WO2022045236A1 - フタロシアニンの製造方法 - Google Patents

フタロシアニンの製造方法 Download PDF

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Publication number
WO2022045236A1
WO2022045236A1 PCT/JP2021/031298 JP2021031298W WO2022045236A1 WO 2022045236 A1 WO2022045236 A1 WO 2022045236A1 JP 2021031298 W JP2021031298 W JP 2021031298W WO 2022045236 A1 WO2022045236 A1 WO 2022045236A1
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preferable
formula
mol
compound
compound represented
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English (en)
French (fr)
Japanese (ja)
Inventor
シオンワン フー
博 江波戸
宗矩 櫻井
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DIC Corp
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DIC Corp
Dainippon Ink and Chemicals Co Ltd
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Priority to CN202180052981.2A priority Critical patent/CN115989285A/zh
Priority to JP2022521377A priority patent/JP7168126B2/ja
Publication of WO2022045236A1 publication Critical patent/WO2022045236A1/ja
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/006—Preparation of organic pigments

Definitions

  • the present invention relates to a method for producing phthalocyanine.
  • Phthalocyanine has a hue of blue to green and is an excellent pigment with a wide range of uses.
  • phthalocyanines are generally synthesized from phthalic anhydride, phthalic acid or phthalonitrile. Synthetic approaches using phthalimide or 1,3-diiminoisoindoline are also uncommon. Since the types of phthalocyanine derivatives that are the starting materials for phthalocyanine synthesis are limited, the method for derivatizing the final product, phthalocyanine, is also limited. Therefore, industrially, phthalocyanines having no functional group are generally produced.
  • the functional group that binds to the phthalocyanine skeleton is very important because its hue can be finely adjusted by its electron donating property and electron attracting property. Furthermore, phthalocyanine having a functional group also acts as an additive for controlling crystal growth during pigment formation. Due to this importance, a method for directly introducing a functional group into phthalocyanine has been developed. Particularly successful examples are the halogenation, sulfonated and imidized phthalocyanines (Patent Documents 1, 2 and 3). However, these methods still have the problem that the number and position of functional groups cannot be controlled and the types of functional groups that can be used are very limited. Therefore, it is desired to develop a technique capable of introducing a new functional group by controlling the number and position of the functional group of phthalocyanine.
  • the problem to be solved by the present invention is to provide high-performance phthalocyanine compounds and compositions that can be used in pigment compositions, pigment dispersions, printing inks, paints, printed matter, laminated matter of printed matter, coating materials, color filters and the like. It is an object of the present invention to provide a production method capable of producing various kinds of functional groups from a biomass raw material in a controllable number and position.
  • the present invention has the following formula (DA-1).
  • R 1 to R 4 independently represent a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyclohexyl group, and a phenyl group.
  • the present invention relates to a production method for obtaining a compound represented by.
  • the present invention provides a production method for obtaining a phthalocyanine derivative into which a functional group is introduced while controlling the number and position of the phthalocyanine skeleton as a final product and a composition containing the phthalocyanine derivative by using a furan derivative as a starting material.
  • a furan derivative and maleic anhydride can be obtained from biomass, and according to the present invention, a phthalocyanine compound and a composition derived from biomass can be provided, which can contribute to reduction of environmental load.
  • the phthalocyanine composition capable of controlling pigment crystallization, resin dispersibility and hue by the compounds represented by the above formulas (IA) to (IIE) derived from the compound produced as a by-product in the step of obtaining the DA intermediate. It also leads to higher performance.
  • R 1 to R 4 independently represent a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyclohexyl group, and a phenyl group.
  • the compound represented by the above formula (I) or (II) of the present invention can be obtained from the compound represented by the formula (PA-1).
  • the compound represented by the formula (DA-1) is not limited, and examples thereof include the following compounds (DA-1-1) to (DA-1-17).
  • the compound represented by the above formula (PA-1) is not limited, and examples thereof include the following compounds (PA-1-1) to (PA-1-17).
  • the compound represented by the above formula (DA-1) may be any compound as long as it allows the reaction to proceed appropriately, but the following formula (FR-1) may be used.
  • R 1 to R 4 in the formula have the same meaning as R 1 to R 4 above. It is preferable to obtain it by reacting the compound represented by (1) with maleic anhydride.
  • the compound represented by the formula (FR-1) is not limited, and examples thereof include the following compounds (FR-1-1) to (FR-1-5).
  • any compound can be used as long as the reaction can proceed appropriately, but a catalyst is used.
  • the catalyst may be any one as long as it allows the reaction to proceed appropriately, but hydrochloric acid, sulfuric acid, p-toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, polyphosphoric acid, diphosphate, trifluoroacetic acid, etc.
  • X represents -OH, -ONa, -OK, -R 5
  • R 5 has the same meaning as R 1 to R 4
  • Y represents a sulfur atom or a phosphorus atom
  • Z represents a hydrogen atom.
  • -COR 6 , -COH or -CO-CF 3 is represented, and R 6 has the same meaning as R 1 to R 4 above. It is preferably a compound represented by.
  • the amount of the catalyst is preferably 0.1 to 3000 mol%, preferably 0.5 to 2500 mol%, preferably 1 to 2000 mol%, and 5 to 1500 mol with respect to the compound represented by the above formula (DA-1). % Is preferred, 10 to 1000 mol% is preferred, 20 to 500 mol% is preferred, 50 to 500 mol% is preferred, 70 to 500 mol% is preferred, 100 to 500 mol% is preferred, 150 to 500 mol% is preferred, and 200 to 500 mol% is preferred. Is preferable, 250 to 500 mol% is preferable, and 300 to 500 mol% is preferable.
  • the lower limit is preferably 0.1 mol% or more, preferably 0.5 mol% or more, preferably 1 mol% or more, preferably 5 mol% or more, preferably 10 mol% or more, preferably 20 mol% or more, preferably 50 mol% or more, and 70 mol. % Or more is preferable, 100 mol% or more is preferable, 150 mol% or more is preferable, 200 mol% or more is preferable, 250 mol% or more is preferable, and 300 mol% or more is preferable.
  • the upper limit value is preferably 3000 mol% or less, preferably 2500 mol% or less, preferably 2000 mol% or less, preferably 1500 mol% or less, preferably 1000 mol% or less, and preferably 500 mol% or less. These upper and lower limit values are used in any combination. In this production method, it is preferable that all of R 1 to R 4 represent hydrogen atoms.
  • the maleic anhydride is preferably derived from biomass.
  • the compound represented by the formula (FR-1) is preferably derived from biomass. It is more preferable that both maleic anhydride and the compound represented by the formula (FR-1) are derived from biomass.
  • biomass refers to plants as a source of alternative energy.
