Plural Hetero Atoms In The Six-membered Hetero Ring Patents (Class 540/125)
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Patent number: 5516899Abstract: A phthalocyanine of Formula (1): ##STR1## wherein: M.sub.k PC iS a phthalocyanine nucleus of Formula (2): ##STR2## M is a metal atom, a chloro-metal group, and oxy-metal group or hydrogen; k is inverse of 1/2 valency of M;R and R.sup.1 each independently is an organic radical;R.sup.2 is H or optionally substituted alkyl;a is an average value from 15 to 8;b is an average value from 1 to 8; anda+b is from 15 to 16; and sulphonated derivatives thereof and process for their preparation.The phthalocyanines of the present invention are useful for absorbing electro-magnetic radiation from for example a laser source and may be used in a coating for optical data storage disks, or in security applications such as printing banknotes or checks, or in the preparation of lithographic printing plates or in washing powders to assist in bleaching.Type: GrantFiled: July 20, 1994Date of Patent: May 14, 1996Assignee: Zeneca LimitedInventors: James S. Campbell, Peter Gregory, Dean Thetford
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Patent number: 5484778Abstract: The present invention relates to a series of novel phthalocyanine compositions (or compounds) suitable for use as photosensitizers for photodynamic therapy. Specifically, the invention relates to a series of new aluminum (Al) germanium (Ge), gallium (Ga), tin (Sn) and/or silicon (Si) phthalocyanines having substituted amine or quaternary ammonium axial ligands attached to the central metal, and the use of these new phthalocyanine compositions for the treatment of cancer through photosensitization. Moreover, the present invention is directed to the methods of preparing these compositions for use in photodynamic therapy.Type: GrantFiled: September 2, 1993Date of Patent: January 16, 1996Assignee: University Hospitals of ClevelandInventors: Malcolm E. Kenney, Nancy L. Oleinick, Boris D. Rihter, Ying-Syi Li
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Patent number: 5444163Abstract: There is described a process for preparing reactive phthalocyanine dyes with .beta.-substituted ethylsulfonyl or vinylsulfonyl groups by reacting a phthalocyaninesulfonyl chloride with amines with .beta.-substituted ethylsulfonyl or vinylsulfonyl groups with or without further amines in the presence of a heterocyclic catalyst.Type: GrantFiled: November 12, 1993Date of Patent: August 22, 1995Assignee: BASF AktiengesellschaftInventors: Juergen Dornhagen, Manfred Patsch
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Patent number: 5427616Abstract: A process for the production of a copper phthalocyanine pigment composition from 70 to 99% by weight of a crude copper phthalocyanine and 30 to 1% by weight of a phthalocyanine derivative,the crude copper phthalocyanine being converted to a pigment without a large amount of energy and the treatment of exhaust water,the copper phthalocyanine pigment composition having excellent fluidity, tinting strength and stability with time when used in a coating composition or a printing ink,the copper phthalocyanine pigment composition showing almost no "strike-through" when used for gravure printing on low-quality paper,the process comprising dry milling the entirety of the crude copper phthalocyanine and the phthalocyanine derivative in an amount of 0.5 to 10% by weight of a final composition in the absence of a milling auxiliary until the content of an .alpha.Type: GrantFiled: June 1, 1994Date of Patent: June 27, 1995Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Kosaku Tsuji, Yoshio Muramatsu, Shigeki Kato
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Patent number: 5420255Abstract: A process for the continuous reaction of halogenopyrimidines with amines, a halogenopyrimidine and an aqueous amine solution or suspension being passed into a reactor and the reaction product being subsequently conducted away, is described, characterized in that the starting materials are introduced into the reactor simultaneously and continuously with intensive mixing.Type: GrantFiled: February 22, 1994Date of Patent: May 30, 1995Assignee: Bayer AktiengesellschaftInventors: Siegbert Arnold, Hans-Georg Frosch, Manfred Hoppe, Wolfgang Mullers, Richard Sommer
