JP2000290582A - Epoxy resin-based material for floor coating flooring - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a material for floor coating excellent in shelf stability and moisture-curable at room temperature by compounding a heterocycle- containing compound containing at least two heterocyclic groups and a polyepoxy compound. SOLUTION: A heterocyclic group-containing compound (A) bearing at least two, preferably 2-20, heterocyclic groups of the formula on its side chain and/or on its ends and having a number average mol.wt. of 400-20,000, preferably 600-2,000, a viscosity (25 deg.C) of 200-200,000, preferably 600-2,000 cP and a mol.wt., per one heterocyclic group, of 150-2,000, preferably 200-500 and a polyepoxy compound (B) are compounded so that the ratio of the heterocyclic group equivalent in the formula of the component A to the epoxy equivalent of the component B is 0.4-2.5. In the formula, R is a 1-10C linear or branched alkylene optionally containing -O- and/or -S-; R1 and R2 are each H, a 1-6C linear or branched chain alkyl or alkenyl, a 6-8C aryl or the like; and R3 is 1-10C alkylene.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a coated flooring,
More specifically, the present invention relates to a novel epoxy resin-based floor covering material which has excellent storage stability and can be cured at room temperature by moisture.

[0002]

2. Description of the Related Art Horizontal surfaces through which people, trolleys, vehicles, etc. pass,
A coated floor material is applied to a floor surface such as an inclined surface or a rising surface associated with the floor surface for the purpose of imparting performance such as dustproof, touchproof or rustproof. Usually, a coated floor material is applied as a primer, a base coat or a top coat on each floor surface. A room temperature curing type epoxy resin-based coated flooring material is known as the coated flooring material, and a one-pack type epoxy resin-based coated flooring material using a ketimine compound as a curing agent component is known.

[Problems to be solved by the invention]

[0003] However, coated flooring materials using a ketimine compound have insufficient storage stability and curing performance, and often use a large amount of volatile organic solvents. There is a demand for a coated flooring material that does not use any solvent.

[0004]

Means for Solving the Problems The present inventors have made intensive studies to solve the above-mentioned problems, and as a result, have found that a novel epoxy resin-based floor covering material using a heterocyclic-containing compound as a latent curing agent is used. As a result, they have found that the above problem can be solved, and have completed the present invention. That is, the present invention provides an epoxy resin-based coated flooring material comprising a heterocyclic group-containing compound (A) having two or more heterocyclic groups (Z) represented by the following general formula (1) and a polyepoxy compound. It is.

[0005]

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(Wherein R is a linear or branched alkylene group having 2 to 10 carbon atoms which may contain -O- and / or -S-, R ¹ and R ² are the same and And may represent a hydrogen atom, a linear or branched alkyl or alkenyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 8 carbon atoms, or R ¹ and together with the carbon atom to which R ² is attached, .R ³ representing a cycloalkyl ring having 5 to 7 carbon atoms, 1 to carbon atoms
Represents 10 alkylene groups. )

[0007]

BEST MODE FOR CARRYING OUT THE INVENTION The heterocyclic-containing compound of the present invention is not particularly limited as long as it has two or more Zs represented by the above general formula (1). , Polyvinyl, polyester, polyamide, polycarbonate, and novolak, and at least one selected from the group consisting of hydrocarbons optionally having a hydroxyl group.
Heterocycle-containing compounds having a different main chain and having at least two Z's at the terminal or side chains are included.

In the general formula (1), R¹And R^Twoage
Specifically, for example, for example, a hydrogen atom;
, N- and i-propyl, n-, i-, s- and t-
Butyl, n-, i- and t-pentyl, neopentyl,
n- and i-hexyl groups; and vinyl, allyl, pro
Phenyl, butenyl and hexenyl groups; phenyl, tri
, Xylyl, benzyl and phenylethyl groups.
Can be R¹, R^TwoAnd R ¹And R^TwoTo which the carbon is attached
As a cycloalkyl ring in which atoms are joined together,
For example, cyclopentyl, cyclohexyl and cyclohepti
And the like. Of these, in terms of cure speed
R¹And R^TwoAt least one of them is a hydrogen atom,
Or a linear or branched alkyl having 1 to 3 carbon atoms
Group (especially a methyl or ethyl group)
No. R^ThreeSpecifically, for example, methylene, ethyl
Len, 1,2- and 1,3-propylene, tetramethyl
1,2-ethylethylene, pentamethylene, hexa
Examples include methylene, heptamethylene, octamethylene, etc.
Is done. Of these, ethylene,
1,2- and 1,3-propylene, tetramethylene and
Pentamethylene groups are preferred. R is -O- and / or-
C2-C10 linear or branched which may have S-
Alkylene group, for example, ethylene, 1-methyl
Methylene, 1,1-dimethylmethylene, 1-ethylmethyl
Len, 1,2- and 1,3-propylene, tetramethyl
1,1-dimethylethylene, 1-methyltrimethylene
Hexamethylene, 1-methylhexamethylene, octane
A straight or branched chain having 2 to 10 carbon atoms such as a tamethylene group.
Alkylene group, -CH_TwoCH_TwoOCH_TwoCH_Two-, -CH_TwoC
H_TwoCH_TwoOCH_TwoCH_Two-, -C (CH_Three) HCH_TwoOCH
_TwoCH (CH_Three)-, -CH_TwoCH_TwoSCH_TwoCH_Two-, -C
H_TwoCH_TwoCH_TwoSCH_TwoCH_Two-O- having a structure such as-,
Linear or branched alkyl having 2 to 10 carbon atoms having -S-
And a kylene group. Among them, carbon number 2-10
Are preferred, particularly 1-methyl
Tylene groups are preferred.

In the coated flooring material of the present invention, the heterocyclic-containing compound has 2 to 50 or more heterocyclic groups (Z) represented by the general formula (1) on the side chain and / or the terminal. Preferably, the number is 2 to 20, particularly preferably 2
~ 7. If the number of the heterocyclic groups is less than 2, the curing of the epoxy resin is insufficient, so that the range is limited to the above range. As the heterocyclic-containing compound having a main chain structure composed of a hydrocarbon which may have a hydroxyl group, polyether, polyvinyl, polyester, polyamide, polycarbonate and novolak, the following general formula (2):
(3) having a structure shown in (4), (5) and (6), (7) and (8), (9) and (10),
Those having 2 to 50 or more -XZ groups are exemplified. Those having 2 to 7 -XZ groups are particularly preferable from the viewpoint of hardness and flexibility of the cured product. It does not prevent these main chain structures from being mixed with each other in a random or block manner. Of these main chain structures, (3) to (1)
The main chain structure of (0) is the same as that described in detail in JP-A-09-188744 or US Pat. No. 5,837,785.

