Quality evaluation method for curable composition and shipping management method for curable composition

Abstract

To provide a quality evaluation method for a curable composition capable of simply and stably evaluating the quality of a curable composition.SOLUTION: Provided are a quality evaluation method for a curable composition, including a compound having a reactive silyl group, which is stored in a container, and its application, comprising detecting a peak attributable to a bond between a Si atom derived from the reactive silyl group and a reactive group by the Raman spectroscopy, and when defining peak intensity when the curable composition is stored in the container as peak intensity A, and the peak intensity after 60 days at 25°C from the time when the curable composition is stored in the container as peak intensity B, determining whether a degree of decrease in peak intensity, expressed by the following formula (1), is between 0 and 0.2: degree of decrease in peak intensity=(peak intensity A-peak intensity B) / (peak intensity A) ... (1).SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present disclosure relates to a method for evaluating the quality of a curable composition and a method for managing the shipment of a curable composition. [Background technology]

[0002] In recent years, there has been a demand for techniques that make it difficult for fingerprints to remain on the surface of an article and techniques that make it easy to remove stains in order to improve performance such as appearance and visibility. As a specific method, a method of treating the surface of an article using a curable composition as a surface treatment agent is known.

[0003] For example, Patent Document 1 describes a compound having a hydrolyzable silyl group that can form a surface treatment layer that has high initial water and oil repellency, and is excellent in abrasion resistance and fingerprint stain removability. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] International Publication No. 2013 / 121984 Summary of the Invention [Problem to be solved by the invention]

[0005] Typically, the compound having a hydrolyzable silyl group is diluted with a solvent and used as a composition. The solvent may contain a small amount of water. This solvent may cause water to be mixed into the composition. Water may also be mixed in when the composition is placed in a container. Therefore, in a container in which the composition is stored, the hydrolyzable silyl group may react with water, causing hydrolysis to proceed and resulting in a deterioration in quality. Therefore, a method for easily and stably evaluating the quality of a composition containing a compound having a reactive silyl group such as a hydrolyzable silyl group is desired.

[0006] The present disclosure has been made in view of the above circumstances, and an object of one embodiment of the present invention is to provide a method for evaluating the quality of a curable composition, which allows the quality of the curable composition to be evaluated simply and stably. An object of one embodiment of the present invention is to provide a method for managing shipment of a curable composition using the above-described method for evaluating the quality of a curable composition. [Means for solving the problem]

[0007] The present disclosure includes the following aspects. <1> In a curable composition containing a compound having a reactive silyl group, which is contained in a container, a peak attributable to a bond between a Si atom derived from the reactive silyl group and the reactive group is detected by Raman spectroscopy; The peak intensity when the curable composition is placed in a container is defined as peak intensity A, When the peak intensity after 60 days at 25°C from the time the curable composition was placed in a container was defined as peak intensity B, A method for evaluating the quality of a curable composition, comprising the step of determining whether or not the degree of decrease in peak intensity represented by the following formula (1) is 0 to 0.2: Peak intensity reduction rate = (peak intensity A - peak intensity B) / (peak intensity A) (1) <2> The compound having a reactive silyl group is at least one selected from the group consisting of the following compounds (1) to (3): <1> A method for evaluating the quality of a curable composition according to claim 1. Compound (1): A compound containing at least one selected from the group consisting of a fluoropolyether chain and a polyether chain, and a reactive silyl group. Compound (2): An acrylic polymer containing a reactive silyl group. Compound (3): A compound containing a chain organo(poly)siloxane residue and a reactive silyl group. <3> The compound having a reactive silyl group is at least one selected from the group consisting of compounds represented by the following formulas (2A) to (2C): <1> A method for evaluating the quality of a curable composition according to claim 1. R 1 [-Si(R 2 ) n L 3-n ] …(2A) [L 3-n (R 2 ) n Si-]Y 2 [-Si(R 2 ) n L 3-n ] …(2B) [R 1 -] p1 Y 3 [-Si(R 2 ) n L 3-n ] q1 …(2C) In formulas (2A) to (2C), R 1 are each independently a monovalent group, Y 2 is a divalent linking group, Y 3 is a (p1+q1)-valent linking group, p1 is an integer equal to or greater than 0, q1 is an integer equal to or greater than 1, p1+q1 is an integer equal to or greater than 3, R 2 are each independently a monovalent hydrocarbon group, L's each independently represent a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group; Each n is independently an integer of 0 to 2. <4> The curable composition further comprises a solvent. <1> ~ <3> The method for evaluating the quality of a curable composition according to any one of the above items. <5> The container is glass or resin. <1> ~ <4> 10. A method for evaluating the quality of a curable composition according to any one of the above items. <6> The curable composition is a surface treatment agent. <1> ~ <5> The method for evaluating the quality of a curable composition according to any one of the above items. <7> The surface treatment agent is used for surface treatment of optical articles. <6> A method for evaluating the quality of a curable composition according to claim 1. <8> The optical article is a touch panel or a display. <7> A method for evaluating the quality of a curable composition according to claim 1. <9> The curable composition is a sealant or adhesive. <1> ~ <5> The method for evaluating the quality of a curable composition according to any one of the above items. <10> The peaks are detected using a portable Raman spectrometer. <1> ~ <9> The method for evaluating the quality of a curable composition according to any one of the above items. <11> <1> ~ <10> The quality of the curable composition is evaluated by the quality evaluation method described in any one of If the reduction in peak intensity is 0 to 0.2, it is determined that the product is ready for shipment. A method for managing shipment of a curable composition, wherein shipment is to be stopped if the degree of decrease in peak intensity is not 0 to 0.2. [Effects of the Invention]

[0008] According to one embodiment of the present invention, there is provided a method for evaluating the quality of a curable composition, which allows the quality of the curable composition to be evaluated simply and stably. According to one embodiment of the present invention, there is provided a method for managing shipment of a curable composition using the above-described method for evaluating the quality of a curable composition. DETAILED DESCRIPTION OF THE INVENTION

[0009] In the present disclosure, numerical ranges indicated using "to" include the numerical values ​​before and after "to" as the minimum and maximum values, respectively. In the numerical ranges described in stages in this disclosure, the upper or lower limit value described in one numerical range may be replaced by the upper or lower limit value of another numerical range described in stages. The limit values ​​may be replaced by values ​​shown in the examples. In the present disclosure, when a compound or group is represented by a specific formula (X), the compound or group represented by the formula (X) may be referred to as compound (X) or compound X, and group (X) or group X, respectively. In the present disclosure, the term "surface treatment layer" refers to a layer formed on the surface of a substrate by surface treatment with a surface treatment agent. In the present disclosure, "(meth)acrylic" is a general term for acrylic and methacrylic. In the present disclosure, "(poly)siloxane" is a general term for siloxane and polysiloxane.

[0010] [Quality evaluation method for curable compositions] The quality evaluation method of the present disclosure includes a step of detecting, by Raman spectroscopy, peaks attributable to bonds between Si atoms derived from the reactive silyl group and the reactive group in a curable composition containing a compound having a reactive silyl group (hereinafter also referred to as a "specific silane compound") that is contained in a container, and determining whether the degree of decrease in peak intensity, represented by the following formula (1), is 0 to 0.2, where A is the peak intensity when the curable composition is contained in the container, and B is the peak intensity 60 days after the curable composition is contained in the container at 25°C. Peak intensity reduction rate = (peak intensity A - peak intensity B) / (peak intensity A) (1)

[0011] Conventionally, methods for evaluating the quality of a curable composition have been, for example, a method of extracting a portion of the curable composition from a container and measuring the viscosity, and a method of visually evaluating the quality. However, when a method of extracting a portion of the curable composition to measure the viscosity is used, there is a problem that the content volume is reduced by the extraction, making it impossible to ship the product. Also, there is a problem that the evaluation criteria vary when the composition is evaluated visually. In contrast, the quality evaluation method of the present disclosure allows the quality of the curable composition to be evaluated while the curable composition is contained in a container, without extracting a portion of the curable composition from the container, thereby enabling the quality of the curable composition to be evaluated simply and stably.

