JPH05140532A - Moisture-curing sealant - Google Patents

Abstract

PURPOSE:To obtain the subject sealant having excellent tensile shear strength at an early period of bonding, comprising a specific urethane polymer. CONSTITUTION:The objective sealant comprises a urethane polymer containing 0.2-6wt.% NCO, for example, derived from (A) an organic polyisocyanate (e.g. aliphatic polyisocyanate or alicyclic polyisocyanate), (B) a polyol (e.g. polyhydric alcohol or polyoxyalkylene polyol), (C) an OH-containing thermoplastic resin (one having preferably 40-200 deg.C thermally softening temperature) and (D) a resin (e.g. low-molecular weight xylene resin, low-molecular weight coumarone resin or low molecular weight styrene resin), having >=0.05kg/cm<2> tensile shear strength (five minutes after bonding, at 20 deg.C sealant temperature).

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION This invention relates to moisture curable sealants.

[0002]

2. Description of the Related Art Moisture-curing sealants, which have been widely used in the fields of automobiles, construction, civil engineering, etc., are useful because they are one-part type and have excellent ease of construction. Conventionally, as a moisture-curable sealant, a sealant obtained by kneading calcium carbonate into a urethane prepolymer having an NCO group, which is composed of polyoxypropylene polyol and diisocyanate, has been known.

[0003]

However, the conventional moisture-curable sealant has insufficient tensile shear strength at the initial stage of joining, and its usable applications are limited. In particular, when a conventional sealant is used for the front and rear wind sealing of automobiles manufactured by the direct glazing method, the tensile shear strength at the initial stage of joining is 0.01 Kg / cm ²
There is a problem that the glass slips because there is only one, and there is a demand for a hot-apply sealant that has an initial strength of 0.05 Kg / cm ² or more, which is a tensile shear strength that prevents the glass from slipping even when shock is applied by opening and closing the door. There is.

[0004]

In view of the above situation, the present inventor aims to obtain a moisture-curable sealant having an excellent initial tensile shear strength, which can be expanded and used for the above-mentioned applications. As a result of intensive studies, the present invention has been reached. That is, the present invention is derived from an organic polyisocyanate compound (a), a polyol (b1) and a thermoplastic urethane resin (c) having an OH group, and contains 0.2 to 6% by weight of an NCO group.
Containing the urethane prepolymer (1), the tensile shear strength (after 5 minutes of joining, sealant temperature 20 ° C.) is 0.05.
Moisture curable sealant having a Kg / cm ² or more; together with this urethane prepolymer (1),
Furthermore, a moisture-curable sealant containing a resin (d1) having no active hydrogen and having tackifying property; and an organic polyisocyanate compound (a), a polyol (b)
1), a thermoplastic urethane resin having an OH group (c) and a resin having active hydrogen and having tackifying property (d)
2), containing urethane prepolymer (2) having 0.2 to 6% by weight of NCO group, and having a tensile shear strength (5 minutes after joining, sealant temperature 20 ° C.) of 0.05 Kg
/ Cm ² or more, a moisture-curable sealant.

In the present invention, as the organic polyisocyanate compound (a), for example, (a) carbon number [excluding carbon in NCO group, the same applies to (b) to (d)] 2 to 12 Aliphatic polyisocyanate, (b) alicyclic polyisocyanate having 4 to 15 carbon atoms, (c) aromatic aliphatic polyisocyanate having 8 to 12 carbon atoms, (d) aromatic polyisocyanate having 6 to 20 carbon atoms, and (E) Modified products of these polyisocyanates may be mentioned. The following are specific examples of (a) to (e).

Specific examples of the aliphatic polyisocyanate (a) include ethylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate (HD
I), dodecamethylene diisocyanate, 2,2,4-trimethylhexane diisocyanate, lysine diisocyanate, 2,6-diisocyanate methyl caproate, bis (2-isocyanate ethyl) fumarate, bis (2-isocyanate ethyl) carbonate, etc. Be done.

Specific examples of the alicyclic polyisocyanate (b) include isophorone diisocyanate (IPDI), dicyclohexylmethane diisocyanate (hydrogenated MDI), cyclohexylene diisocyanate, methylcyclohexylene diisocyanate (hydrogenated TDI), bis (2- Isocyanate ethyl) 4-cyclohexene-1,2-dicarboxylate and the like.