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Patent number: 5399674Abstract: Fiber-reactive dyestuffs, processes for their preparation and their useDyestuffs of the formula (1) are described ##STR1## The dyestuffs have fiber-reactive properties and dye materials containing hydroxy groups and/or containing carboxamide groups, in particular fiber materials, such as, for example, cellulose fibers, wool and synthetic polyamide fibers, in deep, fast shades by the methods known for this process.Type: GrantFiled: December 3, 1993Date of Patent: March 21, 1995Assignee: Hoechst AktiengesellschaftInventors: Jorg Dannheim, Werner H. Russ
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Patent number: 5378817Abstract: Reactive dyestuffs of the formula ##STR1## wherein Z=a heterocyclic reactive group and the remaining groups have the meaning given in the description, are outstandingly suitable for dyeing and printing materials containing hydroxyl groups or amide groups.Type: GrantFiled: January 15, 1993Date of Patent: January 3, 1995Assignee: Bayer AktiengesellschaftInventors: Konrad Bootz, Karl-Josef Herd
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Patent number: 5342927Abstract: Reactive dyestuffs of the formula ##STR1## in which X is ##STR2## and Z is a heterocyclic reactive group and the remaining groups have the meaning given in the description, are highly suitable for the dyeing and printing of hydroxyl- or amido-containing materials.Type: GrantFiled: July 21, 1992Date of Patent: August 30, 1994Assignee: Bayer AktiengesellschaftInventors: Wolfram Reddig, Karl-Josef Herd
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Patent number: 5322760Abstract: A nonlinear optical element comprising a tetraazaporphyrin compound represented by the formula (I): ##STR1## This nonlinear optical element is excellent in that it is improved over low switching speed of the conventional inorganic materials and over small nonlinearity and poor chemical and physical stability and workability of the conventional organic materials.Type: GrantFiled: November 29, 1991Date of Patent: June 21, 1994Assignee: Hitachi, Ltd.Inventors: Yuzo Itoh, Atsushi Kakuta, Akio Mukoh
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Patent number: 5302708Abstract: Phthalocyanine dyes, in particular copper phthalocyanine and nickel phthalocyanine dyes which contain one or more groups of the formula given and defined below ##STR1## or one or more carboxy groups or both groups and which furthermore can contain one or more sulfo groups, customary sulfonamide groups and/or groups of the formula given and defined below ##STR2## dye hydroxy- and/or carboxamide-containing materials, in particular fiber materials, such as cellulose fiber materials, wool and polyamide fibers, in fast, predominantly green hues of high color strength.Type: GrantFiled: August 6, 1992Date of Patent: April 12, 1994Assignee: Hoechst AktiengesellschaftInventors: Thomas Beck, Werner H. Russ, Hartmut Springer, Marcus Banfer
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Patent number: 5284943Abstract: Special tetraazaporphins containing Si, Ge or Sn as the central metal are useful for forming a recording layer in an optical recording medium.Type: GrantFiled: January 22, 1992Date of Patent: February 8, 1994Assignee: Hitachi Chemical Company, Co.Inventors: Seiji Tai, Nobuyuki Hayashi, Koichi Kamijima, Mitsuo Katayose, Takayuki Akimoto, Hideo Hagiwara
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Patent number: 5279622Abstract: Solid dyestuff preparations of reactive phthalocyanine dyestuffs of the formula ##STR1## in which the substituents have the meaning given in the description, have improved solubility in water if they contain 5 to 15% by weight of an acid-binding agent.Type: GrantFiled: April 28, 1992Date of Patent: January 18, 1994Assignee: Bayer AktiengesellschaftInventors: Josef-Walter Stawitz, Frank-Michael Stohr, Joachim Wolff
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Patent number: 5217856Abstract: Special tetraazaporphins containing Si, Ge or Sn as the central metal are useful for forming a recording layer in an optical recording medium.Type: GrantFiled: April 6, 1989Date of Patent: June 8, 1993Assignee: Hitachi Chemical Co., Ltd.Inventors: Seiji Tai, Nobuyuki Hayashi, Koichi Kamijima, Mitsuo Katayose, Takayuki Akimoto, Hideo Hagiwara