[0010]

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The -XZ group is a group represented by -XZ [formula
In the formula, X represents a direct bond or a divalent organic group. Z is above
Represents a heterocyclic group represented by the general formula (1). ].
Examples of the organic group represented by X include, for example, an ether group,
Oether group, carbonate group, ester group, imino
Group, amide group, urethane group, urea group and sulfide group
May have one or more groups selected from the group consisting of
A divalent hydrocarbon group having 1 to 30 or more carbon atoms
Illustrative and specific examples include, for example, -CH_Two-, -C
H_TwoCH_Two-, -CH_TwoOCH_TwoCH_Two-, -CH_TwoS
CH_TwoCH_Two -, -CHO-CO-OCH_Two-, -NH
CONH-, -NH-CO-O-, -CH_TwoNHCH_Two
CH_Two-, -CH_TwoNHCONH (CH_Two)₆NHCO
-O- and -CH_TwoS (CH_Two)_TwoC (= O) O (CH
_Two)_Two-,-(OA^o)_p[OCH_TwoCH (OH) CH_Two]
_r-[A in the formula^o, P and r are the same as in the general formula (11).
Yes] and other groups having such a structure.

Hereinafter, these will be described in detail. The heterocyclic-containing compound (A) having a structure represented by the general formula (2) has a hydrocarbon main chain structure which may have a hydroxyl group in a side chain. In the formula (2), a is 1 to 5
It is an integer of 0. From the viewpoint of the viscosity of the coated floor material and the hardness of the cured resin, it is preferably from 1 to 25, particularly preferably from 1 to 10. A ¹ is a linear or branched alkylene group having 2 to 15 carbon atoms, which may contain a hydroxyl group, or an arylene group having 6 to 50 carbon atoms, and the number of hydroxyl groups represents 0 to 8; The linear or branched alkylene group having 2 to 15 carbon atoms of A ¹ or the arylene group having 6 to 50 carbon atoms is substituted or unsubstituted with an -XZ group,
When a is 1, A ¹ must contain two -XZ groups.

In the general formulas (3) to (10), b to i are 2 to
It is an integer of 200. From the viewpoint of the viscosity of the coated flooring material and the hardness of the cured resin, b to i are preferably 2 to 100. In the general formula (3), A ² represents an alkylene group having 2 to 30 carbon atoms, which is substituted or unsubstituted with an -XZ group, an arylene group, an arylalkylene group, a haloalkylene group, or glycidyl ether. It represents the residue after ring-opening polymerization. At least two of the b A ^{2 in} the general formula (3) represent an alkylene group substituted with a —XZ group. From the point of hardness of the cured product, ² out of b A 2
Preferably, 7 represents an alkylene group substituted with a -XZ group. Specific examples of A ^{2 in} the general formula (3) include methylene, ethylene, trimethylene, 1,2
A hydrogen atom of an alkylene group exemplified by propylene, tetramethylene, pentamethylene, hexamethylene, octamethylene, or the like is substituted with an -XZ group (the substitution position is not limited) or is not substituted Groups; arylene groups such as phenylene and naphthylene groups; groups in which hydrogen atoms of arylalkylene groups such as phenylethylene and tolylethylene groups are substituted or unsubstituted by -XZ groups; chloroethylene, chloromethylethylene groups and the like Wherein the hydrogen atom of the haloalkylene group is substituted or unsubstituted by an -XZ group; monoglycidyl such as butyl glycidyl ether, phenyl glycidyl ether, allyl glycidyl ether, 2-ethylhexyl glycidyl ether, and cresyl glycidyl ether ether,
Diglycidyl ether, (poly) ethylene glycol (polymerization degree: 2 to 100) diglycidyl ether, (poly) propylene glycol (polymerization degree: 2 to 100) diglycidyl ether, butanediol diglycidyl ether such as diglycidyl ether, and triglycidyl ether Epoxy equivalents of 3 to 6 functional or higher polyglycidyl ethers such as methylolpropane triglycidyl ether, etc. 65 to 10
A residue obtained by ring-opening polymerization of 1 to 6 or more epoxy groups of glycidyl ethers of No. 00; and a hydrogen atom such as a glycidyl ester having a functional group similar to that of glycidyl ether is an -XZ group. Substituted or unsubstituted groups are included.

In the general formula (4), Q ¹ represents a hydrogen atom; an alkyl group having 1 to 30 carbon atoms, an aryl group, a haloalkyl group, a haloaryl group, an alkoxycarbonyl group, an acyloxy group, or an -XZ group. . At least two of the c Q ^{1 in} the general formula (3) represent a —XZ group. From the viewpoint of the hardness of the cured product, 2 to 7 of the c-number for Q ¹ is -
Preferably it represents an XZ group. Specific examples of Q ^{1 in} the general formula (4) include a hydrogen atom; an alkyl group such as methyl and ethyl; an aryl group such as phenyl and tolyl;
Halogen number of 1 to 61 such as chloromethyl and chloroethyl groups
Haloalkyl group; chloromethylphenyl, chloroethylphenyl, 2,4,6-trichlorophenyl, 2,
A haloaryl group such as a 4,6-tribromophenyl group; an alkoxycarbonyl group having 1 to 6 carbon atoms such as a methoxycarbonyl, ethoxycarbonyl, butoxycarbonyl group;
An acyloxy group having 1 to 6 carbon atoms such as an acetoxy group and -X
—Z group and the like.

In the general formulas (5) to (9), A ³ , A ⁴ ,
A ⁵ , A ⁶ , A ⁷ , A ⁸ and A ⁹ are the same or different and are each an alkylene group having 1 to 30 carbon atoms, which is substituted or unsubstituted by an -XZ group, or an -XZ group. Represents a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, an aralkylene group, or a haloalkylene group having 1 to 30 carbon atoms. Specific examples of the above A ^{3 to} A ⁹ include:
A group in which a hydrogen atom of an alkylene group such as methylene, ethylene, propylene, tetramethylene, ethylethylene, hexamethylene, heptamethylene, octamethylene or the like is substituted or unsubstituted by an -XZ group; a phenylene group, a tolylene group Hydrogen atom of the arylene group such as -XZ
A group substituted or unsubstituted with a group; an aralkylene group such as a benzylidene group and an ethylenephenylene group;
Examples include groups in which a hydrogen atom such as a haloalkylene group such as a chloroethylene group, a bromoethylene group, a chloromethylethylene group, or a 1,2-dichloroethylene group is substituted or unsubstituted by an -XZ group. In the general formula (10),
Ar represents an aromatic hydrocarbon group, for example, an alkyl-substituted benzene ring represented by the general formula (12), a substituted phenylene group which is a residue of a phenol novolak resin, a substituted tolylene group which is a residue of a cresol novolak resin. At least two of i in the general formula (10) represent a -XZ group.

