JP2001181367A - One-pack room temperature-curable polyurethane resin- based composition and adhesive - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a moisture-curable urethane resin composition not causing foaming by carbon dioxide gas when cured and excellent in curing properties and an adhesive using the same. SOLUTION: The one-pack room temperature-curable polyurethane resin-based composition comprises as essential components (A) a polyurethane resin bearing at least two isocyanate groups in the molecule, (B) a compound bearing at least two oxazolidine rings in the molecule, (C) one or more acidic substances selected among nitrobenzoic acid, chlorobenzoic acid and methoxybenzoic acid, and (D) 4-toluenesulfonyl isocyanate(PTSI).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a one-component liquid which is excellent in non-foaming property, storage stability and curability by utilizing a reaction of hydrolyzing an oxazolidine ring with moisture (moisture) in the air to generate active hydrogen. The room-temperature-curable polyurethane resin composition is industrially useful as an adhesive, sealing agent, or coating agent for buildings or vehicles.

[0002]

2. Description of the Related Art Various one-part room-temperature-curable polyurethane resin compositions have been studied, but most of them are a reaction between an isocyanate group and moisture (moisture), that is, a reaction of an isocyanate group. One part becomes an amine, and the generated amine reacts with the remaining isocyanate group to cure,
Bubbling accompanying the generation of carbon dioxide gas could occur. or,
As a method for increasing the curing rate, a curing accelerator such as a metal-based catalyst or an amine-based catalyst is often used in combination.

As a technique for suppressing the foaming phenomenon, for example,
JP-A-7-289989 discloses that a compound comprising an alicyclic enamine derivative is hydrolyzed by moisture (moisture), and a generated active hydrogen group (amine) reacts with an isocyanate group to cure. A room-temperature-curable polyurethane resin composition having no foaming and excellent curability has been disclosed. Here, the curing rate of the composition resulting from the hydrolysis rate of the alicyclic enamine derivative is adjusted by the addition amount of a specific acidic catalyst which is a curing accelerator.

The room temperature-curable polyurethane resin composition described in Japanese Patent Application Laid-Open No. 7-289989 is characterized by being non-foamed and excellent in curability.
In order to increase the curing speed, a large amount of an acidic catalyst is required as a curing accelerator, and as a result, there is a problem that storage stability is significantly impaired.

Further, Japanese Patent Application Laid-Open Nos. Hei 6-293821, Hei 7-33852, Hei 7-10949, Hei 9-278857, and Hei 10-22 are disclosed.
No. 6720 discloses a non-foaming method utilizing the fact that a compound having an oxazolidine ring is hydrolyzed by moisture (moisture) and the generated active hydrogen groups (amine and hydroxyl groups) react with isocyanate groups to cure. A room-temperature-curable polyurethane resin composition having excellent curability is disclosed.

However, JP-A-6-293821 discloses a polyurethane resin containing no oxyethylene chain and N
-2-Hydroxyalkyloxazolidine is reacted with a large excess of isocyanate group, and there is a problem that curability is slow.

On the other hand, in Japanese Patent Application Laid-Open No. 7-33852,
A compound obtained by reacting an isocyanate group such as xylylene diisocyanate or hexamethylene diisocyanate with a hydroxyoxazolidine compound is used as an isocyanate.
In addition, there is a problem that the curability is slow because it is mixed with a polyurethane resin containing a thiol group.

JP-A-7-10949 describes a mixture of a polyurethane resin having an isocyanate group having a polyoxyethylene chain and a reaction product of tolylene diisocyanate and a hydroxyoxazolidine compound. Similarly, there is a problem that the curability is slow.

Japanese Patent Application Laid-Open No. 9-278857 discloses a polyurethane resin having an isocyanate group, an oxazolysine compound having a polyoxyethylene chain, and an acidic substance having an acid dissociation coefficient pKa of 1.0 to 4.0. The mixture is described and is characterized by no foaming and excellent curability, but requires an acidic catalyst having a low pKa as a curing accelerator in order to increase the curing speed, and as a result, storage stability However, there is a problem that is significantly impaired. As a method for improving storage stability, it is conceivable to mix PTSI as described in the Examples. Particularly, when salicylic acid and PTSI are allowed to coexist, the dehydration reaction of salicylic acid proceeds with time. In addition, there has been a problem that the catalytic effect is reduced and the curability is delayed with time.

