JP2003261830A - Primer and method for forming cured layer by using the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a primer which exhibits excellent (moisture) rapid curability and water-resistant adhesion even at low temperatures by bringing it into contact with a major agent composed of an isocyanate group-containing prepolymer, is suited, for example, for adhesion, coating, sealing and the like in a high-speed line production at normal temperatures and, simultaneously, has good storage stability and does not cause any environment problem or the like, and a method for forming a cured layer by using this primer. <P>SOLUTION: The primer comprises at least a urea based compound having a group for forming a primary and/or secondary amino group by the reaction with water, and the method for forming a cured layer uses this primer. <P>COPYRIGHT: (C)2003,JPO

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a primer which realizes excellent (moisture) rapid curing property even at low temperature, and a method for forming a cured layer using the primer.

[0002]

2. Description of the Related Art Conventionally, in the fields of construction, civil engineering, automobiles, etc., a high-speed production line including a process for adhering various boards and members such as steel plates, slate boards, concrete boards, resin concrete boards, wood boards and plastic boards. In this case, for example, a two-pack type polyurethane adhesive agent having an isocyanate group-containing polyurethane resin as a main agent and a low-molecular amine as a curing agent is used. Further, there is also known a polyurethane-based solventless primer composition containing an isocyanate group, which has a low melt viscosity, a good adhesive property, and a fast initial hardness development (see JP-A-9-78028). This primer composition comprises two kinds of urethane prepolymers and a latent curing agent, and the latent curing agent is N-hydroxyethyl-2-isopentyloxazolidine, its XDI adduct, other oxazolidine, and the like.

[0003]

However, the above-mentioned conventionally known two-component polyurethane-based adhesive requires time and effort for mixing the main agent and the curing agent, and the adhesive strength is not sufficient for bonding at low temperature in a high-speed production line. There are problems that the expression is slow and low molecular weight amine has high toxicity. In addition, the solventless primer composition has a problem that storage stability, adhesive strength development, water-resistant adhesiveness, etc. are insufficient.

The present invention exhibits excellent (moisture) fast curing property and water-resistant adhesive property even at low temperature by bringing it into contact with a main agent composed of an isocyanate group-containing prepolymer. For example, adhesion and coating in high-speed line production at room temperature. An object of the present invention is to provide a primer suitable for sealing, etc., which has good storage stability and does not cause environmental problems, and a method for forming a cured layer using the primer.

[0005]

In order to achieve the above-mentioned object, the present invention comprises a urea compound having a group which reacts with water to form a primary and / or secondary amino group. , Which is a primer.

The present invention provides a urea compound having a group which reacts with water to form a primary and / or secondary amino group, and a group which reacts with a primary and / or secondary amino group. And a compound having.

The present invention provides a urea compound having a group which reacts with water to form a primary and / or secondary amino group, and a group which reacts with the primary and / or secondary amino group. Containing a compound having, and a polyurethane resin,
Is a primer.

The present invention is the second or third primer, wherein the compound having a group that reacts with the primary and / or secondary amino group is an epoxy resin.

The present invention is each of the above-described primers further containing a catalyst.

According to the present invention, a primer layer and a base material layer made of an isocyanate group-containing prepolymer are provided between a first base material and a second base material, and then the first base material and the second base material are provided. A method for forming a cured layer in which a base material is pressed against each other to react a primer and a main agent, wherein the primer layer is a layer composed of each of the above-mentioned primers.

In the present invention, a primer layer is provided on each surface of a first substrate and a second substrate which face each other, and a base material comprising an isocyanate group-containing prepolymer on either or both of the primer layers. A method for forming a cured layer, in which a layer is provided, and then a first base material and a second base material are pressed against each other to react a primer and a base material, the primer layer comprising the above-mentioned respective primers The above method is characterized in that

[0012]

BEST MODE FOR CARRYING OUT THE INVENTION The present invention is described in detail below.
The urea-based compound having a group that reacts with water (moisture) to form a primary and / or secondary amino group in the present invention specifically includes a primary and / or a secondary compound that reacts with water. A compound obtained by reacting a compound having a group that forms a secondary amino group and a primary and / or secondary amino group with an organic polyisocyanate is preferable.

