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WO2025220627A1 - Composition d'organopolysiloxane durcissable à température ambiante - Google Patents

Composition d'organopolysiloxane durcissable à température ambiante

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Publication number
WO2025220627A1
WO2025220627A1 PCT/JP2025/014591 JP2025014591W WO2025220627A1 WO 2025220627 A1 WO2025220627 A1 WO 2025220627A1 JP 2025014591 W JP2025014591 W JP 2025014591W WO 2025220627 A1 WO2025220627 A1 WO 2025220627A1
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group
carbon atoms
mass
parts
component
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PCT/JP2025/014591
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English (en)
Japanese (ja)
Inventor
功 岩崎
守 勅使河原
宗直 廣神
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Shin Etsu Chemical Co Ltd
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Shin Etsu Chemical Co Ltd
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Publication of WO2025220627A1 publication Critical patent/WO2025220627A1/fr
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Classifications

    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/013—Fillers, pigments or reinforcing additives
    • 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
    • C08K5/54—Silicon-containing compounds
    • C08K5/541—Silicon-containing compounds containing oxygen
    • C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
    • 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
    • C08K5/54—Silicon-containing compounds
    • C08K5/544—Silicon-containing compounds containing nitrogen
    • C08K5/5445—Silicon-containing compounds containing nitrogen containing at least one Si-N bond
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups

Definitions

  • the present invention relates to a room-temperature-curable organopolysiloxane composition that cures at room temperature to form silicone rubber. Specifically, after curing, it provides a silicone rubber that has excellent self-adhesion to glass, various metals, resins, etc., and is a low-odor room-temperature-curable organopolysiloxane composition that has excellent storage stability, especially when packaged in a sealed container.
  • Such one-component, room-temperature-curing organopolysiloxane compositions are often classified by the compounds released from the composition upon contact with moisture in the air, with representative examples including deacetic acid, deoxime, deamido, dehydroxylamine, deacetone, and dealcohol organopolysiloxane compositions.
  • dealcohol-curing organopolysiloxane compositions which cure by releasing alcohol, are particularly preferred for their low odor, non-corrosion to metals such as copper and iron, excellent self-adhesion (adhesion to various substrates after curing when no primer is used), and excellent adhesive durability.
  • one-component, dealcohol-free organopolysiloxane compositions have the excellent properties described above for a short period after production, they have shortcomings in storage stability, such as losing the properties they had immediately after production over time during storage, depending on the formulation. Furthermore, storage in direct sunlight at the site of use or in high-temperature environments exceeding 40°C, such as when stored in a container during transport, can cause problems such as the original properties not being achieved or poor curing, even for a relatively short period of time.
  • Patent Document 1 proposes a composition comprising a hydroxyl-terminated organopolysiloxane, an alkoxysilane, and a titanium compound.
  • Patent Document 2 proposes a composition comprising an organopolysiloxane having an alkoxysiloxy group at its terminal, an alkoxysilane, and an alkoxytitanium.
  • Patent Document 3 proposes a composition that improves storage stability by using a scavenger with an organosilazane structure to capture alcohol compounds within the composition.
  • This technology improves storage stability, particularly when hexamethyldisilazane is selected as the scavenger.
  • hexamethyldisilazane has a low boiling point, is highly volatile, and has a pungent odor, compositions containing it also produce a strong odor.
  • ammonia and trimethylmethoxysilane are by-produced during alcohol capture, resulting in an even stronger odor over time, thereby compromising the low odor that is an advantage of dealcohol-based compositions.
  • Patent Document 4 proposes a composition that exhibits excellent storage stability when sealed.
  • the composition proposed here requires the use of a polymer in which an alkoxysilyl alkylene group is modified at the end of an organopolysiloxane, and the preparation of this polymer raises problems such as high industrial costs.
  • Patent Document 5 Japanese Patent Laid-Open Publication Nos. 2-38309 (Patent Document 5) and 2003-176411 (Patent Document 6) propose compositions that use calcium carbonate treated with a fatty acid ester.
  • these compositions have problems such as insufficient storage stability when stored at high temperatures above 50°C, and because calcium carbonate treated with a fatty acid ester is used as a special filler, compositions containing large amounts of this filler are expensive.
  • an object of the present invention is to provide a dealcohol-type, room-temperature-curable organopolysiloxane composition that cures at room temperature in the presence of atmospheric moisture to produce a silicone rubber cured product, and in particular, a room-temperature-curable organopolysiloxane composition that has excellent storage stability when packaged in a sealed container and has little odor.
