JP7387171B2 - Moisture curable composition - Google Patents

Description

The present invention relates to moisture-curable compositions.

Moisture-curable compositions useful as adhesives and sealants that have a crosslinkable, hydrolyzable, silicon-containing group with a main chain of polyether, polyester, or a polymer of ethylenically unsaturated compounds or diene compounds. Those using an organic polymer as a main component are known. These organic polymers having a hydrolyzable silicon-containing group are cured by causing the hydrolyzable silicon-containing group to be hydrolyzed by atmospheric moisture at room temperature in the presence of a catalyst to form a siloxane bond. A curable composition using this organic polymer having a hydrolyzable silicon-containing group has excellent curability, storage stability, weather resistance, and the like.

As the curing catalyst for the organic polymer having a hydrolyzable silicon-containing group, tin(II) dicarboxylate compounds such as tin 2-ethylhexanoate and tin n-octylate, and organic tin compounds such as dibutyltin dilaurate and dibutyltin maleate are used. (IV) compounds and other metal compounds such as iron naphthenate and lead octylate. Among them, organic tin (IV) compounds and tin (II) dicarboxylate compounds are widely used because they have excellent curing speed and curing properties.

Special Publication No. 61-60867 Japanese Patent Application Publication No. 2002-285018

Since all organic tin compounds have a large effect on the environment and the human body, sufficient care must be taken when using them.

In addition, tin compounds such as bis(2-ethylhexanoate) tin and bis(n-octylic acid) tin are used in two-component modified silicone resin sealants (types in which the main ingredient and curing agent are mixed and applied immediately before application). When a compound is used (for example, Patent Document 1), there are major design problems such as residual tack (thin layer uncured phenomenon) occurring due to insufficient curing of the thin layer of the sealant when the sealant is applied. . As a means to solve this problem, it has been proposed to use a tertiary carboxylic acid tin compound such as tin neodecanoate as a curing catalyst (Patent Document 2), but it has not been possible to solve the problem.

Therefore, in view of the above-mentioned prior art, an object of the present invention is to provide a moisture-curable composition that can solve the problem of uncured thin layers.

According to the present invention, there is provided a moisture-curable composition containing a polymer [A] having a reactive hydrolyzable silicon-containing group, a tin dicarboxylate compound [B], and an alcohol [C], A moisture-curable composition is provided in which the tin acid compound [B] is represented by the chemical formula (1), and the alcohol [C] is represented by the chemical formulas (2) to (7).

As a result of intensive research, the present inventors discovered that the problem of thin uncured layers could be solved by using a moisture-curable resin composition containing components [A] to [C], and the present invention I was able to complete it.

The present invention will be explained in detail below.

1. Polymer [A]
The polymer [A] has at least one reactive hydrolyzable silicon-containing group per molecule at the molecular terminal or side chain. The reactive hydrolyzable silicon-containing group may be present at the terminal end of the polymer [A] molecule, or may be present at the side chain, or may be present at both the terminal end and the side chain. It is sufficient that there is at least one reactive hydrolyzable silicon-containing group per molecule of the polymer [A], but from the viewpoint of curing speed and cured physical properties, it is preferable that the number of reactive hydrolyzable silicon-containing groups is 1.5 or more per molecule on average. is preferred. Any known method can be used to bond the reactive hydrolyzable silicon-containing group to the main chain polymer.

A reactive hydrolyzable silicon-containing group is a group having a silicon atom bonded to a hydrolyzable group (e.g., halogen, alkoxy, alkenyloxy, acyloxy, amino, aminooxy, oxime, amide) or a reactive group consisting of a hydroxyl group. It has the property of causing a condensation reaction in the presence of moisture or a crosslinking agent, using a catalyst as necessary. Specific examples include a halogenated silyl group, an alkoxysilyl group, an alkenyloxysilyl group, an acyloxysilyl group, an aminosilyl group, an aminooxysilyl group, an oximesilyl group, and an amidosilyl group.

Here, the number of reactive hydrolyzable groups bonded to one silicon atom is selected from the range of 1 to 3. Further, the number of reactive hydrolyzable groups bonded to one silicon atom may be one or more than one. Further, a reactive hydrolyzable group and a non-reactive hydrolyzable group may be bonded to one silicon atom, or a hydrolyzable group and a hydroxyl group may be bonded to one silicon atom. As the reactive hydrolyzable silicon-containing group, an alkoxysilyl group (including a monoalkoxysilyl group, a dialkoxysilyl group, and a trialkoxysilyl group) is particularly preferable because it is easy to handle.