  • Biomass is mainly composed of two components, lignin and (hemi) cellulose. Both lignin and (hemi) cellulose are macromolecules, lignin is composed of aromatic monomers, and (hemi) cellulose is composed of sugars having 5 carbon atoms and sugars having 6 carbon atoms.
  • both a raw material derived from lignin and a raw material derived from (hemi) cellulose can be used as raw materials.
  • the biomass degree of the raw material used in the above production method is preferably 1% or more, preferably 5% or more, preferably 10% or more, preferably 15% or more, preferably 20% or more, preferably 25% or more, and 30% or more.
  • 35% or more is preferable, 40% or more is preferable, 45% or more is preferable, 50% or more is preferable, 55% or more is preferable, 60% or more is preferable, 65% or more is preferable, and 70% or more is preferable. 75% or more is preferable, 80% or more is preferable, 85% or more is more preferable, 90% or more is further preferable, and 95% or more is particularly preferable.
  • the degree of biomass referred to here refers to the carbon content (% by mass) of the biomass deadline in total carbon calculated by measurement according to ASTM-D6866-18.
  • the biomass-derived maleic anhydride can be obtained, for example, by dehydrating and cyclizing maleic acid obtained by oxidizing FF or HMF obtained by the method described in Patent Document 4 or 5, or by directly oxidizing it. Can also be obtained.
  • As the compound represented by the formula (FR-1) derived from biomass for example, a decarbonylation reaction, a reduction reaction, a dehydration reaction and the like are appropriately combined with FF and HMF obtained by the method described in Patent Document 4 or 5.
  • Compound (DA-1) can be produced by subjecting compound (FR-1) and maleic anhydride to a Diels-Alder reaction.
  • the reaction solvent may be any one as long as it allows the reaction to proceed suitably, but chloroform, dioxane, ethyl acetate, alkylbenzene, toluene, xylene and diethyl ether are preferable.
  • the reaction temperature may be any as long as it allows the reaction to proceed suitably, but is preferably ⁇ 10 to 100 ° C., more preferably 0 ° C. to 80 ° C., still more preferably 10 ° C. to 70 ° C., and 15 ° C. to 50 ° C. Is particularly preferable.
  • As the lower limit value ⁇ 10 ° C. or higher is preferable, 0 ° C. or higher is more preferable, 10 ° C. or higher is further preferable, and 15 ° C. or higher is particularly preferable.
  • the upper limit is preferably 100 ° C. or lower, more preferably 80 ° C. or lower, further preferably 70 ° C. or lower, and particularly preferably 50 ° C. or lower.
  • the reaction pressure may be any as long as it allows the reaction to proceed suitably, but is preferably 0.1 to 5 MPa, more preferably 0.1 to 3 MPa, still more preferably 0.1 to 1 MPa, and 0.1 to 0. 5.5 MPa is particularly preferable.
  • the lower limit value is preferably 0.1 MPa or more, preferably 0.2 MPa or more, preferably 0.3 MPa or more, and preferably 0.4 MPa or more.
  • the upper limit is preferably 5 MPa or less, preferably 3 MPa or less, preferably 1 MPa or less, preferably 0.9 MPa or less, preferably 0.8 MPa or less, preferably 0.7 MPa or less, preferably 0.6 MPa or less, and preferably 0.5 MPa.
  • the following is preferable.
  • reaction B The compound (PA-1) can be produced by subjecting the compound (DA-1) obtained in the reaction A to a ring-opening dehydration reaction.
  • the reaction solvent may be any one as long as it allows the reaction to proceed suitably, but water, acetonitrile, toluene, xylene, alkylbenzene, or a mixed solvent of each, or no solvent is preferable.
  • the reaction temperature may be any as long as it allows the reaction to proceed suitably, but is preferably 20 to 150 ° C, more preferably 30 to 120 ° C, and even more preferably 40 to 100 ° C.
  • the lower limit value is preferably 20 ° C. or higher, preferably 25 ° C. or higher, preferably 30 ° C. or higher, preferably 35 ° C. or higher, and preferably 40 ° C. or higher.
  • the upper limit value is preferably 150 ° C. or lower, preferably 140 ° C. or lower, preferably 130 ° C. or lower, preferably 120 ° C. or lower, preferably 110 ° C. or lower, and preferably 100 ° C. or lower.
  • the catalyst may be any one as long as it allows the reaction to proceed appropriately, but hydrochloric acid, sulfuric acid, p-toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, polyphosphoric acid, diphosphate, trifluoroacetic acid, etc. Or the following formula (AC)
  • X represents -OH, -ONa, -OK, -R 5
  • R 5 has the same meaning as R 1 to R 4
  • Y represents a sulfur atom or a phosphorus atom
  • Z represents a hydrogen atom.
  • -COR 6 , -COH or -CO-CF 3 is represented, and R 6 has the same meaning as R 1 to R 4 above. It is preferably a compound represented by.
  • the amount of the catalyst is preferably 0.1 to 3000 mol%, preferably 0.5 to 2500 mol%, preferably 1 to 2000 mol%, and 5 to 1500 mol with respect to the compound represented by the above formula (DA-1). % Is preferred, 10 to 1000 mol% is preferred, 20 to 500 mol% is preferred, 50 to 500 mol% is preferred, 70 to 500 mol% is preferred, 100 to 500 mol% is preferred, 150 to 500 mol% is preferred, and 200 to 500 mol% is preferred. Is preferable, 250 to 500 mol% is preferable, and 300 to 500 mol% is preferable.
  • the lower limit is preferably 0.1 mol% or more, preferably 0.5 mol% or more, preferably 1 mol% or more, preferably 5 mol% or more, preferably 10 mol% or more, preferably 20 mol% or more, preferably 50 mol% or more, and 70 mol. % Or more is preferable, 100 mol% or more is preferable, 150 mol% or more is preferable, 200 mol% or more is preferable, 250 mol% or more is preferable, and 300 mol% or more is preferable.
  • the upper limit value is preferably 3000 mol% or less, preferably 2500 mol% or less, preferably 2000 mol% or less, preferably 1500 mol% or less, preferably 1000 mol% or less, and preferably 500 mol% or less. These upper and lower limit values are used in any combination.
  • Reaction C Compound (I) can be produced by reacting the compound (PA-1) obtained in Reaction B with urea and MX in the presence of a catalyst.
  • the reaction solvent may be any one as long as it allows the reaction to proceed suitably, but solvent-free and alkylbenzene are preferable.
  • the reaction temperature may be any as long as it allows the reaction to proceed suitably, but it is preferably 100 to 250 ° C, preferably 110 to 240 ° C, preferably 120 to 230 ° C, preferably 130 to 220 ° C, and 140 to 210.
  • the temperature is preferably 150 to 200 ° C.
  • the lower limit value is preferably 100 ° C. or higher, preferably 110 ° C. or higher, preferably 120 ° C. or higher, preferably 130 ° C. or higher, preferably 140 ° C. or higher, and preferably 150 ° C. or higher.
