KR100444390B1 - Moisture Curable Polyurethane Compositions - Google Patents

Abstract

Moisture-curable polyurethane compositions having excellent storage stability and curability are disclosed. The moisture-curable polyurethane composition comprises a urethane prepolymer obtained by adding a specific oxazolidine to 5 to 60 mol% of isocyanate groups and the oxazolidine hydrolysis-promoting catalyst. Excellent and does not foam when cured

Description

Moisture Curable Polyurethane Compositions

The present invention relates to a moisture-curable polyurethane composition. More specifically, the present invention relates to a moisture-curable polyurethane composition having improved storage stability and curability, workability, high tensile strength, elasticity and stretchability as compared with conventional moisture-curable urethane compositions.

Urethane compositions are known to have excellent tensile and tear strengths and have high extensibility and good wear resistance, impact resistance, weather resistance and chemical resistance. Due to these properties, the urethane composition is used as a special coating agent in the textile, paper, automobile, sports, wood and construction, marine, and industrial repair markets. In particular, as a civil engineering and construction, the polyurethane composition has excellent physical properties such as chemical resistance, chemical resistance, and sound absorption as well as adhesion to concrete surface, and in particular, due to the advantage of elasticity and extensibility, The demand is increasing with the inner, outer wall and floor waterproofing materials. Usually, the two-component polyurethane composition is composed of a main component mainly composed of a urethane prepolymer and a curing agent component composed of an active hydrogen compound. Polyurethanes in waterproofing applications include the main components of the urethane prepolymers obtained by the reaction of polyoxypropylene polyols with toluene diisocyanate, and a curing agent component composed mainly of polyols and 4,4'-methylene bis (2-chloroaniline). The two-component polyurethane composition of the mainstream. Usually, the two-component polyurethane composition should be used after stirring within a limited pot life, so that the time interval between stirring and construction should be well controlled, and if this time is not correct, the amount of material loss increases. In addition, the water in the base and the water in the atmosphere participate in the reaction with the urethane prepolymer, and compete with the curing agent component mainly composed of polyol and 4,4'-methylene bis (2-chloro aniline). Therefore, moisture may delay the curing process of the urethane coating film or cause partial curing, reduce surface gloss and decrease performance. In addition, the reaction between water and the urethane prepolymer generates carbon dioxide gas that can induce bubble formation in the coating film. Bubbles formed in the coating film by the above reaction typically cannot move along the surface of the coating film, and thus can produce fine pores in the coating film. These fine pores are undesirable because they increase the permeability of the coating to water, which lowers the corrosion protection ability. These fine pores also impair the physical integrity of the coating, resulting in low tensile strength and reducing elongation and wear resistance.

Thus, one-part formulation of polyurethane compositions that complements the drawbacks of two-parts in order to maintain excellent physical and chemical properties of polyurethane compositions has been studied. Examples thereof include a method of forming a one-component polyurethane composition by adding a filler, a stabilizer, a coloring agent, etc. to a urethane prepolymer having an isocyanate group (NCO) weight% content of about 1 to 5%. However, this method has a disadvantage in that curing at room temperature is slow and storage stability is reduced even by slight moisture, and phenomena such as swelling of the coating film are caused by carbon dioxide generated by the reaction of water and isocyanate. Complementing this disadvantage is the mixing of ingredients such as ketamine and aldimine. Ketamine and aldimine are Schiff's salts derived from ketones or aldehydes, respectively. As well as mono, di- or polyoxazolidine and the like. Upon exposure to water, oxazolidine hydrolyzes to form hydroxyl amines, while ketimines and aldimines produce amines and corresponding ketones or aldehydes. The resulting hydroxyl amine and the like thus react with the isocyanate prepolymer to form a polyurethane coating. Hydrolysis of ketimines, aldimines, and oxazolidines with isocyanates such as hydroxyl amines is faster than the rate at which water reacts with isocyanates, thereby suppressing the formation of bubbles due to carbon dioxide generation. However, this method has a problem that it is unsuitable to use during the waterproofing of the building film during the summer due to the high reactivity in high temperature and high humidity environment. That is, the hardening of the coating film proceeds quickly, but it is difficult to penetrate the inside of the coating film, so that the hardening speed is lowered. Thus, when the polyurethane composition of the above method is used for building coating waterproofing, it is inconvenient to repaint two or three times in order to maintain a constant coating thickness (2 to 3 mm).

