JP3315460B2 - Non-foamed urethane curable composition - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention provides a cured product which cures at room temperature, has high flexibility, high elongation and high flame retardancy.
Sealing material, waterproof material, about the suitable non-foamed urethane curable composition as an adhesive material.

[0002]

BACKGROUND OF THE INVENTION terminated polyurethane prepolymer having an isocyanate group, alone in one part composition is cured reacted with moisture in the atmosphere, or two-part cured by mixing with active hydrogen compound composition It is used as an object.

[0003] These one-composition or two-part curable composition of the sealing material, structural adhesive, waterproof material, or building materials such as flooring has been widely used in fields such as civil engineering materials. In recent years, with the diversification of architecture and civil engineering styles, more flexible, high elongation, high flame retardant sealing materials, structural adhesives,
There is a need for waterproof materials.

On the other hand, dispersion of the nanoparticle dispersoids aldehyde condensation resin to the port re polyether polyol as a dispersion medium is, JP-B as rigid polyurethane foam raw material 57
It is publicly known, for example, from -14708.

[0005]

According to the study of the present inventors, the fine particle-dispersed polyol containing the above-mentioned ordinary polyether polyol as a dispersion medium is effective in imparting flame retardancy, It has been found that it is not necessarily suitable as a raw material for the sealing material or the like that requires high flexibility, high elongation and high mechanical strength.

That is, in the above-mentioned fine particle-dispersed polyol, the polyether polyol as a dispersion medium has a relatively small molecular weight (has a relatively large hydroxyl value) and a relatively high content of unsaturated impurities (total unsaturated). Aldehyde condensed resin particles are poor in dispersibility, and when used as a raw material such as the above sealing material, not only high flame retardancy cannot be imparted, but also high flexibility, high elongation and The provision of high mechanical strength is also insufficient.

[0007]

Means for Solving the Problems The present inventor has made intensive studies to solve the above-mentioned problems, and has obtained the following new findings. That is, by using aldehyde condensed resin fine particles as a dispersoid and employing a polyether polyol having a small total unsaturation as a dispersion medium, a cured product having high flexibility, high elongation and high flame retardancy is obtained. It has been found that the non-foamed urethane-based curable composition can be used as a sealing material, a waterproofing material, an adhesive and the like. It has also been found that, in the case of a polyether polyol having a relatively large hydroxyl value, it is particularly important to employ one having a small total unsaturation.

[0008] Thus, the present invention is characterized by containing a urethane prepolymer aldehyde condensation resin fine particles in the following hydroxyl group-containing polyether obtained from fine particle dispersion and organic isocyanates comprising been dispersed as essential components Provide a non-foamed urethane-based curable composition
You. Water acid group-containing polyether: hydroxyl value X is 5~70m
gKOH / g and the total degree of unsaturation Y is 0.07 meq
A / g Der Ru polyether or less, and, X is 32
to polyether X, Y was fully <br/> below following formula (1) at least mg KOH / g. Y ≦ 0.9 / (X−10) (1)

In the present invention, it is important to use a hydroxyl group-containing polyether having at least one specific hydroxyl group as a dispersion medium of the fine particle dispersion. Certain water-acid-group-containing polyethers can be obtained by using diethyl zinc, iron chloride, metal porphyrin, such as double metal cyanide complex in the catalyst. In the case of an ordinary alkali catalyst such as KOH, the degree of unsaturation increases particularly in a high molecular weight compound, which is not appropriate. Preferably, a double metal cyanide complex catalyst is used.

The use of double metal cyanide complexes, such as cobalt zinc cyanide-glyme, as catalysts for producing polyoxyalkylene polyols is known. Such double metal cyanide complex catalysts are described in, for example, EP 283148, US Pat.
It is described in specifications such as US Pat. No. 3,278,458 and US Pat. No. 3,278,459.

[0011] The particular water-acid-group-containing polyethers in the present invention, the presence of such a composite metal cyanide complex catalysts as described above, those prepared by reacting an alkylene oxide to 1 or more functional initiator preferable. The alkylene oxide to be reacted with the initiator includes ethylene oxide, propylene oxide, 1,2-
Butylene oxide, and 2,3-butylene oxide is not better good <br/>.