[0012] <Raman spectroscopy> In the quality evaluation method of the present disclosure, a peak attributed to the bond between the Si atom derived from the reactive silyl group and the reactive group is detected by Raman spectroscopy. Raman spectroscopy is a type of vibrational spectroscopy that uses a laser to irradiate a sample and analyzes the reflected or backscattered radiation. Single-wavelength lasers are commercially available for Raman spectroscopy. Single-wavelength lasers are not particularly limited, but examples include 785 nm red lasers and 532 nm green lasers, with 785 nm being preferred. The laser power is not particularly limited, but examples include 100 to 1,500 mW, with 400 mW being preferred. The energy shift between the measured reflected radiation and the laser line, i.e., the laser wavelength, is equal to the vibrational frequency of the bond in the irradiated molecule. The vibrational frequency depends on the mass of the atoms in the molecule and the strength of the interatomic bonds within the molecule, with different bonds being characterized by specific vibrational frequencies.

[0013] As the analytical device, for example, a Raman spectrometer is used. The Raman spectrometer is preferably a portable Raman spectrometer. By using a portable Raman spectrometer, evaluation can be easily performed at any location.

[0014] The intensity of the peak attributable to the bond between the Si atom derived from the reactive silyl group and the reactive group is calculated, for example, based on the peak derived from the container. For example, if the container is glass, the peak originating from the container is at 300 cm -1 detected nearby. When the reactive group is a methoxysilyl group, the peak attributable to the bond between the Si atom and the reactive group is at 640 cm -1 detected nearby. In the quality evaluation method of the present disclosure, the structure of the compound having a reactive silyl group contained in the container is known in advance, and the peak attributable to the bond between the Si atom and the reactive group can be identified based on the structure of the reactive silyl group.

[0015] In the quality evaluation method of the present disclosure, the peak intensity when the curable composition is placed in a container is defined as peak intensity A, and the peak intensity after 60 days at 25°C from the time the curable composition is placed in the container is defined as peak intensity B. Then, it is determined whether the degree of decrease in peak intensity, represented by the following formula (1), is 0 to 0.2. Peak intensity reduction rate = (peak intensity A - peak intensity B) / (peak intensity A) (1)

[0016] A reduction in peak intensity of 0 to 0.2 means that the quality is maintained 60 days after the curable composition is placed in a container and stored at 25° C. On the other hand, a reduction in peak intensity of more than 0.2 means that the quality is degraded 60 days after the curable composition is placed in a container and stored at 25° C.

[0017] Specifically, after the curable composition is placed in a container, hydrolysis of the specific silane compound contained in the curable composition progresses, which may result in changes such as an increase in viscosity.

[0018] According to the quality evaluation method of the present disclosure, the quality of a curable composition can be evaluated by focusing on the peaks attributable to the bond between the Si atom derived from the reactive silyl group and the reactive group. Specifically, it can be confirmed whether a specific silane compound is stable after being placed in a container.

[0019] <Container> The container for storing the curable composition is not particularly limited as long as it can be analyzed by Raman spectroscopy. Among these, from the viewpoint of ease of handling, the container is preferably made of glass or resin. The container is not limited to being colorless and transparent, and may be colored. Conventionally, colorless and transparent containers have been used for visual evaluation, but the quality evaluation method of the present disclosure can be applied to the quality evaluation of curable compositions stored in a wide variety of containers.

[0020] <Curable composition> The curable composition used in the quality evaluation method of the present disclosure contains a specific silane compound.

[0021] (reactive silyl group) The number of reactive silyl groups contained in the specific silane compound is 1 or more, and from the viewpoint of further improving the abrasion resistance of the surface treatment layer, it is preferably 1 to 18, more preferably 1 to 12, even more preferably 1 to 8, particularly preferably 1 to 6, and extremely preferably 1 to 4. In one embodiment, the number of reactive silyl groups contained in the specific silane compound is preferably 2 to 18, more preferably 2 to 12, even more preferably 2 to 8, and particularly preferably 2 to 6. The number of reactive silyl groups may be 1.

[0022] The reactive silyl group means a group in which a reactive group is bonded to a Si atom. The reactive group is preferably a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group. As described above, in the quality evaluation method of the present disclosure, the degree of decrease in peak intensity is calculated by focusing on the peak attributable to the bond between the Si atom and the reactive group.

[0023] The hydrolyzable group is a group that becomes a hydroxyl group by hydrolysis. 1 The hydrolyzable silyl group represented by the formula (I) undergoes a hydrolysis reaction to become a silanol group represented by Si-OH. The silanol groups then react with each other to form an Si-O-Si bond. The silanol groups can also undergo a dehydration condensation reaction with silanol groups derived from oxides present on the surface of a substrate that is the target of surface treatment, sealing, bonding, etc., to form an Si-O-Si bond.

[0024] Examples of the hydrolyzable group include an alkoxy group, an aryloxy group, a halogen atom, an acyl group, an acyloxy group, an amino group, and -ON=CR. r 2 and an isocyanato group (-NCO). The alkoxy group is preferably an alkoxy group having 1 to 4 carbon atoms. The aryloxy group is preferably an aryloxy group having 3 to 10 carbon atoms. However, the aryl group of the aryloxy group includes a heteroaryl group. The halogen atom is preferably a chlorine atom. The acyl group is preferably an acyl group having 1 to 6 carbon atoms. The acyloxy group is preferably an acyloxy group having 1 to 6 carbon atoms. Rr are each independently an alkyl group having 1 to 10 carbon atoms.

[0025] Examples of the group having a hydrolyzable group include the groups having a hydrolyzable group exemplified above. A -L B is preferred. A is an alkylene group, and L B is a hydrolyzable group. The alkylene group preferably has 1 to 10 carbon atoms. B The hydrolyzable group represented by the formula (I) has the same meaning as the hydrolyzable group described above, and the preferred embodiments are also the same.

[0026] From the viewpoint of ease of production of the compound, the reactive group in the reactive silyl group is preferably an alkoxy group having 1 to 4 carbon atoms or a halogen atom. From the viewpoints of less outgassing during coating and better storage stability of the compound, an alkoxy group having 1 to 4 carbon atoms is preferred, and an ethoxy group or a methoxy group is more preferred.

[0027] The reactive silyl group is preferably a group represented by the following formula (S1). -Si(R 2 ) n L 3-n …(S1)

[0028] In formula (S1), R 2 are each independently a monovalent hydrocarbon group, L's each independently represent a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group; n is an integer of 0 to 2.

[0029] When a molecule contains a plurality of reactive silyl groups, the reactive silyl groups may be the same or different from each other. From the viewpoint of availability of raw materials and ease of production of the compound, it is preferable that the reactive silyl groups are the same.

[0030] R 2are each independently a monovalent hydrocarbon group, preferably a monovalent saturated hydrocarbon group. 2 The number of carbon atoms is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 or 2.

[0031] Each L is independently a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group. Details of the hydrolyzable group and the group having a hydrolyzable group are as described above.

[0032] Among these, from the viewpoint of ease of production of the compound, L is preferably an alkoxy group having 1 to 4 carbon atoms or a halogen atom. L is preferably an alkoxy group having 1 to 4 carbon atoms, more preferably an ethoxy group or a methoxy group, from the viewpoint of less outgassing during coating and better storage stability of the compound.

[0033] n is an integer of 0 to 2, preferably 0 or 1, and more preferably 0. When a plurality of Ls are present, the adhesion of the surface treatment layer to the substrate becomes stronger.

[0034] When n is 1 or less, the plurality of L's present in one molecule may be the same or different from each other. From the viewpoint of availability of raw materials and ease of production of the compound, it is preferable that the plurality of L's are the same. When n is 2, the plurality of R's present in one molecule may be the same or different from each other. 2 may be the same or different from each other. From the viewpoint of availability of raw materials and ease of production of the compound, it is preferable to use a plurality of R 2 are preferably the same.

