JP2580372B2 - Room temperature curable composition and cured product thereof - Google Patents

Description

The present invention relates to a novel composition having a hydroxyl group or a hydrolyzable group at both ends of a molecular chain, which is suitable as a room-temperature curable composition, particularly a sealing material for construction. And a cured product obtained by curing this composition.

(Prior Art) Various kinds of room-temperature-curable compositions mainly composed of polyoxyalkylenes having a hydrolyzable group at the terminal of the molecular chain are already known (JP-B-61-18582, JP-B-Showa No. No. 61-29379, Japanese Patent Publication No. 61-18569, Japanese Patent Publication No. 60-5739
No. 3, Japanese Patent Publication No. 61-36008, Japanese Patent Publication No. 62-34763, Japanese Patent Publication No. 6
Each of these compounds forms a siloxane bond in the presence of moisture in the air and undergoes crosslinking and curing.

Further, with respect to this type of room temperature curable composition, a composition mainly comprising a polyoxyalkylene having a silanol group at a molecular chain terminal is also known (JP-B-55-115446, JP-A-55-123648, JP-A-55-125152, JP-A-55-1310
No. 50, JP-A-2-36260), a silane having at least two hydrolyzable groups bonded to a silicon atom in one molecule or a partial hydrolyzate thereof is used as a crosslinking agent, It crosslinks in the presence to form siloxane bonds and cure.

In the meantime, these room temperature curable compositions are mainly used as architectural sealing materials, but as a sealing material for joints, temperature movement, earthquake, vibration, in order to protect the waterproof function from external forces such as wind, Physical properties after curing are required to be low in modulus and large in elongation.

(Problems to be Solved by the Invention) However, polyoxyalkylene compounds having a molecular weight of up to about 5,000 can be produced as a polyoxyalkylene compound used for producing such a composition, but such a molecular weight can be obtained. Since the composition has a high modulus and a low elongation, there is a disadvantage in that the composition is poor in function as a building sealing material and its use is limited.

For this reason, this polyoxyalkylene compound is subjected to a hydrosilylation reaction of an organohydrogenene polysiloxane having two ≡SiH groups in one molecule with a polyoxyalkylene polymer having unsaturated groups at both ends of the molecular chain to obtain a high molecular weight compound. A method for producing a polyoxyalkylene polymer has also been proposed (see Japanese Patent Publication No. 59-25809).
According to this, a sealing material having a low modulus and a large elongation can be obtained, but two ≡ in one molecule can be obtained.
Organohydrogenpolysiloxanes having SiH groups are expensive and have the drawback that it is not practical to use them industrially.

(SUMMARY for a) The present invention relates to room temperature curable composition and its cured product that solves such disadvantages, which main chain expression ^{_{(CH 2 m OR 1 O n}} CH 2 m SZS _t (CH ₂ ) _m (OR ¹ _n O (CH _{2 m} ) (where R ¹ is a divalent hydrocarbon group having 2 to 4 carbon atoms, and Z is an unsubstituted or 1 to 20 carbon atoms) A substituted divalent hydrocarbon group or a divalent group containing an ether bond or an ester bond having 1 to 20 carbon atoms, or a formula of — (CH ₂ ) _m R ² R ³ SiO (R ² R ³ SiO) _l SiR ² R ³ (CH ₂ ) _m -......
(2) wherein R ² and R ³ are an unsubstituted or substituted monovalent hydrocarbon group having 1 to 6 carbon atoms, l is an integer of 0 to 50, and m is an integer of 2 to 6 N is an integer of 20 to 200, t
The invention is represented by an integer from 1 to 5, wherein the molecular chain terminal _{(X) a (Y) b} R 4 3- (a + b) Si- ...... (3) (R 4 is an unsubstituted Or a substituted monovalent hydrocarbon group, X is a hydroxyl group, Y is a hydrolyzable group, a and b are 0, 1, 2 or 3 and 1 ≦
a + b ≦ 3), 100 parts by weight of a polymer having a hydroxyl group or a hydrolyzable group at a molecular chain terminal, b) a general formula R ⁵ _4-c SiQ _c (where R ⁵ has 1 carbon atom) To 8 monovalent hydrocarbon groups, Q is a hydrolyzable group, and C is 3 or 4)
Or a partially hydrolyzed product thereof represented by
-20% by weight; c) a curing catalyst comprising 0-5 parts by weight; and a cured product obtained by curing the composition.