[0016]

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(Wherein R ⁰ is a hydrogen atom or a carbon atom 1)
An alkyl group) Q ² of 30 represents a hydrogen atom, a glycidyl group, or -X-Z group.
Of these main chain structures, preferably, the general formula (2):
It has a main chain structure represented by (3), (4), (6), (9) and (10), and more preferably a general formula (2):
The main chain structure represented by (3) and (4), particularly preferably the main chain structure represented by the general formula (2). In the heterocycle-containing compound having a structure represented by any of the general formulas (2) to (10), the ratio of the group having an -XZ group to the other group, the type of the other group, the type of the X group, By changing the values of a to i, physical properties such as viscosity of the coated flooring material of the present invention, compatibility with the polyepoxy compound, hardness of the epoxy resin after curing, flexibility, weather resistance, chemical resistance and the like are controlled. be able to.

The heterocyclic group (Z) of the heterocyclic-containing compound (A) is (i) a compound having at least two secondary amino groups bonded to a hydroxyalkyl group in the molecule [general formulas (2) to ( 10)] and an aldehyde (b1) or a ketone (b
(Ii) a dehydration-condensation reaction of (b) or (b2) with an alkanolamine Michael-added to (meth) acrylic acid ester, and then the product is converted to a hydroxyl group and / or A direct esterification or transesterification reaction with a compound having a glycidyl group [this compound corresponds to a compound represented by formulas (2) to (10) or a monomer] (if the compound is a monomer, it may be further used alone or Copolymerization with a monomer having a functional group capable of reacting with a).
About these manufacturing methods, the same method as the method described in JP-A-9-188744 can be mentioned.

The compound containing a heterocyclic group (Z) having a structure of the general formula (2), which is a particularly preferred main chain of the above general formulas (2) to (10), in the side chain is described below. A
A) will be described in detail. (AA) is represented by the following general formula (11). In the general formula (11), i = 1
Is the case. General formula

[0020]

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Wherein A ¹⁰ is a residue obtained by removing a hydroxyl group from k-valent polyhydric alcohols and k-valent polyhydric phenols. A ^o is a linear or branched alkylene group having 2 to 4 carbon atoms, and p and q are 0 or 1 to 1
It is an integer of 0 and may be the same or different.
r is 0 or 1. Z ¹ represents OH or Z. Q ³ is a hydrogen atom or a glycidyl group. m is 1 or an integer of 2 to 10, k is an integer of 2 to 10, and k ≧ m. When m + r ≧ 2 and m = 1, Z ¹ is Z. p,
q, r, A _o, may be different even if the same case where Z ¹ and Q ³ have multiple. In the heterocyclic-containing compound (AA) represented by the general formula (11), A ¹⁰ is an aliphatic polyhydric alcohol having 2 to 15 carbon atoms, or divalent to 10 valent having 6 to 50 or more carbon atoms. These are residues obtained by removing the hydroxyl group from the phenols.

The aliphatic polyhydric alcohols having 2 to 15 carbon atoms include (poly) alkylene glycols having 2 to 15 carbon atoms, for example, ethylene glycol, propylene glycol, 1,3-butylene glycol, 1,4- Butanediol, 1,6-hexanediol, 3-methylpentanediol, diethylene glycol, neopentyl glycol and the like; an alicyclic diol having 6 to 15 carbon atoms, for example, 1,4-bis (hydroxymethyl) cyclohexane, 2,2 ′ -Bis (4,4'-hydroxycyclohexyl) propane and the like; an aliphatic trihydric alcohol having 3 to 15 carbon atoms, for example, a trihydric alcohol such as glycerin and trimethylolpropane; a 4 to 8 alcohol having 4 to 15 carbon atoms; For example, pentaerythritol, diglycerin, α-
Examples thereof include 4- to 8-hydric alcohols such as methylglucoside, sorbitol, xylitol, mannitol, dipentaerythritol, glucose, fructose, and sucrose. Examples of the divalent to octavalent phenols having 6 to 50 or more carbon atoms (excluding novolaks) include bisphenols such as bisphenol A, bisphenol F and bisphenol S, and monocyclic compounds such as pyrogallol, catechol and hydroquinone. And polyhydric phenols.

In the general formula (11), A ^o is a linear or branched alkylene group having 2 to 4 carbon atoms, and specific examples thereof include ethylene, propylene, isobutylene, tert.
-Butylene group, preferably propylene, isobutylene, t
An ert-butylene group, particularly preferably a propylene or isobutylene group is mentioned. p or q is 0 or an integer of 1 to 10, and p and q may be the same or different.
Q ³ is a hydrogen atom or a glycidyl group. r is 0 or 1
It is. The heterocycle-containing compound (AA) has a pKa of 7 or less.
A compound represented by the general formula (14) in which an alkanolamine (a2) represented by the formula NH ₂ —R ³ —OH is Michael-added to a methacrylic ester compound (a1) represented by the following general formula (13) having ad) and the formula R ¹ -C
(B) a compound obtained by subjecting a compound (b) represented by (＝ O) —R ² to a cyclization reaction or a Michael addition of (a2) to a methacrylate (a3) represented by the general formula (15);
After cyclization by reacting with a compound having a hydroxyl group and / or a glycidyl group represented by the general formula (16). The latter method is preferred. General formula

[0024]

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[0025] The same as in the general formula (11), R ⁴ is an organic group. n is 0 or an integer of 1 to m, and m ≧ n ≧ 0. ]

In the former production method, the compound represented by the general formula (16) is obtained by adding (i) an alkylene oxide having 2 to 4 carbon atoms to the above-mentioned polyhydric alcohols and polyphenols, (ii) It is obtained by glycidylation with epichlorohydrin, or (iii) by performing (ii) after the above (i). Among the compounds (AA) having the structure represented by the general formula (11), those having m of 2 to 10 and those having m of 1, Z ¹ and Z are useful as epoxy resin curing agents. Preferably, m is 3 to 8. When m is greater than 2, the physical properties of the cured epoxy resin are good, and when m is less than 10, the viscosity does not increase, and the workability of a one-pack resin composition is good.