[0012] Examples of the initiator, monohydrochloride
Alkoxy compounds, polyhydroxy compounds, monoamine compounds
Products, polyamine compounds, and low molecular weight polyoxyalkylene mono- or polyols obtained by reacting them with a relatively small amount of alkylene oxide. Preferably, monohydric alcohol, polyhydric alcohol, monohydric phenol
Le, a polyhydric phenol, a monoamine, a polyamine, and a low molecular weight polyoxyalkylene polyol obtained these is reacted with a relatively small amount of alkylene oxide. Incidentally, low molecular weight polyoxyalkylene mono- or polyol as initiator, of low molecular weight is employed than the specific hydroxyl <br/> group-containing polyether.

Specific examples of the above initiator include methanol, ethanol, propanol, butanol, ethylene glycol, dipropylene glycol, butanediol, glycerin, trimethylolpropane, pentaerythritol, dextrose, bisphenol A,
Examples include bisphenol S and polyoxypropylene polyol obtained by reacting these with propylene oxide. These initiators may be for 併of two or more thereof.

[0014] Particular water-acid-group-containing polyethers in the present invention has a hydroxyl value X is 5~70mgKOH / g and a total unsaturation degree Y is Ru der less 0.07 meq / g
A polyether, and, X is 32 mgKOH / g
Polyether that meet the X, Y previous following formula (1) when the above
Using

[0015] The particular water-acid-group-containing polyether is usually an average hydroxyl number of 1.5 or higher have better good. Preferably, the hydroxyl value X is 5 to 60 mgKOH / g,
Particularly, the hydroxyl value X is preferably from 5 to 45 mgKOH / g. Further, the total degree of unsaturation Y is preferably 0.04 meq / g or less.

The fine particle dispersion according to the present invention is characterized in that
Of water acid group-containing polyether as a dispersion medium, a dispersion of a dispersoid of aldehydes condensation resin particles. The fine particle dispersion is not particularly limited, well-known or may be prepared by such known means. For example,
No. 14,708 discloses a method for producing a dispersion of aldehyde condensation resin fine particles by condensing a substance capable of forming an aldehyde condensation resin in a dispersion medium. JP-A-51-122193 describes a method of forming sedimentable particles of an aldehyde condensation resin and blending the same with a dispersion medium. Further, JP-B 63-4851, JP-Sho 63-4852, JP-like also Japanese Patent Publication 63-33768, JP-dispersion similar aldehyde condensation resin particles are described.

In the present invention, it can be the specific water-acid-group-containing polyether as a dispersion medium, to produce a fine particle dispersion of the present invention by a method described, for example, in the above publication. In addition, the fine powder of the aldehyde condensation resin is
It can also be prepared by adding to water the acid group-containing polyether. Such a fine powder can be obtained by a method of pulverizing an aldehyde condensation-based resin or a method of performing condensation of a substance capable of forming an aldehyde condensation-based resin in a dispersion medium other than the specific dispersion medium to precipitate fine particles. .

[0018] Preferred method for manufacturing a fine particle dispersion of the present invention, first, the specific water-acid-group-containing polyether as a dispersion medium, the condensation of an aldehyde condensation resin forming substance in the dispersion medium The second method is to deposit fine particles by performing condensation of a substance capable of forming an aldehyde condensation resin in a dispersion medium other than the above specific dispersion medium. The above specific
How to replace the like with water acid group-containing polyether. According to these two methods, the generated fine particles have a small particle diameter and are unlikely to settle in a specific dispersion medium, so that a fine particle dispersion having high dispersion stability can be produced.

One of the raw materials for forming the aldehyde condensation resin in the present invention is an aldehyde. As the aldehydes, aliphatic, alicyclic, aromatic, heterocyclic aldehyde compounds and other aldehydes can be exemplified in a wide range . Derivatives of these condensates and compounds capable of generating aldehydes may also be used.
These aldehydes alone can be used, or cut with a two or more <br/>併. Preferred aldehydes are lower aliphatic aldehydes, particularly preferably aliphatic aldehydes having 4 or less carbon atoms and derivatives thereof. Specifically, there are formaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, isobutyraldehyde, paraformaldehyde, paraacetaldehyde, etc., and preferably formaldehyde. These aldehydes can be used by dissolving in a solvent, particularly preferred solvent is water, Lena had limited thereto. In the present invention, it is particularly preferable to use an aqueous solution of formaldehyde, that is, formalin.