That is, the present inventors have conducted various studies to develop a novel room-temperature-curable composition that is useful as a building sealing material. As a result, the main chain is represented by the above formula (1).
The polymer (a) having a group represented by the formula (3) described above in its molecular chain terminal, and the (ii) the general formula R ⁵ _4-c organosilane or its partial hydrolysis shown in the SiQ _c as component It was found that when a product and a curing catalyst were added, the product cured at room temperature and became a low-modulus, high-elongation sealing material, and research on the production method of each component used here and the mixing ratio of these components was advanced. Thus, the present invention has been completed.

 This will be described in more detail below.

(Function) The present invention relates to a room temperature curable composition which is useful as a building sealing material because of its low modulus and large elongation, and a cured product obtained by curing the composition.

A polymer as a) component constituting the room temperature curable composition of the present invention is the main chain formula ^{_{(CH 2 m OR 1 O n}} CH 2 m SZS t (CH 2) m (OR 1 n O (CH 2 m R ¹ is an ethylene group, a propylene group, a divalent hydrocarbon group having 2 to 4 carbon atoms such as a butylene group, Z is -CH _2- ,
_{-CH 2 CH 2 -, - CH} 2 CH 2 CH 2 -, - CH 2 -CH 2 CH 2 CH 2 CH 2 -,
−CH ₂ CH ₂ CH ₂ CH ₂ CH ₂ CH ₂ CH ₂ −, −C ₆ H ₄ −, −CH ₂ CH (CH ₂ O
_{H) -, - CH 2 (} OH) CHCH (OH) CH 2 - are illustrated in the unsubstituted or substituted divalent hydrocarbon group having 1 to 20 carbon atoms, -CH ₂ C
H ₂ OCH ₂ CH ₂ CH _2- , -CH ₂ CH ₂ OCH ₂ CH ₂ O -CH _2- , CH ₂ COOCH ₂
CH ₂ OCOCH ₂ —, —CH ₂ COOCH ₂ (CH ₃ ) —CHOCOCH ₂ —, a divalent organic group having 1 to 20 carbon atoms containing an ether bond or an ester bond, or a formula of — (CH ₂ ) _m R ² R ³ SiO (R ² R ³ SiO) ₁ SiR ² R ³ (CH ₂ ) _m −, wherein R ² and R ³ are a methyl group, an ethyl group, a propyl group,
Alkyl group such as butyl group, cycloalkyl group such as cyclohexyl group, alkenyl group such as vinyl group and allyl group, aryl group such as phenyl group, or part or all of hydrogen atoms bonded to carbon atoms of these groups Is substituted with a halogen atom, a cyano group, etc.
C1-C6 unsubstituted or substituted 1 selected from a 3,3,3-trifluoropropyl group, a 2-cyanoethyl group, etc.
A divalent hydrocarbon group, l is an integer of 0 to 50, m is an integer selected from siloxane-containing groups of 2 to 6, and n is
An integer of 20 to 200, t is an integer of 1 to 5,
This compound is shown in its molecular chain terminal by the formula _{(X) a (Y) b} R 4 3- (a + b) Si- ...... (3), R 4 is the same as R ^2, R ³ mentioned above , Usually 1 carbon
~ 10, preferably unsubstituted or substituted 1 to 8 carbon atoms
A hydrocarbon group, X is a hydroxyl group, and Y is the same or different, and a methoxy group, an ethoxy group, a propoxy group, a butoxy group, an alkoxy group such as a methoxyethoxy group, an ethoxyethoxy group, etc .; an acetoxy group, a propionoxy group, a butyroxy group, etc. An alkenyloxy group such as a propenyloxy group or an isobutenyloxy group; an iminoxy group such as a dimethylketoxime group, a methylethylketoxime group, a diethylketoxime group, a cyclopentanoxime group, or a cyclohexanoxime group; Amino groups such as methylamino group, N-ethylamino group, N-propylamino group, N-butylamino group, N, N-dimethylamino group, N, N-diethylamino group, cyclohexylamino group; N-methylacetamide group , N-ethylacetamide group, N-methylbenzamide group, etc. A hydrolytic group such as an aminooxy group such as an N, N-dimethylaminooxy group or an N, N-diethylaminooxy group; a, b is 0, 1, 2 or 3 and 1 ≦ a + b ≦ 3 It has a certain group.

