WO2024122605A1 - 組成物、硬化性組成物、硬化体、光学物品、レンズ、眼鏡、抗菌・抗ウイルス剤、及び樹脂組成物 - Google Patents

組成物、硬化性組成物、硬化体、光学物品、レンズ、眼鏡、抗菌・抗ウイルス剤、及び樹脂組成物 Download PDF

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WO2024122605A1
WO2024122605A1 PCT/JP2023/043787 JP2023043787W WO2024122605A1 WO 2024122605 A1 WO2024122605 A1 WO 2024122605A1 JP 2023043787 W JP2023043787 W JP 2023043787W WO 2024122605 A1 WO2024122605 A1 WO 2024122605A1
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Prior art keywords
compound
bismuth
group
mass
organic compound
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English (en)
French (fr)
Japanese (ja)
Inventor
剛美 川崎
颯人 丸本
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Tokuyama Corp
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Tokuyama Corp
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Priority to JP2024562987A priority Critical patent/JPWO2024122605A1/ja
Priority to CN202380083279.1A priority patent/CN120435519A/zh
Priority to EP23900717.2A priority patent/EP4632004A1/en
Publication of WO2024122605A1 publication Critical patent/WO2024122605A1/ja
Anticipated expiration legal-status Critical
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    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G02B1/041—Lenses
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
    • C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0091—Complexes with metal-heteroatom-bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L43/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium or a metal; Compositions of derivatives of such polymers
    • C08L43/02—Homopolymers or copolymers of monomers containing phosphorus