[0035] From the viewpoint of excellent uniformity and durability of the surface treatment layer, the reactive silyl group is preferably an alkoxysilyl group or a trichlorosilyl group. From the viewpoint of ease of handling of by-products generated in the reaction with the substrate, the reactive silyl group is more preferably an alkoxysilyl group. As the alkoxysilyl group, a dialkoxysilyl group or a trialkoxysilyl group is preferred, and a trialkoxysilyl group is more preferred.

[0036] The reactive silyl group may also be a group represented by the following formula (S2). >SiL2…(S2) L is the same as L in formula (S1).

[0037] The specific silane compound is only required to contain a reactive silyl group, and the structure other than the reactive silyl group is not particularly limited.

[0038] The quality evaluation method of the present disclosure focuses on the peaks attributable to the bond between a Si atom and a reactive group, and can therefore evaluate any compound as long as it contains a reactive silyl group.

[0039] Examples of the specific silane compound include the following compounds. Compound (1): A compound containing at least one selected from the group consisting of a fluoropolyether chain and a polyether chain, and a reactive silyl group. Compound (2): An acrylic polymer containing reactive silyl groups. Compound (3): A compound containing a chain organo(poly)siloxane residue and a reactive silyl group.

[0040] ·Compound (1) In the compound (1), at least one selected from the group consisting of a fluoropolyether chain and a polyether chain may be bonded directly to the reactive silyl group or may be bonded via a linking group.

[0041] Examples of the fluoropolyether chain and polyether chain include a structure represented by formula (P1).

[0042] -(R P1 O) m1 - ...(P1) R P1 are each independently an alkylene group having 1 to 6 carbon atoms which may have a fluorine atom. m1 is an integer of 2 to 500. R P1 When R is an alkylene group, it means a polyether chain. P1When is an alkylene group having a fluorine atom (that is, a fluoroalkylene group), it means a fluoropolyether chain.

[0043] In formula (P1), -(R P1 O) m1 - is preferably represented by the following formula (P2).

[0044] -[(R f1 O) k1 (R f2 O) k2 (R f3 O) k3 (R f4 O) k4 (R f5 O) k5 (R f6 O) k6 ]- …(P2) however, R f1 is an alkylene group having 1 carbon atom which may have a fluorine atom, R f2 is an alkylene group having 2 carbon atoms which may have a fluorine atom, R f3 is an alkylene group having 3 carbon atoms which may have a fluorine atom, R f4 is an alkylene group having 4 carbon atoms which may have a fluorine atom, R f5 is an alkylene group having 5 carbon atoms which may have a fluorine atom, R f6 is an alkylene group having 6 carbon atoms which may have a fluorine atom. k1, k2, k3, k4, k5, and k6 each independently represent an integer of 0 or 1 or more, and k1+k2+k3+k4+k5+k6 is an integer of 2-500.

[0045] k1+k2+k3+k4+k5+k6 is preferably an integer of 2 to 500, more preferably an integer of 2 to 300, still more preferably an integer of 5 to 200, and particularly preferably an integer of 10 to 150.

[0046] In addition, (R f1 O)~(R f6 O) can be bonded in any order. k1 to k6 in formula (P2) are each f1 O)~(R f6 O), not the arrangement. For example, (R f5 O) k5 is (R f5 O), and (R f5 O) k5 Similarly, (R f1 O)~(R f6 The order of the units does not represent the bonding order of the units.

[0047] R f3 ~R f6 In the formula (I), the alkylene group which may have a fluorine atom may be a linear alkylene group, a branched alkylene group, or an alkylene group having a ring structure.

[0048] ·Compound (2) In compound (2), the reactive silyl group may be contained in a structural unit constituting the acrylic polymer, or may be bonded to the main chain terminal of the acrylic polymer. For example, by carrying out polymerization using an acrylic acid ester having a reactive silyl group, an acrylic polymer containing an acrylic acid ester having a reactive silyl group as a constituent unit can be obtained. Alternatively, for example, after introducing an alkenyl group into the main chain terminal of an acrylic polymer, a reactive silyl group can be introduced into the main chain terminal of the acrylic polymer by a hydrosilylation reaction.

[0049] The compound (2) is preferably an acrylic polymer having a reactive silyl group at the end of the main chain.

[0050] Examples of acrylic monomers that constitute acrylic polymers include (meth)acrylic acid, (meth)acrylic acid esters, and (meth)acrylamides. Examples of the (meth)acrylic acid ester include methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, n-pentyl (meth)acrylate, n-hexyl (meth)acrylate, cyclohexyl (meth)acrylate, n-heptyl (meth)acrylate, n-octyl (meth)acrylate, and 2-ethyl (meth)acrylate. hexyl (meth)acrylate, nonyl (meth)acrylate, decyl (meth)acrylate, dodecyl (meth)acrylate, phenyl (meth)acrylate, toluyl (meth)acrylate, benzyl (meth)acrylate, 2-methoxyethyl (meth)acrylate, 3-methoxybutyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, stearyl (meth)acrylate, glycidyl (meth)acrylate, (3-trimethoxysilyl)propyl (meth)acrylate , (3-dimethoxymethylsilyl)propyl (meth)acrylate, (2-trimethoxysilyl)ethyl (meth)acrylate, (2-dimethoxymethylsilyl)ethyl (meth)acrylate, trimethoxysilylmethyl (meth)acrylate, (dimethoxymethylsilyl)methyl (meth)acrylate, ethylene oxide adducts of (meth)acrylic acid, trifluoromethylmethyl (meth)acrylate, 2-trifluoromethylethyl (meth)acrylate, 2-perfluoroethylethyl (meth)acrylate, 2-perfluoroethyl-2-perfluorobutylethyl (meth)acrylate, perfluoroethyl (meth)acrylate, trifluoromethyl (meth)acrylate, bis(trifluoromethyl)methyl (meth)acrylate, 2-trifluoromethyl-2-perfluoroethylethyl (meth)acrylate, 2-perfluorohexylethyl (meth)acrylate, 2-perfluorodecylethyl (meth)acrylate, and 2-perfluorohexadecylethyl (meth)acrylate. Examples of (meth)acrylamides include (meth)acrylamide, N-methyl(meth)acrylamide, N-ethyl(meth)acrylamide, N-propyl(meth)acrylamide, Nn-butyl(meth)acrylamide, Nt-butyl(meth)acrylamide, N-butoxymethyl(meth)acrylamide, N-isopropyl(meth)acrylamide, N-methylol(meth)acrylamide, N,N-dimethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide, and (meth)acryloylmorpholine.

[0051] The acrylic polymer may contain structural units derived from vinyl monomers in addition to acrylic monomers. Examples of vinyl monomers include styrene monomers such as styrene, vinyltoluene, α-methylstyrene, chlorostyrene, and styrenesulfonic acid; Fluorine-containing vinyl monomers such as perfluoroethylene, perfluoropropylene, and vinylidene fluoride; silicon-containing vinyl monomers such as vinyltrimethoxysilane and vinyltriethoxysilane; Maleic anhydride, maleic acid, mono- and dialkyl esters of maleic acid; Fumaric acid, mono- and dialkyl esters of fumaric acid; Maleimide-based monomers such as maleimide, methylmaleimide, ethylmaleimide, propylmaleimide, butylmaleimide, hexylmaleimide, octylmaleimide, dodecylmaleimide, stearylmaleimide, phenylmaleimide, and cyclohexylmaleimide; Nitrile group-containing vinyl monomers such as acrylonitrile and methacrylonitrile; amide group-containing vinyl monomers such as acrylamide and methacrylamide; vinyl ester monomers such as vinyl acetate, vinyl propionate, vinyl pivalate, vinyl benzoate, and vinyl cinnamate; Alkenyl monomers such as ethylene and propylene; Conjugated diene monomers such as butadiene and isoprene; Included are vinyl chloride, vinylidene chloride, allyl chloride, and allyl alcohol. The average number of reactive silyl groups contained in one molecule of the acrylic polymer is preferably from 1.0 to 5.0, more preferably from 1.5 to 3.0. ·Compound (3) In the compound (3), the chain organo(poly)siloxane residue and the reactive silyl group may be bonded directly or via a linking group. The compound (3) may contain one or more linear organo(poly)siloxane residues. When the specific silane compound contains two or more linear organo(poly)siloxane residues, the two or more linear organo(poly)siloxane residues may be the same or different.

