JP2000281757A - Polyol resin composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a polyol resin composition having a high curing rate and giving a cured product excellent in properties and chemical resistance, and chiefly used for finishing hard floorings by mixing two epoxy ring opening polyols each obtained by reacting an epoxy compound with an active hydrogen compound. SOLUTION: This composition is obtained by mixing an epoxy ring opening polyol (A) obtained by reacting an epoxy compound of formula I with an active hydrogen compound with an epoxy ring opening polyol (B) obtained by reacting an epoxy compound of formula II with an active hydrogen compound. In the formulae, R1 to R5 are each a 1-10C alkyl; and (p) is 0-10. The active hydrogen compound is exemplified by an amine compound, a carboxy compound, a carboxylic acid having an alcoholic hydroxyl group, a polycarboxylic acid, or a polyol compound. The mixing ratio component A/component B is desirably 1/9 to 9/1 by weight. The composition is compounded with a curing agent to obtain a mixture used for coating materials, adhesives, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a polyol resin composition, and more particularly, to a cured product which can be rapidly cured, has high hardness, and has excellent properties such as chemical resistance. The present invention relates to a polyol resin composition that can be suitably used for a resin composition.

[0002]

BACKGROUND OF THE INVENTION Epoxy resins and urethane resins are generally used as hard floor coverings. Epoxy resins are not preferred because they provide a high hardness and a beautiful painted surface, but lack flexibility and generally use amines, which may damage the skin. Urethane resins are rich in flexibility and excellent in curability at low temperatures, but have drawbacks such as insufficient hardness and easy foaming.

In order to solve these problems, for example, JP-A-57-92015 discloses an NCO component comprising polymethylene phenyl polyisocyanate and an oxyalkylene ether of bisphenols and a hydroxyl equivalent of 200 to 2,000 such as castor oil. Polyurethane-based hard floor finishing compositions containing an active ingredient composed of a high molecular weight polyol as an essential component have been proposed, but the curing rate is low, sufficient hardness cannot be obtained, and the chemical resistance is poor, We have not yet obtained anything satisfactory. Also, Japanese Patent Application Laid-Open No. H10-7
No. 7402 proposes a polyol resin composition in which a polyol having an ester structure and a polyol having no ester structure are used in combination. However, the chemical resistance was improved to some extent, but the hardness was insufficient.

Accordingly, it is an object of the present invention to provide a hard floor finishing composition which cures quickly and has excellent physical properties and chemical resistance of the cured product.

[0005]

Means for Solving the Problems As a result of intensive studies, the present inventors have found that an epoxy ring-opening polyol and a bisphenol skeleton obtained by reacting an active hydrogen compound with a specific epoxy compound having a tertiary alkyl group are obtained. It has been found that a polyol resin composition containing an epoxy ring-opening polyol obtained by reacting an active hydrogen compound with a specific epoxy compound having the same can achieve the above object.

The present invention has been made based on the above-mentioned findings. (A) An active hydrogen compound is added to an epoxy compound represented by the following general formula (1) of the following [Chemical Formula 3] (the same as the above [Chemical Formula 1]). An epoxy ring-opened polyol obtained by the reaction and (B) an epoxy compound obtained by reacting an active hydrogen compound with an epoxy compound represented by the following general formula (2) of the following [Formula 4] (same as the above [Formula 2]) An object of the present invention is to provide a polyol resin composition containing a ring-opening polyol.

[0007]

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[0008]

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[0009]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the polyol resin composition of the present invention will be described in detail. In the epoxy compound represented by the general formula (1) as the component (A) and the epoxy compound represented by the general formula (2) as the component (B) used in the present invention, R ₁ , R ₂ , Examples of the alkyl group having 1 to 10 carbon atoms represented by R ₃ , R ₄ and R ₅ include, for example, a straight chain such as methyl, ethyl, propyl, butyl, amyl, hexyl, heptyl, octyl, nonyl, and decyl. And a branched alkyl group.

The components (A) and (B) used in the present invention
The epoxy compound, which is a component, reacts with an active hydrogen compound having an active hydrogen to form an epoxy ring-opened polyol, and examples of the active hydrogen compound include an amine compound, a compound having a carboxyl group, and a carboxylic acid having an alcoholic hydroxyl group. , Polycarboxylic acids, polyol compounds and the like.