  • the present invention provides the following room-temperature-curable organopolysiloxane composition.
  • a room-temperature-curable organopolysiloxane composition comprising the following components (A), (B), (C), and (D): (A) 100 parts by mass of a diorganopolysiloxane represented by the following general formula (1) having a viscosity at 25°C of 20 to 1,000,000 mPa ⁇ s:
  • R 1 is independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an alkoxyalkyl group having 2 to 10 carbon atoms
  • R 2 is independently a group having 1 to 10 carbon atoms selected from monovalent hydrocarbon groups, halogenated monovalent hydrocarbon groups, and cyanoalkyl groups
  • a is 2 when R 1 is a hydrogen atom; and it is 0 or 1 when R 1 is an alkyl group having 1 to 10 carbon atoms or an alkoxyalkyl group having 2 to 10 carbon atoms
  • Y is an oxygen atom, a divalent hydrocarbon group having 1 to 6 carbon
  • the room-temperature-curable organopolysiloxane composition of the present invention has excellent storage stability when packaged in a sealed container, has little odor, and after curing gives a cured product with excellent adhesion to glass, painted aluminum, and other surfaces without the need for a primer, making it useful as a coating material, sealant, and adhesive.
  • the room-temperature-curable organopolysiloxane composition of the present invention contains the following components (A), (B), (C), and (D).
  • the diorganopolysiloxane of component (A) is the main component of the composition. It is a diorganopolysiloxane represented by the following general formula (1), which has hydroxy groups, alkoxy groups, or alkoxyalkoxy groups at both molecular chain terminals: Furthermore, if the viscosity is too low, the rubber elasticity after curing will be poor, and if it is too high, workability will be reduced, so the viscosity at 25°C must be in the range of 20 to 1,000,000 mPa ⁇ s, and preferably in the range of 100 to 100,000 mPa ⁇ s. Note that this viscosity is measured using a rotational viscometer at 25°C.
  • the molecular structure of this organopolysiloxane is substantially linear, that is, the structure of the siloxane bond chain made of SiO is linear, but part of the molecular chain, such as the alkyl group that is the side chain, may be branched.
  • R 1 is independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an alkoxyalkyl group having 2 to 10 carbon atoms
  • R 2 is independently a group having 1 to 10 carbon atoms selected from monovalent hydrocarbon groups, halogenated monovalent hydrocarbon groups, and cyanoalkyl groups
  • a is 2 when R 1 is a hydrogen atom; and it is 0 or 1 when R 1 is an alkyl group having 1 to 10 carbon atoms or an alkoxyalkyl group having 2 to 10 carbon atoms
  • Y is an oxygen atom, a divalent hydrocarbon group having 1 to 6 carbon atoms, or a group represented by the following general formula (2)
  • n is a number that gives the diorganopolysiloxane a viscosity at 25°C of 20 to 1,000,000 mPa ⁇ s.
  • R 1 is, for example, a group selected from a hydrogen atom, an alkyl group having 1 to 10 carbon atoms such as a methyl group, an ethyl group, a propyl group, a butyl group, or an octyl group; or an alkoxyalkyl group having 2 to 10 carbon atoms such as a methoxymethyl group, a methoxyethyl group, or an ethoxymethyl group, and is preferably a hydrogen atom, a methyl group, or an ethyl group.
  • R2 may be, for example, a group having 1 to 10 carbon atoms selected from monovalent hydrocarbon groups, halogenated monovalent hydrocarbon groups, and cyanoalkyl groups.
  • monovalent hydrocarbon groups include alkyl groups such as methyl, ethyl, propyl, butyl, and octyl; cycloalkyl groups such as cyclopentyl and cyclohexyl; alkenyl groups such as vinyl and allyl; aryl groups such as phenyl, tolyl, and naphthyl; and aralkyl groups such as benzyl, phenylethyl, and phenylpropyl.
  • halogenated monovalent hydrocarbon groups include trifluoropropyl and chloropropyl.
  • cyanoalkyl groups include ⁇ -cyanoethyl and ⁇ -cyanopropyl groups. Of these, a methyl group is preferred.
  • a is 2 when R 1 is a hydrogen atom, and is 0 or 1 when R 1 is an alkyl group having 1 to 10 carbon atoms or an alkoxyalkyl group having 2 to 10 carbon atoms.
