Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
  • C07B61/00—Other general methods
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C43/00—Ethers; Compounds having groups, groups or groups
  • C07C43/02—Ethers
  • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
  • C07C43/14—Unsaturated ethers
  • C07C43/15—Unsaturated ethers containing only non-aromatic carbon-to-carbon double bonds
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C43/00—Ethers; Compounds having groups, groups or groups
  • C07C43/02—Ethers
  • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
  • C07C43/14—Unsaturated ethers
  • C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
• • 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
  • C09B29/00—Monoazo dyes prepared by diazotising and coupling
  • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
  • C09B29/08—Amino benzenes
• • 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
  • C09B29/00—Monoazo dyes prepared by diazotising and coupling
  • C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
  • C09B29/103—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group of the naphthalene series
• • 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
• • 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
  • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
  • C09B67/0083—Solutions of dyes
• • 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
  • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
  • C09B67/0084—Dispersions of dyes
• • 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
  • C09B7/00—Indigoid dyes
  • C09B7/02—Bis-indole indigos
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D11/00—Inks
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D17/00—Pigment pastes, e.g. for mixing in paints

Definitions

• the present invention relates to a dye-containing composition containing a compound having a specific unsaturated double bond, and an ink using the same.
• Pigments that absorb or emit light can decompose and change their structure by reacting with oxygen in the air due to heat or light, causing discoloration. It has been known.
• Patent Document 1 proposes a method using a dye having a chemical structure that is difficult to react with oxygen.
• Patent Document 2 proposes a method of preventing structural changes in dyes by adding an antioxidant to a dye-containing composition.
• an object of the present invention is to provide a dye-containing composition that can suppress the fading of the dye by suppressing the decomposition of the dye, and an ink using the same.
• the present inventors found that by coexisting a dye with a compound having a specific structure containing an unsaturated double bond, it was possible to suppress the decomposition of the dye. They discovered that as a result, the fading of the dye was suppressed, and completed the present invention.
• R 1 and R 2 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a carbon Represents either an aryl group having 6 to 20 carbon atoms or an aralkyl group having 7 to 20 carbon atoms.
• R 3 and R 4 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an aralkyl group having 1 to 6 carbon atoms.
• R 5 represents any one of an alkoxy group having 6 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkenyloxy group having 2 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, and an aralkyl group having 7 to 20 carbon atoms.
• the present invention it is possible to provide a dye-containing composition that can suppress the fading of the dye by suppressing the decomposition of the dye, and an ink using the same.
• the dye-containing composition of the present invention includes a dye that absorbs or emits light having a wavelength of 380 nm to 2,500 nm, and a compound (A) having a structure represented by the following general formula (I). It is a thing.
• R 1 and R 2 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a carbon Represents either an aryl group having 6 to 20 carbon atoms or an aralkyl group having 7 to 20 carbon atoms.
• R 3 and R 4 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an aralkyl group having 1 to 6 carbon atoms.
• the dye-containing composition of the present invention since the specific compound having an unsaturated double bond and the dye coexist, it becomes possible to suppress fading of the dye.
• the reason for this is thought to be as follows. That is, when a compound having the structure represented by the general formula (I) is blended into a dye-containing composition, the moiety derived from the allyl ether skeleton reacts with oxygen through a radical-mediated reaction. It is thought that this reduces the amount of oxygen in the dye-containing composition and makes it difficult for the dye to decompose due to oxygen, thereby making it possible to suppress the fading of the dye.
• the present invention will be explained in detail below.
• the dye-containing composition of the present invention contains a dye that absorbs or emits light having a wavelength of 380 nm to 2,500 nm.
• the dye used in the present invention is not particularly limited as long as it absorbs or emits light with a wavelength of 380 nm to 2,500 nm, and includes dyes and pigments commonly used in inks, etc. Among these, it is preferable to use a dye that absorbs light with a wavelength of 380 nm to 1,500 nm.