The polymer mainly containing a polyoxyalkylene bond can be industrially produced using a polyoxyalkylene polymer having an unsaturated group at both ends of the molecular chain.

That is, first the general formula _{CH 2 = CHCH 2 m-2} OR 1 O n CH 2 m-2 CH = CH 2 ...... about this
Organo represented by the general formula polyoxyalkylene polymer having an unsaturated group at a molecular chain terminal represented by (4) (X) a ( Y) b HR 4 3- (a + b) Si ...... (5) Hydrogen silane is subjected to an addition reaction by a hydrosilylation reaction to synthesize a polymer represented by the following formula having an unsaturated group and a hydrolyzable group at one end.

_{(X) a (Y) b} R 4 3- (a + b) Si (CH 2) m O (R 1 O) n (CH 2) m-2 CH = CH 2 ...... (6) This reaction is known Therefore, this may be performed by the method of 0.1 to 1,000 rpm as platinum metal based on the total amount of the polyoxyalkylene polymer represented by the formula (4) and the organosilane represented by the formula (5). Preferably, 1 to 100 ppm of a platinum catalyst for an addition reaction, for example, finely powdered platinum, chloroplatinic acid, chloroplatinic acid-olefin complex, chloroplatinic acid-vinylsiloxane complex, and the like, toluene, xylene, and the like are added as necessary. 60 in the presence of a solvent
What is necessary is just to heat and react at -200 degreeC for about 0.5 to 5 hours.

The polyoxyalkylene polymer represented by the above formula (6) thus obtained has two mercapto groups in one molecule represented by the general formula HSZSH (7) (Z is as described above). if brought into compound chemically reacting general formula _{(X) a (Y) b} R 4 3- (a + b) Si (CH 2) m -O- (R 1 O) n (CH 2) m SZS (CH 2 ^{_{) m -O- (R 1 O)}} n (CH 2) m SiR 4 3- (a + b) (X) a (Y) b ...... hydroxyl or hydrolyzable end of the molecular chain represented by (8) A polymer having a group and mainly containing a polyoxyalkylene bond as the component (a) in the present invention can be obtained.

Incidentally, the general formula (7) ₂ wherein HSCH as the mercapto group-containing compound represented by SH used _{herein, HSCH 2 CH 2 SH, HSCH} 2 CH 2 CH 2 SH, HSCH 2 CH 2 -CH 2 CH 2 _{CH 2 SH, HSC 6 H 4} SH, HSCH 2 CH (CH 2 OH) SH, HSCH 2 - (OH) CHCH (OH) CH 2 SH, HSCH 2 CH 2 OCH 2 CH 2 CH 2 SH, HSCH 2 CH 2 _{OCH 2 CH 2 OCH 2 CH 2} SH, HSCH 2 COOCH 2 CH 2 OCO-CH 2 SH, HSCH 2 COOCH 2 (CH 3) CHOCOCH 2 SH, SH (CH 2) n -R 2 R 3 SiO (R 2 R ³ SiO) _l SiR ² R ³ (CH ₂ ) _n SH, etc., and the reaction is benzoyl peroxide, bis (2,4-dichlorobenzoyl) peroxide, di-t-butyl peroxide, 2, 5-dimethyl-
Peroxides such as di-t-butylperoxyhexane, t-butylperbenzoate, t-butylperoxyisopropyl carbonate, dicumyl peroxide, ammonium persulfate, and persulfates such as N, N-bisisobutyronitrile A radical forming catalyst comprising a diazo compound or the like or an alkali catalyst such as an alkali metal alkoxide is used in an amount of 0.01 to 5 parts by weight, particularly 0.05 to 3 parts by weight, per 100 parts by weight of the polyoxyalkylene polymer represented by the above (6).
It is only necessary to add parts by weight and heat and react at a temperature of 30 to 150 ° C. for about 5 minutes to 5 hours. In this case, infrared rays, ultraviolet rays,
X-rays, α-rays, β-rays, etc. may be irradiated.