[0010] Also, in Japanese Patent Application Laid-Open No. Hei 10-226720,
A mixture of a polyurethane resin in which an oxazolidine group is added at a specific ratio to an isocyanate group and a PTSI derivative has been proposed. However, there is a problem in curability, and in order to enhance the curability, the amount of the PTSI derivative used was increased. In this case, there is a problem in storage stability, and further, there is a problem that foaming occurs.

[0011]

SUMMARY OF THE INVENTION An object of the present invention is to provide a composition which is not foamed (non-foamable) immediately after compounding, after storage, and when cured, has excellent curability, good storage stability, An object of the present invention is to provide a one-part room temperature-curable polyurethane resin composition which does not deteriorate during elongation.

[0012]

Means for Solving the Problems The present inventors have conducted intensive studies on the above problems and found that a polyurethane resin having an isocyanate group, a compound having an oxazolidine ring, particularly a compound having an oxazolidine ring containing an oxyethylene chain, A specific acidic substance, and the use of PTSI, compared to the case of the alicyclic enamine derivative of JP-A-7-289989, because the amount of the acidic catalyst is effective with a small amount,
Excellent storage stability and good curability. Compared to JP-A-6-293821, JP-A-7-33852, and JP-A-7-109949, the oxazolidine compound has a higher ethylene content. Excellent curability due to containing an oxide compound, JP-A-9-278
The present inventors have found that a one-part room temperature-curable polyurethane resin composition having excellent storage stability can be obtained as compared with 857 and JP-A-10-226720, and completed the present invention.

That is, the present invention provides (A) a polyurethane resin having two or more isocyanate groups in a molecule;
A compound having two or more oxazolidine rings in the molecule,
(C) One or two or more acidic substances selected from nitrobenzoic acid, chlorobenzoic acid, or methoxybenzoic acid, and (D) PTSI as essential components. It is intended to provide a curable polyurethane resin composition. More preferably, the compound (B) is reacted with a polyurethane resin (b1) containing an oxyethylene chain and having two or more isocyanate groups in the molecule and an N-hydroxyalkyloxazolidine (b2). The obtained compound having two or more oxazolidine groups in the molecule, and the amount of the acidic substance (C) used is in the range of 0.01 to 2.0% by weight based on the weight ratio to the compound (B). That the amount of PTSI (D) used is in the range of 0.01 to 2.0% by weight based on the weight ratio to the compound (B), and that the isocyanate groups of the polyurethane resin (A) The ratio of active hydrogen groups (amine and hydroxyl groups) generated by hydrolysis of the oxazolidine ring of compound (B) is NCO / * H = 0.
In the range of 5 to 5.0, polyurethane resin (b1)
Is in the range of 1 to 10% by weight based on the total weight of the polyurethane resin (A) and the compound (B), and is composed of the one-part room temperature-curable polyurethane resin composition. An adhesive is provided.

[0014]

BEST MODE FOR CARRYING OUT THE INVENTION The polyurethane resin (A) and the compound (B) used in the present invention are used as raw materials.
The polyurethane resin (b1) is a compound having at least two isocyanate groups in the molecule, and is a compound of an organic polyisocyanate alone or an organic polyisocyanate and a polyol under an excess of isocyanate. It is a polyurethane resin prepared by an ordinary method.

As the organic polyisocyanate, 2,4
-Tolylene diisocyanate, 2,6-tolylene diisocyanate, diphenylmethane diisocyanate, partially-carbodiimidated diphenylmethane polyisocyanate, polymethylene polyphenyl polyisocyanate
Aromatic isocyanates such as naphthalene diisocyanate and phenylene diisocyanate; aliphatic diisocyanates such as hexamethylene diisocyanate; isophorone diisocyanate; xylylene diisocyanate Or one selected from alicyclic diisocyanates such as hydrogenated diphenylmethane diisocyanate, hydrogenated xylylene diisocyanate, cyclohexane diisocyanate, or
Mixtures of two or more are mentioned.

The polyol used in the present invention is a polyester polyol, a polyester polyol, other polyols, or a mixture thereof. For example, a polyol produced using a double metal cyanide complex as a catalyst is also included.

Examples of the polyether polyol include ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, glycerin, trimethylolpropane, glucose, sorbitol, and sulfur.
Add one or more selected from propylene oxide, ethylene oxide, butylene oxide, styrene oxide, etc. to one or more polyhydric alcohols selected from closes and the like. And polyoxytetramethylene polyol.