Among the alkoxysilyl groups described above, trialkoxysilyl groups are preferred because they have high activity and provide good curability, and the resulting cured product has excellent restorability, durability, and creep resistance. On the other hand, dialkoxysilyl groups and monoalkoxysilyl groups are preferable because they have excellent storage stability and the obtained cured products have high elongation and high strength.
It is preferable to use a polymer [A] whose reactive hydrolyzable silicon-containing group is a dialkoxysilyl group and a polymer [A] whose reactive hydrolyzable silicon-containing group is a trialkoxysilyl group in combination to balance the physical properties and curability of the cured product. .

Examples of the polymer [A] include organic polymer [A1] and organopolysiloxane [A2].

(Organic polymer [A1])
The main chain of the organic polymer [A1] used in the present invention is one having a carbon atom, such as alkylene oxide polymer, polyester polymer, ether/ester block copolymer, polymer of ethylenically unsaturated compound, diene Examples include polymers of type compounds.

As the alkylene oxide polymer,
[CH ₂ CH ₂ O] _n
[CH( _CH3 ) _CH2O ] _n
[CH(C ₂ H ₅ )CH ₂ O] _n
[CH ₂ CH ₂ CH ₂ CH ₂ O] _n
Examples include those having one or more types of repeating units such as. Here, n is the same or different integer of 2 or more. These alkylene oxide polymers may be used alone or in combination of two or more. Furthermore, a copolymer containing two or more of the above repeating units can also be used.

Examples of polyester polymers include carboxylic acids such as acetic acid, propionic acid, maleic acid, phthalic acid, citric acid, pyruvic acid, and lactic acid, their anhydrides, their intramolecular and/or intermolecular esters, and substituted products thereof. Examples include those having repeating units.

Examples of the ether-ester block copolymer include those having as repeating units both the repeating unit used in the above-mentioned alkylene oxide polymer and the repeating unit used in the above-mentioned polyester polymer.

Examples of polymers of ethylenically unsaturated compounds and diene compounds include homopolymers of ethylene, propylene, acrylic esters, methacrylic esters, vinyl acetate, acrylonitrile, styrene, isobutylene, butadiene, isoprene, chloroprene, etc. Copolymers of two or more of these may be mentioned. More specifically, polybutadiene, styrene-butadiene copolymer, acrylonitrile-butadiene copolymer, ethylene-butadiene copolymer, ethylene-propylene copolymer, ethylene-vinyl acetate copolymer, ethylene-(meth)acrylic acid Ester copolymer, polyisoprene, styrene-isoprene copolymer, isobutylene-isoprene copolymer, polychloroprene, styrene-chloroprene copolymer, acrylonitrile-chloroprene copolymer, polyisobutylene, polyacrylic acid ester, polymethacrylic acid Examples include esters. These may be used alone or in combination of two or more.

As the organic polymer [A1], an organic polymer having a polar group such as a nitrogen-containing characteristic group in the molecule can also be used. Specific examples of the nitrogen-containing characteristic groups mentioned above include (thio)urethane groups, allophanate groups, other N-substituted urethane groups, bonding groups derived from (thio)urethane groups such as N-substituted allophanate groups, (thio)urea groups, Biuret group, other N-substituted urea groups, N,N'-substituted urea groups, N-substituted biuret groups, bonding groups derived from (thio)urea groups such as N,N'-substituted biuret groups, amide groups, Examples include, but are not limited to, nitrogen-containing characteristic groups such as bonding groups derived from amide groups such as N-substituted amide groups, bonding groups derived from imino groups, (thio)ester groups, (thio)ether groups, etc. Not that it will be done. Among these, nitrogen-containing characteristic groups are preferable because of their high curability, and bonding groups derived from (thio)urethane groups and bonding groups derived from (thio)urea are more preferable from the viewpoint of ease of synthesis. Further, the organic polymer [A1] may contain only one nitrogen-containing characteristic group, or may contain a plurality of one or more kinds of nitrogen-containing characteristic groups. Here, the notation of "(thio)" and "N-substituted" is the same as above.