Examples of the amine compound include dialkylamine compounds such as dibutylamine and dioctylamine; alkanolamine compounds such as methylethanolamine, butylethanolamine, diethanolamine, diisopropanolamine and dimethylaminopropylethanolamine; morpholine, piperidine, And heterocyclic amine compounds such as -methylpiperazine. Particularly preferred is the use of a dialkanolamine compound, since a polyol resin composition having excellent properties can be obtained.

The compounds having a carboxyl group include acetic acid, propionic acid, 2,2-dimethylolpropionic acid, 12-hydroxystearic acid, lactic acid, butyric acid, octylic acid, ricinoleic acid, lauric acid, benzoic acid, and toluyl. Acids, cinnamic acid, phenylacetic acid, aliphatic and aromatic or alicyclic monocarboxylic acids such as cyclohexanecarboxylic acid, and in particular, 2,2-dimethylolpropionic acid, 12-hydroxystearic acid, ricinoleic acid,
It is preferable to use a carboxylic acid having an alcoholic hydroxyl group such as lactic acid and a fatty acid mixture containing an alcoholic hydroxyl group such as castor oil fatty acid since a polyol resin composition having excellent properties can be obtained. Further, as the polycarboxylic acid, maleic acid, fumaric acid, itaconic acid, succinic acid, glutaric acid, adipic acid, dimer acid, phthalic acid,
Examples include isophthalic acid, terephthalic acid, hexahydroacid, and hydroxypolycarboxylic acid. Further, as the polyol, for example, ethylene glycol, diethylene glycol, 1,2-propylene glycol,
1,3-propylene glycol, 2-methyl-1,3-
Propylene glycol, 2,2-dimethyl-1,3-propylene glycol, 1,2-butanediol, 1,3
-Butanediol, 1,4-butanediol, 1,5-
Pentanediol, 2,2,4-trimethyl-1,5-
Pentanediol, 1,6-hexanediol, 2-ethyl-1,6-hexanediol, 1,2-octanediol, 1,8-octanediol, 2-methyl-1,
8-octanediol, 1,9-nonanediol, 1,
Low molecular polyols such as 10-decanediol, 1,12-octadecanediol, glycerin, trimethylolpropane, and pentaerythritol are exemplified.

In the present invention, the reaction ratio between the epoxy compound as the component (A) and the epoxy compound as the component (B) and the active hydrogen compound is determined based on the active ratio to the epoxy group of each of the component (A) and the component (B). The number of hydrogen is preferably 0.7-1.
One, more preferably 0.9 to 1.0 is used at a ratio.

If the amount of the active hydrogen compound used is less than the above range, a large amount of unreacted epoxy groups will remain in the polyol resin composition. The unreacted active hydrogen compound remains, which is not only wasteful but also may adversely affect the properties of the cured film when formed.

In order to add the active hydrogen compound to each of the epoxy compounds (A) and (B), a conventional method can be employed. For example, tertiary amine compounds, phosphonium salts and the like can be used. A method in which both are heated to 60 to 200 ° C. and reacted for 3 to 10 hours in the presence of a known catalyst can be used.

In the polyol resin composition of the present invention, the content of the epoxy ring-opening polyol obtained by reacting an active hydrogen compound with the epoxy compound as the component (A) is preferably 10 to 90% by weight, more preferably Fifteen
~ 80% by weight. In the polyol resin composition of the present invention, the content of the epoxy ring-opening polyol obtained by reacting the epoxy compound as the component (B) with the active hydrogen compound is preferably 10 to 90% by weight, more preferably 15 to 90% by weight. ~ 80% by weight.

An epoxy ring-opening polyol obtained by reacting an active hydrogen compound with the epoxy compound as the component (A) and an epoxy ring-opening polyol obtained by reacting an active hydrogen compound with the epoxy compound as the component (B). The weight ratio with the polyol (the former / the latter) is preferably from 1/9 to
9/1, and more preferably 3/7 to 7/3.

The polyol resin composition of the present invention is generally used with a curable composition, such as a paint or an adhesive, in which a curing agent is blended.

