Hetero Ring Attached Directly Or Indirectly To The Phthalocyanine Ring System By Nonionic Bonding Patents (Class 540/123)
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Patent number: 5563260Abstract: The compounds of general formula I ##STR1## wherein R represents chlorine or hydroxylPc represents a phthalocyanine radicalR.sub.1 may be alkyl and R.sub.2 may be alkyl ammoniumare excellently suitable for dyeing of plastic materials, paper and inks for ball point pens.Type: GrantFiled: February 9, 1995Date of Patent: October 8, 1996Assignee: Sandoz Ltd.Inventors: Bansi L. Kaul, Dominique Pflieger
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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: 5453501Abstract: Phthalocyanine reactive dyestuffs which, in the form of the free acid, have the formula (1) ##STR1## in which the variable radicals have the meaning given in the description, are prepared by condensation of the corresponding amines with cyanuric fluoride or cyanuric chloride in any desired order.The reactive dyestuffs according to the invention exhibit good wet and light fastness properties and are used for the dyeing and printing of cotton.Type: GrantFiled: April 4, 1994Date of Patent: September 26, 1995Assignee: Bayer AktiengesellschaftInventor: Horst Jager
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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: 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: 5264032Abstract: Pigment preparation essentially comprisinga) at least one pigment from the class of azo, anthrapyrimidine, anthanthrone, quinacridone, perinone, diketopyrrolopyrrole, dioxazine, flavanthrone, indanthrone, isoindolinone, isoviolanthrone, perylene, phthalocyanine, pyranthrone or thioindigo pigments or a mixture of pigments belonging to various classes, andb) at least one dispersant of the formula (I) ##STR1## in which P, independently of the pigments mentioned in a), is a radical of an anthanthrone azo, quinacridone, perinone, diketopyrrolopyrrole, dioxazine, indanthrone, perylene, phthalocyanine or thioindigo pigment,R.sup.1 and R.sup.2, independently of one another, are hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.Type: GrantFiled: October 21, 1992Date of Patent: November 23, 1993Assignee: Hoechst AGInventors: Erwin Dietz, Manfred Urban
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Patent number: 5250111Abstract: A pigment composition comprising a) a pigment; and b) a phthalocyanine compound having the formula I:MPc(CH.sub.2 NHCO--A).sub.n Iin which Pc represents a phthalocyanine residue which is optionally further substituted by up to an average of one chlorine or bromine atom or by a sulphonic acid group; M is hydrogen or a metal capable of forming a metal phthalocyanine; n is a number ranging from 0.1 to 4.0; and A is C.sub.3 -C.sub.21 alkenyl, C.sub.5 -C.sub.8 cycloalkyl, C.sub.7 -C.sub.11 aralkyl, C.sub.6 -C.sub.10 aryl, a 5- or 6-membered heterocyclic residue or a fused heterocyclic system.Type: GrantFiled: April 6, 1992Date of Patent: October 5, 1993Assignee: Ciba-Geigy CorporationInventors: Robert Langley, Michael D. McFarland
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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: 5149800Abstract: A colorant for natural or synthetic resinous or polymeric materials, having the formula:A--[D--Z--SO.sub.2 --N(R.sub.2)--Y].sub.1-16wherein; R.sub.2 is selected from hydrogen, methyl, cyclohexyl, phenyl or Y; A is a nonionic metallophthalocyanine chromophore which can be substituted for example with halogen, alkyl, alkoxy, alkylthio, or aryloxy; Z is an arylene moiety; D is a linking group being or containing at least one of --O--, --S--, --SO.sub.2 --, --N(R.sub.3)--, or --N(SO.sub.2 R.sub.4)-- as the linking moiety, wherein R.sub.4 is unsubstituted or substituted alkyl, cycloalkyl or aryl, and R.sub.3 is R.sub.Type: GrantFiled: June 26, 1989Date of Patent: September 22, 1992Assignee: Milliken Research CorporationInventors: Edward W. Kluger, Max A. Weaver
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Patent number: 5039798Abstract: Provided are novel naphthalocyanine dimer compounds of the general formula:RO--YNc--O--NcY--OR (I)wherein Nc represents a naphthalocyanine moiety, which can be substituted or unsubstituted; Y represents a central hetero atom of the naphthalocyanine moiety; and, OR represents an alkoxide cap bonded to the central hetero atom Y, with the first carbon atom of the alkoxide (OR) capping group being a tertiary carbon. Also provided is a method for preparing the dimer compounds, which method comprises reacting a naphthalocyanine dihalide in solution with a tertiary alcohol and a nucleophile. The process efficiently and reproducibly provides a naphthalocyanine oxo-bridged dimer having terminal alkoxide caps.Type: GrantFiled: March 1, 1990Date of Patent: August 13, 1991Assignee: Hoechst Celanese Corp.Inventor: Robert E. Johnson