  • Y is an oxygen atom, a divalent hydrocarbon group having 1 to 6 carbon atoms, or a group represented by the following general formula (2).
  • the divalent hydrocarbon group having 1 to 6 carbon atoms an alkylene group having 1 to 6 carbon atoms such as methylene, ethylene, propylene, trimethylene, butylene, tetramethylene, hexene, or hexamethylene is preferred, with an ethylene group being particularly preferred.
  • the hydrogen atom of the alkylene group may be substituted with a monovalent hydrocarbon group such as a methyl group.
  • R2 is independently a group having 1 to 10 carbon atoms selected from a monovalent hydrocarbon group, a halogenated monovalent hydrocarbon group, and a cyanoalkyl group, and Z is a divalent hydrocarbon group having 1 to 6 carbon atoms.
  • R 2 may be the same as R 2 in formula (1).
  • the divalent hydrocarbon group represented by Z is preferably an alkylene group having 1 to 6 carbon atoms, such as methylene, ethylene, propylene, trimethylene, butylene, tetramethylene, hexene, or hexamethylene, with ethylene being particularly preferred.
  • the hydrogen atoms of the alkylene group may be substituted with monovalent hydrocarbon groups, such as methyl.
  • n is a number that gives a viscosity at 25°C of 20 to 1,000,000 mPa ⁇ s.
  • the component (A) may be used alone or in combination of two or more types.
  • Component (A) can be produced by a known method.
  • the content of component (A) in the entire composition of the present invention is preferably 20 to 95% by mass, and more preferably 30 to 90% by mass.
  • Component (B) is an alkoxy or enoxy silane compound and/or a partial hydrolysis condensate thereof, in which the functional group bonded to the silicon atom is a hydrocarbon group that does not contain heteroatoms such as nitrogen (N) or sulfur (S) other than oxygen (O), and serves to cure the room-temperature-curable organopolysiloxane composition of the present invention and to adjust the curing rate by adjusting the amount added.
  • component (B) is preferably one in which the functional group bonded to the silicon atom, other than the alkoxy or enoxy group, does not contain heteroatoms such as oxygen (O), nitrogen (N), or sulfur (S).
  • the alkoxy or enoxy silane of component (B) includes alkoxy group-containing compounds such as tetramethoxysilane, methyltrimethoxysilane, vinyltrimethoxysilane, phenyltrimethoxysilane, tetraethoxysilane, methyltriethoxysilane, vinyltriethoxysilane, phenyltriethoxysilane, tetrapropoxysilane, tetraisopropoxysilane, ethyltrimethoxysilane, propyltrimethoxysilane, isobutyltrimethoxysilane, normal butyltrimethoxysilane, normal hexyltrimethoxysilane, decyltrimethoxysilane, and their partial hydrolysis condensates; substituted alkoxy group-containing compounds such as tetrakis(2-ethoxyethoxy)silane, methyltris(2-meth
  • the alkoxy or enoxy silane may be used alone or in combination of two or more.
  • the amount of component (B) blended is 0.5 to 20 parts by mass, and preferably 0.5 to 15 parts by mass, per 100 parts by mass of component (A). Furthermore, when R 1 in general formula (1) representing component (A) is a hydrogen atom, in order to obtain good curability and storage stability, the number of moles of alkoxy groups in component (B) per mole of hydroxyl groups in component (A) is preferably more than 1 mol, and more preferably 2 to 30 mol.
  • Component (C) is a curing catalyst, and examples of the curing catalyst include organic carboxylates, alkoxides, and chelate compounds of metals such as tin, aluminum, zirconium, titanium, iron, antimony, bismuth, and manganese.
  • these include tin compounds such as dibutyltin dilaurate, dibutyltin dioctoate, dioctyltin dilaurate, dibutyltin maleate ester, dimethyltin dineodecanoate, dibutyltin dimethoxide, dioctyltin dineodecanoate, and stannous octoate; organic aluminum compounds such as aluminum tris(acetylacetonate), aluminum tris(ethylacetoacetate)diisopropoxyaluminum ethylacetoacetate, and triethoxyaluminum; zirconium tetrakis(acetylacetonate), tetraisopropoxyzirconium, tetrabutoxyzirconium, and tributoxyzirconium acetone.