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Patent number: 5189153Abstract: A phthalocyanine compound of the Formula (1): ##STR1## wherein: Pc is a phthalocyanine nucleus which is metal free or contains a metal or oxymetal;X is S; NT or O;Y is S; NT or O;Z is S or Se; in which T in the above is H; alkyl or aryl;.sup.+ HA is an aliphatic polyamino ammonium ion or a substituted diguanidinium ion;each R independently is an aromatic radical linked to a peripheral carbon atom of the Pc nucleus through an atom Z;each R.sup.1 independently is optionally substituted phenylene or naphthylene in which the atoms X and Y are attached to adjacent nuclear carbon atoms in R.sup.1 and to adjacent peripheral carbon atoms of the Pc nucleus;a is 0 to 16; provided thatb is 0 to 8; a+b>0; andc+d is 1 to 16.Type: GrantFiled: June 19, 1990Date of Patent: February 23, 1993Assignee: Imperial Chemical Industries, PLCInventors: Peter Gregory, Prakash Patel
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Patent number: 5189154Abstract: Anionic phthalocyanine compounds which, in the free acid form, have the Formula (1):Pc(SO.sub.3 H).sub.t (SO.sub.2 --NR.sup.1 --L--NR.sup.2 --X--NR.sup.3 --G).sub.q (1)The compounds are useful as the colored component of inks, particularly those used in ink jet printing.Type: GrantFiled: June 28, 1991Date of Patent: February 23, 1993Assignee: Imperial Chemical Industries PLCInventors: Peter Gregory, Ronald W. Kenyon, Christine Millard
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Patent number: 5126443Abstract: Compounds of the formulae ##STR1## salts thereof, and mixtures of such compounds or salts,wherein Me, Pc, Q.sub.1, R.sub.1, R.sub.2, R.sub.3, Y, a, b, c and d as defined,useful as fiber-reactive dyes for dyeing or printing hydroxy group- and nitrogen-containing organic substrates, for example, textile material comprising cotton, the obtained dyeings and prints having good all-round fastnesses, such as good light fastness.Type: GrantFiled: September 19, 1990Date of Patent: June 30, 1992Assignee: Sandoz Ltd.Inventors: Helmut A. Moser, Roland Wald
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Patent number: 5070193Abstract: Novel reactive dyestuffs of the formula ##STR1## having the substituent meanings specified in the description are highly suitable for dyeing and printing hydroxyl- and amido-containing textile materials. They produce very fast dyeings and prints in high yields.Type: GrantFiled: December 14, 1989Date of Patent: December 3, 1991Assignee: Bayer AakatiengesellschaftInventors: Karl H. Schundehutte, Manfred Groll, Josef W. Stawitz
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Patent number: 5059681Abstract: A water-soluble reactive dye of the formula: ##STR1## wherein D represents a radical of a water-soluble azo dye selected from: (i) sulphonated monoazo radicals which are free from complexly bound metal and have the formula: ##STR2## wherein A represents a radical of the benzene or naphthalene series, R.sup.3 represents hydrogen or C.sub.1-8 -alkyl and one of U and V is SO.sub.3 H, the other being H, and(ii) a disazo radical of the formula: ##STR3## x represents Cl, Br, F, SO.sub.3 H or a quaternary ammonium group; R.sup.1 represents an optionally substituted C.sub.1-8 -alkyl radical; R.sup.2 represents hydrogen or an optionally substituted C.sub.1-8 -alkyl radical; andT represents a 1,3- or 1,4-phenylene radical which may carry one or more substituents selected from halogen, alkyl, alkoxy, acylamino, nitro and carboxy.Type: GrantFiled: February 1, 1990Date of Patent: October 22, 1991Assignee: Imperial Chemical Industries plcInventor: John A. Taylor
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Patent number: 5051501Abstract: Novel reactive dyestuffs of the formula ##STR1## wherein Pc=radical of a Cu- or Ni-phthalocyanine,R.sub.1, R.sub.2 =H, C.sub.1 -C.sub.4 -alkyl optionally substituted with --OH, --COOH, --OSO.sub.3 H or --SO.sub.3 H, or together C.sub.2 -alkylene,B=C.sub.2 -C.sub.6 -alkylene or phenylene optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, nitro, cyano, COOH, SO.sub.3 H, carboxanide, sulphonamide, C.sub.1 -C.sub.4 -alkylcarbonylamino or --NHCONH.sub.2,R.sub.3, R.sub.4 =H, C.sub.1 -C.sub.4 -alkyl optionally substituted with OH, --COOH, --OSO.sub.3 H or --SO.sub.3 H, or optionally sulphur- or carboxyl-substituted phenyl, or together C.sub.2 -alkylene,a=1.0 to 2.7,b=0.8 to 1.2, andc=0.5 to 1.5, where a+b+c=3 to 4.Type: GrantFiled: November 6, 1989Date of Patent: September 24, 1991Assignee: Bayer AktiengesellschaftInventors: Karl H. Schundehutte, Manfred Groll, Josef W. Stawitz
