JP2003335961A - Polyether-based plasticizer and resin composition containing the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a polyether-based plasticizer good in low-temperature extrudability and coatability, and to provide a room temperature-curable resin composition containing said plasticizer. <P>SOLUTION: The plasticizer has a structure represented by the formula (1) (wherein, R<SP>1</SP>is a polyether polyol residue ≥500 in molecular weight; R<SP>2</SP>is a 1-10C alkyl; and n is an integer of 1-4). <P>COPYRIGHT: (C)2004,JPO

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a polyether plasticizer suitable for use in a resin composition used as a waterproof material, a sealant, an adhesive, etc., and a room temperature curable resin composition using the same. .

[0002]

2. Description of the Related Art Conventionally, as plasticizers for resin compositions used for waterproof materials, sealants, adhesives, etc., phthalates such as dioctyl phthalate (DOP), adipates such as dioctyl adipate (DOA), Also known are ester-based plasticizers such as phosphoric acid esters, and urethane-based plasticizers as described in JP-A-63-251458. However, in recent years, the ester-based and urethane-based plasticizers have problems such as poor paintability due to bleeding and a decrease in plasticizing effect at low temperatures. Particularly, phthalic acid esters are listed as so-called environmental hormones. Since it is regarded as an environmental problem such as being upgraded, a plasticizer instead of this is desired.

Further, since the isocyanate group of the urethane resin reacts with the compound having a hydroxyl group, the plasticizer used in the one-pack urethane resin composition is required to have no hydroxyl group. Conventionally, polypropylene glycol diether in which hydroxyl groups at both ends of polypropylene diol are blocked with ether is known as a plasticizer using polyether as a raw material. However, there are problems that the reaction time is long to completely block the hydroxyl group so that it can be used in the one-component urethane resin composition, the synthesis requires two steps, and the cost is high, and the purification is costly. is there. Japanese Unexamined Patent Publication No. 6-49156 discloses a method of reacting a commercially available polyether polyol with an acetal or an orthoester to block hydroxyl groups to obtain a low-viscosity polyether polyol. High and unavailable.

[0004]

SUMMARY OF THE INVENTION It is an object of the present invention to provide a polyether plasticizer excellent in low temperature extrudability and coatability, and a room temperature curable resin composition containing the plasticizer.

[0005]

Means for Solving the Problems The present invention includes the following (1) to
Provided is a plasticizer having the specific structure described in (4) and a room temperature curable resin composition containing the plasticizer.

(1) A plasticizer having a structure represented by the following formula (1).

[Chemical 2] (In the formula, R ¹ is a polyether polyol residue having a molecular weight of 500 or more, and R ² is independently a C 1-10 group.
Is an alkyl group, and n is an integer of 1 to 4. )

(2) A room temperature curable resin composition containing a resin and the plasticizer described in (1) above.

(3) The room temperature curable resin composition as described in (2) above, wherein the resin is a urethane resin.

(4) The room temperature curable resin composition as described in (2) above, wherein the resin is a modified silicone resin.

(5) If the content of the plasticizer is the resin 1
0.5 to 40% by weight with respect to 00 parts by weight, The room temperature curable resin composition as described in any of (2) to (4) above.

[0011]

The present invention will be described in more detail below. A first aspect of the present invention is a plasticizer having a structure represented by the following formula (1).

[0012]

[Chemical 3]

In the formula, R ¹ has a molecular weight of 500 to 20,000,
Preferably 1000-15000, more preferably 20
The polyether polyol residue is from 0 to 12000, and specific examples thereof include a polyether polyol residue obtained by removing a part or all of the hydroxyl groups from the polyether polyol described later. R ^2's each independently represent an alkyl group having 1 to 10 carbon atoms, preferably 1 to 3 carbon atoms, and specific examples thereof include a methyl group, an ethyl group and a propyl group. In the present invention, all R ² are alkyl groups having 1 to 10 carbon atoms, which is preferable because the hydrolysis rate of the silyl ether bond (O—Si bond) does not become too fast. When R ² is an alkoxy group, the above-mentioned hydrolysis rate is increased, and the hydroxyl groups produced by the hydrolysis react with each other or with the isocyanate group, resulting in deterioration of workability and poor curing. Further, n is an integer of 1 to 4, and it is preferable that n is an integer of 1 to 3 because the raw materials are easily available.