[0052] Examples of the chain organo(poly)siloxane residue include chain organo(poly)siloxane residues represented by the following formula (B1).

[0053] [ka]

[0054] In formula (B1), R 3 are each independently a hydrocarbon group, k1 is a number equal to or greater than 1, * indicates the bonding site with the adjacent atom.

[0055] In formula (B1), R 3 Examples of the hydrocarbon group represented by the formula (I) include an aliphatic hydrocarbon group and an aromatic hydrocarbon group. Among them, the hydrocarbon group is preferably an aliphatic hydrocarbon group, and more preferably an alkyl group. The alkyl group may be any of a linear alkyl group, a branched alkyl group, and a cyclic alkyl group, but a linear alkyl group is preferred, and a methyl group, an ethyl group, an n-propyl group, or an n-butyl group is more preferred, and a methyl group is even more preferred. Furthermore, the aromatic hydrocarbon group is preferably a phenyl group.

[0056] In formula (B1), k1 is a number of 1 or more, preferably a number from 1 to 600, more preferably a number from 1 to 500, even more preferably a number from 3 to 500, particularly preferably a number from 9 to 50, extremely preferably a number from 11 to 30, and most preferably a number from 11 to 25.

[0057] From the viewpoint of applications such as surface treatment agents, sealants, and adhesives, the specific silane compound is preferably at least one selected from the group consisting of compounds represented by the following formulas (2A) to (2C).

[0058] R 1 [-Si(R 2 ) n L 3-n ] …(2A) [L 3-n (R 2 ) n Si-]Y 2 [-Si(R 2 ) n L 3-n ] …(2B) [R 1 -] p1 Y 3 [-Si(R 2 ) n L 3-n ] q1 …(2C)

[0059] In formulas (2A) to (2C), R 1 are each independently a monovalent group, Y 2 is a divalent linking group, Y 3 is a (p1+q1)-valent linking group, p1 is an integer equal to or greater than 0, q1 is an integer equal to or greater than 1, p1+q1 is an integer equal to or greater than 3, When p1 is 1, q1 is an integer equal to or greater than 2, R 2 are each independently a monovalent hydrocarbon group, L's each independently represent a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group; Each n is independently an integer of 0 to 2.

[0060] In formulas (2A) to (2C), R 2 , L, and n are R in formula (S1). 2 , L, and n.

[0061] R 1 Examples include alkyl groups, T 1 3M 1 -(where M 1 is Si, Sn, or Ge, and T 1 are each independently a hydrocarbon group or a trialkylsilyloxy group. Examples include a monovalent organo(poly)siloxane residue, a combination of a monovalent organo(poly)siloxane residue and a divalent hydrocarbon group, and a combination of an alkyl group and a divalent organo(poly)siloxane residue. The alkyl group may have a substituent. The substituted alkyl group is preferably a halogenated alkyl group, more preferably a fluoroalkyl group, and even more preferably a perfluoroalkyl group.

[0062] Also, R 1 The alkyl group represented by the formula (I) has an etheric oxygen atom, -C(O)-, -C(O)O-, -OC(O)-, -C(O)N(R d )-, -N(R d )C(O)-, -N(R d )C(O)N(R d )-, -N(R d )C(O)O-, -OC(O)N(R d )-, -SO2N(R d )- or -N(R d )SO2- may be included. d is a hydrogen atom or an alkyl group. If an etheric oxygen atom is present between carbon atoms, R 1 may be a group in which one of the hydroxyl groups of a polyoxyalkylene glycol has been removed.

[0063] Among them, R 1is preferably a group represented by the following formula (T1). R P2 -(R P1 O) m1 -R P3 -R L -R P4 - …(T1)

[0064] In formula (T1), R P1 is an alkylene group having 1 to 6 carbon atoms which may have a fluorine atom. R P3 and R P4 are each independently an alkylene group having 1 to 50 carbon atoms which may have a fluorine atom. m1 is an integer from 2 to 500. R P2 is a hydrogen atom or a fluorine atom. R L -C(O)-, -C(O)O-, -OC(O)-, -C(O)N(R d )-, -N(R d )C(O)-, -N(R d )C(O)N(R d )-, -N(R d )C(O)O-, -OC(O)N(R d )-, -SO2N(R d )- or -N(R d )SO2-. R d is a hydrogen atom or an alkyl group.

[0065] (R P1 O) m1 The preferred embodiments are as described above. R P2 is preferably a fluorine atom. R P3 is preferably a fluoroalkylene group having 1 to 6 carbon atoms, more preferably a perfluoroalkylene group having 1 to 6 carbon atoms. R P4 is preferably an alkylene group having 1 to 6 carbon atoms.

[0066] Also, R 1is preferably a group represented by the following formula (T2). R 51 -B 1 -R 52 -R L -R 53 - …(T2)

[0067] In formula (T2), R 51 is an alkyl group or T 1 3M 1 - and M 1 is Si, Sn, or Ge, T 1 are each independently a hydrocarbon group or a trialkylsilyloxy group. B 1 is a group represented by the above formula (B1). R 52 and R 53 are each independently an alkylene group having 1 to 50 carbon atoms which may have a fluorine atom. R L -C(O)-, -C(O)O-, -OC(O)-, -C(O)N(R d )-, -N(R d )C(O)-, -N(R d )C(O)N(R d )-, -N(R d )C(O)O-, -OC(O)N(R d )-, -SO2N(R d )- or -N(R d )SO2-.

[0068] The preferred embodiments of the group represented by formula (B1) are as described above. R 52 and R 53 are each independently preferably an alkylene group having 1 to 50 carbon atoms, and may be an alkylene group having 1 to 6 carbon atoms.

[0069] Y 2Examples of the alkylene group include an alkylene group. The alkylene group may have a substituent. The alkylene group having a substituent is preferably a halogenated alkylene group, more preferably a fluoroalkylene group, and even more preferably a perfluoroalkylene group.

[0070] Also, Y 2 The alkylene group represented by the formula (I) has an etheric oxygen atom, -C(O)-, -C(O)O-, -OC(O)-, -C(O)N(R d )-, -N(R d )C(O)-, -N(R d )C(O)N(R d )-, -N(R d )C(O)O-, -OC(O)N(R d )-, -SO2N(R d )- or -N(R d )SO2- may be included. d is a hydrogen atom or an alkyl group. If an etheric oxygen atom is present between carbon atoms, Y 2 may be a group obtained by removing two hydroxyl groups from a polyoxyalkylene glycol.

[0071] Y 2 and Y 3 Y may be a residue of a polymer having a structural unit derived from a polymerizable monomer. The polymerizable monomer is preferably a radical polymerizable monomer, more preferably an ethylenically unsaturated monomer, and even more preferably an acrylic acid ester. 2 and Y 3 may be, for example, the residue of an acrylic polymer.

[0072] Y 3 is a trivalent or higher linking group, and preferably contains a branched chain structure or a ring structure.

[0073] Y 3may be a residue of an oxyalkylene polymer. The oxyalkylene polymer can be produced, for example, by ring-opening addition polymerization of an alkylene oxide monomer to a compound having three or more hydroxyl groups. Examples of compounds having three or more hydroxyl groups include glycerin, trimethylolpropane, trimethylolethane, sorbitol, pentaerythritol, and low-molecular-weight polyoxypropylenetriol.