Accordingly, an object of the present invention is to solve the problems of the prior art as described above and to provide a moisture-curable polyurethane composition excellent in storage stability and curability.

In order to achieve the above object, the present invention has to solve the conventional disadvantages of the moisture-curable polyurethane resin composition in the case of using oxazolidine as a potential curing agent, and potential urethane prepolymer synthesized by adding a specific oxazolidine. As a curing agent, p-toluene sulfonyl isocyanate derivative was used as a curing catalyst to obtain a moisture-curable polyurethane composition having excellent curability even in a thick film and greatly improving storage stability.

That is, the present invention, by adding the oxazolidine of the formula (1) or (2) below to the urethane prepolymer is a reactant of 5 to 60 mol% of the isocyanate group of the urethane prepolymer is blocked; And it provides a moisture-curable polyurethane composition comprising 0.1 to 10 parts by weight of the compound for promoting hydrolysis of the oxazolidine based on 100 parts by weight of the blocked reactant.

(Wherein R ₁ is either an alkyl group having 1 to 18 carbon atoms or a hydroxyalkyl group, and n represents 1 or 2)

(Wherein R ₂ is either an alkyl group of 1 to 18 carbon atoms or hydrogen, and R ₃ represents hydrogen)

Hereinafter, each compound contained in the composition of the present invention will be described. As for the urethane prepolymer which added the specific oxazolidine used for this invention, 5-60 mol% of the isocyanate group (NCO) is the hydroxyl group (OH) of the specific oxazolidine represented by the said compound (1) and or (2). Reacted and blocked. The conventional method is a moisture-curable polyurethane resin composition containing oxazolidine as a latent curing agent is formulated separately into the composition without reacting the oxazolidine and the urethane prepolymer in advance, but the present invention provides the oxazolidine and urethane prepolymer as described above. Is reacted in advance to block the isocyanate group with a hydroxyl group of oxazolidine. As such, addition reaction between the oxazolidine and the urethane prepolymer has the advantage of not only suppressing foaming during curing but also easily adjusting the curability without changing physical properties.

The urethane prepolymer of the present invention subjected to the above addition reaction is generally a urethane prepolymer which is a reaction product of a polyol compound and an excess of a polyisocyanate compound (i.e., an excess of NCO groups relative to an OH group), similarly to a prepolymer used in a conventional one-component polyurethane resin. As such, containing from 0.5 to 10% by weight of isocyanate groups.

As a polyisocyanate compound which produced such a urethane prepolymer, what can be used for a normal one-component polyurethane resin composition is illustrated variously, Specifically, 2, 4- toluene diisocyanate, 2, 6-toluene diisocyanate, 4 Aromatic polyisocyanates such as, 4'-diphenyl methane diisocyanate, 2,4'-diphenyl methane diisocyanate and polymethylene polyphenylene polyisocyanate; Aliphatic polyisocyanates such as hexamethylene diisocyanate; Alicyclic polyisocyanates such as isophorone diisocyanate; Aryl aliphatic polyisocyanates such as xylene diisocyanate; Carboxylimide-modified or isocyanurate-modified polyisocyanate etc. of each said polyisocyanate are mentioned, It is used as such 1 type, or 2 or more types of combination.

The polyol compound is usually a polyether polyol, a polyester polyol, other polyols and mixed polyols thereof similarly to the one-component polyurethane resin composition. Specifically polyether polyols include ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, glycerin, 1,1,1-trimethylol propane, 1,2,5-hexatriol, 1,3-butanediol, 1 One or two or more propylene oxides, ethylene oxides, butylenes of polyhydric alcohols, such as, 4-butanediol, 4,4'-dihydroxy phenyl propane, 4,4'-dihydroxy phenylmethane and pentaerytolrol Polyol obtained by adding 1 type, or 2 or more types, such as an oxide and a styrene oxide; Polyoxy tetramethylene oxide, and the like.

