR1## in high-hiding pigment form by reacting perylene-3,4,9,10-tetracarboxylic dianhydride with methylamine. The reaction is carried out at 40.degree. to 200.degree. C. and the excess methylamine is distilled off only after the perylene-3,4,9,10-tetracarboxylic dianhydride used has been fully converted to the methylammonium salts of the corresponding N,N'-dimethyldicarbamoylperylenedicarboxylic acids. The temperature is held at 140.degree. to 200.degree. C. after, or after and during the formation of the DMP. The resultant highly crystalline crude pigment in aqueous suspension which has a mean particle size D.sub.50% (mass distribution) of 0.15 to 0.4 .mu.m and a mean length-to-width ratio q950% (mass distribution of the pigment particles of 10:1 to 3:1, is grounded in aqueous suspension until the mean particle size is 0.1 to 0.2 .mu.m and the mean length-to-width ratio of the pigment particles is less than 5:1.
    Type: Grant
    Filed: November 8, 1989
    Date of Patent: May 5, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Erwin Dietz, Manfred Urban
  • Patent number: 5104918
    Abstract: Perylene-3,4,9,10-tetracarboxylic acid diimides of the formula I ##STR1## in which R is a linear or branched alkylene, alkylenecycloalkylene or cycloalkylenealkylene radical which has at least 15 C atoms and which is interrupted by one or two --COO--, --OOC--, --CONH-- and/or --NHCO-- groups, and Z is hydrogen, hydroxyl or a --COOH group.Perylene diimides of this type are excellently suitable for coloring polyolefins. In this regard, they are particularly distinguished by their low tendency to bloom. They are also very suitable for coloring engineering plastics, in which they produce fluorescent colorations having a high fluorescence and excellent fastness to heat, light and weathering.
    Type: Grant
    Filed: September 24, 1990
    Date of Patent: April 14, 1992
    Assignee: Ciba-Geigy Corporation
    Inventor: Fridolin Babler
  • Patent number: 5097027
    Abstract: Heterocyclic compounds of the formula ##STR1## are used as pigments for surface coatings and for coloring and pigmenting high molecular weight organic material.
    Type: Grant
    Filed: October 5, 1990
    Date of Patent: March 17, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventor: Hans Hochstetter
  • Patent number: 5095103
    Abstract: Heterocyclic compounds of the formula ##STR1## with the substituent meanings given in the description, and derivatives thereof are suitable for dyeing and pigmenting the most diverse substrates.
    Type: Grant
    Filed: December 12, 1990
    Date of Patent: March 10, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventor: Hans Hochstetter
  • Patent number: 5013627
    Abstract: Positively charged electrophotographic toners contain, besides customary resin and pigment particles, an additive which increases the cationic charge and has the general formula(X.sup.1).sup.- K.spsp.+.sup.1 -Y.sup.1 -A-Y.sup.2 -K.spsp.+.sup.2 (X.sub.2).sup.- (I)wherein the symbols have the meaning mentioned in the description.
    Type: Grant
    Filed: August 7, 1989
    Date of Patent: May 7, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Horst Harnisch, Roderich Raue
  • Patent number: 4978755
    Abstract: Perylene-3,4,9,10-tetracarboxylic acid diimides of the formula I ##STR1## in which R is a linar or branched alkylene, alkylenecycloalkylene or cycloalkylenealkylene radical which has at least 15 C atoms and which is interrupted by one or two --COO--, --OOC--, --CONH-- and/or --NHCO-- groups, and Z is hydrogen, hydroxyl or a --COOH group.Perylene diimides of this type are exellently suitable for coloring polyolefins. In this regard, they are particularly distinguished by their low tendency to bloom. They are also very suitable for coloring engineering plastics, in which they produce fluoroescent colorations having a high fluoroescence and excellent fatness to heat, light and weathering.
