WO2019188508A1 - 増粘安定剤、及びそれを用いた電子デバイス製造用溶剤組成物 - Google Patents
増粘安定剤、及びそれを用いた電子デバイス製造用溶剤組成物 Download PDFInfo
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- WO2019188508A1 WO2019188508A1 PCT/JP2019/011207 JP2019011207W WO2019188508A1 WO 2019188508 A1 WO2019188508 A1 WO 2019188508A1 JP 2019011207 W JP2019011207 W JP 2019011207W WO 2019188508 A1 WO2019188508 A1 WO 2019188508A1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/36—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/08—Preparation of carboxylic acid amides from amides by reaction at nitrogen atoms of carboxamide groups
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C291/00—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00
- C07C291/02—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds
- C07C291/04—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds containing amino-oxide bonds
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- 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
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
- C09D11/033—Printing inks characterised by features other than the chemical nature of the binder characterised by the solvent
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/20—Diluents or solvents
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
Definitions
- the present invention relates to a novel compound that thickens and stabilizes a fluid organic substance such as oil and a solvent composition for producing an electronic device containing the compound.
- the method of thickening and stabilizing the liquid is a very important technology in the industry.
- a metastable emulsion of mayonnaise or salad dressing can stably maintain the emulsion for a long period of time. This is because the aqueous component is thickened and stabilized. For this reason, various thickening stabilizers have been developed.
- an alkyl acrylate copolymer As a compound that thickens and stabilizes an aqueous medium, for example, an alkyl acrylate copolymer is known.
- 12-hydroxystearic acid is known as a thickening stabilizer for fluid organic substances (for example, organic substances having fluidity such as oily media) (Patent Document 1, etc.).
- 12-Hydroxystearic acid is mainly used for its gelling action for disposal of edible oil.
- 12-hydroxystearic acid could not adjust the degree of gelation and could only be induced to either solidify or remain liquid. That is, the present condition is that the compound which thickens a fluid organic substance to desired viscosity has not been found yet.
- an object of the present invention is to provide a compound capable of thickening a fluid organic substance to a desired viscosity and stabilizing the composition uniformly.
- Another object of the present invention is to provide a precursor of the compound capable of thickening a fluid organic substance to a desired viscosity and stabilizing the composition uniformly.
- Another object of the present invention is to provide a solvent composition that contains a compatible product of the compound and a flowable organic substance and that is suitably used for manufacturing an electronic device.
- Still another object of the present invention is to provide a method for producing the solvent composition.
- the inventors of the present invention can increase the viscosity of a fluid organic substance by dissolving the compound represented by the following formula (1) with the fluid organic substance. , That a compatibilized material having a uniform composition (preventing sedimentation, local aggregation, or concentration of the composition and maintaining a uniform state stably) can be obtained, represented by the following formula (1): It has been found that the viscosity of the obtained compatible product can be controlled by adjusting the carbon number of the resulting compound. The present invention has been completed based on these findings.
- R 1 is a monovalent linear aliphatic hydrocarbon group having 10 to 25 carbon atoms
- R 2 and R 3 are the same or different, and are divalent divalent having 2, 4, 6, or 8 carbon atoms.
- R 4 represents an aliphatic hydrocarbon group, a bivalent alicyclic hydrocarbon group having 6 carbon atoms, or a divalent aromatic hydrocarbon group, and R 4 represents a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms.
- R 5, R 6 are the same or different, .L 1 ⁇ L 3 showing a monovalent aliphatic hydrocarbon group, or a hydroxyalkyl ether group having 1 to 3 carbon atoms represents an amide bond, and L 1 When L 3 is —CONH—, L 2 is —NHCO—, and when L 1 and L 3 are —NHCO—, L 2 is —CONH—) The compound represented by these is provided.
- the present invention also provides the following formula (2): (Wherein R 1 is a monovalent linear aliphatic hydrocarbon group having 10 to 25 carbon atoms, R 2 and R 3 are the same or different, and are divalent divalent having 2, 4, 6, or 8 carbon atoms. R 4 represents an aliphatic hydrocarbon group, a bivalent alicyclic hydrocarbon group having 6 carbon atoms, or a divalent aromatic hydrocarbon group, and R 4 represents a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms.
- R 5, R 6 are the same or different, .L 1 ⁇ L 3 showing a monovalent aliphatic hydrocarbon group, or a hydroxyalkyl ether group having 1 to 3 carbon atoms represents an amide bond, and L 1 When L 3 is —CONH—, L 2 is —NHCO—, and when L 1 and L 3 are —NHCO—, L 2 is —CONH—) The compound represented by these is provided.
- the compound represented by the following formula (3) and the compound represented by the following formula (4) are reacted, or the compound represented by the following formula (3 ′) and the following formula (
- a method for producing a compound represented by the formula (2) is provided, in which a compound represented by the following formula (2) is obtained by reacting the compound represented by 4 ′).
- R 1 is a monovalent linear aliphatic hydrocarbon group having 10 to 25 carbon atoms
- R 2 and R 3 are the same or different, and are divalent divalent having 2, 4, 6, or 8 carbon atoms.
- R 4 represents an aliphatic hydrocarbon group, a bivalent alicyclic hydrocarbon group having 6 carbon atoms, or a divalent aromatic hydrocarbon group, and R 4 represents a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms.
- R 5, R 6 are the same or different, .L 1 ⁇ L 3 showing a monovalent aliphatic hydrocarbon group, or a hydroxyalkyl ether group having 1 to 3 carbon atoms represents an amide bond, and L 1 When L 3 is —CONH—, L 2 is —NHCO—, and when L 1 and L 3 are —NHCO—, L 2 is —CONH— R 7 is a hydrogen atom or 1 carbon atom And in formula (3), OR 7 forms a ring by dehydration condensation or dealcoholization condensation with a hydrogen atom constituting L 2. May be)
- the present invention also provides the following formula (2): (Wherein R 1 is a monovalent linear aliphatic hydrocarbon group having 10 to 25 carbon atoms, R 2 and R 3 are the same or different, and are divalent divalent having 2, 4, 6, or 8 carbon atoms. R 4 represents an aliphatic hydrocarbon group, a bivalent alicyclic hydrocarbon group having 6 carbon atoms, or a divalent aromatic hydrocarbon group, and R 4 represents a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms.