[0074] p1 is an integer of 0 or more, preferably an integer of 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0075] q1 is an integer of 1 or more, preferably an integer of 2 to 10, more preferably 3 to 6, and even more preferably 3. p1+q1 is an integer of 3 or more, preferably an integer of 4 to 10, more preferably 4 to 7, and even more preferably 4.

[0076] Y 3 [-Si(R 2 ) n L 3-n ] q1 The group represented by the following formula (Z1) to (Z4) may be any one of the following formulas (Z1) to (Z4). -(X 33 ) s2 -Q a2 -N[-Q b2 -Si(R 2 ) n L 3-n ]2…(Z1) -Q a3 -Si(R g )[-Q b3 -Si(R 2 ) n L 3-n ]2…(Z2) -[Q e ] s4 -Q a4 -(O) t4 -C[-(O) u4 -Q b4 -Si(R 2 ) n L 3-n ] 3-w1 (-R 31) w1 …(Z3) -Q a5 -Si[-Q b5 -Si(R 2 ) n L 3-n ]3…(Z4)

[0077] In formula (Z1), X 33 -O-, -S-, -N(R d )-, -C(O)-, -C(O)O-, -C(O)S-, -SO2N(R d )-, -N(R d )SO2-, -N(R d )C(O)-, -N(R d )C(O)N(R d )-, -OC(O)N(R d )- or -C(O)N(R d )-; or a combination of these with a divalent linking group. R d is a hydrogen atom or an alkyl group (preferably having 1 to 10 carbon atoms).

[0078] Q a2 represents a single bond, an alkylene group, -C(O)-, or an etheric oxygen atom between carbon atoms of an alkylene group having two or more carbon atoms, -C(O)-, -C(O)O-, -OC(O)-, -C(O)N(R d )-, -N(R d )C(O)-, -N(R d )C(O)N(R d )-, -N(R d )C(O)O-, -OC(O)N(R d )-, -SO2N(R d )-, -N(R d )SO2-, -C(O)N(R d )- or -NH-. Q a2 The alkylene group represented by the following formula (I) preferably has 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, further preferably 1 to 6 carbon atoms, and particularly preferably 1 to 3 carbon atoms. Q a2An etheric oxygen atom is not present between carbon atoms of an alkylene group having two or more carbon atoms, and the alkylene group is represented by -C(O)-, -C(O)O-, -OC(O)-, -C(O)N(R d )-, -N(R d )C(O)-, -N(R d )C(O)N(R d )-, -N(R d )C(O)O-, -OC(O)N(R d )-, -SO2N(R d )-, -N(R d )SO2-, -C(O)N(R d The group having — or —NH— preferably has 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms.

[0079] Q a2 is preferably a single bond in terms of ease of production of the compound.

[0080] Q b2 is an alkylene group or a group having a divalent organo(poly)siloxane residue, an etheric oxygen atom, or -NH- between carbon atoms of an alkylene group having two or more carbon atoms. Q b2 The number of carbon atoms in the alkylene group represented by the formula (I) is preferably 1 to 30, more preferably 1 to 20, and even more preferably 2 to 20, and may be 2 to 10 or 2 to 6. Examples include 2, 3, 8, 9, and 11. The number of carbon atoms may also be 1 to 10. Q b2 The number of carbon atoms in the group having a divalent organo(poly)siloxane residue, an etheric oxygen atom or an —NH— between carbon atoms of the alkylene group having 2 or more carbon atoms, represented by the following formula, is preferably 2 to 10, and more preferably 2 to 6.

[0081] Q b2 As the bond, -CH2CH2CH2- and -CH2CH2OCH2CH2CH2- are preferred in terms of ease of compound production (however, the right side bonds to Si).

[0082] Two [-Q b2 -Si(R 2 )n L 3-n ] may be the same or different.

[0083] In formula (Z2), Q a3 is a single bond or an alkylene group which may have an etheric oxygen atom. a3 is preferably a single bond. The alkylene group which may have an etheric oxygen atom preferably has 1 to 10 carbon atoms, and particularly preferably has 2 to 6 carbon atoms.

[0084] R g is a hydrogen atom, a hydroxyl group, or an alkyl group. R g From the viewpoint of ease of production of the compound, a hydrogen atom or an alkyl group is preferred. The alkyl group preferably has 1 to 10 carbon atoms, more preferably 1 to 4 carbon atoms, and further preferably a methyl group.

[0085] Q b3 is an alkylene group, or a group having an etheric oxygen atom or a divalent organo(poly)siloxane residue between carbon atoms in an alkylene group having two or more carbon atoms. Q b3 The number of carbon atoms in the alkylene group represented by the formula (I) is preferably 1 to 30, more preferably 1 to 20, and even more preferably 2 to 20, and may be 2 to 10 or 2 to 6. Examples include 2, 3, 8, 9, and 11. The number of carbon atoms may also be 1 to 10. Q b3 The number of carbon atoms in the group having an etheric oxygen atom or a divalent organo(poly)siloxane residue between carbon atoms in the alkylene group having 2 or more carbon atoms, represented by the following formula, is preferably 2 to 20, more preferably 2 to 10, and even more preferably 2 to 6. Q b3 is preferably -CH2CH2-, -CH2CH2CH2-, or -CH2CH2CH2CH2CH2CH2CH2CH2CH2- from the viewpoint of ease of production of the compound.

[0086] Two [-Q b3 -Si(R2 ) n L 3-n ] may be the same or different.

[0087] In formula (Z3), Q e is -C(O)O-, -SO2N(R d )-, -N(R d )SO2-, -N(R d )C(O)- or -C(O)N(R d )-; or a combination of these with a divalent linking group. Q e However, -C(O)O-, -SO2N(R d )-, -N(R d )SO2-, -N(R d )C(O)- or -C(O)N(R d )- and a divalent linking group, the divalent linking group is Si(R 3 )2 or Si(R 4 )2. Divalent linking groups include alkylene groups, organo(poly)siloxane residues, polyalkylene oxide groups, and combinations thereof. R 31 is a hydrogen atom, a hydroxyl group, or an alkyl group. When w1 is 1 or 2, R 31 is preferably a hydrogen atom. s4 is 0 or 1. Q a4 is a single bond or an alkylene group which may have an etheric oxygen atom. The alkylene group which may have an etheric oxygen atom preferably has 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, further preferably 1 to 6 carbon atoms, and particularly preferably 1 to 3 carbon atoms. t4 is 0 or 1 (however, Q a4 is a single bond, the value is 0. -Q a4 -(O) t4As -, from the viewpoint of ease of production of the compound, when s4 is 0, a single bond, -CH2O-, -CH2OCH2-, -CH2OCH2CH2O-, -CH2OCH2CH2OCH2-, or -CH2OCH2CH2CH2CH2OCH2- is preferred, and when s4 is 1, a single bond, -CH2-, or -CH2CH2- is preferred.

[0088] Q b4 is an alkylene group, and the alkylene group is —O—, —C(O)N(R d )-(R d The definition of is as described above.) may have a silphenylene skeleton group, a divalent organo(poly)siloxane residue or a dialkylsilylene group. When the alkylene group has an -O- or silphenylene skeleton group, it is preferable that the -O- or silphenylene skeleton group is present between carbon atoms. d )-, dialkylsilylene group or divalent organo(poly)siloxane residue, carbon atom-carbon atom or (O) u4 It is preferable that the group is present at the terminal on the side that bonds to the hydroxyl group. Q b4 The number of carbon atoms in the alkylene group represented by the formula (I) is preferably 1 to 30, more preferably 1 to 20, and even more preferably 2 to 20, and may be 2 to 10 or 2 to 6. Examples include 2, 3, 8, 9, and 11. The number of carbon atoms may also be 1 to 10.