The curing agent can be used without any particular limitation as long as it is generally used as a curing agent for a polyol resin composition. In particular, an average of more than one isocyanate in a molecule is used. It is preferable to use a polyisocyanate compound having a group.

As the above polyisocyanate compound,
Aliphatic, alicyclic and aromatic polyisocyanates include, specifically, 2,4-tolylene diisocyanate,
2,6-tolylene diisocyanate, 4,4-diphenylmethane diisocyanate, phenylene diisocyanate, xylylene diisocyanate, tetramethyl xylylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, lysine diisocyanate ester, 1,4-cyclohexylene diisocyanate, 4, 4-dicyclohexylmethane diisocyanate, 3,3'-dimethoxy-4,4'-biphenylene diisocyanate, 1,5-naphthalenediisocyanate, isophorone diisocyanate and the like can be mentioned, and these can be used alone or in combination of several kinds. . It is also possible to use a high molecular weight polyisocyanate (prepolymer) having an isocyanate group at a terminal such as an adduct of a polyhydric alcohol such as ethylene glycol, polyethylene glycol, polypropylene glycol, and trimethylolpropane with these polyisocyanate compounds. I can do it.

The amount of the polyisocyanate compound used is determined by the amount of hydroxyl group 1 in the polyol resin composition of the present invention.
The number of isocyanate groups in the polyisocyanate compound is preferably 0.4 to 1.2, more preferably 0.7 to 1.0 per unit. If the use amount of the polyisocyanate compound is less than the above range, a large amount of unreacted hydroxyl groups will remain, and not only will the mechanical properties of the cured film become insufficient, but also adversely affect water resistance. In some cases. Further, if the polyisocyanate compound is used outside the above range, it is not only wasteful but also may be foamed.

When the polyol resin composition of the present invention is used as a paint, a solvent may be added to dissolve the polyol resin composition and the curing agent. Examples of these solvents include acetone. , Methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc .; ketones such as ethyl acetate, butyl acetate, ethyl acetoacetate, 2-ethoxyethyl acetate; diethylene glycol dimethyl ether, propylene glycol monoethyl ether, propylene glycol monoethyl ether acetate, etc. Ether type; xylene,
Aromatic hydrocarbons such as toluene; aliphatic hydrocarbons; alicyclic hydrocarbons; N, N-dimethylformamide;
N-dimethylacetamide, terpenes and the like can be used,
These solvents can be optionally used as a mixed solvent of two or more kinds.

The polyol resin composition of the present invention may further contain, if necessary, other polyol compounds, phenolic antioxidants, ultraviolet absorbers, stabilizers such as light stabilizers, curing catalysts, monoglycidyl ethers. , Dioctyl phthalate, dibutyl phthalate, benzyl alcohol, terpene phenolic resin, reactive or non-reactive diluent (plasticizer) such as coal tar, glass fiber, carbon fiber, cellulose, silica sand, cement, kaolin, clay, Aluminum hydroxide, bentonite, talc, silica, finely divided silica, titanium dioxide, carbon black,
Fillers such as graphite, iron oxide and bituminous substances, or conventional additives such as pigments, zeolites, anti-foaming agents such as chromium oxide, antifoaming agents, etc., and further, xylene resins, petroleum resins, etc. Can be used in combination.

The other polyol compounds mentioned above include:
For example, alkylene oxaside (ethylene oxide, propylene oxide, butylene oxide, etc.) adduct of low molecular polyol or amine such as ethylenediamine, hexamethylenediamine, polyethylene glycol, polypropylene glycol, polyethylene / propylene glycol, polytetramethylene glycol, (hydrogenated) Polyether polyols of adducts of alkylene oxides of bisphenols; polycarbonate polyols; polyepoxy polyols; halogen-containing polyols; phenolic polyols; polyolefinic polyols; acrylic polyols;