Examples of the polyester polyol include ethylene glycol, propylene glycol, butanediol, pentanediol, hexanediol, cyclohexanedimethanol, glycerin, trimethylolpropane and other low molecular weight polyols. Or one or more selected from the group consisting of glutaric acid, adipic acid, pimelic acid, suberic acid, sebacic acid, terephthalic acid, isophthalic acid, dimer acid, hydrogenated dimer acid and other low molecular weight compounds 1 selected from dicarboxylic acids and oligomeric acids
Species or condensation polymers with two or more species and ring-opening polymers such as propiolactone, caprolactone, valerolactone and the like.

Other polyols include, for example, polycarbonate polyols, polybutadiene polyols, and the like.
Examples include hydrogenated polybutadiene polyol and acrylic polyol. Also, ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, butanediol, pentanediol,
Low molecular weight polyols such as hexanediol, cyclohexanedimethanol glycerin, trimethylolpropane, glucose, sorbitol, and sucrose are also included.

The number of isocyanate groups in the molecule of the polyurethane resin (A) is preferably 2 or more, more preferably 2 or more and 3 or less. If the number of isocyanate groups is less than 2, the durability of the cured coating film may decrease, and if it exceeds 3, the storage stability may be impaired.

The compound (B) having two or more oxazolidine rings in the molecule is a compound having two or more isocyanate rings in the molecule.
And a compound obtained by reacting a compound having an ox group with an oxazolidine compound.

When the polyurethane resin (b1) is used as the compound (B) as the isocyanate compound, the number average molecular weight of the polyurethane resin (b1) is preferably 10,000 or less. If the number average molecular weight exceeds 10,000, the storage stability may decrease. The average number of isocyanate groups in the molecule of the polyurethane resin (b1) is preferably 2 to 4. If it is less than 2, the curability may decrease, and if it exceeds 4, the storage stability may decrease.

Also, the polyurethane resin (b1) and N-2-
NCO with hydroxyalkyl oxazolidine (b2)
The / 0H equivalent ratio is preferably from 0.95 to 1.5, more preferably from 1.02 to 1.15. NCO / 0H
If the equivalent ratio is less than 0.95, N-2-hydroxyalkyloxazolidine tends to remain unreacted, and storage stability may decrease. If the NCO / OH equivalent ratio exceeds 1.5, the amount of the prepolymer having one oxazolidine ring in the molecule increases, and the curing rate may decrease.

N-2- used in the synthesis of compound (B)
Hydroxyalkyl oxazolidines are synthesized by a dehydration reaction of a tertiary amine and an alkanolamine having a 2-hydroxyethyl group with an aldehyde or ketone. The alkanolamines include ethanolamine, diethanolamine, isopropanolamine,
Diisopropanolamine, isobutanolamine, diisobutanolamine, hydroxyethylaminomethyl alcohol, ethylenediamine, propylenediamine, butylenediamine, hexamethylenediamine, diethylenetriamine, bis (aminomethyl) cyclohexane, xylylenediamine, dicyclohexyldiamine, Isophoronediamine, isopropylidenebis (aminocyclohexane), methylenebis (aminocyclohexane), polymethylenepolyamine, diaminotoluene,
A compound having a secondary amino-2-hydroxyl group in which an amine such as phenylenediamine is substituted with a 2-hydroxyethyl group.

Aldehydes or ketones include butyraldehyde, trimethylacetaldehyde, triethylacetaldehyde, valeroaldehyde, and furfural
, Benzaldehyde, methyl ethyl ketone, cyclohexanone, trimethylcyclohexanone, acetophenone, anisaldehyde, hexanal, octanal,
Decanal, citral and the like can be mentioned.

The compounding ratio of the polyurethane resin (A) and the compound (B) is such that active hydrogen (amine) generated by hydrolysis of the isocyanate group of the polyurethane resin (A) and the oxazolidine ring of the compound (B) is used. And an equivalent ratio to the hydroxyl group) are preferably in the range of 0.5 to 5.0.
More preferably, it is 0.75 to 3.0. If it is less than 0.5, the durability of the cured coating film may be impaired,
If it exceeds 5.0, the curability may decrease, and foaming may easily occur in the cured coating film due to the generation of carbon dioxide gas.

The acidic substance (C) used in the present invention is one or more acidic substances selected from nitrobenzoic acid, chlorobenzoic acid and methoxybenzoic acid. The amount of the acidic substance (C) is arbitrarily adjusted depending on the desired curability, but is usually in the range of preferably 0.01 to 2.0% by weight based on the weight of the compound (B). is there. If it is less than 0.01% by weight, the curability may decrease, and if it exceeds 2.0% by weight, the storage stability may decrease.