[0089] u4 is 0 or 1. -(O) u4 -Q b4 As -, -CH2CH2-, -CH2CH2CH2-, -CH2OCH2CH2CH2-, -CH2OCH2CH2CH2CH2CH2-, -OCH2CH2CH2-, -OSi(CH3)2CH2CH2CH2-, -OSi(CH3)2OSi(CH3)2CH2CH2CH2-, -CH2CH2CH2Si(CH3)2PhSi(CH3)2CH2CH2- are preferred in terms of ease of production of the compounds (however, the right side is bonded to Si).

[0090] w1 is an integer of 0 to 2, preferably 0 or 1, and more preferably 0. [-(O) u4 -Q b4 -Si(R 2 ) n L 3-n If there are two or more [-(O) u4 -Q b4 -Si(R 2 ) n L 3-n ] may be the same or different. R 31 If there are two or more, two or more (-R 31 ) may be the same or different.

[0091] In formula (Z4), Q a5 is an alkylene group which may have an etheric oxygen atom. The alkylene group which may have an etheric oxygen atom preferably has 1 to 10 carbon atoms, and particularly preferably has 2 to 6 carbon atoms. Q a5 As the group, -OCH2CH2CH2-, -OCH2CH2OCH2CH2CH2-, -CH2CH2-, and -CH2CH2CH2- are preferred in terms of ease of production of the compound (where the right side bonds to Si).

[0092] Q b5 is an alkylene group, or a group having an etheric oxygen atom or a divalent organo(poly)siloxane residue between carbon atoms in an alkylene group having two or more carbon atoms. Q b5 The number of carbon atoms in the alkylene group represented by the formula (I) is preferably 1 to 30, more preferably 1 to 20, and even more preferably 2 to 20, and may be 2 to 10 or 2 to 6. Examples include 2, 3, 8, 9, and 11. The number of carbon atoms may also be 1 to 10. Q b5The number of carbon atoms in the group having an etheric oxygen atom or a divalent organo(poly)siloxane residue between carbon atoms in the alkylene group having 2 or more carbon atoms, represented by the following formula, is preferably 2 to 20, more preferably 2 to 10, and even more preferably 2 to 6. Q b5 As the aryl group, -CH2CH2CH2- and -CH2CH2OCH2CH2CH2- are preferred in terms of ease of compound production (however, if the right side is Si(R 2 ) n L 3-n Binds to.

[0093] Three [-Q b5 -Si(R 2 ) n L 3-n ] may be the same or different.

[0094] Examples of the specific silane compound include compounds described in WO 2009 / 008380, WO 2017 / 022437, WO 2018 / 143433, WO 2018 / 079743, JP 2000-327772, WO 2017 / 038830, JP 2022-75628, JP 2019-206720, and WO 2023 / 017830.

[0095] The number average molecular weight (Mn) of the specific silane compound is preferably 1,000 to 30,000, more preferably 1,000 to 28,000, and even more preferably 1,000 to 27,000. In the present disclosure, the number average molecular weight (Mn) is determined by SEC (Size Exclusion Chromatography) measurement, and polystyrene is used as a standard substance for molecular weight conversion.

[0096] The quality evaluation method disclosed herein focuses on the peaks attributable to bonds between Si atoms and reactive groups, and therefore can be evaluated more accurately when the number-average molecular weight of the specific silane compound is relatively small and the concentration of reactive silyl groups contained in the specific silane compound is high.

[0097] The content of the specific silane compound in the curable composition is not particularly limited, but is preferably 10% by mass or more, more preferably 30% by mass or more, and even more preferably 50% by mass or more. The content of the specific silane compound may be 100% by mass.

[0098] The quality evaluation method of the present disclosure is a method that focuses on the peaks attributable to the bond between the Si atom and the reactive group, and therefore, the higher the content of the specific silane compound, the more accurately the evaluation can be performed.

[0099] The curable composition may contain other components in addition to the specific silane compound. Other components include a solvent.

[0100] The curable composition may contain a solvent for dissolving the specific silane compound from the viewpoints of economy, workability, ease of controlling the thickness of the treated layer, and the like.

[0101] When the curable composition contains a solvent, the content of the solvent in the curable composition is preferably from 60 to 99.999 mass %, more preferably from 80 to 99.99 mass %, and even more preferably from 90 to 99.9 mass %.

[0102] When the curable composition contains a solvent, the content of the specific silane compound in the curable composition is preferably from 0.001 to 40% by mass, more preferably from 0.01 to 20% by mass, and more preferably from 0.1 to 10% by mass.

[0103] Examples of the solvent include compounds consisting only of hydrogen atoms and carbon atoms, and compounds consisting only of hydrogen atoms, carbon atoms, and oxygen atoms. Specific examples include hydrocarbon organic solvents, ketone organic solvents, ether organic solvents, ester organic solvents, glycol organic solvents, and alcohol organic solvents. Specific examples of hydrocarbon organic solvents include pentane, hexane, heptane, octane, hexadecane, isohexane, isooctane, isononane, cycloheptane, cyclohexane, bicyclohexyl, benzene, toluene, ethylbenzene, o-xylene, m-xylene, p-xylene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, n-butylbenzene, sec-butylbenzene, and tert-butylbenzene. Specific examples of the ketone organic solvent include acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, 2-heptanone, 4-heptanone, 3,5,5-trimethyl-2-cyclohexen-1-one, and 3,3,5-trimethylcyclohexanone, and isophorone. Specific examples of the ether-based organic solvent include diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, and 1,4-dioxane. Specific examples of ester-based organic solvents include methyl acetate, ethyl acetate, propyl acetate, isopropyl acetate, butyl acetate, isobutyl acetate, tert-butyl acetate, amyl acetate, isoamyl acetate, ethyl 3-ethoxypropionate, ethyl lactate, ethylene glycol monobutyl ether acetate, diethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether acetate, dipropylene glycol methyl ether acetate, 3-methoxy-3-methylbutyl acetate, 3-methoxybutyl acetate, propylene glycol monomethyl acetate, propylene glycol dimethyl acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monomethyl ether acetate, and diethylene glycol monoethyl ether acetate, cyclohexanol acetate, propylene glycol diacetate, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether propionate, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether acetate, propylene glycol monopropyl ether acetate, propylene glycol diacetate, dipropylene glycol methyl ether acetate, 1,3-butylene glycol diacetate, 1,4-butanediol diacetate, 1,3-butylene glycol diacetate, 1,6-hexanediol diacetate, γ-butyrolactone, triacetin, 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate. Specific examples of glycol-based organic solvents include ethylene glycol, ethylene glycol monobutyl ether, diethylene glycol monobutyl ether, triethylene glycol monobutyl ether, tetraethylene glycol monobutyl ether, ethylene glycol monohexyl ether, diethylene glycol monohexyl ether, ethylene glycol mono-2-ethylhexyl ether, diethylene glycol mono-2-ethylhexyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, propylene glycol monopropyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-tert-butyl ether, ethylene glycol monopropyl ether, ethylene glycol monomethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monobutyl ether, and dipropylene glycol monopropyl ether. Examples of suitable glycol monopropyl ethers include dipropylene glycol monomethyl ether, tripropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, propylene glycol monophenyl ether, 1,3-butylene glycol, propylene glycol n-propyl ether, propylene glycol n-butyl ether, diethylene glycol monoethyl ether, dipropylene glycol n-propyl ether, dipropylene glycol n-butyl ether, tripropylene glycol methyl ether, tripropylene glycol n-butyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, diethylene glycol dibutyl ether, tetraethylene glycol dimethyl ether, dipropylene glycol dimethyl ether pentane, triethylene glycol dimethyl ether, and polyethylene glycol dimethyl ether. Specific examples of alcohol-based organic solvents include methanol, ethanol, 1-propanol, isopropyl alcohol, n-butanol, diacetone alcohol, isobutanol, sec-butanol, tert-butanol, pentanol, 3-methyl-1,3-butanediol, 1,3-butanediol, 1,3-butylene glycol, octanediol, 2,4-diethylpentanediol, butylethylpropanediol, 2-methyl-1,3-propanediol, 4-hydroxy-4-methyl-2-pentanone, 2-ethyl-1-hexanol, 3,5,5-trimethyl-1-hexanol, isodecanol, isotridecanol, 3-methoxy-3-methyl-1-butanol, 2-methoxybutanol, 3-methoxybutanol, cyclohexanol, furfuryl alcohol, tetrahydrofurfuryl alcohol, benzyl alcohol, and methylcyclohexanol. From the viewpoint of suppressing hydrolysis of the specific silane compound, it is preferable that the curable composition contains an alcohol as a solvent.