When the organic polymer [A1] contains a polar group such as the nitrogen-containing characteristic group described above, the toughness of the cured product is improved, and the curability and adhesive strength are also increased. In particular, when the crosslinkable silicon group is connected to the main chain via a polar group such as a nitrogen-containing characteristic group, the curability is further enhanced. The reason for this is that the polar groups of the nitrogen-containing characteristic groups are strongly attracted to each other due to interactions such as hydrogen bonds. It is thought that the polar groups of the nitrogen-containing characteristic groups are strongly attracted to each other, and the molecules of the curable resin are also strongly bonded to each other (forming domains), thereby developing toughness in the cured product. In addition, when the crosslinkable silicon groups are connected to the main chain via a polar group such as a nitrogen-containing characteristic group, when the nitrogen-containing characteristic groups form domains, the crosslinkable silicon groups also come close to each other. This is thought to improve the probability of contact between the crosslinkable silicon groups, and further improve the condensation reactivity between the crosslinkable silicon groups due to catalytic curing by the polar group in the nitrogen-containing characteristic group.

Such an organic polymer [A1] (modified silicone polymer) can be produced by a known method such as the method described in Japanese Patent Publication No. 61-18569, or it can be produced by a commercially available method. . Commercially available products include, for example, the Kaneka MS Polymer series (MS Polymer S203, MS Polymer S303, MS Polymer S903, MS Polymer S911, MS Polymer SAX520, etc.) manufactured by Kaneka Corporation, Cylyl Series (Silyl Polymer SAT200, Cylyl Polymer SAT200, Cylyl Polymer SAX520, etc.) Polymer MA430, Cylyl Polymer MAX447, etc.), MA series, SA series, OR series; ES series (ES-GX3440ST, etc.) manufactured by Asahi Glass Co., Ltd., ESGX series, etc. are exemplified.

The number average molecular weight of the organic polymer [A1] used in the present invention is not particularly limited; The following are desirable. Such an organic polymer can be produced by a known method, but commercially available products such as the above-mentioned Kaneka MS Polymer manufactured by Kaneka Corporation may also be used.

(Organopolysiloxane [A2])
The organopolysiloxane [A2] used in the present invention has a main chain composed of a siloxane bond represented by Si--O, and an organic group is further bonded to the silicon atom constituting the siloxane bond. Examples of such organic groups include alkyl groups such as methyl, ethyl, propyl, and butyl; cycloalkyl groups such as cyclohexyl; alkenyl groups such as vinyl, isopropenyl, and substituted vinyl; allyl groups, crotyl, methallyl, etc. substituted allyl groups; aryl groups such as phenyl, tolyl, and xylyl; aralkyl groups such as benzyl and phenylethyl; and groups in which all or part of the hydrogen atoms of these organic groups are substituted with halogen atoms, such as chloromethyl groups, Examples include 3,3,3-trifluoropropyl group.

As organopolysiloxane [A2],
(-Si(R) ₂ -O-) _m
(In the formula, R is the same or different and represents an organic group, and m represents an integer of 2 or more.)
Examples include those having a repeating unit represented by: As a specific example,
(-Si(CH ₃ ) ₂ -O-) _m
(-Si(C ₂ H ₅ ) ₂ -O-) _m
(-Si(Ph) ₂ -O-) _m
(-Si(-CH=CH ₂ ) ₂ -O-) _m
Examples include those having one or more types of repeating units such as. Here, m are the same or different integers of 2 or more. Organopolysiloxane [A2] may be composed of a single main chain, or may be composed of two or more types of main chains.

The organopolysiloxane may be linear or branched, including trifunctional (R'SiO _1.5 ) or tetrafunctional (SiO ₂ ). Furthermore, depending on the physical properties and use of the cured product, a difunctional type (R' ₂ SiO) or a monofunctional type (R' ₃ SiO _0.5 ) may be combined as necessary (here, R' is an organic group). ). Furthermore, the hydrolyzable silicon-containing group may be bonded either at the end of the molecule or in the middle of the molecular chain.
Incidentally, organopolysiloxane is generally represented by the average compositional formula R _a SiO _4-a/2 (for example, JP-A No. 2005-194399, JP-A No. 8-151521, etc.). The above notation follows this.