Further, the synthesis of the polymer as the component (a) used in the present invention is carried out by synthesizing a polyoxyalkylene polymer having an unsaturated group (for example, a vinyl group) at both ends of the molecular chain represented by the general formula (4), A compound containing two mercapto groups in one molecule represented by the following general formula (7) and a general formula HSR ⁶ _d Si (X) _3-d (9), wherein R ⁶ has 1 carbon atom To 6 divalent hydrocarbon groups, d is 0
Alternatively, it can be obtained by reacting the same with a mercapto group-containing organosilane as 1, using the same radical-forming catalyst as described above.

Those described below as a polymer as a) component produced in this _{way, (CH 3 O) 3 SiC} 3 H 6 SC 3 H 6 O [CH 2 CH (CH 3) O] 80 C 3 H 6 S- CH
₂ CH ₂ CH ₂ CH ₂ CH ₂ SC ₃ H ₆ O [CH ₂ CH (CH ₃ ) O] ₈₀ C ₃ H ₆ -SC ₃ H
₆ SC ₃ H ₆ Si (OCH ₃ ) ₃ , (CH ₃ O) ₃ SiC ₃ H ₆ SC ₃ H ₆ O− [CH ₂ CH
_{(CH 3) O] 80 C} 3 H 6 S-C 3 H 6 (CH 3) 2 SiO [(H 3 O) 2 SiO]
₁₀ SiH (CH ₃ ) ₂ C ₃ H ₆ SC ₃ H ₆ O [CH ₂ —CH (CH ₃ ) O] ₈₀ C ₃ H ₆ S
i (OCH ₃ ) ₃ , (CH ₃ O) ₂ (CH ₃ ) SiC ₃ H ₆ O [CH ₂ CH (C
_{H 3) -O] 80 -C 3} H 6 SCH 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 SC 3 H 6 O [CH 2
_{CH- (CH 3) O] 80} C 3 H 6 Si (CH 3) (OCH 3) 2, (CH 3 O)
₂ (CH ₃ ) SiC ₃ H ₆ O [CH ₂ —CH (CH ₃ ) O] ₈₀ C ₃ H ₆ —SC ₃ H _{6
H (CH 3) 2 SiO [} (CH 3) 2 SiO] 10 Si (CH 3) 2 C 3 H 6 -SC 3 H 6
O [CH ₂ CH (CH ₃ ) O] ₈₀ C ₃ H ₆ Si (CH ₃ ) (OCH ₃ ) ₂ is exemplified, and these are represented by the general formula (4) as a starting material
Since the unsaturated group-containing polyoxyalkylene compound represented by can be produced relatively easily on an industrial scale with a molecular weight of up to about 6,000, the molecular weight can be increased. The room temperature curable composition of the invention has the advantage of providing a low modulus, high elongation sealant.

