WO2013075286A1 - Composé d'acide anthracènepyridinesulfonique binucléaire ou sel de celui-ci et son procédé de préparation et son utilisation - Google Patents

Composé d'acide anthracènepyridinesulfonique binucléaire ou sel de celui-ci et son procédé de préparation et son utilisation Download PDF

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WO2013075286A1
WO2013075286A1 PCT/CN2011/082623 CN2011082623W WO2013075286A1 WO 2013075286 A1 WO2013075286 A1 WO 2013075286A1 CN 2011082623 W CN2011082623 W CN 2011082623W WO 2013075286 A1 WO2013075286 A1 WO 2013075286A1
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Prior art keywords
salt
compound
sulfonic acid
formula
dinuclear
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PCT/CN2011/082623
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English (en)
Chinese (zh)
Inventor
彭孝军
吴金河
樊江莉
孟凡明
宋锋玲
孙世国
张蓉
王静月
龙志
王力成
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大连理工大学
大连福思达专用化学有限公司
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Priority to PCT/CN2011/082623 priority Critical patent/WO2013075286A1/fr
Publication of WO2013075286A1 publication Critical patent/WO2013075286A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • 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
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
    • C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
    • C09B1/34—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated
    • C09B1/343—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated only sulfonated in the anthracene nucleus
    • 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
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/02—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position
    • C09B5/14—Benz-azabenzanthrones (anthrapyridones)

Definitions

  • the present invention relates to a structure of a class of dinuclear pyridinone sulfonic acid compounds, a process for synthesizing such a binuclear pyridinone sulfonic acid compound, and a magenta ink containing such a binuclear pyridinone sulfonic acid compound for ink jet printing. Background technique
  • the inkjet printing method is one of the typical color recording methods. Since the head does not come into contact with the material to be recorded, it is quiet without sound, and it is easy to be miniaturized, speeded up, and colored, and has been rapidly developed in recent years.
  • inks for ink jet printing are generally produced by dissolving a water-soluble dye in an aqueous medium and adding a water-soluble organic solvent which prevents clogging of the pen tip and the ink jet nozzle ink.
  • These inks are required to have a high-density printed image, a tip or nozzle that does not block, a good drying property on a book recording material, a small penetration, and excellent storage stability.
  • the formed image must have water resistance and light resistance. Fastness to sex, moisture resistance, etc.
  • ink water resistance Usually, the surface of the substrate is adsorbed by porous silica, cationic polymer, alumina sol or special ceramic.
  • the dye is coated on the paper surface together with these organic or inorganic particles and PVA resin. The ground is improved.
  • moisture resistance When the printed image is stored in a high humidity environment, the penetration of the dye in the recorded material is fast, if there is penetration of the dye, especially in the case of high photo coloring requirements, Will significantly reduce the image quality.
  • light resistance The four primary colors of yellow, magenta, cyan, and black have the weakest light resistance, and this improvement has become an important issue.
  • ozone gas is a main substance for promoting oxidation and fading of ink-jet printed images. Therefore, improvement of ozone-resistant gas properties is also an important issue in improving light resistance.
  • the molecular skeleton of the dye for magenta used in the inkjet ink is represented by an oxazepine type rhodamine dye and an azo type dye coupled by H acid.
  • the rhodamine dye is excellent in color tone and vividness, but its light resistance is extremely poor.
  • the H-acid azo dye although the color and water resistance are good, the light resistance, the ozone resistance, and the vividness are insufficient, especially compared with the cyan dye and the azo yellow dye represented by copper phthalocyanine. , light resistance is still insufficient.
  • the present invention has been made in order to solve the above problems, and it has been found that an sulfonic acid compound of anthrapyridone can solve the above problems.
  • the present invention first provides a class of dinuclear anthrapyridone sulfonic acid compounds or salts thereof having the structure of formula I:
  • L is a linking group
  • R 7 is a CM group
  • n is an integer of 0-2;
  • n is an integer from 0-3.
  • the binuclear pyridinone sulfonic acid compound or a salt thereof according to the present invention is - (E-1 to E-10) or a salt thereof:
  • the above-mentioned dinuclear pyridinium sulfonate compound or a salt thereof according to the present invention wherein the salt is a lithium salt, a sodium salt, a potassium salt, an ammonium salt or an organic ammonium salt of the corresponding dinuclear pyridone sulfonic acid compound.