Examples of the phenolic antioxidants include stearyl-β- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate and stearyl-β-
(3-tert-butyl-4hydroxy-5-methylphenyl) propionate, 1,6-hexamethylenebis [β
-(3,5-di-tert-butyl-4-hydroxyphenyl)
Propionate], triethylene glycol bis [β-
(3-tert-butyl-4hydroxy-5-methylphenyl)
Propionate], 3,9-bis [1,1-dimethyl-
2- (β-3-tert-butyl-4-hydroxy-5-methylphenyl) propionyloxyethyl] -2,4
8,10-tetraoxaspiro [5.5] undecane,
1,3,5-tris [β- (3,5-di-tert-butyl-4
(Hydroxyphenyl) propionyloxyethyl] isocinurate, tetrakis [methylene-β- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate] methane, 2,6-di-tert-butyl-p-cresol,
2,2′-methylenebis (4-methyl-6-tert-butylphenol), 2,2′-methylenebis (4-ethyl-
6-tert-butylphenol), 2,2′-ethylidenebis (4,6-ditertbutylphenol), 2,2′-ethylidenebis (4-secbutyl-6-tertbutylphenol), bis [3 3-bis (4-hydroxy-3-tert-butylphenyl) butylic acid] glycol ester, 4,4'-butylidenebis (6-tert-butyl-m
-Cresol), 4,4'-thiobis (6-tert-butyl-m-cresol), 1,1,3-tris (2-methyl-4-hydroxy-5-tert-butylphenyl) butane,
1,3,5-tris (3,5-ditert-butyl-4-hydroxybenzyl) -2,4,6-trimethylbenzene,
1,3,5-tris (2,6-dimethyl-3-hydroxy-4-tert-butylbenzyl) isocyanurate,
3,5-tris (3,5-ditert-butyl-4-hydroxybenzyl) isocyanurate and the like.

The amount of these phenolic antioxidants added is preferably from 0.001 to 5 parts by weight, more preferably from 0.01 to 5 parts by weight, per 100 parts by weight of the polyol resin composition of the present invention.
5 to 3 parts by weight.

Examples of the ultraviolet absorber include, for example, 2,
4-dihydroxybenzophenone, 2-hydroxy-4
-Methoxybenzophenone, 2-hydroxy-4-octoxybenzophenone, 5,5'-methylenebis (2-
2-hydroxybenzophenones such as (hydroxy-4-methoxybenzophenone); (2 ′ 2-hydroxy-
5′-methylphenyl) benzotriazole, (2 ′ 2
-Hydroxy-5'-tert-octylphenyl) benzotriazole, 2- (2'-hydroxy-3 ', 5-ditert-butylphenyl) benzotriazole, 2- (2'-
Hydroxy-3'5'-di-tert-butylphenyl) -5
Chlorobenzotriazole, 2- (2'-hydroxy-
3'-tert-butyl-5'-methylphenyl) -5-chlorobenzotriazole, 2- (2'-hydroxy-3 '
, 5'-Dicumylphenyl) benzotriazole,
2- (2'-hydroxyphenyl) benzotriazoles such as 2,2'-methylenebis (4-tert-octyl-6-benzotriazolyl) phenol; phenyl salicylate, resorcinol monobenzoate, 2,4-di-tert-butyl Benzoates such as phenyl-3 ', 5'-di-tert-butyl-4'-hydroxybenzoate, hexadecyl-3,5-di-tert-butyl-4-hydroxybenzoate; 2,4-diphenyl-6- (2- Hydroxy-4
-Methoxyphenyl) 1,3,5-triazine, 2,4
-Bis- (2,4-dimethylphenyl) -6- (2-hydroxy-4-octoxyphenyl) -1,3,5-triazine, 2,4-diphenyl-6- (2-hydroxy-4-hexyloxy ) Triazines such as 1,3,5-triazine; 2-ethyl-2'-ethoxyoxanilide;
Substituted oxanilides such as 2-ethoxy-4'-dodecyl oxanilide; ethyl-α-cyano-β, β-diphenylacrylate, methyl-2-cyano-3-methyl-3
And cyanoacrylates such as-(p-methoxyphenyl) acrylate.

[0028] The amount of these ultraviolet absorbers added is preferably 0.1 to 100 parts by weight of the polyol resin composition of the present invention.
05 to 10 parts by weight, more preferably 0.01 to 5 parts by weight.

