JP3030267B2 - Curable composition - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION The present invention relates to a silicon-containing group having a hydroxyl group or a hydrolyzable group bonded to a silicon atom and capable of crosslinking by forming a siloxane bond (hereinafter referred to as "silicon-containing group").
A curable composition comprising an oxyalkylene polymer having a reactive silicon group) and a specific oxyalkylene polymer having a high molecular weight hydroxyl group, which is applied to a cured product of the composition. The present invention relates to a curable composition having improved alkyd-based paint with improved drying properties.

[0002]

2. Description of the Related Art An oxyalkylene polymer having a reactive silicon group is cured even at room temperature by moisture in the air at room temperature, such as a silicon rubber curable at room temperature, to form a rubber-like material. It is a polymer to give. Because this cured product has excellent elongation properties, strength, adhesiveness, etc.
Used for applications such as sealants and adhesives.

One of the features of the oxyalkylene polymer having a reactive silicon group is that most of commonly used paints can be applied to the surface of a cured product because the main chain is an oxyalkylene polymer. It is. In addition,
In the case of silicone rubber, there is a problem that the surface is water- and oil-repellent and it is practically impossible to apply a paint.

However, even when a cured product of a composition using an oxyalkylene polymer having a reactive silicon group is applied with an alkyd paint, depending on the type of the composition,
In some cases, the drying property (curability) of the coating film is poor, and it is practically difficult to use the coating material in the cured product. In such a case, it has been almost abandoned to apply an alkyd paint on a cured product of a sealant using an oxyalkylene polymer.

However, the alkyd paint dries faster than the oil paint, and the coating is hard and glossy, and is excellent in almost all aspects such as adhesion, weather resistance, oil resistance and resistance. Since the physical properties can be adjusted in a wide range depending on the type of denatured oil, oil length, type of denaturation, etc., it is a paint used for various applications. Therefore, it is very beneficial to be able to apply this paint on the surface of the cured product.

Although the cause of the deterioration of the drying property of the alkyd paint has not been known at all, the present inventors have conducted intensive studies on the cause and found that the oxyalkylene-based polymer having a reactive silicon group was found. It has been found that when a conventional low molecular weight plasticizer is added to a curable composition containing the compound, the drying property is deteriorated. The plasticizer is added when it is necessary to lower the viscosity of the composition (improve the workability during use) or to improve the tensile properties of the cured product.

Since it is a simple method to use a plasticizer to lower the viscosity of the composition and improve the tensile properties of the cured product, the present inventors have a plasticizer that does not deteriorate the drying property of the alkyd paint. As a result of the search, it has been found that the use of a polymeric plasticizer improves the above-mentioned problem.

Among the polymeric plasticizers, oxyalkylene polymers are inexpensive, and when added to oxyalkylene polymers having a reactive silicon group, the cured product has excellent tensile properties at low temperatures. Excellent plasticizer.

The present inventors have studied various oxyalkylene polymers, and as a result, when a specific oxyalkylene polymer is used as a plasticizer for an oxyalkylene polymer having a reactive silicon group, the cured product becomes very poor. The present inventors have found that alkyd paints have excellent drying properties, and have reached the present invention.

[0010]

That is, the present invention relates to (A) a compound having a hydroxyl group or a hydrolyzable group bonded to a silicon atom and having at least one silicon-containing group which can be crosslinked by forming a siloxane bond. Oxyalkylene polymer and (B) weight average molecular weight (Mw) / number average molecular weight (Mn)
Curable composition containing a hydroxyl group-containing oxyalkylene polymer having a number average molecular weight of 4,000 or more (claim 1) of not more than 1.5 , and (A) a hydroxyl group or a hydroxyl group bonded to a silicon atom. Degradable group
Crosslinks by forming siloxane bonds
Oxyalkylene having at least one silicon-containing group
Containing a hydroxyl group having a number average molecular weight of 4000 or more, in which the proportion of a monomeric polymer and ( C) a component having a molecular weight of 1000 or less is 10% by weight or less .
Curable composition containing the oxyalkylene polymer (claim 2 ).

