JPH04292683A - Moisture-curing type sealant - Google Patents

Abstract

PURPOSE:To obtain a urethane asphalt-based moisture-curing sealant having excellent alkaline water resistance, sound insulating and absorbing properties and vibration-damping characteristics. CONSTITUTION:A urethane asphalt-based moisture-curing sealant comprising (A) the following emulsified dispersion and (B) an organic polyisocyanate such as diphenylmethane diisocyanate. (A) The dispersion is obtained by emulsifying (a) an organic compound containing 2-8 active hydrogens such as a polyoxypropylene triol (molecular weight=5,000) and a polyoxypropylene diol (molecular weight=2,000) and (b) straight asphalt with a nonionic surfactant.

Description

[Detailed description of the invention]

0001

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a moisture-curing sealant made of a urethane-asphalt prepolymer.

0002

BACKGROUND OF THE INVENTION Moisture-curing sealants, which are popular in the fields of architecture and civil engineering, are one-component and therefore easy to apply and useful. Conventionally, as a moisture-curable sealant, a sealant made by kneading calcium carbonate into a urethane prepolymer having isocyanate groups, which is made of polyoxypropylene polyol and diisocyanate, is known.

0003

[Problems to be Solved by the Invention] However, conventional moisture-curing sealants have had the problem of insufficient alkaline water resistance and sound-insulating/vibration-proofing properties.

0004

[Means for Solving the Problems] The present inventors have made intensive studies aimed at obtaining a urethane/asphalt-based moisture-curing sealant that has excellent alkaline water resistance, sound insulation, and vibration insulation properties, and as a result, has developed the present invention. Reached. That is, the present invention provides an emulsified dispersion (A) consisting of an organic compound (a) having 2 to 8 active hydrogen atoms and asphalt (b), and an organic polyisocyanate compound (B). A moisture-curing sealant characterized by comprising an asphalt-based prepolymer [1], and
A dispersion (A) in which an organic compound (a) having 2 to 8 active hydrogen atoms and asphalt (b) are emulsified using a surfactant.
) and the organic polyisocyanate compound (B), (A
A method for producing a urethane-asphalt prepolymer [1] having an isocyanate group, characterized in that the active hydrogen equivalent of (B) is reacted with the isocyanate group equivalent of (B) in a ratio of 1:1.2 to 2.5. It is.

In the present invention, the organic compound (a) having 2 to 8 active hydrogens includes, for example, (a) polyhydric alcohols, (b) low-molecular polyamines, (c) polyoxyalkylene polyols, Examples include organic compounds selected from the group consisting of (d) polyoxyalkylene polyamines, (e) polyolefin polyols, and (f) polymer polyols, and which usually have 2 to 8 active hydrogen atoms, preferably 2 to 5 active hydrogen atoms.

Examples of polyhydric alcohols (a) include aliphatic dihydric alcohols (ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, 1,4-butanediol, neopentyl glycol, 1,6-hexanediol, 1,8-octamethylene diol, methyldiethanolamine, etc.), low molecular weight diols with cyclic groups [1,4-bis(hydroxymethyl)cyclohexane, m- and p-xylylene glycol, 1,4-bis(2- hydroxyethoxy)benzene, 1,4-bis(α-hydroxyisopropyl)
benzene, 2,2-bis(4-hydroxyethoxyphenyl)propane, etc.), trihydric alcohols (glycerin, trimethylolpropane, hexanetriol, etc.)
, 4- to 8-hydric polyhydric alcohols (sorbitol, shu-
closed etc.).

[0007] As the low molecular weight polyamines (b), C2
~C6 alkylene diamine (ethylene diamine, tetramethylene diamine, hexamethylene diamine, etc.); polyalkylene (per alkylene group, C2 to C6) polyamine [diethylene triamine, iminobispropylamine, bis(hexamethylene) triamine, triethylene tetramine, tetraethylenepentamine, pentaethylenehexamine, etc.]; these alkyls (C1-C
4) or hydroxyalkyl (C2-C4) substituted product [
dialkyl (C1-C3) aminopropylamine, aminoethylethanolamine, methyliminobispropylamine, etc.]; alicyclic or heterocyclic polyamines (C
4-C15) [N-aminoethylpiperazine, 1,3-
diaminocyclohexane, isophorone diamine, hydrogenated methylene dianiline, etc.]; Aliphatic polyamines having an aromatic ring (C8 to C15) [xylylene diamine, tetrachlor-p-xylylene diamine, etc.]; Aromatic polyamines (C6 to C20) ) [phenylenediamine, toluenediamine, methylenedianiline, diaminodiphenylsulfone, benzidine, o-tolidine, thiodianiline, dianisidine, methylenebis(o-chloroaniline)
, bis(3,4-diaminophenyl)sulfone, 4-chloro-o-phenylenediamine, 4-methoxy-6-methyl-m-phenylenediamine, m-aminobenzylamine, 4,4'-diamino-3,3 '-dimethyldiphenylmethane, etc.].