Other raw materials for forming the aldehyde condensation resin are as follows:
A compound capable of forming a solid aldehyde condensation-type resin by condensation with the aldehyde as described above (hereinafter, referred to as an aldehyde condensation compound), and the aldehyde condensation compound is capable of reacting with an aldehyde (hereinafter, referred to as an aldehyde condensation compound). Basically two reaction sites). The reaction site is a carbon atom to which a hydrogen atom in an aromatic nucleus of an aromatic compound is bonded, or a hydrogen atom in an amino group or an amide group.
A nitrogen atom to which an atom is bonded is typical. As the reactive site in the aromatic compound, an ortho- or para-position of an aromatic nucleus to which a hydroxyl group or an amino group is bonded is preferable, that is, one having no substituent at two or more of such ortho- or para-positions. Appropriate. As the compound having an amino group or an amide group, a polyamine compound having two or more of those groups is basically suitable. Therefore, the aldehyde condensable compounds, phenols, aromatic compounds such as aromatic amines, or
Other urea, melamine, guanidine compounds and other polyamine compounds are preferred. These aldehyde condensable compounds can be used in combination of two or more kinds, and a compound having only one reaction site can be used together with them.

Examples of the phenols among the aromatic aldehyde condensable compounds include phenol, cresol, xylenol, p-alkylphenol, p-alkylphenol and phenol.
-Phenylphenol, bisphenol A, resorcin and the like, and phenol is particularly preferable. Examples of the aromatic amines include aniline, diaminobenzene, p-alkylaniline, N-substituted alkylaniline, diphenylamine, diaminodiphenylmethane, and aniline is particularly preferable. The amino group and the amide group in the aromatic amines themselves are also reaction sites, and therefore, one of the following polyamine compounds:
You may be able to be regarded as a species, these amino groups or
Other reaction sites other than the amide group may be one. The aromatic aldehyde condensable compound is not limited to the above phenols and aromatic amines,
For example, aromatic hydrocarbons such as benzene and xylene and other aromatic compounds can be used. of course,
Phenols and aromatic amines can be used in combination, or at least one of them and another aromatic compound can be used in combination.

[0022] As the aldehyde condensable compounds of the polyamine compound-based, a compound essentially having two or more amino groups or amido groups, have preferred compounds having inter alia two amino groups. For example, sym -triazine having two or more amino groups represented by ureas such as urea, thiourea and N-substituted urea, melamine compounds such as melamine and N-alkyl-substituted melamine, and guanamine compounds such as benzoguanamine and acetoguanamine. s, guanidine, guanidine hydrochloride, aminoguanidine hydrochloride, have preferred guanidine such as dicyandiamide. Of these, particularly preferred are urea, melamine and benzoguanamine. These polyamine compounds, a combination of two or more compounds, such as urea - thiourea, urea - melamine, urea - benzoguanamine, urea - by a tree in in also used in combination, such as dicyandiamide <br/> - melamine - benzoguanamine, melamine .

The above-mentioned polyamine compound and the above-mentioned aromatic compound can be used in combination.
Phenol-urea, phenol-melamine, aniline-
Melamine, aniline-urea, phenol-aniline-melamine, phenol-urea-melamine and other combinations can be exemplified.

Further, as the aldehyde condensable compound,
In addition to the above, known ketone compounds may be used as a raw material of the ketone resin. The compound having at least two reaction sites described above is a compound having only one reaction site.
Or itself is not an aldehyde condensable compounds can be used in combination compounds having two or more active reactive sites, e.g., dialkanolamines, monoalkanolamine, and aliphatic amines.

Further, an initial condensate of an aldehyde condensable compound and an aldehyde, for example, dimethylol urea, hexamethylol melamine, hexamethoxymethyl melamine, etc. can be used as a raw material for forming an aldehyde condensed resin.

The ratio of the aldehyde-condensable compound and the aldehyde in the reaction for producing the aldehyde-condensed resin particles is not particularly limited as long as the ratio theoretically includes the ratio at which the aldehyde-condensed resin is formed . This is because even if unreacted aldehyde condensable compounds remain, they may be contained in the fine particle dispersion as long as the amount is not excessive, and unreacted aldehydes can be removed at the time of replacement of the dispersion medium. . Preferably, 5 to 500 aldehydes are added to 100 parts by weight of the aldehyde condensable compound.
It can be selected from the range of about 10 parts by weight, especially about 10 to 100 parts by weight.

