JPH09278857A - Moisture-curable urethane composition and coating material - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a moisture-curing urethane composition excellent in foamability, curability, and heat deterioration resistance, and a coating material. SOLUTION: The composition comprises as essential components a urethane prepolymer having two or more terminal isocyanate groups, a compound having two or more oxazolidine rings per molecule, and an acid substance having a dissociation constant, pKa, of 1.0-4.0. A coating material is also provided.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a one-pack type moisture curable polyurethane composition utilizing a reaction of hydrolyzing an oxazolidine ring excellent in heat deterioration resistance and curability with moisture in the air to generate active hydrogen. It is industrially useful as a coating material for construction or vehicles.

[0002]

2. Description of the Related Art Various one-pack type moisture-curable polyurethanes have been investigated, but most of them are produced by reaction of polyisocyanate with moisture (moisture), that is, carbon dioxide gas of an adduct of isocyanate and moisture. A part of the polyisocyanate becomes an amine, and the produced amine reacts with the rest of the polyisocyanate to cure the polyisocyanate, which causes foaming of the molded product due to the generation of carbon dioxide gas. Further, since the curing speed is slow, when a curing accelerator such as a metal catalyst and an amine catalyst is used in combination, the foaming phenomenon tends to be worse.

For example, Japanese Patent Application Laid-Open No. 7-289989 utilizes that a cross-linking agent composed of an alicyclic enamine derivative is hydrolyzed by moisture (moisture), and the resulting amine reacts with polyisocyanate to cure. A moisture-curable polyurethane composition that is non-foaming and excellent in curability is 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 that is a curing accelerator.

However, the moisture-curable polyurethane composition described in JP-A-7-289989 is characterized by being non-foaming and excellent in curability, but in order to increase the curing rate, a large amount of acidity is required. There is a problem that a catalyst (curing accelerator) is required, and as a result, stress relaxation of the cured coating film occurs during heat treatment, which adversely affects the cured physical properties. For example, when this is used for the urethane rubber-based waterproof material described in JIS-A6021, if the composition has a fast curing property containing a large amount of an acidic catalyst, it is significantly deformed in the item "deterioration property during elongation by heat treatment" ( Stress relaxation), it was difficult to develop it as a waterproof material.

A one-pack moisture-curable urethane composition using an oxazolidine compound as a cross-linking agent is disclosed in JP-A-6-2.
It is proposed in Japanese Patent Laid-Open No. 93821, Japanese Patent Laid-Open No. 7-33852, Japanese Patent Laid-Open No. 7-10949, and the like.

However, in JP-A-6-293821, a composition comprising only a compound obtained by reacting a urethane prepolymer containing no oxyethylene chain and N-2-hydroxyalkyloxazolidine in a large excess of isocyanate groups is used. There was a problem with the curability.

On the other hand, in Japanese Patent Laid-Open No. 7-33852,
Since a mixture of an organic diisocyanate such as xylylene diisocyanate or hexamethylene diisocyanate and a hydroxyoxazolidine compound is mixed with an NCO-terminated urethane prepolymer, the coating workability is good, but the curability is poor. is there.

Further, JP-A-7-10949 discloses a mixture of an NCO group-containing urethane prepolymer having an oxyethylene chain and a reaction product of tolylene diisocyanate and a hydroxyoxazolidine compound. It is inferior in curability.

[0009]

The object of the present invention is to provide a moisture-curing composition which does not cause foaming during curing, has good curability, and does not undergo deterioration during elongation by heat treatment, that is, is excellent in heat-deterioration. To provide a hydrophilic urethane resin composition.

[0010]

Means for Solving the Problems The present inventors have conducted extensive studies on the above problems, and as a result, by using a compound having an oxazolidine ring, particularly a urethane oxazolidine prepolymer having an oxyethylene chain and a specific acidic catalyst,
JP-A-6-293821, JP-A-7-10949
As described in JP-A No. 7-
Compared to the case of the alicyclic enamine derivative of 289989, a small amount of acidic catalyst is effective, so that a coating film which is excellent in thermal deterioration without elongation deterioration during heat treatment, that is, stress relaxation can be obtained. As a result, they have completed the present invention.