As the compound having a group which reacts with water to form a primary and / or secondary amino group and a primary and / or secondary amino group, specifically, raw materials are available. From the viewpoint of easiness, reactivity with water, etc., a ketimine compound of a compound having a primary and / or secondary amino group, an enamine compound, an aldimine compound, or an arbitrary mixture thereof, which has a Preferable examples include those containing one or more (preferably one) free primary and / or secondary amino groups. These ketimine compounds,
Enamine compounds, aldimine compounds, etc. are primary and / or primary compounds of compounds having a total of two or more primary and / or secondary amino groups and carbonyl groups (keto group, aldehyde group) of ketones and aldehydes, respectively. Alternatively, it can be obtained by a dehydration reaction with a part of one or more secondary amino groups so as to leave one or more secondary amino groups. Among these, from the viewpoint of ease of production and what is produced by reaction with water when used are a urea compound having a primary and / or secondary amino group and a ketone compound having low toxicity. Ketimine compounds having a primary and / or secondary amino group are preferred.

A total of 2 primary and / or secondary amino groups
As the compound having at least one, ethylenediamine, 1,
3-diaminopropane, 1,2-diaminopropane,
1,4-diaminobutane, hexamethylenediamine,
1,7-diaminoheptane, trimethylhexamethylenediamine, 1,8-diaminooctane, 1,9-diaminononane, 1,10-diaminodecane, 1,11-diaminoundecane, 1,12-diaminododecane, 1,1
3-diaminotridecane, 1,14-diaminotetradecane, 1,15-diaminopentadecane, 1,16-diaminohexadecane, 1,17-diaminoheptadecane, 1,18-diaminooctadecane, 1,19-diaminononadecane, 1,20-diaminoeicosane, 1,
21-diaminogenticosan, 1,22-diaminodocosane, 1,23-diaminotricosane, 1,24-diaminotetracosane, isophoronediamine, diaminodicyclohexylmethane, 3,9-bis (3-aminopropyl) ) -2,4,8,10-Tetraoxaspiro (5,
5) undecane, xylenediamine, phenylenediamine, diaminodiphenylmethane, diaminodiethylphenylmethane, polyoxyethylenediamine, polyoxypropylenediamine, tri (methylamino) hexane,
N-laurylpropylenediamine, N-stearylpropylenediamine, diethylenetriamine, triethylenetetramine, methylaminopropylamine, 3,3'-
Examples thereof include polyamines such as diaminodipropylamine, and these can be used alone or in admixture of two or more. Of these, a polyamine having a primary amino group and a secondary amino group is preferable, which is easy to produce by utilizing the difference in reactivity between a carbonyl group and a primary amino group, and a secondary amino group, and particularly preferable. Diethylenetriamine is preferred.

Examples of the ketones include methyl ethyl ketone, methyl isopropyl ketone, methyl isobutyl ketone, methyl-tert-butyl ketone, 2-pentanone, 3-pentanone, 2-hexanone and 4-methyl-.
Aliphatic ketones such as 2-pentanone, 2-heptanone, 4-heptanone, diisopropyl ketone and diisobutyl ketone, aromatic ketones such as propiophenone and benzophenone, cyclic ketones such as cyclopentanone, cyclohexanone and methylcyclohexanone, Examples include β-dicarbonyl compounds such as ethyl acetoacetate, or any mixture thereof. Of these, aliphatic ketones are preferable, and methyl isobutyl ketone is particularly preferable, from the viewpoints of ease of production and low toxicity of those that are formed by reaction with water when used. Aldehydes include, for example, butyraldehyde, isobutyraldehyde, hexyl aldehyde, or any mixture thereof.

