WO2019065043A1 - Procédé de production de composé, composition et composition durcissable - Google Patents

Procédé de production de composé, composition et composition durcissable Download PDF

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WO2019065043A1
WO2019065043A1 PCT/JP2018/031640 JP2018031640W WO2019065043A1 WO 2019065043 A1 WO2019065043 A1 WO 2019065043A1 JP 2018031640 W JP2018031640 W JP 2018031640W WO 2019065043 A1 WO2019065043 A1 WO 2019065043A1
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group
formula
compound
compound represented
ring
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PCT/JP2018/031640
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Japanese (ja)
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竹内　潔
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富士フイルム株式会社
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Priority to CN201880062034.XA priority Critical patent/CN111132978B/zh
Priority to JP2019544441A priority patent/JP6967598B2/ja
Publication of WO2019065043A1 publication Critical patent/WO2019065043A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
    • C07D339/02—Five-membered rings
    • C07D339/06—Five-membered rings having the hetero atoms in positions 1 and 3, e.g. cyclic dithiocarbonates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/06—Peri-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere

Definitions

  • the present invention relates to a process for the preparation of compounds. More specifically, the present invention relates to a method for producing a benzodithiol compound. The present invention also relates to a composition comprising a benzodithiol compound and a curable composition comprising the above-mentioned composition.
  • Patent Document 1 describes an invention relating to a UV absorber containing a specific benzodithiol compound. Further, Patent Document 1 describes that a benzodithiol compound having a nitrogen leaving group is reacted with a pyrazolidine dione compound to produce a benzodithiol compound.
  • an object of the present invention is to provide a method, a composition and a curable composition for producing a compound capable of producing a less colored benzodithiol compound.
  • the present invention provides the following.
  • each of R 11 and R 12 independently represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group or an aryloxy group;
  • R 21 and R 22 each independently represent an alkyl group;
  • a 1 and A 2 are OH or O independently -; and at least one of A 1 and A 2 represent OH;
  • X and Y each independently represent an electron withdrawing group;
  • Z represents an n-valent anion, n 1 or more represents an integer; however, one of A 1 and A 2 are O - may represent, Z is absent;
  • R 11 and R 12 may be bonded to each other to form a ring,
  • R 21 and R 22 may be bonded to each other to form a ring, and
  • X and Y are bonded to each other to form a ring It may be ⁇ 2
  • each of R 11 and R 12 independently represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group or an aryloxy group;
  • R 13 and R 14 each independently represent an aliphatic group, an aromatic group or a heterocyclic group;
  • R 11 and R 12 may be bonded to each other to form a ring, and
  • R 13 and R 14 may be bonded to each other to form a ring.
  • a composition containing a compound represented by the formula (1) has a ratio of a molar absorption coefficient ⁇ 385 at a wavelength of 385 nm to a molar absorption coefficient ⁇ 430 at a wavelength of 430 nm in the spectral absorption spectrum measured in methanol, ⁇ 430 / ⁇ 385 is 0.015 to 0
  • the composition being .028;
  • each of R 11 and R 12 independently represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group or an aryloxy group;
  • X and Y each independently represent an electron withdrawing group;
  • R 11 and R 12 may be bonded to each other to form a ring;
  • X and Y may be bonded to each other to form a ring.
  • composition as described in ⁇ 9> which is a ⁇ 10> ultraviolet absorber.
  • the curable composition containing the composition as described in ⁇ 11> ⁇ 9> or ⁇ 10>, and a curable compound.
  • the curable composition as described in ⁇ 11> whose ⁇ 12> curable compound is a compound which has -O-Si-O- structure.
  • the manufacturing method of the compound which can manufacture a little benzodithiol compound of coloring can be provided.
  • a composition containing a less colored benzodithiol compound, and a curable composition can be provided.
  • the notation not describing substitution and non-substitution includes a group having a substituent together with a group having no substituent.
  • the "alkyl group” includes not only an alkyl group having no substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
  • a numerical range represented using “to” means a range including the numerical values described before and after “to” as the lower limit value and the upper limit value.
  • total solids refers to the total amount of all components of the composition excluding the solvent.
  • (meth) acrylate represents both or either of acrylate and methacrylate
  • (meth) acryl represents both or either of acrylic and methacryl
  • Allyl represents both or any of allyl and methallyl
  • (meth) acryloyl represents both or any of acryloyl and methacryloyl.
  • step does not only mean an independent step, but if the intended function of that step is achieved even if it can not be clearly distinguished from other steps, this term include.
  • the weight average molecular weight (Mw) and the number average molecular weight (Mn) are defined as polystyrene conversion values measured by gel permeation chromatography (GPC).
  • the method for producing the compound of the present invention comprises reacting the compound represented by the formula (2) with the compound represented by the formula (3) in the presence of a reducing agent. It is a manufacturing method.
  • each of R 11 and R 12 independently represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group or an aryloxy group
  • R 21 and R 22 each independently represent an alkyl group
  • a 1 and A 2 are OH or O independently -
  • at least one of A 1 and A 2 represent OH
  • X and Y each independently represent an electron withdrawing group
  • Z represents an n-valent anion, n 1 or more represents an integer; however, one of A 1 and A 2 are O - may represent, Z is absent;
  • R 11 and R 12 may be bonded to each other to form a ring, R 21 and R 22 may be bonded to each other to form a ring, and X and Y are bonded
  • the compound represented by the formula (2) in the production of the compound represented by the formula (1), the compound represented by the formula (2) is reacted with the compound represented by the formula (3) in the presence of a reducing agent. It is possible to obtain a less colored product containing the compound represented by (1).
  • a side reaction product And so on in addition to the compound represented by Formula (1), a side reaction product And so on, and it was found that the presence of these side reactions causes the coloration.
  • the compound represented by the formula (2) is reacted with the compound represented by the formula (3) in the presence of a reducing agent.