    Type: Grant
    Filed: July 24, 1989
    Date of Patent: December 18, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Fridolin Babler
  • Patent number: 4846892
    Abstract: A tetrachloroperylene-3,4,9,10-tetracarboxylic acid diimide pigment which contains not less than 85% by weight of the tetrachloro compound of the formula ##STR1## which is present to the extent of not less than 95% by weight in the .beta.-modification and which, in an X-ray spectrum, exhibits 2.sup..crclbar. CuK.sub..alpha. main lines at 9.0.degree., 13.3.degree., 15.0.degree., 16.8.degree., 19.1.degree., 21.5.degree., 24.2.degree., 25.4.degree., 26.5.degree., 27.0.degree. and 27.5.degree..In finishes, the pigment gives very brilliant colorations which are very highly lightfast and fast to weathering and which, upon weathering, neither bleach nor darken up.
    Type: Grant
    Filed: September 3, 1987
    Date of Patent: July 11, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Georg Henning, Erwin Hahn, Peter Hauser, Manfred Patsch
  • Patent number: 4845223
    Abstract: The novel compounds of the general formula ##STR1## where R.sup.1 and R.sup.2 are identical or different aliphatic, cycloaliphatic, aromatic or heterocyclic radicals which are free of groups which impart water solubility,X, Y and Z are each chlorine, bromine or a radical OR.sup.3 andR.sup.3 is unsubstituted or substituted phenyl, naphthyl or anthryl,are very useful as fluorescent dyes in organic material.
    Type: Grant
    Filed: December 8, 1986
    Date of Patent: July 4, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Guenther Seybold, Andreas Stange
  • Patent number: 4831140
    Abstract: Process for the preparation of compounds of the formula (1) ##STR1## in which R.sub.1 denotes a phenyl or naphthyl radical which can be substituted by alkyl, cycloalkyl, alkoxy, aryloxy, arylazo or nitro groups or halogen atoms, and R.sub.2 denotes a hydrogen atom or a phenyl or naphthyl radical which can be substituted by alkyl, cycloalkyl, alkoxy, aryloxy, arylazo or nitro groups or halogen atoms, or denotes an alkyl (C.sub.1 -C.sub.8) radical, by condensation, at between 100.degree. C. and 300.degree. C., of perylene-3,4,9,10-tetracarboxylic dianhydride or a monoanhydride monoimide of the formula (2) ##STR2## in which R.sub.2 has the abovementioned meaning, with an arylamine of the formula (3)R.sub.1 --NH.sub.2 (3)in which R.sub.1 has the abovementioned meaning, in the presence of dialkylamines of the formula (4) ##STR3## in which R' and R" denote straight-chain alkyl .sub.C.sbsb.1.sub.- C.sbsb.6 or branched alkyl .sub.C.sbsb.3.sub.-C.sbsb.6 or cycloalkyl .sub.C.sbsb.5.sub.-C.sbsb.
    Type: Grant
    Filed: April 11, 1986
    Date of Patent: May 16, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ernst Spietschka, Helmut Troster
  • Patent number: 4797162
    Abstract: A process for the preparation of perylene-3,4,9,10-tetracarboxylic acid N,N'-dimethylimide in a high-hiding pigmentary form and a pure red shade, in which a finely divided, dry perylene-3,4,9,10-tetracarboxylic acid, N,N'-dimethylimide prepigment which is prepared in a conventional manner and has a crystallite size of <400 .ANG. is treated with an organic solvent which is liquid in the treatment temperature range stated below and is selected from the series comprising saturated aliphatic brominated or chlorinated hydrocarbons, aromatic hydrocarbons and aromatic brominated or chlorinated hydrocarbons, in a mill or a disperser at temperatures from 0.degree. C. to 100.degree. C., the organic solvent is then distilled off and the perylene-3,4,9,10-tetracarboxylic acid N,N'-dimethylimide pigment is isolated.
    Type: Grant
    Filed: July 8, 1986
    Date of Patent: January 10, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ernst Spietschka, Manfred Urban
  • Patent number: 4769460
    Abstract: Process for preparing perylenetetracarbimide mix-crystal pigments in the crystal lattice of the .alpha.-modification of the N,N'-bis-3',5'-dimethylphenylperylenetetracarbimide of the formula (1) comprising essentially symmetrical N,N'-bis-3',5'-dimethylphenylperylenetetracarbimide of the formula (1) and at least one asymmetrically substituted diimide of the formula (2) in which R stands for methyl or ethyl ##STR1## by condensing 1 mole of perylenetetracarboxylic dianhydride with an excess of up to 30 moles of 3,5-dimethylaniline which contains in total 0.5-6 percent by weight of 4-ethoxyaniline, and their use for coloring organic polymers.
