WO2022080409A1 - エステル化合物、エステル化合物の合成方法、及び樹脂組成物 - Google Patents

エステル化合物、エステル化合物の合成方法、及び樹脂組成物 Download PDF

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Publication number
WO2022080409A1
WO2022080409A1 PCT/JP2021/037891 JP2021037891W WO2022080409A1 WO 2022080409 A1 WO2022080409 A1 WO 2022080409A1 JP 2021037891 W JP2021037891 W JP 2021037891W WO 2022080409 A1 WO2022080409 A1 WO 2022080409A1
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Prior art keywords
ester compound
polyol
resin composition
ester
disulfide bond
Prior art date
Application number
PCT/JP2021/037891
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English (en)
French (fr)
Japanese (ja)
Inventor
圭市 坂本
祐樹 宮本
哲也 今井
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昭和電工マテリアルズ株式会社
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Priority to JP2022557044A priority Critical patent/JPWO2022080409A1/ja
Publication of WO2022080409A1 publication Critical patent/WO2022080409A1/ja

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B61/00—Other general methods
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/22—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/52—Polythioethers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C08G65/48—Polymers modified by chemical after-treatment

Definitions

  • the present disclosure relates to an ester compound, a method for synthesizing an ester compound, and a resin composition.
  • Patent Document 1 discloses an image forming apparatus including a recording member having a photosoftening resin layer made of a photosoftening resin.
  • One aspect of the present disclosure relates to an ester compound which is a transesterification reaction product of a dicarboxylic acid ester having a disulfide bond and a polyol, having a disulfide bond in the molecular chain and having a hydroxy group at the terminal.
  • an ester compound having a disulfide bond in the molecular chain and having a hydroxy group at the terminal is obtained by a transesterification reaction between a disulfide acid ester having a disulfide bond and a polyol.
  • a transesterification reaction between a disulfide acid ester having a disulfide bond and a polyol.
  • Another aspect of the present disclosure relates to a resin composition containing the above ester compound and a photoradical generator.
  • a novel ester compound having photosoftness a method for synthesizing the ester compound, and a resin composition softened by light irradiation are provided.
  • photosoftness means that the viscosity is lowered, the elastic modulus is lowered, the loss tangent (tan ⁇ ) is increased, the hardness is lowered, and the like by light irradiation.
  • process is included in this term not only as an independent process but also as long as the intended action of the process is achieved even if it cannot be clearly distinguished from other processes. Is done.
  • the numerical range indicated by using "-” indicates a range including the numerical values before and after "-" as the minimum value and the maximum value, respectively.
  • the upper limit value or the lower limit value of the numerical range of one step may be replaced with the upper limit value or the lower limit value of the numerical range of another step.
  • the upper limit value or the lower limit value of the numerical range may be replaced with the value shown in the examples.
  • the upper limit value and the lower limit value described individually can be arbitrarily combined.
  • each component in the composition is the total amount of the plurality of substances present in the composition when a plurality of substances corresponding to each component are present in the composition, unless otherwise specified.
  • the exemplary materials may be used alone or in combination of two or more unless otherwise specified.
  • a or B may include either A or B, and may include both.
  • the ester compound according to the present embodiment is a transesterification product of a dicarboxylic acid ester having a disulfide bond and a polyol, and is a photosoftening resin having a disulfide bond in the molecular chain and a hydroxy group at the terminal. ..
  • Such an ester compound can be obtained by transesterifying a dicarboxylic acid ester having a disulfide bond with a polyol.
  • the ester compound according to the present embodiment is different from the compound having at least a hydroxy group and a disulfide bond by the Michael addition reaction in that it does not have a thioether bond. Further, in the transesterification reaction, the molecular weight can be easily controlled as compared with the Michael addition reaction, and the desired ester compound can be stably obtained.
  • the hydroxyl value of the ester compound may be 20 to 150 mgKOH / g, 20 to 140 mgKOH / g, or 25 to 120 mgKOH / g.
  • the hydroxyl value can be measured according to JIS K0070.
  • the dicarboxylic acid ester having a disulfide bond is a compound having a disulfide bond capable of generating a thiyl radical by light irradiation and an alkyl ester group capable of transesterification reaction.
  • a compound having a structure represented by the following formula (1) can be used as the dicarboxylic acid ester having a disulfide bond.
  • R 1 and R 2 independently represent an alkyl group having 1 to 4 carbon atoms
  • R 3 and R 4 independently represent an alkylene group having 1 to 10 carbon atoms, respectively.
  • R 1 and R 2 are preferably an alkyl group having 1 to 3 carbon atoms, more preferably a methyl group or an ethyl group, and further preferably a methyl group, from the viewpoint that the transesterification reaction can easily proceed.
  • R 3 and R 4 may be an alkylene group having 1 to 8 carbon atoms, an alkylene group having 2 to 6 carbon atoms, or an alkylene group having 2 to 4 carbon atoms.
  • dicarboxylic acid ester having a disulfide bond examples include dimethyl 3,3'-dithiopropionate, dimethyl dithiodiacetate, and dimethyl 4,4'-dithiodibutyrate.
  • the dicarboxylic acid ester according to the present embodiment may contain at least one selected from the group consisting of dimethyl 3,3'-dithiopropionic acid, dimethyl dithiodiacetate, and dimethyl 4,4'-dithiodibutyrate.
  • the polyol can be used without particular limitation as long as it is a compound having two or more hydroxy groups.
  • the polyol may be a compound (diol) having two hydroxy groups.