  • the formula (3) as a raw material is obtained by the action of the reducing agent. It is considered that the compound represented by the formula (I) or the compound represented by the formula (1) which is a product is decomposed to increase the amount of impurities or the reaction efficiency is reduced to make the color more likely to occur. However, it is surprising that even a person skilled in the art could not predict that the color-suppressed product could be obtained by carrying out the above reaction in the presence of a reducing agent.
  • the reaction for obtaining the compound represented by the formula (1) is carried out in the presence or absence of a solvent in a system in which the compound represented by the formula (2) and the compound represented by the formula (3) coexist. Furthermore, acids, bases, salts, other organic compounds, inorganic compounds and the like may be added.
  • the reducing agent may be an organic reducing agent or an inorganic reducing agent.
  • an organic reducing agent ascorbic acid, ascorbic acid derivatives (eg, 3-O-ethyl ascorbic acid, ascorbic acid-2-glucoside), sulfinic acids (eg, methanesulfinic acid, benzenesulfinic acid), formic acid, oxalic acid, substituted Or unsubstituted 4-aminophenol, substituted or unsubstituted p-phenylenediamine, substituted or unsubstituted 1-phenyl-3-pyrazolidone, and the like.
  • the inorganic reducing agent foam water hydrazine, reduced iron, tin, sulfur dioxide, sodium sulfite, sodium borohydride, lithium aluminum hydride and the like can be mentioned.
  • the standard redox potential of the reducing agent is preferably -0.5 to 1.0V.
  • the lower limit is preferably ⁇ 0.2 V or more, more preferably 0 V or more.
  • the upper limit is preferably 0.7 V or less, more preferably 0.5 V or less.
  • the reducing agent is preferably an organic reducing agent, more preferably ascorbic acid or an ascorbic acid derivative, and still more preferably ascorbic acid (standard redox potential 0.34 V).
  • reaction solvent water, an amide solvent (for example, N, N-dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone), a sulfone solvent (for example, Sulfolane), sulfoxide solvents (eg, dimethyl sulfoxide), ureide solvents (eg, tetramethylurea), alcohol solvents (eg, methanol, ethanol, 2-propanol, 2-propanol, octanol, benzyl alcohol) Ether solvents (eg, dioxane, anisole, tetrahydrofuran), ketone solvents (eg, acetone, cyclohexanone), hydrocarbon solvents (eg, toluene, xylene, mesitylene, n-octane, n-dodecane), Halogenated solvents (eg chlorobensene,
  • amide solvents sulfone solvents, sulfoxide solvents, ureide solvents, alcohol solvents, ether solvents, hydrocarbon solvents, halogen solvents and nitrile solvents are preferable, and amide solvents are preferable. More preferable.
  • the amide solvent is particularly good in the solubility of the compound of the formula (2) as the starting material, and the reaction of the compound of the formula (2) with the compound of the formula (3) is possible by using the amide solvent as a reaction solvent.
  • the generation of impurities can be suppressed by enhancing the properties and suppressing the progress of side reactions and the like.
  • the reaction temperature of the compound represented by the formula (2) with the compound represented by the formula (3) is preferably 0 to 250 ° C.
  • the lower limit is preferably 10 ° C. or more, more preferably 20 ° C. or more, further preferably 25 ° C. or more, and particularly preferably 30 ° C. or more. 200 degrees C or less is preferable, 120 degrees C or less is more preferable, and 90 degrees C or less is still more preferable. If the reaction temperature is in the above range, the progress of side reactions can be suppressed to suppress the generation of impurities.
  • the reaction time is preferably 1 minute to 24 hours.
  • the lower limit is preferably 5 minutes or more, more preferably 10 minutes or more, and still more preferably 15 minutes or more.
  • the upper limit is preferably 12 hours or less, more preferably 8 hours or less, and still more preferably 4 hours or less.
  • the reaction of the compound represented by the formula (2) with the compound represented by the formula (3) is carried out by comparing the number of moles of the compound represented by the formula (3) to the number of moles of the compound represented by the formula (2)
  • the reaction is preferably performed at a ratio of 0.01 or more, more preferably 0.1 or more, and still more preferably 0.3 or more. It is particularly preferable to react at a ratio of
  • the upper limit of the aforementioned ratio is preferably 10.0 or less, more preferably 6.0 or less, still more preferably 4.0 or less, and particularly preferably 2.0 or less.
  • the ratio of the number of moles of the reducing agent to the number of moles of the compound represented by the formula (2) is preferably 0.0001 or more, and more preferably 0.001 or more Is more preferably 0.01 or more, and particularly preferably 0.02 or more.
  • the upper limit of the aforementioned ratio is preferably 20.0 or less, more preferably 10.0 or less, still more preferably 5.0 or less, and particularly preferably 2.0 or less.
  • a compound represented by the formula (2) and a compound represented by the formula (3) are reacted in the presence of a reducing agent and then represented by the formula (1) which is a reactant obtained. It is particularly preferred to add further acid to the compound. Side reactions such as oxidation reaction of the compound represented by the formula (1) or the compound represented by the formula (2) or substitution reaction with a phenol moiety tend to proceed if the reaction system is basic, but the reaction By adding an acid to a substance, the progress of these side reactions can be effectively suppressed to further suppress the generation of impurities and the like. As a result, it is possible to obtain a product containing the compound represented by the formula (1) which is the target compound in high purity.
  • an organic acid may be sufficient and an inorganic acid may be sufficient.
  • the organic acid include sulfonic acid (eg, methanesulfonic acid, p-toluenesulfonic acid), carboxylic acid (eg, acetic acid, formic acid, butyric acid, benzoic acid, oxalic acid) and the like
  • inorganic acids include hydrochloric acid, sulfuric acid, Nitric acid, phosphoric acid and the like can be mentioned.
  • it is an organic acid, most preferably it is a sulfonic acid.
  • the amount of the acid added is preferably such that the ratio of moles of the acid to the number of moles of the compound represented by the formula (2) is 0.0001 or more, more preferably 0.001 or more, and 0 More preferably, it is not less than 0.11 and particularly preferably not less than 0.1.