As the organic polyisocyanate, phenylene diisocyanate, diphenyl diisocyanate,
Naphthalene diisocyanate, diphenylmethane diisocyanate, tolylene diisocyanate, aromatic diisocyanate such as diphenyl ether diisocyanate, araliphatic diisocyanate such as xylylene diisocyanate, hexamethylene diisocyanate, pentamethylene diisocyanate, propylene diisocyanate, aliphatic diisocyanate such as butylene diisocyanate, cyclohexane diisocyanate, Examples thereof include alicyclic diisocyanates such as methylene bis (cyclohexyl isocyanate) and isophorone diisocyanate (IPDI). Further, so-called modified isocyanates such as buret modified products, isocyanurate (trimerized) modified products, uretonimine modified products, uretdione modified products, and carbodiimide modified products of these organic diisocyanates are also included. Further, polyisocyanates called so-called polymeric compounds such as polyphenylene polymethylene polyisocyanate and crude toluene polyisocyanate can also be mentioned. Further, an isocyanate group-containing urethane resin obtained by reacting the above-mentioned organic polyisocyanate with a polymer polyol or a chain extender described below under conditions of excess of isocyanate groups with respect to active hydrogen groups can also be mentioned. These can be used alone or in admixture of two or more.

The urea compound having a group which reacts with water to form a primary and / or secondary amino group is preferably a primary and / or secondary compound which reacts with water. A compound having an amino group-forming group and a primary and / or secondary amino group, and the organic polyisocyanate are preferably used, in which the equivalent ratio of the primary and secondary amino groups / isocyanate groups is 0.5-2.0 / 1.0, 0.9-1.1 /
It can be obtained by reacting in the range of 1.0. The urea compound having a group that reacts with water to form a primary and / or secondary amino group, which is obtained in this manner, firstly has a primary and / or secondary amino group formed by moisture. The resulting group is decomposed to generate a primary and / or secondary amino group, and then these generated primary and / or secondary amino groups contain an isocyanate group as a main agent (described later). The cured layer is formed by reacting with an isocyanate group of the prepolymer, and optionally a polyurethane resin (described later) or a compound having a group that reacts with primary and / or secondary amino groups.

Specific examples of the compound having a group which reacts with the primary and / or secondary amino group in the present invention include:
Examples thereof include epoxy compounds, the above-mentioned organic polyisocyanates, and (meth) acryloyl group-containing compounds. Of these, epoxy compounds are preferable. These can be used alone or in admixture of two or more. Examples of the epoxy compound include an epoxy resin, an epoxy group-containing urethane resin, and an epoxy-based silane coupling agent. Specifically, as the epoxy resin, epichlorohydrin-bisphenol A type epoxy resin, epichlorohydrin-bisphenol F type epoxy resin, flame retardant type epoxy resin such as glycidyl ether of tetrabromobisphenol A, novolac type epoxy resin, hydrogenated bisphenol A Type epoxy resin, glycidyl ether type epoxy resin of bisphenol A propylene oxide adduct, p-oxybenzoic acid glycidyl ether ester type epoxy resin, m-aminophenol type epoxy resin, diaminodiphenylmethane type epoxy resin, urethane modified epoxy resin, various fats Cyclic epoxy resin, N, N
-Diglycidylaniline, N, N-diglycidyl-o-
Examples thereof include toluidine, triglycidyl isocyanurate, polyalkylene glycol diglycidyl ether, glycidyl ether of polyhydric alcohol such as glycerin, hydantoin type epoxy resin, and epoxidized unsaturated polymer such as petroleum resin. As the epoxy group-containing urethane resin, the isocyanate of the isocyanate group-containing urethane resin obtained by reacting the above-mentioned organic polyisocyanate and a polymer polyol or a chain extender described below under the condition of an excess of isocyanate groups with respect to active hydrogen groups. With respect to the group, a compound in which an epoxy group such as glycidyl alcohol and a compound containing a hydroxyl group are reacted with an isocyanate group under the condition of an active hydrogen group in an approximately equivalent amount to introduce an epoxy group into a urethane resin. . Examples of the epoxy-based silane coupling agent include 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, and 3-glycidoxypropylmethyldiisopropenoxysilane. (Meta)
Examples of the acryloyl group-containing compound include monofunctional (meth) acrylic acid alkyl esters such as (meth) acrylic acid ethyl ester, and trimethylolpropane tri (meth)
Examples thereof include polyfunctional (meth) acrylic acid esters such as acrylate. Of these, epoxy resins are preferable, and epichlorohydrin-bisphenol A type epoxy resins are particularly preferable, from the viewpoint of good water-resistant adhesion after adhesion.