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Patent number: 5032495Abstract: An optical recording medium contains tetraazaporphyrins of the formula ##STR1## where L.sup.1, L.sup.2, L.sup.3 and L.sup.4 are each independently of the others the radical of a bicyclic aromatic heterocycle containing 1 to 3 identical or different heteroatoms selected from the group consisting of N, O and S, which may be substituted, andR.sup.1 and R.sup.2 have defined meanings.Type: GrantFiled: August 18, 1989Date of Patent: July 16, 1991Assignee: BASF AktiengesellschaftInventors: Bernhard Albert, Peter Neumann, Rolf-Dieter Kohler
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Patent number: 4978747Abstract: Colorants are obtained by reacting a dyestuff which is free from ionic groups and has.gtoreq.2 NH.sub.2 groups which are preferably arranged in such a manner that they do not participate in the resonance of the chromophore with such an amount of a (cyclo)aliphatic diisocyante so as to form an adduct that still contains at least two free NCO groups, and subsequently reacting this adduct with a (cyclo)aliphatic diamine, to form an adduct suitable for dyeing and pigmenting macromolecular substances, in particular for coloring PUR-based paints, coatings and laminates.Type: GrantFiled: April 13, 1989Date of Patent: December 18, 1990Assignee: Bayer AktiengesellschaftInventors: Karl-Arnold Weber, Hermann Henk, Klaus Kunde, Jochen Westphal, Klaus Wunderlich
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Patent number: 4845209Abstract: The invention relates to phthalocyanine compounds of the formula ##STR1## wherein MePc is a copper, cobalt or nickel phthalocyanine radical,R.sub.1 is hydrogen or alkyl,X is alkylene, andR.sub.2, R.sub.3 and R.sub.4, are each independently alkyl which is unsubstituted or substituted by hydroxy, alkoxy, phenyl or amino, or R.sub.1 and R.sub.2, when taken together, are methylene, ethylene or propylene if X is methylene or ethylene, or two or three of R.sub.2, R.sub.3 and R.sub.3, together with the nitrogen atom, form a 5- to 7-membered unsubstituted or substituted heterocyclic ring which may contain one or two additional hetero atoms selected from the group consisting of O, N and S as ring members,An.sup..crclbar. is a cation and M is a cation, and x is greater than y and y is greater than 0, and the sum of x+y is 4 or less than 4.These compounds can be used as dyes, in particular for dyeing and printing cellulosic materials and polyacrylonitrile materials, especially paper.Type: GrantFiled: August 4, 1988Date of Patent: July 4, 1989Inventor: Jean-Marie Adam
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Patent number: 4824947Abstract: A phthalocyanine compound of the formula: ##STR1## wherein Pc is a phthalocyanine nucleus;each R independently is optionally substituted phenyl;m is 4 to 12;V is H or C.sub.1-4 -alkyl;each R.sup.1 independently is optionally substituted phenylene or naphthylene in which the S atom and group N-V are attached to adjacent nuclear carbon atoms;and n is 2 to 6;provided that R is not R.sup.1 -NHV.The compounds have a significant absorption band in the near infra red and are soluble in non-polar organic media. The compounds are useful in many applications where absorption of infra-red radiation is desirable, such as in OCR readable inks, security printing and reprographic toners.Type: GrantFiled: March 1, 1988Date of Patent: April 25, 1989Assignee: Imperial Chemical Industries PLCInventor: William M. Stark
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Patent number: 4824948Abstract: A phthalocyanine compound of the formula:(R--X--).sub.m Pc (--Y--R.sup.1 --Z--).sub.n (--SO.sub.3 M).sub.p IwhereinPc is a phthalocyanine nucleus (Pc);eachR independently is a monovalent aromatic radical linked to a peripheral carbon atom of the Pc nucleus through X;X selected from S, Se and Te;m is 4 to 16;eachR.sup.1 independently is a divalent aromatic radical linked to two adjacent peripheral carbon atoms of the Pc nucleus through Y and Z;Y is selected from S, NT, Se and Te;Z is selected from S, Se, Te, NT and O;T is selected from H, alkyl and aryl;n is 0 to 7;M is H, a metal or optionally-substituted ammonium;andP is from 1 to 16.The compounds have a significant absorption band in the near infra red and depending on the number of sulphonic acids groups and the nature of the counter ion are soluble in aqueous and polar organic media.Type: GrantFiled: March 1, 1988Date of Patent: April 25, 1989Assignee: Imperial Chemical Industries plcInventors: William Stark, Nigel Hughes, Donald M. Gunn