[0011]

DESCRIPTION OF THE PREFERRED EMBODIMENTS In the present invention, an oxyalkylene polymer having at least one reactive silicon group (hereinafter, also referred to as an oxyalkylene polymer (A)) is used.

The oxyalkylene polymer (A) is
JP-B-45-36319, JP-B-46-12154, JP-A-49-32673, JP-A-50-156599, JP-A-51-73561, JP-A-54-6096, and JP-A-55-8.
No. 2123, No. 55-123620, No. 55-125
No. 121, No. 55-13022, No. 55-1351
No. 35, 55-137129, and the like.

The molecular chain of the oxyalkylene polymer (A) has a general formula: -R ¹ -O- (wherein R ¹ is a divalent hydrocarbon group, most of which are carbon atoms). preferably one having a repeating unit of represented by the most preferred) when an alkylene group having 3 or 4. Specific examples of R ¹ include:

[0014]

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And the like. The oxyalkylene molecular chain of the alkylene polymer (A) may consist repeating units of only one kind, or may be made of two or more repeating units, but especially as R ¹

[0016]

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Is preferred.

The main chain of the oxyalkylene polymer may be composed of only a repeating unit represented by the general formula: -R ¹ -O-, or may contain other repeating units. When other repeating units are contained, the repeating unit represented by the general formula: —R ¹ —O—
% (% By weight, hereinafter the same), and more preferably 80% or more.

The reactive silicon group which can be cross-linked and / or polymerized by forming a siloxane bond in the oxyalkylene polymer (A) is a well-known functional group, and has a feature of being cross-linkable even at room temperature. Have. A typical example of the reactive silicon group is represented by the general formula (I):

[0020]

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Wherein R ² is a substituted or unsubstituted monovalent organic group having 1 to 20 carbon atoms or a triorganosiloxy group, and (m (2-a) + 3-b) R ² X is a hydroxyl group or a hydrolyzable group, and (m
a + b) Xs can be different, a is 0, 1 or 2, b is 0, 1, 2 or 3, and (ma +
b) ≧ 1, m is an integer of 0 to 19, and m

[0022]

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A need not be the same). Among the reactive silicon groups represented by the general formula (I), the general formula (I)
I):

[0024]

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(Wherein R ² is the same as above and l is 1, 2 or 3).

Specific examples of the hydrolyzable group which is one type of X in the general formula (I) include, for example, a halogen atom, a hydrogen atom, an alkoxy group, an acyloxy group, a ketoximate group, an amino group, an amide group, an aminooxy group , A mercapto group, an alkenyloxy group and the like. Among these, an alkoxy group such as a methoxy group and an ethoxy group is preferred from the viewpoint of mild hydrolysis.

Specific examples of R ² in the general formula (I) include, for example, an alkyl group such as a methyl group and an ethyl group, a cycloalkyl group such as a cyclohexyl group, an aryl group such as a phenyl group, and an aralkyl group such as a benzyl group. Or (R ′) ₃ SiO— (R ′ is a substituted or unsubstituted monovalent organic group having 1 to 20 carbon atoms such as a methyl group and a phenyl group, and three R ′s do not need to be the same. ), And the like. Of these, a methyl group is particularly preferred.

The number of reactive silicon groups in the oxyalkylene polymer (A) may be one or more per molecule.
From the viewpoint of obtaining sufficient curability, the average is preferably 1.1 or more, and more preferably 1.5 to 4 on the average. Further, the reactive silicon group is preferably present at the terminal of the molecular chain of the oxyalkylene polymer (A).

The number average molecular weight of the oxyalkylene polymer (A) is preferably from 3,000 to 30,000,
Those having a molecular weight of 5,000 to 15,000 are more preferred. The oxyalkylene polymer (A) may be used alone or in combination of two or more.