In the primer of the present invention, the compound having a group which reacts with a primary and / or secondary amino group has a group which reacts with water to form a primary and / or secondary amino group. 1 to 50 relative to 100 parts by weight of urea compound
It is preferably blended in an amount of 0 part by weight, more preferably 5 to 50 parts by weight.

The polyurethane resin in the present invention comprises the above-mentioned organic polyisocyanate, a high molecular weight polyol, and
In some cases, it is obtained by further reacting a chain extender with an active hydrogen group with respect to an isocyanate group under substantially equivalent conditions.

As the polymer polyol, polyester polyol, polyester amide polyol, polyether polyol, polyether ester polyol,
Polycarbonate polyols, acrylic polyols and the like can be mentioned, and these can be used alone or in admixture of two or more. Of these, polyester polyols are preferred. These have a number average molecular weight of 500 or more, and further 100
The thing of 0-30,000 is preferable from a point, such as workability and adhesive strength expression. Examples of polyester polyols and polyester amide polyols include known dicarboxylic acids such as succinic acid, adipic acid and terephthalic acid, their acid esters and acid anhydrides, and ethylene glycol, propanediol, butanediol, pentanediol and hexane. Low molecular weight polyols such as diol, neopentyl glycol, trimethylolpropane, glycerin, quadrol, ethylene oxide or propylene oxide adduct of bisphenol A, low molecular weight polyamines such as ethylenediamine and diethylenetriamine, amino alcohols such as monoethanolamine, etc. Or the compound obtained by the dehydration condensation reaction with these mixtures is mentioned. Further, a lactone-based polyester polyol obtained by the cleavage polymerization of a cyclic ester (that is, lactone) monomer such as ε-caprolactone can be used. Examples of the polyether polyol include polyoxyethylene polyol and polyoxypropylene polyol. Examples of the polyether ester polyol include compounds produced from the above polyether polyol and the above dicarboxylic acid, acid ester, acid anhydride and the like. Examples of the polycarbonate polyol include compounds obtained by reacting the low molecular weight polyol used in the production of the polyester polyol with diethyl carbonate, diphenyl carbonate, or the like. As the acrylic polyol, for example, 2-hydroxyethyl acrylate, hydroxypropyl acrylate, 2-hydroxyethyl methacrylate,
Acrylic acid-based compound monomer containing a hydroxyl group such as hydroxypropyl methacrylate and / or a methacrylic acid-based compound monomer containing a hydroxyl group (and optionally one or more ethylenically unsaturated compounds other than these, ) Those obtained by reacting by a known radical polymerization method such as batch polymerization or continuous polymerization in the presence or absence of a radical polymerization initiator and in the presence or absence of a solvent. In addition, polyamide resins, polyester resins and the like having an active hydrogen group and having a number average molecular weight of 500 or more, which are generally known in the polyurethane industry, can also be mentioned.

As the chain extender, a molecular weight of 500 among low molecular weight polyols, low molecular weight polyamines, amino alcohols and the like used in the synthesis of the above polyester polyol is used.
And the mixtures thereof and the like.

Polyurethane-based resin is produced by the one-shot method,
It can be synthesized by any of the two-shot methods. The equivalent ratio (active hydrogen group / isocyanate group) of the isocyanate group of the organic polyisocyanate and the active hydrogen group of the polymer polyol (and optionally the chain extender) is preferably 0.9 to 1.1. The number average molecular weight of polyurethane resin is 1,0
00 to 1,000,000, and further 3,000 to 200,
It is preferably 000. Number average molecular weight is 100
When it is less than 0, the adhesive strength is poorly expressed,
If it exceeds 50,000, the viscosity is increased and the workability is deteriorated.