As the above-mentioned polyether polyol, those exemplified as the polyol compound used in the production of a usual urethane prepolymer can be used, and specifically, ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol and glycerin can be used. , 1,1,1-trimethylolpropane, 1,2,5
-Hexanetriol, 1,3-butanediol, 1,
4-butanediol, 4,4'-dihydroxyphenylpropane, 4,4'-dihydroxyphenylmethane,
At least one selected from polyhydric alcohols such as 4,4′-dihydroxyphenylpropane and pentaerythritol, ethylene oxide, propylene oxide,
Preferable examples are polyols obtained by adding at least one selected from butylene oxide, styrene oxide and the like; polyoxytetramethylene oxide and the like. The number average molecular weight of the above-mentioned polyether polyol is preferably 500 to 20000.
000 to 15,000 is more preferable, and 200
It is more preferably 0 to 12000. When the number average molecular weight is in the above range, the room-temperature curable resin composition according to the second aspect of the present invention described later has good workability at low temperature and further does not bleed on the coated surface, which is preferable.

Further, the above polyether polyol may be a polyether monool shown below, specifically, aliphatic saturated alcohols such as methanol, ethanol, butanol and 2-ethylhexanol; cyclopentanol. , Alicyclic alcohols such as dimethylcyclohexanol; aromatic alcohols such as benzyl alcohol; carbocyclic alcohols such as furfuryl alcohol; at least one selected from monoalcohols such as phenolic alcohols such as phenol and cresol To
Preferable examples are polyether monools obtained by adding at least one selected from ethylene oxide, propylene oxide, butylene oxide, styrene oxide and the like. Moreover, the number average molecular weight of the above-mentioned polyether monool is preferably 300 to 10,000, and more preferably 500 to 5,000.

In the plasticizer according to the first aspect of the present invention, the polyether polyol and the compound containing a trialkylsilyl group are contained in an amount of 0.8 to 1.5 of the trialkylsilyl group per equivalent of the hydroxyl group. , Preferably 0.9-
It is preferably a reaction product obtained by reacting in the presence of a catalyst so as to be 1.2. Here, as the trialkylsilyl group-containing compound, specifically, trimethylsilyl chloride, 1, 1, 1, 3, 3, 3, 3-
Hexamethyldisilazane, N, N'-bis (trimethylsilyl) urea, triethylsilyl chloride and the like are exemplified. Of these, it is preferable to use trimethylsilyl chloride, 1,1,1,1,3,3,3-hexamethyldisilazane for reasons of ease of production.

Specific examples of the catalyst include, for example,
Examples of suitable catalysts include saccharin and triethylamine. Depending on the type of compound used as the above-mentioned trialkylsilyl group-containing compound, the catalyst preferably used is different. When trimethylsilyl chloride is used as the trialkylsilyl group-containing compound, it is preferable to use triethylamine as the catalyst, and similarly, 1, 1, 1,
When 3,3,3-hexamethyldisilazane is used, saccharin is preferably used.

As described above, the plasticizer according to the first aspect of the present invention comprises the polyether polyol and the trialkylsilyl group-containing compound in an amount of 0.8 equivalent of trialkylsilyl group per 1 equivalent of hydroxyl group. To 1.5, preferably 0.9 to 1.2, which is a reaction product obtained by reacting in the presence of a catalyst, and the reaction is carried out at 50 to 120 ° C., particularly 60 to 100 ° C. It is preferable to distill off the produced ammonia for 2 to 12 hours. By the above reaction, a plasticizer in which the hydroxyl group in the above polyether polyol is blocked with a trialkylsilyl group is obtained. Further, as described above, the plasticizer composed of the reaction product has a structure in which hydroxyl groups are blocked, and therefore, when used in the urethane resin composition described below, the urethane prepolymer may be used before or after curing of the composition. It is preferable because it becomes a plasticizer that does not react with the polymer and does not increase the viscosity.