As the polyester polyol, one or two or more of ethylene glycol, propylene glycol, butanediol, pentane diol, hexane diol, cyclohexane dimethanol, glycerin, 1,1,1-trimethylolpropane, or other low molecular polyols; Polycondensation reactants with one or two or more of glutaric acid, adipic acid, pimarin acid, sebatic acid, terephthalic acid, isophthalic acid, dimer acid or other low molecular carboxylic acid or oligomeric acid; Ring-opening polymers, such as a fururion lactone, a valerolactone, and a caprolactone, etc. are mentioned.

Other polyols include polymer polyols, polycarbonate polyols, polybutadiene polyols, hydrogenated polybutadiene polyols, acrylic polyols, and the like ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, butanediol, pentanediol, hexanediol and the like. And low molecular polyols. As the polyol compound used for the urethane prepolymer, among these, polypropylene glycol, polyethylene glycol and the like are preferable in terms of cost. The number average molecular weight of the polyol compound used for the urethane prepolymer is 1000-10000, and about 2000-7000 are especially preferable.

In the process of obtaining a urethane prepolymer composed of such a polyol compound and an excess polyisocyanate compound, the mixing ratio of the polyol compound and the polyisocyanate compound is generally 1 equivalent (OH equivalent) to the polyol compound 1.2 to 5.0 equivalents (NCO equivalent). And the preferred one is 1.5 to 3.0 equivalents. The urethane prepolymer is prepared in the same manner as in the conventional urethane prepolymer by mixing the two compounds in a certain amount ratio and heating and stirring to 30 to 120 ° C, preferably 50 to 100 ° C.

Oxazolidine used in the present invention is a compound of Formula 1 and a compound of Formula 2. Oxazolidine of the present invention is condensation reaction of aldehyde monomer with hydroxyalkylaminoalcohol in the equivalence ratio, and removes the water produced by using a circulating solvent, and after the reaction proceeds to 95% vacuum decompression and circulating with the remaining aldehyde without reacting Oxazolidine is prepared by removing the solvent, water and the like. Hydroxyalkylaminoalcohols used herein include 2-((hydroxymethyl) amino) ethanol, 2- (2- (hydroxyethyl) amino) ethanol, 2- (2- (hydroxypropyl) amino) ethanol And hydroxyalkylaminoalcohols such as 2- (2- (hydroxyethyl) amino) isobutanol and 2- (2- (hydroxypropyl) amino) isopropanol. In addition, aldehyde monomers used herein include benzylaldehyde, o-tolualdehyde, m-tolualdehyde, p-tolualdehyde, 4-ethyl benzylaldehyde, 4-propyl benzylaldehyde, 4-butyl benzylaldehyde, 2,4- Aromatic aldehydes such as dimethyl benzylaldehyde, 2,4,5-trimethyl benzylaldehyde, 2-methoxy benzylaldehyde, p-ethoxy benzylaldehyde, formaldehyde, acetaldehyde, propionaldehyde, butylaldehyde, pentylaldehyde, hexylaldehyde, etc. Aliphatic aldehydes.

Oxazolidine used in the present invention acts as a potential curing agent that ring-opens in the presence of moisture to react with isocyanates to cure the urethane prepolymer. In the present invention, since oxazolidine blocks 5 to 60 mol% of the isocyanate groups in the urethane prepolymer in advance, not only the foaming during curing can be suppressed but also the curing property can be adjusted without changing the physical properties. Curability of the urethane prepolymer with oxazolidine can be controlled according to the oxazolidine represented by the compound 1 or 2 which is blocking the urethane prepolymer. That is, the use of an oxazolidine having an aliphatic group can shorten the curing time, and the use of an oxazolidine having an aromatic group can make the curing time slower than when using an oxazolidine having an aliphatic group. Therefore, the curing time of the polyurethane resin composition can be adjusted by combining such oxazolidines or changing the blocking rate of the isocyanate groups of the urethane prepolymer by such oxazolidines. For example, summer can increase curing time and winter can shorten curing time.