  • the upper limit is preferably 250 ° C. or lower, preferably 240 ° C. or lower, preferably 230 ° C. or lower, preferably 220 ° C. or lower, preferably 210 ° C. or lower, and preferably 200 ° C. or lower.
  • M represents a metal atom, it is preferably Al, Si, Sc, Ti, V, Mg, Fe, Co, Ni, Cu, Zn, Ga, Ge, Y, Zr, Nb, In, Sn or Pb. , Al, Fe, Cu, Zn, more preferably Cu, Zn.
  • the catalyst may be any catalyst that allows the reaction to proceed suitably, but a molybdenum catalyst is preferable, and ammonium molybdenum (IV) acid tetrahydrate is more preferable.
  • a molybdenum catalyst is preferable, and ammonium molybdenum (IV) acid tetrahydrate is more preferable.
  • R1 to R4 in the formula have the same meanings as R1 to R4 in the formula (I) independently of each other.
  • reaction D The compound (I) obtained in the reaction C can be produced by carrying out a demetallization reaction to produce the compound (II).
  • the demetallization reaction may be any reaction as long as it proceeds favorably, and examples thereof include the method described in Chemcomm Communication, 2009, 1970-1971.
  • R 1 to R 4 have the same meaning as R 1 to R 4 , and M has the same meaning as M.
  • M has the same meaning as M.
  • the compound represented by the above formula (IA), (IIA), (IB), (IIB), (IC), (IIC), (ID) is obtained from the compound represented by the formula (PA-2). , (IID), (IE) or (IIE) can be obtained.
  • the compound represented by the formula (DA-2) is not limited, and examples thereof include the following compounds (DA-2-1) to (DA-2-7).
  • the compound represented by the above formula (PA-2) is not limited, and examples thereof include the following compounds (PA-2-1) to (PA-2-7).
  • the compound represented by the formula (DA-2) may be any compound as long as it allows the reaction to proceed appropriately, but it is obtained by reacting the compound represented by the formula (FR-1) with maleic anhydride. Is preferable. At this time, it is preferable to use the compound represented by the formula (FR-1) in an excess amount in a molar ratio with respect to maleic anhydride.
  • the compound represented by the formula (PA-2) is obtained from the compound represented by the formula (DA-2), any compound can be used as long as the reaction can proceed appropriately, but a catalyst is used. Is preferable.
  • the catalyst may be any one as long as it allows the reaction to proceed appropriately, but hydrochloric acid, sulfuric acid, p-toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, polyphosphoric acid, diphosphate, trifluoroacetic acid, etc. Or the following formula (AC)
  • X represents -OH, -ONa, -OK, -R 5 , R 5 has the same meaning as R 1 to R 4 , Y represents a sulfur atom or a phosphorus atom, and Z represents a hydrogen atom.
  • -COR 6 , -COH or -CO-CF 3 is represented, and R 6 has the same meaning as R 1 to R 4 above.
  • the amount of the catalyst is preferably 0.1 to 3000 mol%, preferably 0.5 to 2500 mol%, preferably 1 to 2000 mol%, and 5 to 1500 mol with respect to the compound represented by the above formula (DA-2).
  • the lower limit is preferably 0.1 mol% or more, preferably 0.5 mol% or more, preferably 1 mol% or more, preferably 5 mol% or more, preferably 10 mol% or more, preferably 20 mol% or more, preferably 50 mol% or more, and 70 mol.
  • % Or more is preferable, 100 mol% or more is preferable, 150 mol% or more is preferable, 200 mol% or more is preferable, 250 mol% or more is preferable, and 300 mol% or more is preferable.
  • the upper limit value is preferably 3000 mol% or less, preferably 2500 mol% or less, preferably 2000 mol% or less, preferably 1500 mol% or less, preferably 1000 mol% or less, and preferably 500 mol% or less. These upper and lower limit values are used in any combination. In the present production method, it is preferable that all of R 1 to R 4 represent hydrogen atoms.
  • the maleic anhydride is preferably derived from biomass.
  • the compound represented by the formula (FR-1) is preferably derived from biomass. It is more preferable that both maleic anhydride and the compound represented by the formula (FR-1) are derived from biomass.
  • reaction A2 By subjecting the compound (FR-1) and maleic anhydride to the Diels-Alder reaction, a composition containing the compounds (DA-1) and (DA-2) can be produced.
  • the reaction solvent may be any one as long as it allows the reaction to proceed suitably, but chloroform, dioxane, ethyl acetate, alkylbenzene, toluene, xylene and diethyl ether are preferable.
  • the reaction temperature may be any as long as it allows the reaction to proceed suitably, but is preferably ⁇ 10 to 100 ° C., more preferably 0 ° C.
  • the lower limit value ⁇ 10 ° C. or higher is preferable, 0 ° C. or higher is more preferable, 10 ° C. or higher is further preferable, and 15 ° C. or higher is particularly preferable.
  • the upper limit is preferably 100 ° C. or lower, more preferably 80 ° C. or lower, further preferably 70 ° C. or lower, and particularly preferably 50 ° C. or lower. In order to promote the formation of the compound (DA-2), 0 to 100 ° C. is preferable, 10 to 100 ° C. is preferable, 15 to 100 ° C.
  • the lower limit value is preferably 0 ° C. or higher, preferably 10 ° C. or higher, more preferably 15 ° C. or higher, further preferably 20 ° C. or higher, and particularly preferably 25 ° C. or higher.
  • -10 to 90 ° C is preferable, -10 to 80 ° C is preferable, -10 to 70 ° C is more preferable, -10 to 60 ° C is even more preferable, and -10. ⁇ 50 ° C. is particularly preferable.
  • the upper limit is preferably 90 ° C. or lower, preferably 80 ° C. or lower, more preferably 70 ° C. or lower, further preferably 60 ° C. or lower, and particularly preferably 50 ° C. or lower.
  • the reaction pressure may be any as long as it allows the reaction to proceed suitably, but is preferably 0.1 to 5 MPa, more preferably 0.1 to 3 MPa, still more preferably 0.1 to 1 MPa, and 0.1 to 0. 5.5 MPa is particularly preferable.
  • the lower limit value is preferably 0.1 MPa or more, preferably 0.2 MPa or more, preferably 0.3 MPa or more, and preferably 0.4 MPa or more.
  • the upper limit is preferably 5 MPa or less, preferably 3 MPa or less, preferably 1 MPa or less, preferably 0.9 MPa or less, preferably 0.8 MPa or less, preferably 0.7 MPa or less, preferably 0.6 MPa or less, and preferably 0.5 MPa.
  • the following is preferable.