  • the organic ammonium salt cation has a structure of the general formula N + R 3 R4R 5 R 6 wherein R 3 , R 5 , R 6 are each independently selected from the group consisting of 11, C M8 fluorenyl, cyclohexyl, CH 2 CH 2 OH and benzyl.
  • the salt of the dinuclear pyridone sulfonic acid compound is a lithium salt, a sodium salt, a potassium salt, an ammonium salt, a monoethanolamine salt, a diethanolamine salt, a triethanolamine salt, a single of the corresponding dinuclear pyridone sulfonic acid compound.
  • the salt is a lithium, sodium or ammonium salt of the corresponding dinuclear pyridone sulfonic acid compound.
  • Another object of the present invention is to provide a process for producing the above-described dinuclear pyridinone sulfonic acid compound of the present invention or a salt thereof, comprising the steps of:
  • the organic solvent is xylene, diethylbenzene, trimethylbenzene, chlorobenzene, dichlorobenzene, nitrobenzene or a mixed solvent of DMF and DMSO in a volume ratio of 3:1;
  • a compound of the formula VI is prepared by reacting a compound of the formula V with a cyanuric chlorination ratio of 1:1 in an anionic emulsifier with a 25 % aqueous sodium hydroxide solution at a pH of 3-4 for 3 hours.
  • R is selected from the group consisting of: OH, O(C 6 H 5-m )(CO 2 H) m S(CH 2 ) m SO 3 H, S(CH 2 ) m CO 2 H, O(C 6 H 5- m )(SO 3 H) m , O(C 10 H 9-m )(CO 2 H) m , O(C 10 H 9-m )(SO 3 H) m , leg 2 , grass 7 ) 2 , SH , SR 7 , NH(C 6 H 5-m )(CO 2 H) m , NH(C 6 H 5-m )(SO 3 H) m , NH(C 10 H 9-m )(CO 2 H) m , NH(C 10 H 9-m )(SO 3 H) m , S(C 6 H 5-m )(CO 2 H) m , S(C 6 H 5-m )(SO 3 H) m , S(C 6 H 5-m )(CO
  • p, q are integers from 1 to 18.
  • a further object of the present invention is to provide a magenta ink composition comprising the above-described dinuclear pyridone sulfonic acid compound of the present invention or a salt thereof.
  • the magenta ink composition contains water and a water-soluble organic solvent.
  • the mass percentage of the dinuclear pyridone sulfonic acid compound in the magenta ink composition is 0.1 to 20%.
  • the mass percentage of inorganic impurities in the magenta ink composition does not exceed 1% of the total mass of the non-solvent component.
  • Another object of the present invention is also to provide the use of the magenta ink combination of the present invention described above in ink jet printing.
  • the present invention introduces an electron-absorbing water-soluble group sulfonic acid group on the anthracene ring of the dinuclear pyridone, which has not appeared in the prior art in the prior art, and can not only reduce the electron cloud density of the molecule, but also improve the light resistance. Oxidation and ozone oxidation, and can improve the solubility of the dye, enhance the stability of the dye in the ink; and the two dye precursors can improve the water resistance of the dye image.
  • the industrial bromate blue dye is used as a starting material, the sulfonic acid compound generally used in the prior art is avoided, the reaction step is small, the process flow is short, and the raw materials are inexpensive, and the compound represented by the formula (I) of the present invention and
  • the magenta ink composition prepared from the salt exhibits a sharp color and an extremely high color tone on the ink jet recording paper, and is excellent in water solubility, and has good filterability to the filter in the production process of the ink composition.
  • the printed matter of the red ink set of the inkjet recording article containing the anthrapyridone compound of the present invention does not select a material to be recorded (paper, film, etc.) to provide an ideal magenta tone, and the magenta of the present invention
  • the ink composition faithfully restores the color tone of the color tone of the photo tone, and is light-resistant and resistant even when printed on a surface coated with inorganic fine particles such as inkjet paper (film) for photo quality.
  • the fastness of ozone, moisture resistance, etc. is good, and the long-term preservation of images is stable.
  • L is a linking group, preferably -NH(CH 2 ) p NH -, -S(CH 2 ) q S- or compound L
  • p and q are integers from 1 to 18, preferably integers from 2 to 6.