  • the upper limit of the aforementioned ratio is preferably 50.0 or less, more preferably 20.0 or less, still more preferably 10.0 or less, and particularly preferably 5.0 or less.
  • the reaction mixture is added to water or another solvent, or a mixed solvent thereof, or the above-mentioned solvent is added to the reaction mixture to solidify the compound represented by formula (1) as crystals or amorphous, It is preferable to remove and isolate the solvent by a method such as filtration. It is also preferable to add a solvent to the taken out solid and wash it, or dissolve it in a solvent and then add another solvent depending on the case to recrystallize it. Furthermore, these steps may be performed multiple times. Thus, the compound represented by Formula (1) can be manufactured.
  • the product containing the compound represented by the formula (1) obtained by the production method of the present invention has a molar absorption coefficient ⁇ 385 at a wavelength of 385 nm and a molar absorption coefficient ⁇ at a wavelength of 430 nm in the spectral absorption spectrum measured in methanol. It is preferable that ⁇ 430 / ⁇ 385 , which is a ratio to 430 , be 0.015 to 0.028.
  • the molar absorption coefficient ratio is preferably 0.018 or more, more preferably 0.020 or more, still more preferably 0.021 or more, and particularly preferably 0.022 or more. preferable.
  • the molar absorption coefficient ratio is preferably 0.027 or less, more preferably 0.026 or less, and still more preferably 0.025 or less. Those having a ratio of such molar absorption coefficients have excellent absorption of light in the visible region near the ultraviolet region despite the high absorption near the wavelength of 385 nm, and therefore the absorption of ultraviolet light on the longer wavelength side While excellent, it has excellent visible transparency. When it is attempted to shift the absorption region of ultraviolet light in the compound to a longer wavelength side, the transmittance of light in the visible region (in particular, the transmittance of light in the visible region near the ultraviolet region) also tends to decrease. According to the present invention, it has the technically superior effect of being excellent in the absorptivity of ultraviolet rays on the longer wavelength side while maintaining the light transmittance of the visible region at a high level.
  • R 11 and R 12 each independently represent a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group or an aryloxy group.
  • the halogen atom includes a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • the carbon number of the alkyl group and the alkoxy group is preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 15, particularly preferably 1 to 10, and most preferably 1 to 7.
  • the alkyl group and the alkoxy group may be linear, branched or cyclic, preferably linear or branched, and more preferably linear.
  • the cyclic alkyl group and the alkyl group moiety of the cyclic alkoxy group may be a monocyclic cycloalkyl group or a polycyclic alkyl group (bicycloalkyl group, tricycloalkyl group, etc.) .
  • the alkyl group and the alkoxy group may have a substituent.
  • substituents include the groups described for the substituent T described later.
  • the carbon number of the aryl group and the aryloxy group is preferably 6 to 40, more preferably 6 to 30, still more preferably 6 to 20, particularly preferably 6 to 15, and most preferably 6 to 12.
  • the aryl group and the aryloxy group may have a substituent. Examples of the substituent include the groups described for the substituent T described later.
  • R 11 and R 12 may be bonded to each other to form a ring.
  • the ring formed by combining R 11 and R 12 is preferably a 5- or 6-membered ring.
  • the ring formed by combining R 11 and R 12 may have a substituent. Examples of the substituent include the groups described for the substituent T described later.
  • R 21 and R 22 each independently represent an alkyl group.
  • the carbon number of the alkyl group is preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 15, particularly preferably 1 to 10, and most preferably 1 to 7.
  • the alkyl group may be linear, branched or cyclic, preferably linear or branched, and more preferably linear.
  • the cyclic alkyl group may be a monocyclic cycloalkyl group or a polycyclic alkyl group (such as a bicycloalkyl group or a tricycloalkyl group).
  • the alkyl group may have a substituent. Examples of the substituent include the groups described for the substituent T described later.
  • R 21 and R 22 may be bonded to each other to form a ring.
  • the ring formed by combining R 21 and R 22 is preferably a 5- or 6-membered ring. Specifically, a pyrrolidine ring, a piperidine ring, a morpholine ring and the like can be mentioned, and a pyrrolidine ring and a piperidine ring are preferable, and a piperidine ring is more preferable.
  • the ring formed by combining R 21 and R 22 may have a substituent. Examples of the substituent include the groups described for the substituent T described later.
  • a 1 and A 2 are OH or O independently -; and at least one of A 1 and A 2 represent OH.
  • Z represents an n-valent anion, and n represents an integer of 1 or more. n is preferably 1 to 5, more preferably 1 to 3, and still more preferably 1 or 2. However, one of A 1 and A 2 are O - may represent, Z is absent. That is, one of A 1 and A 2 are O - when referring to a compound represented by the formula (2), and cations on the nitrogen atom, an intramolecular salt and the anion of the oxygen atoms of A 1 or A 2 Form. Further, when both of A 1 and A 2 represent OH, the compound represented by the formula (2) forms a salt with a cation on the nitrogen atom and Z as a counter anion.
  • the n-valent anion represented by Z may be an organic anion or an inorganic anion. Also, it may be a monovalent anion or a polyvalent anion.
  • the organic anion include substituted or unsubstituted sulfonate anion (eg, methanesulfonate anion, p-toluenesulfonate anion), substituted or unsubstituted carboxylate anion (eg, acetate anion, formate anion, propionate anion, Examples thereof include benzoate, trifluoroacetate, oxalate and phthalate anions, and substituted or unsubstituted phenoxide anions (eg, phenoxide anion, hydroquinone monoanion, hydroquinone dianion) and the like.
  • inorganic anion fluoride ion, chloride ion, bromide ion, sulfate anion, nitrate anion, phosphate anion and the like can be mentioned. It is preferably an organic anion, more preferably a carboxylate anion or a phenoxide anion, still more preferably a carboxylate anion, and most preferably an acetate anion.