That is, the present invention provides (A) a urethane prepolymer having two or more isocyanate groups at the terminal,
(B) A compound having two or more oxazolidine rings in the molecule and (C) an acidic substance having an acid dissociation index pKa of 1.0 to 4.0 as essential components, a moisture-curable urethane. The composition, preferably the compound (B), has an oxyethylene chain and has a terminal oxazolidine obtained by reacting a urethane prepolymer (b1) having two or more isocyanate groups at the terminal with N-2-hydroxyalkyloxazolidine. A urethane prepolymer having two or more groups, an isocyanate group of the compound (A),
The ratio of active hydrogen H (primary amine and hydroxyl group) generated by hydrolyzing the oxazolidine ring of compound (B) is an equivalent ratio of -NCO / -H = 0.4 to 4.0; The acidic substance (C) is selected from the group of inorganic acids, organic acids and their anhydrides, esterified products, acidic salts 1
One or more kinds, the acidic substance (C) is one or more selected from phosphoric acid, acidic phosphoric acid ester, salicylic acid, phosphate or phthalic anhydride, and the acid of the acidic substance (C) is a compound The equivalent ratio to the active hydrogen H (primary amine and hydroxyl group) generated by hydrolyzing the oxazolidine ring of (B) is in the range of 0.005 to 0.1, preferably containing an oxyethylene chain. The amount is less than 6% by weight based on the total amount of the components (A) and (B), and a coating material comprising the moisture-curable urethane composition is provided.

The present invention will be further described below.

[0013]

BEST MODE FOR CARRYING OUT THE INVENTION

The compound (b1) having two or more isocyanate groups at the terminals used as a raw material for the urethane prepolymer (A) having two or more terminal isocyanate groups and the compound (B) used in the present invention is Both are compounds having two or more isocyanate groups, and are organic polyisocyanates themselves, or urethane prepolymers prepared by a conventional method in the presence of an excess of organic polyisocyanates and polyols.

As the organic polyisocyanate, 2,4
-Tolylene diisocyanate, 2,6-tolylene diisocyanate, diphenylmethane diisocyanate, partially carbodiimidated diphenylmethane diisocyanate, polymethylene polyphenyl polyisocyanate, tolidine diisocyanate, naphthalene diisocyanate, phenylene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, xylylene Examples thereof include aromatic diisocyanates such as diisocyanate, hydrogenated xylylene diisocyanate, hydrogenated diphenylmethane diisocyanate, and cyclohexane diisocyanate, aliphatic diisocyanates, alicyclic diisocyanates, and mixtures of two or more thereof.

The polyols used in the present invention are polyether polyols, polyester polyols, other polyols and mixed polyols thereof. For example, a polyol produced by using a complex metal cyanide compound complex as a catalyst is also included.

As the polyether polyol, one or more polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, glycerin, trimethylolpropane, glucose, sorbitol and sucrose are added to propylene oxide and ethylene. Examples thereof include polyols and polyoxytetramethylene polyols obtained by adding one kind or two or more kinds of oxides, butylene oxides, styrene oxides and the like.

As the polyester polyol, for example, one or two of ethylene glycol, propylene glycol, butanediol, pentanediol, hexanediol, cyclohexanedimethanol, glycerin, trimethylolpropane or other low molecular weight polyols is used.
And one or more of glutaric acid, adipic acid, pimelic acid, suberic acid, sebacic acid, terephthalic acid, isophthalic acid, dimer acid, hydrogenated dimer acid or other low molecular weight dicarboxylic acid or oligomer acid. Examples thereof include condensation polymers and ring-opening polymers such as propiolactone, caprolactone and valerolactone.

Other polyols include, for example, polycarbonate polyols, polybutadiene polyols,
Examples thereof include hydrogenated polybutadiene polyol and acrylic polyol. In addition, ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, butanediol, pentanediol,
Low molecular weight polyols such as hexanediol, cyclohexanedimethanolglycerin, trimethylolpropane, glucose, sorbitol and sucrose are also included.