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Patent number: 4786721Abstract: The reactive dyes are useful, in particular, for dyeing or printing cellulose-containing fiber materials by the cold pad-batch method and produce, with a high dyeing yield, dyeings and prints having good fastness properties.Type: GrantFiled: August 13, 1986Date of Patent: November 22, 1988Assignee: Ciba-Geigy CorporationInventors: Athanassios Tzikas, Peter Aeschlimann, Paul Herzig
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Patent number: 4785088Abstract: Pigments of the general formulaF.multidot.Het (I).where F is the cation of a cationic dye which has an absorption maximum at >700 nm and may or may not contain anionic groups and Het is an anion of a heteropolyacid based on tungsten, molybdenum, vanadium or a mixture of these with phosphorus, silicon, cobalt, aluminum, manganese, chromium, nickel or a mixture of these or a copper(I)-hexacyanoferrate(II) anion, are superior to the known IR dyes in terms of thermal stability and photostability, and give optical recording media having superior properties, such as a high signal/noise ratio.Type: GrantFiled: June 4, 1986Date of Patent: November 15, 1988Assignee: BASF AktiengesellschaftInventors: Helmut Flohr, Joachim Jesse, Bernhard Albert, Peter Neumann
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Patent number: 4745187Abstract: Water-soluble phthalocyanine dyestuffs having vinylsulfonyl or .beta.-substituted ethylsulfonyl groups are prepared by reaction of phthalocyanine sulfonyl chlorides, which may contain sulfo groups, with a primary or secondary amine having vinylsulfonyl or .beta.-substituted ethylsulfonyl groups and, if appropriate, with a second primary or secondary amine of the aliphatic, heterocyclic or aromatic series, in the presence of a pyridinesulfonamide or pyridinecarboxamide.Type: GrantFiled: January 29, 1987Date of Patent: May 17, 1988Assignee: Hoechst AktiengesellschaftInventor: Hartmut Springer
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Patent number: 4710569Abstract: Dyestuffs of the formula ##STR1## wherein F stands for an organic chromophore andZ stands for radicals of the formulae ##STR2## wherein R.sub.1 -R.sub.2 denote hydrogen, alkyl, cycloalkyl, alkenyl, aryl, aralkyl or a heterocyclic structure orR.sub.2 and R.sub.3 represent an optionally substituted amino group or together form a ring orR.sub.1 with R.sub.2 and/or R.sub.3 with R.sub.4 form a ring,A.sup.(-) denotes an anion,Y denotes an anionic group,m denotes 0-2 andn denotes 1-6,and wherein the chromophore and said radicals can carry further substituents, provided that the total number of anionic substituents is smaller than the total number of quaternary and quaternizable amino groups, are used for dyeing cellulose fibres, in particular paper.Type: GrantFiled: September 10, 1985Date of Patent: December 1, 1987Assignee: Bayer AktiengesellschaftInventors: Gunter Franke, Dieter Ockelmann, Roderich Raue, Peter Wild
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Patent number: 4665165Abstract: A compound or a mixture of compounds of formula I ##STR1## in which Pc is a phthalocyanine group (which may be metallized or metal-free);R.sub.1 is hydrogen or lower alkyl;Q and Q.sub.1 are both either --NR.sub.2 R.sub.3 or are both --N.sup..sym. R.sub.4 R.sub.5 R.sub.6 A.sub.n.sup..crclbar. where R.sub.2 to R.sub.6 are organic substituents.M is hydrogen or a cation;A is a lower alkylene or a lower alkenylene;A.sub.n.sup..crclbar. is a non-chromophoric anion;m and n are average numbers from 0.3 to 4;p is an average number from 0 to 1;with the provisos that(i) m+n is an average number from 2 to 6; and(ii) Q and Q.sub.1 are not the same group.Type: GrantFiled: May 7, 1986Date of Patent: May 12, 1987Assignee: Sandoz Ltd.Inventor: Roland Wald