  • 0.15 to 5 MPa is preferable, 0.2 to 3 MPa is more preferable, 0.25 to 1 MPa is further preferable, and 0.3 to 1 MPa is particularly preferable.
  • As the lower limit value 0.15 MPa or more is preferable, 0.2 MPa or more is more preferable, 0.25 MPa or more is further preferable, and 0.3 MPa or more is particularly preferable.
  • 0.1 to 3 MPa is preferable, 0.1 to 1 MPa is more preferable, 0.1 to 0.5 MPa is further preferable, and 0.1 to 0.4 MPa is preferable.
  • the upper limit is preferably 3 MPa or less, more preferably 1 MPa or less, further preferably 0.5 MPa or less, and particularly preferably 0.4 MPa or less.
  • the production ratio of the compound (DA-1) and the compound (DA-2) can be controlled by changing the equivalents of the compound (FR-1) and maleic anhydride.
  • any one may be used as long as the reaction is appropriately promoted, but the equivalent of the compound (FR-1) to maleic anhydride is 2.0 to 15.0.
  • 4.0 to 14.0 is more preferable, 6.0 to 13.0 is further preferable, and 8.0 to 12.0 is particularly preferable.
  • As the lower limit value 2.0 or more is preferable, 4.0 or more is more preferable, 6.0 or more is further preferable, and 8.0 or more is particularly preferable.
  • the upper limit is preferably 15.0 or less, more preferably 14.0 or less, further preferably 13.0 or less, and particularly preferably 12.0 or less.
  • any substance may be used as long as the reaction is suitably allowed to proceed, but the equivalent of the compound (FR-1) to maleic anhydride is 1.0 to 2.0. Is preferable, 1.0 to 1.5 is more preferable, 1.0 to 1.4 is further preferable, and 1.0 to 1.2 is particularly preferable.
  • the upper limit is preferably 2.0 or less, more preferably 1.5 or less, further preferably 1.4 or less, and particularly preferably 1.2 or less.
  • reaction B2 The composition containing the compounds (DA-1) and (DA-2) obtained in the reaction A2 is subjected to a ring-opening dehydration reaction to produce a composition containing the compounds (PA-1) and (PA-2). can do.
  • the reaction solvent may be any one as long as it allows the reaction to proceed suitably, but water, acetonitrile, toluene, xylene, alkylbenzene, or a mixed solvent of each, or no solvent is preferable.
  • the reaction temperature may be any as long as it allows the reaction to proceed suitably, but is preferably 20 to 150 ° C, more preferably 30 to 120 ° C, and even more preferably 40 to 100 ° C.
  • the lower limit value is preferably 20 ° C. or higher, preferably 25 ° C. or higher, preferably 30 ° C. or higher, preferably 35 ° C. or higher, and preferably 40 ° C. or higher.
  • the upper limit value is preferably 150 ° C. or lower, preferably 140 ° C. or lower, preferably 130 ° C. or lower, preferably 120 ° C. or lower, preferably 110 ° C. or lower, and preferably 100 ° C. or lower. It is preferable to use a catalyst for the above reaction.
  • the catalyst may be any one as long as it allows the reaction to proceed appropriately, but hydrochloric acid, sulfuric acid, p-toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, polyphosphoric acid, diphosphate, trifluoroacetic acid, etc. Or the following formula (AC)
  • X represents -OH, -ONa, -OK, -R 5
  • R 5 has the same meaning as R 1 to R 4
  • Y represents a sulfur atom or a phosphorus atom
  • Z represents a hydrogen atom.
  • -COR 6 , -COH or -CO-CF 3 is represented, and R 6 has the same meaning as R 1 to R 4 above. It is preferably a compound represented by.
  • the amount of the catalyst is preferably 0.1 to 3000 mol%, preferably 0.5 to 2500 mol%, and 1 to 1 to the total amount of the compounds represented by the formulas (DA-1) and (DA-2).
  • 2000 mol% is preferable, 5 to 1500 mol% is preferable, 10 to 1000 mol% is preferable, 20 to 500 mol% is preferable, 50 to 500 mol% is preferable, 70 to 500 mol% is preferable, 100 to 500 mol% is preferable, and 150 to 500 mol% is preferable.
  • the lower limit is preferably 0.1 mol% or more, preferably 0.5 mol% or more, preferably 1 mol% or more, preferably 5 mol% or more, preferably 10 mol% or more, preferably 20 mol% or more, preferably 50 mol% or more, and 70 mol. % Or more is preferable, 100 mol% or more is preferable, 150 mol% or more is preferable, 200 mol% or more is preferable, 250 mol% or more is preferable, and 300 mol% or more is preferable.
  • the upper limit value is preferably 3000 mol% or less, preferably 2500 mol% or less, preferably 2000 mol% or less, preferably 1500 mol% or less, preferably 1000 mol% or less, and preferably 500 mol% or less. These upper and lower limit values are used in any combination.
  • reaction C2 A compound selected from the compound group represented by the formula (I) is prepared by reacting the composition containing the compounds (PA-1) and (PA-2) obtained in the reaction B2 with urea and MX in the presence of a catalyst.
  • the reaction solvent may be any one as long as it allows the reaction to proceed suitably, but solvent-free and alkylbenzene are preferable.
  • the reaction temperature may be any as long as it allows the reaction to proceed suitably, but it is preferably 100 to 250 ° C, preferably 110 to 240 ° C, preferably 120 to 230 ° C, preferably 130 to 220 ° C, and 140 to 210.
  • the temperature is preferably 150 to 200 ° C.
  • the lower limit value is preferably 100 ° C. or higher, preferably 110 ° C. or higher, preferably 120 ° C. or higher, preferably 130 ° C. or higher, preferably 140 ° C. or higher, and preferably 150 ° C. or higher.
  • the upper limit is preferably 250 ° C. or lower, preferably 240 ° C. or lower, preferably 230 ° C. or lower, preferably 220 ° C.
  • M represents a metal atom, it is preferably Al, Si, Sc, Ti, V, Mg, Fe, Co, Ni, Cu, Zn, Ga, Ge, Y, Zr, Nb, In, Sn or Pb. , Al, Fe, Cu, Zn, more preferably Cu, Zn.
  • the catalyst may be any catalyst that allows the reaction to proceed suitably, but a molybdenum catalyst is preferable, and ammonium molybdenum (IV) acid tetrahydrate is more preferable.
  • a molybdenum catalyst is preferable, and ammonium molybdenum (IV) acid tetrahydrate is more preferable.
  • reaction D2 The compound represented by the formula (I) obtained in the reaction C2 is contained in one or more kinds, and is represented by the formulas (IA), (IB), (IC), (ID) and (IE).
  • a composition containing one or more compounds selected from the group contains one or more compounds represented by the formula (II) by carrying out a demetallization reaction, and the above formula (IIA).