The aldehyde condensed resin produced by the above reaction is considered to be similar or the same as a cured product of a conventionally known condensed thermosetting resin such as phenol resin, urea resin and melamine resin. It is considered that the formation reaction is the same. For example, when formaldehyde is used as the aldehyde, the aldehyde condensable compound and formaldehyde are subjected to addition condensation in the initial stage of the reaction to produce various methylol group-containing compounds. Thereafter, the methylol group-containing compound is dehydrated and condensed, so that the methylol group becomes a methylene group, which is condensed and three-dimensionally cross-linked to form an aldehyde condensation resin insoluble and insoluble in a solvent. .

The particle size of the fully crosslinked aldehyde condensation resin fine particle <br/> child is preferably in the range of 0.01～5Myu m,
Particularly preferably in the range of 0.1~2μ m. If the particle size is too large, it tends to settle in the dispersion medium.
It is preferable that the aldehyde condensed resin fine particles do not substantially settle for at least one month, preferably two months or more when left still. Aldehyde condensation resin microparticle dispersion in the invention is preferably an aldehyde condensation resin particles of particle size 0.01～5Myu m,
It is a white or colored translucent or opaque viscous liquid dispersed in the above specific dispersion medium. The viscosity of the fine particle dispersion, the viscosity of the dispersion medium used, distributed, etc. by which varies the kind and amount of aldehyde condensation resin in the medium, usually suitably the following viscosity 50000C P at 25 ° C. is there. Even those having higher viscosities may be usable by means such as dilution with various polyols.

The fine particle dispersion containing the aldehyde condensed resin fine particles as described above improves the flame retardancy of the non-foamed urethane-based curable composition of the present invention. In particular, phenolic compounds, urea compounds, melamine compounds, guanamine compounds, or microparticle dispersion comprising an aldehyde condensation resin fine particles mainly using guanidine-based compound,
It is particularly effective for improving the flame retardancy of the non-foamed urethane-based curable composition.

The amount of aldehyde condensation resin microparticles in the microparticle dispersion of the present invention, particularly LIMITED Lena Iga, including when using a diluent described later, a low concentration of about 2% by weight may be employed It is. If the concentration is too high, not only its preparation is difficult, but also the dispersion stability is affected, and if the concentration is too low, the effect of improving the flame retardancy is weakened. It can be selected from the range of weight%. Preferably about 5 to 50% by weight, especially 10 to 10%
It can be selected from a range of about 40% by weight.

The invention microparticle dispersion in, when used as a raw material for the production of the urethane prepolymer to be described later, Ru can also be diluted with an appropriate diluent. The diluent is not particularly limited, and may be a conventionally known or well-known polyether monol or polyol. Preferably, the above-mentioned Japanese described as partial dispersion medium
Constant hydroxyl group-containing polyether can be used as diluent
You. That is, it is particularly preferable to use the following hydroxyl group-containing polyether as a diluent. Hydroxyl-containing polyether
And the hydroxyl value X is 5 to 70 mgKOH / g and the total
Polyether having an unsaturation degree Y of 0.07 meq / g or less
And X is 32 mgKOH / g or more
A polyether wherein X and Y satisfy the above formula (1).

[0032] For even water acid group-containing polyether as the preferred diluent, as in the case of the above-mentioned dispersion medium, usually an average hydroxyl number of 1.5 or higher favorable preferable.
The hydroxyl value X is preferably from 5 to 60 mgKOH / g, and particularly preferably the hydroxyl value X is from 5 to 45 mgKOH / g. The total degree of unsaturation Y is 0.04 meq
/ G or less. Such diluents are
It has a high molecular weight and has lower reactivity than a low molecular weight compound as a curing agent component described later. Therefore, it has a hydroxyl group, the storage stability of the blended composition is not a problem. At the time of the curing reaction of the curable composition by the curing agent component, it is considered that the diluent reacts more slowly than the curing agent component.

In the present invention, a urethane prepolymer obtained from a specific aldehyde condensation resin fine particle dispersion and an organic isocyanate is an essential component . Or dilution
Dispersion of specific aldehyde condensation resin fine particles diluted with dispersant
Urethane Prepo Obtained from Body and Organic Isocyanate
Rimmer is an essential component. The urethane prepolymer is:
It can be obtained by reacting the above-mentioned specific fine particle dispersion or the diluted specific fine particle dispersion with various organic polyisocyanates under an isocyanate group excess condition.

The amount of the organic polyisocyanate used may be such that unreacted substances remain, and if the amount of unreacted substances is too large, the unreacted isocyanate compound can be removed after the completion of the reaction. The isocyanate group content of the obtained isocyanate group-containing urethane prepolymer is preferably about 0.1 to 5% by weight.