    Type: Grant
    Filed: January 20, 1988
    Date of Patent: September 6, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ernst Spietschka, Helmut Troster
  • Patent number: 4746741
    Abstract: Multi-active photoconductive insulating elements which are sensitive in the far red region of the spectrum are comprised of a charge-generation layer and a charge-transport layer in electrical contact therewith and contain, as the charge-generating agent within the charge-generation layer, the compound N,N'-bis[2-(3-methylphenyl)ethyl]perylene-3,4:9,10-bis(dicarboximide). The charge-generation layer is capable, upon exposure to activating radiation, of highly effective generation and injection of charge carriers and the charge-transport layer, which is comprised of an organic composition containing an organic photoconductive material, is capable of accepting and transporting the injected charge carriers to thereby form a highly advantageous multi-active photoconductive insulating element.
    Type: Grant
    Filed: August 14, 1987
    Date of Patent: May 24, 1988
    Assignee: Eastman Kodak Company
    Inventors: William J. Staudenmayer, Michael T. Regan
  • Patent number: 4742170
    Abstract: Perylenetetracarbimide mix-crystal pigments in the crystal lattice of the .alpha.- Modification of N,N'-bis-3',5'-dimethylphenylperylenetetracarbimide of the formula (1) comprising 98-70 mole percent of the symmetrical diimide of the formula (1) and correspondingly 2-30 mole percent of at least one asymmetrical diimide of the formula (2) ##STR1## in which R denotes a hydrogen atom or a methyl group.
    Type: Grant
    Filed: October 1, 1985
    Date of Patent: May 3, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ernst Spietschka, Helmut Troster
  • Patent number: 4725690
    Abstract: A novel perylene-3,4,9,10-tetracarboxylic acid diimide of the formula ##STR1## is very useful as a black dye or, together with white pigments, as a gray dye.
    Type: Grant
    Filed: June 20, 1986
    Date of Patent: February 16, 1988
    Assignee: BASF Aktiengesellschaft
    Inventor: Fritz Graser
  • Patent number: 4709029
    Abstract: Compounds of the formula ##STR1## in which R denotes hydrogen, hydroxyl, amino or optionally substituted alkyl, X denotes chlorine or bromine and n is a number from zero to 4, are obtained from the corresponding mono-alkali metal salts of perylene-3,4,9,10-tetracarboxylic acid monoanhydrides by reaction with compounds of the formula R-NH.sub.2, in which R has the above meaning, at 0.degree.-130.degree. C. The compounds are colorants or starting materials for colorants.
    Type: Grant
    Filed: January 23, 1986
    Date of Patent: November 24, 1987
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ernst Spietschka, Helmut Troster
  • Patent number: 4667036
    Abstract: Light is concentrated in plastic sheets by a method in which the fluorescent centers used are perylenetetracarboxylic acid diimides of the formula ##STR1## The compounds (I) are prepared by chlorinating (I) in which n is 0 with sulfuryl chloride in an inert organic liquid in the presence of a catalyst. In the formula, n is 2, 3, 4 or 5 or 6, and R and R.sup.1 independently of one another are each (a) straight-chain or branched C.sub.1 -C.sub.18 -alkyl which is unsubstituted or substituted by cyano, hydroxyl, cycloalkyl, alkylcarbonyloxy, alkenylcarbonyl-oxy or cycloalkylcarbonyloxy and in which the alkyl chain may furthermore be interrupted by O or S, or (b) C.sub.5 -C.sub.18 -cycloalkyl which is unsubstituted or substituted by alkyl, carboalkoxy or trifluoromethyl.Novel perylenetetracarboxylic acid diimides of the formula I, where n is 4 and R and R.sup.