  • (IIB), (IIC), (IID) and (IIE) can be used to produce a composition containing one or more compounds selected from the compound group.
  • the demetallization reaction may be any reaction as long as it proceeds favorably, and examples thereof include the method described in Chemcomm Communication, 2009, 1970-1971.
  • the phthalocyanine composition contains one or more compounds selected from the group of compounds represented by the formulas (I) and (II), and the compounds represented by the formulas (IA) to (IIE).
  • Bromine atom is preferred, hydrogen atom, linear or branched alkyl group having 1 to 12 carbon atoms, chlorine atom, bromine atom is more preferable, hydrogen atom, linear or branched alkyl group having 1 to 12 carbon atoms. , Bromine atom is more preferable, and hydrogen atom and bromine atom are particularly preferable.
  • M is preferably Al, Si, Sc, Ti, V, Mg, Fe, Co, Ni, Cu, Zn, Ga, Ge, Y, Zr, Nb, In, Sn or Pb, and is preferably Al, Fe, Cu. , Zn is more preferable, and Cu and Zn are even more preferable.
  • the compound selected from the compound group represented by (IA) to (IIE) is preferably a compound selected from the compound group represented by (IA) to (IID), and is preferably a compound selected from the compound group represented by (IA) to (IID). It is more preferably a compound selected from the compound group represented by IIC), and further preferably a compound selected from the compound group represented by (IA) and (IIA).
  • the content of the compounds represented by (IA) to (IIE) is preferably 0.1 to 40% by weight, preferably 0.1 to 30% by weight, and 0.1 to 20% by weight. Is more preferably, 0.1 to 15% by weight is further preferable, and 0.1 to 10% by weight is particularly preferable.
  • the lower limit is preferably 0.1% by weight or more, preferably 0.5% by weight or more, more preferably 1.0% by weight or more, and 1.5% by weight or more. Is more preferable, and 2.0% by weight or more is particularly preferable.
  • the upper limit is preferably 40% by weight or less, preferably 30% by weight or less, more preferably 20% by weight or less, still more preferably 15% by weight or less, and 10% by weight or less. Is particularly preferable.
  • the compounds represented by the following formulas (I-1) to (I-12) are preferable.
  • RI has the same meaning as R1 to R4
  • M has the same meaning as M.
  • the compound represented by the formula (I) is not limited, and examples thereof include compounds represented by the following formulas (I-1) to (I-12-2).
  • the compounds represented by the following formulas (II-1) to (II-12) are preferable.
  • RI has the same meaning as R1 to R4
  • M has the same meaning as M.
  • the compound represented by the formula (II) is not limited, and examples thereof include compounds represented by the following formulas (II-1) to (II-12-2).
  • the compound represented by the above formulas (II-1) to (II-12) is preferable.
  • the compounds represented by the above formulas (IA-1-1) to (IE-1--4) include (IA-1-2), (IB-1-2), (IC-1-2), and (ID).
  • the compounds represented by 1-2) and (IE-1-2) are preferable.
  • As the compound, (IA-1-2) to (ID-1-2) are preferable, (IA-1-2) to (IC-1-2) are more preferable, and (IA-1-2) is further preferable. preferable.
  • the compounds represented by the formulas (IIA), (IIB), (IIC), (IID) and (IIE) the compounds represented by the following formulas (IIA-1) to (IIE-1) are preferable.
  • the compounds represented by the above formulas (IIA-1) to (IIE-1) are preferable, and the compounds represented by the following formulas (IIA-1) to (IIC-1) are preferable.
  • the compound represented by 1) is more preferable, and the compound represented by (IIA-1) is further preferable.
  • the compounds represented by the formulas (IA) to (IIE) can control pigment crystallization, resin dispersibility and hue, leading to higher performance of the phthalocyanine composition.
  • the compound represented by the formula (I), (II) or (IA) to (IIE) produced by the above method is further purified by a known and commonly used method, and the compound represented by the formula (I) or (II) is further purified. It is also possible to take out only.
  • the compound contained in the substance can be further halogenated, sulfonated, or imidized by a known and commonly used method.
  • the phthalocyanine compound and composition produced by the production method of the present invention particularly exhibit properties as an organic pigment, and may be more preferably used by finely dividing the pigment particles.
  • Such treatment can be selected from, for example, an acid paste method, an acid slurry method, a dry milling method, a solvent method, a salt milling method, or the like, one or a plurality of combinations.
  • the phthalocyanine compound and composition produced by the production method of the present invention may be used in combination with additional coloring materials such as organic pigments, organic dyes and organic pigment derivatives for the purpose of color matching and the like. These should be appropriately selected according to the above-mentioned uses, and depending on the use, the phthalocyanine compound and the composition produced by the production method of the present invention may be used alone or in combination of two or more.
  • any known pigment dye or the like may be used.
  • the phthalocyanine compound and composition produced by the production method of the present invention can be used as cosmetics.
  • the cosmetics used are not particularly limited, and the water-insoluble dye composition of the present invention can be used for various types of cosmetics.
  • the cosmetics may be any type of cosmetics as long as they can effectively exhibit their functions.
  • the cosmetic may be a lotion, cream gel, spray or the like.
  • the cosmetics include skin care cosmetics such as face wash, makeup remover, lotion, beauty liquid, pack, protective milky lotion, protective cream, whitening cosmetics, UV protection cosmetics, foundation, white powder, makeup base, lipstick, eye makeup, etc.
  • Makeup cosmetics such as cheek red and nail enamel, shampoo, hair rinse, hair treatment, hair conditioner, permanent wave agent, hair dye, hair restorer and other hair care cosmetics, body cleansing cosmetics, deodorant cosmetics, bathing agents and other body care Cosmetics and the like can be mentioned.
  • the amount of the phthalocyanine compound and the composition produced by the production method of the present invention used in the cosmetics can be appropriately set according to the type of cosmetics.
  • the content in the cosmetics is usually in the range of 0.1 to 99% by mass, and generally preferably in the range of 0.1 to 10% by mass.
  • the amount is preferably in the range of 5 to 80% by mass, more preferably in the range of 10 to 70% by mass, and most preferably in the range of 20 to 60% by mass. Is preferable.
  • the amount of the phthalocyanine compound and the composition produced by the production method of the present invention contained in the cosmetics is within the above range, the functions such as colorability can be effectively exhibited and the functions required for the cosmetics are also maintained. can do.
  • the content in the cosmetics is usually in the range of 0.1 to 99% by mass, and generally preferably in the range of 0.1 to 10% by mass.
  • the amount is preferably in the range of 5 to 80% by mass, more preferably in the range of 10 to 70% by mass
  • the cosmetics include carriers, pigments, oils, sterols, amino acids, moisturizers, powders, which are acceptable as cosmetic ingredients, depending on the type of cosmetics.