Specific examples of the araliphatic polyisocyanate (c) include xylylene diisocyanate, tetramethyl xylylene diisocyanate, bis (2-isocyanatoethyl) benzene and the like.

Specific examples of the aromatic polyisocyanate (d) include 1,3- or 1,4-phenylene diisocyanate,
2,4- or 2,6-toluene diisocyanate (TDI), diphenylmethane-2,4'- or 4,4'-diisocyanate (M
DI), naphthylene-1,5-diisocyanate, 3,3'-dimethyldiphenylmethane-4,4'-diisocyanate, o-tolidine diisocyanate, crude TDI, polyphenylmethane polyisocyanate (crude MDI) and the like.

Specific examples of the modified polyisocyanate (e) include carbodiimide groups, uretdione groups, uretoimine groups, urea groups, buret groups, and (i) to (d) above.
Examples thereof include modified products in which isocyanurate groups are introduced. The materials exemplified above may be a mixture of two or more kinds.
Among (a) to (e), preferred are (b), (c), (d), and modified products obtained by introducing each of the groups exemplified in the item (e) into these.

In the present invention, examples of the polyol (b1) include polyhydric alcohols (f), polyoxyalkylene polyols (to), polyester polyols (h), polyolefin polyols (d), polymer polyols (d), etc. Can be given.

Specific examples of polyhydric alcohols (f) include:
Aliphatic dihydric alcohols (ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, 1,4-butanediol, neopentyl glycol, 1,6-hexanediol, 1,8-octamethylenediol, alkyl dialkanolamine, etc. ) Low molecular weight diols having 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.), and tetrafunctional or higher polyhydric alcohols (sorbitol, sucrose, etc.) and the like.

Examples of the polyoxyalkylene polyol (g) include active hydrogen-containing compounds [polyhydric alcohols (those exemplified above), low-molecular amines (ethylenediamine,
Low molecular weight polyamines such as tetramethylenediamine and hexamethylenediamine, low molecular weight monoamines such as n-butylamine and stearylamine), phenols (hydroquinone, bisphenol A, etc.)] to alkylene oxides (alkylene having 2 to 4 carbon atoms). Oxides such as ethylene oxide, propylene oxide, butylene oxide and combinations thereof) added (if used in combination, may be block or random addition); and ring-opening polymerization products of alkylene oxides such as ethylene oxide, propylene oxide and tetrahydrofuran Can be given. Specific examples of the polyoxyalkylene polyol (g) include polyoxyethylene glycol, polyoxypropylene glycol, polyoxypropylene triol, polyoxyethylene polyoxypropylene glycol, polyoxyethylene polyoxypropylene triol, polyoxypropylene tetraol, Examples thereof include polytetramethylene ether glycol.

Examples of the polyester polyol (h) include condensed polyester polyols obtained by reacting the polyhydric alcohols (f) and / or polyoxyalkylene polyols (to) exemplified above with dicarboxylic acids,
Examples thereof include polylactone polyols obtained by ring-opening polymerization of lactone.

Examples of the dicarboxylic acids constituting the condensed polyester polyol include aliphatic dicarboxylic acids (succinic acid, adipic acid, sebacic acid, glutaric acid, azelaic acid, maleic acid, fumaric acid, etc.) and aromatic dicarboxylic acids (terephthalic acid). Acid, isophthalic acid, etc.), anhydrides of these dicarboxylic acids, lower alkyl (C ₁ -C ₄ ) esters or halides (such as chloride), and mixtures of two or more thereof. As a lactone,
For example, ε-caprolactone can be mentioned.

Specific examples of these polyester polyols (h) include polyethylene adipate, polybutylene adipate, polyhexamethylene adipate, polyneopentyl adipate, polyethylene propylene adipate, polyethylene butylene adipate, polybutylene hexamethylene adipate, polydiethylene adipate. ,
Examples thereof include poly (polytetramethylene ether) adipate, polyethylene azelate, polyethylene sebacate, polybutylene azelate, polybutylene sebacate, polyethylene terephthalate, and polycaprolactone diol.

Specific examples of the polyolefin polyol (i) include polybutadiene polyol and hydrogenated polybutadiene polyol.

As the polymer polyol (nu), there are (g) to (g)
Polymer polyols obtained by polymerizing the ethylenically unsaturated monomer [II] in each of the polyols [I] exemplified in the above section.