As the polyoxyalkylene polyol (c), active hydrogen-containing compounds [polyhydric alcohols (those exemplified above), low-molecular amines (low-molecular polyamines exemplified above, n-butylamine, stearyl low molecular weight monoamines such as amines), phenols (hydroquinone, bisphenol A, etc.), phosphoric acid, etc.],
Addition of alkylene oxide (alkylene oxide having 2 to 4 carbon atoms, such as ethylene oxide, propylene oxide, butylene oxide, and combinations thereof) (if used in combination, block or random addition may be used); and ethylene oxide, propylene oxide, Examples include ring-opening polymers of alkylene oxides such as tetrahydrofuran. Specific examples of polyoxyalkylene polyol (c) include polyoxyethylene glycol, polyoxypropylene glycol, polyoxypropylene triol, polyoxyethylene polyoxypropylene glycol, polyoxyethylene polyoxypropylene triol, polyoxypropylene tetraol, Examples include polyoxytetramethylene ether glycol.

Examples of the polyoxyalkylene polyamine (d) include polyoxypropylene diamine, polyoxyethylene diamine, polyoxyethylene polyoxypropylene diamine, and polyoxypropylene triamine.

Examples of the polyolefin polyol (e) include polybutadiene polyol and hydrogenated polybutadiene polyol.

The polymer polyol (f) may be a polymer polyol obtained by polymerizing an ethylenically unsaturated monomer in (c) exemplified above or a polymer of this ethylenically unsaturated monomer. Examples include graft polymers with the above (c).

As the ethylenically unsaturated monomer, α
-Olefins (hexene, octene, decene, dodecene, tetradecene, hexadecene, octadecene, icosene, heneicosene, docosene, tricosene, tetracosene, pentacocene, hexacosene, etc.), aromatic hydrocarbon monomers (styrene, α-methylstyrene, etc.)
, unsaturated nitriles [(meth)acrylonitrile, etc.]
, (meth)acrylic acid esters {(meth)acrylic acid alkyl ester (alkyl group has 1 to 30 carbon atoms) [
Methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, nonyl (meth)acrylate, decyl (meth)acrylate, undecyl (meth)acrylate, dodecyl (meth)acrylate, tridecyl (meth)acrylate, tetradecyl ( meth)acrylate, pentadecyl(meth)acrylate, hexadecyl(meth)acrylate, octadecyl(
(meth)acrylate, eicosyl (meth)acrylate, docosyl (meth)acrylate, etc.], (meth)acrylic acid hydroxyalkyl ester [hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, etc.]}, ethylenically unsaturated carboxylic acid and its derivatives [(meth)acrylic acid, (meth)acrylamide, etc.], aliphatic hydrocarbon monomers (ethylene, propylene, etc.), fluorine-containing vinyl monomers [perfluorooctylethyl (meth)acrylate, etc.], nitrogen Contains vinyl monomers (diaminoethyl methacrylate, morpholinoethyl methacrylate, etc.), glycidyl (meth)
Examples include acrylate, vinyl-terminated silicone (such as a compound represented by the following chemical formula 1), and the like.

[0013]

[Chemical formula 1]

The content of the ethylenically unsaturated monomer constituting the polymer polyol (f) is usually 0.1 to 90% by weight, preferably 5.0 to 80% by weight.