The polyol as the component (A) is preferably a polyether polyol having a number average molecular weight of 500 to 16000 and preferably containing no oxyethylene chain. More preferred are polyether diols and / or polyether triols. When a polyol containing an oxyethylene chain is used as the component (A), the amount of the oxyethylene chain of the component (B) is calculated, and the content of the oxyethylene chain of the composition is the same as that of the components (A) and (B). It is preferably less than 6% by weight relative to the total amount.

The number of terminal isocyanate groups of the urethane prepolymer (A) is preferably 2 or more, more preferably 2
~ 3. NC of isocyanate and polyol
The O / OH ratio is preferably 1.4 or more, more preferably 1.4 to 5.0. The residual NCO% is preferably 1
-20% by weight.

The compound (B) having two or more oxazolidine rings in the molecule is obtained by reacting the compound (b1) having two or more isocyanate groups with the oxazolidine compound (b2).

When the compound (B) uses a urethane prepolymer as the isocyanate compound as the compound (b1), it preferably has a number average molecular weight of 500 to 8000. When the molecular weight is less than 500, there is a problem in the followability to the substrate, and when the molecular weight exceeds 8000, there is a problem that the curing rate is lowered. Further, the average number of NCO groups at the terminals of the urethane prepolymer (b1) is preferably 2.0 to 2.6.

If it is less than 2.0, the curability tends to decrease, and if it exceeds 2.6, the underlayer followability tends to decrease. Furthermore, NCO / of isocyanate and polyol
The OH ratio is preferably 1.6 or more, more preferably 1.8.
４4.0. The residual NCO% is preferably 1 to 15
% By weight.

The urethane prepolymer (b1) and N-
The reaction ratio with the 2-hydroxyalkyloxazolidine (b2) is preferably NCO / OH = 0.98 to 1.4,
More preferably, 1.02 to 1.15 are preferable. NCO
When / 0H is less than 0.98, N-2-hydroxyalkyloxazolidine tends to remain unreacted, which adversely affects storage stability. When NCO / OH = 1.4 is exceeded, the prepolymer having one oxazolidine group in the molecule increases, and there is a problem that the curing rate decreases and the viscosity increases.

N-2-used for the synthesis of compound (B)
Hydroxyalkyloxazolidine is synthesized by dehydration reaction of alkanolamines having a 1,2-amino group and a 2-hydroxyethyl group with aldehydes or ketones. 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,
It is a compound having a secondary amino-2-hydroxyl group in which a primary amino group such as phenylenediamine is substituted with a 2-hydroxyethyl group.

Examples of aldehydes or ketones include butyraldehyde, trimethylacetaldehyde, triethylacetaldehyde, valeroaldehyde, furfural, benzaldehyde, methylethylketone, cyclohexanone, trimethylcyclohexanone, acetophenone, anisaldehyde, hexanal, octanal,
Examples include decanal and citral.

The compounding ratio of the urethane prepolymer (A) and the compound (B) is such that the ratio of the NCO group of the prepolymer (A) and the active hydrogen group generated by ring-opening of the compound (B) with water is 0. The range of 4 to 4.0 is preferable. More preferably,
It is 0.5 to 2.0. If it is more than 4.0, the coating film tends to swell due to the generation of carbon dioxide gas and the curing is slow, and if it is less than 0.4, the elasticity of the coating film is lowered and sufficient coating film strength is exhibited. It will be difficult. Considering these points, the mixing ratio of (A) and (B) is 27: 1 to 1:16 by weight.
Is preferred.

The acidic substance (C) used in the present invention has an acid dissociation index pKa in an aqueous solution in the range of 1.0 to 4.0. Acid dissociation index p in aqueous solution of acidic substance (C)
When Ka is more than 4.0, hydrolysis of the oxazolidine ring of the compound (B) does not occur at a practical rate, so that the moisture curing rate is slow and foaming occurs in the cured product. When the acid dissociation index pKa in the aqueous solution of the acidic substance (C) is less than 1.0, a stable salt is formed with the amino group generated by the hydrolysis of the oxazolidine ring, and the reaction with isocyanate does not proceed. As a result, the moisture curing rate is slow and the physical properties of the cured product are significantly impaired.