Examples of the hindered amine light stabilizer include 2,2,6,6-tetramethyl-4-piperidyl stearate, 1,2,2,6,6-pentamethyl-4-piperidyl stearate, 2,2,6,6-
Tetramethyl-4-piperidyl benzoate, bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate, bis (1,2,2,6,6-pentamethyl-
4-piperidyl) sebacate, tetrakis (2,2,
6,6-tetramethyl-4-piperidyl) butanetetracarboxylate, tetrakis (1,2,2,6,6,
-Pentamethyl-4-piperidyl) -1,2,3,4-
Butanetetracarboxylate, bis (2,2,6,6
-Tetramethyl-4-piperidyl) di (tridecyl)
-1,2,3,4-butanetetracarboxylate, bis (1,2,2,6,6-pentamethyl-4-piperidyl) di (tridecyl) -1,2,3,4-butanetetracarboxylate , Bis (1,2,2,6,6-pentamethyl-4-piperidyl) -2-butyl-2- (3,
5-di-tert-butyl-4-hydroxybenzyl) malonate, 1- (2-hydroxyethyl) -2,2,6,6-
Tetramethyl-4 piperidinol / diethyl succinate polycondensate, 1,6-bis (2,2,6,6-tetramethyl-4-piperidylamino) hexane / dibromoethane polycondensate, 1,6-bis (2 , 2,6,6-tetramethyl-4-piperidylamino) hexane / 2,4-dichloro-6-tert-octylamino-s-triazine polycondensate,
1,6-bis (2,2,6,6-tetramethyl-4-piperidylamino) hexane / 2,4-dichloro-6-morpholino-s-triazine polycondensate and the like.

As a method for preparing a paint using the polyol resin composition of the present invention, a desired additive such as a filler is added to the polyol resin composition, glass beads are added thereto, and the mixture is shaken for a predetermined time according to a conventional method. A method of kneading with a mill or the like can be used. The obtained coating material can be mixed with a curing agent, applied with a desired thickness using a trowel, a bar coater, or the like, and dried and cured to form a coating film.

The polyol resin composition of the present invention is preferably used particularly for hard floor finishes.

[0032]

EXAMPLES Examples of the present invention will be shown below, but the present invention is not limited to these examples. In the examples, parts are parts by weight unless otherwise specified, and the epoxy equivalent is defined as the molecular weight of the epoxy resin per epoxy group, and the phenolic OH equivalent is the weight per phenolic hydroxyl group. The alcoholic OH equivalent is defined by the molecular weight of the polyol resin composition per alcoholic hydroxyl group, and the hydroxyl value (OHV) is defined by the molecular weight of the alcoholic hydroxyl group in 1 g of the polyol resin composition. It is defined as the number of mg of potassium hydroxide required to add up.

Synthesis Example 1 In a reaction vessel equipped with a thermometer, a stirrer, a cooling pipe, and a nitrogen inlet, 2,2-dimethyloctanoic acid glycidyl ester (hereinafter sometimes referred to as DMOGE) in an amount shown in Table 1. ), Adeka Resin EP-4100 (manufactured by Asahi Denka Kogyo Co., Ltd .; bisphenol A type epoxy resin, epoxy equivalent 190), castor oil fatty acid, heated to 160 ° C., reacted for 3 hours, and further reduced to 30 torr for 1 hour The reaction was carried out to reduce the acid value to 1 or less to obtain a polyol resin composition having a hydroxyl equivalent of 259. The resulting polyol resin composition was reacted with a curing agent to prepare Example 1-1.

Synthesis Example 2 In the same reaction vessel as in Synthesis Example 1, 2, 2
-Dimethyloctanoic acid glycidyl ester, Adeka Resin EP-4901 (manufactured by Asahi Denka Kogyo Co., Ltd .; bisphenol F type epoxy resin, epoxy equivalent: 173), and castor oil fatty acid were charged, and the temperature was raised to 160 ° C. and reacted for 3 hours, and further to 30 torr The reaction was carried out under reduced pressure for 1 hour to obtain an acid value of 1 or less to obtain a polyol resin composition having a hydroxyl equivalent of 255. A curing agent was allowed to react with the obtained polyol resin composition to obtain Example 1-2.