Definitions

  • the present invention relates to a composition, a curable composition, a cured product, an optical article, a lens, glasses, an antibacterial/antiviral agent, and a resin composition.
  • lead glass and acrylic lead which is a lightweight material, are used as shielding materials to protect the eyes.
  • lead is harmful to the environment and the human body, and there is a strong demand for lead-free alternatives to shielding materials based on inorganic glass or resin.
  • Lead alternatives include bismuth, barium, antimony, tin, and tungsten, among which materials using bismuth are being investigated. Bismuth has long been used as a gastrointestinal medicine and is harmless to the human body, yet has the same radiation shielding ability as lead, making it a suitable element to replace lead.
  • This cured product has a high concentration of bismuth components dispersed in a resin matrix, and has excellent shielding capabilities not only for X-rays used in medical applications, but also for radiation such as beta rays, and can be used for radiation protection eyeglass lenses, shielding materials, screens, peepholes, etc.
  • bismuth compounds are known to have antibacterial and antiviral properties, and can be used as structural or coating materials with antibacterial and antiviral properties. Transparency is not necessarily required for this application.
  • the present invention aims to provide a composition and curable composition with reduced odor, a cured product of the curable composition, an optical article, a lens, a pair of glasses, an antibacterial agent, an antiviral agent, and a resin composition, all of which contain the cured product.
  • a ratio M1/M2 of a mass M1 of the first bismuth compound to a mass M2 of the coordinating organic compound is 4 or more and 4,990 or less.
  • the coordinating organic compound includes a compound having at least one heteroatom selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom, and an unsaturated bond.
  • ⁇ 6> The composition according to any one of ⁇ 1> to ⁇ 5>, wherein the coordinating organic compound contains an unsaturated dicarboxylic acid.
  • ⁇ 7> The composition according to any one of ⁇ 1> to ⁇ 6>, wherein the coordinating organic compound includes an unsaturated carboxylic acid ester.
  • ⁇ 8> The composition according to any one of ⁇ 1> to ⁇ 7>, wherein the coordinating organic compound includes an unsaturated carboxylic acid anhydride.
  • the first bismuth compound has high solubility in radically polymerizable compounds having at least one radically polymerizable group selected from the group consisting of a nitrile group, an acryloyl group, a methacryloyl group, a vinyl group, and an allyl group. Therefore, by using the first bismuth compound, a hardenable composition containing a high concentration of bismuth and a hardened product thereof can be obtained.
  • the first bismuth compound has better solubility in radically polymerizable compounds than bismuth subsalicylate alone.
  • the first phosphate ester is represented, for example, by the following formula (2).
  • Q1 is a hydrogen atom or a methyl group, and Q1 is preferably a methyl group.
  • Q2 is a hydrogen atom, a linear or branched alkyl group having 1 to 10 carbon atoms, an aryl group having 4 to 16 carbon atoms, or a (meth)acryloyloxyalkylene group.
  • the number of carbon atoms in the alkyl group is preferably 1 to 6.
  • the number of carbon atoms in the aryl group is preferably 5 to 8.
  • the aryl group is preferably a phenyl group.
  • the number of carbon atoms in the alkylene group contained in the (meth)acryloyloxyalkylene group is, for example, 1 to 10, preferably 1 to 3.
  • the (meth)acryloyloxyalkylene group is preferably a (meth)acryloyloxyethylene group.
  • the first bismuth compound may further be bonded to other compounds in addition to the first phosphate ester.
  • the bond between the bismuth and the other compounds may be any of ionic bonds, coordinate bonds, and covalent bonds. That is, the first bismuth compound may be a phosphate or complex salt having bismuth (Bi 3+ or Bi 5+ ) as the cation and the first phosphate ester and the other compounds as the anions, a phosphate compound, or a complex.
  • the ratio of the primary phosphate ester to the other compounds is preferably 0.1 to 10 moles, more preferably 0.1 to 5 moles, even more preferably 0.1 to 1 mole, and particularly preferably 0.1 to 0.5 moles, of the other compounds per mole of the primary phosphate ester. Note that when two or more types of primary phosphate esters are present, the above range is based on the total number of moles of the primary phosphate esters.
  • the IR spectrum is measured, for example, using a PerkinElmer Spectrum One, using the single reflection ATR method and four-times accumulation.
  • the 1 H- and 31 P-NMR measurements are performed using a nuclear magnetic resonance apparatus (JNM-ECA400II, manufactured by JEOL Ltd.) with deuterated acetone as the solvent and a sample concentration of 1% by mass.
  • JNM-ECA400II manufactured by JEOL Ltd.
  • an X-ray photoelectron spectrometer (ULVAC-PHI, Inc., ESCA5701ci/MC) is used, and the X-ray source is monochromatic Al-K ⁇ (14 kV-330 W), with an aperture diameter of ⁇ 800 ⁇ m and a photoelectron take-off angle of 45 degrees.
  • the sample is crushed in an agate mortar, and the resulting powder is fixed to a substrate with carbon tape and introduced into the measurement chamber for measurement.
  • the first bismuth compound is, for example, a phosphate or complex salt represented by the following formula (1):
  • X is (meth)acrylic acid represented by the following formula (1a), or salicylic acid represented by the following formula (1b).
  • R is a hydrogen atom or a methyl group.
  • X is preferably salicylic acid represented by the following formula (1b).