Examples of the ethylenically unsaturated monomer [II] include α-olefins (hexene, octene, decene, dodecene, tetradecene, hexadecene, octadecene,
Aikosen, Hen Aikosen, Docosen, Tricosene,
Tetracocene, pentacocene, hexacocene, etc.), aromatic hydrocarbon monomers (styrene, α-methylstyrene, etc.), unsaturated nitriles [(meth) acrylonitrile, etc.], (meth) acrylic acid esters {(meth) acryl Acid alkyl ester (the carbon number of the alkyl group is 1 to 30) [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-containing vinyl monomers (diaminoethylmetha) Relate and morpholinoethyl methacrylate), glycidyl (meth) acrylate -
And so on.

The content of the ethylenically unsaturated monomer [II] constituting the polymer polyol (nu) is usually 0.1 to 90% by weight.
It is preferably 5.0 to 80% by weight. The average number of functional groups of the polymer polyol is usually 2-10. It is preferably 2-8. The active hydrogen equivalent of the polymer polyol is usually 250 to 15,000. Preferably 250-10,000
Is.

The method for producing the polymer polyol (N) is as follows:
For example, a method of polymerizing an ethylenically unsaturated monomer [II] in a polyol [I] in the presence of a polymerization initiator (radical generator, etc.) (US Pat. No. 3,383,351), JP-B-3.
9-24737, JP-B-47-47999, JP-A-50-15894, etc.). Two or more kinds of these (b1) may be used in combination. Among (f) to (nu), the preferred one is
(F), (to) and (nu).

In the present invention, the thermoplastic urethane resin (c) having the OH group has a thermal softening temperature (JIS K220
Those measured at 7) of 40 ° C to 200 ° C are suitable. Preferred as (c) is derived from the above-exemplified organic polyisocyanate compound (a) and diol (b2), and the equivalent ratio of the NCO group of (a) to the OH group of (b2) is 0.5: 1. It was manufactured in the range of 0.98: 1. When the equivalent ratio is less than 0.5: 1, the tensile shear strength is insufficient. If it exceeds 0.98: 1, the viscosity becomes high and the extrudability becomes insufficient. The preferred range of the equivalence ratio is 0.
It is 6: 1 to 0.95: 1.

As (b2), there are (f) to (n) of the above (b1).
Among those exemplified in (2), those having two OH groups.
Two or more kinds of these (b2) may be used in combination. (B
Preferred as 2) are those having two OH groups among those exemplified in the above (f), (to) and (nu).

The manufacturing method of (c) can be carried out by an ordinary method,
A method in which (a), (b2) and optionally the catalyst (3) are charged in a reaction vessel and reacted at a reaction temperature of 60 to 200 ° C;
A method in which (a) and (b2) are poured into a twin-screw extruder and continuously reacted at a reaction temperature of 100 to 220 ° C can be mentioned.

As the catalyst (3), dibutyltin dilaurate (DTD), alkyl titanate, organosilicon titanate, stannas octoate, lead octylate, zinc octylate, bismuth octylate, dibutyltin diorsophenyl. Metal catalysts such as reaction products of phenoxide, tin oxide and ester compounds (dioctyl phthalate, etc.), monoamines [triethylamine, etc.], diamines [N, N, N ', N'-tetramethylethylenediamine, etc.], triamines Examples include amine catalysts such as groups [N, N, N ', N ", N" -pentamethyldiethylenetriamine, etc.], cyclic amines [triethylenediamine, etc.], and the like.
The catalyst may be used alone or in combination with a metal and an amine.

As the resin (d1) having no active hydrogen and having tackifying property, terpene resin; petroleum resin (for example, aliphatic hydrocarbon resin, aromatic hydrocarbon resin, alicyclic carbonization) Hydrogen resin); Low molecular weight xylene resin (for example, reaction product of xylene and formaldehyde, reaction product of mesitylene and formaldehyde that does not have active hydrogen); Low molecular weight coumaron resin (for example, copolymer of coumalone and indene, coumaron) Indene / styrene copolymer); low molecular weight styrene resin (eg, styrene polymer, styrene / ethylenically unsaturated monomer copolymer); rosin-based resin (eg, rosin / glycerin ester), etc. Be done. The molecular weight of (d1) is usually 10,000 or less, preferably 6,000 or less. Preferred as (d1) are low molecular weight xylene resins, low molecular weight coumarone resins and low molecular weight styrene resins.