  • tin compounds such as dibutyltin dilaurate, dibutyltin dioctoate, di
  • titanium chelate examples include organic zirconium compounds such as tetra-normal-butoxytitanium, tetrakis(2-ethylhexoxy)titanium, tetraisopropoxytitanium, and tetra-tertiary-butoxytitanium; titanium chelate compounds such as diisopropoxybis(acetylacetonato)titanium, diisopropoxybis(ethylacetoacetate)titanium, and dibutoxybis(methylacetoacetate)titanium; and amine compounds such as dibutylamine, laurylamine, tetramethylguanidine, and tetramethylguanidylpropyltrimethoxysilane, as well as salts thereof.
  • organic zirconium compounds such as tetra-normal-butoxytitanium, tetrakis(2-ethylhexoxy)titanium, tetraisopropoxyt
  • component (C) is 0.001 to 20 parts by mass, preferably 0.01 to 10 parts by mass, per 100 parts by mass of component (A).
  • Component (D) is an organosilicon compound represented by the following formula (3).
  • R 1 is independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an alkoxyalkyl group having 2 to 10 carbon atoms
  • R 2 is independently a group having 1 to 10 carbon atoms selected from a monovalent hydrocarbon group, a halogenated monovalent hydrocarbon group, and a cyanoalkyl group
  • R 3 is independently an alkylene group having 1 to 10 carbon atoms
  • m is a number from 1 to 3.
  • R 1 and R 2 are the same as R 1 and R 2 in formula (1), respectively.
  • R 3 is independently an alkylene group having 1 to 10 carbon atoms, such as a methylene group, a dimethylene group, a trimethylene group, or a butylene group, and among these, a methylene group, a dimethylene group, or a trimethylene group is preferred.
  • component (D) includes the following:
  • the amount of component (D) added is 0.1 to 5 parts by mass, and preferably 0.2 to 3 parts by mass, per 100 parts by mass of component (A). If it is less than 0.1 part by mass, the effect of imparting sufficient storage stability to the composition will not be obtained, and if it exceeds 5 parts by mass, the self-adhesive properties of the composition may decrease.
  • composition of the present invention may also contain an inorganic filler (E).
  • Component (E) functions to impart good mechanical properties to the cured product of the composition of the present invention.
  • component (E) examples include wet silica, fumed silica produced by a dry method, silicas whose surfaces have been treated with chlorosilanes such as dichlorodimethylsilane and trichloromethylsilane, silazanes such as hexamethyldisilazane, or siloxanes such as octamethyltetrasiloxane, heavy (or pulverized) calcium carbonate, precipitated calcium carbonate, and powders of these calcium carbonates whose surfaces have been treated with an organic acid such as a fatty acid or a resin acid, an alkali metal salt of an organic acid, an organic acid ester, or the like.
  • chlorosilanes such as dichlorodimethylsilane and trichloromethylsilane
  • silazanes such as hexamethyldisilazane
  • siloxanes such as octamethyltetrasiloxane
  • heavy (or pulverized) calcium carbonate precipit
  • inorganic fillers such as fumed silica, precipitated calcium carbonate, heavy calcium carbonate, alumina, and aluminum hydroxide can be used alone or in combination of two or more types depending on the desired properties of the composition.
  • fumed silica it is preferably 30 to 400 m 2 /g
  • precipitated calcium carbonate whose surface has been treated with various organic substances it is preferably 5 to 50 m 2 /g, and particularly preferably 10 to 40 m 2 /g.
  • the precipitated calcium carbonate without surface treatment has spindle-shaped primary particles that are agglomerated during production, and preferably has an area of 1 to 20 m 2 /g, particularly preferably 3 to 10 m 2 /g.
  • the ground calcium carbonate, whether the surface is untreated or treated with an organic substance preferably has a specific area of 1 to 15 m 2 /g.
  • the blending amount is preferably in the range of 1 to 300 parts by mass, and more preferably in the range of 5 to 200 parts by mass, per 100 parts by mass of component (A). If the blending amount of component (E) is less than the lower limit of the above range, the properties of component (E) may not be obtained, while if the blending amount exceeds the upper limit of the above range, the handling and workability of the composition of the present invention may be impaired.
  • composition of the present invention may contain a silane coupling agent (F).
  • Component (F) further improves the adhesion of the composition of the present invention to various substrates.
  • Component (F) is a compound other than components (B) and (D), and is preferably one known in the relevant technical field.