Therefore, as the plasticizer according to the first aspect of the present invention, specifically, a compound represented by the following formula (2), that is, oxypropylene diol, 1, 1, 1, 1,
A reaction product with 3,3,3-hexamethyldisilazane is preferably exemplified.

[0020]

[Chemical 4]

In the formula, R ³ represents a diol residue used as an initiator of the polyol compound and obtained by removing the hydroxyl group of the diol compound. m represents the degree of polymerization and independently represents an integer of 3 to 150.

Since the plasticizer according to the first aspect of the present invention has a low viscosity and does not adversely affect the environment, all of them are suitably used as a plasticizer for waterproof materials, sealants, adhesives and the like. . Further, the plasticizer, in addition to the above characteristics, the hydroxyl groups of the polyether polyol are blocked, good compatibility with the urethane resin and excellent in coating properties, and can be produced at a relatively low cost. It is preferably used as a plasticizer.

A second aspect of the present invention is a room temperature curable resin composition containing the plasticizer according to the first aspect. Specifically, a urethane resin composition containing the plasticizer and a urethane resin, a modified silicone resin composition containing the plasticizer and a modified silicone resin, and an epoxy resin composition containing the plasticizer and an epoxy resin And a modified polysulfide resin composition containing the plasticizer and a modified polysulfide resin. The content of the plasticizer according to the first aspect is 100 parts by weight of each of the above resins,
It is 0.5-40% by weight, preferably 1-30% by weight, more preferably 5-30% by weight. When the content of the plasticizer is within this range, it is preferable because the workability and the physical properties after curing are excellent.

Here, the urethane resin is a resin containing a urethane prepolymer as a main component. The urethane prepolymer is a reaction product obtained by reacting a polyol compound with an excess of a polyisocyanate compound (that is, an excess of NCO groups with respect to OH groups), as in a normal one-pack type polyurethane resin composition. In general, 0.
It contains 5 to 5% by weight of isocyanate groups at the molecular ends.

As the polyisocyanate compound for producing such a urethane prepolymer, various compounds used for the production of ordinary one-pack type polyurethane resin compositions can be used. Specifically, for example, 2,4-tolylene diisocyanate (2,4-TDI), 2,6-tolylene diisocyanate (2,6-TDI), 4,4′-diphenylmethane diisocyanate (4,4′-). MD
I), 2,4'-diphenylmethane diisocyanate (2,4'-MDI), p-phenylene diisocyanate, polymethylene polyphenylene polyisocyanate,
Aromatic polyisocyanates such as xylylene diisocyanate (XDI) and 1,5-naphthalene diisocyanate (NDI); hexamethylene diisocyanate (HD
I), norbornane diisocyanate methyl (NBD
Aliphatic polyisocyanates such as I); isophorone diisocyanate (IPDI), H ₆ XDI (hydrogenated XDI),
Examples thereof include alicyclic polyisocyanates such as H ₁₂ MDI (hydrogenated MDI); carbodiimide-modified polyisocyanates of the above polyisocyanates, and isocyanurate-modified polyisocyanates thereof. These are 1
They may be used alone or in combination of two or more.

As the polyol compound for forming the urethane prepolymer, polyether polyol, polyester polyol, other polyols, and mixed polyols thereof can be used, as in the case of a normal one-pack type polyurethane resin composition. Of these polyol compounds, at least a polyether polyol is preferably used, that is, when a polyol having a polyether skeleton is contained in the urethane prepolymer, bleeding hardly occurs on the coated surface, which is preferable.