There is no particular restriction on the viscosity of the organopolysiloxane [A2] used in the present invention, but one with an excessively high viscosity may reduce workability or impair the physical properties of the cured product obtained. The viscosity at °C is preferably in the range of 0.025 to 100 Pa·s. Such organopolysiloxanes can be manufactured by known methods, including the Tosseal series manufactured by GE Toshiba Silicone Co., Ltd., the sealant series manufactured by Shin-Etsu Chemical Co., Ltd., and the sealant series manufactured by Toray Dow Corning Co., Ltd. Commercially available products such as the SH series can be used.

2. Tin dicarboxylate compound [B]
The tin dicarboxylate compound [B] used in the present invention is represented by the chemical formula (1).
(In the formula, R ¹ , R ² , and R ³ are each a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and may be the same or different from each other.)

In the formula, the alkyl group having 1 to 10 carbon atoms represented by R ¹ , R ² , and R ³ includes, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, Examples include hexyl, heptyl, octyl, ethylhexyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, and the like. Specifically, the number of carbon atoms is, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, and is within the range between any two of the numerical values exemplified here. Good too.

Specific examples of the tin dicarboxylate compound [B] include tin diacetate, tin dipivalate, tin bis(2-ethylbutyrate), tin bis(2-ethylhexanoate), tin bis(n-octylate), and tin bis(n-octylate). Tin (neononanoate), tin bis(isononanoate), tin bis(neodecanoate), tin dilaurate, tin distearate, tin bis(2-ethylhexanoate), tin bis(isononanoate), tin Tin (neodecanoate) is preferred. These tin dicarboxylic acid compounds may be used alone or in combination of two or more.

The tin dicarboxylate compound [B] can be produced by a known method. For example, it can be produced by heating 2 moles of dicarboxylic acid and about 1 mole of stannous chloride in a solvent at a temperature of about 30 to 70° C. in the presence of about 2 moles of an alkali compound. As the raw material dicarboxylic acid, one type of corresponding dicarboxylic acid or a mixture of two or more types may be used. Commercially available products can also be used, such as 2-ethylhexanoic acid, isononanoic acid, neodecanoic acid PG, and Versatic 10.

In the present invention, the proportion of the tin dicarboxylate compound [B] to 100 parts by weight of the polymer [A] is preferably 0.1 to 20 parts by weight, particularly 1 to 10 parts by weight. When it is within the above range, it is excellent in improving curing performance and surface tack, and is also excellent in terms of physical properties and stability of the cured product. Specifically, this proportion is, for example, 0.1, 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, 20 parts by mass, and the It may be within a range between any two values.

3. Alcohol [C]
Alcohol [C] used in the present invention is represented by chemical formulas (2) to (7).

H _k -C-R ⁴ _4-K (2)
(In the formula, R ⁴ is -(CH ₂ ) _m -OH, m is 0 to 3, and may be the same or different from each other. k is 0 or 1. )

N-R ⁵ ₃ (3)
(In the formula, R ⁵ is -(CH ₂ ) _n -OH, and n is 1 to 3 and may be the same or different.)

(In the formula, R ⁶ is -(CH ₂ ) _p -OH, p = 0 to 2, and may be the same or different. A is an oxygen atom or a carbon atom .)

(In the formula, R ⁷ is a hydrogen atom, a hydroxyl group, or a hydrocarbon group, and may be the same or different.)

In the formula, examples of the hydrocarbon group represented by R ⁷ include a methyl group, an ethyl group, a propyl group, an isopropyl group, and a tertiary-butyl group.

Specific examples of alcohol [C] include:
Examples of the compound represented by Chemical Formula 2 include glycerin, pentaerythritol, and the like.
Examples of the compound represented by Chemical Formula 3 include triethanolamine and the like.
Examples of the compound represented by Chemical Formula 4 include inositol, glucose, and galactose.
Examples of the compound represented by Formula 5 include 4-tert-butylcatechol, pyrogallol, and hydroxynol.

Among the alcohols [C], 4-tert-butylcatechol, ascorbic acid, pyrogallol, hydroxyquinol, dithranol, triethanolamine, glycerin, and inositol are preferred, and 4-tert-butylcatechol is more preferred.