The oxyalkylene polymer (A) is, for example, a hydrosilane compound having a hydrogen atom bonded to a group represented by the general formula (I) and a general formula (III):

[0031]

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(Wherein R ³ is a hydrogen atom or a group having 1 to 1 carbon atoms)
20 is a monovalent organic group, R ⁴ is a divalent organic group having 1 to 20 carbon atoms, c is 0 or 1) and an oxyalkylene-based polymer having an olefin group represented by 1).
It is produced by a method such as an addition reaction using a group III transition metal compound as a catalyst.

As another method for producing the oxyalkylene polymer (A), a polyisocyanate compound such as toluene diisocyanate is reacted with a hydroxyl group-terminated oxyalkylene polymer to form an isocyanate group-terminated alkylene oxide polymer. And then the general formula (I)
V):

[0034]

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Wherein W is an active hydrogen-containing group such as a hydroxyl group, a carboxyl group, a mercapto group or an amino group (primary or secondary), and l, R ² , R ⁴ and X are as defined above. A method of reacting a W group of a silicon compound, a mercapto compound of a silicon compound represented by the general formula (IV) in which W is a mercapto group to an olefin group of an oxyalkylene polymer having an olefin group represented by the general formula (III) A method of adding a group, and adding a hydroxyl group of an oxyalkylene polymer having a hydroxyl group to a hydroxyl group of the general formula (V):

[0036]

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(Wherein R ² , R ⁴ , X and l are as defined above), and the like. Specific examples thereof include, but are not limited to, the present invention. Absent.

In the method of reacting a hydrosilyl compound having a hydrogen atom bonded to the group represented by the general formula (I) with an oxyalkylene polymer having an olefin group represented by the general formula (III), Thereafter, some or all of the X groups may be further converted to other hydrolyzable groups or hydroxyl groups. For example, when the X group is a halogen atom or a hydrogen atom, these groups are preferably used after being converted into an alkoxy group, an acyloxy group, an aminooxy group, an alkenyloxy group, a hydroxyl group or the like.

In the general formula (III), R ³ is a hydrogen atom or a substituted or unsubstituted monovalent organic group having 1 to 20 carbon atoms, and is preferably a hydrogen atom or a hydrocarbon group. It is preferably an atom.

R ⁴ is a divalent organic group having 1 to 20 carbon atoms, and is represented by —R ⁵ —, —R ⁵ OR ⁵ —,

[0041]

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(R ⁵ is a divalent hydrocarbon group having 1 to 10 carbon atoms) and the like, and particularly preferably a methylene group.

As a specific method for producing the oxyalkylene polymer having an olefin group represented by the general formula (III), for example, as disclosed in JP-A-54-6097, A method of reacting a compound having an unsaturated group with a terminal hydroxyl group of the coalesced to form an ether bond, an ester bond, a urethane bond, a carbonate bond, or the like; or a method of polymerizing an epoxy compound such as ethylene oxide or propylene oxide. And a method in which an olefin group-containing epoxy compound such as allyl glycidyl ether is added and copolymerized to introduce an olefin group into a side chain.

In the present invention, together with the oxyalkylene polymer (A) , the weight average molecular weight (Mw) / number average
Number average molecular weight of 1.5 or less in molecular weight (Mn) is 400
Oxyalkylene polymer containing zero or more hydroxyl groups
(Hereinafter referred to as oxyalkylene polymer (B))
Means that the proportion of components having a molecular weight of 1000 or less is 10% or less
Oxygen containing hydroxyl group having a number average molecular weight of 4000 or more
Alkylene polymer (hereinafter, oxyalkylene polymer)
(Referred to as (C)) . The oxyalkylene-based polymer ( B) or the oxyalkylene-based polymer ( C) adjusts properties such as viscosity reduction and cost reduction of the composition, and hardness and elastic modulus of a cured product from the composition, When the alkyd paint is applied to the cured product, it is a component for facilitating drying of the coating film.