[0104] Examples of the organic solvent include halogen-based organic solvents, nitrogen-containing compounds, sulfur-containing compounds, siloxane compounds, and fluorine-containing organic solvents.

[0105] Specific examples of halogen-based organic solvents include dichloromethane, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, o-chlorotoluene, m-chlorotoluene, p-chlorotoluene, m-dichlorobenzene, and 1,2,3-trichloropropane.

[0106] Examples of the nitrogen-containing compound include nitrobenzene, acetonitrile, benzonitrile, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and 1,3-dimethyl-2-imidazolidinone.

[0107] Examples of sulfur-containing compounds include carbon disulfide and dimethyl sulfoxide.

[0108] Examples of the siloxane compound include hexamethyldisiloxane, hexaethyldisiloxane, octamethyltrisiloxane, octaethyltrisiloxane, hexamethylcyclotrisiloxane, hexaethylcyclotrisiloxane, octamethylcyclotetrasiloxane, octaethylcyclotetrasiloxane, and decamethyltetrasiloxane.

[0109] The fluorine-containing organic solvents include polyfluoroaromatic hydrocarbons (e.g., 1,3-bis(trifluoromethyl)benzene); polyfluoroaliphatic hydrocarbons (e.g., CF 13 CH2CH3 (e.g., Asahiklin (registered trademark) AC-6000 manufactured by AGC Corporation), 1,1,2,2,3,3,4-heptafluorocyclopentane (e.g., Zeorora (registered trademark) H manufactured by Zeon Corporation); hydrofluoroethers (HFE) (e.g., perfluoropropyl methyl ether (C3F7OCH3) (e.g., Novec (trademark) 7000 manufactured by Sumitomo 3M Limited), perfluorobutyl methyl ether (C4F9OCH3) (e.g., Novec (trademark) 7100 manufactured by Sumitomo 3M Limited), perfluorobutyl ethyl ether (C4F9OC2H5) (e.g., Novec (trademark) 7200 manufactured by Sumitomo 3M Limited), perfluorohexyl methyl ether alkyl perfluoroalkyl ethers (wherein the perfluoroalkyl group and alkyl group may be linear or branched) such as alkyl ether (C2F5CF(OCH3)C3F7) (e.g., Novec™ 7300 manufactured by Sumitomo 3M Limited), CF3CH2OCF2CHF2 (e.g., Asahiklin™ AE-3000 manufactured by AGC Corporation); and hydrofluoroolefins (HFOs) (e.g., 1-chloro-2,3,3-trifluoro-1-propene (HCFO-1233yd) (e.g., Amorea™ AS-300 manufactured by AGC Corporation), Opteon™ SF01, SF05, SF10, SF30, SF33, SF70, SF79, and SF80 manufactured by Chemours).

[0110] (Application) Since the curable composition contains the specific silane compound, it can form a surface treatment layer that is excellent in water repellency and abrasion resistance, and is therefore useful as a surface treatment agent.

[0111] The article to be surface-treated with the surface treatment agent is not particularly limited. The article to be surface-treated may be a medical device or medical material. The article to be surface-treated may also be an automobile interior or exterior component. Examples of exterior components include windows, light covers, and exterior camera covers. Examples of interior components include instrument panel covers, navigation system touch panels, and decorative interior components.

[0112] Among these, the article to be surface-treated is preferably an optical article, that is, the surface treatment agent is preferably used for surface treatment of an optical article.

[0113] The optical article may be an optical material or an optical member.

[0114] Preferred examples of the optical material include optical materials related to displays and the like, as well as a wide variety of other optical materials. Examples of optical materials include displays such as cathode ray tubes (CRTs; for example, personal computer monitors), liquid crystal displays, plasma displays, organic EL displays, inorganic thin-film EL dot matrix displays, rear projection displays, vacuum fluorescent displays (VFDs), and field emission displays (FEDs), as well as protective plates for such displays, and displays whose surfaces have been treated with an anti-reflection film.

[0115] Examples of optical components include car navigation systems, mobile phones, smartphones, digital cameras, digital video cameras, PDAs, portable audio players, car audio, game devices, eyeglass lenses, camera lenses, lens filters, sunglasses, medical devices such as gastroscopes, copiers, PCs, displays (e.g., liquid crystal displays, organic EL displays, plasma displays, touch panel displays), touch panels, protective films, and anti-reflection films.

[0116] Other examples of optical components include front protective plates, antireflection plates, polarizing plates, and antiglare plates for displays such as PDPs and LCDs; disc surfaces of optical discs such as Blu-ray (registered trademark) discs, DVD discs, CD-Rs, and MOs; optical fibers; and the display surfaces of watches and clocks.

[0117] When the article to be surface-treated is an optical component, the material constituting the surface of the article is a material for optical components, such as glass or transparent plastic. Furthermore, when the article to be surface-treated is an optical component, a functional layer such as a hard coat layer or an antireflection layer may be formed on the surface (outermost layer) of the article. The antireflection layer may be either a single-layer antireflection layer or a multi-layer antireflection layer. Examples of inorganic substances that can be used in the antireflection layer include SiO2, SiO, ZrO2, TiO2, TiO, Ti2O3, Ti2O5, Al2O3, Ta2O5, Ta3O5, Nb2O5, HfO2, Si3N4, CeO2, MgO, Y2O3, SnO2, MgF2, and WO3. These inorganic substances may be used alone or in combination (e.g., as a mixture) of two or more of them. When a multilayer antireflection layer is used, it is preferable to use SiO2 and / or SiO for the outermost layer. When the article to be surface-treated is an optical glass component for a touch panel, a transparent electrode, such as a thin film using indium tin oxide (ITO) or indium zinc oxide, may be present on a portion of the surface of the article. In addition, the article may have an insulating layer, an adhesive layer, a protective layer, a decorative frame layer (I-CON), an atomization film layer, a hard coating film layer, a polarizing film, a phase difference film, a liquid crystal display module, or the like, depending on its specific specifications.

[0118] In particular, the article to be surface-treated is preferably a display or a touch panel.

[0119] Furthermore, since the curable composition contains a specific silane compound, the resulting cured product has excellent modulus, strength, and elongation. Therefore, the curable composition is suitable for use as an adhesive, a sealant (e.g., elastic sealant for construction, sealant for double-glazing, anti-rust and waterproof sealant for glass edges, sealant for the back surface of solar cells, sealant for buildings, sealant for ships, sealant for automobiles, and sealant for roads), or an electrical insulating material (insulating coating material for electric wires and cables).

[0120] [Shipping management method for curable compositions] The shipping management method of the present disclosure performs an evaluation using the above-mentioned quality evaluation method, and determines that shipping is possible if the degree of decrease in peak intensity is 0 to 0.2, and determines that shipping should be suspended if the degree of decrease in peak intensity is not 0 to 0.2.

[0121] Details of the quality evaluation method in the shipping management method of the present disclosure are as described above. In the shipping management method of the present disclosure, when the degree of decrease in peak intensity is 0 to 0.2 as a result of evaluation using the quality evaluation method, it is determined that the product is ready for shipping. As a result, for example, the container containing the curable composition is moved to an area where products are waiting to be shipped. On the other hand, when the degree of decrease in peak intensity is not 0 to 0.2 (i.e., exceeds 0.2), it is determined that shipping is to be suspended. As a result, for example, the container containing the curable composition is moved to a disposal area.