In the present invention, the ratio of alcohol [C] to tin dicarboxylate compound [B] is preferably 0.1 to 2.0% by mass, particularly 0.5 to 1.5% by mass. When it is within the above range, it is possible to dissolve it in advance in the tin dicarboxylate compound [B], which is advantageous in that poor dispersion of the alcohol [C] can be prevented. Specifically, this ratio is, for example, 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1.0, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2.0% by mass, and the numerical values exemplified here It may be within the range between any two.

4. Other Additives In addition to the above-mentioned components, the moisture-curable composition of the present invention further contains a curing accelerator, a filler, an adhesion promoter, a colorant, a plasticizer, a curing retarder, an anti-sagging agent, and an anti-aging agent. Various additives commonly added to curable compositions, such as ultraviolet absorbers, radical chain inhibitors, peroxide decomposers, and solvents, can be blended.

Examples of the curing accelerator include butylamine, octylamine, laurylamine, n-hexadecylamine, dibutylamine, monoethanolamine, diethanolamine, triethanolamine, diethylenetriamine, triethylenetetramine, oleylamine, cyclohexylamine, benzylamine, diethylamino. Propylamine, xylylenediamine, triethylenediamine, polyoxyethylenediamine, polyoxypropylenediamine, guanidine, diphenylguanidine, 2,4,6-tris(dimethylaminomethyl)phenol, morpholine, N-methylmorpholine, 2-ethyl-4 -Methylimidazole, 1,8-diazabicyclo(5.4.0)undecene-7 (DBU) and other amine compounds. These amine compounds may be used alone or in combination of two or more.
The amount of the curing accelerator used is preferably 1 to 200 parts by weight, particularly preferably 10 to 100 parts by weight, based on 100 parts by weight of the tin dicarboxylate compound [B]. When it is within the above range, there is a tendency that the curing accelerating effect is sufficiently exhibited, workability is improved, and surface tack after curing is reduced.

Specifically, fillers include calcium carbonate, kaolin, talc, fumed silica, precipitated silica, anhydrous silicic acid, hydrated silicic acid, clay, calcined clay, glass, bentonite, organic bentonite, shirasu balloon, and glass fiber. , asbestos, glass filament, ground quartz, diatomaceous earth, aluminum silicate, aluminum hydroxide, zinc oxide, magnesium oxide, titanium dioxide, and the like.
The amount of filler used varies widely depending on the use of the cured product and the required performance, but for example, it is 10 to 300 parts by mass of the polymer [A] having a reactive hydrolyzable silicon-containing group. It is appropriately selected from a range of about parts by mass.

As the adhesion promoter, various known amino group-substituted alkoxysilane compounds or condensates thereof can be blended. Specifically, γ-aminopropyltrimethoxysilane, γ-aminopropyltriethoxysilane, N -(trimethoxysilylpropyl)ethylenediamine, δ-aminobutyl(methyl)diethoxysilane, N,N'-bis(trimethoxysilylpropyl)ethylenediamine, and partial hydrolysates thereof. Furthermore, to improve adhesion to the substrate, vinyl alkoxysilane compounds such as vinyltriethoxysilane, vinyltrimethoxysilane, and vinyltriisopropoxysilane can be used.

Specific examples of the coloring agent include iron oxide, carbon black, phthalocyanine blue, and phthalocyanine green.

Examples of plasticizers include phthalate esters such as dibutyl phthalate, dioctyl phthalate, diisononyl phthalate, and butylbenzyl phthalate, dioctyl adipate, dioctyl succinate, diisodecyl succinate, diisodecyl sebacate, and butyl oleate. Aliphatic carboxylic acid esters, esters of polyol compounds such as pentaerythritol ester, phosphoric acid esters such as trioctyl phosphate and tricresyl phosphate, epoxidized soybean oil, epoxy plasticizers such as benzyl epoxy stearate, chlorinated Examples include paraffin.

Specific examples of the anti-sagging agent include hydrogenated castor oil, anhydrous silicic acid, organic bentonite, and colloidal silica.

The moisture-curable composition of the present invention is cured by moisture-curing under a normal environmental atmosphere. The pot life of the curing catalyst in the curing treatment is preferably 1 hour or more, more preferably 1 to 8 hours, from the viewpoint of on-site construction. In the present invention, by using the tin dicarboxylate compound [B], it is possible to set the pot life to 1 hour or more, and the stickiness of the surface can be eliminated within a short period of time.