The oxazolidine represented by Formula 1 or 2 is preferably added in an amount of 5 to 60 mol%, particularly 20 to 50 mol%, based on the isocyanate group of the urethane prepolymer. If it is less than 5 mol%, unreacted isocyanate groups will increase, and the curability of the urethane prepolymer to which oxazolidine is added worsens. If it is 60 mol% or more, unreacted oxazolidine which does not act as a crosslinking agent will increase, resulting in curing. After the coating film properties are deteriorated, storage stability is poor. It is preferable to make reaction of oxazolidine and a urethane prepolymer react at room temperature-80 degreeC, especially 40-60 degreeC for 1-3 hours.

It is preferable to use p-toluene sulfonyl isocyanate derivative as a compound for promoting oxazolidine hydrolysis used in the present invention. This derivative is obtained by adding active hydrogen in a compound containing active hydrogen to an isocyanate group of p-toluene sulfonyl isocyanate. Herein, active hydrogen refers to a hydrogen atom bonded to a carbon bonded to at least two or more hydrogen atoms bonded to N, O, etc. having a high electronegativity, and -O-, -OR, etc. having high electron withdrawing properties. The derivative of p-toluene sulfonyl isocyanate used in the present invention is a compound for promoting oxazolidine hydrolysis, and hydrolysis of oxazolidine in the presence of moisture at room temperature in the above moisture curable compound comprising urethane prepolymer and oxazolidine. It acts to promote. For this reason, by containing p-toluene sulfonyl isocyanate derivative, the composition of this invention has the advantage that sclerosis | hardenability is improved and storage stability is improved. In the present invention, compounds such as p-toluene sulfonyl isocyanate and active hydrogen compounds are not added directly to the oxazolidine and the addition urethane prepolymer, but are added to the p-toluene sulfonyl isocyanate derivative, so that the active hydrogen compound reacts with the urethane prepolymer. I never do that.

Examples of the oxazolidine hydrolysis-promoting compound of the present invention include active hydrogen compounds such as p-toluene sulfonyl isocyanate and alcohols, thiols, amines, amides and ethers; Epoxy; Esters; Acetals; Alternatively, it can be synthesized by reaction with an active methylene compound. In particular, it is preferable to make p-toluene sulfonyl isocyanate react with alcohols because it is excellent in storage stability. Specific examples of such compounds include active hydrogen compounds such as ethyl alcohol, 2-cyano ethyl alcohol, 2-chlorohydrin, 2,2'-trichloroethyl alcohol, butanediol, hexylamine, stearic acid amide, and phenyl glycidyl ether; Esters such as methyl formate; Active methylene compounds, such as acetals, such as cyclohexanone dimethyl acetal, are mentioned.

Among them, 2-cyano ethyl alcohol, methyl formate, and cyclohexanone dimethyl acetal are particularly preferable in terms of storage stability. In the present invention, the blending amount of the curing catalyst is preferably 0.1 to 10 parts by weight, in particular 0.1 to 5 parts by weight, based on 100 parts by weight of the urethane prepolymer. In order to fully accelerate hardening of a composition, 0.1 weight part or more is preferable, and it is preferable in storage stability that it is 10 weight part or less.

The composition of the present invention may be blended with various additives such as pigments or dyes, fillers, antisettling agents, antistatic agents, flame retardants, plasticizers, antioxidants, dispersants, and solvents, depending on the use, in addition to the above compounds which are essential components.

Examples of the filler include calcium carbonate, talc, silica, barium sulfate, kaolin, clay and the like. It is preferable that the addition amount of a filler is 10-150 weight part with respect to 100 weight part of urethane prepolymers from a physical property, such as workability and curability. Examples of the plasticizer include phthalic acid esters such as dioctyl phthalate, dibutyl phthalate, dimethyl phthalate, and diethyl phthalate, adipic acid dioctyl, and dioctyl sebacate. It is preferable that the addition amount of a plasticizer is 5-100 weight part with respect to 100 weight part of urethane prepolymers from the viscosity of a composition.