In the present invention, together with (1), (d1)
The weight ratio of both is usually 100: 1 to
200, preferably 100: 5 to 150.

As the resin (d2) having active hydrogen and having tackifying property, a low molecular weight xylene resin (for example, a reaction product of xylene and formaldehyde, a reaction product of mesitylene and formaldehyde, a reaction product of xylene, phenol and formaldehyde) is used. Low molecular weight coumarone resin (for example, copolymer of coumarone and indene, phenol modified product of coumarone, indene and styrene, etc.); low molecular weight styrene resin (for example, styrene and OH)
Copolymer of ethylenically unsaturated monomer having a group); rosin resin (eg, rosin, hydrogenated rosin, ester of rosin and glycerin); phenolic resin (eg, terpene phenol resin, alkylphenol resin, rosin modified Examples include phenolic resins) having active hydrogen. The molecular weight of (d2) is usually 10,000 or less, preferably 6,000 or less. Preferred as (d2) are low molecular weight xylene resins and / or low molecular weight coumarone resins having active hydrogen.

In the present invention, the weight% of each NCO group in the prepolymer (1) and the prepolymer (2) is usually 0.2 to 6%, preferably 0.3 to 4%.

The prepolymer (1) can be produced by a usual method, and (a), (b1), (c) and, if necessary, the catalyst (3) exemplified above are charged into a reaction vessel, and 60
A method of obtaining (1) by reacting at ~ 140 ° C can be mentioned. The prepolymer (2) can be produced by a usual method, and (a), (b1), (c), (d2) and, if necessary, the catalyst (3) exemplified above are charged into a reaction vessel, and 6
Examples thereof include a method of reacting at 0 to 140 ° C. to obtain (2).

As the sealant of the present invention, the prepolymer (1) is an essential component, and the other components (filler, plasticizer, antioxidant, thixotropic agent, thixotropic agent, catalyst, adhesion imparting agent, etc.) Arbitrarily blended; a prepolymer (1) and a resin (d1) having no active hydrogen and having tackifying property as essential components, and optionally blended with other similar components; and , The prepolymer (2) is an essential component, and other similar components are optionally blended into three types.

As the filler among the other components, fillers (heavy calcium carbonate, precipitated calcium carbonate,
Carbon black, talc, mica, etc.) and the like. Examples of the plasticizer include dioctyl phthalate, dibutyl phthalate, dioctyl adipate, and mineral spirits. Anti-aging agents include hindered amine-based [4-benzoyloxy-2,2,6,6-tetramethylpiperidine (Sankyo LS-744 Sansan Co., Ltd.)], hindered phenol-based [octadecyl-3- (3,5-zzy t Butyl-4
-Hydroxyphenyl) propionate (Nippon Ciba Geigy Irganox 1076, etc.), benzophenone-based (2-hydroxy-4-methoxybenzophenone, etc.), benzotriazole-based [2- (5-methyl-2-hydroxyphenyl) benzotriazole, etc.], etc. Agent. Examples of the thixotropic agent include ultrafine silica powder and hydrogenated castor oil. Examples of the thixotropic agent include dimethyl sulfoxide and polyoxyethylene polyoxypropylene polyol. As the catalyst, those exemplified in the above (3) can be used. Examples of the adhesion-imparting agent include a silane coupling agent [γ-aminopropyltrimethoxysilane, γ-glycidoxypropyltriethoxysilane, a reaction product of these two compounds] and the like.

Exemplifying the method for producing the sealant of the present invention,
A method in which (1), the other components exemplified above, and (d1) as necessary are charged in a planetary mixer and kneaded; (2) and the other components exemplified above are charged in a planetary mixer. The method of kneading and then kneading with three rolls can be used.

Tensile shear strength of the moisture-curable sealant of the present invention at the initial stage of joining (5 minutes after joining, sealant temperature 20
° C.) is usually 0.05 Kg / cm ² or more. The tensile shear strength is based on JIS K6850, and the glass and the glass were joined to each other so that the sealant thickness was 2 mm, and the mixture was allowed to stand in a thermostat at 20 ° C. for 5 minutes, and then the pulling speed was 50.
Value of tensile shear strength measured in mm / min (unit: Kg / cm
² ) Therefore, the moisture-curable sealant of the present invention is a front / rear wind sealing for automobiles manufactured by the direct glazing method that requires tensile shear strength at the initial stage of joining, a joint seal for construction with a large movement, and an end seal for a waterproof sheet. It is suitable for

As a method of applying the moisture-curable sealant of the present invention, a usual method, for example, a cartridge gun, an automatic gun having an extrusion device or the like is set on an adherend, and temperature = normal temperature to 60 ° C., humidity = 10 to 10. Examples thereof include a method of curing at 90% RH.