As a method for producing the polymer polyol (f), for example, a method of polymerizing an ethylenically unsaturated monomer in (c) in the presence of a polymerization initiator (radical generator, etc.) (US Patent No. Specification No. 3383351, Special Publication No. 39-2
No. 4737, Japanese Patent Publication No. 47-47999, Japanese Patent Publication No. 1977-
15894, etc.) or a method in which (c) is graft-polymerized with a polymer obtained by prepolymerizing an ethylenically unsaturated monomer in the presence of a radical generator. that's all(
What is exemplified as a) may be a mixture of two or more types. Among (a) to (f), preferred are (a), (c), (e), (f), and mixtures of two or more thereof. Particularly preferred are (c), (e), (f), and mixtures of two or more of these. The active hydrogen equivalent of the organic compound (a) is usually 31 to 10,000. Preferably, it is 31 to 8,000.

[0016] As the asphalt (b) in the present invention, straight asphalt, blown asphalt,
Examples include cutback asphalt. Preferably, it is straight asphalt having a penetration degree of 40 to 400 at 25°C. (a) and (b) in the dispersion (A)
) is usually 5:95 to 90:10, preferably 10:90 to 80:20. When (b) is less than 10, the sound-insulating and vibration-proofing properties of the moisture-curing sealant are insufficient, and when it exceeds 95, the tensile strength is insufficient.

In the present invention, the dispersion (A) is usually obtained by emulsifying and dispersing (a) and (b) using a surfactant (1). To exemplify the method for producing dispersion (A), surfactant (1) is dispersed or dissolved in (a) in advance, heated to 200°C, and fed into a rotor line mixer together with (b). (A) is obtained by a continuous production method in which the emulsification and dispersion are carried out at 1,000 to 5,000 rotations. Surfactant (
(A) can also be obtained by dispersing or dissolving in (b) in advance instead of a). It can also be carried out batchwise using a homomixer, high-speed disperser, etc.

The surfactant (1) may be a nonionic surfactant, an anionic surfactant, a cationic surfactant, or an amphoteric surfactant, by emulsifying and dispersing (a) and (b) in a stable manner. It is fine as long as it makes it possible to Individual examples will be given below.

Examples of nonionic surfactants include higher alcohol ethylene oxide adducts (lauryl alcohol ethylene oxide 10 mole adduct, etc.), alkylphenol ethylene oxide adducts (nonylphenol ethylene oxide 6 mole adduct, etc.), and arylalkylphenol ethylene oxide adducts. (styrenated phenol ethylene oxide 5 mol adduct, etc.), fatty acid ethylene oxide adduct (oleic acid ethylene oxide 15 mol adduct, etc.), polyhydric alcohol fatty acid ester ethylene oxide adduct (lauric acid monoglyceride ethylene oxide 10 mol adduct, etc.) ), higher alkylamine ethylene oxide adducts (stearylamine ethylene oxide 20 mole adduct, etc.), polyamine alkylene oxide adduct (ethylenediamine ethylene oxide 15 mole adduct, m-xylylenediamine ethylene oxide 10 mole, propylene oxide 8 mole, ethylene oxide 10 mole block adduct), fatty acid amide ethylene oxide adduct (
(20 mole adduct of oleic acid amide ethylene oxide, etc.), polypropylene glycol ethylene oxide adduct (such as the compound represented by the following chemical formula 2),

[0020]

[Case 2]

Fatty acid esters of glycerol (lauric acid monoglyceride, stearic acid diglyceride, etc.), pentaerythritol fatty acid esters (pentaerythritol monopalmitate, pentaerythritol monostearate, etc.), sorbitol fatty acid esters (
These include sorbitol monopalmitate, etc.), fatty acid esters of sucrose (stearic acid monoester of sucrose, etc.), and fatty acid amides of alkanolamines (lauric acid diethanolamide, lauric acid monoisopropanolamide, etc.).

Examples of anionic surfactants include carboxylate type (sodium laurate, sodium stearate, sodium oleate, etc.), sulfate type [lauryl sulfate sodium salt, cetyl sulfate sodium salt, C12H25 (CH2CH2O)] nSO
3Na, etc.], sulfonate type (sodium dodecylbenzenesulfonate, sulfosuccinic acid di-2-ethylhexyl ester sodium salt, etc.), phosphate type (
lauryl phosphate monoester disodium salt, lauryl phosphate monoester monosodium salt, etc.). Examples of cationic surfactants include amine salt types (triethanolamine monostearate, stearamide ethyl diethylamine, 2-heptadecenylhydroxyethylimidazoline, etc.), quaternary ammonium salt types (lauryl trimethylammonium chloride, lauryl dimethyl benzyl ammonium chloride, cetylpyridinium chloride, stearamidemethylpyridinium chloride, etc.).