• the maximum peak of absorption or emission wavelength of the dye is preferably in the range of 380 nm to 2,500 nm, more preferably in the range of 380 nm to 1,500 nm, and particularly the maximum peak of absorption wavelength is in the range of 380 nm to 1,500 nm. It is more preferable that it exists in the range of 380 nm to 1,000 nm, and even more preferably that it exists in the range of 380 nm to 900 nm. If the maximum wavelength peak is within the above range, when used as an ink, favorable color development can be achieved and fading can be suppressed.
• the absorption wavelength of the dye refers to a value measured by ultraviolet-visible-near-infrared spectroscopy
• the emission wavelength refers to a value measured by fluorescence photometry.
• the dye examples include at least one selected from pH-sensitive dyes such as methyl yellow, o-cresol red, thymol blue, 2,4-dinitrophenol, methyl orange, methyl red, and neutral red.
• pH-sensitive dyes such as methyl yellow, o-cresol red, thymol blue, 2,4-dinitrophenol, methyl orange, methyl red, and neutral red.
• inorganic pigments and organic pigments can be used as pigments, and inorganic pigments include iron oxide, barium yellow, cadmium red, and chrome yellow, as well as known methods such as contact method, furnace method, and thermal method. Carbon black etc. manufactured by the method described above can be used.
• organic pigments examples include azo pigments (including azo lakes, insoluble azo pigments, condensed azo pigments, chelate azo pigments, etc.), polycyclic pigments (for example, phthalocyanine pigments, perylene pigments, perinone pigments, anthraquinone pigments, quinacridone pigments, dioxazine) Pigments, indigo pigments, thioindigo pigments, isoindolinone pigments, quinofularone pigments, etc.), dye chelates (for example, basic dye type chelates, acid dye type chelates, etc.), nitro pigments, nitroso pigments, aniline black, etc. can be used. .
• azo pigments including azo lakes, insoluble azo pigments, condensed azo pigments, chelate azo pigments, etc.
• polycyclic pigments for example, phthalocyanine pigments, perylene pigments, perinone pigments, anthraquinone pigment
• C. I. Pigment Yellow 1, 3, 12, 13, 14, 17, 24, 34, 35, 37, 42 (yellow iron oxide), 53, 55, 74, 81, 83, 95, 97, 98, 100, 101, 104 , 408, 109, 110, 117, 120, 128, 138, 150, 151, 153, 183, C.
• Pigment Orange 5 13, 16, 17, 36, 43, 51, C. I.
• Other pigments include those described in The Color Index, Third Edition (The SoC.I.ety of Dyers and Colourists, 1982).
• an infrared absorbing compound may be used as the dye.
• infrared absorbing compounds commonly used for heat shielding films and infrared cut filters can be used, and examples thereof include diimonium compounds and aminium compounds.
• commercial products of diimonium compounds include KAYASORB IRG-069, IRG-068, IRG-022 manufactured by Nippon Kayaku Co., Ltd., NIR-IM1 manufactured by Nagase ChemteX Co., Ltd., and commercial products of aminium compounds. Examples include NIR-AM1 manufactured by Nagase ChemteX Co., Ltd.
• a material that emits light in the process of returning from the excited state to the ground state after being excited by external energy can also be used as the dye.
• materials used for organic EL (OLED), fluorescent agents, etc. can be used.
• the dye used in the present invention is not particularly limited and any of the above-mentioned dyes can suppress discoloration, but organic pigments are preferred from the viewpoint of more effectively suppressing discoloration.
• the content of the dye in the dye-containing composition is preferably 0.001 to 10.0% by mass, more preferably 0.01 to 5.0% by mass, and 0.1 to 5.0% by mass. It is more preferably 3.0% by mass, even more preferably 0.1 to 2.0% by mass, and particularly preferably 0.1 to 1.0% by mass.
• the content of the dye is at least the lower limit, the dye-containing composition is sufficiently colored and can be suitably used for inks and the like.
• it is preferable that the content of the dye in the dye-containing composition is less than or equal to the above-mentioned upper limit, since the amount of the dye will be appropriate and the manufacturing cost will be reduced.