  • the cosmetic product can be produced by mixing the phthalocyanine compound and the composition produced by the production method of the present invention and other cosmetic ingredients.
  • the cosmetics containing the phthalocyanine compound and the composition produced by the production method of the present invention can be used in the same manner as ordinary cosmetics depending on the type of the cosmetics and the like.
  • the phthalocyanine compound and composition produced by the production method of the present invention can produce low-viscosity inks having excellent fluidity, and are suitable as pigments for gravure printing inks and flexographic printing inks.
  • the ink consists of a binder resin, a solvent, a pigment, and various additives.
  • Binder resins include, for example, nitrocellulose resin, polyamide resin, polyurethane resin, acrylic resin, and solvents include aromatic organic solvents such as toluene and xylene, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, 2-heptanone, 3-.
  • Ketone-based solvents such as heptanone, ester-based solvents such as ethyl acetate, n-propyl acetate, isopropyl acetate, and isobutyl acetate, alcohol-based solvents such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, and t-butanol.
  • Glycol ether-based solvents, additives include anionic, nonionic, cationic, amphoteric and other surfactants, gum rosin, polymerized rosin, disproportionated rosin, hydrogenated rosin, maleated rosin, cured rosin, Rodins such as phthalic acid alkyd resin, pigment derivatives, dispersants, wetting agents, adhesive aids, leveling agents, defoaming agents, antistatic agents, trapping agents, antiblocking agents, wax components and the like can be used.
  • the printing ink prepared as described above can be used for printing on paper, synthetic paper, thermoplastic resin film, plastic products, steel plates, etc., and is used for gravure printing using a gravure printing plate using an electronic engraving concave plate or the like. , Or as an ink for flexographic printing using a flexographic printing plate using a resin plate or the like.
  • the printing ink is obtained by first adhering and transferring the printing ink to a printing plate or a printing pattern, then adhering only the ink to the substrate again, and drying it as necessary to obtain a printed matter.
  • the printed matter can also be used as a component of a laminated body with another base material or the like.
  • the resins used as the paint include acrylic resin, melamine resin, epoxy resin, polyester resin, polyurethane resin, polyamide resin, and phenol. There are various types such as resin.
  • the solvent used for the paint includes aromatic solvents such as toluene, xylene and methoxybenzene, acetate solvents such as ethyl acetate, butyl acetate, propylene glycol monomethyl ether acetate and propylene glycol monoethyl ether acetate, and ethoxyethyl pro.
  • aromatic solvents such as toluene, xylene and methoxybenzene
  • acetate solvents such as ethyl acetate, butyl acetate, propylene glycol monomethyl ether acetate and propylene glycol monoethyl ether acetate, and ethoxyethyl pro.
  • Propionate-based solvents such as pionate, alcohol-based solvents such as methanol, ethanol, propanol, n-butanol, and isobutanol, ether-based solvents such as butyl cellosolve, propylene glycol monomethyl ether, diethylene glycol ethyl ether, and diethylene glycol dimethyl ether, methyl ethyl ketone, and methyl isobutyl ketone.
  • Ketone solvent such as cyclohexanone, aliphatic hydrocarbon solvent such as hexane, nitrogen compound solvent such as N, N-dimethylformamide, ⁇ -butyrolactam, N-methyl-2-pyrrolidone, aniline, pyridine, ⁇ -butyrolactone
  • lactone-based solvents such as, carbamate esters such as a 48:52 mixture of methyl carbamate and ethyl carbamate, water and the like.
  • a water-soluble polar solvent such as propionate-based, alcohol-based, ether-based, ketone-based, nitrogen compound-based, lactone-based, and water is particularly suitable.
  • pigment additive and / or the pigment composition is dispersed or mixed in a liquid resin to obtain a resin composition for a paint
  • ordinary additives such as dispersants, fillers and paints are used.
  • Auxiliary agents, desiccants, plasticizers and / or auxiliary pigments can be used. This is achieved by dispersing or mixing each component, either alone or in combination, collecting all the components, or adding them all at once.
  • Dispersers for dispersing the phthalocyanine compound and the composition containing the composition produced by the production method of the present invention prepared according to the above-mentioned applications include a disper, a homomixer, a paint conditioner, a scandex, a bead mill, and an atom.
  • the pigment composition is dispersed by adding a resin and a solvent so as to have a viscosity that can be dispersed by these dispersers.
  • the high-concentration paint base after dispersion has a solid content of 5 to 20%, and is further mixed with a resin and a solvent to be used as a paint.
  • the phthalocyanine compound and composition produced by the production method of the present invention can be suitably used for ink jet inks, and are particularly suitable for water-based inkjet inks as an aqueous pigment dispersion liquid dispersed using a pigment dispersant or the like. Can be used for.
  • aqueous pigment dispersion a high-concentration water dispersion (pigment paste) of the condensed polycyclic organic pigment of the present invention is prepared, diluted with a water-soluble solvent and / or water, and other additions are made as necessary. It can be prepared by adding an agent.
  • the method for obtaining a pigment paste by dispersing the phthalocyanine compound and the composition produced by the production method of the present invention in the water-soluble solvent and / or water is not particularly limited, and it is preferable to use a known dispersion method.
  • a known pigment dispersant may be used to disperse in water, or a surfactant may be used.
  • Aqueous resins are preferable as the pigment dispersant, and preferred examples thereof include polyvinyl alcohols, polyvinylpyrrolidones, urethane resins having anionic or cationic groups, and radical copolymers having anionic or cationic groups. Examples include resin.
  • radical copolymer resin having an anionic group or a cationic group examples include acrylic resins such as acrylic acid-acrylic acid ester copolymers, styrene-acrylic acid copolymers, and styrene-methacrylic acid copolymers.
  • Styline-acrylic resin such as styrene-methacrylic acid-acrylic acid ester copolymer, styrene- ⁇ -methylstyrene-acrylic acid copolymer, styrene- ⁇ -methylstyrene-acrylic acid-acrylic acid ester copolymer, styrene- Examples thereof include a maleic acid copolymer, a styrene-maleic anhydride copolymer, a vinylnaphthalene-acrylic acid copolymer, and a salt of the aqueous resin.
  • Examples of the compound for forming the salt of the copolymer include alkali metals hydroxides such as sodium hydroxide, potassium hydroxide and lithium hydroxide, and diethylamine, ammonia, ethylamine, triethylamine, propylamine, isopropylamine and di. Examples thereof include propylamine, butylamine, isobutylamine, triethanolamine, diethanolamine, aminomethylpropanol and morpholin.
  • the amount of the compound used to form these salts is preferably equal to or more than the neutralization equivalent of the copolymer. Of course, it is also possible to use a commercially available product.
  • the following (1) to (3) can be shown.
  • (2) The pigment and the pigment dispersant are kneaded using a kneader such as a two-roll or mixer, the obtained kneaded product is added to an aqueous medium containing water, and the pigment is used with a stirring / dispersing device. How to prepare a paste.
