WO2024247572A1 - オルガノポリシロキサン化合物、それを含む組成物、及びその硬化物 - Google Patents

オルガノポリシロキサン化合物、それを含む組成物、及びその硬化物 Download PDF

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WO2024247572A1
WO2024247572A1 PCT/JP2024/016219 JP2024016219W WO2024247572A1 WO 2024247572 A1 WO2024247572 A1 WO 2024247572A1 JP 2024016219 W JP2024016219 W JP 2024016219W WO 2024247572 A1 WO2024247572 A1 WO 2024247572A1
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organopolysiloxane
organopolysiloxane compound
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嵩之 鈴木
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Shin Etsu Chemical Co Ltd
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Shin Etsu Chemical Co Ltd
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Priority to EP24815057.5A priority patent/EP4692170A1/en
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    • 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
    • C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
    • C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
    • C08F299/08—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polysiloxanes
    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C08F290/068—Polysiloxanes
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/38—Polysiloxanes modified by chemical after-treatment
    • C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
    • C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/452—Block-or graft-polymers containing polysiloxane sequences containing nitrogen-containing sequences
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/48—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
    • C08G77/54—Nitrogen-containing linkages

Definitions

  • the present invention relates to an organopolysiloxane compound having an acryloyl group, which is a radically polymerizable functional group, a composition containing the same, and a cured product thereof.
  • photocurable resins that can be cured in a short time at room temperature have been attracting attention, and radically polymerizable acrylic compounds are mainly used as raw materials.
  • Such photocurable resins are used in paints, coating agents, inks, etc., and there are cases where properties such as high water repellency, antifouling properties, and lubricity are required.
  • a method for imparting high water repellency, antifouling properties, lubricity, and the like to a photocurable resin a method of blending and copolymerizing an organopolysiloxane having a (meth)acryloyl group is known (Patent Document 1).
  • organopolysiloxanes having (meth)acryloyl groups have low reactivity and are prone to problems such as the bleeding over time of unreacted organopolysiloxane from the cured resin (Patent Document 2). Therefore, there has been a strong desire for an organopolysiloxane compound that can solve this problem.
  • the present invention therefore aims to provide a highly reactive radically polymerizable organopolysiloxane compound, a composition containing the same, and a cured product thereof.
  • the present inventors have discovered that a specific organopolysiloxane compound having an acryloyl group can achieve the above object, and have thus completed the present invention. That is, the present invention is as follows.
  • W is expressed by the following formula (2):
  • R1 's are each independently a group selected from an alkyl group having 1 to 18 carbon atoms and an aryl group having 6 to 18 carbon atoms, and n is a number from 0 to 1,000.
  • Each L is independently an alkylene group having 2 to 12 carbon atoms;
  • Each X i is independently an alkyl group having 1 to 18 carbon atoms (wherein the alkyl group may have one or more bonds selected from an ether bond, an ester bond, an amide bond, and a hydroxyl group) and a group represented by the following formula (3):
  • Z is independently an oxygen atom, a sulfur atom, or a group represented by NR2 , where R2 in NR2 is a hydrogen atom or an alkyl group having 1
  • the organopolysiloxane compound of the present invention has high photocurability and reactivity, and is less likely to bleed when blended and copolymerized in a photocurable resin composition, etc. Furthermore, since it cures with little energy, it is possible to reduce energy consumption and shorten the process when producing a cured product.
  • the present invention is suitable for paints, coating agents, inks, and the like.
  • 1 is a 1 H-NMR spectrum chart of the organopolysiloxane compound synthesized in Example 1.
  • 1 is a GPC chart of the organopolysiloxane compound synthesized in Example 1.
  • Organopolysiloxane compound The organopolysiloxane compound of the present invention is represented by the following formula (1) and has an acryloyl group in one molecule, so that it easily reacts with a radically polymerizable compound.
  • W is a group represented by the following formula (2) (a divalent organopolysiloxane-containing group).
  • R1 is independently a group selected from an alkyl group having 1 to 18 carbon atoms and an aryl group having 6 to 18 carbon atoms, preferably a methyl group or a phenyl group, and more preferably a methyl group.