- R 5, R 6 are the same or different, .L 1 ⁇ L 3 showing a monovalent aliphatic hydrocarbon group, or a hydroxyalkyl ether group having 1 to 3 carbon atoms represents an amide bond, and L 1 When L 3 is —CONH—, L 2 is —NHCO—, and when L 1 and L 3 are —NHCO—, L 2 is —CONH—)
- a compound represented by the formula (1) (Wherein R 1 to R 6 and L 1 to L 3 are the same as above) The manufacturing method of the compound represented by Formula (1) which obtains the compound represented by is provided.
- the present invention also provides a solvent composition for producing an electronic device comprising a compatible product of the compound represented by the above formula (1) and a fluid organic substance.
- the present invention also provides that the fluid organic substance is at least one selected from hydrocarbon oils, ethers, halogenated hydrocarbons, petroleum components, animal and vegetable oils, silicone oils, esters, aromatic carboxylic acids, pyridines, and alcohols.
- the above-mentioned solvent composition for producing an electronic device is provided.
- the present invention also provides the following formula (1): (Wherein R 1 is a monovalent linear aliphatic hydrocarbon group having 10 to 25 carbon atoms, R 2 and R 3 are the same or different, and are divalent divalent having 2, 4, 6, or 8 carbon atoms. R 4 represents an aliphatic hydrocarbon group, a bivalent alicyclic hydrocarbon group having 6 carbon atoms, or a divalent aromatic hydrocarbon group, and R 4 represents a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms.
- R 5, R 6 are the same or different, .L 1 ⁇ L 3 showing a monovalent aliphatic hydrocarbon group, or a hydroxyalkyl ether group having 1 to 3 carbon atoms represents an amide bond, and L 1 When L 3 is —CONH—, L 2 is —NHCO—, and when L 1 and L 3 are —NHCO—, L 2 is —CONH—)
- the manufacturing method of the solvent composition for electronic device manufacture which obtains the said solvent composition for electronic device manufacture through the process of compatibilizing the compound and fluid organic substance which are represented by this is provided.
- the compound represented by the formula (1) of the present invention is easily mixed with a fluid organic substance to easily thicken the fluid organic substance and make the composition of the composition containing the fluid organic substance uniform. Can be stabilized. Therefore, it can be suitably used as a thickening stabilizer for paints, adhesives, inks, lubricants, pharmaceuticals, quasi drugs, cosmetics, and the like.
- the compound represented by the formula (2) of the present invention is oxidized, the compound represented by the formula (1) useful as described above can be easily produced. That is, the compound represented by the formula (2) is extremely useful as a precursor of the compound represented by the formula (1).
- the solvent composition for electronic device manufacture of this invention containing the compound represented by the said Formula (1) has moderate viscosity and shear thinning property. For this reason, it is difficult for the liquid to sag and has good coating properties (or ejection properties). Furthermore, compared with a solvent composition obtained by thickening a fluid organic substance with ethyl cellulose, the solvent composition for manufacturing an electronic device of the present invention can be fired at a low temperature, and the coating composition to which the solvent composition is applied is applied. The body can be prevented from being softened and deformed by being exposed to high temperature for a long time. In addition, the residual amount of ash after baking can be significantly reduced, and the occurrence of various problems caused by the residual ash (for example, deterioration of electrical characteristics when used in conductive ink) is suppressed. be able to.
- FIG. 3 is a diagram showing a 1 H-NMR measurement result of a compound (2-3) obtained in an example.
- FIG. 3 is a diagram showing a 1 H-NMR measurement result of a compound (1-3) obtained in an example.
- FIG. 3 is a diagram showing a 1 H-NMR measurement result of a compound (2-4) obtained in an example.
- FIG. 3 is a diagram showing a 1 H-NMR measurement result of a compound (1-4) obtained in an example.
- FIG. 3 is a diagram showing a 1 H-NMR measurement result of a compound (2-1) obtained in an example.
- FIG. 3 is a diagram showing a 1 H-NMR measurement result of a compound (1-1) obtained in an example.
- the compound (1) of the present invention is represented by the following formula (1).
- R 1 is a monovalent linear aliphatic hydrocarbon group having 10 to 25 carbon atoms
- R 2 and R 3 are the same or different, and are divalent divalent having 2, 4, 6, or 8 carbon atoms.
- R 4 represents an aliphatic hydrocarbon group, a bivalent alicyclic hydrocarbon group having 6 carbon atoms, or a divalent aromatic hydrocarbon group, and R 4 represents a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms.
- R 5, R 6 are the same or different, .L 1 ⁇ L 3 showing a monovalent aliphatic hydrocarbon group, or a hydroxyalkyl ether group having 1 to 3 carbon atoms represents an amide bond, and L 1 When L 3 is —CONH—, L 2 is —NHCO—, and when L 1 and L 3 are —NHCO—, L 2 is —CONH—)
- R 1 is a monovalent linear aliphatic hydrocarbon group having 10 to 25 carbon atoms, such as decyl group, lauryl group, myristyl group, pentadecyl group, stearyl group, palmityl group, nonadecyl group, eicosyl group, behenyl.
- a linear alkyl group such as a group; a linear alkenyl group such as a decenyl group, a pentadecenyl group, an oleyl group and an eicosenyl group; a linear alkynyl group such as a pentadecynyl group, an octadecynyl group and a nonadecynyl group.
- R 1 is a monovalent compound having 14 to 25 carbon atoms because it is excellent in the thickening effect of the fluid organic substance and can suppress the remaining of ash to an extremely low level even when fired at a low temperature.
- a linear aliphatic hydrocarbon group (particularly preferably, an alkyl group having 14 to 25 carbon atoms) is preferable, and a monovalent linear aliphatic hydrocarbon group having 18 to 21 carbon atoms (particularly preferably) is particularly preferable.
- Examples of the divalent aliphatic hydrocarbon group having 2, 4, 6, or 8 carbon atoms in R 2 and R 3 include an ethylene group, an n-butylene group, an n-hexylene group, and an n-octylene group. .
- Examples of the divalent alicyclic hydrocarbon group having 6 carbon atoms in R 2 and R 3 include a 1,4-cyclohexylene group, a 1,3-cyclohexylene group, and a 1,2-cyclohexylene group. .
- Examples of the divalent aromatic hydrocarbon group in R 2 and R 3 include arylene groups having 6 to 10 carbon atoms such as 1,4-phenylene group, 1,3-phenylene group and 1,2-phenylene group. Can be mentioned.
- a divalent aliphatic hydrocarbon group having 2, 4, 6, or 8 carbon atoms (particularly preferably a straight chain) is preferable in that the thickening effect of the fluid organic substance is excellent.