In the case of (AA), from the viewpoint of curing speed,
At least one of R ¹ and R ² in the general formula (1) is
It is preferably a hydrogen atom or a linear or branched alkyl group having 1 to 3 (particularly 1 to 2) carbon atoms. When the heterocycle-containing compound has (Z) represented by the general formula (1), the compound has an ester group in the molecular structure, but R is -C
H (CH ₃ ) CH ₂ — is preferable because it has a methacrylic structure and thus has better hydrolysis resistance and the like than the acrylic structure of —CH ₂ CH ₂ —. Therefore, by setting the carbon atom bonded to Z to a secondary or higher carbon represented by the following general formula (17), the hydrolysis resistance is dramatically improved. General formula

[0028]

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[In the formula, R ⁵ and R ⁶ are any of a hydrogen atom, a methyl group, an ethyl group, and —CH ₂ —Z, which may be the same or different. However, when the carbon numbers of R ⁵ and R ⁶ are C ⁵ and C ⁶ respectively,
1 ≦ C ⁵ + C ⁶ ≦ 3. It is presumed that this is because the ester group has steric hindrance on both sides, and nucleophilic attack on the ester bond is restricted. The above structure is, for example, (1) carbon number 2
A 1,2- or 2,3-alkylene oxide having 3 to 4 carbon atoms to an aliphatic polyhydric alcohol having 15 to 15 or polyhydric phenols having 6 to 50 or more carbon atoms and having 2 to 10 valences. And then reacted with methacrylic acid ester or methacrylic acid. (2) Introduced by reacting glycidyl group (introduced by addition of epichlorohydrin) with methacrylic acid and then reacting OH of secondary carbon with methacrylic acid (ester). You can do it. Therefore, (A) as a component of the coated flooring material of the present invention is a (poly) hydroxyl compound or (poly) epoxy such that part or all of the carbon bonded to Z is the above-mentioned secondary or higher carbon. If it is manufactured using a compound, when mixed with a polyepoxy compound and cured, a cured epoxy resin having high hydrolysis resistance can be obtained.

As described above, (A) has an ester group in the molecular structure, which has an HLB value (an index indicating hydrophilicity) of about 10 and a functional group having relatively high hydrophilicity. Also known as Further, although it depends on the HLB value of other functional groups contained in the molecular structure, the HL of the heterocyclic group
The B value is about 7.5. Therefore, the HLB value of (A) used for the coated flooring material of the present invention is preferably 4 to 15, particularly preferably 6 to 12. When the HLB value of (A) is 4 or more, the hydrolysis rate of the heterocyclic group is increased, and when it is 15 or less, the cured product has good water resistance. This HLB value is based on the Oda method. Since (A) has such an HLB value, it is mixed with a bisphenol-based or novolak-based epoxy resin having a low HLB value, which is usually used as a main ingredient, to form an epoxy resin-based coated flooring material which is one-packed. , Preferably having an HLB value of 4 or more. In addition, since (A) has good compatibility with the polyepoxy compound, it is presumed that the epoxy resin-based coated flooring material has a feature that moisture easily penetrates and a curing speed is extremely fast.

From the above, the HLB value is one factor that causes the heterocyclic-containing compound to have a higher curing rate than the ketimine compound conventionally used as the amine component of the one-component moisture-curable epoxy resin-based floor covering. That is, since the HLB value of the heterocyclic group is about 7.5, which is higher than the ketimine group having a value of 1.0 or less, it is estimated that the heterocyclic-containing compound takes in moisture more easily than the ketimine compound, and the curing rate is higher.

In (A), the number average molecular weight is usually 40
0 to 20,000, preferably 600 to 2,000. The number average molecular weight is measured by a gel permeation (GPC) method. TSKge as an example of measurement conditions
1 column (super H4000 + H30 manufactured by Tosoh Corporation)
00 + H2000), GPC-8120 (manufactured by Tosoh Corporation)
Is used. The viscosity at 25 ° C. is usually 200 to 200,000 cp, preferably 400 to 50,000 cp. The molecular weight per one heterocyclic group is usually from 150 to 2,000.
0, and preferably 200 to 500.

(A) reacts with moisture to form a ketone or aldehyde corresponding to a secondary amine easily bonded to a hydroxyalkyl group. Since the secondary amine bonded to the hydroxyalkyl group easily reacts with the epoxy group, (A) is useful as an epoxy resin curing agent. (A) is stable even in a system mixed with an epoxy resin unless water is mixed in from the outside. Therefore, the coated flooring material of the present invention can be used as a one-pack type and is very useful. is there.

In the coated flooring material of the present invention, the compounding amount of the epoxy resin curing agent comprising the heterocyclic compound (A) to the polyepoxy compound is equivalent to the heterocyclic group equivalent (A) represented by the general formula (1). It is preferable that the ratio of the polyepoxy compound to the epoxy equivalent is 0.4 to 2.5, particularly 0.5 to 2.0. By blending within this range, the epoxy group 1 of the polyepoxy compound
The number of active hydrogens in the secondary amine generated by hydrolysis of the heterocyclic group represented by the general formula (1) is 0.5 to 2.0, preferably 0.9 to 1. It can be one. When the number of active hydrogens is 0.5 or more and 2.0 or less, there is no decrease in curability, and good physical properties are exhibited without a decrease in water resistance and mechanical strength of the cured product.