  • Halogen atom eg, chlorine atom, bromine atom, iodine atom
  • Alkyl group [linear, branched or cyclic alkyl group. Specifically, a linear or branched alkyl group (preferably a linear or branched alkyl group having 1 to 30 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, t-butyl, n -Octyl group, eicosyl group, 2-chloroethyl group, 2-cyanoethyl group, 2-ethylhexyl group), cycloalkyl group (preferably, a cycloalkyl group having a carbon number of 3 to 30, for example, cyclohexyl group, cyclopentyl group, 4- 4- n-dodecylcyclohexyl group), a bicycloalkyl group (preferably a bicycloalkyl group (preferably a biflu
  • alkyl group for example, the alkyl group of the alkylthio group
  • substituents described below also represents an alkyl group having such a concept.
  • Alkenyl group [linear, branched or cyclic alkenyl group; Specifically, a linear or branched alkenyl group (preferably a linear or branched alkenyl group having a carbon number of 2 to 30, for example, a vinyl group, an allyl group, a prenyl group, a geranyl group, an oleyl group), a cycloalkenyl group (Preferably, a cycloalkenyl group having 3 to 30 carbon atoms, that is, a monovalent group obtained by removing one hydrogen atom of a cycloalkene having 3 to 30 carbon atoms.
  • bicyclo [2,2,1] hept-2-en-1-yl group, bicyclo [2,2,2] oct-2-en-4-i group Is intended to include a group).
  • alkynyl group preferably, a linear or branched alkynyl group having a carbon number of 2 to 30, for example, ethynyl group, propargyl group, trimethylsilylethynyl group;
  • An aryl group (preferably an aryl group having a carbon number of 6 to 30, for example, a phenyl group, a p-tolyl group, a naphthyl group, a m-chlorophenyl group, an o-hexadecanoylaminophenyl group);
  • a heterocyclic group (preferably a monovalent group obtained by removing one hydrogen atom from a 5- or 6-membered aromatic or non-aromatic heterocyclic compound), more preferably a 5- or 6-membered member having 3 to 30 carbon atoms
  • Aromatic heterocyclic group of, for example, 2-furyl group, 2-thienyl group, 2-pyrimidinyl group, 2-benzothiazolyl group); Cyano group; Hydroxyl group; Nitro group; Carboxyl group;
  • An alkoxy group (preferably, a linear or branched alkoxy group having a carbon number of 1 to 30.
  • Aryloxy group preferably an aryloxy group having a carbon number of 6 to 30.
  • phenoxy group 2-methylphenoxy group, 4-t-butylphenoxy group, 3-nitrophenoxy group, 2-tetradecanoylaminophenoxy group
  • a silyloxy group preferably a silyloxy group having a carbon number of 3 to 20, for example, a trimethylsilyloxy group, a t-butyldimethylsilyloxy group
  • a heterocyclic oxy group preferably, a heterocyclic oxy group having a carbon number of 2 to 30, for example, 1-phenyltetrazole-5-oxy group, 2-tetrahydropyranyloxy group
  • Acyloxy group preferably formyloxy group, alkylcarbonyloxy group having 2 to 30 carbon atoms, arylcarbonyloxy group having 6 to 30 carbon atoms.
  • formyloxy group, acetyloxy group, pivaloyloxy group, stearoyloxy group, benzoyloxy A group, p-methoxyphenyl carbony
  • a carbamoyloxy group (preferably a carbamoyloxy group having a carbon number of 1 to 30.
  • An alkoxycarbonyloxy group preferably, an alkoxycarbonyloxy group having a carbon number of 2 to 30, for example, a methoxycarbonyloxy group, an ethoxycarbonyloxy group, a t-butoxycarbonyloxy group, an n-octylcarbonyloxy group
  • An aryloxycarbonyloxy group (preferably, an aryloxycarbonyloxy group having a carbon number of 7 to 30, for example, a phenoxycarbonyloxy group, a p-me
  • amino group methylamino group, dimethylamino group, anilino group, N-methyl-anilino group , Diphenylamino group
  • Acylamino group preferably, formylamino group, alkylcarbonylamino group having 1 to 30 carbon atoms, arylcarbonylamino group having 6 to 30 carbon atoms.
  • Aminocarbonylamino group preferably, an aminocarbonylamino group having 1 to 30 carbon atoms, such as carbamoylamino group, N, N-dimethylaminocarbonylamino group, N, N-diethylaminocarbonylamino group, morpholino carbonylamino group); Alkoxycarbonylamino group (preferably an alkoxycarbonylamino group having a carbon number of 2 to 30.
  • methoxycarbonylamino group ethoxycarbonylamino group, t-butoxycarbonylamino group, n-octadecyloxycarbonylamino group, N-methyl-methoxy Carbonylamino group
  • An aryloxycarbonylamino group preferably, an aryloxycarbonylamino group having a carbon number of 7 to 30, for example, a phenoxycarbonylamino group, a p-chlorophenoxycarbonylamino group, an mn-octyloxyphenoxycarbonylamino group
  • a sulfamoylamino group preferably, a sulfamoylamino group having a carbon number of 0 to 30, for example, a sulfamoylamino group, an N, N-dimethylaminosulfonylamino group, an Nn-octylaminosulfonylamino group
  • An alkylthio group preferably, an alkylthio group having 1 to 30 carbon atoms, such as a methylthio group, an ethylthio group, an n-hexadecylthio group
  • An arylthio group preferably an arylthio group having a carbon number of 6 to 30, for example, a phenylthio group, a p-chlorophenylthio group, an m-methoxyphenylthio group
  • a heterocyclic thio group preferably a heterocyclic thio group having a carbon number of 2 to 30, for example, 2-benzothiazo
  • a sulfamoyl group (preferably a sulfamoyl group having a carbon number of 0 to 30.
  • An acyl group (preferably a formyl group, an alkylcarbonyl group having 2 to 30 carbon atoms, an arylcarbonyl group having 7 to 30 carbon atoms, a heterocyclic carbonyl group bonded to the carbonyl group at a carbon atom having 4 to 30 carbon atoms.