The moisture-curable composition of the present invention usually consists of a main component containing the above-mentioned reactive hydrolyzable silicon-containing group-containing polymer [A] and a curing catalyst component containing the tin dicarboxylate compound [B]. Used as a two-component curable composition. Of course, it can be used as a one-component curable composition.

The moisture-curable composition of the present invention can be used as a sealant, a coating agent, an elastic adhesive, and the like.

EXAMPLES Hereinafter, the present invention will be specifically explained based on Examples, but the scope of the present invention is not limited thereby.

1. Production example of tin dicarboxylate compound <Production example 1 (tin bis(2-ethylhexanoate B-1))>
Weighed 288.4 g (2 mol) of 2-ethylhexanoic acid and 166.7 g (sodium hydroxide: 2 mol) of a 48% aqueous sodium hydroxide solution into a 1000 ml eggplant flask equipped with a nitrogen inlet tube, and stirred with a magnetic stirrer. After thorough mixing, 225 g (1 mol) of stannous chloride was added and reacted at 60°C for 20 minutes. The reaction mixture was extracted with toluene and concentrated under reduced pressure to obtain tin dicarboxylate as a pale yellow transparent liquid. 405 g of Compound B-1 (tin bis(2-ethylhexanoate)) was obtained.

This compound was analyzed by FT-IR, and the absorption of the carbonyl group of 2-ethylhexanoic acid at 1738 cm ^-1 disappeared, and the absorption of the carbonyl group in -CO-O-Sn-O-CO- was detected at 1650 cm ^-1 . confirmed.

<Production Example 2 (Bis(isononanoate)tin B-2)>
A pale yellow transparent liquid tin dicarboxylate compound B- was produced using the same production equipment and the same production method as Production Example 1 except that 2-ethylhexanoic acid in Production Example 1 was changed to 316.4 g (2 mol) of isononanoic acid. 433 g of 2(bis(isononanoate)tin) was obtained.

This compound was analyzed by FT-IR, and the absorption of the carbonyl group of isononanoic acid at 1738 cm ^-1 disappeared, and the absorption of the carbonyl group in -CO-O-Sn-O-CO- was confirmed at 1650 cm ^-1 .

<Production Example 3 (Bis(neodecanoate)tin B-3)>
By changing the 2-ethylhexanoic acid in Production Example 1 to 344.6 g (2 mol) of neodecanoic acid, and using the same production equipment and the same production method as in Production Example 1, a pale yellow transparent liquid tin dicarboxylate compound B- 461 g of 3 (tin bis(neodecanoate)) was obtained.

This compound was analyzed by FT-IR, and the absorption of the carbonyl group of neodecanoic acid at 1738 cm ^-1 disappeared, and the absorption of the carbonyl group in -CO-O-Sn-O-CO- was confirmed at 1650 cm ^-1 .

2. Preparation of main ingredient and curing agent Various additives shown in Table 1 were added in the parts (mass %) shown in the table and kneaded to prepare a main ingredient. On the other hand, tin dicarboxylate compounds B-1 to B-3 obtained in Production Examples 1 to 3 and various additives were mixed in the proportions (parts by mass) shown in Tables 2 to 4, and kneaded to form a curing agent. Prepared.