In the primer of the present invention, the polyurethane resin is 1 to 500 parts by weight based on 100 parts by weight of the urea compound having a group which reacts with water to form primary and / or secondary amino groups. Further, it is preferable to add 10 to 50 parts by weight.

As the catalyst in the present invention, known urethanization of organic metal compounds such as dibutyltin dilaurate, dioctyltin dilaurate and tin octylate, organic amines such as triethylenediamine, triethylamine and tri-n-butylamine and salts thereof and the like. Examples include catalysts.

In the primer of the present invention, the catalyst is used in an amount of 0.0 to 100 parts by weight of a urea compound having a group which reacts with water to form a primary and / or secondary amino group.
It is preferable to add 1 to 20 parts by weight, and more preferably 0.1 to 10 parts by weight.

The isocyanate group-containing prepolymer as the main component in the present invention contains the above-mentioned organic polyisocyanate, high molecular weight polyol, and optionally a chain extender, in excess of isocyanate groups with respect to active hydrogen groups. It can be obtained by reacting under the conditions, and these can be used alone or in combination of two or more kinds.

The primer and main agent of the present invention include antioxidants (hindered amine type, hindered phenol type, etc.), coupling agents, various inorganic fillers and organic fillers, thixotropic agents, storage stability improving agents, plasticizers, Various additives such as colorants can be blended. These additives can be blended in either or both of the primer side and the main agent side.

The method for forming a hardened layer of the present invention is as follows.
Between the base material and the second base material, a primer layer and a main agent layer made of an isocyanate group-containing prepolymer are provided.
Then, the first base material and the second base material are pressed against each other to react the primer with the main agent. Further, a primer layer is provided on each of the opposing surfaces of the first base material and the second base material, a main agent layer made of an isocyanate group-containing prepolymer is provided on one or both of the primer layers, and then the In this method, the first base material and the second base material are pressed against each other to react the primer with the main agent. The method of the present invention, for example, in a production line of a factory, a base material layer and a primer layer are separately formed on the surfaces of boards and members such as steel plate, slate plate, concrete plate, resin concrete plate, wood plate and plastic plate. Suitable for high-speed bonding in which the bonding surfaces (the surface of the main agent layer and the surface of the primer layer) are opposed and pressed at room temperature with a vise, a weight, a roll, or the like. After forming the primer layer and the main agent layer on each substrate, before exposing and adhering the layers so that they face each other, the step of exposing the surface of each layer to atmospheric humidity (open) Time may or may not be included. A short open time of 30 minutes or less is sufficient, but it may exceed 30 minutes.

Since the primer of the present invention can be applied under the conditions of room temperature and humidity and cured by reacting with the main agent layer, there is a point that it is not necessary to use a special heating device or the like, but the curing operation can be accelerated. Therefore, it is possible to heat or humidify if necessary. As a specific application method, brushes,
There is a conventionally known method such as a method of applying using a trowel such as a comb iron, a spatula, a roll coater, or a method of spray application.

[0031]

[Synthesis of ketimine compound]

Synthesis Example 1 103.2 g (1 mol) of diethylenetriamine was placed in a stirring vessel equipped with a heating device and an ester tube, and then 260.4 g (2.6 mol) of methyl isobutyl ketone was added with stirring. After further adding 64.2 g of toluene to this, the mixture was heated and stirred at 100 to 130 ° C. for 6 to 7 hours, and 34.2 g of water was dehydrated through an ester tube. Then, the pressure was reduced to remove toluene to obtain a ketimine compound of diethylenetriamine having about one secondary amino group in the molecule. This is called ketimine compound A.