[0035] As the organic polyisocyanate is an aromatic system having two or more isocyanate groups, alicyclic and <br/> aliphatic polyisocyanate, a mixture of two kinds or more, as well as modified them give There are modified polyisocyanates to be obtained.

Specifically, for example, tolylene diisocyanate (TDI), diphenylmethane diisocyanate (MDI), polymethylene polyphenyl isocyanate (commonly called crude MDI), xylylene diisocyanate (XDI), isophorone diisocyanate (IPD)
I), polyisocyanates such as hexamethylene diisocyanate (HDI) and modified prepolymers thereof,
Nurate modified products, urea modified products, carbodiimide modified products and the like can be mentioned.

The non-foamed urethane-based curable composition of the present invention comprises a water-curable one-part curable composition composed of the urethane prepolymer alone, and a polyether polyol or the like as a curing agent component. It can be divided into two-part curable compositions.

In the curing reaction of the urethane prepolymer, a curing acceleration catalyst may or may not be used. Examples of the curing accelerating catalyst include alkyl titanates, organosilicon titanates, metal salts of carboxylic acids such as tin 2-ethylhexanoate and dibutyltin dilaurate, and dibutylamine.
2-ethylhexyl Sano amine salts such as benzoate and the like may be employed other acidic catalysts and basic catalysts. Also,
If a stabilizer and a deterioration inhibitor are used in combination, more excellent weather resistance and heat resistance can be imparted.

[0039] non-foamed urethane curable composition of the present invention, If necessary, fillers, reinforcement agents, pigments, may be included such as anti-sagging agents. Also as the above curing agent component
Polyether polyols, chain extenders, crosslinking agents, etc.
You may not.

As a reinforcing agent, carbon black, fine powdered silica, etc., as a filler, calcium carbonate, talc, clay, silica, etc., as a plasticizer, dioctyl phthalate, dibutyl phthalate, dioctyl adipate, chlorinated paraffin , petroleum-based such as a plasticizer, and a pigment
Iron oxide Te, chromium oxide, inorganic pigments and phthalocyanine blue and titanium oxide, organic pigments such as phthalocyanine green, organic acid-treated calcium carbonate as anti-sagging agent, hydrogenated castor oil, aluminum stearate,
Examples include calcium stearate, zinc stearate, and finely divided silica. Examples of the chain extender include ethylene glycol and 1,4-butanediol, and examples of the cross-linking agent include polyfunctional alcohols and polyamines.

The non-foamed urethane-based curable composition of the present invention can be used as a one-pack or two-pack sealing material, waterproof material, or structural adhesive. In particular, it is suitable for applications requiring the adhesiveness of the cured product itself, sufficient strength, and flame retardancy.

[0042]

EXAMPLES Hereinafter is a description of the present invention embodiment, the present invention is Lena have limited only to these examples.

A non-foamed urethane-based curable composition of the present invention was produced using the following polyols and a fine particle dispersion containing them as a dispersion medium, and the performance of a cured product from the curable composition was evaluated.

Polyol A: molecular weight 7000 obtained by adding propylene oxide to glycerin, hydroxyl value 24 mg KO
H / g, a polyether triol of total unsaturation degree 0.1 meq / g (viscosity at 25 ° C. The 1500c P). Polyol B: a polyether triol having a molecular weight of 10,000 obtained by adding propylene oxide to glycerin, a hydroxyl value of 17 mg KOH / g, and a total degree of unsaturation of 0.033 meq / g (25
Viscosity 3000c P at ° C.).

Fine particle dispersion C: 100 parts by weight of melamine, 130 parts by weight of a 35% formalin aqueous solution, and 400 parts by weight of polyol A are charged into a reactor, and stirred and reacted at 80 ° C. for 2 hours, and further at 100 ° C. for 3 hours. after reaction, to the inside pressure of the system was reduced remove water and unreacted formaldehyde <br/>. To obtain a white viscous melamine resin dispersion. Viscosity at 25 ° C. of the dispersion C was Tsu der 4000c P. Microparticle dispersion D: except using Polyol B instead of polyol A in the fine particle dispersion C above in the same manner to give a white viscous melamine resin dispersion. Dispersion D
The viscosity at 25 ℃ of Tsu Der 10000c P.