  • examples of the polyol include a polyether polyol, a polyester polyol, a polycaprolactone polyol, a polycarbonate polyol, a polybutadiene polyol, and a bisphenol A / ethylene oxide-added diol.
  • the polyol according to the present embodiment may contain at least one selected from the group consisting of a polyether polyol, a polyester polyol, a polycaprolactone polyol, a polycarbonate polyol, a polybutadiene polyol, and a bisphenol A / ethylene oxide-added diol.
  • polyether polyol examples include polytetramethylene ether glycol, polyethylene glycol, and polypropylene glycol.
  • an ester compound having a disulfide bond in the molecular chain and a hydroxy group at the terminal is obtained by a transesterification reaction between a disulfide acid ester having a disulfide bond and a polyol. Can be done.
  • the mixing ratio of the dicarboxylic acid ester and the polyol when synthesizing the ester compound is such that the molar ratio of the alkyl ester group of the dicarboxylic acid ester is 0.5 to 0.9 with respect to 1 mol of the hydroxy group of the polyol. It is preferable to adjust in the range of mol. This makes it easier to obtain an ester compound having a hydroxy group at the end, and makes it easier to adjust the ratio and molecular weight of the disulfide bond of the ester compound.
  • a catalyst When synthesizing an ester compound, a catalyst may be used to promote the transesterification reaction.
  • the catalyst is not particularly limited as long as it is a compound generally used for the transesterification reaction.
  • the catalyst include catalysts such as titanium compounds and acetate compounds.
  • titanium compounds include titanium tetraisopropoxide.
  • the temperature and time of the transesterification reaction are not particularly limited, the temperature may be about 25 to 120 ° C., and the time of the transesterification reaction may be about 1 to 20 hours.
  • the resin composition according to the present embodiment contains the above-mentioned ester compound and a photoradical generator.
  • the photoradical generator may be a component that reacts with the chile radical generated or a component that generates a photoinduced radical when the resin composition is irradiated with light.
  • a photoradical polymerization initiator or the like can be used as the photoradical generator.
  • Examples of the photoradical generator include an intramolecular cleavage type photoradical polymerization initiator and a hydrogen abstraction type photoradical polymerization initiator.
  • Examples of the intramolecular cleavage type photoradical polymerization initiator include a benzyl ketal-based photoradical polymerization initiator; an ⁇ -hydroxyacetophenone-based photoradical polymerization initiator; a benzoin-based photoradical polymerization initiator; an aminoacetophenone-based photoradical polymerization initiator.
  • Oxymuketone-based photoradical polymerization initiators include a benzophenone-based photoradical polymerization initiator, a thioxanthone-based photoradical polymerization initiator, and an anthraquinone-based photoradical polymerization initiator.
  • the content of the photoradical generator may be 1 part by mass or more, 5 parts by mass or more, or 8 parts by mass or more, and 25 parts by mass or less, 20 parts by mass or less, or 15 parts by mass with respect to 100 parts by mass of the ester compound. It may be less than or equal to a mass part.
  • the resin composition according to this embodiment may further contain polyisocyanate.
  • the polyisocyanate can be used without particular limitation as long as it is a compound having two or more isocyanate groups.
  • the polyisocyanate may be a compound having two isocyanate groups (diisocyanate).
  • polyisocyanate examples include aromatic isocyanates such as diphenylmethane diisocyanate (4,4'-diphenylmethane diisocyanate), dimethyldiphenylmethane diisocyanate, tolylene diisocyanate, xylylene diisocyanate, and p-phenylenedi isocyanate; and dicyclohexylmethane diisocyanate and isophorone diisocyanate.
  • aromatic isocyanates such as diphenylmethane diisocyanate (4,4'-diphenylmethane diisocyanate), dimethyldiphenylmethane diisocyanate, tolylene diisocyanate, xylylene diisocyanate, and p-phenylenedi isocyanate
  • dicyclohexylmethane diisocyanate and isophorone diisocyanate examples include aromatic isocyanates such as diphenylmethane diisocyan
  • Alicyclic isocyanates aliphatic isocyanates such as hexamethylene diisocyanates; derivatives such as isocyanurates, biurets, allophanates, uretdiones, and polymerics derived from these isocyanates, and polynuclear bodies can be mentioned.
  • polyisocyanate one type may be used alone, or two or more types may be used in combination.
  • the content of the polyisocyanate may be 10 parts by mass or more, 15 parts by mass or more, or 20 parts by mass or more, and 50 parts by mass or less, 40 parts by mass or less, or 30 parts by mass with respect to 100 parts by mass of the ester compound. It may be as follows.
  • the resin composition may further contain other components other than the above-mentioned components.
  • Other components include, for example, thermosetting resins such as epoxy resins, adhesion improvers such as coupling agents, polymerization inhibitors, light stabilizers, defoamers, fillers, chain transfer agents, thixotropy-imparting agents, and difficult.
  • additives such as fueling agents, mold release agents, surfactants, lubricants, and antistatic agents.
  • known ones can be used.
  • the total content of the other components may be 0 to 95% by mass, 0.01 to 50% by mass, or 0.1 to 10% by mass based on the total amount of the resin composition.
  • the resin composition may be used as a varnish of the resin composition diluted with a solvent.
  • the solvent include aromatic hydrocarbons such as toluene, xylene, mesityrene, cumene, and p-simene; aliphatic hydrocarbons such as hexane and heptane; cyclic alkanes such as methylcyclohexane; tetrahydrofuran, 1,4-dioxane and the like.
  • Cyclic ethers such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone; esters such as methyl acetate, ethyl acetate, butyl acetate, methyl lactate, ethyl lactate, ⁇ -butyrolactone; Carbonated esters such as ethylene carbonate and propylene carbonate; amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methyl-2-pyrrolidone (NMP) can be mentioned.
  • the solvent one type may be used alone or two or more types may be used in combination.