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Patent number: 4648992Abstract: Novel phthalocyanine compounds are described, which have the formula ##STR1## in which MePc is the Si(IV)-, P(V)-, Ti(IV)-, Ge(IV)-, Cr(IV)-, Ga(III)-, Zr(IV)-, In(III)-, Sn(IV)- or Hf(IV)- phthalocyanine or -naphthalocyanine ring system, A is an anionic, nonionic or cationic group which imparts solubility in water, Z is the counter-ion to A, if the latter is an ionic group, and is 0 if A is a nonionic group, n is any desired number from 1 to 8, Y is a neutral substituent which does not impart solubility in water and p is any desired number from 0 to 6, it being possible for the groups AZ and Y present in the molecule to be identical or different in either case, and the sum of n+p being not more than 8 and MePc not being the Sn(IV)-phthalocyanine or Sn(IV)-naphthalocyanine ring system if p is 0 and if the only groups imparting water-solubility in the molecule are sulfo groups.Type: GrantFiled: February 11, 1985Date of Patent: March 10, 1987Assignee: Ciba-Geigy CorporationInventors: Gregor Graf, Gerd Holzle, Gerhard Reinert
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Patent number: 4648993Abstract: A compound useful for dyeing acid-modified fibers, having the formula ##STR1## where R.sup.5 is hydrogen, methyl or ethyl; R.sup.2 and R.sup.3 are each methyl, ethyl, .beta.-hydroxyethyl, .beta.-hydroxypropyl or benzyl; A.sup.- is an anion; m is 2 or 3 and n is 0.1 to 1 based on statistical averages.Type: GrantFiled: July 8, 1985Date of Patent: March 10, 1987Assignee: BASF AktiengesellschaftInventors: Horst Colberg, Udo Mayer
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Patent number: 4647409Abstract: Basic copper-phthalocyanine dyestuffs of the formula ##STR1## in which Cu--Pc denotes the radical of an x-valent copper-phthalocyanine,A and B independently of each other denote an alkylene radical having 2 to 5 carbon atoms,R.sub.1 and R.sub.3 independently of each other denote hydrogen or an alkyl radical having 1 to 3 carbon atoms which is optionally substituted by hydroxyl, C.sub.1 - to C.sub.3 -alkoxy, halogen or an NH.sub.2 group,R.sub.2 denotes an alkyl group having 1 to 3 carbon atoms which is optionally substituted by hydroxyl, C.sub.1 - to C.sub.3 -alkoxy or halogen,n denotes the number 1 to 3,x denotes the value 1.8 to 2.5,or if n=1 and A=C.sub.2 H.sub.4, R.sub.1 +R.sub.2 denotes an ethylene bridge.find utility for dyeing paper.Type: GrantFiled: September 9, 1985Date of Patent: March 3, 1987Assignee: Bayer AktiengesellschaftInventors: Manfred Groll, Dieter Ockelmann
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Patent number: 4606859Abstract: An infra-red absorbing phthalocyanine compound in which each of at least five of the peripheral carbon atoms in the 1, 4, 5, 8, 9, 12, 13 or 16 positions (the "3,6-positions") of the phthalocyanine nucleus, as shown in Formula I, is linked by an atom from Group VB or Group VIB of the Periodic Table, other than oxygen, to a carbon atom of an organic radical. In preferred compounds each of the eight 3,6-positions is linked by an atoms from Group VB or Group VIB, especially sulphur, selenium or nitrogen, to an organic radical.Type: GrantFiled: March 21, 1985Date of Patent: August 19, 1986Assignee: Imperial Chemical Industries PLCInventors: Peter J. Duggan, Paul F. Gordon
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Patent number: RE35145Abstract: A phthalocyanine compound of the formula:(R--X--).sub.m Pc(--Y--R.sup.1 --Z--).sub.n (--SO.sub.3 M).sub.p IwhereinPc is a phthalocyanine nucleus (Pc);eachR independently is a monovalent aromatic radical linked to a peripheral carbon atom of the Pc nucleus through X;X selected from S, Se and Te;m is 4 to 16;eachR.sup.1 independently is a divalent aromatic radical linked to two adjacent peripheral carbon atoms of the Pc nucleus through Y and Z;Y is selected from S, NT, Se and Te;Z is selected from S, Se, Te, NT and O;T is selected from H, alkyl and aryl;n is 0 to 7;M is H, a metal or optionally-substituted ammonium;andP is from 1 to 16.The compounds have a significant absorption band in the near infra red and depending on the number of sulphonic acids groups and the nature of the counter ion are soluble in aqueous and polar organic media.Type: GrantFiled: October 25, 1993Date of Patent: January 9, 1996Assignee: Zeneca LimitedInventors: William Stark, Nigel Hughes, Donald M. Gunn