  • An aryloxycarbonyl group preferably, an aryloxycarbonyl group having a carbon number of 7 to 30, for example, a phenoxycarbonyl group, an o-chlorophenoxycarbonyl group, an m-nitrophenoxycarbonyl group, a p-t-butylphenoxycarbonyl group
  • An alkoxycarbonyl group preferably, an alkoxycarbonyl group having a carbon number of 2 to 30, for example, a methoxycarbonyl group, an ethoxycarbonyl group, a t-butoxycarbonyl group, an n-octadecyl
  • carbamoyl group N-methylcarbamoyl group, N, N-dimethylcarbamoyl group, N, N-di-n-octylcarbamoyl group, N- (methyl) Sulfonyl) carbamoyl group);
  • An aryl or heterocyclic azo group preferably an arylazo group having 6 to 30 carbon atoms, a heterocyclic azo group having 3 to 30 carbon atoms, for example, a phenylazo group, p-chlorophenylazo group, 5-ethylthio-1,3,4- Thiadiazol-2-ylazo group
  • Imide group preferably, N-succinimide group, N-phthalimide group
  • Phosphino group preferably, phosphino group having 2 to 30 carbon atoms, for example, dimethyl phosphino group, diphenyl phosphino group, methyl phenoxy phosphino group
  • one or more hydrogen atoms may be substituted with the above-mentioned substituent T for groups having a hydrogen atom.
  • functional groups include alkylcarbonylaminosulfonyl group, arylcarbonylaminosulfonyl group, alkylsulfonylaminocarbonyl group and arylsulfonylaminocarbonyl group. Specific examples thereof include a methylsulfonylaminocarbonyl group, a p-methylphenylsulfonylaminocarbonyl group, an acetylaminosulfonyl group, a benzoylaminosulfonyl group and the like.
  • X and Y each independently represent an electron-withdrawing group. X and Y may be bonded to each other to form a ring.
  • the electron withdrawing group represented by X and Y is preferably a substituent having a Hammett's substituent constant ⁇ p value of positive.
  • the electron withdrawing group include cyano group, acyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, sulfonyl group, sulfinyl group and sulfamoyl group.
  • the acyl group is preferably an acetyl group, a propionyl group, a pivaloyl group, a benzoyl group or a 4-methoxybenzoyl group.
  • alkoxycarbonyl group examples include methoxycarbonyl group, ethoxycarbonyl group, 2-hydroxyethoxycarbonyl group, 2- (3-trimethoxysilylpropylaminocarbonyloxy) ethoxycarbonyl group, 2- (3-triethoxysilylpropylaminocarbonyloxy ) Ethoxycarbonyl group and 2-ethylhexyl carbonyloxy group are preferable.
  • an aryloxy carbonyl group a phenoxy carbonyl group and 4-methoxy phenoxycarbonyl group are preferable.
  • carbamoyl group unsubstituted carbamoyl group, N, N-dimethylcarbamoyl group, N, N-diethylcarbamoyl group, morpholino carbamoyl group, N, N-di-n-octylcarbamoyl group, Nn-octylcarbamoyl group Is preferred.
  • the sulfonyl group is preferably a methanesulfonyl group, an ethanesulfonyl group, an octanesulfonyl group, or a benzenesulfonyl group.
  • the sulfinyl group is preferably a methanesulfinyl group, an ethanesulfinyl group, an octanesulfinyl group, or a benzenesulfinyl group.
  • the sulfamoyl group is preferably an unsubstituted sulfamoyl group or an N, N-dimethylsulfamoyl group.
  • an electron withdrawing group which X and Y represent a cyano group and a carbamoyl group are preferable, and a carbamoyl group is more preferable.
  • X and Y may be bonded to each other to form a ring.
  • the ring formed by combining X and Y is preferably a 5- or 6-membered ring. Specifically, 5-pyrazolone ring, isoxazolin-5-one ring, pyrazolidine-3,5-dione ring, barbituric acid ring, thiobarbituric acid ring, dihydropyridine-2,6-dione ring, etc. are mentioned.
  • Be The ring formed by combining X and Y may further have a substituent. Examples of the substituent include the groups described above for the substituent T.
  • X and Y are carbamoyl groups (which may be combined to form a ring). More preferably, X and Y are combined to form a pyrazolidine-3,5-dione ring.
  • the compound represented by the formula (3) is preferably a compound represented by the following formula (3a).
  • R 13 and R 14 are each independently an aliphatic group, an aromatic group or a heterocyclic group. R 13 and R 14 may be bonded to each other to form a ring.
  • R 13 and R 14 of formula (3a) has the same meaning as R 13 and R 14 of formula (4) described below, and preferred ranges are also the same.
  • Me represents a methyl group and Ph represents a phenyl group.
  • each of R 11 and R 12 independently represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group or an aryloxy group.
  • X and Y each independently represent an electron withdrawing group.
  • R 11 and R 12 may be bonded to each other to form a ring, and X and Y may be bonded to each other to form a ring.
  • R 11 and R 12 of formula (1) has the same meaning as R 11 and R 12 of formula (2), and preferred ranges are also the same.
  • X and Y of Formula (1) are synonymous with X and Y of Formula (3), and their preferable ranges are also the same.
  • the compound represented by Formula (1) is preferably a compound represented by Formula (4).
  • each of R 11 and R 12 independently represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group or an aryloxy group.
  • R 13 and R 14 each independently represent an aliphatic group, an aromatic group or a heterocyclic group.
  • R 11 and R 12 may be bonded to each other to form a ring, and R 13 and R 14 may be bonded to each other to form a ring.
  • R 11 and R 12 of formula (4) has the same meaning as R 11 and R 12 of formula (2), and preferred ranges are also the same.
  • R 13 and R 14 each independently represent an aliphatic group, an aromatic group or a heterocyclic group.
  • the carbon number of the aliphatic group represented by R 13 and R 14 is preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 15, particularly preferably 1 to 10, and most preferably 1 to 7.