As the polyether polyol, the one used in the first embodiment can be used.
As the polyester polyol, specifically, for example, ethylene glycol, propylene glycol, butanediol pentanediol, hexanediol, cyclohexanedimethanol, glycerin, 1,1,1-trimethylolpropane, or one of other low-molecular polyols or Condensation polymer of two or more kinds with one or more kinds of low molecular carboxylic acid or oligomeric acid such as glutaric acid, adipic acid, pimelic acid, suberic acid, sebacic acid, terephthalic acid, isophthalic acid, dimer acid or the like; Examples thereof include ring-opening polymers such as propionlactone and valerolactone.

Specific examples of other polyols include polymer polyols, polycarbonate polyols; polybutadiene polyols; hydrogenated polybutadiene polyols; acrylic polyols; ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, butanediol,
Examples thereof include low molecular weight polyols such as pentanediol and hexanediol.

The mixing ratio of the polyol compound and the polyisocyanate compound when obtaining a urethane prepolymer having an isocyanate group at the molecular end, which is produced by using such a polyol compound and an excess of the polyisocyanate compound, is usually a polyol. OH group of compound 1
The ratio of the NCO groups of the polyisocyanate compound per equivalent (hereinafter referred to as NCO / OH) is preferably 1.2 to 5, and more preferably 1.4 to 4. Further, the production of the urethane prepolymer is carried out by mixing both compounds in a predetermined amount ratio and heating and stirring at 30 to 120 ° C., preferably 50 to 100 ° C., similarly to the ordinary urethane prepolymer.

The modified silicone resin is a resin containing as a main component an uncured oligomer (hereinafter referred to as modified silicone) having an average of one or more hydrolyzable silicon-containing groups in the molecule. It is preferably used for sealing outer wall materials such as. Here, the average value of the hydrolyzable silicon-containing group in the molecule is a value obtained by dividing the total molecular weight of the hydrolyzable silicon-containing group compound by the total equivalent weight of the hydrolyzable silicon-containing group.

The hydrolyzable silicon-containing group is a silicon-containing group that causes a condensation reaction in the presence of moisture or a cross-linking agent, if necessary, by using a catalyst or the like. Specifically, for example, Halogenated silyl group, alkoxysilyl group, alkenyloxysilyl group, acyloxysilyl group,
Examples thereof include aminosilyl group, aminooxysilyl group, oxime silyl group, and amidosilyl group. Of these, an alkoxysilyl group is preferred because it is easy to handle.

The modified silicone is an uncured oligomer having an average of one or more hydrolyzable silicon-containing groups in the molecule as described above, and the hydrolyzable silicon-containing groups in the molecule are It may be present at the end, on the side chain, or on both.

Specific examples of the main chain of the modified silicone include polyethers such as alkylene oxide polymers, polyesters, ether / ester block copolymers, vinyl polymers, vinyl copolymers, and diene polymers. Polymers, saturated hydrocarbons may be mentioned, may be used alone,
You may mix and use 2 or more types. Of these, those having a polyether as the main chain of the modified silicone are preferable because bleeding hardly occurs on the coated surface. Further, in order to improve the weather resistance of the modified silicone resin, it is preferable to use an acrylate resin having an alkoxysilyl group blended or grafted with the modified silicone.

Therefore, the modified silicone is preferably one having an alkoxylyl group at the terminal and / or side chain in the molecule and a polyether skeleton as the main chain. Specifically, for example, MS polymer, EPION manufactured by Kanegafuchi Chemical Co., Ltd .; Exestar manufactured by Asahi Glass Co., Ltd.

Each of the above resins contained in the room temperature curable resin composition of the present invention is, if necessary, a filler and a plasticizer according to the first aspect of the present invention (hereinafter, also referred to as a plasticizer of the present invention). Other than plasticizers, antioxidants, antioxidants, pigments or dyes, thixotropic agents, antistatic agents, adhesion imparting agents,
You may mix | blend various well-known additives, such as a flame retardant, a solvent, a silane coupling agent, a dispersing agent, a ultraviolet absorber, a dehydrating agent, and a hardening catalyst.