  • R n R 2 are each independently selected from the group consisting of: OH, O(C 6 H 5-m )(CO 2 H) m , S(CH 2 ) m SO 3 H, S(CH 2 ) m CO 2 H, O ( C 6 H 5-m )(SO 3 H) m , O(C 10 H 9-m )(CO 2 H) m , O(C 10 H 9-m )(SO 3 H) m , NH 2 , grass 7 ) 2 , SH, SR 7 , NH(C 6 H 5-m )(CO 2 H) m , NH(C 6 H 5-m )(SO 3 H) m , NH(C 10 H 9-m )(CO 2 H) m , NH( C 10 H 9-m )(SO 3 H) m , S(C 6 H 5-m )(CO 2 H) m , S(C 6 H 5-m )(SO 3 H) m , S(C 6
  • R 7 is a CM fluorenyl group; n is an integer of 0-2; m is an integer of 0-3.
  • the sum is the same group selected from the group consisting of: o-OC 6 H 5 (CO 2 H) 2 , S(CH 2 ) 3 SO 3 H and p-OC 6 H 5 SO 3 H.
  • mercapto refers to a straight or branched fluorenyl group.
  • a sulfonic acid group is introduced on the core of the substituted 4-aminopyridinone to increase the water solubility; and the two pyridone sulfonic acid compound cores are further connected by a linking group L to improve water resistance.
  • the compound of the formula I is in practical use, usually in the form of a cationic salt, which is a lithium salt, a sodium salt, a potassium salt, an ammonium salt or an organic ammonium salt of the corresponding dinuclear pyridone sulfonic acid compound,
  • the organic ammonium salt cation has a structure of the general formula N + R 3 R4R 5 R 6 wherein R 3 , R 5 , R 6 are each independently selected from the group consisting of 11, C M8 fluorenyl, cyclohexyl, CH 2 CH 2 OH and benzyl. base.
  • the salt is a lithium salt, a sodium salt, a potassium salt, an ammonium salt, a monoethanolamine salt, a diethanolamine salt, a triethanolamine salt, a monoisopropanol of the corresponding dinuclear pyridone sulfonic acid compound.
  • An amine salt, a diisopropanolamine salt or a triisopropanolamine salt is most preferred.
  • the method for preparing a dinuclear pyridinone sulfonic acid compound of the formula I is cyclized in an organic solvent to form a compound of the formula IV, and then sulfonated and hydrolyzed to form an amino group-containing compound.
  • Formula V which then forms intermediate VI with cyanuric chloride, is then reacted with compound RH to form compound of formula VII, and finally joined by a linker HLH to form compound of formula I.
  • the salt is then converted to form a salt.
  • the reaction conditions of the reaction of the blue sulfonic acid compound (formula III) with benzoyl acetate to form compound IV are: 1 compound III and benzoyl acetate (such as a Ester, ethyl ester, propyl ester, isopropyl ester)
  • the reaction is carried out at a molar ratio of 1: 2 to 5 in an organic solvent at 175 to 180 °C.
  • the molar ratio of the compound III to the benzoyl acetate is preferably 1:3.
  • the benzoyl acetate is preferably exemplified by a methyl ester, an ethyl ester, a propyl ester or an isopropyl ester.
  • the solvent is a mixed solvent of a high boiling organic solvent and DMSO, and these organic solvents are preferably xylene, diethylbenzene, trimethylbenzene, chlorobenzene, dichlorobenzene, nitrobenzene or DMF.
  • the ring-forming reaction of formula III is preferably carried out in the presence of a base selected from the group consisting of sodium carbonate, sodium hydrogencarbonate, potassium carbonate, potassium hydrogencarbonate, lithium carbonate, lithium hydrogencarbonate, ammonium carbonate, ammonium hydrogencarbonate, phosphoric acid.
  • a base selected from the group consisting of sodium carbonate, sodium hydrogencarbonate, potassium carbonate, potassium hydrogencarbonate, lithium carbonate, lithium hydrogencarbonate, ammonium carbonate, ammonium hydrogencarbonate, phosphoric acid.
  • Sodium carbonate and sodium hydrogencarbonate are preferred.
  • the molar ratio of the base added to the compound III is
  • the ring-forming reaction of formula III can increase the temperature of the reaction under pressure or vacuum, optionally from 0.5 to 5 atmospheres.
  • the ring-forming reaction of formula III should be carried out under monitoring, using liquid chromatography or thin layer chromatography to control the disappearance of the blue hydrazine dye compound III as the end of the reaction.
  • the ring-forming reaction of formula III uses a water separator to separate the formed water and ethanol from the reflux condenser to promote completion of the reaction.