  • the kneading machine is not particularly limited, and examples thereof include a Henschel mixer, a pressurized kneader, a Banbury mixer, and a planetary mixer.
  • the stirring / dispersing device is also not particularly limited, and examples thereof include an ultrasonic homogenizer, a high-pressure homogenizer, a paint shaker, a ball mill, a roll mill, a sand mill, a sand grinder, a dyno mill, a dispermat, an SC mill, and a nanomizer.
  • One of these may be used alone, or two or more kinds of devices may be used in combination.
  • the amount of the condensed polycyclic organic pigment in the pigment paste is preferably 5 to 60% by mass, more preferably 10 to 50% by mass.
  • the amount of the pigment is less than 5% by mass, the water-based ink prepared from the pigment paste is not sufficiently colored, and a sufficient image density tends not to be obtained.
  • the dispersion stability of the pigment tends to decrease in the pigment paste.
  • an impurity removal step by ion exchange treatment or extra treatment may be performed, and then post-treatment may be performed.
  • Ionic substances such as cations and anions (divalent metal ions, etc.) can be removed by ion exchange treatment, and impurity-dissolving substances (residual substances during pigment synthesis, excess components in the dispersion liquid composition) can be removed by extraneous treatment.
  • Resin not adsorbed on organic pigments, foreign substances mixed in, etc. can be removed.
  • a known ion exchange resin is used for the ion exchange treatment.
  • the ultrafiltration may be performed using a known ultrafiltration membrane and may be either a normal type or a double capacity up type.
  • aqueous pigment dispersion liquid After preparing the pigment paste, dilute it appropriately and add an additive if necessary to obtain an aqueous pigment dispersion liquid according to the purpose.
  • a water-soluble solvent and / or water, an anionic group-containing organic polymer compound for the purpose of a binder, etc. are further added, and a wetting agent is added as necessary to obtain desired physical properties.
  • a wetting agent is added as necessary to obtain desired physical properties.
  • a centrifugation or filtration treatment step may be added.
  • the physical characteristics of the ink are not particularly limited, but the viscosity is preferably 1 to 10 (mPa ⁇ s) and the surface tension is preferably 20 to 50 (mN / m) in consideration of the ejection property of the inkjet ink.
  • the pigment concentration is preferably 1 to 10% by mass.
  • the wetting agent is added for the purpose of preventing the ink from drying.
  • the content of the wetting agent for the purpose of preventing drying in the ink is preferably 3 to 50% by mass.
  • the wetting agent used in the present invention is not particularly limited, but one that is miscible with water and has an effect of preventing clogging of the head of an inkjet printer is preferable.
  • glycerin ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol having a molecular weight of 2000 or less
  • propylene glycol dipropylene glycol, tripropylene glycol, 1,3-propylene glycol, isopropylene glycol, isobutylene glycol, 1,4-butane.
  • examples thereof include diol, 1,3-butanediol, 1,5-pentanediol, 1,6-hexanediol, mesoerythritol, pentaerythritol and the like.
  • the inclusion of propylene glycol and 1,3-butyl glycol has safety, and has excellent effects of ink drying property and ejection performance.
  • the penetrant is added for the purpose of improving the permeability to the recording medium and adjusting the dot diameter on the recording medium.
  • the penetrant include lower alcohols such as ethanol and isopropyl alcohol, ethylene oxide adducts of alkyl alcohols such as ethylene glycol hexyl ether and diethylene glycol butyl ether, and propylene oxide adducts of alkyl alcohols such as propylene glycol propyl ether.
  • the surfactant is added to adjust ink characteristics such as surface tension.
  • the surfactant that can be added for this purpose is not particularly limited, and examples thereof include various anionic surfactants, nonionic surfactants, cationic surfactants, and amphoteric surfactants. Of these, anionic surfactants and nonionic surfactants are preferable.
  • anionic surfactant examples include alkylbenzene sulfonates, alkylphenylsulfonates, alkylnaphthalene sulfonates, higher fatty acid salts, sulfate ester salts of higher fatty acid esters, sulfonates of higher fatty acid esters, and higher alcohol ethers. Sulfate ester salts and sulfonates, higher alkyl sulfosuccinates, polyoxyethylene alkyl ether carboxylates, polyoxyethylene alkyl ether sulfates, alkyl phosphates, polyoxyethylene alkyl ether phosphates and the like.
  • nonionic surfactant examples include polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene sorbitol fatty acid ester, and glycerin fatty acid ester.
  • Polyoxyethylene glycerin fatty acid ester Polyglycerin fatty acid ester, polyglycerin fatty acid ester, sucrose fatty acid ester, polyoxyethylene alkylamine, polyoxyethylene fatty acid amide, fatty acid alkylolamide, alkylalkanolamide, acetylene glycol, oxyethylene adduct of acetylene glycol, Examples thereof include polyethylene glycol polypropylene glycol block copolymers, among which polyoxyethylene nonylphenyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene dodecylphenyl ether, polyoxyethylene alkyl ether, and polyoxyethylene fatty acid.
  • Esters sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, fatty acid alkyrrole amides, acetylene glycols, oxyethylene adducts of acetylene glycol, polyethylene glycol polypropylene glycol block copolymers are preferred.
  • surfactants include silicone surfactants such as polysiloxane oxyethylene adducts; fluorosurfactants such as perfluoroalkyl carboxylates, perfluoroalkyl sulfonates and oxyethylene perfluoroalkyl ethers. Biosurfactants such as spicrysporic acid, ramnolipide, lysolecithin and the like can also be used.
  • surfactants can be used alone or in combination of two or more.
  • the amount of the surfactant added is preferably in the range of 0.001 to 2% by mass, more preferably 0.001 to 1.5% by mass, and 0. It is more preferably in the range of 01 to 1% by mass. If the amount of the surfactant added is less than 0.001% by mass, the effect of adding the surfactant tends not to be obtained, and if it is used in excess of 2% by mass, problems such as blurring of the image are likely to occur. ..
  • the phthalocyanine compound and composition produced by the production method of the present invention can also be used for plastic coloring.
  • a thermoplastic resin (plastic) for thermal molding such as injection molding and press molding such as polyolefin such as polyethylene and polypropylene and polyvinyl chloride resin is used.
  • the phthalocyanine compound and the composition produced by the production method can be used by kneading them into these resins by a conventionally known method.
  • the phthalocyanine compound and composition produced by the production method of the present invention can also be used for toner coloring.
  • a thermoplastic resin having a solid film-forming property at room temperature such as a polyester resin, a polyamide resin, a styrene resin, and an acrylic resin, is used as the dispersion resin.
