Hetero Ring Attached Directly Or Indirectly To The Phthalocyanine Ring System By Nonionic Bonding Patents (Class 540/123)
  • Patent number: 5563260
    Abstract: 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: Grant
    Filed: February 9, 1995
    Date of Patent: October 8, 1996
    Assignee: Sandoz Ltd.
    Inventors: Bansi L. Kaul, Dominique Pflieger
  • Patent number: 5516899
    Abstract: 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: Grant
    Filed: July 20, 1994
    Date of Patent: May 14, 1996
    Assignee: Zeneca Limited
    Inventors: James S. Campbell, Peter Gregory, Dean Thetford
  • Patent number: 5484778
    Abstract: 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: Grant
    Filed: September 2, 1993
    Date of Patent: January 16, 1996
    Assignee: University Hospitals of Cleveland
    Inventors: Malcolm E. Kenney, Nancy L. Oleinick, Boris D. Rihter, Ying-Syi Li
  • Patent number: 5453501
    Abstract: 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: Grant
    Filed: April 4, 1994
    Date of Patent: September 26, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventor: Horst Jager
  • Patent number: 5444163
    Abstract: 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: Grant
    Filed: November 12, 1993
    Date of Patent: August 22, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Juergen Dornhagen, Manfred Patsch
  • Patent number: 5427616
    Abstract: 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: Grant
    Filed: June 1, 1994
    Date of Patent: June 27, 1995
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventors: Kosaku Tsuji, Yoshio Muramatsu, Shigeki Kato
  • Patent number: 5322760
    Abstract: 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: Grant
    Filed: November 29, 1991
    Date of Patent: June 21, 1994
    Assignee: Hitachi, Ltd.
    Inventors: Yuzo Itoh, Atsushi Kakuta, Akio Mukoh
  • Patent number: 5302708
    Abstract: 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: Grant
    Filed: August 6, 1992
    Date of Patent: April 12, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Thomas Beck, Werner H. Russ, Hartmut Springer, Marcus Banfer
  • Patent number: 5284943
    Abstract: Special tetraazaporphins containing Si, Ge or Sn as the central metal are useful for forming a recording layer in an optical recording medium.
    Type: Grant
    Filed: January 22, 1992
    Date of Patent: February 8, 1994
    Assignee: Hitachi Chemical Company, Co.
    Inventors: Seiji Tai, Nobuyuki Hayashi, Koichi Kamijima, Mitsuo Katayose, Takayuki Akimoto, Hideo Hagiwara
  • Patent number: 5279622
    Abstract: 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: Grant
    Filed: April 28, 1992
    Date of Patent: January 18, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Josef-Walter Stawitz, Frank-Michael Stohr, Joachim Wolff
  • Patent number: 5264032
    Abstract: 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: Grant
    Filed: October 21, 1992
    Date of Patent: November 23, 1993
    Assignee: Hoechst AG
    Inventors: Erwin Dietz, Manfred Urban
  • Patent number: 5250111
    Abstract: 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: Grant
    Filed: April 6, 1992
    Date of Patent: October 5, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Robert Langley, Michael D. McFarland
  • Patent number: 5217856
    Abstract: Special tetraazaporphins containing Si, Ge or Sn as the central metal are useful for forming a recording layer in an optical recording medium.
    Type: Grant
    Filed: April 6, 1989
    Date of Patent: June 8, 1993
    Assignee: Hitachi Chemical Co., Ltd.