  • an organic solvent with a low boiling point of 30 to 150 ° C is advantageous for precipitation.
  • the optional solvents include methanol, ethanol, propanol, isopropanol, acetone, methyl ethyl ketone, diethyl ether, tetrahydrofuran, dioxane, and dichloroformamidine.
  • Sulfonated hydrolysis reaction of the compound of the formula IV In the sulfonation reaction of the compound of the formula IV with fuming sulfuric acid, the content of sulfur trioxide in the fuming sulfuric acid is 5 to 15%, preferably 8 to 13%, and most preferably 9 to 12%. .
  • the reaction can be controlled by phase chromatography or thin layer chromatography to control the endpoint of the reaction.
  • the sulfonated product was poured into ice water with stirring, and the reaction was hydrolyzed at 40 to 60 ° C for 0.1 to 2 hours. Then, ammonium chloride or sodium chloride is added for multiple salting out, cooled, and filtered to obtain a compound of the formula V.
  • the compound of the formula I can be salted by a conventional method, for example, by reacting with potassium hydroxide, lithium hydroxide, aqueous ammonia or an organic amine to obtain a corresponding potassium salt, lithium salt, ammonium salt or organic ammonium salt.
  • a conventional method for example, by reacting with potassium hydroxide, lithium hydroxide, aqueous ammonia or an organic amine to obtain a corresponding potassium salt, lithium salt, ammonium salt or organic ammonium salt.
  • lithium salts, sodium salts, potassium salts, ammonium salts, monoethanolamine salts, diethanolamine salts, triethanolamine salts, monoisopropanolamine salts, diisopropanolamine salts or triisopropanolamine salts are preferred.
  • a lithium salt, a sodium salt or an ammonium salt is particularly preferred.
  • the mass percentage of the inorganic impurities does not exceed 1% of the total mass of the non-solvent component, and the dye may be desalted by a general method such as a high pressure reverse osmosis membrane. .
  • the magenta ink composition of the present invention is a composition obtained by dissolving a compound of the formula I or a salt thereof in water or an aqueous solvent.
  • the content of the dinuclear pyridone compound in the ink composition is generally 0.1 to 20%, preferably 1 to 15%, particularly preferably 2 to 10%.
  • the magenta ink composition of the present invention may contain 0 to 30% of a water-soluble organic solvent and 0 to 5% by weight of an ink preparation agent, respectively.
  • the rest is water.
  • the water-soluble organic solvent used in the present invention includes: methanol, ethanol, n-propanol, isopropanol, n-butanol, Isobutanol, sec-butanol, tert-butanol, etc.
  • N N-dimethylformamide or amide of carboxylic acid such as N,N-dimethylacetamide
  • 2-pyrrolidone N- a lactam such as methyl-2-pyrrolidone
  • a cyclic nitrogen-containing solvent such as 1,3-dimethylmorpholin-2-one or 1,3-dimethylhexahydropyrimidin-2-one
  • acetone A Ketone or keto alcohol
  • cyclic ether such as tetrahydrofuran or dioxan
  • ethylene glycol 1,2- or 1,3-propanediol, 1 , 2- or 1,4-butanediol, 1,6-hexanediol.
  • Monomers, oligomers or polyfluorenes having C 2 -6 fluorenylene units such as diethylene glycol, triethylene glycol, tetraethylene glycol, dipropylene glycol, thiodiol, polyethylene glycol, polypropylene glycol a diol or a thioglycol; a polyhydric alcohol (triol) such as glycerin or hexamethylene-1,2,6-triol; ethylene glycol monomethyl ether or ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, Diethylene glycol monobutyl ether; d_ 4 mercapto ether of a polyhydric alcohol such as diethylene glycol monoethyl ether, triethylene glycol monomethyl ether or triethylene glycol monoethyl ether; ⁇ -butyrolactone or dimethyl sulfoxide Wait.
  • a polyhydric alcohol such as glycerin or hexamethylene-1,2,6-
  • water-soluble organic solvents may be used singly or in combination.
  • the ink preparation agent include antiseptic and antifungal agents, ⁇ adjusters, chelating agents, rust preventives, water-soluble ultraviolet absorbers, water-soluble polymer compounds, dye dissolvers, surfactants, and the like. .