- -Like alkylene group is preferable, more preferably a divalent aliphatic hydrocarbon group having 2, 4, or 6 carbon atoms (particularly preferably a linear alkylene group), particularly preferably a divalent group having 2 or 4 carbon atoms.
- an aliphatic hydrocarbon group (particularly preferably a linear alkylene group) most preferably a divalent aliphatic hydrocarbon group having 2 carbon atoms (particularly preferably a linear alkylene group).
- R 4 represents a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms, and among them, a linear or branched alkylene group is preferable and particularly preferable from the viewpoint of excellent thickening effect of a fluid organic substance. Is a linear alkylene group.
- R 4 represents a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms, and among them, a divalent aliphatic hydrocarbon group having 1 to 7 carbon atoms is more preferable because it is excellent in the thickening effect of the fluid organic substance.
- Aliphatic hydrocarbon group particularly preferably a divalent aliphatic hydrocarbon group having 3 to 7 carbon atoms, most preferably a divalent aliphatic hydrocarbon group having 3 to 6 carbon atoms, particularly preferably 3 to 5 carbon atoms These are divalent aliphatic hydrocarbon groups.
- R 4 is preferably a linear or branched alkylene group having 1 to 8 carbon atoms, more preferably a linear alkylene group having 1 to 7 carbon atoms, particularly preferably a straight chain group having 3 to 7 carbon atoms.
- a linear alkylene group most preferably a linear alkylene group having 3 to 6 carbon atoms, particularly preferably a linear alkylene group having 3 to 5 carbon atoms.
- Examples of the monovalent aliphatic hydrocarbon group having 1 to 3 carbon atoms in R 5 and R 6 include a straight or branched chain having 1 to 3 carbon atoms such as a methyl group, an ethyl group, a propyl group, and an isopropyl group.
- hydroxyalkyl ether group in R 5 and R 6 examples include mono- or di (hydroxy) C 1-3 alkyl ether groups such as 2-hydroxyethoxy group, 2-hydroxypropoxy group, 2,3-dihydroxypropoxy group and the like. Is mentioned.
- R 5 and R 6 are the same or different, preferably a monovalent aliphatic hydrocarbon group having 1 to 3 carbon atoms, more preferably a linear or branched alkyl group having 1 to 3 carbon atoms. Group, particularly preferably a linear alkyl group having 1 to 3 carbon atoms, and particularly preferably a methyl group.
- the compounds represented by the formula (1) are particularly preferable in terms of excellent solubility of the fluid organic substance. Moreover, the said compound is preferable also at the point which can carry out thickening stabilization, maintaining the transparency, when the said fluid organic substance is transparent, in the fluid organic substance.
- the compound (2) of the present invention is represented by the following formula (2).
- the compound (2) is useful as a precursor for the compound (1).
- R 1 is a monovalent linear aliphatic hydrocarbon group having 10 to 25 carbon atoms
- R 2 and R 3 are the same or different, and are divalent divalent having 2, 4, 6, or 8 carbon atoms.
- R 4 represents an aliphatic hydrocarbon group, a bivalent alicyclic hydrocarbon group having 6 carbon atoms, or a divalent aromatic hydrocarbon group
- R 4 represents a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms.
- R 5, R 6 are the same or different, .L 1 ⁇ L 3 showing a monovalent aliphatic hydrocarbon group, or a hydroxyalkyl ether group having 1 to 3 carbon atoms represents an amide bond, and L 1 When L 3 is —CONH—, L 2 is —NHCO—, and when L 1 and L 3 are —NHCO—, L 2 is —CONH—)
- R 1 to R 6 and L 1 to L 3 are the same as above.
- the compound (2) includes a compound represented by the following formula (3) (hereinafter sometimes referred to as “compound (3)”) and a compound represented by the following formula (4) (hereinafter referred to as “compound (3)”). 4) ”or a compound represented by the following formula (3 ′) (hereinafter sometimes referred to as“ compound (3 ′) ”) and the following formula (4 ′): (Hereinafter, sometimes referred to as “compound (4 ′)”).
- R 1 is a monovalent linear aliphatic hydrocarbon group having 10 to 25 carbon atoms
- R 2 and R 3 are the same or different, and are divalent divalent having 2, 4, 6, or 8 carbon atoms.
- R 4 represents an aliphatic hydrocarbon group, a bivalent alicyclic hydrocarbon group having 6 carbon atoms, or a divalent aromatic hydrocarbon group, and R 4 represents a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms.
- R 5, R 6 are the same or different, .L 1 ⁇ L 3 showing a monovalent aliphatic hydrocarbon group, or a hydroxyalkyl ether group having 1 to 3 carbon atoms represents an amide bond, and L 1 When L 3 is —CONH—, L 2 is —NHCO—, and when L 1 and L 3 are —NHCO—, L 2 is —CONH— R 7 is a hydrogen atom or 1 carbon atom And in formula (3), OR 7 forms a ring by dehydration condensation or dealcoholization condensation with a hydrogen atom constituting L 2. May be)
- R 1 to R 6 and L 1 to L 2 are the same as above.
- Examples of the alkyl group having 1 to 3 carbon atoms for R 7 in the above formulas (3) and (4 ′) include a methyl group, an ethyl group, a propyl group, and an isopropyl group.
- the ring formed by dehydration condensation or dealcohol condensation of OR 7 in formula (3) with the hydrogen atom constituting L 2 includes, for example, pyrrolidine-2,5-dione ring, piperidine-2,6-dione A ring etc. are mentioned.
- the amount of the compound (4) used may be 1 mol or more with respect to 1 mol of the compound (3), and an excessive amount may be used.
- the amount of the compound (4 ′) used may be 1 mol or more with respect to 1 mol of the compound (3 ′), and an excess amount may be used.
- reaction of the compound (3) and the compound (4), or the compound (3 ') and the compound (4') can be carried out, for example, by stirring at a temperature of 100 to 120 ° C for 10 to 20 hours.
- the reaction atmosphere is not particularly limited as long as the reaction is not inhibited, and may be any of an air atmosphere, a nitrogen atmosphere, an argon atmosphere, and the like.
- the reaction can be carried out by any method such as batch, semi-batch and continuous methods.
- the obtained reaction product can be separated and purified by separation means such as filtration, concentration, distillation, extraction, crystallization, adsorption, recrystallization, column chromatography, etc., or a combination means combining these.