  • the fact that the first bismuth compound has the structure represented by the above formula (1) can be confirmed, for example, by detection of a proton-added molecular ion or a sodium-added ion of the compound in MALDI-TOF-MS measurement.
  • Suitable first bismuth compounds include those represented by the following formulas (III) to (V).
  • each R is independently a hydrogen atom or a methyl group.
  • x represents the number of moles of 2-((meth)acryloyloxy)ethyl hydrogen phosphate residues.
  • y represents the number of moles of phenyl-2-((meth)acryloyloxy)ethyl phosphate residues.
  • z represents the number of moles of bis[2-((meth)acryloxyoxy)ethyl]phosphate residues.
  • a represents the number of moles of (meth)acrylic acid residues.
  • q represents the number of moles of 2-((meth)acryloyloxy)ethyl hydrogen phosphate residues.
  • r represents the number of moles of phenyl-2-((meth)acryloyloxy)ethyl phosphate residues.
  • s represents the number of moles of 2-((meth)acryloyloxy)ethyl phosphate residues.
  • t represents the number of moles of bis[2-((meth)acryloyloxy)ethyl]phosphate residues.
  • c represents the number of moles of salicylic acid residues.
  • the first bismuth compound is, for example, a phosphate or complex salt represented by the following formula (3):
  • a4 is a number greater than 0 and equal to or less than 3.
  • a5 is a number greater than 0 and equal to or less than 3.
  • a4 + a5 is 3.
  • the first bismuth compound may also be a composition containing a compound other than the first bismuth compound.
  • this composition is also referred to as the first bismuth composition.
  • the first bismuth composition may contain a phosphate compound that is a by-product during production, or unreacted raw materials.
  • Examples of by-product phosphoric acid compounds include dimers of phosphoric acid esters (phosphoric acid monoesters) having one (meth)acryloyl group, dimers of phosphoric acid esters (phosphoric acid diesters) having two (meth)acryloyl groups, and esters of bismuth salicylate or bismuth (meth)acrylate with phosphoric acid.
  • unreacted raw materials include phosphate esters having one (meth)acryloyl group (phosphate monoesters), phosphate esters having two (meth)acryloyl groups (phosphate diesters), bismuth salicylate, bismuth (meth)acrylate, etc.
  • the first bismuth composition may also contain a compound derived from bismuth oxide.
  • the compound derived from bismuth oxide is, for example, a compound in which bismuth oxide is bonded to a phosphate ester having a (meth)acryloyl group, (meth)acrylic acid, and/or salicylic acid.
  • a hydroxyl group formed on the surface of the bismuth oxide is bonded to a carboxyl group of the phosphate ester, (meth)acrylic acid, or salicylic acid. It is very difficult to separate this compound derived from bismuth oxide from the first bismuth compound.
  • the method for producing the first bismuth compound is not particularly limited, but it is preferable to produce the first bismuth compound by reacting the second bismuth compound with a first phosphate ester. Specifically, it is preferable to produce the first bismuth compound by reacting the second bismuth compound with a first phosphate ester in an aliphatic hydrocarbon solvent or an aromatic solvent, optionally adding a polymerization inhibitor, and then dehydrating the resulting mixture.
  • Bismuth subsalicylate is a compound in which salicylic acid is bonded to bismuth, and is represented by the following formula (VI).
  • phosphate esters having two (meth)acryloyl groups include bis[2-(methacryloxyoxy)ethyl] hydrogen phosphate and phenyl[2-(methacryloxyoxy)ethyl] hydrogen phosphate.
  • the amount of the phosphate triester used is preferably 0.1 to 20 moles, and more preferably 0.2 to 5 moles, per mole of the total of the phosphate ester having one (meth)acryloyl group and the phosphate ester having two (meth)acryloyl groups.
  • the amount of the aliphatic hydrocarbon solvent or aromatic solvent used is not particularly limited, so long as it is an amount that allows sufficient mixing of the bismuth dibasic compound and the first phosphate ester. Considering the productivity of the first bismuth compound, it is preferable to use 5 to 100 mL of the aliphatic hydrocarbon solvent or aromatic solvent per 1 g of the bismuth dibasic compound.
  • the second bismuth compound may not dissolve, but in that case, it is preferable to crush the lumps of the second bismuth compound by an ultrasonic device or the like so that no lumps or the like of the second bismuth compound are present.
  • the primary phosphate is added to the cloudy solution in which the bismuth(II) compound is dispersed, and stirring and heating are commenced.
  • the temperature (reaction temperature) at which each component is stirred may be the reflux temperature of the aliphatic hydrocarbon solvent or aromatic solvent, but in order to minimize coloration of the resulting first bismuth compound, it is preferable to carry out the reaction at an oil bath temperature of 30 to 150°C, more preferably 40 to 140°C, and even more preferably 45 to 120°C.
  • Examples of compounds having an imidazole skeleton include imidazole, 1-vinylimidazole, 1-allylimidazole, N-acetylimidazole, benzimidazole, 1-methylimidazole, 1-ethylimidazole, 1-propylimidazole, 1-cyanomethylimidazole, 1-(3-aminopropyl)imidazole, 2-methylimidazole, 2-methyl-1-vinylimidazole, 2-hydroxymethyl-1-methylimidazole, 4-hydroxymethyl-5-methylimidazole, 2-formyl-1-vinyl
  • Examples of the compound having an imidazole skeleton include imidazole, 2-ethylimidazole, 2-propylimidazole, 2-chloroimidazole, 2-nitroimidazole, 4-nitroimidazole, 4-methylimidazole, 4-fluoroimidazole, 2-formylimidazole, 2-ethyl-4-imidazole,
  • Examples of compounds having a 1,2,3-triazole skeleton include 1,2,3-triazole, 1H-benzotriazole, and 2H-benzotriazole. It is preferable that the compound having a 1,2,3-triazole skeleton contains 1,2,3-triazole.