The acid dissociation index pKa is an index indicating the acid strength, and the lower the value, the higher the acid strength. Incidentally, the value of the acid dissociation index pKa in the aqueous solution is:
"The Chemical Society of Japan, Basic Manual for Chemistry, Revised 4th Edition, II-3
16-321 "and the like can be referred to.

Specific examples of such an acidic substance (C) include inorganic acids, organic acids and their anhydrides, esters,
One or more selected from the group of acidic salts can be used, and examples thereof include hydrochloric acid, nitric acid, sulfuric acid, phosphoric acid, silicic acid, aluminic acid, perchloric acid, formic acid, propionic acid, caproic acid, oxalic acid, and succinic acid. Adipic acid, maleic acid, phthalic acid,
Examples thereof include benzoic acid, salicylic acid, anthranilic acid, octanoic acid, etc., or their anhydrides, esters, acid salts and the like.

Of these, phosphoric acid, silicic acid, chloroacetic acid, and phthalic acid are preferable because the acid dissociation index pKa in the aqueous solution of 2.0 to 3.0 is particularly remarkable from the viewpoint of curing acceleration effect. Examples thereof include salicylic acid, anthranilic acid and the like, or their anhydrides, esters and acidic salts.

Of these acids, acidic phosphoric acid ester and salicylic acid are particularly preferable because the effects of the present invention are particularly remarkable.

The amount of the acidic substance (C) used is arbitrarily adjusted depending on the desired curing time, but normally, the acid equivalent of the acidic substance (C) is 0 relative to the active hydrogen equivalent of the compound (B). It is in the range of 0.005 to 0.1. If it is 0.005 or less, the curing rate will be very slow, and if it is 0.1 or more, the cured material will have a large deterioration in elongation in the heat treatment described in JIS-A6021.

The composition of the present invention contains various additives such as a solvent, a small amount of process oil, a plasticizer, a thixotropic material, an extender pigment, an ultraviolet-preventing material for maintaining and improving weather resistance and a stabilizer, if necessary. Can be added, and the mixture can be uniformly mixed, and can be produced by a mixing and kneading device sufficient to ensure storage stability.

Usual solvents for urethane such as toluene, xylene, terpene and ethyl acetate can be used as the solvent. As the process oil, an ordinary high boiling point oil obtained by refining oil can be used.

As the plasticizer, general plasticizers such as dioctyl phthalate, diundecyl phthalate, dibutyl phthalate, dinonyl phthalate and diundecyl phthalate can be used. Examples of extender pigments include carbon black, calcium carbonate, talc, clay, silica and titanium oxide.

Examples of the thixotropic agent include surface-treated calcium carbonate, polyvinyl chloride powder, finely divided silica and bentonite. In addition, the urethane resin composition of the present invention may be mixed with a petroleum-based high-boiling point aromatic fraction, a petroleum resin, or the like.

The moisture-curable polyurethane composition of the present invention is mainly used as a coating material. The coating material of the present invention is, for example, a wall material, a waterproof material, a floor material, a paint or the like, which is a material for civil engineering and construction. Besides, it can be applied to various uses such as a sealing material for vehicles or an adhesive. In particular, by adding a filler to the moisture-curable polyurethane composition of the present invention, a coating material having extremely excellent waterproof reliability can be obtained.

[0040]

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.

(Preparation Example 1 of Urethane Prepolymer) 600 g of polyethylene propylene ether diol having an average molecular weight of 3000 (ethylene oxide content of about 10%),
Polyethylene propylene ether triol having an average molecular weight of 5000 (ethylene oxide content of about 10%) 40
2,4-tolylene diisocyanate 147.6 in 0 g
g, that is, NCO / OH equivalent ratio 2.65, reaction was performed in a flask under nitrogen flow at 60 ° C. for 48 hours with stirring to obtain a urethane prepolymer (P-1) having an NCO% of 3.87%. It was

(Preparation Example 2 of Urethane Prepolymer) Polypropylene ether diol 60 having an average molecular weight of 3000
0 g, 400 g of polypropylene ether triol having an average molecular weight of 5000, 147.6 g of 2,4-tolylene diisocyanate, that is, an equivalent ratio of NCO / OH of 2.65.
The reaction was carried out in a flask under nitrogen flow at 60 ° C. for 48 hours while stirring to obtain a urethane prepolymer (P-2) having an NCO% of 3.87%.