- the compound (1) can be produced by obtaining the compound (2) by the above method and oxidizing the obtained compound (2).
- hydrogen peroxide As the oxidizing agent used for the oxidation of the compound (2) obtained by the above method, for example, hydrogen peroxide can be used.
- hydrogen peroxide pure hydrogen peroxide may be used, but from the viewpoint of handleability, it is usually diluted with an appropriate solvent (for example, water) and used (for example, 5 to 70% by weight). Hydrogen oxide water).
- the amount of hydrogen peroxide to be used is, for example, about 0.1 to 10 mol with respect to 1 mol of compound (2).
- the oxidation reaction can be performed, for example, by stirring at a temperature of 30 to 70 ° C. for 3 to 20 hours.
- the oxidation reaction of the compound (2) is performed in the presence or absence of a solvent.
- a solvent include alcohol solvents such as methanol, ethanol, 2-propanol, and butanol; ethers such as diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, dioxane, dioxolane, 1,2-dimethoxyethane, and cyclopentyl methyl ether.
- ester solvents such as butyl acetate and ethyl acetate
- hydrocarbon solvents such as pentane, hexane, heptane and octane
- nitrile solvents such as acetonitrile and benzonitrile.
- the obtained reaction product can be separated and purified by separation means such as filtration, concentration, distillation, extraction, crystallization, adsorption, recrystallization, column chromatography, etc., or a combination means combining these.
- a compound represented by the following formula (3-1) can be produced by the following method.
- R 1 , R 2 , R 3 and R 7 are the same as above.
- two R 7 in R 7 and wherein in formula (3a) (3d), respectively may be the same or may be different.
- two COOR 7 in the formula may be subjected to dehydration condensation to form an acid anhydride.
- the compound represented, for example by a following formula (3'-1) can be manufactured with the following method.
- R 1 , R 2 , R 3 and R 7 are the same as above.
- Two R 7 in the formula (3b ′) may be the same or different.
- two COOR 7 in the formula may be dehydrated and condensed to form an acid anhydride.
- the step [1] is a step of obtaining a compound represented by the formula (3c) by reacting the compound represented by the formula (3a) with the compound represented by the formula (3b).
- the usage-amount of the compound represented by Formula (3b) should just be 1 mol or more with respect to 1 mol of compounds represented by Formula (3a), and can also use excess amount.
- the reaction temperature of this reaction is, for example, 80 to 150 ° C., and the reaction time is, for example, about 1 to 24 hours.
- the step [2] is a step of obtaining a compound represented by the formula (3-1) by reacting the compound represented by the formula (3c) with the compound represented by the formula (3d).
- the amount of the compound represented by the formula (3d) may be 1 mol or more, preferably 1 to 3 mol relative to 1 mol of the compound represented by the formula (3c).
- the reaction temperature of this reaction is, for example, 80 to 150 ° C., and the reaction time is, for example, about 0.5 to 10 hours. As this reaction proceeds, water is produced. Therefore, it is preferable to perform the reaction while removing water using a dehydrating agent (for example, acetic anhydride or the like) in order to promote the progress of the reaction.
- a dehydrating agent for example, acetic anhydride or the like
- the reaction [2] is preferably performed in the presence of a solvent.
- a solvent examples include pentafluorophenol, N, N-dimethylformamide, dimethylacetamide, o-dichlorobenzene, and the like. These can be used alone or in combination of two or more.
- reaction [2] can be carried out in the presence of a base such as triethylamine, pyridine, 4-dimethylaminopyridine, if necessary.
- a base such as triethylamine, pyridine, 4-dimethylaminopyridine, if necessary.
- the step [3] is a step of obtaining the compound represented by the formula (3c ′) by reacting the compound represented by the formula (3a ′) with the compound represented by the formula (3b ′).
- the reaction [3] can be carried out under conditions similar to those of the above reaction [2].
- the step [4] is a step of obtaining a compound represented by the formula (3′-1) by reacting a compound represented by the formula (3c ′) with a compound represented by the formula (3d ′). .
- the reaction [4] can be carried out under the same conditions as in the above reaction [1].
- the obtained reaction product is separated by a separation means such as filtration, concentration, distillation, extraction, crystallization, adsorption, recrystallization, column chromatography, or a combination means combining these. It can be purified.
- a separation means such as filtration, concentration, distillation, extraction, crystallization, adsorption, recrystallization, column chromatography, or a combination means combining these. It can be purified.
- the solvent composition for manufacturing an electronic device of the present invention is a composition containing a compatible material of the above compound (1) and a fluid organic substance, and the composition of the fluid organic substance is thickened by the compound (1). Is a uniformly stabilized composition.
- the fluid organic material as a raw material is an organic material having a viscosity [25 ° C., viscosity ( ⁇ ) at a shear rate of 1 s ⁇ 1 ] measured by a rheometer, for example, less than 0.5 Pa ⁇ s.
- fluid organic substances include hydrocarbon oils (for example, hexane, cyclohexane, isododecane, benzene, toluene, polyalphaolefin, liquid paraffin, etc.), ethers (for example, tetrahydrofuran, etc.), halogenated hydrocarbons.
- the above-mentioned solvent composition for producing an electronic device can be produced through a step of dissolving the compound (1) and a fluid organic substance. More specifically, the total amount of the fluid organic substance and the compound (1) can be mixed and heated to be compatible with each other and then cooled. In addition, the compound (1) is mixed with a part of the fluid organic substance, heated and compatible, and then cooled to produce a solvent composition for producing an electronic device. It can also be produced by mixing with a substance.
- the temperature at the time of compatibility is appropriately selected depending on the types of the compound (1) and the fluid organic substance, and is not particularly limited as long as the compound (1) and the fluid organic substance are compatible with each other. It is preferable that the temperature does not exceed 100 ° C. When the boiling point of the fluid organic substance is 100 ° C or less, the boiling point is preferable.
- the cooling after the compatibilization is not limited as long as it can be cooled to room temperature (for example, 25 ° C.) or lower, and may be gradually cooled at room temperature or rapidly by ice cooling or the like.
- the amount of the compound (1) used depends on the kind of the fluid organic substance, but for example, 0.1 to 100 parts by weight, preferably 0.5 to 80 parts by weight with respect to 1000 parts by weight of the fluid organic substance, Particularly preferred is 1 to 60 parts by weight, and most preferred is 1 to 30 parts by weight.