[0045] The contact oxyalkylene polymer that is substantially free of hydroxyl groups (hereinafter, the oxyalkylene polymer that (D)) is also the oxyalkylene polymer (B) The
It may be used for the same purpose as the oxyalkylene polymer (C). You may use together with an oxyalkylene polymer (B) or an oxyalkylene polymer (C).

The oxyalkylene polymer (B) and
Kishiarukiren polymer (C) is not intended either including room temperature crosslinkable group such as reactive silicon group oxyalkylene polymer (A) has since used as a plasticizer.

The oxyalkylene polymer (B) and
The main chain of Kishiarukiren polymer (C), as with any Oki <br/> Shiarukiren based polymer (A), essentially, that of the monomer units constituting the main chain 60 %that's all,
Preferably, 80% or more is represented by the general formula: -R ¹ -O-. In R ¹

[0048]

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Is preferred.

[0050] The number average molecular weight of the oxyalkylene polymer (B) and o <br/> Kishiarukiren polymer (C) is either
Although also necessary 4000 or more, preferably 4500 or more, more preferably 5000～15,000.
When the number average molecular weight is less than 4,000, if the polymer contains a hydroxyl group, when the alkyd paint is applied to the cured product, the drying property of the coating tends to be poor.

The oxyalkylene polymer (C) further contains 10% of a component having a number average molecular weight of 1,000 or less.
(Percentage from the value measured by the GPC method, the same applies hereinafter) Does the following point improve the drying property of the alkyd paint ?
And it is particularly preferred that the content be 5% or less.

Further, the oxyalkylene polymer ( B )
That is, further having a narrow molecular weight distribution, namely the weight average a molecular weight (Mw) / number average molecular weight (Mn) smaller is better drying property of the alkyd paint is painted the ratio of the low molecular weight component is small pressurized et al 1. 5 or less are used .

Such an oxyalkylene polymer
As specific examples of (B) and the oxyalkylene polymer (C), for example, the number average molecular weight is 4000 or more, and in the case of the oxyalkylene polymer (B), the molecular weight distribution is as narrow as 1.5 or less . Oxyalkylene polymer
In the case of (C), the content having a molecular weight of 1,000 or less is 10%.
Polyoxypropylene glycol as small as the following, a part of the hydroxyl group of the polyoxypropylene glycol is an alkyloxy group, an alkylphenyloxy group, an alkenyloxy group, those having a hydroxyl group blocked by a hydrocarbon group such as an allyloxy group, Examples include, but are not limited to, a hydrocarbon group such as an alkyl group, an aryl group, or an alkenyl group in which a part of a hydroxyl group is blocked through a bond such as a urethane bond, an ester bond, a urea bond, or a carbonate bond. Not something.

The oxyalkylene polymer (D) is a polymer having substantially no hydroxyl groups.

When the oxyalkylene-based polymer (D) substantially contains a hydroxyl group, generally, when an alkyd-based coating is applied to a cured product, the drying property of the coating tends to deteriorate.

Usually, an oxyalkylene polymer is produced by ionic polymerization of an alkylene oxide.
It usually has a hydroxyl group, especially a terminal hydroxyl group. There are various methods for obtaining an oxyalkylene polymer (D) from an oxyalkylene polymer having a hydroxyl group. For example, by introducing a substituted or unsubstituted hydrocarbon group using the reactivity of a hydroxyl group, 90 mol% or more, preferably 95 mol% or more of the hydroxyl group is converted to a group other than the hydroxyl group. Examples of such a polymer in which a hydroxyl group is converted to another group include the oxyalkylene-based polymer.
(B) or an oxyalkylene polymer having a terminal hydroxyl group as a specific example of the oxyalkylene polymer (C), having a molecular weight distribution of 1.5 or less or a molecular weight of 1 or less.
Unlimited terminal hydroxyl group with a content of 000 or less and 10% or less
Oxyalkylene polymer of the ether bond, urethane bond, ester bond, urea bond, through a bond such as a carbonate bond, methyl group, ethyl group, propyl group, chloromethyl group, benzyl group, alkyl group such as glycidyl group, A substituted or unsubstituted hydrocarbon group such as an aryl group such as a phenyl group, a toluyl group, and a chlorophenyl group; an alkenyl group such as a vinyl group and an allyl group;
Oxyalkylene polymer it is blocked with a hydrocarbon group ₁ -C ₄₀ and the like. However, the present invention is not limited thereto, and other oxyalkylene-based polymers may be used as long as they do not substantially contain a hydroxyl group.