    Type: Grant
    Filed: August 20, 1984
    Date of Patent: May 19, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Ruediger Iden, Guenther Seybold
  • Patent number: 4613667
    Abstract: Silane diimidic tetracarboxylic perylene dyes, the composite pigments obtainable therefrom by means of grafting onto an inorganic substrate, and the processes for preparing same.The dyes have the general formula: ##STR1## in which R is the residue of a silane group of formula: ##STR2## in which n is 3, 4 or 5; q is 0 or 1, p and m are such integers than when q is 0, p is 3 and m is 0, 1, 2 or 3, and when q is 1, p is 2 and m is 0, 1 or 2; R.sub.2 is an alkyl C.sub.1 -C.sub.4 or a phenyl; R.sub.3 is an alkoxyl C.sub.1 -C.sub.2 ; R.sub.1 may be the same as R or represent an alkyl C.sub.1 -C.sub.6, a cycloalkyl, a phenyl optionally substituted by one or more alkyl or alkoxyl groups C.sub.1 -C.sub.6 or a halogen.The dyes and the composite pigments obtained from said dyes are utilized in paints, air and stove enamels, in the pigmentation of plastic materials, and in printing inks.
    Type: Grant
    Filed: October 22, 1984
    Date of Patent: September 23, 1986
    Assignee: Montedison S.p.A.
    Inventors: Antonio Marraccini, Filippo M. Carlini, Giorgio Bottaccio, Antonio Pasquale, Giorgio Maranzana
  • Patent number: 4607097
    Abstract: A dichromatic coloring matter for a colored liquid crystal display element comprising a compound of the general formula: ##STR1## where A and B each stand for ##STR2## where n is 0, 1, 2, 3 or 4, and X and Y each stand for ##STR3## where R.sub.1 and R.sub.2 stand for an alkyl group or hydrogen, --R (alkyl group) or --OR (alkoxy group).
    Type: Grant
    Filed: June 4, 1984
    Date of Patent: August 19, 1986
    Assignees: Alps Electric Co., Ltd., Sanyo Color Works Ltd.
    Inventors: Mitsuru Kano, Yoshinori Kato, Yoshimi Kamijo, Yoshio Takeda, Yoshinari Sakikubo, Naoki Yagi
  • Patent number: 4599408
    Abstract: Compounds of the formula ##STR1## in which R denotes hydrogen, hydroxyl, amino or optionally substituted alkyl, X denotes chlorine or bromine and n is a number from zero to 4, are obtained from the corresponding mono-alkali metal salts of perylene-3,4,9,10-tetracarboxylic acid monoanhydrides by reaction with compounds of the formula R--NH.sub.2, in which R has the above meaning, at 0.degree.-130.degree. C. The compounds are colorants or starting materials for colorants.
    Type: Grant
    Filed: April 11, 1984
    Date of Patent: July 8, 1986
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ernst Spietschka, Helmut Troster
  • Patent number: 4597891
    Abstract: There are described novel perylene dyes which have at least one, and preferably two, substituted twisted biphenylene radicals. The substituted biphenylene radicals include substituents which confer a non-coplanar molecular configuration about the long axis of the dye molecule. The dyes are soluble in various liquid crystal materials and exhibit a high order parameter in solutions of liquid crystal material. Also disclosed are liquid crystal compositions and liquid crystal devices.
    Type: Grant
    Filed: June 4, 1984
    Date of Patent: July 1, 1986
    Assignee: Polaroid Corporation
    Inventors: Howard G. Rogers, Russell A. Gaudiana, Cynthia B. McGowan, Kenneth S. Norland, Ronald J. Sahatjian
  • Patent number: 4594420
    Abstract: Compounds of the formula ##STR1## wherein X denotes a chlorine or bromine atom, n denotes a number from zero to 4 and Y denotes an oxygen atom or a nitrogen atom, and A, if Y represents an oxygen atom, is the phenyl radical, which can be substituted by substituents from the group comprising halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, carbalkoxy with 1-4 carbon atoms in the alkyl radical, hydroxyl, carboxyl, CF.sub.3, nitro, phenoxy, phenoxy which is substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy and/or halogen, phenylamino, phenylamino which is substituted in the phenyl radical by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy and/or halogen, phenylazo and phenylazo which is substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -akloxy and/or halogen, or is the pyridyl radical, which can be substituted by halogen and/or C.sub.1 -C.sub.