(Preparation Example 3 of Urethane Prepolymer) Polypropylene ether diol 46 having an average molecular weight of 3000
2 g, polyethylene propylene ether diol with an average molecular weight of 3000 (ethylene oxide content approx. 10%)
138 g, 308 g of polypropylene ether triol having an average molecular weight of 5000, 92 g of polyethylene propylene ether triol having an average molecular weight of 5000 (ethylene oxide content of about 10%), 147.6 g of 2,4-tolylene diisocyanate, that is, an NCO / OH equivalent ratio of 2. The reaction was carried out at 65 under nitrogen flow at 60 ° C. for 48 hours while stirring in a flask to obtain a urethane prepolymer (P-3) having an NCO% of 3.87%.

(Preparation example 1 of urethane oxazolidine compound) 729 g of urethane prepolymer (P-1) and 97.2 g of 2-isopropyl 3 (2 hydroxyethyl) 1,3 oxazolidine, that is, NCO / OH equivalent ratio of 1.1.
Under a nitrogen stream at 60 ° C. for 48 hours while stirring in a flask to obtain a urethane oxazolidine compound (O
XZ-1) was obtained. As a result of measuring GPC of this composition,
It was confirmed that the content of the remaining 2-isopropyl 3 (2 hydroxyethyl) 1,3 oxazolidine was 1% or less.

(Preparation Example 2 of Urethane Oxazolidine Compound) 444.7 g of urethane prepolymer (P-1) and 284.3 g of urethane prepolymer (P-2) and 2-isopropyl 3 (2 hydroxyethyl) 1,3 oxazolidine 97. 2g, ie NCO / OH equivalent ratio 1.1
Under a nitrogen stream at 60 ° C. for 48 hours while stirring in a flask to obtain a urethane oxazolidine compound (O
XZ-2) was obtained. As a result of measuring GPC of this composition,
It was confirmed that the content of the remaining 2-isopropyl 3 (2 hydroxyethyl) 1,3 oxazolidine was 1% or less.

(Preparation example 3 of urethane oxazolidine compound) 304 g of urethane prepolymer (P-1) and 425 g of urethane prepolymer (P-2) and 2-isopropyl 3 (2 hydroxyethyl) 1,3 oxazolidine 9
7.2 g, that is, an NCO / OH equivalent ratio of 1.1, the reaction was carried out while stirring in a flask at 60 ° C. for 48 hours under a nitrogen stream to give a urethane oxazolidine compound (OXZ-
3) was obtained. As a result of measuring GPC of this composition, residual 2-isopropyl 3 (2 hydroxyethyl) 1,
It was confirmed that the content of 3 oxazolidine was 1% or less.

(Preparation example 4 of urethane oxazolidine compound) 729 g of urethane prepolymer (P-2) and 97.2 g of 2-isopropyl 3 (2 hydroxyethyl) 1,3 oxazolidine, that is, NCO / OH equivalent ratio of 1.1.
Under a nitrogen stream at 60 ° C. for 48 hours while stirring in a flask to obtain a urethane oxazolidine compound (O
XZ-4) was obtained. As a result of measuring GPC of this composition,
It was confirmed that the content of the remaining 2-isopropyl 3 (2 hydroxyethyl) 1,3 oxazolidine was 1% or less.

[Compound Compounding] Next, it was dried in a closed planetary mixer at 150 ° C. for 2 hours, and calcium carbonate (NS-200 manufactured by Nitto Koka Co., Ltd.) adjusted to have a water content of 0.05% or less at 120 ° C. It was dried for 3 hours and the water content was reduced to 0.
Fatty acid-treated calcium carbonate adjusted to 1% or less (Hakuenka CCR manufactured by Shiraishi Calcium), urethane prepolymer, urethane oxazolidine compound, xylene, dioctyl phthalate (hereinafter abbreviated as DOP), paratoluene sulfonyl isocyanate (hereinafter abbreviated as PTSI), and various 8kPa after adding the specified amount of each acid and mixing evenly
Degassing was performed under reduced pressure to obtain a moisture-curable urethane compound. The content of ethylene oxide (EO) in the resin was kept constant at 2.0%.