  • antiseptic and antifungal agent examples include, for example, organic sulfurs, organic nitrogen sulfurs, organic halogens, haloallylsulfones, iodopropynes, anthraquinone-sulfonylsulfurs, nitriles, pyridines, and 8 -hydroxyquinoline, benzothiazoles, isothiazolines, dithiols, pyridine oxides, nitropropenes, organotins, phenols, quaternary ammonium salts, triazines, thiadiazines Compounds such as anilides, amantadines, dithiocarbamates, indanones, benzyl bromide, and inorganic salts.
  • organic halogen compound examples include, for example, sodium pentachlorophenol
  • examples of the pyridine oxide compound include, for example, 2-pyridinethiol-1-oxide
  • examples of the inorganic salt compound include, for example, anhydrous acetic acid.
  • Examples of the isothiazoline compound include, for example, 1,2-benzisothiazolin-3-one, 2-n-octyl-4-isothiazolin-3-one, 5-chloro-2-methyl 4-isothiazolin-3-one, 5-chloro-2-methyl-4-isothiazolin-3-one magnesium chloride, 5-chloro-2-methyl-4-isothiazolin-3-one Calcium chloride, 2-methyl-4-isothiazolin-3-one calcium chloride, and the like.
  • Examples of other antiseptic and antifungal agents include sodium sorbate and sodium benzoate.
  • the ⁇ adjusting agent is not affected by the adverse effects of the conditioned ink, and any substance can be used as long as the ⁇ ⁇ of the ink can be controlled within the range of 8.0 to 11.0.
  • decylamines such as diethanolamine and triethanolamine
  • hydroxides of alkali metals such as lithium hydroxide, sodium hydroxide, and potassium hydroxide
  • ammonium hydroxide or aqueous ammonia or lithium carbonate, sodium carbonate, and potassium carbonate.
  • An alkali metal carbonate is preferred.
  • chelating agent examples include sodium edetate, sodium nitrotriacetate, sodium hydroxyethylethylenediaminetriacetate, sodium diethylenetriaminepentaacetate, sodium urethane diacetate, and the like.
  • Examples of the rust inhibitor include acidic sulfite, sodium thiosulfate, ammonium thioglycolate, diisopropylammonium nitrite, pentaerythritol tetranitrate, dicyclohexylammonium nitrite, and the like.
  • Examples of the water-soluble ultraviolet absorber include, for example, a sulfonated benzophenone or a sulfonated benzotriazole.
  • Examples of the water-soluble high-concentration compound include polyvinyl alcohol, a cellulose derivative, a polyamine, a polyimine, and the like.
  • Examples of the dye solubilizing agent include urea, ⁇ -caprolactam, diethyl carbonate and the like.
  • surfactant examples include anionic surfactants, amphoteric surfactants, cationic surfactants, and nonionic surfactants.
  • anionic surfactant examples include, for example, a mercaptosulfocarboxylate, an ⁇ -olefinsulfonate, a polyoxyethyleneetherether acetate, a hydrazinoylamino acid, and a salt thereof.
  • ⁇ -acylmethyltaurate citronellyl soap, castor oil sulfate, lauryl sulfate, nonylphenol phosphate, thiol phosphate, decyl propyl sulfonate, Diethyl sulfosuccinate, diethylhexyl sulfosuccinic acid, dioctyl sulfosuccinate, and the like.
  • the cationic surfactant include a 2-vinylpyridine derivative and a poly-4-vinylpyridine derivative.
  • amphoteric surfactant examples include, for example, lauryl dimethylaminoacetic acid betaine, 2-mercapto-indenyl-carboxymethyl-hydrazine-hydroxyethylimidazoline-betaine, and coconut oil fatty acid amide propyl Methylaminoacetic acid betaine, other imidazoline derivatives of polyoctyl polyaminoethylglycine, and the like.
  • nonionic surfactant include, for example, polyoxyethylene nonylphenyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene lauryl phenyl ether, polyoxyethylene octylphenyl group.
  • Ethers such as ether, polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene decyl ether; polyoxyethylene oleic acid, polyoxyethylene oleate, polyoxyethylene urethane Fatty acid ester, sorbitan laurate, sorbitan monostearate, sorbitan monooleate, sorbitan sesquioleate, polyoxyethylene monooleate, Esters such as polyoxyethylene stearate; 2,4,7,9-tetramethyl-5-decyne-4,7-diol, 3,6-dimethyl-4-octyne-3 a decynediol such as 6-diol or 3,5-dimethyl-1-hexyne-diol (for example, Surfynol 104, 82, 465, Olfme STG, etc., manufactured by Nisshin Chemical Co., Ltd.).