The amount of PTSI (D) used in the present invention is usually 0.1% by weight based on the compound (B).
The range is from 0.01 to 2.0% by weight. If it is less than 0.01% by weight, the storage stability may be deteriorated, and if it is more than 2.0% by weight, the cured coating film may be foamed.

The composition of the present invention may optionally contain a diluent,
Fillers, thixotropic agents, stabilizers and other various additives,
The mixture can be mixed and used until it becomes uniform using an appropriate kneading apparatus.

Examples of the diluent include solvents such as acetone, methyl ethyl ketone, ethyl acetate, toluene and xylene, dioctyl phthalate, dibutyl phthalate, dinonyl phthalate, dioctyl adipate and dibutyl adipate.
And plasticizers such as dinonyl adipate.

As the filler, calcium carbonate, kaolin, clay, talc, bentonite and the like can be used. As the thixotropic agent, fatty acid, fatty acid metal salt, fatty acid ester, paraffin, resin acid, surfactant, surface-treated filler surface-treated with polyacrylic acid, etc., polyvinyl chloride powder, fine powder silica, bentonite, Sepiolite and the like.

Examples of the various additives include metal-based and amine-based reaction accelerators for isocyanate groups, and rosin ester-based and terpene phenol-based tackifiers.

The one-part room temperature curable urethane resin composition of the present invention is mainly used as an adhesive or a sealing agent.
It can also be used as a coating agent for wall materials, waterproof materials, floor materials, paints and the like. The one-part room temperature-curable urethane resin composition of the present invention has excellent curability and is used as an extremely reliable adhesive, sheathing agent and coating agent which does not cause foaming in the cured coating film. I can do things.

[0034]

EXAMPLES The present invention will be described below with reference to examples, but the present invention is not limited to the examples. Parts in Examples are parts by weight.

<Synthesis Method> (Preparation Example 1 of Polyurethane Resin) Polypropylene etherdiol having a number average molecular weight of 2000 was placed in a clean flask.
Then, while stirring under a nitrogen atmosphere, 174.16 g of 2,4-tolylene diisocyanate, that is, NCO / OH at an equivalent ratio of 2.00 is charged. Further, while stirring under a nitrogen atmosphere, the temperature of the resin is set to about 70 ° C. to about 90 ° C., and the reaction is carried out for about 48 hours.
CO-1) was obtained.

(Preparation Example 2 of Polyurethane Resin) In a clean flask, polyethylene propylene ether diol having a number average molecular weight of 2,000 (an ethylene oxide content of about 10
%), And stirred under a nitrogen atmosphere with 2,4-tolylene diisocyanate 174.16.
g, that is, NCO / OH is set to 2.00 in equivalent ratio. Further, while stirring under a nitrogen atmosphere, the resin temperature is set to about 70 ° C. to about 90 ° C.
The reaction was carried out for an hour to obtain a urethane resin (NCO-2) having an NCO weight% of about 3.58%.

(Preparation Example 2 of Polyurethane Resin 3) Polyethylene propylene etherdiol having a number average molecular weight of 2000 (ethylene oxide content of about 2
(0%) 1000.00 g and 2,4-tolylene diisocyanate 174.1 while stirring under a nitrogen atmosphere.
6 g, that is, NCO / OH is set to 2.00 in equivalent ratio. Further, while stirring under a nitrogen atmosphere, the resin temperature is set so as to be about 70 ° C. to about 90 ° C.
The reaction was carried out for 8 hours to obtain a urethane resin (NCO-3) having an NCO weight% of about 3.58%.

(Preparation Example 1 of Oxazolidine Ring-Containing Compound) Polyurethane resin (NCO-1) was placed in a clean flask.
1174.16 g is charged, and while stirring under a nitrogen atmosphere, 144.75 g of 2-isopropylpropyl-3 (2-hydroxyethyl) 1,3 oxazolidine, that is, NCO / OH is set to 1.10 in equivalent ratio. Furthermore, while stirring under a nitrogen atmosphere, the resin temperature is increased from about 70 ° C. to about 90 ° C.
° C, and reacted for about 48 hours to obtain an oxazolidine ring-containing compound (OXZ-1). As a result of measuring the molecular weight of the compound, the residual ratio of 2-isopropylpropyl-3 (2-hydroxyethyl) 1,3 oxazolidine was 1% by weight.
It was confirmed that:

(Preparation Example 2 of Oxazolidine Ring-Containing Compound) Polyurethane resin (NCO-2) was placed in a clean flask.
1174.16 g is charged, and while stirring under a nitrogen atmosphere, 144.75 g of 2-isopropylpropyl-3 (2-hydroxyethyl) 1,3 oxazolidine, that is, NCO / OH is set to 1.10 in equivalent ratio. Further, while stirring under a nitrogen atmosphere, the resin temperature is about 70 ° C. to about 90 ° C.
The reaction was carried out for about 48 hours to obtain an oxazolidine ring-containing compound (OXZ-2). As a result of measuring the molecular weight of the compound, it was confirmed that the residual ratio of 2-isopropylpropyl 3 (2-hydroxyethyl) 1,3 oxazolidine was 1% by weight or less.

Preparation Example 3 of Oxazolidine Ring-Containing Compound Polyurethane resin (NCO-3) was placed in a clean flask.
1174.16 g is charged, and while stirring under a nitrogen atmosphere, 144.75 g of 2-isopropylpropyl-3 (2-hydroxyethyl) 1,3 oxazolidine, that is, NCO / OH is set to 1.10 in equivalent ratio. Further, while stirring under a nitrogen atmosphere, the resin temperature is about 70 ° C. to about 90 ° C.
And reacted for about 48 hours to obtain an oxazolidine ring-containing compound (OXZ-3). As a result of measuring the molecular weight of the compound, it was confirmed that the residual ratio of 2-isopropylpropyl 3 (2-hydroxyethyl) 1,3 oxazolidine was 1% by weight or less.

<Compounding Formulation> NS # 200 (Nitto Powder Chemical Industry Co., Ltd.) was placed in a closed planetary mixer.
Manufactured, surface-untreated heavy calcium carbonate) 800.00 g,
Shiraishihana CCR (manufactured by Shiraishi Industry Co., Ltd., surface-treated light calcium carbonate) 200.00 g and dioctylphthalate
(Hereinafter referred to as DOP) 500.00 g, and the mixture temperature is set to about 110 ° C. to 130 ° C., and about 8 kP
The mixture is dehydrated under reduced pressure to adjust the water content of the mixture to 0.05% by weight or less. Next, cool down to about 50 ° C or less,
And mix until uniform. Finally, a predetermined amount of a polyurethane resin, an oxazolidine ring-containing compound, and an acidic substance are charged and mixed until uniform, and then, about 8 k
Defoaming was performed under a reduced pressure of Pa to obtain a one-part room temperature-curable polyurethane resin. In addition, charging, mixing, and taking-out were performed in a nitrogen atmosphere in order to prevent moisture from being mixed.

<Test Method> (Non-foaming test) The non-foaming property was evaluated by using a frame surrounded by a frame on all sides.
After flowing a sample on a plate (30 cm x 30 cm) at a ratio of 2 mm in thickness and curing it at about 50 ° C x 50%,
The surface of the coating film was observed for blisters and pinholes. A sample without blisters and pinholes was rated as "O", and a sample with blisters and pinholes was rated as "x". For the test, a sample (hereinafter referred to as an initial product) stored for one day in an atmosphere of about 20 ° C.
A sample stored in an atmosphere of 0 ° C. for 14 days (hereinafter referred to as a product after storage stability test) was used.

(Tack Free Time) Based on JIS-A 1439: 1997. In addition, the initial product and the product after the storage stability test were used for the test. (Deterioration test during elongation during heat treatment) Based on JIS-A 6021: 1995. In addition, the initial product was used for the test. (Storage stability test) Regarding the storage stability, about 500 g of the compounded product was put into a clean 500-mL square can substituted with nitrogen, purged with nitrogen, sealed, and allowed to stand in an atmosphere of about 50 ° C for 2 weeks. The presence of later fluidity was checked. A sample having fluidity was rated as ○, and a sample without fluidity was rated as ×. <Test results>

[0044]

[Table 1] Formulation conditions and test results

Note) NCO / * H: Equivalent ratio of active hydrogen groups (amine and hydroxyl group) generated by hydrolysis of isocyanate group and oxazolidine ring. Note) PTSI weight%: indicates the weight% of PTSI based on the compound (B) having an oxazolidine ring. Note) Acid substance weight%: Indicates the weight% of the acidic substance with respect to the compound (B) having an oxazolidine ring.