[0036]

The present invention will be further described with reference to the following examples, but the present invention is not limited thereto. Hereinafter, parts are parts by weight. The following abbreviations in the examples have the following meanings.

(Abbreviated symbol) G-50: Propylene oxide adduct of glycerin (molecular weight = 5,000) G-30; Propylene oxide adduct of glycerin (molecular weight = 3,000) P-30; Propylene oxide adduct of propylene glycol (molecular weight) = 3,000) P-20; propylene oxide adduct of propylene glycol (molecular weight = 2.000) P-10; propylene oxide adduct of propylene glycol (molecular weight = 1,000) DPG; dipropylene glycol BP-3P; propylene oxide addition of bisphenol A Material (molecular weight = 400) TDI; Toluene diisocyanate (2,4-body: 2,6-body =
80/20 weight ratio) MDI; 4,4'-diphenylmethane diisocyanate X-1; xylene resin (addition condensate of metaxylene and formalin, molecular weight = 500, hydroxyl value = 35) X-2; xylene resin (with metaxylene) Addition condensate of formalin, molecular weight = 220, hydroxyl value = 0) K-3; coumarone resin (coumarone / indene / phenol copolymer, molecular weight = 850, hydroxyl value = 30) K-4; coumarone resin (coumarone / indene) -Styrene copolymer, molecular weight = 650, hydroxyl value = 0) DOP; dioctyl phthalate DTD; dibutyltin dilaurate CB; carbon black CA; calcium carbonate

(Evaluation test method) 1) Hardness: Measured with an A type hardness meter according to JIS K6301. 2) Tensile shear strength In accordance with JIS K6850, the glass and the glass were joined together so that the sealant thickness was 2 mm, and left in a constant temperature bath at 20 ° C for 5 minutes, and then the tensile shear strength was set at a tensile speed of 50 mm / min. It was measured. (Unit: Kg / cm ² ) 3) Extrudability According to JIS A5758, the sealant temperature is 60.
Measured by adjusting the temperature to ℃. (Judgment) display ○: Good workability within 15 seconds

(Production Example) Production Example 1; Separable Kolben with P-10 686 parts, DP
92 parts of G and 222 parts of TDI were charged and reacted at 170 ° C. for 60 minutes to obtain a thermoplastic urethane resin (c-1) having a ring and ball type thermal softening point of 75 ° C. Production Example 2; Separa Bull Kolben with 650 parts of P-10 and BP
130 parts of 3P and 219 parts of MDI were charged and reacted at 150 ° C. for 60 minutes to obtain a thermoplastic urethane resin (c-2) having a ring and ball type thermal softening point of 66 ° C.

Examples 1 and 2 Separable Kolben was charged with the organic polyisocyanate compound (a), the polyol (b1) and the thermoplastic urethane resin (c) shown in Table 1 below at the respective compounding amounts shown in Table 1 below. The reaction was carried out at 100 ° C. for 5 hours with stirring to obtain urethane prepolymers [1] and [2] having NCO contents shown in Table 1 below. Urethane prepolymer 500g each
And the other components shown in Table 1 below were placed in a planetary mixer and kneaded to obtain a uniform sealant <1> and <2> of the present invention. The results of testing the tensile shear strength and the like using each sealant are shown in Table 1 below.

Examples 3 and 4 Separable Kolben was charged with the organic polyisocyanate compound (a), the polyol (b1) and the thermoplastic urethane resin (c) shown in Table 2 below at the respective compounding amounts shown in Table 2 below. The reaction was carried out at 100 ° C. for 5 hours with stirring to obtain urethane prepolymers [3] and [4] having NCO contents shown in Table 2 below. Urethane prepolymer 500g each
And the resin (d1) having no active hydrogen and having tackifying property and other components shown in Table 2 below are charged in a planetary mixer and kneaded to make them uniform, and the sealants <3> and <4 > Was obtained. The results of testing the tensile shear strength and the like using each sealant are shown in Table 2 below.