  • These ink modulating agents can be used singly or
  • the compound of the formula I or a salt thereof is dissolved in water or the above aqueous solvent, and if necessary, it can be produced by dissolving together with the above-mentioned ink preparation agent or the like.
  • the order of dissolution of each component is not particularly limited.
  • the dye may be dissolved in water or the above aqueous solvent in advance, and dissolved by adding an ink preparation agent. After the dye is dissolved in water, an aqueous solvent or an ink preparation agent may be added to dissolve the dye. It can also be different from this order. Further, an aqueous ink or an ink preparation agent may be added to a solution obtained by subjecting the reaction liquid containing the dye or the solution containing the dye to a desalting treatment to prepare an ink composition.
  • the water to be used is preferably ion-exchanged water or deionized water having less impurities such as distilled water.
  • a filter or the like is used for precision filtration and removal of inclusions.
  • the pore size of the filter for precision filtration is usually from 1 ⁇ m to 0.1 ⁇ m, preferably from 0.8 ⁇ m to 0.2 ⁇ m.
  • the magenta ink composition of the water-soluble dinuclear pyridone sulfonic acid compound of the present invention is suitable for use in stamping, copying, marking, taking, drawing, stamping or printing, particularly for ink jet printing.
  • the advantage is that the resulting image is Water, sunlight, ozone and friction have excellent resistance and can also be used for color matching, especially for black.
  • the coloring matter of the present invention is a dye represented by the above compound of the formula I of the present invention or a salt thereof, and can be used for coloring a plurality of substrates, such as: paper, fiber or cloth (cellulose, nylon, wool, etc.), leather, filter.
  • the substrate for a color filter or the like is not limited thereto.
  • the coloring method may be, for example, a method such as a dip dyeing method, a printing method, a screen printing method, or the like, or an ink jet printing method, and an ink jet printing method is preferred.
  • Examples of the substrate to be recorded which can be applied to the ink jet printing method of the present invention include sheets for information transmission such as paper and film, fibers, leather, and the like.
  • sheets for information transfer surface treatment is usually required, and an ink absorbing layer is provided in these substrates.
  • the ink absorbing layer is, for example, a polymer such as a cation which is impregnated or coated on the substrate, and the coating layer further contains porous silica, alumina sol or special ceramics, etc., and these white inorganic substances are polyvinyl alcohol or polyethylene.
  • a hydrophilic polymer such as pyrrolidone is applied together to the surface of the substrate.
  • Sheets provided with these ink absorbing layers are generally referred to as inkjet papers/films or glossy papers/films, such as: professional glossy paper, top gloss paper, mat gloss paper (made by Canon), photo paper. Gloss, mat paper, ultra-thin special glossy film (made by Epson), high-quality glossing paper, high-quality glossy film, glossy paper (made by HP), etc.
  • plain paper can of course be used.
  • an image is printed on a substrate coated with a porous white inorganic substance, and the discoloration caused by ozone is increased.
  • the aqueous magenta ink composition of the present invention is excellent in gas resistance, such a base is The printing of the material can have a special effect.
  • porous white inorganic substance examples include calcium carbonate, kaolin, talc, clay, diatomaceous earth, synthetic amorphous silica, aluminum silicate, magnesium silicate, and calcium silicate.
  • inkjet printing of the present invention in addition to the usual yellow, cyan ink composition, there are also a green ink composition, an orange ink composition, a blue (or purple) ink composition, and a magenta ink combination of the present invention.
  • a black ink composition or the like may be used in combination as necessary.
  • the ink compositions of the respective colors are injected into respective ink cartridges and used in a predetermined position of the ink jet printer.
  • Examples of the ink jet printer include a piezoelectric printer or a foaming printer that generates bubbles by heating.
  • the water-based magenta ink composition of the present invention is a vivid magenta color, and particularly has a high vivid color tone in ink-jet glossy paper, and the recorded image has high fastness and high safety to the human body.
  • the ink composition of the present invention does not precipitate or separate during storage. Moreover, when the ink of the present invention is used in ink jet printing, the head is not blocked. The ink of the present invention does not undergo physical property changes even if it is used by a continuous ink jet printer for a long period of time or intermittent use.
  • a 10% aqueous NaOH solution was added to maintain the pH at 2.7 to 3, and it was carried out at 25 to 30 ° C for 3 hours to obtain a reaction liquid of a condensation reaction intermediate E1-C1 2 (expressed in a free acidic form).