Solvents used for viscosity adjustment include ketones such as methyl ethyl ketone and acetone, aromatic hydrocarbons such as toluene and xylene, petroleum solvents such as mineral spirits, or 5-20% by weight of cellulose solvents, cellulose solvents, etc. It can be used within and is preferably used in the range of 10-15% by weight.

The method for preparing the composition of the present invention is not limited, but an oxazolidine-added urethane prepolymer prepared by condensing the hydroxyalkylamino alcohol and aldehyde, a p-toluene sulfonyl isocyanate derivative, and an oxazolidine hydrolysis promoting compound, Alternatively, if necessary, the blended additive is suitably added, mixed and stirred, followed by vacuum degassing, and then packaged and sealed in a container filled with dry nitrogen.

Although an Example is given to the following and this invention is demonstrated concretely, this invention is not limited at all by the following example.

Synthesis of oxazolidine

Synthesis Example 1

A 2-liter four-necked flask was equipped with a thermometer, condenser, stirrer, moisture removal condenser and temperature raising device. 100 g of toluene, 107 g of benzylaldehyde, and 105 g of 2- (2- (hydroxyethyl) amino) ethanol were added thereto, and the temperature was raised to 110 ° C. The condensation reaction was carried out by circulation with toluene while recovering water. When the amount of recovered water reached 95% of theory, oxazolidine was synthesized by vacuum decompression to remove unreacted material, toluene and water.

Synthesis Example 2

Example 2 was prepared in the same manner as in Example 1, and 44 g of acetaldehyde was used as the aldehyde.

Synthesis Example 3

Example 3 was carried out in the same manner as in Example 1, and 72 g of butylaldehyde was used as the aldehyde.

Synthesis Example 4

Example 4 was prepared in the same manner as in Example 1, and 136 g of 2-methoxy benzylaldehyde was used as the aldehyde.

<Isocyanate Prepolymer Synthesis>

Synthesis Example 5

After a 2-liter four-necked flask was equipped with a stirrer, a nitrogen injection tube, and a thermometer, 100 g of dioctylphthalate, 350 g of polypropylene glycol having a number average molecular weight of 3000, 375 g of polypropylene triol having a number average molecular weight of 3000, 15 g of 1,3-butanediol and toluene 202 g of isocyanate was reacted at 80 ° C. for 8 hours to obtain a urethane prepolymer having a content percentage of isocyanate groups of 5.6%.

<Addition reaction of oxazolidine and isocyanate prepolymer>

Synthesis Examples 6-9

A certain amount of oxazolidine (Synthesis Examples 1 to 4) was added to the urethane prepolymer of Synthesis Example 5 and reacted at 50 ° C. for 3 hours. The molar% blocked isocyanate relative to the obtained oxazolidine-added urethane prepolymer is shown in Table 1 below in terms of percent blockage (%).

Synthesis Example 6 Synthesis Example 7 Synthesis Example 8 Synthesis Example 9 Synthesis Example 1 97 - - - Synthesis Example 2 - 74.5 - - Synthesis Example 3 - - 88.5 - Synthesis Example 4 - - - 120.5 Synthesis Example 5 750 750 750 750 NCO containment rate (%) 50 50 50 50

EXAMPLES 1-6

Calcium carbonate, a solvent, a plasticizer, an antisettling agent, etc. were added together to 300 g of the urethane prepolymer (Synthesis Examples 6-9) to which the oxazolidine obtained as mentioned above was added, and it stirred and mixed at room temperature for about 30 minutes. The p-toluene sulfonyl isocyanate derivative, which is a compound for promoting oxazolidine hydrolysis, was prepared by mixing p-toluene sulfonyl isocyanate and methyl formate in a 1: 5 weight ratio. A curing catalyst, an antifoaming agent, and an antioxidant were added to the mixture, and the mixture was sufficiently mixed, and then degassed under vacuum at room temperature to obtain a moisture-curable polyurethane composition.