- the solvent composition for producing an electronic device of the present invention may contain other components within the range not impairing the effects of the present invention, in addition to the compound (1) and the fluid organic substance.
- the content of the compatible material (or the total amount of the compound (1) and the flowable organic substance) in the total amount of the solvent composition for producing an electronic device is, for example, 30% by weight or more, preferably 50% by weight or more, particularly preferably Is 60% by weight or more, most preferably 70% by weight or more, and particularly preferably 90% by weight or more.
- the upper limit is 100% by weight. That is, the solvent composition for manufacturing an electronic device of the present invention may contain only a compatible material of the compound (1) and a fluid organic substance without substantially containing other components. As other components, it can adjust suitably according to a use.
- the viscosity of the solvent composition for producing an electronic device of the present invention [viscosity ( ⁇ ) at 25 ° C., shear rate of 0.3 s ⁇ 1 ] by a rheometer is in the range of 10 Pa ⁇ s or more (for example, 10 to 100 Pa ⁇ s). It is preferable that the applied composition can be prevented from sagging or flowing, and the coating accuracy can be improved.
- the viscosity [ ⁇ at a shear rate of 0.1 s ⁇ 1 at 25 ° C. and a shear rate ( ⁇ )] of the solvent composition for producing an electronic device of the present invention is in the range of 10 Pa ⁇ s or more (for example, 10 to 100 Pa ⁇ s). It is preferable that the applied composition can be prevented from sagging or flowing, and the coating accuracy can be improved.
- the solvent composition for producing an electronic device of the present invention has shearing properties and has a viscosity ratio [viscosity at 25 ° C. by rheometer and shear rate of 1 s ⁇ 1 / viscosity at shear rate of 10 s ⁇ 1 by rheometer. ] Is for example more than 1.5, preferably 2 or more, particularly preferably 3 or more.
- the upper limit is, for example, 10, preferably 8. Therefore, the viscosity can be reduced at the time of application. For example, when applying using a printing machine or the like, the discharge property is excellent. In addition, by drastically increasing the viscosity after application, the applied composition can be prevented from sagging, and the application accuracy can be improved.
- the solvent composition for producing an electronic device of the present invention has an appropriate viscosity and shear thinning property as described above, a binder resin (for example, an ethyl cellulose resin, an alkyl cellulose resin, a polyvinyl acetal resin, an acrylic resin or the like having a molecular weight of 10,000 or more)
- a binder resin for example, an ethyl cellulose resin, an alkyl cellulose resin, a polyvinyl acetal resin, an acrylic resin or the like having a molecular weight of 10,000 or more
- the addition amount is, for example, 10% by weight or less, preferably 5% by weight or less of the total amount of the composition (100% by weight).
- the added amount of the binder resin exceeds the above range, the residual amount of ash derived from the binder resin generated by baking increases, and various problems caused by the residual ash (for example, deterioration of electrical characteristics when used in conductive ink) There is a tendency that it becomes difficult to suppress the occurrence of.
- the solvent composition for producing an electronic device of the present invention is excellent in thermal decomposability and easily has a low molecular weight. Therefore, the solvent composition for producing an electronic device of the present invention has a lower temperature (for example, 100 to 350 ° C., preferably 150 to 300 ° C., particularly preferably 150 to 300 ° C.) compared with a solvent composition to which a viscosity is imparted by a binder resin such as ethyl cellulose. 250 ° C.), and softening and deformation of the coated body in the baking process can be prevented.
- a lower temperature for example, 100 to 350 ° C., preferably 150 to 300 ° C., particularly preferably 150 to 300 ° C.
- a binder resin such as ethyl cellulose. 250 ° C.
- the solvent composition for producing an electronic device of the present invention has the above characteristics, for example, a capacitor, an inductor, a varistor, a thermistor, a speaker, an actuator, an antenna, a solid oxide fuel cell (SOFC), etc. (particularly, a multilayer ceramic capacitor)
- SOFC solid oxide fuel cell
- it is useful as a solvent for ink for manufacturing wiring and / or electrodes.
- it is particularly useful as an adhesive solvent in the production of electronic devices.
- Example 1 Provide of Compound (1-3)> Methyl docosanoate (20.0 g, 56.4 mmol) and ethylenediamine (16.9 g, 281 mmol) were stirred at 110 ° C. for 18 hours, and the reaction was washed with methanol and then filtered. The filtrate was evaporated, and the resulting residue was purified by recrystallization using hexane. N-docosanoylethylenediamine was obtained as white crystals (yield 65%, 14.0 g, 36.7 mmol).
- N-dimethylformamide 40 ml
- N-docosanoylethylenediamine 12.0 g, 31.4 mmol
- triethylamine 6.35 g, 62.8 mmol
- succinic anhydride 3.45 g, 34.5 mmol
- acetic anhydride 4.81 g, 47.1 mmol
- the reaction mixture was poured into water (200 ml) and the precipitate was filtered and washed with water.
- N-docosanoylaminoethylsuccinimide (4.00 g, 8.60 mmol) and N, N-dimethyl-1,3-propanediamine (2.63 g, 25.8 mmol) were stirred at 120 ° C. for 18 hours.
- the reaction mixture was poured into methanol and the precipitate was filtered and washed with methanol. The obtained solid was purified by recrystallization using acetone and methanol.
- Example 2 Provide of Compound (1-4)> N-docosanoylaminoethylsuccinimide was obtained in the same manner as in Example 1.
- N-docosanoylaminoethylsuccinimide (8.00 g, 17.2 mmol) and hexamethylenediamine (10.0 g, 86.1 mmol) were stirred at 120 ° C. for 18 hours.
- the reaction mixture was poured into methanol and the precipitate was filtered and washed with methanol.
- the obtained solid was purified by recrystallization using acetonitrile and methanol.
- N- (docosanoylaminoethyl) aminosuccinamoylaminohexylamine was obtained as a white crystalline powder (yield 69% 6.91 g, 11.9 mmol).
- N- (docosanoylaminoethyl) aminosuccinamoylaminohexylamine (3.25 g, 5.59 mmol)
- 37% aqueous formaldehyde (2.73 ml)
- formic acid (1.55 g, 33.7 mmol) were added to 2-propanol ( 15 ml) and stirred at 100 ° C. for 4 hours.
- the reaction mixture was poured into 1M aqueous sodium hydroxide solution (20 ml) and the crystals were filtered.