    Type: Grant
    Filed: March 12, 1984
    Date of Patent: June 10, 1986
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ernst Spietschka, Helmut Troster
  • Patent number: 4588814
    Abstract: Preparation of 3,4,9,10-perylenetetracarboxylic acid diimide by fusing naphthalene-1,8-dicarboxylic acid imide with potassium hydroxide and sodium acetate to give the alkali metal salt of the leuko compound of 3,4,9,10-perylenetetracarboxylic acid diimide, diluting the melt with water when the reaction has ended and oxidizing the leuko form to give the 3,4,9,10-perylenetetracarboxylic acid diimide, by a procedure which comprises(a) applying a vacuum of less than 100 mm Hg before the naphthalene-1,8-dicarboxylic acid imide is introduced into the potassium hydroxide/sodium acetate melt, heating the potassium hydroxide/sodium acetate mixture to 200.degree.-300.degree. C. and dehydrating it such that the melt is still stirrable at 200.degree.-220.degree. C., and then introducing the naphthalene-1,8-dicarboxylic acid imide or its sodium or potassium salt into the melt at 200.degree.-220.degree. C. under normal pressure and heating the mixture at 250.degree.-300.degree. C.
    Type: Grant
    Filed: April 19, 1984
    Date of Patent: May 13, 1986
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ernst Spietschka, Manfred Urban
  • Patent number: 4501906
    Abstract: Perylene-3,4,9,10-tetracarboxylic acid monoanhydride mono-sodium or mono-potassium salts are obtained from neutral salts of perylene-3,4,9,10-tetracarboxylic acid, if necessary in the presence of at least one molar equivalent of sodium or potassium ions, at 20.degree. to 100.degree. C. by adding three molar equivalents of a sufficiently strong acid. The products are dye precursors, especially for asymmetric N-substituted perylenetetracarboxylic acid diimide pigments.
    Type: Grant
    Filed: February 10, 1983
    Date of Patent: February 26, 1985
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ernst Spietschka, Helmut Troster
  • Patent number: 4496731
    Abstract: The invention relates to a process for the preparation of perylene-3,4,9,10-tetracarboxylic acid N,N'-dialkyldiimides by reacting perylene-3,4,9,10-tetracarboxylic acid dianhydride with an alkylamine in aqueous suspension at a low temperature, in the course of which the bis-(alkylammonium) salt of perylene-3,4,9,10-tetracarboxylic acid bis-N-alkylamide is formed. The latter is reacted with a metal salt to give the corresponding sparingly soluble metal salt, which is subjected to the cyclization reaction at an elevated temperature. The pigments prepared by the process according to the invention are distinguished by high purity and are suitable for pigmenting lacquers and plastic compositions.
    Type: Grant
    Filed: February 24, 1983
    Date of Patent: January 29, 1985
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ernst Spietschka, Manfred Urban
  • Patent number: 4492648
    Abstract: Light-collecting system, characterized in that it contains a dyestuff of the formula ##STR1## in which Hal designates identical or different halogen atoms from the series comprising fluorine, chlorine and bromine,R.sub.1 and R.sub.2 designate hydrogen or optionally substituted C.sub.1 -C.sub.18 -alkyl and n designates 4-5,and new dyestuffs of the formula I which in a 0.5-2 mM solution in path lengths of 10 cm display an increase in transmission from 0 to >95% with a change in the wavelength of 25-120 nm.