The raw materials and contents used in Table 2 below are shown.

[Comparative Examples 1 and 2]

To the isocyanate prepolymer (Synthesis Example 5) was prepared by adding Incozol LV (manufactured by ICL), which is an oxazolidine latent curing agent. To prepare a moisture-curable one-component polyurethane composition in the same manner as in Example 1 using the raw materials as shown in Table 2.

Example Comparative example One 2 3 4 One 2 Synthesis Example 6 Synthesis Example 7 Synthesis Example 8 Synthesis Example 9 Synthesis Example 5Incosol LV calcium xylene suspending agent defoamer catalyst ^{week 1)} DBTDL ^{Note 2)} 100 ----- 100101.01.51.0- -100 ---- 100101.01.51.0- --100 --- 100101.01.51.0- --- 100--100101.01.51.0- ---- 10012100101.01.51.0- ---- 10012100101.01.51.00.2

Note 1) p-toluene sulfonyl isocyanate derivative

Note 2) Dibutyl Tin Dilaurate

[Property Test]

Measurement of the physical properties of the moisture-curable polyurethane composition obtained in Examples 1 to 4 and Comparative 1 and 2 was prepared by the test specimen according to the KSF-3211 and KSF-6518 method to measure the tensile strength, tear strength, elongation, etc. KSF-4910 According to the method, the drying time was measured. In addition, the storage stability measured the initial viscosity of the obtained moisture-hardenable polyurethane composition using the Brookfield viscometer. Furthermore, after leaving for 24 hours at 60 degreeC with respect to this composition, a viscosity was measured, the ratio with an initial viscosity was calculated | required, and the rise rate of a viscosity was calculated | required. Curability evaluation according to the coating film thickness was coated on a 20cm × 30cm slate plate with 1 mm, 2 mm, and 3 mm, respectively, and left at room temperature for 24 hours to evaluate the cured film state. This evaluated whether the surface and the inside of the cured coating film were uniformly cured.

The results are shown in Table 3 below.

Example Comparative example One 2 3 4 One 2 Tensile strength (kgf / ㎠) 43 37 40 41 31 34 Tear strength (kgf / cm) 20 15 17 16 10 12 Elongation (%) 450 380 410 470 340 280 Tag free (time) 5 3 4 7 15 10 Storage stability 1.0 1.1 1.1 1.0 1.0 1.1 Curable 1 mm ◎ ◎ ◎ ◎ O ◎ 2 mm ◎ O O ◎ X O 3 mm O △ O O X X

◎: Excellent, O: Good, △: Normal, X: Poor

The moisture-curable polyurethane composition of the present invention is excellent in storage stability, excellent in curability even in thick film coating, and does not foam upon curing. Depending on the type of aldehyde substituted with oxazolidine as a potential curing agent, the curability can be controlled in a wide range without affecting the physical properties of the cured coating film.

Although the present invention has been described above according to an embodiment of the present invention, it will be apparent to those skilled in the art that various modifications may be made without departing from the spirit of the present invention.

Claims (9)