  • the concentration of solid components in the varnish may be 10 to 80% by mass based on the total mass of the varnish.
  • the resin composition can be prepared, for example, by mixing or kneading an ester compound, a photoradical generator, and components added as needed. Mixing and kneading can be performed by appropriately combining a disperser such as a normal stirrer, a raft machine, a triple roll, a ball mill, and a bead mill.
  • a disperser such as a normal stirrer, a raft machine, a triple roll, a ball mill, and a bead mill.
  • the resin composition according to this embodiment can be formed into a film and used as a photosoftening resin film. Further, it can be formed into a block shape and used as a photosoftening resin block.
  • the method for forming the resin composition in the form of a film or a block is not particularly limited, and a known method can be applied.
  • the resin composition according to the present embodiment has a property that the disulfide bond (—S—S—) in the ester compound is cleaved by light irradiation, and the compound having the disulfide bond is reduced in molecular weight and softened.
  • the resin composition can also be softened to a liquid (liquid). Further, the resin composition has a property of being easily formed into a film shape or a block shape. By utilizing such properties, the resin composition according to the present embodiment can be applied to, for example, the use of a photoresist agent for photolithography, and is used as a photosensitive resin composition or a photosensitive resin film. be able to.
  • the photosensitive resin composition or the photosensitive resin film can be patterned by light irradiation (exposure), and can be further developed by washing with water after light irradiation (exposure).
  • the resin composition according to this embodiment can be suitably used for forming a pattern film.
  • the resin composition according to the present embodiment is also, for example, a softening agent or an easy peeling agent for a strong adhesive tape; a pressure-sensitive agent for a slightly adhesive or non-adhesive film; a coating material, a pressure-sensitive adhesive, or a partial softening agent for an adhesive; Partial softener of molding material; Ultra-low elastic film that can be punched by irradiating with light after punching; Moisture proofing agent; Capsule film that softens and dissolves by irradiating light; Thickener that reduces viscosity by irradiating light, etc. It can be applied to various uses.
  • a softened product of the resin composition By irradiating the resin composition according to the embodiment with light, a softened product of the resin composition can be obtained.
  • the light in the light irradiation is not particularly limited, but may be, for example, ultraviolet light or visible light.
  • the wavelength of light in light irradiation may be 150 to 830 nm.
  • the light irradiation can be performed using, for example, a light irradiation device under the condition that the irradiation amount is 100 mJ / cm 2 or more.
  • the irradiation amount means the product of the illuminance and the irradiation time (seconds).
  • Examples of the light source for irradiating ultraviolet light or visible light include a low-pressure mercury lamp, a medium-pressure mercury lamp, a high-pressure mercury lamp, a metal halide lamp, and an LED lamp.
  • the light irradiation may be performed directly on the photosoftening resin composition, or may be performed via glass or the like.
  • the light irradiation of the resin composition may be performed while heating.
  • the heating conditions may be, for example, 40 to 200 ° C.
  • Example 1 A flask equipped with a stirrer, a thermometer, a reflux condenser, decompression equipment, and a nitrogen inflow pipe was prepared. 800 parts by mass of polyethylene glycol (manufactured by Sanyo Chemical Industries, Ltd., trade name "PEG-400", molecular weight 400) and 238 parts by mass of dimethyl 3,3'-dithiodipropionate (manufactured by Fujifilm Waco Chemical Co., Ltd.) in a flask. The mixture was charged, bubbling with nitrogen inflow into the liquid phase, and stirred at 90 ° C. for 2 hours while reducing the pressure to 70 kPa.
  • polyethylene glycol manufactured by Sanyo Chemical Industries, Ltd., trade name "PEG-400", molecular weight 400
  • dimethyl 3,3'-dithiodipropionate manufactured by Fujifilm Waco Chemical Co., Ltd.
  • Example 2 2000 parts by mass of polyethylene glycol (manufactured by Sanyo Chemical Industries, Ltd., trade name "PEG-2000", molecular weight 2000) and 119 parts by mass of dimethyl 3,3'-dithiodipropionate are placed in the same flask as in Example 1 and liquid. The phase was bubbled by influx of nitrogen, and the mixture was stirred at 90 ° C. for 2 hours while reducing the pressure to 70 kPa. Next, 22 parts by mass of titanium tetraisopropoxide (manufactured by Wako Pure Chemical Industries, Ltd.) was added, and the transesterification reaction was carried out by stirring at 100 ° C. for 12 hours with the bubbling and depressurization unchanged. As a result, an ester compound B having a hydroxy group and a disulfide bond (hydroxyl value: 27 mgKOH / g) was obtained.
  • Example 4 A resin composition was prepared by mixing 100 parts by mass of ester compound B and 10 parts by mass of Omnirad TPO.
  • Example 5 After mixing 100 parts by mass of ester compound A, 25 parts by mass of diphenylmethane diisocyanate (manufactured by Tosoh Corporation, trade name "Millionate MT”), and 13 parts by mass of Omnirad TPO, it is cured at 80 ° C. for 24 hours to form a resin composition. I made a thing.
  • a resin composition was prepared by mixing 100 parts by mass of polyethylene glycol (manufactured by Sanyo Chemical Industries, Ltd., trade name "PEG-2000", molecular weight 2000) with 10 parts by mass of Omnirad TPO.
  • the resin composition was irradiated with light using a high-pressure mercury lamp at an illuminance of 100 mW and an integrated light amount of 2000 mJ / cm 2 .
  • the viscosity of the resin composition before and after light irradiation was measured at 25 ° C. or 60 ° C. using an E-type viscometer (TV-22, manufactured by Toki Sangyo Co., Ltd.). The results are shown in Table 1.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Polyesters Or Polycarbonates (AREA)
PCT/JP2021/037891 2020-10-14 2021-10-13 エステル化合物、エステル化合物の合成方法、及び樹脂組成物 WO2022080409A1 (ja)