Also, organosilane as b) component constituting the room temperature curable composition of the present invention is represented by the general formula ^{_{R 5 4-C SiQ C,}} R
⁵ has the same unsubstituted or substituted carbon number of 1 as defined above for R ² and R ³
To 8 monovalent hydrocarbons, Q is the same hydrolyzable group as Y described above, and organosilane in which C is 3 or 4, such as methyltrimethoxysilane, methyltri (methylethylketoxime) silane, methyltripropynyloxysilane, Methyltriacetoxysilane and silanes in which the methyl group of these silane compounds has been changed to a vinyl group, a phenyl group, a trifluoropropyl group, and the like, and further a partial hydrolyzate thereof, are exemplified. If the amount is less than 1 part by weight per 100 parts by weight of the polymer as a component), the room temperature-curable composition of the present invention has poor storage stability. If the amount is more than 20 parts by weight, the cured product becomes too hard, Since it is economically disadvantageous, it is necessary to be in the range of 1 to 20 parts by weight.
To 10 parts by weight. Further, the curing catalyst as the component (c) constituting the room temperature curable composition of the present invention may be a known one, and includes tin carboxylate such as tin naphthenate, tin caprylate, tin oleate, and cibutyltin ditin. Tin compounds such as acetate, dibutyltin dioctate, dibutyltin dilaurate, dibutyltin dioleate, diphenyltin diacetate, dibutyltin oxide, dibutyltin dimethoxide, tin dibutylbis (triethoxysiloxy), and dibutyltin dibenzylmalate; tetraisopropoxytitanium , Titanium n-butoxytitanium, tetrakis (2-ethylhexoxy) titanium dipropoxybis (acetylacetona) titanium, titanium isopropoxyoctylene glycol, and other titanic acid esters or titanium chelate compounds. There are exemplified. This catalyst is for accelerating the curing of the composition comprising the above-mentioned component a) and component b), and may not be used in some cases, but is usually for accelerating the curing. It is preferable to use 5 parts by weight or less, particularly 1 part by weight or less, based on 100 parts by weight of the polymer as the component (a).

The room temperature-curable composition of the present invention includes the above-mentioned (a), (b),
(C) It can be obtained by uniformly mixing a predetermined amount of the component. This includes, as necessary, a silane containing a propenyloxy group or a partial hydrolyzate thereof as a cross-linking agent, and further, tetramethylguanidyl propyl trisilane. A guanidyl group-containing silane such as methoxysilane, tetramethylguanidylpropyldimethoxysilane, tetramethylguanidylpropyl tris (trimethylsiloxy) silane and a partial hydrolyzate thereof, and a guanidyl group-containing siloxane may be added. In addition, a filler may be blended for the purpose of reinforcing or increasing the amount. The filler may be known, and thus includes fumed silica, calcined silica, precipitated silica, ground silica, fused silica powder,
Diatomaceous earth, metal oxides such as iron oxide, zinc oxide, titanium oxide, barium oxide, and magnesium oxide; metal carbonates such as calcium carbonate, magnesium carbonate, and zinc carbonate;
Examples thereof include metal hydroxides such as cerium hydroxide and aluminum hydroxide, glass fibers, glass wool, carbon black, fine mica, asbestos, and those whose surfaces have been subjected to a hydrophobic treatment with silane or the like.

Further, the composition may further comprise a thixotropic agent such as polyethylene glycol and its derivative, a pigment, a dye, an antioxidant, an antioxidant, an antistatic agent, an antimony oxide, a flame retardant such as paraffin chloride, and a nitriding agent, if necessary. It is optional to add a thermal conductivity improver such as boron or aluminum oxide, and an organosilicon compound having a reactive organic group such as an amino group, an epoxy group, or a mercapto group as an adhesion promoter. Various conventionally known additives such as a so-called silane coupling agent may be added.

In addition, in order to use the room temperature-curable composition of the present invention as a building sealing material, it may be applied as it is, but for convenience at the time of use, it may be applied with toluene, xylene, petroleum ether or the like. May be diluted with solvents such as hydrocarbon solvents, ketones, and esters, and further include a plasticizer, an anti-sagging agent, a known antifouling agent, an antiseptic, a bactericide, a fungicide, and the like. Is also good.

(Examples) Next, a synthesis example of a polymer as the component (a) used in the present invention, and examples and comparative examples of the present invention will be described.