A reactant formed by addition reaction of a urethane prepolymer and an oxazolidine represented by Formula 1 or Formula 2 below, containing 5 to 60 mol% of isocyanate groups of the urethane prepolymer; And Moisture-curable polyurethane composition comprising 0.1 to 10 parts by weight of the compound for promoting hydrolysis of the oxazolidine based on 100 parts by weight of the blocked reactant. [Formula 1] (Wherein R ₁ is either an alkyl group having 1 to 18 carbon atoms or a hydroxyalkyl group, and n represents 1 or 2) [Formula 2] (Wherein R ₂ is either an alkyl group having 1 to 18 carbon atoms or hydrogen, and R ₃ represents hydrogen) The moisture-curable polyurethane composition according to claim 1, wherein the oxazolidine is prepared by reacting hydroxyalkylamino alcohol with aldehyde. The hydroxyalkylamino alcohol according to claim 2, wherein 2-((hydroxymethyl) amino) ethanol, 2-((hydroxyethyl) amino) ethanol, 2- (2- (hydroxypropyl) amino) ethanol And at least one selected from the group consisting of 2- (2- (hydroxyethyl) amino) isobutanol and 2- (2- (hydroxypropyl) amino) isopropanol. The method of claim 2, wherein the aldehyde is benzylaldehyde, o-tolualdehyde, m-tolualdehyde, p-tolualdehyde, 4-ethyl benzylaldehyde, 4-propyl benzylaldehyde, 4-butyl benzylaldehyde, 2,4-dimethyl Aromatic aldehydes such as benzylaldehyde, 2,4,5-trimethyl benzylaldehyde, 2-methoxy benzylaldehyde and p-ethoxy benzylaldehyde, formaldehyde, acetaldehyde, propionaldehyde, butylaldehyde, pentyl aldehyde, hexyl aldehyde, etc. Moisture-curable polyurethane composition, characterized in that at least one selected from the group consisting of aliphatic aldehyde. The method of claim 1, wherein the urethane prepolymer is an aliphatic or aromatic diisocyanate, a modified isocyanate, a polymeric isocyanate or a polyether polyol, a polyester polyol, a hydroxyl polycarbonate of a dihydric or trihydric alcohol and an isocyanate selected from them. Moisture-curable polyurethane composition, characterized in that the content of the isocyanate group is 2 to 10% as a prepolymer obtained by the reaction of a single or a mixture thereof. The compound for promoting oxazolidine hydrolysis according to claim 1, wherein p-toluene sulfonyl isocyanate and Active hydrogen compounds such as ethyl alcohol, 2-cyano ethyl alcohol, 2-chloro hydrin, 2, 2'-trichloro ethyl alcohol, butanediol, hexylamine, stearic acid amide, and phenyl glycidyl ether; Esters such as methyl formate; Active methylene compounds such as acetals such as cyclohexanone dimethyl acetal; The moisture-curable polyurethane composition which is a mixture with any one of these. The moisture-curable polyurethane composition according to claim 1, wherein the compound for promoting hydrolysis is blended at a ratio of 0.1 to 10 parts by weight based on 100 parts by weight of the reactant. A reactant formed by addition reaction of a urethane prepolymer and an oxazolidine represented by the following Chemical Formula 1 or Chemical Formula 2, containing 5 to 60 mol% of isocyanate groups of the urethane prepolymer; And It comprises 0.1 to 10 parts by weight of the compound for promoting hydrolysis of the oxazolidine based on 100 parts by weight of the blocked reactant, At least one selected from calcium carbonate, talc, silica, barium sulfate, clay as the filler is included in the range of 30 to 60% of the total formulation, Moisture-curable polyurethane flooring agent containing a suitable amount of a coloring agent, a plasticizer, and an additive. [Formula 1] (Wherein R ₁ is either an alkyl group having 1 to 18 carbon atoms or a hydroxyalkyl group, and n represents 1 or 2) [Formula 2] (Wherein R ₂ is either an alkyl group having 1 to 18 carbon atoms or hydrogen, and R ₃ represents hydrogen) A reactant formed by addition reaction of a urethane prepolymer and an oxazolidine represented by the following Chemical Formula 1 or Chemical Formula 2, containing 5 to 60 mol% of isocyanate groups of the urethane prepolymer; And It comprises 0.1 to 10 parts by weight of the compound for promoting hydrolysis of the oxazolidine based on 100 parts by weight of the blocked reactant, At least one selected from calcium carbonate, talc, silica, barium sulfate, clay as the filler is included in the range of 30 to 60% of the total formulation, Moisture-curable polyurethane waterproofing agent containing a suitable amount of a coloring agent, a plasticizer, and an additive. [Formula 1] (Wherein R ₁ is either an alkyl group having 1 to 18 carbon atoms or a hydroxyalkyl group, and n represents 1 or 2) [Formula 2] (Wherein R ₂ is either an alkyl group having 1 to 18 carbon atoms or hydrogen, and R ₃ represents hydrogen)