Synthesis Example 3 Similarly, 2,2-dimethyloctanoic acid glycidyl ester, ADEKARESIN EP-4080 (manufactured by Asahi Denka Kogyo KK; bisphenol A type, epoxy equivalent 248) and castor oil fatty acid were used in the amounts shown in Table 1. The mixture was heated to 160 ° C. and reacted for 3 hours, and further reduced to 30 torr for 1 hour to obtain a polyol resin composition having an acid value of 1 or less and a hydroxyl equivalent of 274. A curing agent was allowed to react with the obtained polyol resin composition to obtain Example 1-3.

Synthesis Examples 4 to 6 In the same manner as described above, a curing agent was reacted with the polyol compound obtained by blending in Table 1 to prepare Examples 1-4 and 1-
5, and Example 1-6. However, BPX-21, EM
-53 and EDP-300 represent the following compounds, respectively.

[0037]

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EM-53: ethylene oxide / propylene oxide adduct of ethylene diamine (molecular weight: 50
0). EDP-300: ethylenediaminepropylene oxide adduct (molecular weight 300).

EXAMPLES The paints were mixed and adjusted according to the formulations shown in Tables 1 to 3 below.
The gel time and the coating hardness (Shore D) after 24 hours at 20 ° C. were measured according to ASTM standards. (Mechanical strength) Tensile strength, bending strength, compression strength, and drop test were performed according to JIS K6301.

(Chemical resistance) A coated plate was prepared from the above paint, and the coated plate was immersed in tap water, a 5% sodium hydroxide solution and a 5% hydrochloric acid solution, respectively, and weighed one week later (% ) And a decrease in hardness (difference before and after immersion) were confirmed.

The above test results are shown in Tables 1 to 3, respectively.

[0042]

[Table 1]

[0043]

[Table 2]

[0044]

[Table 3]

From Tables 1 and 2, the polyol resin composition of the present invention can provide a cured product having a fast curing time, a high coating film hardness, and excellent mechanical strength and chemical resistance. The cured product had the same properties as the coating film hardness and mechanical strength of the examples, but it was confirmed that there was a problem in chemical resistance. Also, from Table 3, it can be seen that the polyol resin composition of the present invention can give an excellent cured product without reducing the performance in curing speed, coating film hardness, and chemical resistance even when calcium carbonate is added. Was confirmed.

[0046]

Industrial Applicability The polyol resin composition of the present invention comprises an epoxy ring-opening polyol obtained by reacting an active hydrogen compound with a specific epoxy compound having a tertiary alkyl group and an active hydrogen compound with a specific epoxy compound having a bisphenol skeleton. It contains an epoxy ring-opening polyol obtained by reacting a compound, and can give a cured product excellent in coating film hardness, mechanical strength and chemical resistance.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI theme coat ゛ (Reference) C08G 59/62 C08G 59/62 C09D 7/12 C09D 7/12 Z 163/00 163/00 175/04 175 / 04 F-term (reference) 4J034 BA08 CA03 CB02 CC09 DA01 DB03 DB07 DC02 DC43 DK02 DK05 HA01 HA02 HA07 HA11 HC12 HC13 HC17 HC22 HC46 HC52 HC61 HC64 HC67 HC70 HC71 HC73 RA07 4J036 AA02 AD08 CA03 CA04 CA18 CA22 CA04 CA10 CB04 CB04 CB04 JA01 4J038 DB061 DB091 DG101 DG161 DG271 DG281 GA03 KA03 NA04 NA11 NA23 PB05

Claims (4)

[Claims] 1. An epoxy ring-opening polyol obtained by reacting an active hydrogen compound with an epoxy compound (A) represented by the following general formula (1) represented by the following general formula (1) and a compound represented by the following general formula (2): A) a polyol resin composition containing an epoxy ring-opening polyol obtained by reacting an active hydrogen compound with the epoxy compound (B) represented by Embedded image Embedded image 2. The polyol resin composition according to claim 1, wherein the active hydrogen compound is a carboxylic acid having a hydroxyl group. 3. The polyol resin composition according to claim 1, wherein a polyisocyanate compound is used as a curing agent. 4. The polyol resin composition according to claim 3, which is used for a hard floor finishing material.