  • the compound having a 1,2,4-triazole skeleton has a skeleton represented by the following formula (d).
  • the compound having a tetrazole skeleton has a skeleton represented by the following formula (e).
  • the coordinating organic compound includes, for example, an unsaturated carboxylic acid anhydride.
  • unsaturated carboxylic acid anhydride include acrylic acid anhydride, methacrylic acid anhydride, and maleic acid anhydride.
  • the coordinating organic compound preferably contains at least one compound selected from the group consisting of a compound having an imidazole skeleton, a compound having a pyrazole skeleton, a compound having a triazole skeleton, a compound having a tetrazole skeleton, a compound having at least one heteroatom selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom and an unsaturated bond, an unsaturated dicarboxylic acid, and an unsaturated carboxylic acid ester, and an unsaturated carboxylic acid anhydride.
  • an unsaturated carboxylic acid anhydride When an unsaturated carboxylic acid anhydride is contained, water absorption tends to be enhanced.
  • the proportion of the coordinating organic compound when the proportion of the coordinating organic compound is high, the odor of the cured body tends to be reduced.
  • the proportion of the coordinating organic compound is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, and even more preferably 1.0% by mass or more.
  • the proportion of the coordinating organic compound when the proportion of the coordinating organic compound is excessively high, the radiation shielding ability of the cured body may be reduced.
  • the proportion of the coordinating organic compound in the curable composition is preferably 8% by mass or less, more preferably 7% by mass or less, and even more preferably 5% by mass or less. This proportion can be measured, for example, by 1H MNR.
  • the total content of the first bismuth compound and the coordinating organic compound is preferably 10% by mass or more and 90% by mass or less.
  • Examples of the first polymerizable compound having an acryloyl group include various commercially available monofunctional radical polymerizable compounds such as acrylic acid, acrylamide, phenyl acrylate, benzyl acrylate, isobutyl acrylate, methoxyethyl acrylate, ethoxyethyl acrylate, tetrahydrofurfuryl acrylate, isocyanatoethyl acrylate, and acryloxymethyltrimethoxysilane.
  • monofunctional radical polymerizable compounds such as acrylic acid, acrylamide, phenyl acrylate, benzyl acrylate, isobutyl acrylate, methoxyethyl acrylate, ethoxyethyl acrylate, tetrahydrofurfuryl acrylate, isocyanatoethyl acrylate, and acryloxymethyltrimethoxysilane.
  • Examples of the first polymerizable compound having a vinyl group include various commercially available monofunctional radical polymerizable monomers such as vinylpyridine, vinylpyrrolidone, methylstyrene and its structural isomers, methoxystyrene and its structural isomers, methylstyrene dimer, chlorostyrene, bromostyrene, and divinylbenzene.
  • monofunctional radical polymerizable monomers such as vinylpyridine, vinylpyrrolidone, methylstyrene and its structural isomers, methoxystyrene and its structural isomers, methylstyrene dimer, chlorostyrene, bromostyrene, and divinylbenzene.
  • the curable composition according to the present embodiment preferably contains two or more kinds of (meth)acrylates represented by the above formula (I), and more preferably contains at least one of (meth)acrylates in which R 1 in the above formula (I) is a tetrahydrofuryl group and (meth)acrylates in which R 1 in the above formula (I) is a methoxy group.
  • the curable composition contains a (meth)acrylate in which R 1 is a tetrahydrofuryl group, the compatibility of the first bismuth compound tends to be increased.
  • the curable composition contains a (meth)acrylate in which R 1 is a methoxy group, the hardness of the cured body tends to be increased.
  • the total amount of polymerizable compounds is preferably 1 to 20,000 parts by mass, more preferably 25 to 15,000 parts by mass, and even more preferably 10 to 9,900 parts by mass per 100 parts by mass of the first bismuth compound.
  • the hardened product according to this embodiment has antibacterial and antiviral properties, and can therefore be used in applications where high hygiene is required.
  • Example 2 The same procedure as in Example 1 was carried out except that 1 part by mass of dimethylaminoethyl methacrylate was used instead of 2-methylimidazole, to obtain a pale yellow, transparent cured product. The results are shown in Table 1.
  • Example 3 The same procedure as in Example 1 was carried out except that 1 part by mass of imidazole was used instead of 2-methylimidazole, to obtain a pale yellow, transparent cured product. The results are shown in Table 1.
  • Example 5 The same procedure as in Example 1 was carried out except that 1 part by mass of 4-methylimidazole was used instead of 2-methylimidazole, to obtain a pale yellow, transparent cured product. The results are shown in Table 1.
  • Example 16> The same procedure as in Example 1 was carried out except that 1 part by mass of 1,2-dimethylimidazole was used instead of 2-methylimidazole, to obtain a pale yellow, transparent cured product. The results are shown in Table 1.
  • Example 3 The cured product obtained in Example 3 was quantitatively analyzed for odor components by GC/MS analysis and NMR analysis.
  • Agilent 7890B was used for GC
  • Agilent 597xMSD was used for MS
  • Agilent 7697A was used for the headspace sampler
  • Agilent 19091S-433 HP-5ms was used for the column (all manufactured by Agilent Technologies).
  • the cured product of Example 3 was crushed, and the fragments (1 g) were placed in a dedicated vial tube with a capacity of 10 mL, and equilibrated at 90 ° C. for 30 minutes using a headspace sampler, and then the volatile components were introduced into a GC/MS at an oven temperature of 250 ° C.