Examples of amphoteric surfactants include amino acid type (sodium lauryl aminopropionate, etc.), betaine type (lauryl dimethyl betaine, stearyl dimethyl betaine, lauryl dihydroxyethyl betaine, etc.). The surfactants (1) exemplified above may be a mixture of two or more thereof. Among (1), preferred are nonionic surfactants, cationic surfactants, amphoteric surfactants, and mixtures of two or more of these. The amount of surfactant (1) added is usually 0.05 to 20% by weight, preferably 0.1 to 10% by weight based on (a).
It is.

In the present invention, as the organic polyisocyanate compound (B), for example, (g) carbon number [NCO
Excluding the carbon in the group, the same applies to (chi) to (nu) below] 2 to
12 aliphatic polyisocyanate, (h) carbon number 4-1
5 alicyclic polyisocyanate, (li) carbon number 8-12
Aroaliphatic polyisocyanate, (nu) carbon number 6-2
0 aromatic polyisocyanates, and modified products of these polyisocyanates. Specific examples of (g) to (l) are given below.

Specific examples of the aliphatic polyisocyanate (I) include ethylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate (
HDI), dodecamethylene diisocyanate, 2,2,
Examples include 4-trimethylhexane diisocyanate, lysine diisocyanate, 2,6-diisocyanate methyl caproate, bis(2-isocyanate ethyl) fumarate, and bis(2-isocyanate ethyl) carbonate.

Specific examples of the alicyclic polyisocyanate (H) include isophorone diisocyanate (IPDI),
Dicyclohexylmethane diisocyanate (hydrogenated MDI
), cyclohexylene diisocyanate, methylcyclohexylene diisocyanate (hydrogenated TDI), bis(2
-ethyl isocyanate)4-cyclohexene-1,2
-Dicarboxylate, etc.

Specific examples of the araliphatic polyisocyanate (li) include xylylene diisocyanate, tetramethylxylylene diisocyanate, and bis(2-isocyanateethyl)benzene.

Specific examples of the aromatic polyisocyanate (N) include 1,3- or 1,4-phenylene diisocyanate, 2,4- or 2,6-tolylene diisocyanate (TDI), diphenylmethane-2,4' - or 4,4'-diisocyanate (MDI), naphthylene-1,5-diisocyanate, 3,3'-dimethyldiphenylmethane-4,4'-diisocyanate, o-tolidine diisocyanate, crude TDI, polyphenylmethane polyisocyanate (crude MDI), etc.

Specific examples of the modified polyisocyanate (l) include carbodiimide groups,
Examples include modified products into which uretdione groups, uretoimine groups, urea groups, biuret groups, isocyanurate groups, etc. are introduced. The materials exemplified above as (B) may be a mixture of two or more. Preferred among (g) to (l) are (ch), (li), (n), and modified products in which each group exemplified in (l) is introduced into these.

[0030] In the moisture-curing sealant of the present invention,
The isocyanate group in the urethane-asphalt prepolymer [1] is usually located at the terminal and/or side chain of the prepolymer. The ratio of (A) and (B) constituting [1] is such that the ratio of the active hydrogen equivalent of (A) to the isocyanate group equivalent of (B) is usually 1:1.2 to 2.5, preferably The ratio may be 1:1.3 to 2. If the equivalent ratio of (B) is less than 1.2, the urethane-asphalt prepolymer [1] will have a high viscosity, and if it exceeds 2.5, foaming will occur and the tensile strength will be insufficient. The total weight percent of isocyanate groups in [1] is usually 0.1 to 5%
, preferably 0.2 to 3.5%.

To exemplify the production method [1], (A) and, if necessary, the catalyst (2) are charged into a reaction vessel and mixed, and then (
[1] can be obtained by adding B) and reacting at 30 to 100°C.