- Example 3 ⁇ Production of Compound (1-1)> Methyl eicosanoate (18.0 g, 55.1 mmol) and ethylenediamine (16.5 g, 276 mmol) were stirred at 110 ° C. for 18 hours, and the reaction was washed with methanol and filtered. The filtrate was evaporated, and the resulting residue was purified by recrystallization using hexane. N-eicosanoylethylenediamine was obtained as white crystals (yield 68%, 13.3 g, 37.5 mmol).
- N-eicosanoylaminoethylsuccinimide (4.00 g, 9.16 mmol) and N, N-dimethyl-1,3-propanediamine (2.81 g, 27.5 mmol) were stirred at 120 ° C. for 18 hours.
- the reaction mixture was poured into methanol and the precipitate was filtered and washed with methanol.
- the obtained solid was purified by recrystallization using acetone and methanol.
- the 1 H-NMR (CDCl 3 ) measurement result of the obtained compound is shown in FIG.
- N- (eicosanoylaminoethylaminosuccinamoylaminopropyl) -N, N-dimethylamine oxide represented by the following formula (1-1) was obtained as a white solid ( Yield 58%, 2.39 g, 4.30 mmol).
- the 1 H-NMR (CDCl 3 ) measurement result of the obtained compound is shown in FIG.
- Example 4 Provide of Compound (1-5)> A compound represented by the following formula (2-5) was obtained in the same manner as in Example 2 except that methyl octadecanoate was used instead of methyl docosanoate, and a compound represented by the following formula (1-5) was obtained. Obtained.
- Example 5 Provide of Compound (1-6)> A compound represented by the following formula (2-6) was obtained in the same manner as in Example 1 except that methyl octadecanoate was used instead of methyl docosanoate, and a compound represented by the following formula (1-6) was obtained. Obtained.
- Example 6 Provide of Compound (1-7)> A compound represented by the following formula (2-7) was obtained in the same manner as in Example 2 except that methyl palmitate was used instead of methyl docosinate, and a compound represented by the following formula (1-7) was obtained. Obtained.
- Example 7 Provide of Compound (1-8)> A compound represented by the following formula (2-8) was obtained in the same manner as in Example 1 except that methyl palmitate was used instead of methyl docosinate, and a compound represented by the following formula (1-8) was obtained. Obtained.
- Example 8 Provide of Compound (1-9)> A compound represented by the following formula (2-9) was obtained in the same manner as in Example 2 except that methyl myristate was used instead of methyl docosinate, and a compound represented by the following formula (1-9) was obtained. Obtained.
- ethyl cellulose (EC: trade name “Etocel STD200”, manufactured by Nisshin Kasei Co., Ltd.) is used as a thickening stabilizer, heated and dissolved at a liquid temperature of 80 ° C. for 24 hours, and cooled to 25 ° C. A solvent composition was obtained.
- the viscosity of the obtained solvent composition is a viscosity / viscoelasticity measuring device equipped with a cone plate sensor (60 mm diameter, cone angle 1 °, 35 mm diameter cone angles 1 °, 2 °, 4 °) and a Peltier temperature controller. (Rheometer) (trade name “Rheo Stress 600”, manufactured by HAAKE Corporation), and measuring the viscosity by changing the shear rate from 0.1 to 100 s ⁇ 1 in logarithmic steps under a constant flow viscosity measurement mode at 25 ° C. The thickening effect (shear thinning and thickening) was evaluated.
- the solvent composition of the present invention has an appropriate viscosity and shear thinning property and has a very low residual ash content.
- the solvent composition of the comparative example had a low viscosity, poor shearing properties, and a high ash residual rate.
- [1] A compound represented by formula (1).
- [2] The compound according to [1], wherein R 2 and R 3 in the formula (1) are the same or different and each is a divalent aliphatic hydrocarbon group having 2, 4, 6, or 8 carbon atoms.
- [3] The compound according to [1], wherein R 2 and R 3 in the formula (1) are the same or different and are a linear alkylene group having 2, 4, 6, or 8 carbon atoms.
- R 2 and R 3 in the formula (1) are the same or different and each is a divalent aliphatic hydrocarbon group having 2 or 4 carbon atoms.
- R 5 and R 6 in formula (1) are the same or different and are monovalent aliphatic hydrocarbon groups having 1 to 3 carbon atoms.
- a solvent composition comprising a compatible product of the compound according to any one of [1] to [17] and a fluid organic substance.
- the solvent composition according to [23] wherein the fluid organic substance has a viscosity of less than 0.5 Pa ⁇ s at 25 ° C. and a shear rate of 1 s ⁇ 1 by a rheometer.
- the fluid organic substance is at least one selected from hydrocarbon oils, ethers, halogenated hydrocarbons, petroleum components, animal and vegetable oils, silicone oils, esters, aromatic carboxylic acids, pyridines, and alcohols.
- the solvent composition according to any one of [23] to [26] which has a viscosity of 10 Pa ⁇ s or more at 25 ° C.
- the viscosity ratio [viscosity at 25 ° C. by rheometer and shear rate of 1 s ⁇ 1 / viscosity at shear rate of 10 s ⁇ 1 by rheometer] exceeds 1.5, [23] to [27]
- the solvent composition as described in any one of these.
- the content of at least one polymer compound selected from ethyl cellulose resin, alkyl cellulose resin, polyvinyl acetal resin, and acrylic resin is 10% by weight or less of the total amount of the solvent composition, [23] to [28 ] The solvent composition as described in any one of.
- An ink comprising the solvent composition according to any one of [23] to [33].
- [36] A conductive ink comprising the solvent composition according to any one of [23] to [33].
- the compound represented by the formula (1) of the present invention can be suitably used as a thickening stabilizer for paints, adhesives, inks, lubricating oils, pharmaceuticals, quasi drugs, cosmetics and the like.
- the solvent composition containing the compound represented by said Formula (1) has moderate viscosity and shearing property. Therefore, it does not easily drip and has good coating properties. Furthermore, it can be fired at a low temperature, and the residual amount of ash after firing can be significantly reduced. Therefore, the solvent composition is particularly useful as an ink solvent for producing an electronic device or a solvent for an adhesive for producing an electronic device.