Examples 5 and 6 Separable Kolben has an organic polyisocyanate compound (a), a polyol (b1), a thermoplastic urethane resin (c) and active hydrogen shown in Table 3 below, and has tackifying properties. The resin (d2) contained therein was charged in the respective blending amounts shown in Table 3 below, and reacted at 100 ° C. for 5 hours while stirring, and urethane prepolymers having an NCO content shown in Table 3 below [5]
And [6] were obtained. Urethane prepolymer 500 each
g and the other components shown in Table 3 below were placed in a planetary mixer and kneaded to obtain uniform sealants <5> and <6> of the present invention. The results of testing the tensile shear strength and the like using each sealant are shown in Table 3 below.

[0043]

[Table 1]

[0044]

[Table 2]

[0045]

[Table 3]

Comparative Example 1 Separable Kolben was added to G-50 618 parts, P-20 242.
And 139 parts of MDI were charged and reacted at 100 ° C. for 5 hours with stirring to obtain a urethane prepolymer having an NCO content of 2.1%. 500 g of the urethane prepolymer and the other components shown in Table 4 below were placed in a planetary mixer and kneaded to obtain a sealant. The results of testing the tensile shear strength and the like using this sealant are shown in Table 4 below.

Comparative Example 2 Separable Kolben with G-30 274 parts and P-30 585
Parts and 141 parts of MDI were charged and reacted with stirring at 100 ° C. for 9 hours to obtain a urethane prepolymer having an NCO content of 2.0%. 500 g of the urethane prepolymer and the other components shown in Table 4 below were placed in a planetary mixer and kneaded to obtain a sealant. The results of testing the tensile shear strength and the like using this sealant are shown in Table 4 below.

[0048]

[Table 4]

[0049]

The moisture-curable sealant of the present invention has tensile shear strength at the initial stage of joining which conventional moisture-curable sealants do not have. It also has excellent heat resistance, water resistance, mechanical strength, adhesive strength, and dynamic viscoelasticity. The moisture-curable sealant of the present invention having the above-mentioned effects is particularly useful for front / rear wind sealing of automobiles manufactured by the direct glazing method, which requires tensile shear strength at the initial stage of joining. When using a conventional sealant to the application, although the tensile shear strength is trouble slipping glass because there is only 0.01 kg / cm ² occurs, sealants of the present invention is a tensile shear strength of 0.05 Kg / cm ² or more Therefore, even if an impact such as the opening and closing of the door is applied to the glass, it does not shift and the line trouble does not occur. It is also useful as a joint seal for buildings with large movements and as an end seal for waterproof sheets.

Claims (6)

[Claims] 1. An organic polyisocyanate compound (a),
It contains a urethane prepolymer (1) derived from a polyol (b1) and a thermoplastic urethane resin (c) having OH groups and having 0.2 to 6% by weight of NCO groups, and has a tensile shear strength (after 5 minutes of bonding). , Sealant temperature 20 ° C) is 0.
A moisture-curable sealant having a content of 05 Kg / cm ² or more. 2. The moisture-curable sealant according to claim 1, further comprising a resin (d1) having no active hydrogen and having tackifying property. 3. The sealant according to claim 2, wherein (d1) is one or more resins having no active hydrogen and selected from a low molecular weight xylene resin, a low molecular weight coumarone resin and a low molecular weight styrene resin. 4. An organic polyisocyanate compound (a),
It is derived from a polyol (b1), a thermoplastic urethane resin (c) having an OH group and a resin (d2) having an active hydrogen and having a tackifying property, and having an NCO group of 0.2 to 6
A moisture-curable sealant containing urethane prepolymer (2) having a weight% and having a tensile shear strength (after 5 minutes of joining, sealant temperature 20 ° C.) of 0.05 Kg / cm ² or more. 5. The sealant according to claim 4, wherein (d2) is a low molecular weight xylene resin and / or a low molecular weight coumarone resin having active hydrogen. 6. (c) is derived from an organic polyisocyanate compound (a) and a diol (b2), and the equivalent ratio of the NCO group of (a) and the OH group of (b2) constituting (c) is 0. The sealant according to any one of claims 1 to 5, which has a ratio of 0.5: 1 to 0.98: 1.