Specific examples of the filler include calcium carbonate (for example, surface-treated calcium carbonate), silica, carbon black, clay, talc, titanium oxide, quick lime, kaolin, zeolite, diatomaceous earth, vinyl chloride paste. Examples thereof include resins, glass balloons and vinylidene chloride resin balloons. These fillers may be used alone or in combination of two or more. When the resin is a urethane resin containing a urethane prepolymer as a main component, the content of the filler is preferably 50 to 200 parts by weight, and 70 to 180 parts by weight with respect to 100 parts by weight of the urethane prepolymer. More preferably, it is part by weight. Within the above range, the physical properties are excellent.

Specific examples of the plasticizer other than the plasticizer of the present invention include dioctyl phthalate (DOP),
Dimethyl phthalate, diethyl phthalate, dibutyl phthalate (DBP), dilauryl phthalate (DL
P), phthalates such as dibutylbenzyl phthalate (BBP), dioctyl adipate, diisodecyl adipate, diisodecyl succinate, dibutyl sebacate, butyl oleate, trioctyl phosphate, trioctyl phosphate, tris (chloroethyl) phosphate, tris. (Dichloropropyl) phosphate,
Examples thereof include propylene glycol adipate polyester, butylene glycol adipate polyester, alkyl epoxy stearate, and epoxidized soybean oil. These plasticizers are inexpensive, and one or more of them can be used in combination with at least one of the plasticizers of the present invention. However, considering the effects on the environment, coating suitability, etc., their content should be reduced. It is preferable to increase the content of the plasticizer of the present invention.

Specific examples of the antioxidant include butylhydroxytoluene (BHT), butylhydroxycyanisole (BHA), diphenylamine, phenylenediamine, and triphenylphosphite. Specific examples of the anti-aging agent include N,
N'-diphenyl-p-phenylenediamine (DPP
D), N, N'-dinaphthyl-p-phenylenediamine (DNPD), 2,2,4-trimethyl-1,3-dihydroquinoline (TMDQ), N-phenyl-1-naphthylamine (PAN) and the like. From the viewpoint of heat resistance, it is preferable to use a plurality of them in combination. Specific examples of the pigment include inorganic pigments such as titanium dioxide, zinc oxide, ultramarine blue, rouge, lithobon, lead, cadmium, iron, cobalt, aluminum, hydrochloride and sulfate; azo pigments and copper phthalocyanine pigments. And the like, and specific examples of the dye include zinc oxide, zinc sulfide, chromium oxide, and red iron oxide. Specific examples of the thixotropy imparting agent include Aerosil (manufactured by Nippon Aerosil Co., Ltd.) and Disparlon (manufactured by Kusumoto Kasei Co., Ltd.). As an antistatic agent,
In general, ionic compounds such as quaternary ammonium salts and amines, or hydrophilic compounds such as polyethylene glycol and ethylene oxide derivatives can be mentioned. As the adhesion-imparting agent, specifically, for example, terpene resin, phenol resin, terpene-phenol resin,
Examples include rosin resin and xylene resin. As the flame retardant, specifically, for example, chloroalkyl phosphate, dimethylmethylphosphonate, bromine, phosphorus compound,
Examples thereof include ammonium polyphosphate and diethyl bishydroxyethylaminophosphate. As the dehydrating agent, one obtained by reacting methylhydrogenpolysiloxane with a higher fatty acid such as palmitic acid or stearic acid, specifically, KF-910 manufactured by Shin-Etsu Chemical Co., Ltd. can be mentioned. Specific examples of the solvent include aromatic hydrocarbon solvents such as xylene and toluene, and mineral spirits.