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Abstract
Description
本発明の他の目的は、流動性有機物質を所望の粘度に増粘し、組成を均一に安定化することができる前記化合物の前駆体を提供することにある。
本発明の他の目的は、前記化合物と流動性有機物質との相溶物を含み、電子デバイス製造用に好適に使用される溶剤組成物を提供することにある。
本発明の更に他の目的は、前記溶剤組成物の製造方法を提供することにある。
で表される化合物を提供する。
で表される化合物を提供する。
で表される化合物を酸化して、下記式(1)
で表される化合物を得る、式(1)で表される化合物の製造方法を提供する。
で表される化合物と流動性有機物質とを相溶させる工程を経て、前記の電子デバイス製造用溶剤組成物を得る、電子デバイス製造用溶剤組成物の製造方法を提供する。
更に、エチルセルロースにより流動性有機物質を増粘して得られる溶剤組成物に比べて、本発明の電子デバイス製造用溶剤組成物は低温で焼成することができ、溶剤組成物が塗布された被塗布体が長時間高温に曝されることにより軟化、変形することを防止できる。その上、焼成後の灰分の残留量を著しく低減することができ、残留灰分により引き起こされていた種々の問題(例えば、導電性インクに使用した場合の電気特性の低下等)の発生を抑制することができる。
本発明の化合物(1)は、下記式(1)で表される。
本発明の化合物(2)は下記式(2)で表される。化合物(2)は上記化合物(1)の前駆体として有用である。
上記化合物(2)は、下記式(3)で表される化合物(以後、「化合物(3)」と称する場合がある)と、下記式(4)で表される化合物(以後、「化合物(4)」と称する場合がある)を反応させて、若しくは下記式(3’)で表される化合物(以後、「化合物(3’)」と称する場合がある)と、下記式(4’)で表される化合物(以後、「化合物(4’)」と称する場合がある)を反応させることで製造することができる。
本発明の電子デバイス製造用溶剤組成物は、上記化合物(1)と流動性有機物質との相溶物を含む組成物であり、上記化合物(1)によって流動性有機物質が増粘され、組成が均一に安定化された組成物である。
ドコサン酸メチル(20.0g、56.4mmol)およびエチレンジアミン(16.9g、281mmol)を110℃で18時間撹拌し、反応物をメタノールで洗浄後、濾過した。濾液を溶媒留去し、得られた残渣に対しヘキサンを用いて再結晶により精製した。N-ドコサノイルエチレンジアミンを白色結晶として得た(収率65%、14.0g、36.7mmol)。
実施例1と同様の方法でN-ドコサノイルアミノエチルスクシンイミドを得た。
エイコサン酸メチル(18.0g、55.1mmol)およびエチレンジアミン(16.5g、276mmol)を110℃で18時間撹拌し、反応物をメタノールで洗浄後、濾過した。濾液を溶媒留去し、得られた残渣に対しヘキサンを用いて再結晶により精製した。N-エイコサノイルエチレンジアミンを白色結晶として得た(収率68%、13.3g、37.5mmol)。
ドコサン酸メチルに代えてオクタデカン酸メチルを使用した以外は実施例2と同様にして、下記式(2-5)で表される化合物を得、下記式(1-5)で表される化合物を得た。
ドコサン酸メチルに代えてオクタデカン酸メチルを使用した以外は実施例1と同様にして、下記式(2-6)で表される化合物を得、下記式(1-6)で表される化合物を得た。
ドコサン酸メチルに代えてパルミチン酸メチルを使用した以外は実施例2と同様にして、下記式(2-7)で表される化合物を得、下記式(1-7)で表される化合物を得た。
ドコサン酸メチルに代えてパルミチン酸メチルを使用した以外は実施例1と同様にして、下記式(2-8)で表される化合物を得、下記式(1-8)で表される化合物を得た。
ドコサン酸メチルに代えてミリスチン酸メチルを使用した以外は実施例2と同様にして、下記式(2-9)で表される化合物を得、下記式(1-9)で表される化合物を得た。
表1に示す各種流動性有機物質(1,3-ブタンジオール(1,3-BG)、α-ターピネオール(TPO))を試験管に1cm3ずつはかりとり、ここに増粘安定剤として上記実施例1~8で得られた化合物をそれぞれ10mg加えて混合し、100℃で加熱撹拌して流動性有機物質と増粘安定剤を相溶させ、25℃まで冷却して溶剤組成物を得た。尚、比較例では増粘安定剤としてエチルセルロース(EC:商品名「エトセルSTD200」、日新化成(株)製)を使用し、液温80℃で24時間加熱溶解し、25℃まで冷却して溶剤組成物を得た。
得られた溶剤組成物の[ずり速度1s-1の時の粘度/ずり速度10s-1の時の粘度]から、下記基準に従ってシェアシニング性を評価した。
1: 1.5以下
2: 1.5を超え、3.0以下
3: 3.0を超え、4.5以下
4: 4.5超
得られた溶剤組成物のずり速度0.1s-1の時の粘度から、下記基準に従って増粘性を評価した。
1: 5Pa・s以下
2: 5Pa・sを超え、10Pa・s以下
3: 10Pa・sを超え、50Pa・s以下
4: 50Pa・s超え
TG-DTAを用い、溶剤組成物各20mgを20℃から400℃まで10℃/分で昇温し、250℃における残留灰分量を測定して、溶剤組成物全量に対する残留灰分量の割合(=灰分残存率)を算出した。
[1] 式(1)で表される化合物。
[2] 式(1)中のR2、R3は同一又は異なって、炭素数2、4、6、若しくは8の2価の脂肪族炭化水素基である、[1]に記載の化合物。
[3] 式(1)中のR2、R3は同一又は異なって、炭素数2、4、6、若しくは8の直鎖状アルキレン基である、[1]に記載の化合物。
[4] 式(1)中のR2、R3は同一又は異なって、炭素数2若しくは4の2価の脂肪族炭化水素基である、[1]に記載の化合物。
[5] 式(1)中のR2、R3は同一又は異なって、炭素数2若しくは4の直鎖状アルキレン基である、[1]に記載の化合物。
[6] 式(1)中のR2、R3は同一又は異なって、炭素数2の2価の脂肪族炭化水素基である、[1]に記載の化合物。
[7] 式(1)中のR2、R3は同一に、炭素数2の直鎖状アルキレン基である、[1]に記載の化合物。
[8] 式(1)中のR4は炭素数1~8の直鎖状又は分岐鎖状アルキレン基である、[1]~[7]の何れか1つに記載の化合物。
[9] 式(1)中のR4は炭素数1~7の直鎖状アルキレン基である、[1]~[7]の何れか1つに記載の化合物。
[10] 式(1)中のR4は炭素数3~7の直鎖状アルキレン基である、[1]~[7]の何れか1つに記載の化合物。