As the polyepoxy compound, 2
It is not particularly limited as long as it has 10 to 10 epoxy groups,
It can be appropriately selected according to the use and purpose. Preferred are those having 2 to 6 epoxy groups in the molecule, and the epoxy equivalent (epoxy group 1) of the polyepoxy compound.
Molecular weight per unit) is usually 65 to 1,000,
Preferred is 90-500. Epoxy equivalent is 1,
When the molecular weight is not more than 000, the crosslinked structure does not become loose and the cured product has good physical properties such as water resistance, chemical resistance and mechanical strength. On the other hand, those having an epoxy equivalent of 65 or more can be easily synthesized. Examples of the polyepoxy compound include the following 1) to 7). 1) Glycidyl ether type (i) Diglycidyl ether of dihydric phenols Diglycidyl ether of dihydric phenols having 6 to 30 carbon atoms, for example, bisphenol F diglycidyl ether,
Bisphenol A diglycidyl ether, bishalogenated bisphenol A diglycidyl ether, tetrachlorobisphenol A diglycidyl ether, catechin diglycidyl ether, resorcinol diglycidyl ether, tetramethylbiphenyl diglycidyl ether,
Diglycidyl ether obtained from the reaction of 2 mol of bisphenol A with 3 mol of epichlorohydrin, etc .;

(Ii) trifunctional to hexafunctional or more,
Polyglycidyl ether of polyhydric phenols having 6 to 50 or more carbon atoms and a molecular weight of 250 to 3000
Polyglycidyl ethers of polyhydric phenols of 3 to 6 or more, such as pyrogallol triglycidyl ether, dihydroxynaphthyl cresol triglycidyl ether, tris (hydroxyphenyl) methane triglycidyl ether, dinaphthyltriol triglycidyl ether, tetrakis ( 4-hydroxyphenyl)
Ethanetetraglycidyl ether, p-glycidylphenyldimethyltolyl bisphenol A glycidyl ether, trismethyl-tert-butyl-butylhydroxymethanetriglycidyl ether, glycidyl ether of phenol or cresol novolak resin, glycidyl ether of limonene phenol novolak resin, resorcinol and acetone The polyglycidyl ether of a polyphenol having a molecular weight of 400 to 5000 obtained by the condensation reaction is exemplified. (Iii) Diglycidyl ether of an aliphatic alcohol Diglycidyl ether of a diol having 2 to 100 carbon atoms and a molecular weight of 150 to 5000, for example, ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, tetramethylene glycol diglycidyl ether, 1,6 -Hexanediol diglycidyl ether, polyethylene glycol (molecular weight 150 to 400
0) Diglycidyl ether, polypropylene glycol (molecular weight: 180-5000) diglycidyl ether, polytetramethylene glycol (molecular weight: 200-500)
0) Diglycidyl ether, neopentyl glycol diglycidyl ether, alkylene oxide of bisphenol A [ethylene oxide or propylene oxide (1
２０20 mol)] diglycidyl ether of adduct;

(Vi) Polyglycidyl ether of a trifunctional to hexafunctional or higher aliphatic alcohol having 6 to 50 or more carbon atoms and a molecular weight of 290 to 1000
Glycidyl ethers of trihydric to hexahydric or higher polyhydric alcohols of 0, for example, trimethylolpropane triglycidyl ether, glycerol triglycidyl ether, pentaerythritol tetraglycidyl ether;
Sorbitol hexaglycidyl ether, poly (n = 2
To 5) glycerol polyglycidyl ether and the like.

1) Glycidyl ester type A glycidyl ester of an aromatic mono- or polycarboxylic acid having 6 to 20 or more carbon atoms and having 1 to 6 or more functional groups, and 6 to 20 or more carbon atoms And glycidyl esters of aliphatic or alicyclic mono- or polycarboxylic acids having a monovalent to hexavalent or higher functional group number, such as glycidyl esters of fatty acids. (I) glycidyl esters of phthalic acids include diglycidyl phthalate, diglycidyl isophthalate, diglycidyl terephthalate, and the like;
(II) As the glycidyl ester of an aliphatic or alicyclic mono- or polycarboxylic acid, the aromatic nucleus water additive of the phenol-based glycidyl ester, diglycidyl dimer acid, diglycidyl oxalate, diglycidyl malate, diglycidyl malate, Glycidyl succinate, diglycidyl glutarate, diglycidyl adipate, diglycidyl pimerate, glycidyl (meth) acrylate (co)
Polymers.

3) Glycidylamine type Glycidylamine of aromatic amines having 6 to 20 or more carbon atoms and having 1 to 10 or more functional groups and glycidylamine of aliphatic amines are exemplified. Glycidylamines of aromatic amines include N,
N-diglycidylaniline, N, N-diglycidyltoluidine, N, N, N ', N'-tetraglycidyldiaminodiphenylmethane, N, N, N', N'-tetraglycidyldiaminodiphenylsulfone, N, N, N ',
N′-tetraglycidyldiethyldiphenylmethane,
N, N, O-triglycidylaminophenol and the like can be mentioned. As the glycidylamine of the aliphatic amine, N,
N, N ', N'-tetraglycidylxylylenediamine and its aromatic nuclei hydrogenated compound, N, N, N', N'-
Tetraglycidylhexamethylenediamine, trisglycidylmelamine and the like can be mentioned.

4) Chain aliphatic epoxide epoxidized polybutadiene, epoxidized soybean oil and the like. 5) Alicyclic epoxides having 6 to 50 or more carbon atoms and a molecular weight of 90 to 250
0, an alicyclic epoxide having 1 to 4 or more epoxy groups, for example, vinylcyclohexene dioxide, limonene dioxide, dicyclopentadiene dioxide, bis (2,3-epoxycyclopentyl) ether, ethylene glycol bisepoxydioxide Cyclopentyl ether, 3,4 epoxy-6-methylcyclohexylmethyl 3 ', 4'-epoxy-6'-methylcyclohexanecarboxylate, bis (3,4-epoxy-6-methylcyclohexylmethyl) adipate, and bis (3
4-epoxy-6-methylcyclohexylmethyl) butylamine and the like. It also includes a nuclear hydrogenated product of the phenolic epoxy compound. 6) A urethane-modified polyepoxy compound having a urethane bond in the structure; 7) A polyepoxy compound in which NBR, CTBN, silicone rubber, or the like is dispersed in a resin matrix. Other than 1) to 7), any epoxy resin having a glycidyl group capable of reacting with active hydrogen of an amine can be used. Preferred are glycidyl ethers, and particularly preferred are diglycidyl ethers of dihydric phenols and diglycidyl ethers of aliphatic alcohols. In addition, two or more of these polyepoxy compounds can be used in combination.

The coated flooring material of the present invention further comprises a dehydrating agent,
Adhesion imparting agent, anticorrosion imparting agent, curing accelerating catalyst, filler,
Contains at least one selected from the group consisting of aggregates, plasticizers, anti-coloring agents, leveling agents, antioxidants, pigments, dispersants, reactive diluents, solvents, water retention agents, wetting agents, and surfactants May be. The compounding amount is 50 parts by weight or less, preferably 30 parts by weight or less, particularly preferably 2 parts by weight or less based on the total weight.
0 parts by weight or less. The dehydrating agent is for preventing the water mixed in the coated flooring material of the present invention for any reason from reacting with the heterocycle and improving the storage stability of one-pack.
Examples of the dehydrating agent include a silane coupling agent, a monoisocyanate compound, a carbodiimide compound, and a zeolite. Specifically, vinyl trimethoxysilane,
Trimethyl orthoformate, 2,2-dimethoxypropane,
Synthetic zeolites and the like are mentioned, and vinyltrimethoxysilane and 2,2-dimethoxypropane are preferred. The mixing amount is 20 parts by weight or less, preferably 10 parts by weight, based on the amount of the coated flooring material.
Not more than parts by weight.