Synthesis Example 2 After 60.1 g (1 mol) of ethylenediamine was placed in a stirring container equipped with a heating device and an ester tube, 260.4 g (2.6 mol) of methyl isobutyl ketone was added with stirring. After further adding 64.2 g of n-hexane thereto, the mixture was heated and stirred at 100 to 130 ° C. for 6 to 7 hours, and 34.2 g of water was dehydrated through an ester tube. Then, the pressure was reduced to remove n-hexane to obtain a ketimine compound of ethylenediamine. This is called ketimine compound B.

[Preparation of Primer] Example 1 To a reaction vessel equipped with a heating device, a stirrer, a thermometer, a nitrogen seal tube and a condenser, 300.0 g of ethyl acetate and 230.0 g of toluene were added, and further added thereto. Isophorone diisocyanate (IPDI) trimerized polyisocyanate (V
(ESTANOTT-1890, manufactured by Huls Japan)
After 70.0 g was added and dissolved, 84.0 g of the ketimine compound A obtained in Synthesis Example 1 was added with stirring, and the mixture was stirred and reacted at 30 to 40 ° C. for 1 hour to synthesize a ketimine group-containing urea compound. The disappearance of the peak of the isocyanate group was confirmed by FTIR in the obtained reaction solution. This solution was used as a primer.

Example 2 Reaction solution (primer) obtained in the same manner as in Example 1
13.0 g of 3-glycidoxypropyltrimethoxysilane (A-187, manufactured by Nippon Unicar Co., Ltd.) was added thereto, and the mixture was stirred at room temperature for 30 minutes to prepare a primer.

Example 3 Reaction solution (primer) obtained in the same manner as in Example 1
13.0 g of 3-glycidoxypropyltrimethoxysilane (A-187, manufactured by Nippon Unicar Co., Ltd.) and tin octylate (Stannoct, manufactured by Yoshitomi Fine Chemical Co., Ltd.)
4.1 g was added and stirred at room temperature for 30 minutes to prepare a primer.

Example 4 Reaction solution (primer) obtained in the same manner as in Example 1
Polyester polyurethane resin (Nipporan 3
022, manufactured by Nippon Polyurethane Industry Co., Ltd.) 36.0 g and 3
-Glycidoxypropyltrimethoxysilane (A-18
7) (manufactured by Nippon Unicar Co., Ltd.) and 4.1 g of tin octylate (Stannoct, manufactured by Yoshitomi Fine Chemical Co., Ltd.) were added and stirred at room temperature for 30 minutes to prepare a primer.

Example 5 Reaction solution (primer) obtained in the same manner as in Example 1
36.0 g of epoxy resin (Epicoat 828, manufactured by Yuka Shell Epoxy Co., Ltd.), 36.0 g of polyester-based polyurethane resin (Nipporan 3022, manufactured by Nippon Polyurethane Industry Co., Ltd.), and 3-glycidoxypropyltrimethoxysilane ( A-187, manufactured by Nippon Unicar Co., Ltd.) 13.0
g and 4.1 g of tin octylate (Stannoct, manufactured by Yoshitomi Fine Chemical Co., Ltd.) were added and stirred at room temperature for 30 minutes to prepare a primer.

Comparative Example 1 300.0 g of ethyl acetate and 230.0 g of toluene were added to a reaction vessel equipped with a heating device, a stirrer, a thermometer, a nitrogen seal tube and a condenser, and further isophorone diisocyanate (IPDI) was added thereto. Of trimerized polyisocyanate (V
(ESTANOTT-1890, manufactured by Huls Japan)
After 70.0 g was added and dissolved, 70.0 g of the ketimine compound B obtained in Synthesis Example 2 was added and mixed with stirring. Then, 4.1 g of tin octylate (Stannocto, manufactured by Yoshitomi Fine Chemical Co., Ltd.) was added to this mixed solution, and the mixture was allowed to stand at room temperature for 30 minutes.
The primer was prepared by stirring for 1 minute.

Comparative Example 2 A primer was prepared in the same manner as in Comparative Example 1 except that the ketimine compound B was not used.