Among the oxyalkylene polymers (D), oxyalkylene polymers containing an alkenyl group are convenient for use because they can be used as raw materials for the oxyalkylene polymer (A).

Although the molecular weight of the oxyalkylene polymer (D) is not particularly limited, it is usually preferably about 1,000 or more. Generally, an oxyalkylene polymer (D)
When the number average molecular weight of is larger, the coatability of the alkyd paint is further improved. For example, when the molecular weight is 4000 or more, a desirable coatability of the alkyd paint can be obtained. Furthermore, the molecular weight is 4500 or more, especially 5000-1
Preferably it is 5000. Also, the oxyalkylene polymer also content and molecular weight distribution of the number average molecular weight of 1,000 or less components of the oxyalkylene polymer (D)
The description in the case of (B) or the oxyalkylene polymer (C) can be similarly applied, and the component having a number average molecular weight of 1,000 or less is preferably low, and the Mw / Mn is preferably low.

The oxyalkylene polymer (B) and
The oxyalkylene polymer (C) may be used alone or in combination of two or more. The oxyalkylene polymer (B) and the oxyalkylene polymer
(C) may be blended as a solvent during the production of the oxyalkylene polymer (A).

The oxyalkylene polymer (B) and
The amount of the oxyalkylene polymer (C) to be used is preferably 10 to 500 parts, more preferably 20 to 200 parts, per 100 parts (parts by weight, hereinafter the same) of the oxyalkylene polymer (A).
Parts are more preferred. If the amount is less than 10 parts, the plasticizing effect is small, and it is not practical in terms of lowering the elastic modulus and increasing the elongation of the cured product, and if it exceeds 500 parts, the curing tends to be slow.

The composition of the present invention may be used by adding a curing accelerator, a filler, and other additives as necessary.

The curing accelerators that can be used in the present invention include:
Examples thereof include organic tin compounds, acidic phosphates, reaction products of acidic phosphates with amines, saturated or unsaturated polycarboxylic acids or acid anhydrides thereof, organic titanate compounds, organic aluminum compounds, organic zirconium compounds, and the like. Can be

Specific examples of the organotin compound include dibutyltin dilaurate, dioctyltin dimaleate, dibutyltin phthalate, tin octylate, dibutyltin methoxide and the like.

The acidic phosphoric acid ester is

[0065]

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A phosphate ester containing a moiety,
For example

[0067]

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(Wherein d represents 1 or 2, and R represents an organic residue).

[0069]

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And the like.

Examples of the organic titanate compound include titanates such as tetrabutyl titanate, tetraisopropyl titanate and triethanolamine titanate.

When a curing accelerator is used, the amount of the curing accelerator is 0.1 to 100 parts of the oxyalkylene polymer (A).
1-20 parts are preferred.

Examples of the filler include heavy calcium carbonate, light calcium carbonate, colloidal calcium carbonate,
Examples include kaolin, talc, silica, titanium oxide, aluminum silicate, magnesium oxide, zinc oxide, carbon black and the like.

Examples of the other additives include an anti-sagging agent such as hydrogenated castor oil and organic bentonite, a coloring agent, an anti-aging agent and the like.

In the composition of the present invention, a low-molecular-weight plasticizer such as dioctyl phthalate may be used in combination as long as the effects of the present invention are achieved.

The composition of the present invention as described above comprises an adhesive,
It can be usefully used as a paint, a coating film waterproofing agent, a sealing material, a molding material, a cast rubber material, a foam material, and the like.