In order to increase the curing speed, a catalyst may be added as required. Examples of the catalyst for the hydrolysis reaction of the heterocycle (Z) include a phosphoric ester, p-toluenesulfonic acid, formic acid, acetic acid, propionic acid, dibutyltin dilaurate and the like. 2 generated by hydrolysis of heterocycle
Examples of the catalyst for the reaction between the tertiary amine and the epoxy group include tertiary amines, phenols, and triphenylphosphine. Of these, tertiary amines and phenols are preferred, and N, N-dimethylpropylamine, N, N,
Aliphatic tertiary amines such as N ', N'-tetramethylhexamethylenediamine; N-methylpyrrolidine, N, N'
-Alicyclic tertiary amines such as -dimethylpiperazine; aromatic tertiary amines such as benzyldimethylamine and dimethylaminomethylphenol are particularly preferred.

The adhesiveness-imparting agent is of course for improving the adhesiveness at the time of application under humid conditions, not to mention at the time of application under normal conditions, and especially for improving the adhesiveness of concrete containing water. Great effect. Examples of the adhesion-imparting agent include a silane coupling agent, a titanium coupling agent, an aluminum coupling agent and the like, and preferably a silane compound having a hydrolyzable silyl group. Examples of such a silane compound include vinylalkyl (C1-4) alkoxy (C1-4) silane [for example, vinyltrimethoxysilane, vinyltriethoxysilane, etc.], (meth) acryloyloxyalkyl (carbon number 1-4) alkoxy (1 to 4 carbon atoms) silane [for example, γ-methacryloxypropyltrimethoxysilane and the like], alkyl (1 to 4 carbon atoms) alkoxy (1 carbon atom)
~ 4) silanes [for example, methyltrimethoxysilane, methyltriethoxysilane, etc.], amino (1 to 4 in the molecule)
) Alkyl (C 2-15) alkoxy (C 1
4) silanes [e.g., γ- (2-aminoethyl) aminopropyltrimethoxysilane, aminopropyltrimethoxysilane, N-phenylaminopropylmethyldimethoxysilane, etc.], epoxy (1 to 4 per molecule) alkyl (carbon Formulas 1 to 4) alkoxy (1 to 4 carbon atoms) silane [for example, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethoxysilane, etc.], mercapto (1 to 4 in the molecule) alkyl ( C1-C4 alkoxy (C1-C4) silane [for example, γ-mercaptopropyltrimethoxysilane and the like] and the like. Of these, preferred are vinylalkylalkoxysilane, (meth) acryloyloxyalkylalkoxysilane, and epoxyalkylalkoxysilane, and particularly preferred are vinyltrimethoxysilane, γ-
Methacryloxypropyltrimethoxysilane and γ-glycidoxypropyltrimethoxysilane. The amount of these silane compounds used is 0.1% with respect to the epoxy resin.
５０50 parts by weight, preferably 1-10 parts by weight. 0.
Adhesiveness when it is 1 part by weight or more (especially adhesiveness on a wet surface)
If it is 50 parts by weight or less, it reacts with moisture during use and does not hinder ring opening of the heterocyclic group. These silane compounds may be used in combination of two or more.

Examples of the anticorrosive agent include metal powders such as zinc powder and aluminum powder, and zinc powder is particularly preferable.
Examples of the zinc powder include metal zinc powder and metal zinc alloy powder which are usually used for zinc-rich paint and zinc-rich primer, and metal zinc powder is particularly preferable. The zinc powder preferably has a particle size of usually 1 to 10 μm, and the amount of the zinc powder used can be selected according to the intended use, but is usually 20 to 95 parts by weight in the resin composition, preferably It is desirable to contain 30 to 80 parts by weight. 20
When the amount is not less than 95 parts by weight, the desired corrosion resistance is obtained, and when the amount is not more than 95 parts by weight, there is no adverse effect on the storage stability and coating film performance of the resin composition.

The filler is usually a finely pulverized solid, and the main purpose of the compounding is represented by performance such as strength and elastic modulus, durability such as weather resistance, conductivity and heat conductivity. This is an improvement in physical properties, an improvement in molding processability such as fluidity and shrinkage, or an improvement in economic aspects such as an increase in amount and resource saving. Fillers include magnesium silicate, calcium carbonate, carbon black, clay, talc, titanium oxide, quicklime,
Kaolin, zeolite, diatomaceous earth, vinyl chloride paste resin, vinylidene chloride resin balloon and the like,
They can be used alone or as a mixture. As the reactive diluent, a low-molecular-weight oxazolidine can be used in addition to a normal low-molecular-weight epoxy compound, a polyfunctional acrylate, and the like. These additives need to be sufficiently dehydrated before addition.

In order to improve the storage stability of the coated flooring material of the present invention, the polyepoxy compound together with the epoxy resin curing agent does not have active hydrogen, or has no active hydrogen. In this case, those having an active hydrogen equivalent of 4000 or more are preferable. The active hydrogen equivalent of the coated flooring material of the present invention is usually 2,000 or more, preferably 20,000 or more, and more preferably 40,000 or more. When the active hydrogen equivalent is less than 2,000, the storage stability of the coated flooring material is insufficient. If you have active hydrogen,
By inactivating the group having active hydrogen to a group that does not react with the epoxy resin, it is possible to make the active hydrogen-free group or the active hydrogen equivalent within a required range. The inactivation of the active hydrogen group can be performed by monoisocyanate compounds (ethyl isocyanate, n-butyl isocyanate, phenyl isocyanate, etc.), acid anhydrides (acetic anhydride, succinic anhydride), acid halides (benzoyl chloride, etc.) or alkyl halides (Methyl chloride, methyl bromide, ethyl chloride, etc.). The storage stability of the coated flooring material of the present invention is particularly excellent, and is also suitable as a one-pack type coated flooring material.