Synthesis Example 1 Formula CH ₂ CHCHCH ₂ O [CH ₂ CH (CH ₃ ) O] ₈₀ CH ₂ CH ＝ CH ₂ CH ₂ CH ₂ CH ₂ CH ₂ end 474 g of polyoxyalkylene polymer having both ends blocked with vinyl groups, 300 g of toluene , And subjected to a dehydration treatment at the reflux temperature of toluene for 1 hour. Then, 6.8 g of a mercapto group-containing compound represented by the formula HSCH ₂ CH ₂ CH ₂ CH ₂ CH ₂ SH and the formula HSCH ₂ CH ₂ CH ₂ Si 19.6 g of a mercapto group-containing alkoxysilane represented by (CH ₃ ) ₃ and 10 g of N, N-bisisobutyronitrile as a catalyst
, And reacted at 100 to 110 ° C for 3 hours.
Stripping was performed for 2 hours under the condition of 0 mmHg.
A liquid with a viscosity of 12,000 cS at 5 ° C was obtained,
This is of the formula (CH ₃ O) ₃ SiC ₃ H ₆ SC ₃ H ₆ O [CH ₂ CH (CH ₃ ) O] ₈₀ − C ₃ H ₆ SCH ₂ CH ₂ CH ₂ CH ₂ CH ₂ SC ₃ H ₆ O was _{[CH 2 CH (CH 3)} O] 80 -C 3 H 6 SC 3 H 6 Si (OCH 3) ( hereinafter abbreviated as polymer I) polymer represented by _3.

Synthesis Examples 2 to 4 Instead of 6.8 g of HSCH ₂ CH ₂ CH ₂ CH ₂ CH ₂ SH compound containing mercapto group used in Synthesis Example 1 described above a) HSCH ₂ CH ₂ OH ₂ CH ₂ OCH ₂ CH ₂ SH 9.1 g B) HSCH ₂ COOCH ₂ CH ₂ OCOCH ₂ SH 10.5 g, c) HSC ₃ H ₆ (CH ₃ ) ₂ SiO [(CH ₃ ) ₂ SiO] ₁₀ Si (CH ₃ ) ₂
The reaction was carried out in the same manner as in Synthesis Example 1 except that 51 g of -C ₃ H ₆ SH was used.
The following three polymers were obtained.

Polymer _{II (CH 3 O) 3 SiC} 3 H 6 SC 3 H 6 O [CH 2 CH (CH 3) O] 80 C 3 H 6 -S
CH ₂ CH ₂ OCH ₂ CH ₂ OCH ₂ CH ₂ SC ₃ H ₆ O [CH ₂ CH (CH ₃ ) O] ₈₀ −C _{3
H 6 SC 3 H 6 Si (} OCH 3 O) 3, Polymer _{III (CH 3 O) 3 SiC} 3 H 6 SC 3 H 6 O [CH 2 CH (CH 3) O] 80 C 3 H 6 -S
CH ₂ CCOOCH ₂ CH ₂ OCOCH ₂ SC ₃ H ₆ O [CH ₂ CH (CH ₃ ) O] ₈₀ −C ₃ H
_{6 SC 3 H 6 Si (OCH} 3 O) 3, polymer _{IV (CH 3 O) 3 SiC} 3 H 6 SC 3 H 6 O [CH 2 CH (CH 3) O] 80 C 3 H 6 -S
_{C 3 H 6 (CH 3)} 2 SiO [(CH 3) 2 SiO] 10 Si (CH 3) 2 C 3 H 6 -SC
_{3 H 6 O [CH 2 CH} (CH 3) O] 80 C 3 H 6 SC 3 H 6 Si (OCH 3) 3.