• the dye-containing composition of the present invention comprises a compound (A) containing a structure represented by the following general formula (I) [hereinafter sometimes simply referred to as "compound (A)"]. ] Contains. Since the compound (A) can capture oxygen in the dye-containing composition as described above, it becomes possible to suppress the decomposition of the dye caused by oxygen.
• R 1 and R 2 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or an alkenyl group having 2 to 6 carbon atoms.
• Examples of the alkyl group having 1 to 6 carbon atoms represented by R 1 and R 2 include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group. group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, and cyclohexyl group.
• Examples of the alkoxy group having 1 to 6 carbon atoms represented by R 1 and R 2 include methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, sec-butoxy group, and tert -butoxy group, etc.
• alkenyl group having 2 to 6 carbon atoms represented by R 1 and R 2 examples include vinyl group, allyl group, propenyl group, isopropenyl group, butenyl group, isobutenyl group, pentenyl group, prenyl group, hexenyl group (cis- (3-hexenyl group, etc.), and cyclohexenyl group.
• Examples of the aryl group having 6 to 20 carbon atoms represented by R 1 and R 2 include phenyl group, tolyl group, xylyl group, and naphthyl group.
• Examples of the aralkyl group having 7 to 20 carbon atoms represented by R 1 and R 2 include benzyl group, 2-phenylethyl group, 2-naphthylethyl group, and diphenylmethyl group.
• R 1 and R 2 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an alkenyl group having 2 to 6 carbon atoms. It is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, even more preferably an alkyl group having 1 to 4 carbon atoms, and even more preferably a methyl group.
• R 3 and R 4 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or an alkenyl group having 2 to 6 carbon atoms.
• Examples of the alkenyloxy group having 2 to 6 carbon atoms represented by R 3 and R 4 include vinyloxy group, 2-propenyloxy group, 2-butenyloxy group, 3-butenyloxy group, and 4-pentenyloxy group.
• R 3 and R 4 are each independently a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, an alkenyl group having 2 or 3 carbon atoms, or an aryl group having 6 to 20 carbon atoms. is preferable, a hydrogen atom or a methyl group is more preferable, and a hydrogen atom is even more preferable.
• R 3 and R 4 are both hydrogen atoms.
• the compound (A) containing the structure represented by the general formula (I) is a compound containing the structure represented by the following general formula (II) from the viewpoint of making it easier to capture oxygen in the dye-containing composition. , or a compound represented by the following general formula (III).
• R 1 and R 2 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, and a carbon number 2 to R 3 and R 4 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, and an aralkyl group having 7 to 20 carbon atoms.
• an alkoxy group having 1 to 6 carbon atoms an alkenyl group having 2 to 6 carbon atoms, an alkenyloxy group having 2 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, and an aralkyl group having 7 to 20 carbon atoms. represents something.
• R 5 is a hydrogen atom, a (meth)acrylic group, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkenyloxyalkyl group having 2 to 8 carbon atoms, a carbon number Represents either an aryl group having 6 to 20 carbon atoms or an aralkyl group having 7 to 20 carbon atoms.
• R 6 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms.
• R 7 represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a (meth)acryloyl group, a 4-vinylphenyl group, or an alkenyl group having 2 to 6 carbon atoms.
• n is any integer.
• R 1 , R 2 , R 3 and R 4 in general formula (II) and general formula (III) are the same as R 1 , R 2 , R 3 and R 4 in general formula (I) above, respectively. , and redundant explanation will be omitted here.
• R 5 is a hydrogen atom, a (meth)acrylic group, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkenyloxyalkyl group having 2 to 8 carbon atoms, a carbon number Represents either an aryl group having 6 to 20 carbon atoms or an aralkyl group having 7 to 20 carbon atoms.
• alkyl group having 1 to 6 carbon atoms examples of the alkyl group having 1 to 6 carbon atoms, alkenyl group having 2 to 6 carbon atoms, aryl group having 6 to 20 carbon atoms, and aralkyl group having 7 to 20 carbon atoms in R 5 are the same as above, Duplicate explanations will be omitted here.