For example, when applied as a building sealing agent, usually 10 to 300 parts of an inorganic filler such as calcium carbonate, talc, kaolin, etc. are added to 100 parts of the oxyalkylene polymer (A), and further necessary. Accordingly, after adding an appropriate amount of pigments such as titanium oxide and carbon black, ultraviolet absorbers, antioxidants such as radical chain inhibitors, drying oils, and air drying compounds such as synthetic drying oils,
By kneading with a kneader or a paint roll and kneading it uniformly and exposing it to moisture in the air, it quickly cures, for example, in about one hour to several days, and exhibits good weather resistance, transparency, and tensile elongation. A rubber elastic body is obtained.

When applied as a paint, it cures in the same manner as described above, and gives a cured product having high tensile elongation and weather resistance, and is excellent as a highly elastic paint for construction, a primer for concrete structures, a waterproofing agent and the like. Show characteristics.

Further, when applied as a coating film waterproofing agent, the balance between breaking strength and elongation is excellent, and the durability and water resistance are good, so that deterioration such as blistering and peeling is improved as compared with the existing technology. You.

Further, when applied as an adhesive, it is used as a structural adhesive as an adhesive having an excellent adhesive strength and, particularly, a well-balanced peel adhesive strength and shear adhesive strength.

When an alkyd paint is applied on a cured product of the composition of the present invention which can be used for such various applications, it is necessary to apply the alkyd paint after the composition is almost completely cured before applying the cured product. Oxyalkylene-based polymer (A) with a coating film, which is easy to apply because it can be applied on an improved material
Although it is preferable from the viewpoint that there is no stop of the supply of water necessary for curing the composition, the composition can be painted if the composition is in a tack-free state or a surface layer is solidified.

The alkyd paints are not particularly limited, and include polybasic acids (phthalic anhydride, maleic anhydride, etc.) and polyhydric alcohols (glycerin, pentaerythritol,
So-called oil-modified alkyd resins in which condensates with ethylene glycol, trimethylolethane, etc. are modified with fatty oils or fatty acids (linseed oil, soybean oil, castor oil, safflower oil, etc.), or alkyd resins in various resins or vinyl A coating containing a modified alkyd resin modified by monomers etc. as a main element of coating film formation.Alkyd resin varnish or alkyd resin enamel used for coating for vehicles, aircraft, industrial use, etc. Alkyd resin blend paint (also called synthetic resin blend paint) used for painting for railway bridges, ships, etc., and alkyd resin base paint used as base paint for automobiles, machinery, electrical products, furniture, etc. It may be in a form. Particularly, the effect is remarkable in a long oil alkyd paint having a large amount of drying oil used for general purposes.

Conventionally, when a cured alkyd-based paint using the oxyalkylene-based polymer (A) in combination with a conventional low-molecular-weight plasticizer is applied, drying of the paint is greatly delayed, and even after about one month, stickiness remains. In the case of applying an alkyd paint to the cured product, it has been said that the alkyd paint cannot be substantially used unless a paint (primer) other than the alkyd paint is applied first and then applied. By using the composition of the present invention, an ordinary alkyd-based coating film can be formed on a cured product of the composition containing the oxyalkylene-based polymer (A) and the plasticizer by an ordinary method.

[0084]

EXAMPLES Next, the composition of the present invention will be specifically described based on examples.

Synthesis Example 1 800 g of an oxypropylene-based polymer having an average molecular weight of about 8,000 in which an allyl ether group was introduced at 97% of all terminals was placed in a pressure-resistant reaction vessel equipped with a stirrer, and methyldimethoxysilane 1 was added.
9 g were added. Then, a chloroplatinic acid catalyst solution (H ₂ PtC
1 ・ 6H ₂ O in isopropyl alcohol 1
After adding 0.34 ml of a solution dissolved in 8 ml and 160 ml of tetrahydrofuran, the mixture was reacted at 80 ° C. for 6 hours.