  • n is a number from 0 to 1,000, preferably a number from 3 to 500, and more preferably a number from 5 to 200. Examples of the group represented by formula (2) above include groups represented by the following formulas (4) to (7), but are not limited to these.
  • L is an alkylene group having 2 to 12 carbon atoms, preferably an alkylene group having 3 to 8 carbon atoms, and more preferably an alkylene group having 3 or 4 carbon atoms.
  • Xi is independently a group selected from an alkyl group having 1 to 18 carbon atoms (wherein the alkyl group may have one or more selected from an ether bond, an ester bond, an amide bond, and a hydroxyl group) and a group represented by the following formula (3), preferably a group represented by the following formula (3):
  • W, L and X i are the same as those in formula (1).
  • Each Z is independently an oxygen atom, a sulfur atom, or a group represented by NR 2 , preferably an oxygen atom.
  • R 2 in NR 2 is a hydrogen atom or an alkyl group having 1 to 12 carbon atoms, preferably a hydrogen atom.
  • M is a polyvalent organic group having a valence of b+1, preferably a polyvalent organic group having a valence of 2 to 6, more preferably a divalent to hexavalent aliphatic hydrocarbon group which may have an ether bond and a hydroxyl group.
  • i is a number from 1 to 30, preferably a number from 1 to 20, more preferably a number from 1 to 10.
  • i starts from 1.
  • a i is an integer from 0 to b, and a 10 is preferably 0.
  • b is a number from 1 to 20, preferably a number from 1 to 5.
  • Examples of the polyvalent organic group M include groups represented by the following formulae, but are not limited to these.
  • Xi examples include groups represented by the following formulae, but are not limited to these.
  • the number average molecular weight (Mn) of the organopolysiloxane compound represented by the above formula (1) is preferably 500 to 50,000, more preferably 1,000 to 30,000, and particularly preferably 2,000 to 20,000, and i in formula (3) is a number from 1 to 30 that satisfies the number average molecular weight (Mn).
  • the number average molecular weight (Mn) referred to in this specification refers to the number average molecular weight measured by GPC under the following conditions using polystyrene as the standard.
  • the organopolysiloxane compound of the present invention represented by the above formula (1) can be produced, for example, by the following method. That is, it can be produced by the Michael addition reaction of an organopolysiloxane having primary amino groups or secondary amino groups at both ends with a di- or higher functional acrylic compound, as shown in the following reaction formula (A).
  • W, L, Z, M, b, and Xi can be the same as those in the above formula (1).
  • X is independently a hydrogen atom or an alkyl group having 1 to 18 carbon atoms (wherein the alkyl group may have one or more selected from an ether bond, an ester bond, an amide bond, and a hydroxyl group), and when X is a hydrogen atom, that is, when the organopolysiloxane has a primary amino group, two equivalents of an acrylic group react with -NH2 , and Xi in the reaction product becomes a group represented by the above formula (3).
  • difunctional or higher acrylic compounds examples include difunctional acrylic monomers such as 1,6-hexanediol diacrylate, 1,9-nonanediol diacrylate, and tripropylene glycol diacrylate; trifunctional acrylic monomers such as trimethylolpropane triacrylate, ethoxylated trimethylolpropane triacrylate, glycerin triacrylate, and pentaerythritol triacrylate; tetrafunctional acrylic monomers such as pentaerythritol tetraacrylate, ethoxylated pentaerythritol tetraacrylate, and ditrimethylolpropane tetraacrylate; pentafunctional acrylic monomers such as dipentaerythritol pentaacrylate; hexafunctional acrylic monomers such as dipentaerythritol hexaacrylate; and oligomeric acrylic compounds such as urethane acrylate, polyester acrylate, and epoxy
  • the above reaction is preferably carried out by adding at least one equivalent of a difunctional or higher acrylic compound to the -NH- of the organopolysiloxane.
  • the reaction product is an organopolysiloxane compound represented by the above formula (1) that has excellent photocurability and reactivity.
  • the organopolysiloxane compound represented by formula (1) can be produced simply by mixing and heating an organopolysiloxane having an amino group and an acrylic compound having two or more functional groups; however, an acid catalyst or a base catalyst may be added as necessary.
  • the acid catalyst include AlCl 3 and MgCl 2 .
  • base catalysts include non-nucleophilic tertiary amines (N,N,N',N'-tetramethyl-1,8-naphthalenediamine, 1,8-diazabicyclo[5.4.0]undec-7-ene, etc.). These catalysts may be used alone or in combination of two or more.
  • the reaction temperature is not particularly limited, but is preferably 20 to 100°C, more preferably 50 to 80°C, for the purposes of preventing polymerization of the acrylic group and promoting the reaction.
  • the reaction time is not particularly limited, but is preferably from 3 to 24 hours, and more preferably from 6 to 18 hours.
  • the reaction is preferably carried out in the presence of a solvent.