[0122] A label bearing, for example, a lot number is attached to the container in which the curable composition is stored. Data on the evaluation results obtained by the quality evaluation method may be stored, and the data stored in the IC tag of each container may be read to move the container to an area awaiting shipment or a disposal area. [Example]

[0123] The present invention will be explained in more detail below using examples, but the present invention is not limited to these examples.

[0124] [Synthesis of Compound A1] Compound A1 was synthesized according to the method described in Example 2 of WO 2009 / 008380. The average repeat number n was 7.3. CF3O[CF2CF2O] n CF2C(O)NH(CH2)3Si(OCH3)3…(A1)

[0125] [Synthesis of Compound A2] Compound A2 was synthesized according to the method described in Synthesis Example 1 of JP-A-2022-75628. Compound A2 is a compound having a dimethoxymethylsilyl group at the end of a polyoxypropylene chain. Compound A2 has a mass-average molecular weight of 26,300, a number-average molecular weight of 24,300, and an average number of dimethoxymethylsilyl groups per molecule of 1.5.

[0126] [Synthesis of Compound A3] Compound A3 was synthesized according to the method described in Synthesis Example 3 of JP 2019-206720 A. Compound A3 is an acrylic polymer having a dimethoxymethylsilyl group at the end of its main chain, which has a structural unit derived from ethyl acrylate, a structural unit derived from butyl acrylate, and a structural unit derived from stearyl acrylate. Compound A3 has an average number of dimethoxymethylsilyl groups per molecule of 2.0.

[0127] [Synthesis of Compound A4] Compound A4 was synthesized according to the method described in Example 1 of WO 2023 / 017830. The average repeat number n was 19. (CH3)3(Si(CH3)2-O) n -Si(CH3)2-(CH2) 10 -C(O)NH-CH2C{CH2CH2CH2Si(OCH3)3}3…(A4)

[0128] [Quality Evaluation] 10 g of each of Compounds A1 to A4 was placed in a 10 mL borosilicate glass container (thickness: 1 mm), and the water content was adjusted to the value shown in Table 1 to prepare a quality evaluation sample.

[0129] <Quality Evaluation 1 (Raman Spectroscopy)> After shaking the container, the curable composition contained in the container was subjected to Raman spectroscopy from the outside of the container. The peaks attributable to the bond between the Si atom derived from the reactive silyl group and the reactive group were detected, and the peak intensity A was calculated. In addition, after storing the container containing the quality evaluation sample at 25°C for 60 days, the peak attributable to the bond between the Si atom derived from the reactive silyl group and the reactive group was detected, and the peak intensity B was calculated. The analysis method is as follows.

[0130] Analytical equipment: Portable Raman spectrometer BRAVO (manufactured by Bruker) Laser wavelength: 785nm Output: 400mW

[0131] Peak intensity A and peak intensity B are measured at 300 cm -1 Based on the peak originating from the container detected near 640 cm -1 The intensity of the peak detected near the center of the graph was determined as the intensity of the peak attributed to the bond between a Si atom and a methoxy group.

[0132] The reduction in peak intensity was calculated based on the following formula, and quality was evaluated. Peak intensity reduction rate = (peak intensity A - peak intensity B) / (peak intensity A)

[0133] <Quality Evaluation 2 (Viscosity Measurement Method)> After shaking the container, a portion of the quality evaluation sample was taken out and the viscosity A was measured. In addition, after the container containing the quality evaluation sample was stored at 25°C for 60 days, a portion of the quality evaluation sample was extracted and the viscosity B was measured. The analysis method is as follows.

[0134] Analytical equipment: E-type viscometer RE-215H (manufactured by Toki Sangyo Co., Ltd.) Measurement temperature: 25℃

[0135] The degree of increase in viscosity was calculated based on the following formula, and quality was evaluated. Viscosity increase = (Viscosity B - Viscosity A) / (Viscosity A)

[0136] The evaluation results are shown in Table 1. In Table 1, when the degree of decrease in peak intensity was 0 to 0.2, it was determined that the product was ready for shipment and was marked with "Y." When the degree of decrease in peak intensity was not 0 to 0.2, it was determined that shipment should be suspended and was marked with "N."

[0137] [Table 1]

[0138] As shown in Table 1, in quality evaluation 1 using Raman spectroscopy, it was found that the quality of the curable composition can be easily and stably evaluated by detecting the peak attributable to the bond between the Si atom derived from the reactive silyl group and the reactive group and calculating the degree of decrease in peak intensity. Furthermore, Quality Evaluation 2 cannot be used as a shipping control method because it requires removing the sample from the container, but it has been known as a method for quantitatively evaluating the quality of a curable composition. Although Quality Evaluation 1 was evaluated from the outside of the container, results correlated with Quality Evaluation 2 were obtained, and it was found that it can be used as a shipping control method.

Claims

1. detecting a peak attributable to a bond between a Si atom derived from the reactive silyl group and the reactive group by Raman spectroscopy in a curable composition that contains a compound having a reactive silyl group and that is contained in a container; The intensity of the peak when the curable composition is placed in a container is defined as peak intensity A, When the intensity of the peak after 60 days at 25°C from the time the curable composition was placed in a container was defined as peak intensity B, A method for evaluating the quality of a curable composition, comprising a step of determining whether or not a degree of decrease in peak intensity represented by the following formula (1) is 0 to 0.2: Peak intensity reduction rate=(peak intensity A−peak intensity B) / (peak intensity A) (1)

2. The method for evaluating the quality of a curable composition according to claim 1, wherein the compound having a reactive silyl group is at least one selected from the group consisting of the following compounds (1) to (3): Compound (1): A compound containing at least one selected from the group consisting of a fluoropolyether chain and a polyether chain, and a reactive silyl group. Compound (2): An acrylic polymer containing a reactive silyl group. Compound (3): A compound containing a chain organo(poly)siloxane residue and a reactive silyl group.

3. The method for evaluating the quality of a curable composition according to claim 1, wherein the compound having a reactive silyl group is at least one selected from the group consisting of compounds represented by the following formulas (2A) to (2C): R 1 [-Si(R ２ ) ｎ L ３－ｎ ] …(2A) [L ３－ｎ (R ２ ) ｎ Si-]Y ２ [-Si(R ２ ) ｎ L ３－ｎ ] …(2B) [R 1 -] ｐ１ Y ３ [-Si(R ２ ) ｎ L ３－ｎ ] ｑ１ …(2) In formulas (2A) to (2C), R １ are each independently a monovalent group, Y ２ is a divalent linking group, Y ３ is a (p1+q1)-valent linking group, p1 is an integer equal to or greater than 0, q1 is an integer of 1 or more, p1+q1 is an integer of 3 or more, R ２ are each independently a monovalent hydrocarbon group, L's each independently represent a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group; Each n is independently an integer of 0 to 2.

4. The method for evaluating the quality of a curable composition according to claim 1 , wherein the curable composition further contains a solvent.

5. The method for evaluating the quality of a curable composition according to claim 1 , wherein the container is made of glass or resin.

6. The method for evaluating the quality of a curable composition according to claim 1 , wherein the curable composition is a surface treatment agent.

7. The method for evaluating the quality of a curable composition according to claim 6 , wherein the surface treatment agent is used for treating the surface of an optical article.

8. The method for evaluating the quality of a curable composition according to claim 7 , wherein the optical article is a touch panel or a display.

9. The method for evaluating the quality of a curable composition according to claim 1 , wherein the curable composition is a sealant or an adhesive.

10. The method for evaluating the quality of a curable composition according to claim 1 , wherein the peak is detected using a portable Raman spectrometer.

11. The quality of a curable composition is evaluated by the quality evaluation method according to any one of claims 1 to 10, If the degree of decrease in peak intensity is 0 to 0.2, it is determined that the product is ready for shipment; The method for managing shipment of a curable composition includes determining that shipment should be suspended if the degree of decrease in peak intensity is not within a range of 0 to 0.2.

Images