  • an alkyl group, an alkenyl group, an alkynyl group and an aralkyl group are mentioned, An alkyl group or an alkenyl group is preferable, and an alkyl group is more preferable.
  • the alkyl group, the alkenyl group, the alkynyl group and the aralkyl group may have a substituent. Examples of the substituent include the groups described above for the substituent T.
  • the carbon number of the alkyl group is preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 15, particularly preferably 1 to 10, and most preferably 1 to 7.
  • the alkyl group may be linear, branched or cyclic, preferably linear or branched, and more preferably linear.
  • the carbon number of the alkenyl group is preferably 2 to 30, more preferably 2 to 20, still more preferably 2 to 15, particularly preferably 2 to 10, and most preferably 2 to 7.
  • the alkenyl group may be linear, branched or cyclic, preferably linear or branched, and more preferably linear.
  • the carbon number of the alkynyl group is preferably 2 to 30, more preferably 2 to 20, still more preferably 2 to 15, particularly preferably 2 to 10, and most preferably 2 to 7.
  • the alkynyl group may be linear, branched or cyclic, preferably linear or branched, and more preferably linear.
  • the number of carbon atoms of the aralkyl group is preferably 7 to 30, more preferably 7 to 20, and still more preferably 7 to 15.
  • the alkyl part of the aralkyl group is the same as the above alkyl group.
  • the aryl part of the aralkyl group is the same as the following aryl group.
  • the aromatic group includes an aryl group.
  • the carbon number of the aromatic group is preferably 6 to 40, more preferably 6 to 30, still more preferably 6 to 20, particularly preferably 6 to 15, and most preferably 6 to 12.
  • a phenyl group and a naphthyl group are preferable, and a phenyl group is more preferable.
  • the aryl group may have a substituent. Examples of the substituent include the groups described above for the substituent T.
  • the heterocycle in the heterocycle group preferably contains a 5- or 6-membered saturated or unsaturated heterocycle.
  • the heterocyclic ring may be fused with an aliphatic ring, an aromatic ring or another heterocyclic ring.
  • As a hetero atom which comprises the ring of a heterocyclic ring B, N, O, S, Se and Te are mentioned, N, O and S are preferable.
  • the hetero ring is preferably a carbon atom having a free valence (monovalent) (the hetero ring group is bonded at a carbon atom).
  • the carbon number of the heterocyclic group is preferably 1 to 40, more preferably 1 to 30, and still more preferably 1 to 20.
  • Examples of saturated heterocycles in the heterocycle group include pyrrolidine ring, morpholine ring, 2-bora-1,3-dioxolane ring and 1,3-thiazolidine ring.
  • Examples of the unsaturated heterocyclic ring in the heterocyclic group include an imidazole ring, a thiazole ring, a benzothiazole ring, a benzoxazole ring, a benzotriazole ring, a benzoselenazole ring, a pyridine ring, a pyrimidine ring and a quinoline ring.
  • the heterocyclic group may have a substituent. Examples of the substituent include the groups described above for the substituent T.
  • R 13 and R 14 are preferably each independently an aliphatic group or an aromatic group, and are an aliphatic group having 1 to 30 carbon atoms or an aromatic group having 6 to 30 carbon atoms Is more preferable, and an aliphatic group having 1 to 20 carbon atoms is more preferable.
  • R 13 and R 14 are preferably each independently an alkyl group having 1 to 20 carbon atoms or an aralkyl group having 7 to 20 carbon atoms, more preferably an alkyl group having 1 to 15 carbon atoms, and carbon More preferably, it is a linear alkyl group of 1 to 10, and most preferably a linear alkyl group of 1 to 7 carbon atoms.
  • R 13 and R 14 may be bonded to each other to form a ring.
  • the ring formed by combining R 13 and R 14 is preferably a 5- or 6-membered ring.
  • Ph represents a phenyl group.
  • the composition of the present invention is a composition containing the compound represented by the above-mentioned formula (1).
  • This composition has a ratio of a molar absorption coefficient ⁇ 385 at a wavelength of 385 nm to a molar absorption coefficient ⁇ 430 at a wavelength of 430 nm in a spectral absorption spectrum measured in methanol, and ⁇ 430 / ⁇ 385 is 0.015 to 0. It is characterized by being 028.
  • the molar absorption coefficient ratio is preferably 0.018 or more, more preferably 0.020 or more, still more preferably 0.021 or more, and particularly preferably 0.022 or more. preferable.
  • the molar absorption coefficient ratio is preferably 0.027 or less, more preferably 0.026 or less, and still more preferably 0.025 or less. Those having a ratio of such molar absorption coefficients have excellent absorption of light in the visible region near the ultraviolet region despite the high absorption near the wavelength of 385 nm, and therefore the absorption of ultraviolet light on the longer wavelength side While excellent, it has excellent visible transparency.
  • composition of the present invention can be preferably used as a UV absorber.
  • composition of the present invention can be preferably used for packaging materials, containers, paints, coatings, inks, fibers, building materials, recording media, image display devices, covers for solar cells, glass articles, cosmetic preparations and the like. .
  • the details of these can be referred to the description of Paragraph Nos. 0158 to 0218 of JP 2009-263617 A, the contents of which are incorporated herein.
  • composition of the present invention is preferably a reactant obtained by the method of producing a compound of the present invention described above.
  • the content of the compound represented by the formula (1) in the composition of the present invention is preferably 1% by mass or more, more preferably 50% by mass or more, and further preferably 90% by mass or more Preferably, the content is 95% by mass or more, more preferably 99% by mass or more. Moreover, it is particularly preferable that the composition of the present invention is constituted only by the compound represented by the formula (1).
  • the curable composition of the present invention comprises the composition of the present invention described above and a curable compound.
  • the curable compound include a compound having a group having an ethylenically unsaturated bond, a compound having an epoxy group, a compound having a methylol group, and a compound having a —O—Si—O— structure.