As the catalyst (2), metal-based and amine-based catalysts conventionally used in urethanization reactions can be used. As a metal catalyst, dibutyltin dilaurate (D
TD), alkyl titanate, organosilicon titanate, stannath octoate, lead octylate, zinc octylate,
Examples include bismuth octylate, dibutyltin diorthophenyl phenoxide, and reaction products of tin oxide and ester compounds (dioctyl phthalate, etc.). Preferred among these are tin, lead and bismuth catalysts. Examples of amine catalysts include monoamines [such as triethylamine], diamines [N, N, N', N'-
tetramethylethylenediamine, etc.], triamines [
N,N,N',N",N"-pentamethyldiethylenetriamine, etc.], cyclic amines [triethylenediamine, etc.], and the like. As the catalyst, a metal type and an amine type catalyst may be used in combination.

[0033] After the sealant of the present invention is cured, tan
δ is usually 0.3 to 1.2, preferably 0.4 to 1.1 under the conditions of temperature = 20°C and frequency = 100 Hz. If it is less than 0.3, the sound insulation and absorption properties will deteriorate, and if it exceeds 1.2, the elasticity will decrease. The tan δ is measured using a normal solid dynamic viscoelasticity measurement device.

[0034] The moisture-curing sealant of the present invention contains fillers, plasticizers, anti-aging agents, and other components (C).
A thixotropic agent, a thixotropic auxiliary agent, a solvent, etc. may be included. Examples of the filler include fillers (ground calcium carbonate, precipitated calcium carbonate, carbon black, talc, mica, etc.), resins (vinyl chloride, polyethylene, etc.), and the like. Examples of the plasticizer include dioctyl phthalate, dibutyl phthalate, dioctyl adipate, dioctyl sebacate, petroleum resin, and the like. As an anti-aging agent, hindered amine type [4-benzoyloxy-2,2,6,6-tetramethylpiperidine (Sankyo Sanol LS-744)
etc., hindered phenolic [octadecyl-3-(3,5-di-t-butyl-4-hydroxyphenyl)]
Propionate (Irganox 1 manufactured by Ciba Geigy, Japan)
076), etc.], benzophenone series (2-hydroxy
-4-methoxybenzophenone, etc.), benzotriazole series [2-(5-methyl-2-hydroxyphenyl)
benzotriazole, etc.]. Examples of the thixotropic agent include ultrafine powdered silica and hydrogenated castor oil. As a thixotropic agent, D
Examples include MSO (dimethyl sulfoxide) and polyoxyethylene polyoxypropylene polyol. As a solvent, hydrocarbon solvents (toluene, xylene,
Examples include cyclohexane, heptane, etc.), ester solvents (ethyl acetate, butyl acetate, etc.), and ketone solvents (methyl ethyl ketone, methyl isobutyl ketone, etc.).

[0035] As a method of incorporating the other component (C) exemplified above into the sealant of the present invention, it is also possible to use (C) together in the manufacturing process of [1] to form the sealant of the present invention. [1] may be produced and then [1] and (C) may be mixed to form the sealant of the present invention. To further explain the former method, for example, (A) and, if necessary, (C) and catalyst (2) are charged into a planetary mixer, mixed, and then (B) is added and reacted at 30 to 100°C. The sealant of the present invention can be obtained by such methods. If other ingredients (C) are not included, [1]
is the sealant of the present invention.

[0036] Examples of the construction method using the sealant of the present invention include a method of caulking using a cartridge gun or the like after filling a cartridge, or a method of applying with a spatula or the like.

The sealant of the present invention can be used in applications requiring long-term durability, alkaline water resistance, and sound-insulating/vibration-proofing properties, such as: PC-to-sash joints, RC pouring joints, RC induction joints, etc.), rooftops, floors, roofs and walls, etc.; For civil engineering purposes: irrigation channels, access roads, road expansion joints, soundproof wall joints, etc. and weirs, etc.; 1. Automobiles, such as ceilings, floors, engine areas, under car bodies, etc.; 2. Building materials, suitable for sealing floors, wall materials, boards, etc.

[0038]

EXAMPLES The present invention will be further explained below with reference to Examples, but the present invention is not limited thereto. Hereinafter, parts refer to parts by weight, and % refers to % by weight. The meanings of abbreviations in the examples and evaluation test methods are shown below.