[Test Method] (Tack Free Time) According to JIS-A5758.

(Foamability test) Foamability was measured by pouring a sample on a slate plate (30 * 30 cm) surrounded by four sides at a thickness of 2 mm and curing at 70 ° C. × 50%.
The presence or absence of blisters and pinholes on the surface of the coating film was observed. Those with no blisters and pinholes were marked with O, and those with blisters and pinholes were marked with x.

(Deterioration test during elongation in heat treatment)
Based on JIS-A6021.

[0052]

[Table 1] [Blending conditions and test results] Note) NCO / (H): Equivalent ratio of active hydrogen (primary amine + hydroxyl group) generated by ring opening of NCO group and oxazolidine group. 1); acidic phosphoric acid ester (isopropyl acid phosphate) 2); urethane oxazolidine prepolymer

[0053]

[Table 2] Note) NCO / (H): Equivalent ratio of NCO group and active hydrogen (primary amine + hydroxyl group) generated by ring opening of oxazolidine group.

1); Acidic phosphoric acid ester (isopropyl acid phosphate) 2); Urethane oxazolidine prepolymer 3); Urethane prepolymer *); Tetraethyl-2,2 '-(1,4-phenylene) bis (1-) Chlorohexane-
1,3-Difluoropionate) An alicyclic enamine compound described in JP-A-7-289989.

[0055]

INDUSTRIAL APPLICABILITY The present invention is a moisture-curable polyurethane resin composition which is free from blistering of a coating film due to carbon dioxide even under high temperature and high humidity, has extremely good curability, and is excellent in deterioration upon heat treatment during elongation and in heat deterioration resistance. And a coating material using the composition.

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Claims (9)

[Claims] 1. A urethane prepolymer having (A) two or more isocyanate groups at the terminal, (B) a compound having two or more oxazolidine rings in the molecule, and (C) an acid dissociation index pKa of 1.0. A moisture-curable urethane composition comprising an acidic substance of about 4.0 as an essential component. 2. The compound (B) comprises a urethane prepolymer (b1) having two or more isocyanate groups at the terminal and N.
The moisture-curable urethane composition according to claim 1, which is a urethane prepolymer having two or more oxazolidine groups at the terminal, which is obtained by reacting with 2-hydroxyalkyloxazolidine (b2). 3. The moisture-curable urethane composition according to claim 1, wherein the urethane prepolymer (b1) has an oxyethylene chain. 4. The acidic substance (C) is composed of one or more selected from the group consisting of inorganic acids, organic acids and their anhydrides, esterified products and acidic salts. The moisture-curable urethane composition described. 5. The moisture-curable urethane composition according to claim 1, wherein the acidic substance (C) is one or more selected from phosphoric acid, acidic phosphoric acid ester, salicylic acid, phosphate or phthalic anhydride. Stuff. 6. An equivalent ratio of 0.1 to an active hydrogen H (primary amine and hydroxyl group) produced by the acid of the acidic substance (C) hydrolyzing the oxazolidine ring of the compound (B).
A range of 005 to 0.1 is set.
The moisture-curable urethane composition described. 7. The ratio of the isocyanate group of the compound (A) to the active hydrogen H (primary amine and hydroxyl group) generated by hydrolyzing the oxazolidine ring of the compound (B) is equivalent to -NCO /. -H = 0.4-4.0, The moisture curable urethane composition of Claim 1 or 2 characterized by the above-mentioned. 8. The moisture-curable urethane composition according to claim 1, wherein the oxyethylene chain content is less than 6% by weight based on the total amount of the components (A) and (B). Stuff. 9. A coating material comprising the moisture-curable urethane composition according to any one of claims 1 to 7.