[Storage Stability] The appearance of each primer obtained in Examples 1 to 5 and Comparative Examples 1 and 2 when stored at 50 ° C. for 10 days was visually evaluated. Judgment criteria ○: No change (transparent) ×: White turbidity

[Performance Test] Examples 1 to 5 and Comparative Example 1,
Using each of the primers obtained in 2 and the urethane-based sealing material, an adhesion test was conducted as follows. 5 ° C, 40%
FRP of 10 mm x 35 mm x 25 mm in RH environment
A primer is applied by brush onto both sides of the plate bonding area of 25 mm x 25 mm, and immediately a urethane-based sealing material (auto sealer 101R, manufactured by Auto Kagaku Kogyo Co., Ltd.) consisting of an isocyanate group-containing prepolymer is applied from the cartridge on only one side. It was cast so as to have a weight of 0.5 g / cm ² , adhered thereto, and clamped with a clip. After 1 hour, 2 hours, and 6 hours, take out and compress at 2.0m.
The compression shear adhesive strength was measured at m / min (JIS
K6852 compliant). Further, the adhesive test piece which was adhered in the same manner as described above and clamped with a clip was aged for 7 days under the conditions of 23 ° C. and 50% relative humidity, and the clip was removed and immersed in warm water of 50 ° C. for 7 days. Afterwards, it was crushed by compression and tested for water resistant adhesion. The state of the destroyed interface was visually observed and judged. Criteria ◎: 100% cohesive failure of the sealing material ○: 50% or more and less than 100% of the cohesive failure of the sealing material (the remainder is peeling at the interface of the adherend) ×: Cohesive failure of the sealing material is less than 50% ( The rest is peeling at the interface of the adherend.) These results are summarized in Table 1.

[0042]

[Table 1]

[0043]

As described above, according to the present invention, by bringing it into contact with the main agent composed of the isocyanate group-containing prepolymer, excellent (moisture) rapid curing property and water-resistant adhesive property are exhibited even at low temperature, for example, at room temperature. It has become possible to provide a primer suitable for adhesion, coating, sealing, etc. in high-speed line production, having good storage stability and not causing environmental problems, and a method for forming a cured layer using the primer. .

─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. ⁷ Identification code FI theme code (reference) C09D 175/04 C09D 175/04 C09J 5/02 C09J 5/02 5/04 5/04 175/04 175 / 04 // C08L 101: 00 C08L 101: 00 F-term (reference) 4F071 AA01 AA53A CA01 CB02 CC05 CD01 4J038 DB001 DB021 DB061 DB071 DB481 DG001 DG111 DG121 DG131 DG271 DG281 GA09 JA32 JB23 JB24 KA03 PA06 MA08MAEF02 MAEF08MAEF02

Claims (7)

[Claims] 1. A primer comprising a urea compound having a group which reacts with water to form a primary and / or secondary amino group. 2. A urea compound having a group which reacts with water to form a primary and / or secondary amino group, and a compound having a group which reacts with a primary and / or secondary amino group. And a primer. 3. A urea compound having a group which reacts with water to form a primary and / or secondary amino group, and a compound having a group which reacts with a primary and / or secondary amino group. And a polyurethane-based resin. 4. The primer according to claim 2, wherein the compound having a group that reacts with the primary and / or secondary amino group is an epoxy resin. 5. The primer according to claim 1, further comprising a catalyst. 6. A primer layer and a base material layer made of an isocyanate group-containing prepolymer are provided between the first base material and the second base material, and then the first base material and the second base material. Is a method of forming a cured layer in which a primer and a base material are reacted by pressing each other, wherein the primer layer is a layer including the primer according to any one of claims 1 to 5. The method as described above. 7. A primer layer is provided on each of opposing surfaces of a first substrate and a second substrate, and a main agent layer made of an isocyanate group-containing prepolymer is provided on one or both of the primer layers. A method for forming a cured layer, in which the first base material and the second base material are then pressed against each other to react the primer and the main agent, wherein the primer layer is any one of claims 1 to 5. A layer comprising the primer according to 1.