(Abbreviation) PP-2000; molecular weight = 2,000, polyoxypropylene diol PP-3000; molecular weight = 3,000, polyoxypropylene diol GP-5000; molecular weight = 5,000, addition of propylene oxide to glycerin Product PL-3000; molecular weight = 3,000, polyoxyethylene polyoxypropylene diol (ethylene oxide% = 50%) DTD; dibutyltin dilaurate MDI; diphenylmethane diisocyanate K-1; nonylphenol ethylene oxide 6 mole adduct K-2; Styrenated phenol ethylene oxide 5 mole adduct

(Evaluation test method) 1) Alkaline water resistance;
It was immersed at 0°C for 4 weeks, and the retention rate (%) of tensile strength at break was determined in accordance with JIS K-6301. (Dumbell shape: No. 2, tensile speed = 500mm/min
)2) Bleeding test: A cured sheet with a thickness of 2 mm is placed on a sheet of paper and left at 50° C. for 24 hours, then the paper is peeled off and contamination is observed. 3) Measuring method of sound insulation/vibration insulation properties; conduct shear viscoelasticity test using a dynamic viscoelasticity tester, sample temperature = 20°C, frequency = 100.
It is carried out under the condition of Hz, and tan δ is measured.

(Production Example) 1. Production of polymer polyol (POP-1) 324 parts of GP-5000, 2 parts of PP-3000 in a 4-necked kolben
76 parts were charged and heated to 100°C, and 210 parts of n-butyl methacrylate, 185 parts of n-butyl acrylate, and 1 part of AIBN (2,2'-azobisisobutyronitrile) were added.
0 parts of the mixture was added dropwise over 1 hour. After that AIBN
5 parts were charged and aged at 100°C for 2 hours to obtain a polymer polyol (POP-1). 2. Production A-1 of emulsified dispersion (A-1 to A-3): 224 parts of GP-5000, PP-2000 in advance
Charge 175 parts and 8 parts of K-2 into a mixing tank and heat at 80°C.
The temperature was raised to 100% to dissolve the mixture. The mixed liquid was fed into a rotor line mixer at a flow rate of 200 g/min, and straight asphalt with a penetration degree of 120 heated to 230°C was fed into a rotor line mixer at a flow rate of 300 g/min.
Emulsifying and dispersing at 000 revolutions/min, the asphalt content is 60
% dispersion (A-1) was obtained. A-2; 138 copies of GP-5000, PP in advance
162 parts of K-3000, 13 parts of K-2, and 6 parts of K-2 were charged into a blending tank, heated to 80°C, and dissolved. The blended liquid was fed into a rotor line mixer at a flow rate of 150 g/min, straight asphalt with a penetration degree of 180 heated to 220°C was fed into a rotor line mixer at a flow rate of 350 g/min, and the rotation speed of the rotor line mixer was 4,000 rpm. Emulsification was carried out to obtain a dispersion (A-2) having an asphalt content of 70%. A-3; 1000 copies of POP-1 in advance, K-1
10 parts and 10 parts of K-2 were charged into a mixing tank, and 80 parts
The temperature was raised to ℃ and dissolved. The mixed liquid was fed into a rotor line mixer at a flow rate of 200 g/min, and straight asphalt with a penetration degree of 180 heated to 200°C was fed into a rotor line mixer at a flow rate of 300 g/min, and the rotation speed of the rotor line mixer was 4.
Emulsifying and dispersing at ,000 revolutions/min, with an asphalt content of 6
A 0% dispersion (A-3) was obtained.

Examples 1 to 3 Emulsified dispersions (A) shown in Table 1 were added to a planetary mixer.
), organic polyisocyanate (B) and catalyst (2) were charged and reacted at 70°C for 3 hours to form the sealant of the present invention.
1> to <3> were obtained. Next, the sealant was coated on a glass plate and left to cure for 7 days at 25° C. and 65% RH to obtain test pieces {1} to {3} with a thickness of 2 mm. Table 1 shows the results of alkaline water resistance, bleed test, and sound insulation/vibration properties test using this test piece.

[0043]

[Table 1]

Examples 4 to 6 Emulsified dispersions (A) shown in Table 2 were added to a planetary mixer.
), organic polyisocyanate (B) and catalyst (2) are charged, and after reacting at 70°C for 3 hours, other components (C) shown in Table 2 are charged and mixed to prepare the sealant <4> of the present invention.
<6> was obtained. Next, the sealant was coated on a glass plate and left to harden for 7 days at 25° C. and 65% RH to obtain test pieces {4} to {6} with a thickness of 2 mm. Table 2 shows the results of alkaline water resistance, bleed test, and sound insulation/vibration properties test using this test piece.