[11] 式(1)中のR4は炭素数3~6の直鎖状アルキレン基である、[1]~[7]の何れか1つに記載の化合物。
[12] 式(1)中のR4は炭素数3~5の直鎖状アルキレン基である、[1]~[7]の何れか1つに記載の化合物。
[13] 式(1)中のR5、R6は同一又は異なって、炭素数1~3の1価の脂肪族炭化水素基である、[1]~[12]の何れか1つに記載の化合物。
[14] 式(1)中のR5、R6は同一又は異なって、炭素数1~3の直鎖状又は分岐鎖状アルキル基である、[1]~[12]の何れか1つに記載の化合物。
[15] 式(1)中のR5、R6は同一又は異なって、炭素数1~3の直鎖状アルキル基である、[1]~[12]の何れか1つに記載の化合物。
[16] 式(1)中のR5、R6は同一にメチル基である、[1]~[12]の何れか1つに記載の化合物。
[17] 式(1-1)~(1-9)で表される化合物から選択される少なくとも1種の化合物である、[1]~[16]の何れか1つに記載の化合物。
[18] 下記式(2)で表される化合物。
[19] 式(2-1)~(2-9)で表される化合物から選択される少なくとも1種の化合物である、[18]に記載の化合物。
[20] 式(3)で表される化合物と、式(4)で表される化合物を反応させて、若しくは式(3’)で表される化合物と、式(4’)で表される化合物を反応させて、式(2)で表される化合物を得る、式(2)で表される化合物の製造方法。
[21] 式(2)で表される化合物を酸化して、式(1)で表される化合物を得る、式(1)で表される化合物の製造方法。
[22] 式(2)で表される化合物1molに対して、過酸化水素を0.1~10mol反応させて酸化する、[21]に記載の式(1)で表される化合物の製造方法。
[23] [1]~[17]の何れか1つに記載の化合物と流動性有機物質との相溶物を含む溶剤組成物。
[24] 流動性有機物質の、レオメーターによる、25℃、ずり速度1s-1における粘度が0.5Pa・s未満である、[23]に記載の溶剤組成物。
[25] 流動性有機物質が、炭化水素油、エーテル、ハロゲン化炭化水素、石油成分、動植物油、シリコーン油、エステル、芳香族カルボン酸、ピリジン、及びアルコールから選択される少なくとも1種である、[23]又は[24]に記載の溶剤組成物。
[26] レオメーターによる、25℃、ずり速度0.3s-1における粘度が10Pa・s以上である、[23]~[25]の何れか1つに記載の溶剤組成物。
[27] レオメーターによる、25℃、ずり速度0.1s-1における粘度が10Pa・s以上である、[23]~[26]の何れか1つに記載の溶剤組成物。
[28] 粘度比[レオメーターによる25℃、ずり速度1s-1の時の粘度/レオメーターによるずり速度10s-1の時の粘度]が1.5超である、[23]~[27]の何れか1つに記載の溶剤組成物。
[29] エチルセルロース樹脂、アルキルセルロース樹脂、ポリビニルアセタール樹脂、及びアクリル樹脂から選択される少なくとも種の高分子化合物の含有量が、溶剤組成物全量の10重量%以下である、[23]~[28]の何れか1つに記載の溶剤組成物。
[30] 高分子化合物が、分子量10000以上の高分子化合物である、[29]に記載の溶剤組成物。
[31] 分子量10000以上の高分子化合物の含有量が、溶剤組成物全量の10重量%以下である、[23]~[28]の何れか1つに記載の溶剤組成物。
[32] 電子デバイス製造用である、[23]~[31]の何れか1つに記載の溶剤組成物。
[33] 積層セラミックコンデンサ製造用である、[23]~[31]の何れか1つに記載の溶剤組成物。
[34] [23]~[33]の何れか1つに記載の溶剤組成物を含むインク。
[35] [23]~[33]の何れか1つに記載の溶剤組成物を含む電子デバイス製造用インク。
[36] [23]~[33]の何れか1つに記載の溶剤組成物を含む導電性インク。
[37] [34]~[36]の何れか1つに記載のインクを使用して電子デバイスの配線及び/又は電極を製造する工程を有する、電子デバイス製造方法。
[38] [23]~[33]の何れか1つに記載の溶剤組成物を含む、電子デバイス製造用接着剤。
[39] [38]に記載の接着剤を使用して電子デバイスを製造する、電子デバイス製造方法。
[40] [1]~[17]の何れか1つに記載の化合物と流動性有機物質とを相溶させる工程を経て溶剤組成物を得る、溶剤組成物の製造方法。
[41] 流動性有機物質1000重量部に対して、[1]~[17]の何れか1つに記載の化合物を0.1~100重量部の割合で相溶させる、[40]に記載の溶剤組成物の製造方法。
[42] 式(1)で表される化合物と流動性有機物質とを相溶させる工程を経て、[23]~[33]の何れか1つに記載の溶剤組成物を得る、溶剤組成物の製造方法。
また、前記式(1)で表される化合物を含む溶剤組成物は、適度な粘度とシェアシニング性とを有する。そのため、液ダレしにくく、良好な塗布性を有する。更に、低温で焼成することができ、焼成後の灰分の残留量を著しく低減することができる。そのため、前記溶剤組成物は、電子デバイスを製造するためのインクの溶剤、或いは電子デバイス製造用接着剤の溶剤として特に有用である。
Claims (7)
- 下記式(3)で表される化合物と、下記式(4)で表される化合物を反応させて、若しくは下記式(3’)で表される化合物と、下記式(4’)で表される化合物を反応させて、下記式(2)で表される化合物を得る、式(2)で表される化合物の製造方法。
- 下記式(2)
で表される化合物を酸化して、下記式(1)
で表される化合物を得る、式(1)で表される化合物の製造方法。 - 請求項1に記載の化合物と流動性有機物質との相溶物を含む、電子デバイス製造用溶剤組成物。
- 流動性有機物質が、炭化水素油、エーテル、ハロゲン化炭化水素、石油成分、動植物油、シリコーン油、エステル、芳香族カルボン酸、ピリジン、及びアルコールから選択される少なくとも1種である、請求項5に記載の電子デバイス製造用溶剤組成物。
- 下記式(1)
で表される化合物と流動性有機物質とを相溶させる工程を経て、請求項5又は6に記載の電子デバイス製造用溶剤組成物を得る、電子デバイス製造用溶剤組成物の製造方法。
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US20210017124A1 (en) | 2021-01-21 |
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