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PCT/JP2023/043787 2022-12-09 2023-12-07 組成物、硬化性組成物、硬化体、光学物品、レンズ、眼鏡、抗菌・抗ウイルス剤、及び樹脂組成物 Ceased WO2024122605A1 (ja)

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JP2024562987A JPWO2024122605A1 (https=) 2022-12-09 2023-12-07
CN202380083279.1A CN120435519A (zh) 2022-12-09 2023-12-07 组合物、固化性组合物、固化物、光学物品、镜片、眼镜、抗菌/抗病毒剂及树脂组合物
EP23900717.2A EP4632004A1 (en) 2022-12-09 2023-12-07 Composition, curable composition, cured body, optical product, lens, eyeglasses, antimicrobial/antiviral agent, and resin composition

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6004546A (en) * 1996-11-15 1999-12-21 Medeva Europe Limited Pharmaceutical composition containing bismuth-polyacrylic acid compounds
WO2019177084A1 (ja) 2018-03-16 2019-09-19 株式会社トクヤマ ビスマス化合物、硬化性組成物、および硬化体
JP2021135170A (ja) * 2020-02-27 2021-09-13 国立大学法人 鹿児島大学 有機化合物被覆酸化ビスマス粒子の製造方法、放射線遮蔽部材の製造方法、及び放射線遮蔽部材
WO2022014591A1 (ja) * 2020-07-17 2022-01-20 株式会社トクヤマ 硬化性組成物及びその硬化体
JP2022128911A (ja) * 2021-02-24 2022-09-05 三菱瓦斯化学株式会社 重合性組成物及びそれを重合硬化してなる樹脂

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6004546A (en) * 1996-11-15 1999-12-21 Medeva Europe Limited Pharmaceutical composition containing bismuth-polyacrylic acid compounds
WO2019177084A1 (ja) 2018-03-16 2019-09-19 株式会社トクヤマ ビスマス化合物、硬化性組成物、および硬化体
JP2021135170A (ja) * 2020-02-27 2021-09-13 国立大学法人 鹿児島大学 有機化合物被覆酸化ビスマス粒子の製造方法、放射線遮蔽部材の製造方法、及び放射線遮蔽部材
WO2022014591A1 (ja) * 2020-07-17 2022-01-20 株式会社トクヤマ 硬化性組成物及びその硬化体
JP2022128911A (ja) * 2021-02-24 2022-09-05 三菱瓦斯化学株式会社 重合性組成物及びそれを重合硬化してなる樹脂

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
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EP4632004A1 (en) 2025-10-15

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