[0045]

[Table 2]

Examples 7 to 9 Emulsified dispersions shown in Table 3 (A
), other components (C) and catalyst (2) are charged and mixed to make them homogeneous, then organic polyisocyanate (B) is charged and reacted at 70°C for 3 hours to form the sealant of the present invention <7
>~<9> were obtained. Next, the sealant was coated on a glass plate and left to cure for 7 days at 25° C. and 65% RH to obtain test pieces {7} to {9} with a thickness of 2 mm. Table 3 shows the results of alkaline water resistance, bleed test, and sound insulation/vibration properties test using this test piece.

[0047]

[Table 3]

Example 10 Emulsified dispersion (A-3) 968 in a planetary mixer
32 parts of MDI and 32 parts of MDI were reacted at 80°C for 10 hours to obtain a urethane-asphalt prepolymer with an isocyanate content of 0.40%. It was a homogeneous liquid with no separation. Comparative Example 1 485 parts of GP-5000, 381 parts of PP-2000, 0.1 part of DTD and 133 parts of MDI were charged into a 4-necked Kolben and reacted at 70°C for 3 hours to obtain a urethane prepolymer. 500 parts of this urethane prepolymer, calcium carbonate
350 parts of DOP, 30 parts of ultrafine powder silica, and 10 parts of PL-3000 were placed in a planetary mixer and mixed at 40°C for 1 hour to obtain a sealant. Next, the sealant is coated on the glass plate, and 2
It was left to stand for 7 days at 5° C. and 65% RH to be cured, and a test piece with a thickness of 2 mm was obtained. Table 4 shows the results of alkaline water resistance and sound insulation/vibration properties tests using this test piece.
Shown below. Comparative Example 2 408 parts of GP-5000, 480 parts of PP-3000, 0.1 part of DTD and 112 parts of MDI were charged into a 4-necked Kolben and reacted at 70°C for 3 hours to obtain a urethane prepolymer. 500 parts of this urethane prepolymer, calcium carbonate
350 parts of DOP, 30 parts of ultrafine powder silica, and 10 parts of PL-3000 were placed in a planetary mixer and mixed at 40°C for 1 hour to obtain a sealant. Next, the sealant is coated on the glass plate, and 2
It was left to stand for 7 days at 5° C. and 65% RH to be cured, and a test piece with a thickness of 2 mm was obtained. Table 4 shows the results of alkaline water resistance and sound insulation/vibration properties tests using this test piece.
Shown below.

[0049]

[Table 4]

[0050]

[Effects of the Invention] The moisture-curing sealant of the present invention has excellent alkaline water resistance, sound-insulating and vibration-proofing properties, and also has excellent bleedability and airtightness. Furthermore, it has excellent movement tracking, mechanical properties, and weather resistance. Because it exhibits the above effects, the moisture-curing sealant of the present invention can be used for applications that require long-term durability and sound-insulating/vibration-proofing properties, such as: Curtain wall PC-to-sash joints, RC pouring joints, RC induction joints, etc.)
Rooftops, floors, roofs, walls, etc.; For civil engineering purposes, such as irrigation canals, roads, road expansion joints, soundproof wall joints and weirs; For automobiles, such as ceilings, floors, engine areas, undersides, etc.; Building materials. As,
Useful for sealing floors, wall materials, boards, etc. Further, the urethane-asphalt prepolymer obtained by the production method of the present invention has excellent emulsion stability and is useful as a base material for sealants, adhesives, waterproof materials, coating materials, etc.

Claims (3)

[Claims] Claim 1: An emulsified dispersion (a) consisting of an organic compound (a) having 2 to 8 active hydrogen atoms and asphalt (b)
A moisture-curing sealant comprising a urethane-asphalt prepolymer [1] having an isocyanate group, which is made of A) and an organic polyisocyanate compound (B). [Claim 2] Tan δ after curing (measurement temperature = 20°C
, frequency=100Hz) is 0.3 to 1.2. 3. A dispersion (A) obtained by emulsifying an organic compound (a) having 2 to 8 active hydrogens and asphalt (b) using a surfactant, and an organic polyisocyanate compound (B), A urethane-asphalt prepolymer [1] having isocyanate groups, characterized in that the active hydrogen equivalent of (A) and the isocyanate group equivalent of (B) are reacted in a ratio of 1:1.2 to 2.5. Production method.