# US 5,350,843 A · Halogenated phthalocyanine compound, method for preparing same > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,350,843 A - Document ID: US5350843A - Status: Granted - Kind: A - Application number: 07/877,174 - Filed: 1992-07-06 - Granted: 1994-09-27 - Earliest claimed: 1990-11-06 - Assignees: Mitsui Toatsu Chemicals, Inc.; Yamamoto Chemicals, Inc. - Inventors: Hisato Itoh; Takahisa Oguchi; Shin Aihara; Kenichi Sugimoto - Web page: https://patentgrep.com/patent/US5350843A ## CPC - C07D 487/22: in which the condensed system contains four or more hetero rings - C09B 47/063: {having oxygen or sulfur atom(s) linked directly to the skeleton} - C09B 47/073: Preparation from isoindolenines {, e.g. pyrrolenines} - C09B 47/10: Obtaining compounds having halogen atoms directly bound to the phthalocyanine skeleton - G11B 7/248: porphines; azaporphines, e.g. phthalocyanines - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P) - G11B: INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER (recording measured values in a way that does not require playback through a transducer G01D9/00; recording or playback apparatus using mechanically marked tape, e.g. punched paper tape, or using unit records, e.g. punched or magnetically marked cards G06K; transferring data from one type of record carrier to another G06K1/18; circuits for coupling output of reproducer to radio receiver H04B1/20; gramophone pick-ups or like acoustic electromechanical transducers or circuits therefor H04R) ## Abstract A method for preparing a mixture of the halogenated alkoxyphthalocyanines represented by the formula (8) which comprises the step of reacting alkoxyphthalocyanines represented by the formula (7) and a mixture thereof with a halogenating agent in a mixed solvent of an organic solvent and water. ##STR1## ## Claims ### Claim 1 A method for preparing a halogenated phthalocyanine compound represented by the formula (20) ##STR59## wherein each of R.sup.9 to R.sup.12 independently is a substituted or unsubstituted alkyl group; and Met is two hydrogen atoms, a divalent metallic atom, a trivalent or a tetravalent metallic derivative; X is chlorine, bromine or iodine; and n is 1.ltoreq.n.ltoreq.12, which comprises reacting a phthalocyanine compound represented by the formula (19) ##STR60## wherein R.sup.9 to R.sup.12 and Met have the same meanings as in the formula (20), with a halogenating agent at 20.degree. to 90.degree. C. in a mixed solvent of an organic solvent and water. ### Claim 2 (depends on 1) The method for preparing a halogenated phthalocyanine compound according to claim 1 wherein said phthalocyanine compound is a compound represented by the formula (21), (22), (23) or (24) ##STR61## wherein R.sup.9 to R.sup.12 and Met have the same meanings as in the formula (19), or a mixture of these compounds; and said halogenated phthalocyanine compound is a compound represented by the formula (25), (26), (27) or (28) ##STR62## wherein R.sup.9 to R.sup.12, Met, X and n have the same meanings as in the formula (20), or a mixture of these compounds. ### Claim 3 (depends on 2) The method for preparing a halogenated phthalocyanine compound according to claim 2 wherein at least one of R.sup.9 to R.sup.12 is a branched alkyl group. ### Claim 4 (depends on 3) The method for preparing a halogenated phthalocyanine compound according to claim 3 wherein R.sup.9 to R.sup.12 are secondary alkyl groups. ### Claim 5 (depends on 1) The method for preparing a halogenated phthalocyanine compound according to claim 1 wherein X is bromine; n is 1.ltoreq.n.ltoreq.4; and Met is Pd, Cu, Ni, Co or VO. ### Claim 6 (depends on 1) The method for preparing a halogenated phthalocyanine compound according to claim 1 wherein said halogenating agent is bromine. ### Claim 7 (depends on 1) The method for preparing a halogenated phthalocyanine compound according to claim 1 wherein said organic solvent forms two layers with water. ### Claim 8 (depends on 7) The method for preparing a halogenated phthalocyanine compound according to claim 7 wherein said organic solvent is one or more selected from saturated hydrocarbons, ethers and halogenated hydrocarbons. ### Claim 9 (depends on 8) The method for preparing a halogenated phthalocyanine compound according to claim 8 wherein said organic solvent is one or more selected from the group consisting of n-hexane, n-pentane, n-octane, cyclohexane, methylcyclohexane, ethylcyclohexane, tetrahydrofuran, n-butyl ether, n-propyl ether, isopropyl ether, carbon tetrachloride, chloroform, dichloromethane, 1,1,1-trichloroethane, 1,1,2-trichloroethane and 1,1,2,2-tetrachloroethane. ### Claim 10 (depends on 1) The method for preparing a halogenated phthalocyanine compound according to claim 1 wherein the amount of said organic solvent is 2 to 200 times by weight as much as that of said phthalocyanine compound and said mixture. ### Claim 11 (depends on 1) The method for preparing a halogenated phthalocyanine compound according to claim 1 wherein the amount of water is 0.1 to 5 times by weight as much as that of said organic solvent. ### Claim 12 (depends on 1) The method for preparing a halogenated phthalocyanine compound according to claim 1 wherein the amount of said halogenating agent is in a molar ratio of 1-16 to said phthalocyanine compound and said mixture. ### Claim 13 (depends on 10) The method for preparing a halogenated phthalocyanine compound according to claim 10 wherein the amount of said organic solvent is 4 to 10 times by weight as much as that of said phthalocyanine compound and said mixture. ### Claim 14 (depends on 12) The method for preparing a halogenated phthalocyanine compound according to claim 12 wherein the amount of bromine is in a molar ratio of 1-4 to said phthalocyanine compound and said mixture.