The actual curing reaction using the coated flooring material of the present invention is triggered by the reaction between moisture in the air and the heterocyclic compound. That is, since the curing reaction proceeds only from the surface that is in contact with air, when the proportion of the area of contact with air to the volume is small, such as when the coated floor material is in a container, the curing speed is remarkable. Become slow. Conversely, if the ratio of the surface area to the volume is increased by applying a thin coating, the curing speed is greatly increased to a practical level. Therefore, when the coated flooring material is in the container, the pot life is several tens to several hundred times longer than that of the conventional two-liquid type, and the unused coated flooring material can be used. It can be used repeatedly, and time and quantity restrictions during construction are greatly reduced. The curing temperature of the coated flooring material of the present invention is usually 5 ° C. or higher, preferably 10 to 100 ° C., particularly preferably 15 to 40 ° C. The humidity condition is preferably 20 to
100% R. H. And particularly preferably 30 to 80%.
R. H. It is. The curing time is a few minutes to 100 hours.

The operation of the construction method using the coated flooring material of the present invention can be carried out according to a conventional method.
As a painted floor, floors of buildings such as houses or various factories,
In addition to indoor floors and outer walls such as walls, corridors, and stairs, floors such as leisure facilities, sports facilities, transportation facilities, roads, and parking lots are included. Depending on the thickness of the coating or the shape of the floor surface, it is possible to apply any of the following methods: sinking method, mortar method, lining method, and coating method. From the aspect, a sink pan method or a coating method is preferable. As a coating method of the coating method, a general method such as brush coating, spray coating, and various coater coatings can be used. The coating amount of the coated flooring material of the present invention is not particularly limited, but is 10 to 300 μm for primer coating and 50 to 50 μm for base coating.
The thickness is preferably 30 to 300 μm in the case of 0 μm and top coat application, and the base coat application can be performed once to three times. Furthermore, in the top coat coating, a normal top coating can be used without particular limitation, for example, alkyd resin, epoxy resin, latex,
Paints such as silicone alkyd resin, urethane resin, silicone acrylic resin, and fluorine resin can be used.

[0049]

The present invention will be further described with reference to the following examples.
The present invention is not limited to this. In addition, a part shows a mass part below.

(Production Example) 1) Production of Heterocycle-Containing Compound In a reaction vessel equipped with a stirrer, a heating device, a cooling pipe and a reflux pipe equipped with a water separator, 1000 parts of methyl methacrylate, 200 parts of monoethanolamine, hydroquinone After charging 2.4 parts and reacting at 20 ° C. for 40 hours while passing air through the liquid, 3.6 parts of hydroquinone was added and excess methyl methacrylate was removed at 20 ° C. under reduced pressure. Next, 390 parts of acetone and 9.2 parts of paratoluenesulfonic acid were placed in a container,
Charged 400 parts of synthetic zeolite, sealed after nitrogen replacement,
A dehydration reaction was performed at room temperature for 10 hours while stirring. After the completion of the reaction, an acid adsorbent (KW-1000, manufactured by Kyowa Chemical Industry Co., Ltd.)
20 parts were charged and stirred at 20 ° C. for 3 hours. After cooling, diatomaceous earth A (manufactured by Showa Chemical Industry Co., Ltd .; Celite # 600) 10
The mixture was filtered as a filter aid, and acetone remaining in the filtrate was distilled off by heating to obtain an intermediate. The intermediate had a number average molecular weight of 201 and a viscosity (25 ° C .; B-type viscometer) of 120 cP.

In a similar reaction vessel, 500 parts of the intermediate M-1 and 6 moles of propylene oxide adduct of sorbitol 31
Then, 0 parts and 24 parts of sodium methylate were charged and the temperature was raised to 100 ° C. after the replacement with nitrogen to carry out a transesterification reaction. After neutralization, an acid adsorbent (KW-100 manufactured by Kyowa Chemical Industry Co., Ltd.)
0) 20 parts were charged and further stirred for 1 hour. Next, 10 parts of diatomaceous earth A was filtered at 70 ° C. as a filter aid to obtain heterocycle-containing compound A. HC-1 has a number average molecular weight of 1
725, molecular weight 297 per one heterocyclic group, viscosity (2
5 ° C .; B-type viscometer).

2) Production of one-pack type epoxy resin-coated flooring material Bisphenol F-type epoxy resin (manufactured by Yuka Shell Epoxy Co .; trade name: Epicoat 807) previously dehydrated at 80 ° C. and 20 mmHg at the ratios shown in Table 1. Resorcin diglycidyl ether (manufactured by Nagase Kasei Co .; trade name: Denacol EX)
-201) and heterocycle-containing compound A are stirred under reduced pressure, and then vinyltrimethoxysilane (manufactured by Dow Corning Toray Silicone Co., Ltd.) as a dehydrating agent, and γ-glycoxypropyltrimethoxysilane (Shin-Etsu Chemical Co., Ltd.) as an adhesion-imparting agent Co., Ltd.) and oxazolidine A (manufactured by San Apro Co .; trade name: ZOLDINE MS-PLUS) as a reactive diluent, and again stirred under reduced pressure to produce a one-pack type epoxy resin-based coated flooring material for primer. Further, magnesium silicate and zinc powder were added at the ratios shown in Table 2, and the mixture was stirred until it became uniform, thereby producing a one-pack type epoxy resin-based coated floor material for base coat.

(Comparative Production Example) In the same manner as in Production Examples 1 to 3, using Ketimine H (trade name: Epicure H-3, manufactured by Yuka Shell Epoxy Co., Ltd.), the primer and base coat were prepared according to the formulation examples shown in Tables 1 and 2. An epoxy resin coated flooring was manufactured.

Examples 1 to 3 and Comparative Example 1 The composition shown in Table 1 was used to compare the adhesiveness to concrete and the storage stability of the present invention and a one-pack type epoxy resin-based flooring material for a ketimine primer. The following items were evaluated. Table 1 shows the results. (i) Viscosity: Measured by a BL or BH type rotary viscometer at 20 ° C. under a nitrogen atmosphere. (ii) Drying time to the touch: One-part epoxy resin-coated floor material is JI
It was applied to a steel sheet specified in SA5400 using a 0.1 mm film applicator, cured at 20 ° C. and 65% humidity, and indicated by the time until the surface resin of the coating film did not stick to the finger. (iii) Appearance: The state of the coating film surface was visually observed. A glossy, swelling, no peeling, etc. was rated as ○, and a swelling, peeling, etc. was rated x. (iv) Pencil hardness, cross-cut test, abrasion resistance and chemical resistance: After applying a one-pack type epoxy resin-coated floor material to a steel sheet specified by JISA5400 using a 0.1 mm film applicator, the coating was applied at 20 ° C. The pencil hardness, cross-cut test, abrasion resistance and chemical resistance of the surface of the coating film cured at 65% humidity were performed in accordance with JIS5400. The chemical resistance was evaluated as ○ when there was no change, Δ when discolored, and X when swelling or peeling occurred.