  • compounds having an alkoxysilyl group or alkenoxysilyl group as the hydrolyzable group are preferred, such as ⁇ -methacryloxypropyltrimethoxysilane, ⁇ -(3,4-epoxycyclohexyl)ethyltrimethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropylmethyldiethoxysilane, N- ⁇ -(aminoethyl)- ⁇ -aminopropyltrimethoxysilane, ⁇ -aminopropyltriethoxysilane, 3-(N-aminomethylbenzylamino)propyltrimethoxysilane, 3-(N-aminomethylbenzylamino)propyltriethoxy ...
  • Examples include methoxysilane, N,N'-bis[3-(trimethoxysilyl)propyl]ethylenediamine, N,N-bis[3-(trimethoxysilyl)propyl]amine, ⁇ -mercaptopropyltrimethoxysilane, ⁇ -glycidoxypropyltriisopropenoxysilane, ⁇ -glycidoxypropylmethyldiisopropenoxysilane, reaction products of (meth)acrylicsilane and aminosilane, reaction products of epoxysilane and aminosilane, and reaction products of aminosilane and silane containing a halogenated alkyl group. It is particularly preferable to use a silane coupling agent containing at least one amino group in the molecule.
  • the blending amount is preferably 0.1 to 20 parts by mass, and especially 0.5 to 10 parts by mass, per 100 parts by mass of component (A). Less than 0.1 part by mass will not provide the improvement in adhesion achieved by adding component (F), while more than 20 parts by mass will not only be cost-effective but may also result in a decrease in hot water resistance.
  • additives include inorganic fillers other than component (E), such as fine quartz powder, titanium dioxide powder, diatomaceous earth powder, aluminum hydroxide powder, fine particle alumina, magnesia powder, zinc oxide powder, and fine powder-like inorganic fillers obtained by surface-treating these with silanes, silazanes, low-polymerization polysiloxanes, etc.
  • the amount of such inorganic fillers added is 10 to 200 parts by mass, and preferably 30 to 150 parts by mass, per 100 parts by mass of component (A).
  • additives include components for lowering the modulus of the silicone rubber after curing, such as dialkoxysilanes (e.g., diphenyldimethoxysilane, dimethyldimethoxysilane), dimethylpolysiloxanes capped at both ends with trimethylsiloxy groups, isoparaffin, platinum compounds as flame retardants, zinc carbonate powder, polyethers as thixotropy improvers as needed, colorants (e.g., pigments, dyes, fluorescent brighteners), heat resistance improvers (e.g., red iron oxide, cerium oxide), cold resistance improvers, rust inhibitors, mildew inhibitors, antibacterial agents, etc.
  • solvents such as toluene, xylene, solvent volatile oil, cyclohexane, methylcyclohexane, and low-boiling point isoparaffin may also be added.
  • the composition of the present invention can be produced as a so-called one-component, dealcohol-removing organopolysiloxane composition by blending the above-described components (A) to (D), and, if necessary, component (E), component (F), and other components, in a dry atmosphere according to a conventional method. Thereafter, the composition is preferably stored in a sealed package.
  • a container for sealing and packaging a cylindrical cartridge made of polyethylene or polypropylene is most preferred in order to maximize the effect of the composition of the present invention.
  • the composition of the present invention usually cures in the presence of moisture in the air when left to stand in the air.
  • the composition of the present invention can be used in a variety of applications, but is particularly useful as a coating material, a sealant, or an adhesive.
  • the viscosity values in the examples are measured at 25°C using a rotational viscometer (TVB-10M, manufactured by Toki Sangyo Co., Ltd.), and all parts are parts by mass.
  • all compositions of the present invention were prepared using a mixer/stirrer (model: 5DMV-01-r) manufactured by Dalton Co., Ltd.
  • Example 1 500 g (100 parts by mass) of dimethylpolysiloxane (viscosity 50,000 mPa ⁇ s) in which both molecular chain terminals are capped with dimethoxymethylsiloxy groups, 25 g (5 parts by mass) of methyltrimethoxysilane, 10 g (2 parts by mass) of vinyltrimethoxysilane, and 2.5 g (0.5 parts by mass) of 3-(2-aminoethylamino)propyltrimethoxysilane were mixed uniformly at room temperature of 23°C and atmospheric pressure for 10 minutes. After stopping the mixing, the mixture was allowed to stand for 18 hours in a sealed container at 23°C.
  • the BET specific surface area of the mixture was 105 m2.
  • MU-215 manufactured by Shin-Etsu Chemical Co., Ltd.