  • the maximum absorption wavelength in water is 520 nm.
  • the ice and aqueous sodium hydroxide solution were continuously added, the pH was maintained at 9.0 ⁇ 0.3, and the temperature was raised to 27 to 30 ° C, and the reaction was carried out at this temperature and pH for 1 hour, and then at 40 to 45 ° C for 1 hour. After the completion of the reaction, water was added to adjust the amount of the liquid to about 350 parts, and the insoluble matter was removed by filtration.
  • Compound E1-C1 2 was prepared according to the steps (1) - (3) in Example 1.
  • the ice and aqueous sodium hydroxide solution were continuously added, the pH was maintained at 9.0 ⁇ 0.3, and the temperature was raised to 27 to 30 ° C, and the reaction was carried out at this temperature and pH for 1 hour, and then at 40 to 45 ° C for 1 hour. Counter After completion, water was added to adjust the liquid amount to about 350 parts, and the insoluble matter was removed by filtration.
  • the compound E-3 can be prepared by replacing sodium 5-hydroxyisophthalate in the step (4) of the first embodiment with sodium mercaptopropanesulfonate.
  • Compound E-7 can be prepared by replacing ethylenediamine in step (5) of Example 1 with ethanedithiol.
  • Compound E-4 can be prepared by replacing ethylenediamine in step (5) of Example 1 with compound L.
  • Compound E-5 can be prepared by replacing ethylenediamine in step (5) of Example 2 with compound L.
  • Compound E-6 can be prepared by replacing sodium 5-hydroxyisophthalate in step (4) with sodium decyl propane sulfonate and ethylenediamine in step (5) with compound L.
  • Compound E-8 can be prepared by replacing ethylenediamine in step (5) of Example 2 with ethanedithiol.
  • Compound E-9 can be prepared by replacing ethylenediamine in step (5) of Example 2 with hexamethylenedithiol.
  • Compound E-10 can be prepared by replacing ethylenediamine in step (5) of Example 2 with hexamethylenediamine.
  • Example 3 Magenta ink composition containing compound
  • compositions shown in the following Table were separately prepared and filtered through a 0.45 m membrane filter to obtain an aqueous magenta ink composition of the present invention. Further, ion-exchanged water and triethanolamine were added to adjust the pH of the ink composition to 8 to 10 and the total amount to 100 parts by weight.
  • the selected dye and the comparative mononuclear dye Dyel, the commercial dye C.I. Reactive Red 180 hydrolyzed derivative (abbreviated as Reactive Red 180) and C.I. Direct Red 227 were respectively prepared into comparative ink compositions. These ink compositions were used for ink jet printing, and evaluation of printed images was performed.
  • Component content (parts by weight)
  • the binuclear pyridinone dye of the invention (100%) 6
  • the remaining amount of deionized water is up to 100 parts by weight (B) Inkjet printer:
  • a high-light photographic paper manufactured by Epson Co., Ltd.
  • an ink-receiving layer containing a porous white inorganic material was subjected to inkjet printing using an ink jet printer (Epson Model 270 printer manufactured by Epson Co., Ltd.).
  • the print sample of the image has a density stage.
  • the test piece of the glossy paper manufactured by Canon and the glossy paper made by Epson was used, and the Xenon lamp weather resistance meter Ci400 (trade name; manufactured by ATLAS) was used under the conditions of humidity 60% RH and temperature 24 °C. Irradiation was carried out for 50 hours at an illuminance of O.36 W/m 2 , and the color difference ( ⁇ ) before and after the test was measured.
  • Color difference ( ⁇ ) is the value of each L*, a*, b* before and after the measurement test by the above-mentioned color measurement system (Schlab: GRETAG), and before and after the test of each value of L*, a*, b*
  • the difference is obtained by the following formula:
  • ⁇ E ((L* difference) 2 + (a difference of a*) 2 + (difference of b*) 2 ) 1/2 .
  • the glossy paper manufactured by Canon Inc. was placed in an ozone concentration of 40 ppm, a humidity of 60% RH, and a temperature of 24 ° C for 6 hours using an ozone weather resistance meter (manufactured by the company).
  • the color difference ( ⁇ ) before and after the test obtained in the same manner as in the above (2) was evaluated in three levels according to the following criteria:
  • test piece of the glossy paper manufactured by Canon and the glossy paper made by Epson was placed in a constant temperature and humidity apparatus (manufactured by Applied Technology Co., Ltd.) at 50 ° C, 90% RH for 168 hours to visually observe.