(V) Adhesion strength: v-1: A composition having the composition shown in Table 1 was applied to a concrete plate and cultivated at 20 ° C. and 65% for 7 days. V-2: Dipped in water for 1 day. After that, take it out and apply it on a concrete plate wiped off with a lightly dry cloth.
With respect to the cured product cultivated at 5% for 7 days, the adhesive strength of each was measured with a single-axis Kenken-type adhesive strength tester, and the state of the adhesive surface layer was observed. When the material was broken by 100% concrete, the result was evaluated as ○. When the material was partially broken, the result was evaluated as Δ. (vi) Storage stability: A coated flooring material having the composition shown in Table 1 was placed in a sealed container purged with nitrogen, allowed to stand at 40 ° C. for 3 months, and the viscosity was measured by the same method as described above. The composition was further applied and cured, and the dry time to the touch and the adhesion strength were measured.

As shown in Table 1, the one-pack type epoxy resin-based coated flooring materials of Examples 1 to 3 had cured properties such as adhesion strength, storage stability, abrasion resistance and chemical resistance, as compared with ketimine-based flooring materials. In both cases, good results were obtained.

Example 4 and Comparative Example 2 In order to compare the curing performance and the storage stability of the present invention and a one-pack type epoxy resin-based coated flooring material for a ketimine-based base coat, the following items were added in the composition shown in Table 2. evaluated. Table 2 shows the results. (i) Adhesion to primer: The adhesion to the primer resin of Example 3 and Comparative Example 1 was measured with a single-screw type Kenken-type adhesion tester, and observed by the state of the adhesive surface layer at that time. . The material whose 100% concrete material was destroyed was evaluated as ○, the material whose material was partially destroyed was evaluated as △, and the material peeled off at the interface between the primer resin and the base coat resin was evaluated as ×. Other items are the same as those in Table 1.

[0058]

[Table 1]

[0059]

[Table 2]

As shown in Table 2, the one-pack type epoxy resin-based coated flooring material of Example 4 exhibited better results in both curing performance and storage stability than the ketimine-based flooring material.

[0061]

Accordingly, the coated flooring material of the present invention has the following effects. (1) It has excellent storage stability. (2) It has excellent wet surface adhesion. (3) It has excellent cured physical properties such as abrasion resistance and chemical resistance, so it is very useful as a coated flooring material. Further, it is also suitable as a one-pack type coated floor material. Therefore, it is possible to significantly reduce the amount of waste, and when using a one-pack type, a quantitative error in blending the main agent and the curing agent, which is a disadvantage of the two-pack type,
Poor mixing due to poor mixing or excess pot life and poor applicability due to pot life variations due to temperature changes in the workplace can be eliminated.

Claims (10)

[Claims] An epoxy resin-coated flooring material comprising a heterocyclic group-containing compound (A) having two or more heterocyclic groups (Z) represented by the following general formula (1) and a polyepoxy compound. Embedded image (Wherein, R represents a linear or branched alkylene group having 2 to 10 carbon atoms which may contain -O- and / or -S-, R
¹ and R ² may be the same or different, and may be a hydrogen atom, a linear or branched C 1-6
An alkyl or alkenyl group of the formula
Represents an aryl group having 8 to 8 carbon atoms, or represents a cycloalkyl ring having 5 to 7 carbon atoms together with the carbon atom to which R ¹ and R ² are bonded. R ³ represents an alkylene group having 1 to 10 carbon atoms. ) 2. (A) has at least one main chain selected from the group consisting of hydrocarbons which may have a hydroxyl group in a side chain, polyether, polyvinyl, polyester, polyamide, polycarbonate and novolak. The epoxy resin-based floor material according to claim 1. 3. The method according to claim 1, wherein (A) is a compound represented by the following general formula (2) to
The epoxy resin-coated flooring material according to claim 1 or 2, which is a compound having a main chain structure represented by at least one selected from the group consisting of: Embedded image 4. The method according to claim 1, wherein (A) is a compound represented by the above general formula (2) or (3).
The epoxy resin-based floor covering according to claim 3, which is a compound having a main chain structure represented by at least one selected from the group consisting of (4) and (4). 5. The epoxy resin-based coated flooring material according to claim 3, wherein (A) is a compound having a main chain structure represented by the general formula (2). 6. The epoxy resin-coated flooring material according to claim 1, wherein said (A) is a compound represented by the following general formula (11). Embedded image [In the formula, A ¹⁰ is a residue obtained by removing a hydroxyl group from k-valent polyhydric alcohols and k-valent polyhydric phenols.
A ^o is a linear or branched alkylene group having 2 to 4 carbon atoms, p and q are 0 or an integer of 1 to 10, and may be the same or different. r is 0 or 1
It is. Z ¹ represents OH or Z. Q ³ is a hydrogen atom or a glycidyl group. m is 1 or an integer of 2 to 10, k is 2
Is an integer of 10 to 10 and k ≧ m. m + r ≧ 2. When m = 1, Z ¹ is Z. p, q, r, A ^o , Z ¹
And when there are a plurality of Q ^{3 s} , they may be the same or different. ] 7. In the coated flooring material, the amount of active hydrogen generated when the heterocyclic group (Z) is decomposed by moisture is 0.5 to 2 to 1 equivalent of the epoxy group of the polyepoxy compound.
The epoxy resin-based coated flooring material according to any one of claims 1 to 6, comprising a heterocyclic-containing compound in an amount equivalent to 0 equivalent. 8. A dewatering agent, further comprising:
Adhesiveness-imparting agent, anticorrosion-imparting agent, filler, curing acceleration catalyst,
One or more additives selected from the group consisting of aggregates, plasticizers, anti-coloring agents, leveling agents, antioxidants, pigments, dispersants, reactive diluents, solvents, water retention agents, wetting agents, and surfactants The epoxy resin-based flooring material according to any one of claims 1 to 7, further comprising an agent. 9. The epoxy resin-based flooring material according to claim 8, wherein the additive is an adhesion-imparting agent. 10. The epoxy resin-based coated flooring material according to claim 1, wherein said adhesion-imparting agent is a silane coupling agent.