[0046]

[Table 2] Table 2. Formulation conditions and test results

Note) NCO / * H: Equivalent ratio of active hydrogen groups (amine and hydroxyl group) generated by hydrolysis of isocyanate groups and oxazolidine rings. Note) PTSI weight%: indicates the weight% of PTSI based on the compound (B) having an oxazolidine ring. Note) Acid substance weight%: Indicates the weight% of the acidic substance with respect to the compound (B) having an oxazolidine ring.

[0048]

[Table 3] Table 3. Formulation conditions and test results

Note) NCO / * H: Equivalent ratio of an isocyanate group and an active hydrogen group (amine and hydroxyl group) generated by hydrolysis of an oxasodidine ring. Note) PTSI wt%: indicates the wt% of PTSI relative to the compound (B) having an oxasodidine ring. Note) Acidic substance weight%: Indicates the weight percentage of the acidic substance with respect to the compound (B) having an oxasodidine ring.

[0050]

[Table 4] Formulation conditions and test results

Note) NCO / * H: Equivalent ratio of active hydrogen groups (amine and hydroxyl group) generated by hydrolysis of isocyanate groups and oxazolidine rings. Note) PTSI weight%: indicates the weight% of PTSI based on the compound (B) having an oxazolidine ring. Note) Acid substance weight%: Indicates the weight% of the acidic substance with respect to the compound (B) having an oxazolidine ring.

[0052]

According to the present invention, a polyurethane resin (A) having two or more isocyanate groups in the molecule, a compound (B) having two or more oxazolidine rings, a specific acidic substance (C),
-By using a composition comprising toluenesulfonyl isocyanate, the non-foaming property of the initial adjusted product (with or without foaming by carbon dioxide gas) and excellent tack-free time even under high temperature and high humidity (50 ° C x 50%), and , Non-foaming property after storage stability test, excellent tack free time, good curability, deterioration during elongation during heat treatment, that is, excellent heat resistance deterioration, and storage stability Good one
It is intended to provide a liquid room temperature-curable polyurethane resin composition and an adhesive using the present composition.

 ──────────────────────────────────────────────────続 き Continued on front page F term (reference) 4J034 BA02 BA08 CA01 CA22 CC03 CC12 CC33 CE04 DA01 DB03 DB04 HA01 HA02 HA06 HA07 HC03 HC12 HC13 HC22 KD12 RA07 RA08 4J040 EE051 EE052 EF131 EF132 EF272 EF321 EF322 GA19 HB12 HB27 HC05 LA LA08 NA12 NA16

Claims (7)

[Claims] 1. A polyurethane resin having two or more isocyanate groups in a molecule, (B) a compound having two or more oxazolidine rings in a molecule, (C) nitrobenzoic acid, and chlorobenzoic acid. Or one or more acidic substances selected from methoxybenzoic acid, or (D) 4
-Toluenesulfonyl isocyanate (hereinafter referred to as PTSI)
) As an essential component, a one-part room temperature-curable polyurethane resin composition. 2. A compound (B) comprising a polyurethane resin (b1) containing a polyoxyethylene chain in the molecule and having two or more isocyanate groups in the molecule, and N-2-hydroxyalkyloxazolidine (B). 2. The one-part room temperature-curable polyurethane resin composition according to claim 1, which is a compound having two or more oxazolidine rings in the molecule, obtained by reacting b2). 3. The method according to claim 1, wherein the amount of the acidic substance (C) used is in the range of 0.01 to 2.0% by weight based on the weight of the compound (B). The one-part room temperature-curable polyurethane resin composition according to any one of the above. 4. The method according to claim 1, wherein the amount of PTSI (D) used is in the range of 0.01 to 2.0% by weight based on the weight ratio to compound (B). The one-part room temperature-curable polyurethane resin composition according to claim 1. 5. An isocyanate of the polyurethane resin (A).
And an active hydrogen group (amine and hydroxyl group) generated by hydrolysis of the oxazolidine ring of compound (B)
And NCO / * H = 0.5 to
The one-part room temperature-curable polyurethane resin composition according to any one of claims 1 to 4, wherein the composition is in the range of 5.0. 6. The amount of the oxyethylene chain contained in the polyurethane resin (b1) is in the range of 1 to 10% by weight based on the total weight of the polyurethane resin (A) and the compound (B). The method according to any one of claims 1 to 5,
Liquid room temperature curable polyurethane resin composition. 7. An adhesive comprising the one-pack room-temperature-curable polyurethane resin composition according to any one of claims 1 to 6.