  • Organopolysiloxane Composition 2 was obtained in the same manner as in Example 1, except that the amount of organosilicon compound 1 synthesized in Synthesis Example 1 added was changed from 8.5 g (1.7 parts by mass) to 4.0 g (0.8 parts by mass).
  • Organopolysiloxane Composition 3 was obtained in the same manner as in Example 1, except that the organosilicon compound 1 synthesized in Synthesis Example 1 was replaced with the same amount of organosilicon compound 2 synthesized in Synthesis Example 2.
  • Example 4 500 g (100 parts by mass) of dimethylpolysiloxane (viscosity 50,000 mPa ⁇ s) having one hydroxyl group (silanol group) bonded to a silicon atom at each end of the molecular chain, 25 g (5 parts by mass) of methyltrimethoxysilane, and 8.5 g (1.7 parts by mass) of 3-(2-aminoethylamino)propyltrimethoxysilane were mixed uniformly at room temperature of 23°C and atmospheric pressure for 10 minutes to prepare a mixture. After stopping the mixing, the mixture was allowed to stand for 18 hours in a sealed container at 23°C, and then the mixture was measured to have a BET specific surface area of 150 m2.
  • Organopolysiloxane Composition 7 was obtained in the same manner as in Example 1, except that in Example 4, the organosilicon compound 1 prepared in Synthesis Example 1 was replaced with the same amount of N,N-bis(trimethylsilyl)-3-aminopropyltrimethoxysilane.
  • Organopolysiloxane Composition 8 was obtained in the same manner as in Example 1, except that the organosilicon compound 1 prepared in Synthesis Example 1 was replaced with the same amount of hexamethyldisilazane.
  • Organopolysiloxane Composition 9 was obtained in the same manner as in Comparative Example 4, except that the amount of hexamethyldisilazane added was 0.2 parts by mass.
  • Organopolysiloxane Composition 10 was obtained in the same manner as in Example 4, except that the organosilicon compound 1 prepared in Synthesis Example 1 was replaced with the same amount of hexamethyldisilazane.
  • organopolysiloxane compositions prepared in the Examples and Comparative Examples were evaluated for physical properties, adhesion, and storage stability. Each evaluation was carried out according to the methods described below, and the results for the compositions obtained in the Examples and Comparative Examples are shown in Tables 1 and 2.
  • the prepared composition was extruded into a polyethylene frame and left to cure for 7 days under conditions of a temperature of 23°C and a relative humidity of 50%, to prepare a sheet having a thickness of 2 mm.
  • the physical properties of this sheet were measured in accordance with JIS K 6249.
  • the composition was placed in a cylindrical polyethylene sealant cartridge (volume 330 ml) and sealed with an inner stopper.
  • the cartridge was stored for 28 days in a thermo-hygrostat controlled at a temperature of 70°C and a relative humidity of 20%, and then removed and left at a temperature of 23°C and a relative humidity of 50% for 1 day.
  • the stored composition was then evaluated for physical properties and odor.
  • a hardness that was less than ⁇ 5 points higher than the hardness before storage (immediately after preparation) was considered acceptable, and a hardness that was more than ⁇ 5 points higher than the hardness before storage (immediately after preparation) was considered unacceptable.
  • the organopolysiloxane compositions obtained in Examples 1 to 4 have a low odor and exhibit excellent storage stability even when left in heated and humid environments, making them useful as waterproof sealants in construction and civil engineering applications, elastic adhesives, and coating materials in the electrical and electronics industries, among other applications.

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Abstract

L'invention concerne une composition d'organopolysiloxane durcissable à température ambiante ayant une excellente stabilité au stockage sous forme d'emballage scellé et dégageant moins d'odeur.　Cette composition d'organopolysiloxane durcissable à température ambiante comprend les composants (A), (B), (C) et (D) suivants. (A) est un diorganopolysiloxane ayant une viscosité de 20 à 1 000 000 mPa ∙ s à 25°C. (B) est un composé alcoxy ou énoxysilane dans lequel un groupe fonctionnel lié à un atome de silicium est un groupe hydrocarboné qui ne contient pas d'hétéroatome autre qu'un atome d'oxygène, et/ou un condensat partiellement hydrolysé de celui-ci. (C) est un catalyseur de durcissement. (D) est un composé d'organosilicium.
PCT/JP2025/014591 2024-04-16 2025-04-14 Composition d'organopolysiloxane durcissable à température ambiante Pending WO2025220627A1 (fr)

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Citations (6)

* Cited by examiner, † Cited by third party
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