    Inventors: Seiji Tai, Nobuyuki Hayashi, Koichi Kamijima, Mitsuo Katayose, Takayuki Akimoto, Hideo Hagiwara
  • Patent number: 5189153
    Abstract: 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: Grant
    Filed: June 19, 1990
    Date of Patent: February 23, 1993
    Assignee: Imperial Chemical Industries, PLC
    Inventors: Peter Gregory, Prakash Patel
  • Patent number: 5189154
    Abstract: 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: Grant
    Filed: June 28, 1991
    Date of Patent: February 23, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: Peter Gregory, Ronald W. Kenyon, Christine Millard
  • Patent number: 5149800
    Abstract: 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: Grant
    Filed: June 26, 1989
    Date of Patent: September 22, 1992
    Assignee: Milliken Research Corporation
    Inventors: Edward W. Kluger, Max A. Weaver
  • Patent number: 5039798
    Abstract: 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: Grant
    Filed: March 1, 1990
    Date of Patent: August 13, 1991
    Assignee: Hoechst Celanese Corp.
    Inventor: Robert E. Johnson
  • Patent number: 5032495
    Abstract: 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: Grant
    Filed: August 18, 1989
    Date of Patent: July 16, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernhard Albert, Peter Neumann, Rolf-Dieter Kohler
  • Patent number: 5015735
    Abstract: 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: Grant
    Filed: December 4, 1989
    Date of Patent: May 14, 1991
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventors: Yusaku Ide, Koji Nakamura, Shigeki Kato
  • Patent number: 4992532
    Abstract: 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: Grant
    Filed: May 3, 1989
    Date of Patent: February 12, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Rudolf Schaulin
  • Patent number: 4978747
    Abstract: 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: Grant
    Filed: April 13, 1989
    Date of Patent: December 18, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Arnold Weber, Hermann Henk, Klaus Kunde, Jochen Westphal, Klaus Wunderlich
  • Patent number: 4900817
    Abstract: 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: Grant
    Filed: May 31, 1988
    Date of Patent: February 13, 1990
    Assignee: Edison Polymer Innovation Corporation
    Inventors: Daniel A. Batzel, Scott E. Rickert, Malcolm E. Kenney
  • Patent number: 4845209
    Abstract: 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: Grant
    Filed: August 4, 1988
    Date of Patent: July 4, 1989
    Inventor: Jean-Marie Adam
  • Patent number: 4824947
    Abstract: 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: Grant
    Filed: March 1, 1988
    Date of Patent: April 25, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventor: William M. Stark
  • Patent number: 4824948
    Abstract: 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: Grant
    Filed: March 1, 1988
    Date of Patent: April 25, 1989
    Assignee: Imperial Chemical Industries plc
    Inventors: William Stark, Nigel Hughes, Donald M. Gunn
  • Patent number: 4800145
    Abstract: 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: Grant
    Filed: July 14, 1987
    Date of Patent: January 24, 1989
    Assignee: Imperial Chemical Industries, PLC
    Inventors: Anthony J. Nelson, Peter J. Duggan
  • Patent number: 4783386
    Abstract: 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: Grant
    Filed: January 12, 1987
    Date of Patent: November 8, 1988
    Assignee: Hoechst Celanese Corporation
    Inventors: David E. Nikles, R. Sidney Jones, Jr., James E. Kuder
  • Patent number: 4745187
    Abstract: 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: Grant
    Filed: January 29, 1987
    Date of Patent: May 17, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Hartmut Springer
  • Patent number: 4657554
    Abstract: 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: Grant
    Filed: May 22, 1985
    Date of Patent: April 14, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Gerhard Reinert, Gerd Holzle, Gregor Graf
  • Patent number: 4648992
    Abstract: 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: Grant
    Filed: February 11, 1985
    Date of Patent: March 10, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Gregor Graf, Gerd Holzle, Gerhard Reinert
  • Patent number: 4606859
    Abstract: 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: Grant
    Filed: March 21, 1985
    Date of Patent: August 19, 1986
    Assignee: Imperial Chemical Industries PLC
    Inventors: Peter J. Duggan, Paul F. Gordon
  • Patent number: RE35145
    Abstract: 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: Grant
    Filed: October 25, 1993
    Date of Patent: January 9, 1996
    Assignee: Zeneca Limited
    Inventors: William Stark, Nigel Hughes, Donald M. Gunn