  • the group having an ethylenically unsaturated bond include a vinyl group, a (meth) allyl group and a (meth) acryloyl group.
  • the curable compound it is preferable to use a compound having an —O—Si—O— structure as the curable compound. According to this aspect, it is possible to manufacture a glass article or the like which is low in coloring and excellent in ultraviolet absorptivity.
  • a glass article the window glass for motor vehicles, the window glass for construction materials, etc. can be mentioned.
  • the compound having a -O-Si-O- structure is preferably a hydrolyzable silicon compound, more preferably a hydrolyzable alkoxysilane, and further preferably a trifunctional or tetrafunctional alkoxysilane. preferable.
  • the compound having a -O-Si-O- structure include tetramethoxysilane, tetraethoxysilane, tetra-n-propoxysilane, tetra-i-propoxysilane, tetra-n-butoxysilane, methyltrimethoxysilane Methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, n-propyltrimethoxysilane, n-propyltriethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, ⁇ -glycidyloxypropyltrimethoxysilane, ⁇ -Glycidyloxypropyltriethoxysilane, ⁇ -glycidyloxypropylmethyldimethoxysilane, ⁇ -glycidyloxypropylmethyldie
  • the content of the compound represented by the formula (1) in the total solid content of the curable composition of the present invention is preferably 0.01 to 20% by mass.
  • the content of the composition of the present invention described above in the total solid content of the curable composition of the present invention is preferably 0.01 to 20% by mass, and 0.1 to 10% by mass. Is more preferred.
  • the content of the curable compound in the total solid content of the curable composition of the present invention is preferably 0.1 to 99.9% by mass.
  • the curable composition of the present invention can further contain another ultraviolet absorber other than the compound represented by Formula (1).
  • another ultraviolet absorber the ultraviolet absorber described in Paragraph No. 0065 of international publication WO 2017/122503 can be mentioned, and these can be used.
  • the curable composition of the present invention can further contain a solvent.
  • the solvent is not particularly limited, and examples thereof include water and alcohol solvents.
  • alcohol solvents methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, 2-methyl-1-propanol, 1-methoxy-2-propanol, 2-ethoxyethanol, 2-butoxy Ethanol, polyethylene glycol monoalkyl ether, polypropylene glycol monoalkyl ether, ethylene glycol, propylene glycol, polyethylene glycol, polypropylene glycol, glycerin and the like can be mentioned.
  • ethylene carbonate, N-methyl pyrrolidone, dioxane, tetrahydrofuran, ethylene glycol dialkyl ether, propylene glycol dialkyl ether, polyethylene glycol dialkyl ether, polypropylene glycol dialkyl ether, acetonitrile, propionitrile, benzonitrile, carboxylic acid ester, Phosphoric acid esters, phosphonic acid esters, dimethylsulfoxide, sulfolane, dimethylformamide, dimethylacetamide and the like can be used. These may be used alone or in combination of two or more.
  • the content of the solvent is preferably 10 to 90% by mass with respect to the total amount of the curable composition.
  • the curable composition of the present invention can contain a catalyst.
  • a catalyst When a compound having an —O—Si—O— structure is used as the curable compound, it is preferable that the catalyst be contained. According to this aspect, the sol-gel reaction is promoted, and a stronger film is easily obtained.
  • the catalyst include acid catalysts such as hydrochloric acid, sulfuric acid, acetic acid and propionic acid, and base catalysts such as sodium hydroxide, potassium hydroxide and triethylamine.
  • the content of the catalyst is preferably 0.1 to 100 parts by mass, more preferably 0.1 to 50 parts by mass, still more preferably 0.1 to 20 parts by mass with respect to 100 parts by mass of the curable compound. .
  • the curable composition of the present invention may contain only one type of catalyst, or may contain two or more types. When two or more catalysts are contained, the total amount thereof is preferably in the above range.
  • Example 1 Compound (1) -1 was produced according to the following scheme.
  • Example 2 Compound (1) -2 as a target compound was treated in the same manner as in Example 1 except that the same amount of compound (3) -2 was used instead of compound (3) -1 in Example 1. The product contained was obtained.
  • Example 3 Example 1 was repeated except that the same amount of compound (3) -3 was used instead of compound (3) -1 in the same manner as in Example 1 to obtain compound (1) -3 as a target compound. The product contained was obtained.
  • Example 4 A product containing compound (1) -1 as a target compound was obtained in the same manner as in Example 1 except that the same amount of dimethylacetamide was used instead of NMP as the reaction solvent in Example 1.
  • Example 5 A product containing compound (1) -1 as a target compound was obtained in the same manner as in Example 1 except that the same amount of dimethylformamide was used instead of NMP as the reaction solvent in Example 1.
  • Example 6 A product containing compound (1) -1 as a target compound was obtained in the same manner as in Example 1 except that the same amount of p-toluenesulfonic acid was used instead of methanesulfonic acid in Example 1. .
  • Example 7 A product containing compound (1) -1 as a target compound was obtained in the same manner as in Example 1 except that methanesulfonic acid was added in Example 1.
  • Example 8 A product containing compound (1) -1 as a target compound was obtained in the same manner as in Example 1 except that the same amount of sulfolane was used in place of NMP as the reaction solvent in Example 1.
  • Comparative Example 2 Compound (1) -2 as a target compound was treated in the same manner as in Comparative Example 1 except that the same amount of compound (3) -2 was used instead of compound (3) -1 in Comparative Example 1. The product contained was obtained.
  • Comparative Example 3 Compound (1) -3 as a target compound was treated in the same manner as in Comparative Example 1 except that the same amount of compound (3) -3 was used instead of compound (3) -1 in Comparative Example 1. The product contained was obtained.
  • the products containing the target compounds obtained by the methods of Examples 1 to 8 were less colored than those obtained by the methods of Comparative Examples.
  • the value of ⁇ 430 / ⁇ 385 was smaller than that of the comparative example. Note that a small value of ⁇ 430 / ⁇ 385 means that the absorption of light with a wavelength of 385 nm is large, and that the absorption of light with a wavelength of 430 nm is almost nonexistent. That is, it means that the coloring is small and the absorption of ultraviolet light on the long wavelength side is excellent.