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Publication number Priority date Publication date Assignee Title
WO2024080256A1 (ja) * 2022-10-11 2024-04-18 株式会社レゾナック 半導体装置の製造方法
WO2024185554A1 (ja) 2023-03-03 2024-09-12 東洋紡株式会社 ジスルフィド結合を有する架橋ポリエステル樹脂
WO2024204615A1 (ja) * 2023-03-31 2024-10-03 株式会社レゾナック 半導体装置の製造方法
WO2024204619A1 (ja) * 2023-03-31 2024-10-03 株式会社レゾナック 半導体装置の製造方法

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US3459787A (en) * 1965-10-11 1969-08-05 Research Corp Sulphur containing polyesters
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JP6891546B2 (ja) * 2017-03-07 2021-06-18 東洋インキＳｃホールディングス株式会社 感光性オリゴマー、その製造方法及び該感光性オリゴマーを用いたカラーフィルタ用感光性着色組成物
JP7267812B2 (ja) * 2019-03-29 2023-05-02 太陽ホールディングス株式会社 感光性樹脂組成物、ドライフィルム、硬化物、および電子部品

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024080256A1 (ja) * 2022-10-11 2024-04-18 株式会社レゾナック 半導体装置の製造方法
WO2024185554A1 (ja) 2023-03-03 2024-09-12 東洋紡株式会社 ジスルフィド結合を有する架橋ポリエステル樹脂
WO2024204615A1 (ja) * 2023-03-31 2024-10-03 株式会社レゾナック 半導体装置の製造方法
WO2024204619A1 (ja) * 2023-03-31 2024-10-03 株式会社レゾナック 半導体装置の製造方法

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