The method for producing the room temperature curable resin composition of the present invention is not particularly limited, and for example, it can be produced by mixing with a roll, a kneader, an extruder, a universal stirrer or the like. A method may be used in which each raw material (plasticizer, resin, and additive of the present invention) is sufficiently kneaded with a stirrer under reduced pressure or in an inert atmosphere and uniformly dispersed to obtain a composition. Further, the use of the room temperature curable resin composition of the present invention is not particularly limited to the sealing material, and for example, it can be used for various adhesives, waterproof materials and the like.

Since the room temperature curable resin composition of the present invention contains the plasticizer of the present invention, it is excellent in workability, storage stability and the like. Among them, a room temperature curable resin composition containing a urethane resin or a modified silicone resin and a plasticizer of the present invention is a urethane prepolymer forming a urethane resin or a modified silicone forming a modified silicone resin, and the plasticizer. It is useful because it has a high affinity and compatibility, and is extremely excellent in coatability after curing and workability at low temperature. Further, the room temperature curable resin composition of the present invention is useful because it does not use phthalic acid ester which has been conventionally used as a plasticizer at all, or even when it is used, the amount used can be reduced, and therefore it is also excellent in environmental friendliness. Is.

[0041]

EXAMPLES The present invention will be specifically described below with reference to examples, but the present invention is not limited thereto. (Example 1) Dry polypropylene glycol monool having a number average molecular weight of 1200 (trade name: Newpol L)
B-285, manufactured by Sanyo Chemical Industries, Ltd.) 1200 g, 1,
A composition containing 81 g of 1,1,3,3,3-hexamethyldisilazane (trade name: A-166, manufactured by Nippon Unicar Co., Ltd.) and 0.5 g of saccharin was reacted at 100 ° C. for 6 hours, and the hydroxyl group was methylsilyl. A plasticizer blocked with a group was obtained. The plasticizer is silylated PPG1. The IR spectrum of the obtained silylated PPG1 was measured, and it was confirmed that the hydroxyl groups had completely disappeared. In addition, silylated PPG
The viscosity of 1 was 155 mPa * s (20 degreeC).

(Example 2) Dry number average molecular weight 100
To 100 g of 00 polyoxypropylene triol (trade name: Preminol 3010, manufactured by Asahi Glass Co., Ltd.), 1,
A composition prepared by adding 26 g of 1,1,3,3,3-hexamethyldisilazane (trade name: A-166, manufactured by Nippon Unicar Co., Ltd.) and 0.5 g of saccharin was reacted at 100 ° C. for 12 hours, and the hydroxyl group was methylsilyl. A plasticizer blocked with a group was obtained. The plasticizer is silylated PPG2. The IR spectrum of the obtained silylated PPG2 was measured, and it was confirmed that the hydroxyl groups had completely disappeared. In addition, silylated PP
The viscosity of G2 was 3400 mPa · s (25 ° C.).

(Examples 3, 4 and Comparative Examples 1 to 3) The compounds were blended in the numerical values (mass ratio) shown in Table 1 below to prepare compositions. The low-temperature extrudability and coatability of the obtained composition were evaluated by the methods described below.

(1) Low-temperature extrudability The low-temperature extrudability of the composition was measured in accordance with JIS-A1439-1997 "Testing Method for Building Sealants" at a test temperature of 5 ° C. The composition in which the extrusion time was shortened by 5% or more and less than 10% with respect to the blank was designated as Δ, and the composition in which the extrusion time was shortened by 10% or more was designated as ◯. (2) Coating property Acrylic emulsion paint (Aron Coat ST, manufactured by Toagosei Co., Ltd.) is applied to each resin composition after curing and the temperature is 2 at 50 ° C.
After leaving it for a week, it was exposed to the outdoors for 1 month, and the surface stickiness and stain resistance were evaluated. Good paintability was indicated by ◯, and poor paintability was indicated by x.