  • a solvent facilitates compatibility between the organopolysiloxane having amino groups and the bifunctional or higher acrylic compound, which is preferable since it allows the Michael addition reaction to proceed efficiently.
  • the solvent is preferably one that does not have a group that can react with the amino group or the acrylic group, and examples of the solvent include hydrocarbons (toluene, xylene, n-hexane, cyclohexane, etc.) and ethers (diethyl ether, tetrahydrofuran, 1,4-dioxane, etc.). These solvents can be used alone or in combination of two or more types.
  • the reaction may be carried out by adding a polymerization inhibitor as necessary.
  • the polymerization inhibitor may be any one that has been conventionally used for acrylic compounds.
  • Examples of the polymerization inhibitor include phenol-based polymerization inhibitors such as hydroquinone, methylhydroquinone, hydroquinone monomethyl ether, 2-tert-butylhydroquinone, 4-methoxyphenol, and 2,6-di-tert-butyl-p-cresol. These polymerization inhibitors may be used alone or in combination of two or more.
  • the amount of the polymerization inhibitor is not particularly limited, but is preferably 5 to 1,000 ppm, more preferably 20 to 500 ppm, based on the mass of the resulting compound.
  • composition of the present invention contains the above-mentioned organopolysiloxane compound of the present invention.
  • the composition of the present invention may contain one or more acrylic compounds other than the organopolysiloxane compound of the present invention.
  • the organopolysiloxane compound of the present invention has high photocurability and reactivity, and therefore a composition containing this compound can be cured with little energy.
  • an unreacted difunctional or higher (b+1) acrylic compound e.g., polyfunctional acrylic monomer
  • This unreacted acrylic compound may be removed by solvent extraction or the like, or may be used as it is as a copolymerization monomer of the composition of the present invention. That is, the composition of the present invention may be obtained by obtaining the reaction product obtained in the above reaction as the composition of the present invention containing the organopolysiloxane compound represented by the above formula (1) and the difunctional or higher (b+1) acrylic compound.
  • the difunctional or higher (b+1) acrylic compound contained in the composition of the present invention may be exemplified by various acrylic compounds exemplified as the difunctional or higher (b+1) acrylic compound represented by the above reaction formula (A), and difunctional to hexafunctional acrylic monomers are preferred.
  • the composition of the present invention may be prepared by purifying a mixture of the organopolysiloxane compound represented by formula (1) obtained by the above reaction and an unreacted di- or higher-functional (b+1) acrylic compound by a conventional method and then adding one or more acrylic compounds, preferably b+1 polyfunctional acrylic monomers, more preferably di- to hexafunctional acrylic monomers.
  • the mixture of the organopolysiloxane compound represented by formula (1) obtained by the above reaction and the unreacted tri- or higher functional (b+1) acrylic compound may be used as is or after purification by a conventional method, and one or more acrylic compounds, preferably b+1 polyfunctional acrylic monomers, more preferably tri- to hexafunctional acrylic monomers, may be added separately to prepare the composition of the present invention.
  • the cured product of the present invention can be obtained by curing the composition of the present invention. The curing proceeds by radically polymerizing the composition with heat or light in a conventional manner to obtain the cured product.
  • the number average molecular weight and dispersity are polystyrene-equivalent values determined by GPC (gel permeation chromatography) measurement using tetrahydrofuran as a developing solvent under the following conditions.
  • GPC gel permeation chromatography
  • Developing solvent tetrahydrofuran Flow rate: 0.6 mL/min
  • Detector Refractive index detector (RI)
  • Column TSK Guard column Super H-H TSKgel SuperHM-N (6.0mm I.D.
  • TSKgel SuperH2500 (6.0mm I.D. x 15cm x 1) (Both manufactured by Tosoh Corporation) Column temperature: 40°C Sample injection volume: 50 ⁇ L (0.3% by weight tetrahydrofuran solution)
  • Example 1 A reaction vessel was charged with 70.5 g of an organopolysiloxane having amino groups at both ends, represented by the following formula (8-1), 31.4 g of 1,6-hexanediol diacrylate, 67.9 g of toluene, and 0.031 g of 2,6-di-tert-butyl-p-cresol, and the mixture was stirred at 70°C for 20 hours to prepare a mixed solution. The toluene was then removed from the mixed solution by distillation under reduced pressure to obtain a liquid. The obtained liquid was washed with 86.0 g of methanol, and the organopolysiloxane phase was recovered by liquid separation. The same washing operation was performed a total of three times, and the remaining methanol was then removed by distillation under reduced pressure to obtain 46.3 g of a liquid (FIGS. 1 and 2).
  • 8-1 an organopolysiloxane having amino groups at both ends