  • the static charge image developing toner produced by using the phthalocyanine compound and the composition produced by the production method of the present invention as constituent components is a one-component color magnetic toner (color toner for magnetic one-component development) containing a magnetic substance in the toner.
  • a one-component color magnetic toner color toner for magnetic one-component development
  • the one-component color magnetic toner can be composed of, for example, a colorant, a binder resin, a magnetic powder, a charge control agent (CCA), and other additives typified by a mold release agent, in the same manner as those normally used.
  • CCA charge control agent
  • the amount of the composition of the present invention to be used in the toner for static charge image development is not particularly limited, but it is preferably used in a ratio of 0.5 to 25 parts by mass with respect to 100 parts by mass of the binder resin, and the colorant itself. It is more preferably 4 to 10 parts by mass with respect to 100 parts by mass of the binder resin from the viewpoint of making the charging performance of the binder more remarkable.
  • thermoplastic resin any of the known and commonly used resins exemplified as the thermoplastic resin can be used, but synthetic resins and natural resins that exhibit adhesiveness under the application of heat or pressure, Natural rubber, synthetic rubber, synthetic wax, etc. can be used.
  • the phthalocyanine compound and composition produced by the production method of the present invention can be used for forming a pattern of a green pixel portion of a color filter by a known method.
  • a photosensitive composition for a green pixel portion of a color filter containing a phthalocyanine compound and composition produced by the production method of the present invention and a photosensitive resin as essential components can be obtained.
  • a photosensitive composition for a green pixel portion of a color filter for example, a phthalocyanine compound and composition produced by the production method of the present invention, a photosensitive resin, a photopolymerization initiator, and an organic substance that dissolves the resin are used. Mix with solvent as an essential ingredient.
  • a dispersion liquid is prepared using the phthalocyanine compound and composition produced by the production method of the present invention, an organic solvent, and a dispersant as necessary, and then a photosensitive resin or the like is added thereto.
  • the method of doing is common.
  • a yellow pigment can be used for the phthalocyanine compound and the composition produced by the production method of the present invention used for the photosensitive composition for the green pixel portion of the color filter.
  • the dispersant used as needed include Disperbic (DISPERBYK registered trademark) 130, 161 and 162, 163, 170, LPN-6919 and LPN-21116 of Big Chemie. Further, a leveling agent, a coupling agent, a cationic surfactant and the like can also be used.
  • organic solvent examples include aromatic solvents such as toluene, xylene and methoxybenzene, acetate solvents such as ethyl acetate, butyl acetate, propylene glycol monomethyl ether acetate and propylene glycol monoethyl ether acetate, and ethoxyethyl propionate.
  • aromatic solvents such as toluene, xylene and methoxybenzene
  • acetate solvents such as ethyl acetate, butyl acetate, propylene glycol monomethyl ether acetate and propylene glycol monoethyl ether acetate, and ethoxyethyl propionate.
  • Propionate solvent alcohol solvent such as methanol and ethanol, ether solvent such as butyl cellosolve, propylene glycol monomethyl ether, diethylene glycol ethyl ether and diethylene glycol dimethyl ether, ketone solvent such as methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone, fat such as hexane.
  • alcohol solvent such as methanol and ethanol
  • ether solvent such as butyl cellosolve
  • propylene glycol monomethyl ether diethylene glycol ethyl ether and diethylene glycol dimethyl ether
  • ketone solvent such as methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone
  • fat such as hexane.
  • Group hydrocarbon solvents N, N-dimethylformamide, ⁇ -butyrolactam, N-methyl-2-pyrrolidone, aniline, pyridine and other nitrogen compound solvents, ⁇ -butyrolactone and other lactone solvents, methyl carbamate and carbamate
  • carbamates water and the like, such as a 48:52 mixture of ethyls.
  • organic solvent a water-soluble polar solvent such as propionate-based, alcohol-based, ether-based, ketone-based, nitrogen compound-based, lactone-based, or water is particularly suitable.
  • thermoplastic resins such as urethane resin, acrylic resin, polyamic acid resin, polyimide resin, styrene maleic acid resin, and styrene anhydride maleic acid resin, and examples of 1,6.
  • -Bifunctional monomers such as hexanediol diacrylate, ethylene glycol diacrylate, neopentyl glycol diacrylate, triethylene glycol diacrylate, bis (acryloxyethoxy) bisphenol A, 3-methylpentanediol diacrylate, etc., trimethylolpropane
  • photopolymerizable monomers such as polyfunctional monomers such as triacrylate, pentaerythritol triacrylate, tris (2-hydroxyethyl) isocyanate, dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate and the like.
  • photopolymerization initiator examples include acetophenone, benzophenone, benzyldimethylketal, benzoyl peroxide, 2-chlorothioxanthone, 1,3-bis (4'-azidobenzal) -2-propane, and 1,3-bis (4'-. Azidobenzal) -2-propane-2'-sulfonic acid, 4,4'-diazidostilbene-2,2'-disulfonic acid and the like.
  • the photosensitive composition for the green pixel portion prepared in this way is formed into a color filter by subjecting the unexposed portion to a pattern exposure with ultraviolet rays via a photo mask and then washing the unexposed portion with an organic solvent, alkaline water, or the like. Can be done.
  • Example 1 Synthesis of phthalocyanine composition (Pc-1) from a mixture of compound (DA-1-1) and compound (DA-2-1) A stirrer, a thermometer, a dropping funnel, and a cooling tube were provided. Acetic anhydride (21.0 g) and methanesulfonic acid (148.0 g) were added to the reaction vessel, and the mixture was ice-cooled with stirring. A mixture (10.0 g) of the compound (DA-1-1) and the compound (DA-2-1) obtained in Synthesis Example 1 was slowly added dropwise to the reaction mixture. After stirring at room temperature for 2 hours, the temperature was raised to 80 ° C. and the mixture was further stirred for 4 hours.
  • Pc-1 contains 94.6% of the compound represented by the above formula (I-1-2) and 2.8% of the compound represented by the above formula (IA-1-2). It was found to contain. Further, Pc-2 contains 86.3% of the compound represented by the above formula (I-1-2), 12.0% of the compound represented by the above formula (IA-1-2), and the above formula (IB-). It was found that the compound represented by 1-2) or (IC-1-2) was contained in 0.4%.
  • the copper phthalocyanine composition produced by the production method of the embodiment of the present invention has a smaller particle size after pigmentation as compared with the copper phthalocyanine produced by the production method of the comparative example. Therefore, the dispersibility in the resin and the brightness can be improved, leading to higher performance.
  • the furan used in Synthesis Example 1 is derived from biomass, and the phthalocyanine compound and composition produced by the production method of the example of the present invention can improve the degree of biomass.
  • by introducing a substituent into the furan of the raw material used in Synthesis Example 1 it is possible to produce phthalocyanine while controlling the substitution position and number according to the examples.

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