Synthesis Examples 5 to 7 After dehydrating the polyoxyalkylene polymer used in Synthesis Example 1 whose molecular chain ends are blocked with a vinyl group in the same manner as in Synthesis Example 1, 0.54% isopropanol of chloroplatinic acid was added as a catalyst to 474 g of the polymer. 0.5 g of the solution was added, and the mixture was heated to 80 ° C., 10.6 g of methyldimethoxysilane was gradually added dropwise, and the mixture was further reacted at 80 to 90 ° C. for 2 hours, and then cooled to 25 ° C. The following three types of mercapto group-containing compounds d), e), f) d) HSCH ₂ CH ₂ OCH ₂ CH ₂ OCH ₂ CH ₂ SH 9.1 g, e) HSCH ₂ COOCH ₂ CH ₂ OCOCH ₂ SH 10.5 g, f ) HSC ₃ H ₆ (CH ₃ ) ₂ SiO [(CH ₃ ) ₂ SiO] ₁₀ Si (CH ₃ ) ₂ C ₃
After adding 51 g of H ₆ SH, adding 10 g of benzophenone as a catalyst, and irradiating with ultraviolet rays for 30 minutes using high-pressure mercury or the like, the following 3
A kind of polymer was obtained.

Polymer V (CH ₃ O) ₂ (CH ₃ ) SiC ₃ H ₆ O [CH ₂ CH (CH ₃ ) O] ₈₀ C ₃ H ₆
SCH ₂ -CH ₂ OCH ₂ CH ₂ OCH ₂ CH ₂ SC ₃ H ₆ O [CH ₂ CH (CH ₃ ) O] ₈₀
—C ₃ H ₆ —Si (CH ₃ ) (OCH ₃ ) ₂ , Polymer VI (CH ₃ O) ₂ (CH ₃ ) SiC ₃ H ₆ O [CH ₂ CH (CH ₃ ) O] ₈₀ C ₃ H ₆
SCH ₂ -COOCH ₂ CH ₂ OCOCH ₂ SC ₃ H ₆ O [CH ₂ CH (CH ₃ ) O] ₈₀ C ₃ H
_{6 Si- (CH 3) (OCH} 3) 2, polymer _{VII (CH 3 O) 2 (} CH 3) SiC 3 H 6 O [CH 2 CH (CH 3) O] 80 C 3 H 6
SC ₃ H ₆ − (CH ₃ ) ₂ SiO [(CH ₃ ) ₂ SiO] ₁₀ Si (CH ₃ ) ₂ C ₃ H ₆ S
_{C 3 H 6 O- [CH 2} CH (CH 3) O] 80 C 3 H 6 Si (CH 3) (OC
H ₃ ) ₂ , Synthesis Example 8 After dehydrating the polyoxyalkylene polymer used in Synthesis Example 1 in which the molecular chain ends are blocked with a vinyl group in the same manner as in Synthesis Example 1, 474 g of the formula HSCH ₂ CH ₂ CH was added. ₂ Si (OCH
Mercapto group-containing organosilane 39.2g represented by _{3) 3}
And 10 g of N, N-bisisobutyronitrile as a catalyst
After reacting at 100-110 ° C for 3 hours, and then stripping at 100 ° C and 10 mmHg for 2 hours, a liquid having a viscosity of 1,200 cS at 25 ° C was obtained, which is represented by the following formula. (Hereinafter referred to as Polymer VIII
Abbreviated).

_{(CH 3 O) 2 SiC 3} H 6 SC 3 H 6 O [CH 2 CH (CH 3) O] 80 C 3 H 6 SC 3
H ₆ Si (OCH ₃ ) ₃ Synthesis Example 9 After dehydrating the polyoxyalkylene polymer used in Synthesis Example 1 having a molecular chain terminal blocked with a vinyl group in the same manner as in Synthesis Example 1, 474 g of this polymer was used as a catalyst. 0.5 g of a 0.5% solution of chloroplatinic acid in isopropanol was added, and the mixture was heated to 80 ° C., and 21.2 g of methyldimethoxysilane was gradually added dropwise thereto. The mixture was allowed to react at 80 to 90 ° C. for 2 hours.
After stripping for 2 hours under the conditions of g, a liquid having a viscosity of 3,000 cS at 25 ° C. is obtained, which has the formula (CH ₃ O) ₂ (CH ₃ ) SiC ₃ H ₆ O [CH ₂ CH (CH ₃ ) O] ₈₀ C ₃ H ₆ Si— (CH ₃ ) (OCH ₃ ) ₂ (hereinafter abbreviated as polymer IX).