  • the obtained liquid was an organopolysiloxane represented by the following formula (1-1). (In the formula, a i is 0 or 1. i is a number from 1 to 8, provided that i starts at 1.)
  • Example 2 A reaction vessel was charged with 57.8 g of an organopolysiloxane having amino groups at both ends and represented by the following formula (8-2), 38.2 g of tripropylene glycol diacrylate, 64.0 g of toluene, and 0.029 g of 2,6-di-tert-butyl-p-cresol, and the mixture was stirred for 20 hours at 70° C. to prepare a mixed solution. Thereafter, the toluene was distilled off under reduced pressure from the mixed solution, yielding 91.7 g of a liquid product.
  • the obtained liquid was a mixture of organopolysiloxane represented by the following formula (1-2) and tripropylene glycol diacrylate.
  • a i is 0 or 1.
  • i is a number from 1 to 8, provided that i starts at 1.
  • Example 3 A reaction vessel was charged with 52.1 g of the organopolysiloxane having amino groups at both ends and represented by the above formula (8-2), 35.0 g of trimethylolpropane triacrylate, 58.1 g of toluene, and 0.026 g of 2,6-di-tert-butyl-p-cresol, and the mixture was stirred for 20 hours at 70° C. to prepare a mixed solution. Thereafter, the toluene was distilled off from the mixed solution under reduced pressure, yielding 80.6 g of a liquid product.
  • the obtained liquid was a mixture of organopolysiloxane represented by the following formula (1-3) and trimethylolpropane triacrylate.
  • a i is 0, 1, or 2.
  • i is a number from 1 to 10, provided that i starts at 1.
  • Example 4 A reaction vessel was charged with 3.98 g of the organopolysiloxane having amino groups at both ends and represented by the above formula (8-2), 11.6 g of dipentaerythritol hexaacrylate, 10.4 g of toluene, and 0.005 g of 2,6-di-tert-butyl-p-cresol, and the mixture was stirred for 20 hours at 70° C. to prepare a mixed solution. Thereafter, the toluene was distilled off from the mixed solution under reduced pressure, yielding 12.2 g of a liquid product.
  • the obtained liquid was a mixture of organopolysiloxane represented by the following formula (1-4) and dipentaerythritol hexaacrylate.
  • a i is 0, 1, or 2.
  • i is a number from 1 to 8, provided that i starts at 1.
  • a composition liquid was prepared by adding 0.020 g of Omnirad 1173, a photopolymerization initiator, manufactured by IGM Resins, to 10 g of each of the compositions of the above Examples or the compounds of the above Comparative Examples.
  • DHR2 Discovery Hybrid Rheometer
  • UV light source OmniCure SERIES 2000 (Excelitas Technologies)
  • UV illuminance 10mW/ cm2
  • Viscoelasticity measuring device DHR2 (Discovery Hybrid Rheometer) (TA Instruments) Measurement mode: Initial compression torque: 10.0 ⁇ N m Distortion: 10.0% Frequency: 25.0Hz Sample film thickness: 200 ⁇ m
  • a composition solution was prepared by adding 10 g of trimethylolpropane triacrylate and 0.1 g of Omnirad 1173 (IGM Resins) as a photopolymerization initiator to 0.5 g of the composition of the above example or the organopolysiloxane compound of the above comparative example, and the composition was applied to a polycarbonate substrate using a bar coater No. 4.
  • the above coating film was irradiated with UV having a wavelength of 365 nm and an intensity of 140 mW/ cm2 for 2 seconds under a nitrogen atmosphere to cure the coating film, and the presence or absence of bleeding was evaluated by touch.
  • Table 10 The results are shown in Table 10.
  • the organopolysiloxane compound of the present invention has a faster gel point and higher UV curability than conventional acrylic modified organopolysiloxanes.Surprisingly, it was found that the organopolysiloxane compound of the present invention, which is obtained by Michael addition of an organopolysiloxane compound having a primary amino group to a polyfunctional acrylic compound, has higher UV curability than the polyfunctional acrylic compound used as the raw material.In addition, from the results in Table 10, it was found that the organopolysiloxane compound of the present invention is less likely to bleed due to its high UV curability.
  • the organopolysiloxane compound of the present invention is useful as an ingredient for blending in UV-curable resin compositions, or as a UV-curable silicone elastomer, coating agent, or the like.

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  • Chemical Kinetics & Catalysis (AREA)
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PCT/JP2024/016219 2023-06-01 2024-04-25 オルガノポリシロキサン化合物、それを含む組成物、及びその硬化物 Ceased WO2024247572A1 (ja)

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CN202480034825.7A CN121263465A (zh) 2023-06-01 2024-04-25 有机聚硅氧烷化合物、含有其的组合物及其固化物
JP2025523358A JPWO2024247572A1 (https=) 2023-06-01 2024-04-25
EP24815057.5A EP4692170A1 (en) 2023-06-01 2024-04-25 Organopolysiloxane compound, composition containing same, and cured product thereof

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JP2021105100A (ja) * 2019-12-26 2021-07-26 Jsr株式会社 硬化性組成物、硬化膜、有機ｅｌ素子の製造方法及び化合物
JP2022138932A (ja) 2021-03-11 2022-09-26 Dic株式会社 アクリル樹脂、活性エネルギー線硬化性樹脂組成物、硬化物及び物品
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