• the alkenyloxyalkyl group having 2 to 8 carbon atoms represented by R 5 includes vinyloxymethyl group, 2-propenyloxyethyl group, 2-butenyloxyethyl group, 3-butenyloxyethyl group. group, 4-pentenyloxyethyl group, isopentenyloxyethyl group, and the like.
• R 5 in the general formula (II) is preferably a hydrogen atom or an alkenyloxyalkyl group having 2 to 8 carbon atoms, from the viewpoint of improving the oxygen absorption performance of the compound (A); An ethyl group is more preferred, and a hydrogen atom is even more preferred.
• R 6 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms.
• R 7 represents any one of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a (meth)acryloyl group, a 4-vinylphenyl group, and an alkenyl group having 2 to 6 carbon atoms.
• R 6 in the general formula (III) is preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, more preferably a methyl group, from the viewpoint of improving the oxygen absorption performance of the compound (A).
• R 7 in III) is preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, more preferably a hydrogen atom.
• the number average molecular weight (Mn) of the compound represented by general formula (III) in terms of polystyrene is preferably 200 to 50,000, more preferably 500 to 20,000, 1,000 to 10, 000 is more preferable, and even more preferably 2,000 to 9,000.
• the number average molecular weight in this specification is the standard polystyrene equivalent molecular weight determined by gel permeation chromatography (GPC) measurement.
• compound (A) examples include allyl ether compounds such as allyl methyl ether, diallyl ether, allyl glycidyl ether, glycerin diallyl ether, and pentaerythritol triallyl ether, prenyl methyl ether, prenyl ethyl ether, prenyl glycidyl ether, Prenyl ether compounds such as glycerin diprenyl ether, diethylene glycol diprenyl ether, nonanediol diprenyl ether, polyoxyethylene allyl ether, polyoxyethylene prenyl ether, polyoxypropylene prenyl ether, ⁇ -methoxy- ⁇ -hydroxy poly[oxy( Examples include polyether compounds such as 3-methyl-2-butenoxymethylethane-1,2-diyl).
• the dye-containing composition of the present invention preferably contains 0.1 to 30.0 parts by mass of the compound (A) containing the structure represented by the general formula (I) based on 100 parts by mass of the dye.
• the content of the compound (A) is equal to or higher than the lower limit, oxygen in the dye-containing composition can be sufficiently captured, so that decomposition of the dye due to oxygen can be suppressed, and as a result, the dye can suppress discoloration.
• the content of the compound (A) is less than or equal to the upper limit, the balance between manufacturing cost and the effect obtained will be better.
• the content of the compound (A) is preferably 1.0 to 25.0 parts by mass, more preferably 3.0 to 20.0 parts by mass, and 5.0 to 15 parts by mass.
• the amount is more preferably .0 parts by weight, and even more preferably from 7.0 to 12.0 parts by weight.
• the content of the compound (A) containing the structure represented by the general formula (I) in the dye-containing composition of the present invention is preferably 0.001 to 3% by mass, and preferably 0.005 to 3% by mass. It is more preferably 2% by mass, and even more preferably from 0.01 to 1% by mass.
• the content of the compound (A) is equal to or higher than the lower limit, oxygen in the dye-containing composition can be sufficiently captured, so that decomposition of the dye due to oxygen can be suppressed, and as a result, the dye can suppress discoloration.
• the content of the compound (A) is less than or equal to the upper limit, the balance between manufacturing cost and the effect obtained will be better.
• the dye-containing composition of the present invention preferably contains a solvent from the viewpoint of uniformly dissolving or dispersing the dye and the compound (A).