[0045]

[Table 1]

From the results shown in Table 1, resin compositions using the plasticizer of the present invention obtained in Examples 1 and 2 (Example 3
And the compositions shown in Example 4), all the hydroxyl groups in the plasticizer are blocked with trimethylsilyl groups, so that an increase in viscosity due to hydrogen bonding between polar groups of the plasticizer is suppressed, and Comparative Examples 1 to 3 It was found that the low temperature extrudability was superior to that of the composition shown in FIG. In addition, not using the plasticizer of the present invention but using only the phthalate ester in the same amount of the plasticizer as in Example 3 (Comparative Example 1) not only has an environmental problem, but also has a poor coatability. It turned out to be inferior.

The following components were used as the components in Table 1 above. (1) Resin urethane prepolymer 1 80 parts by weight of polypropylene triol having an average molecular weight of 5000, polypropylene diol 2 having an average molecular weight of 2000
Terminal active NCO group-containing urethane prepolymer 1 obtained by putting 0 parts by weight into a reaction vessel, adding MDI so that NCO group / OH group = 1.8, stirring at 80 ° C. for 12 hours, and reacting Was used.

Modified Silicone MSX911 As modified silicone, modified silicone (MSX911 manufactured by Kanegafuchi Chemical Co., Ltd.) was used.

(2) Plasticizer dioctyl phthalate (DOP) Dioctyl phthalate was used. 2 moles of polypropylene monool having a urethane molecular weight of 500 and 1 mole of isophorone diisocyanate were mixed with bismuth catalyst 10
A reaction product obtained by reacting in the presence of ppm until the isocyanate group was used was used. PPG A polyoxypropylene triol having a number average molecular weight of 10,000 (trade name: Preminol 3010, manufactured by Asahi Glass Co., Ltd.) was used.

(3) Calcium carbonate As the calcium carbonate, a fatty acid ester-treated calcium carbonate (trade name: Sealets 200, manufactured by Maruo Calcium Co., Ltd.) was used. (4) Vinylsilane As the vinylsilane, vinyltrimethoxysilane (trade name: A171, manufactured by Nippon Unicar Co., Ltd.) was used. (5) Epoxysilane As the epoxysilane, γ-glycidoxypropyltrimethoxysilane (trade name: A187, manufactured by Nippon Unicar Co., Ltd.) was used. (6) Tin catalyst As a tin catalyst, dibutyltin diacetylacetonate (trade name: Neostan U-220, manufactured by Nitto Kasei Co., Ltd.) was used.

[0051]

As described above, the plasticizer of the first aspect of the present invention is preferably used as a plasticizer for waterproofing materials, sealants, adhesives, etc., and particularly as a plasticizer for one-component urethane sealants. It is preferably used. The first aspect of the present invention
The room-temperature curable resin composition of the second aspect of the present invention containing the plasticizer of the aspect (1) has excellent workability, storage stability, coatability after curing, etc. Suitable for use.

─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. ⁷ Identification code FI theme code (reference) C08L 71:02) F term (reference) 4J002 CH052 CK021 CK031 CK041 CN021 CP171 CP181 EX036 FD010 FD020 FD022 FD026 FD070 FD090 FD200 GJ01 GJ02 HA02 4J005 BD08

Claims (5)

[Claims] 1. A plasticizer having a structure represented by the following formula (1). [Chemical 1] (In the formula, R ¹ is a polyether polyol residue having a molecular weight of 500 or more, and R ² is independently a C 1-10 group.
Is an alkyl group, and n is an integer of 1 to 4. ) 2. A room temperature curable resin composition containing a resin and the plasticizer according to claim 1. 3. The room temperature curable resin composition according to claim 2, wherein the resin is a urethane resin. 4. The room temperature curable resin composition according to claim 2, wherein the resin is a modified silicone resin. 5. The room temperature curability according to any one of claims 2 to 4, wherein the content of the plasticizer is 0.5 to 40% by weight with respect to 100 parts by weight of the resin. Resin composition.