Details of the materials shown in the table are as follows.
Calfine 200M: Calcium carbonate (manufactured by Maruo Calcium Co., Ltd.)
Super 1500: Calcium carbonate (manufactured by Maruo Calcium Co., Ltd.)
MS Polymer S203: Silyl group-containing organic polymer (manufactured by Kaneka Corporation)
MS Polymer S303: Silyl group-containing organic polymer (manufactured by Kaneka Corporation)
DINP: Manufactured by J-Plus Co., Ltd. Sunsocizer EPS: Manufactured by Shin Nihon Rika Co., Ltd. Aronix M-309: Manufactured by Toagosei Co., Ltd. Disparon 308: Manufactured by Kusumoto Kasei Co., Ltd. 3260PW: Manufactured by Matsubara Sangyo Co., Ltd. UV70: Sabostab UV70 (made by SABO)
Irganox 1010: manufactured by BASF Laurylamine: primary reagent manufactured by Kanto Kagaku Co., Ltd. 4-Tertiary-butylcatechol: manufactured by DIC Corporation, chemical formula (5)
Ascorbic acid: manufactured by Showa Denko K.K., chemical formula (6)
Pyrogallol: Special grade reagent manufactured by Tokyo Chemical Industry Co., Ltd., chemical formula (5)
Hydroxyquinol: Special grade reagent manufactured by Tokyo Chemical Industry Co., Ltd., chemical formula (5)
Triethanolamine: Yoneyama Pharmaceutical Co., Ltd. special grade reagent, chemical formula (3)
Glycerin: manufactured by Miyoshi Yushi Co., Ltd., chemical formula (2)
Inositol: Special grade reagent manufactured by Tokyo Chemical Industry Co., Ltd., chemical formula (4)
Dithranol: Special grade reagent manufactured by Tokyo Chemical Industry Co., Ltd., chemical formula (7)
2,5-di-tert-butylhydroquinone: Seiko Chemical Co., Ltd. Gallic acid: Fuji Chemical Co., Ltd. Phloroglucinol: Tokyo Chemical Industry Co., Ltd. Express Reagent Diethanolamine: Nippon Shokubai Co., Ltd. N,N,N',N'-tetrakis(2-hydroxyethyl)ethylenediamine: Special grade reagent manufactured by Tokyo Chemical Industry Co., Ltd. 1,3-Propanediol: Special grade reagent manufactured by Tokyo Chemical Industry Co., Ltd. 1,2-Cyclohexane Diol: Special grade reagent manufactured by Tokyo Chemical Industry Co., Ltd.

3. Thin layer curability evaluation The following thin layer curability evaluation was performed on the moisture curable compositions prepared by mixing the main ingredients and curing agent of the Examples and Comparative Examples shown in Tables 2 to 4. The results are shown in Tables 2 to 4. The preparation of the main agent and curing agent, mixing of both components, and curing were carried out in a constant temperature room at a room temperature of 25±1° C. and a humidity of 50 to 60%.

As shown in the table, all Examples containing components [A] to [C] had good thin layer curability. On the other hand, all the comparative examples containing other alcohols instead of component [C] had poor thin layer curability.

<Thin layer curability evaluation>
After applying a moisture-curable composition containing a mixture of a base agent and a curing agent to a grind gauge and leaving it for 24 hours at a room temperature of 25 ± 1°C and a humidity of 50 to 60%, the positions at which the layer thickness becomes 5 μm, 15 μm, and 25 μm are applied. The degree of hardening of the surface was determined by touching a polyethylene sheet with a finger and evaluated according to the following criteria.
○: No tack △: With tack ×: Uncured (resin transferred to polyethylene sheet)

Claims (3)

A moisture-curable composition containing a polymer [A] having a reactive hydrolyzable silicon-containing group, a tin dicarboxylate compound [B], and an alcohol [C],
The tin dicarboxylate compound [B] is tin bis(2-ethylhexanoate), tin bis(isononanoate), or tin bis(neodecanoate) ,
The alcohol [C] is a moisture-curable composition represented by chemical formulas (2) to (7).
H _k -C-R ⁴ _4-K (2)
(In the formula, R ⁴ is -(CH ₂ ) _m -OH, m is 0 to 3, and may be the same or different. k is 0 or 1. )
N-R ⁵ ₃ (3)
(In the formula, R ⁵ is -(CH ₂ ) _n -OH, and n is 1 to 3 and may be the same or different.)
(In the formula, R ⁶ is -(CH ₂ ) _p -OH, p = 0 to 2, and may be the same or different. A is an oxygen atom or a carbon atom. .)
(In the formula, R ⁷ is a hydrogen atom, a hydroxyl group, or a hydrocarbon group, and may be the same or different from each other.)
The moisture-curable composition according to claim 1, wherein the content of the alcohol [C] is 0.1 to 1.0% by mass based on the tin dicarboxylate compound [B]. 1 or 2, wherein the alcohol [C] is at least one selected from the group consisting of 4-tert-butylcatechol, ascorbic acid, pyrogallol, hydroxyquinol, dithranol, triethanolamine, glycerin, and inositol. Item 2. Moisture-curable composition according to item 2.