Comparative Example 1 A reactor was charged with 100 parts by weight of the fine particle dispersion C and 9.0 parts by weight of diphenylmethane diisocyanate.
For 8 hours to obtain a polyurethane prepolymer.
The isocyanate group content was 1.41% by weight. With respect to 100 parts by weight of the urethane prepolymer, 50 parts by weight of dioctyl phthalate, 50 parts by weight of fatty acid-treated calcium carbonate (trade name: Shirahika CCR, manufactured by Shiraishi Industry Co., Ltd.), and 10 parts by weight of titanium oxide were added. The mixture was uniformly mixed with a kneader to obtain a homogeneous polyurethane-based curable composition. The composition was moisture-cured to obtain a fully cured sheet having a thickness of 2 mm, and the mechanical properties (rupture strength, elongation at break, 100% modulus) and oxygen index of the sheet were examined. The oxygen index is according to ASTM E84. The results are shown in Table 1 below. Hereinafter referred to as the 100% modulus and M _100.

(Example 1 ) The fine particle dispersion C in Comparative Example 1 was changed to the fine particle dispersion D, and the amount of diphenylmethane diisocyanate used was 7.
Polyurethane prepolymer (isocyanate group content is 1.41% by weight) in the same manner except that the amount is changed to 7 parts by weight.
A fully cured sheet was obtained, and the mechanical properties (rupture strength, elongation at break, M ₁₀₀ ) and oxygen index of the sheet were examined. The results are shown in Table 1 below.

(Comparative Example 2 ) The fine particle dispersion C in Comparative Example 1 was changed to polyol A, and the amount of diphenylmethane diisocyanate used was 1
A polyurethane prepolymer (isocyanate group content: 1.43% by weight) and a fully cured sheet were obtained in the same manner except that the amount was changed to 0.1 part by weight, and the mechanical properties (breaking strength, breaking elongation, M ₁₀₀ ) and oxygen index. The results are shown in Table 1 below.

(Comparative Example 3 ) The fine particle dispersion C in Comparative Example 1 was changed to a polyol B, and the amount of diphenylmethane diisocyanate used was changed to 8.
A polyurethane prepolymer (isocyanate group content: 1.42% by weight) and a fully cured sheet were obtained in the same manner except that the amount was changed to 50 parts by weight, and the mechanical properties (breaking strength, breaking elongation, M ₁₀₀ ) of the sheet were obtained. And oxygen index. The results are shown in Table 1 below.

[0050]

[Table 1]

[0051]

The non-foamed urethane-based curable composition of the present invention cures at room temperature to give a cured product having high flexibility, high elongation and high flame retardancy. Therefore, in applications such as high-performance sealing materials, structural adhesives, waterproofing materials,
That obtained exhibits the above excellent physical properties.

Continuation of front page (56) References JP-A-3-72520 (JP, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) C08G 18/00-18/87

Claims (5)

(57) [Claims] Characterized in that it contains a 1. A urethane prepolymer aldehyde condensation resin fine particles in the lower Kisui acid group-containing polyether is obtained from a fine particle dispersion and organic isocyanates comprising been dispersed as essential components Non-foamed urethane-based curable composition. Water acid group-containing polyether:
A hydroxyl value X is 5~70mgKOH / g and a total unsaturation degree Y is 0.07 meq / g or less der Ru polyether
There are, and, when X is not less than 32 mgKOH / g
X, Y is a polyether that meet the lower following formula (1). Y ≦ 0.9 / (X−10) (1) Wherein said urethane prepolymer is a non-foamed urethane curable composition according to claim 1 is obtained from a diluted the fine particle dispersion and organic isocyanates with a diluent. Wherein the upper KiNozomi interpretation agents, non-foamed urethane-forming curable composition according to claim 2 which is below hydroxyl group-containing polyether. Hydroxyl-containing polyether: hydroxyl value X is 5 to 70 m
gKOH / g and the total degree of unsaturation Y is 0.07 meq
/ G or less, and X is 32
When mgKOH / g or more, X and Y satisfy the above expression (1).
Addition polyether. 4. A further, serial to claim 1, 2 or 3 polyether polyol, which are formulated as a curing agent component
Unfoamed urethane curable composition of the mounting. 5. An aldehyde condensation resin obtained by condensing at least one member selected from the group consisting of a phenol compound, a urea compound, a melamine compound and a guanidine compound with an aldehyde. The non-foamed urethane-based curable composition according to claim 1 , 2, 3 or 4 .