• the solvent used in the present invention is not particularly limited, but examples include aromatic hydrocarbons such as toluene, xylene, mesitylene, cumene, and p-cymene; Cyclic ethers such as tetrahydrofuran and 1,4-dioxane; Alcohols such as methanol, ethanol, isopropanol, butanol, ethylene glycol, propylene glycol; Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone; Esters such as methyl acetate, ethyl acetate, butyl acetate, methyl lactate, ethyl lactate, ⁇ -butyrolactone; Ethyl hydrocarbon
• the content thereof is preferably 70.0 to 99.9% by mass, more preferably 80.0 to 99.8% by mass, More preferably, it is 90.0 to 99.7% by mass.
• the dye-containing composition of the present invention includes fillers, thickeners, low shrinkage agents, anti-aging agents, plasticizers, aggregates, flame retardants, stabilizers, antioxidants, etc., the dyes, compound (A) and It may further contain components other than the solvent.
• the content thereof is preferably 20% by mass or less, more preferably 10% by mass or less, and even more preferably 5% by mass or less. preferable.
• the method for producing the dye-containing composition is not particularly limited, and it can be easily produced, for example, by a method including a mixing step of mixing the dye and the compound (A).
• a method including a mixing step of mixing the dye and the compound (A) There is no particular restriction on the method of mixing the dye, compound (A), solvent, and other components, and the mixture can be obtained by mixing using a known method.
• the ink of the present invention contains the dye-containing composition of the present invention. Therefore, the ink of the present invention has the property that the pigment does not easily fade even after being stored for a certain period of time.
• the amount of remaining pigment was measured according to the following procedure.
• the composition was heated at 80°C for 72 hours.
• the dye-containing compositions before and after heating were each dissolved in N,N-dimethylformamide (DMF) and subjected to ultraviolet-visible-near-infrared spectroscopy.
• DMF N,N-dimethylformamide
• the dye When the decomposition of the dye progresses due to heating, a decrease in absorbance at a specific wavelength and an increase in absorbance at different wavelengths are observed. Among these, the dye was quantified based on the degree of decrease in the absorption peak at a specific wavelength before and after heating each dye-containing composition. In this evaluation, a larger amount of residual dye indicates less fading (less decomposition of the dye).
• the mixture was stirred at an internal temperature of 50°C for 6 hours, and then cooled to 25°C.
• the reaction solution was neutralized with a 4M aqueous hydrochloric acid solution, and the upper layer was washed with 310 mL of ion-exchanged water.
• the obtained organic layer was purified by distillation to obtain 28.77 g (0.126 mol) of 1,3-bis(3-methyl-2-butenoxy)-2-hydroxypropane represented by the following formula (A-1). 60.3%).
• ⁇ Comparative compound> ⁇ Antioxidant: Irganox 1010 (manufactured by BASF Japan Co., Ltd.) ⁇ Antioxidant: Tristearyl phosphite (manufactured by Fujifilm Wako Chemical Co., Ltd.) ⁇ Radical scavenger: ADEKA STAB LA-52 (manufactured by ADEKA Co., Ltd.)
• Example 1 Comparative Examples 1 to 4> A slurry of the dye-containing composition was prepared according to the formulation shown in Table 1 and heated at 80° C. for 176 hours. The dye-containing composition before and after heating was dissolved in N,N-dimethylformamide (DMF), and the remaining amount of the dye was measured from the change in absorbance at 390 nm by ultraviolet-visible-near-infrared spectroscopy. The results are shown in Table 1.
• DMF N,N-dimethylformamide
• the dye-containing composition containing the compound (A) containing the structure represented by general formula (I) can suppress the decomposition of the dye and prevent discoloration.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (AREA)
• Materials Engineering (AREA)
• Wood Science & Technology (AREA)
• Dispersion Chemistry (AREA)
• Inks, Pencil-Leads, Or Crayons (AREA)

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Citations (7)

• 2023
  • 2023-03-10 JP JP2024506426A patent/JPWO2023171797A1/ja active Pending
  • 2023-03-10 WO PCT/JP2023/009320 patent/WO2023171797A1/ja not_active Ceased
  • 2023-03-10 TW TW112108983A patent/TW202402966A/zh unknown

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