  • Example 101 After mixing 1.20 g of the product containing compound (1) -1 obtained in Example 1, 2.71 g of 3-triethoxysilylpropyl isocyanate, and 20 mL of dry tetrahydrofuran, One drop of ethyl ethylhexanoate) tin was added and heated to reflux for 3 hours under nitrogen atmosphere. Next, 80.4 mg of tetraethoxysilane, 0.602 g of glycidyloxypropyltrimethoxysilane, 1.73 g of ultrapure water, and acetic acid which is an acid catalyst 17.4 of 0.476 g of the mixed solution after heating and refluxing.
  • the mixture was stirred for 30 seconds, then irradiated with ultrasonic waves for 3 minutes, and then stirred in a 50 ° C. water bath for 1 hour to obtain a curable composition.
  • the resulting curable composition was coated on a 0.1 mass% KOH-treated glass substrate using a 30 mil (1 mil is 2.54 ⁇ 10 ⁇ 5 m) doctor blade, and the coating film was prepared by Stationary drying was carried out at 80 ° C. for 30 minutes using a blower dryer. Then, it heated at 200 degreeC for 30 minutes, and produced the glass article.
  • Example 101 in place of the compound (1) -1 obtained in Example 1, the products containing the target compounds obtained in Examples 2 to 8 and Comparative Examples 1 to 3 were used, respectively.
  • a glass article was produced in the same manner as in Example 101.
  • the example had a higher T450 / T410 value than the comparative example, and had excellent transparency.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Cosmetics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention concerne un procédé de production d'un composé capable de produire un composé de benzothiol ayant une faible coloration, une composition et une composition durcissable. Le procédé est destiné à produire un composé représenté par la formule (1) et comprend la mise en réaction d'un composé représenté par la formule (2) avec un composé représenté par la formule (3) en présence d'un agent réducteur. Dans les formules, R11 et R12 représentent chacun indépendamment un atome d'hydrogène, etc. ; R21 et R22 représentent chacun indépendamment un groupe alkyle ; A1 et A2 représentent chacun indépendamment OH ou O-, à condition que A1 et/ou A2 représente OH ; X et Y représentent chacun indépendamment un groupe électroattracteur ; Z représente un anion de valence n ; n est un nombre entier supérieur ou égal à 1 ; et lorsque soit A1 soit A2 représente O-, alors Z est absent.
PCT/JP2018/031640 2017-09-26 2018-08-28 Procédé de production de composé, composition et composition durcissable WO2019065043A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2020261886A1 (fr) * 2019-06-28 2020-12-30

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4911155B1 (fr) * 1970-04-17 1974-03-15
JP2009242717A (ja) * 2008-03-31 2009-10-22 Fujifilm Corp 液晶組成物、位相差板、偏光板、並びに液晶表示装置
JP2009263617A (ja) * 2008-03-31 2009-11-12 Fujifilm Corp 紫外線吸収材料
JP2010100787A (ja) * 2008-10-27 2010-05-06 Fujifilm Corp 紫外線吸収剤およびこれを含む高分子材料
WO2015080218A1 (fr) * 2013-11-29 2015-06-04 Dic株式会社 Composé polymérisable, composition, polymère, corps optiquement anisotrope, élément d'affichage à cristaux liquides, et élément el organique
WO2016147773A1 (fr) * 2015-03-13 2016-09-22 富士フイルム株式会社 Composition de formation de film semi-conducteur organique, transistor à film mince organique, papier électronique et dispositif d'affichage
WO2017122503A1 (fr) * 2016-01-12 2017-07-20 富士フイルム株式会社 Composition, film, article en verre, composé, composition de grande pureté, procédé de production d'un composé et procédé de production d'un film

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4911155A (fr) * 1972-05-30 1974-01-31
US7514206B2 (en) * 2006-04-13 2009-04-07 Carestream Health, Inc. Thermally developable materials with buried conductive backside coatings
JP2009256304A (ja) * 2008-03-21 2009-11-05 Fujifilm Corp ビスベンゾジチオール化合物の製造方法
MY166236A (en) * 2016-01-12 2018-06-22 Fuji Electric Co Ltd Magnetic recording medium and method for producing same

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4911155B1 (fr) * 1970-04-17 1974-03-15
JP2009242717A (ja) * 2008-03-31 2009-10-22 Fujifilm Corp 液晶組成物、位相差板、偏光板、並びに液晶表示装置
JP2009263617A (ja) * 2008-03-31 2009-11-12 Fujifilm Corp 紫外線吸収材料
JP2010100787A (ja) * 2008-10-27 2010-05-06 Fujifilm Corp 紫外線吸収剤およびこれを含む高分子材料
WO2015080218A1 (fr) * 2013-11-29 2015-06-04 Dic株式会社 Composé polymérisable, composition, polymère, corps optiquement anisotrope, élément d'affichage à cristaux liquides, et élément el organique
WO2016147773A1 (fr) * 2015-03-13 2016-09-22 富士フイルム株式会社 Composition de formation de film semi-conducteur organique, transistor à film mince organique, papier électronique et dispositif d'affichage
WO2017122503A1 (fr) * 2016-01-12 2017-07-20 富士フイルム株式会社 Composition, film, article en verre, composé, composition de grande pureté, procédé de production d'un composé et procédé de production d'un film

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2020261886A1 (fr) * 2019-06-28 2020-12-30
WO2020261886A1 (fr) * 2019-06-28 2020-12-30 富士フイルム株式会社 Absorbeur de rayons ultraviolets, composition absorbant les rayons ultraviolets, film, stratifié et nouveau composé absorbant les rayons ultraviolets
JP7279162B2 (ja) 2019-06-28 2023-05-22 富士フイルム株式会社 紫外線吸収剤、紫外線吸収組成物、紫外線吸収膜、積層体及び新規化合物

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