  • the exudation property before and after the test was judged and evaluated in three levels according to the following criteria.
  • the dinuclear pyridone sulfonic acid dye of the present invention has extremely excellent stability, light resistance, ozone resistance and moisture resistance as an inkjet dye.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Ink Jet (AREA)
  • Ink Jet Recording Methods And Recording Media Thereof (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

L'invention porte sur un composé d'acide anthracènepyridinesulfonique binucléaire représenté par la formule générale (I) ou un sel de celui-ci. Des compositions d'encre magenta préparées à partir du composé et du sel de celui-ci ont un aspect vif, ou un ton brillant sur du papier pour l'impression par jet d'encre, une excellente solubilité dans l'eau et une bonne filtrabilité pour la membrane filtrante pendant la production de compositions d'encre. En outre, la composition d'encre utilisant le composé de la présente invention n'a pas de cristaux précipités, de changements physiques ou de changement de couleur après une longue période de stockage et a une bonne stabilité lorsqu'elle est stockée. Les tirages utilisant la composition d'encre magenta de la présente invention n'ont pas d'exigences spéciales en ce qui concerne les matériaux pour l'impression, peuvent fidèlement reproduire et présenter le ton d'une image colorée de ton photographique et ont une bonne solidité, telle qu'une résistance à la lumière, à l'ozone et l'humidité, et l'image peut rester stable pendant longtemps.
PCT/CN2011/082623 2011-11-22 2011-11-22 Composé d'acide anthracènepyridinesulfonique binucléaire ou sel de celui-ci et son procédé de préparation et son utilisation WO2013075286A1 (fr)

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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1323303A (zh) * 1998-10-22 2001-11-21 日本化药株式会社 新型蒽吡啶酮化合物、水基深红色墨水组合物以及喷墨打印方法
CN101103077A (zh) * 2005-01-17 2008-01-09 日本化药株式会社 蒽吡啶酮化合物、洋红墨水组合物及着色体
CN101298526A (zh) * 2007-05-01 2008-11-05 佳能株式会社 喷墨墨、喷墨记录方法、墨盒、记录单元和喷墨记录设备
US20090047430A1 (en) * 2007-08-10 2009-02-19 Canon Kabushiki Kaisha Ink, ink jet recording method, ink cartridge, recording unit and ink jet recording apparatus
CN101547976A (zh) * 2006-12-01 2009-09-30 日本化药株式会社 蒽吡啶酮化合物、其盐、含有该化合物的洋红油墨组合物及着色体
US20090274840A1 (en) * 2008-04-30 2009-11-05 Canon Kabushiki Kaisha Ink jet ink, ink set, ink jet recording method, ink cartridge, recording unit and ink jet recording apparatus
CN102199379A (zh) * 2010-03-23 2011-09-28 精工爱普生株式会社 油墨组合物
CN102516231A (zh) * 2011-11-22 2012-06-27 大连理工大学 双核蒽吡啶酮磺酸化合物或其盐、其制备方法及应用

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1323303A (zh) * 1998-10-22 2001-11-21 日本化药株式会社 新型蒽吡啶酮化合物、水基深红色墨水组合物以及喷墨打印方法
CN101103077A (zh) * 2005-01-17 2008-01-09 日本化药株式会社 蒽吡啶酮化合物、洋红墨水组合物及着色体
CN101547976A (zh) * 2006-12-01 2009-09-30 日本化药株式会社 蒽吡啶酮化合物、其盐、含有该化合物的洋红油墨组合物及着色体
CN101298526A (zh) * 2007-05-01 2008-11-05 佳能株式会社 喷墨墨、喷墨记录方法、墨盒、记录单元和喷墨记录设备
US20090047430A1 (en) * 2007-08-10 2009-02-19 Canon Kabushiki Kaisha Ink, ink jet recording method, ink cartridge, recording unit and ink jet recording apparatus
US20090274840A1 (en) * 2008-04-30 2009-11-05 Canon Kabushiki Kaisha Ink jet ink, ink set, ink jet recording method, ink cartridge, recording unit and ink jet recording apparatus
CN102199379A (zh) * 2010-03-23 2011-09-28 精工爱普生株式会社 油墨组合物
CN102516231A (zh) * 2011-11-22 2012-06-27 大连理工大学 双核蒽吡啶酮磺酸化合物或其盐、其制备方法及应用

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