    Type: Grant
    Filed: December 7, 1982
    Date of Patent: January 8, 1985
    Assignee: Bayer Aktiengelsellschaft
    Inventor: Uwe Claussen
  • Patent number: 4451398
    Abstract: Dyes of the formula ##STR1## where R.sup.1 is hydrogen, C.sub.1 -C.sub.6 -alkyl or C.sub.2 -C.sub.6 -alkenyl, R.sup.2 and R.sup.3 independently of one another are hydrogen, C.sub.1 -C.sub.5 -alkyl or C.sub.2 -C.sub.5 -alkenyl, R.sup.4 is C.sub.1 -C.sub.12 -alkyl or hydroxy-C.sub.2 -C.sub.4 -alkyl, X.sup..crclbar. is one equivalent of an anion, mis from 0 to 5 and n is from 0 to 5, with 1.ltoreq.(m+n).ltoreq.5, and F is an (m+n)-valent radical of a monoazo dye, a disazo dye, a polyazo dye, a quinophthalone, a bis-dioxazine, a compound of the 5,6-arylo-2-pyrone series, a naphtholactam dye, a triphenylmethane dye, a xanthene dye, a phthalocyanine, an indigoid, an anthraquinone dye containing one or more phenyl or naphthyl groups, a more highly fused carbonyl-containing dye, a quinacridone, a perylene-3,4,9,10-tetracarboxylic acid diimide, an anthrapyrimidine, a pyrazoloanthrone, a diaminonaphthoquinone, a naphthazarine or a naphthalene-1,4,5,8-tetracarboxylic acid diimide.
    Type: Grant
    Filed: February 11, 1981
    Date of Patent: May 29, 1984
    Assignee: BASF Aktiengesellschaft
    Inventors: Manfred Patsch, Manfred Ruske
  • Patent number: 4450273
    Abstract: A perylene-3,4,9,10-tetracarboxylic acid diimide of the formula ##STR1## gives black colorations with excellent lightfastness and weathering fastness, in polyethylene, PVC, surface coatings, inks and aqueous dye formulations.
    Type: Grant
    Filed: January 6, 1982
    Date of Patent: May 22, 1984
    Assignee: BASF Aktiengesellschaft
    Inventor: Fritz Graser
  • Patent number: 4446324
    Abstract: Novel perylene-3,4,9,10-tetracarboxylic acid diimides of the formula ##STR1## where R.sup.1 and R.sup.2 are each isopropyl or R.sup.1 is methyl or ethyl and R.sup.2 is C.sub.3 - or C.sub.4 -alkyl, give clear, luminous, very lightfast, fluorescent orange colorations in plastics.The dyes are particularly suitable for concentrating light.
    Type: Grant
    Filed: December 9, 1981
    Date of Patent: May 1, 1984
    Assignee: BASF Aktiengesellschaft
    Inventor: Fritz Graser
  • Patent number: 4431806
    Abstract: Very pure, transparent pigments of high color strength, of the formula ##STR1## in which R is hydrogen or alkyl having 1 to 4 C atoms, X is chlorine and/or bromine and n is a number from 0 to 4 are obtained by converting the corresponding crude pigment to the sulfate, isolating the sulfate, liberating the pure product from the sulfate by hydrolysis, separating off the pure product and dry milling the anhydrous material, with or without additives and with or without subsequent solvent finishing. These pigments are suitable for coloring paints and plastic compositions, especially for pigmenting metallic paints.
    Type: Grant
    Filed: May 8, 1981
    Date of Patent: February 14, 1984
    Assignee: Hoechst A.G.
    Inventors: Ernst Spietschka, Manfred Urban
  • Patent number: 4404385
    Abstract: Perylenetetracarboxylic acid-bis-(3,5-dimethylphenyl)imide in a novel .gamma.-modification characterized by an X-ray diffraction spectrum exhibiting very strong lines at interplanar spacings of 8.3, 3.61, 3.46 and 3.30 A, and strong lines at interplanar spacings of 17.2, 10.3, 7.2, 6.7 and 4.09.The pigment is suitable for dyeing high-molecular organic material. Compared with the known yellowish-red modifications, the .gamma.-modification is characterized by a bluish-red shade.
    Type: Grant
    Filed: June 23, 1980
    Date of Patent: September 13, 1983
    Assignee: Ciba-Geigy Corporation
    Inventor: Fridolin Babler
  • Patent number: 4404386
    Abstract: Process for the preparation of opaque perylenetetracarboxylic acid bis-(3,5-dimethylphenylimide), which comprises heating the .alpha.-modification of perylenetetracarboxylic acid bis-(3,5-dimethylphenylimide) in at least one aliphatic monocarboxylic acid. Use as a pigment for plastic compositions, printing inks, fibres and paints.
    Type: Grant
    Filed: June 12, 1981
    Date of Patent: September 13, 1983
    Assignee: Ciba-Geigy Corporation
    Inventor: Fridolin Babler