The amount of residual hydrosilyl groups in the reaction solution
As a result of quantification by R spectrum analysis, almost no residue remained. When the reactive silicon group was quantified by the NMR method, (CH ₃ O) ₂ Si (C
_{H 3) CH 2 CH 2 CH} 2 O- group oxypropylene polymer having about 1.7 per 1 molecule has been e.

Example 1, Reference Examples 1-4 and Comparative Examples 1
2 As shown in Table 1, a composition prepared by blending the oxypropylene-based polymer (A) obtained in Synthesis Example 1 with components such as the oxyalkylene-based polymer (B) shown in Table 1 was used. A sheet having a thickness of 3 mm was prepared and cured at room temperature for one day, and then alkyd paint (trade name: Rock Coat, manufactured by Rock Paint Co., Ltd.) was applied. The curability of Ai was examined by touch. Table 1 shows the results.

In Table 1, columns such as oxyalkylene-based polymer (B) indicate Mn = 7500 and Mw / Mn = 1.
8. An oxypropylene polymer having an allyl ether group at both ends and containing no hydroxyl group has Mn = 5200, M
w / Mn = 1.6, oxypropylene polymer having allyl ether groups at both ends, Mn = 5100, Mw / Mn =
1.1, the ratio of components having a MW of 1,000 or less is 4%, and the oxypropylene polymer having a hydroxyl group at the end is Mn = 400.
0, Mw / Mn = 1.1, both ends are oxypropylene polymers having an allyl ether group. Is Mn = 2400,
It is an oxypropylene polymer having Mw / Mn = 1.1 and both terminals having an allyl ether group.

The numbers in the column of evaluation result indicate the curability of the alkyd paint, 5 indicates that the applied paint is completely cured, 4 indicates that the applied paint is cured, but that the surface is slightly sticky, 3 indicates that the paint is slightly applied to the fingertip when the finger is applied to the application surface, 2 indicates that the paint is applied to the fingertip when the finger is applied to the application surface, but 1 indicates that the applied paint is thickened 0 indicates that the applied paint has no change (uncured).

[0090]

[Table 1]

From the results shown in Table 1, when oxypropylene having a terminal hydroxyl group blocked is used as in Reference Examples 1, 2, 3, and 4, it has a conventional low molecular weight plasticizer (dioctyl phthalate) and a hydroxyl group. It is apparent that the alkyd paint has excellent curability as compared with the case where the oxypropylene polymer having a low molecular weight (Mn = 3000) is used.

Also, when the oxypropylene polymer having a molecular weight of 4000 or more is used as in Example 1, the alkyd paint has excellent curability as compared with the case where a low molecular weight oxypropylene polymer is used. Is evident.

[0093]

The oxyalkylene polymer (A) and the oxyalkylene polymer (B) or the oxyalkylene polymer
The cured product obtained from the composition of the present invention containing the polymer (C) can be coated with an alkyd paint under ordinary conditions and dried to form a good alkyd paint film. can do.

──────────────────────────────────────────────────続 き Continued on front page (58) Field surveyed (Int.Cl. ⁷ , DB name) C08L 1/00-101/14

Claims (2)

(57) [Claims] 1. An oxyalkylene polymer having (A) a hydroxyl group or a hydrolyzable group bonded to a silicon atom and having at least one silicon-containing group which can be crosslinked by forming a siloxane bond; and (B) Weight average molecular weight (Mw) / number average molecular weight (Mn)
A curable composition comprising a hydroxyl group-containing oxyalkylene polymer having a number average molecular weight of not more than 1.5 and a number average molecular weight of not less than 4000. (A) a hydroxyl group bonded to a silicon atom or
Has a hydrolyzable group and forms a siloxane bond
Having at least one silicon-containing group that can be crosslinked by
The oxyalkylene polymer and ( C) a hydroxyl group having a number average molecular weight of 4000 or more in which the proportion of the component having a molecular weight of 1000 or less is 10% by weight or less .
Curable composition containing an oxyalkylene polymer .