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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: 5015735Abstract: A process for the preparation of a copper phthalocyanine pigment which comprises adding a dry ground mixture of crude copper phthalocyanine containing 0.1 to 20% by weight of a crystal growth inhibitor to a 50 to 90% by weight aqueous solution of sulfuric acid to obtain a sulfuric acid slurry of the dry ground mixture, adding water to the slurry to form a precipitate and recovering it to obtain pigment grade copper phthalocyanine. The copper phthalocyanine pigment prepared according to the present invention is usable in coating materials, inks or plastics.Type: GrantFiled: December 4, 1989Date of Patent: May 14, 1991Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Yusaku Ide, Koji Nakamura, Shigeki Kato
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Patent number: 4992532Abstract: The compounds of the formula ##STR1## where the substituents and indices are as defined in claim 1, are green direct dyes for various substrates, in particular cellulosic fibre materials. They are high-temperature stable and therefore are particularly highly suitable for the one-bath, single-stage dyeing of polyester/cotton blend fabrics together with a disperse dye for the polyester fibres under the dyeing conditions for polyester fibres.Type: GrantFiled: May 3, 1989Date of Patent: February 12, 1991Assignee: Ciba-Geigy CorporationInventor: Rudolf Schaulin
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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: 4900817Abstract: Compounds are disclosed which comprise parallel, multiring, porphyrin-related compounds, particularly two-ring phthalocyanine compounds, which have a coordinating atom, either a metal or a metalloid, located at their center. The coordinating atoms in adjacent rings are connected by an oxygen bridge along an axial backbone disposed at right angles to the rings, and the coordinating atom and the ring on one end of the axis has a hydrophilic group attached thereto, while the coordinating atom in the ring at the other end of the axis has a hydrophobic group attached to it. Semiconducting films made from such compounds and devices made from such films, especially gas sensors, are also disclosed.Type: GrantFiled: May 31, 1988Date of Patent: February 13, 1990Assignee: Edison Polymer Innovation CorporationInventors: Daniel A. Batzel, Scott E. Rickert, Malcolm E. Kenney
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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: 4800145Abstract: An organic photoconductor suitable for use in electro-reprography comprising an electrically conducting support, a charge generating phase comprising a charge generator and a charge transport phase characterized in that the charge generator is a phthalocyanine compound in which each of at least four of the peripheral carbon atoms numbered from 1 to 16 in the phthalocyanine nucleus shown below is linked, by an atom from Group VA or Group VIA of the Periodic Table, to a carbon atom of an organic radical.Type: GrantFiled: July 14, 1987Date of Patent: January 24, 1989Assignee: Imperial Chemical Industries, PLCInventors: Anthony J. Nelson, Peter J. Duggan
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Patent number: 4783386Abstract: Provided is an optical information recording medium and a method of recording information thereon. The information layer of the recording medium comprises an anthracyanine or phenanthracyanine chromophore compound. In a preferred embodiment, the chromophore is substituted with at least one substituent conferring film forming properties to the chromophore, e.g., a monomer or oligomeric substituent comprised of acid, amide or ester units. The resulting information layer exhibits strong absorption in the range of from about 780-850 nm. Employing an anthracyanine or phenanthracyanine chromophore substituted with a film forming substituent further offers the advantages of a single component material exhibiting good thermomechanical properties.Type: GrantFiled: January 12, 1987Date of Patent: November 8, 1988Assignee: Hoechst Celanese CorporationInventors: David E. Nikles, R. Sidney Jones, Jr., James E. Kuder
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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: 4657554Abstract: Novel azaphthalocyanines are described which are of the formula ##STR1## in which Me is Al(III), Zn(II), Ge(IV) or Sn(IV), E is an anionic group, Z is a cation, Y is a halogen, n is any desired number from 1 to 3 and p is any desired number from 0 to 2, the sum n+p being at most 8 and A, B, C and D independently of one another completing a benzene ring or a ring of the formula ##STR2## at least one of the rings completed by A, B, C or D being one of the said heterocyclic rings.The novel compounds can be used as photoactivators, in particular for bleaching textiles and for controlling microorganisms in or on organic or inorganic substrates.Bleaching, washing and steeping agents and antimicrobially active agents are also described which contain the novel azaphthalocyanine compounds.Type: GrantFiled: May 22, 1985Date of Patent: April 14, 1987Assignee: Ciba-Geigy CorporationInventors: Gerhard Reinert, Gerd Holzle, Gregor Graf
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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: 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