Examples 1 to 7 and Comparative Examples 1 to 2 800 g of polymers I to IX obtained in Synthesis Examples 1 to 9, 200 g of dioctyl phthalate, and 1,000 g of precipitated calcium carbonate were mixed with a three-roll mill to make a base compound. 200 g of compound, 5 g of methyltrimethoxysilane, 1 g of dibutyltin dilaurate as a catalyst, γ-
1 g of aminopropyltriethoxysilane and 1 g of γ-guanidylpropyltrimethoxysilane were added and mixed well to produce a one-part room temperature curable composition.

Then, the composition was formed into a sheet having a thickness of 2 mm,
Let it cure for 7 days in an atmosphere of 60 ° C and 60% RH, and determine its physical properties (hardness, tensile strength, elongation) according to JIS-K-6301.
As a result, the results shown in Table 1 were obtained.

Next, a JIS-like composition as shown in FIG.
A-5758 H-shaped block was prepared, and 5 mm thick glass was used as an adherend. The glass was left to stand at 23 ° C and a relative humidity of 55% for 7 days, and then left at 30 ° C for 7 days to cure. And perform a tensile test on this
When the 50% modulus, the maximum tensile strength and the maximum elongation were measured, the results as shown in Table 1 were obtained.

(Effect of the Invention) The present invention relates to room temperature curable composition which is suitable as such as construction sealants, which as described above b) a main chain has the formula ^{_{(CH 2 m OR 1 O n}} CH 2 _m SZS _t (CH ₂ ) _m (OR ¹
_n O (indicated by CH _{2 m} , the end of a partial chain of the formula (X) _a (Y) _b R ⁴
_{3- (a + b)} polymer having a group represented by the Si-, b) the general formula R ⁵ _4-c SiQ organosilane or a partial hydrolyzate thereof represented by _c, is made of a c) a curing catalyst However, it cures at room temperature due to moisture in the air and has the advantage of being particularly useful as a building sealant due to its low modulus and high elongation.

[Brief description of the drawings]

FIG. 1 is a perspective view of an H-shaped block for measuring modulus, tensile strength, and elongation in a tensile test in Examples.

Claims (2)

(57) [Claims] 1. A i) main chain has the formula ^{_{(CH 2 m OR 1 O n}} CH 2 m SZS t (CH 2) m (OR 1 n O (CH 2 m [ wherein the R ¹ is from 2 to 4 carbon atoms A divalent hydrocarbon group, Z is an unsubstituted or substituted divalent hydrocarbon group having 1 to 20 carbon atoms,
A divalent organic group containing an ether bond or an ester bond to 20, or an expression ^{_{- (CH 2) m R 2}} R 3 SiO (R 2 R 3 SiO) l SiR 2 R 3 (CH 2) m - ( here R ² and R ³ are an unsubstituted or substituted monovalent hydrocarbon group having 1 to 6 carbon atoms; l is an integer of 0 to 50; m is an integer of 2 to 6); 20-200 integer, t is those represented by an integer from 1 to 5], the molecular chain ends to formula _{(X) a (Y) b} R 4 3- (a + b) Si- (R 4 is An unsubstituted or substituted monovalent hydrocarbon group, X is a hydroxyl group, Y is a hydrolyzable group,
a and b are 0, 1, 2 or 3 and 1 ≦ a + b ≦ 3)
A) a polymer having a hydroxyl group or a hydrolyzable group at the terminal of the molecular chain having a group represented by the general formula R ⁵ _4-c SiQ _c (where R ⁵ is an unsubstituted or substituted monovalent having 1 to 8 carbon atoms) A hydrocarbon group, Q is a hydrolyzable group, c
A curable composition at room temperature, comprising: 1 to 20 parts by weight of an organosilane represented by 3 or 4) or a partial hydrolyzate thereof; and c) 0 to 5 parts by weight of a curing catalyst. 2. A cured product obtained by curing the composition according to claim 1.