JPH0841344A - Primer and method for producing the same - Google Patents

Abstract

(57) [Summary] [Structure] (A) An organopoly having an R / Si ratio of 0.9 to 1.55, a phenyl group / R ratio of 20 to 80%, and at least two hydroxyl groups bonded to silicon atoms. Siloxane; (B) an organosilicon compound having at least one amino group bonded to a carbon atom and at least two alkoxyl groups bonded to a silicon atom in a molecule; (C) an organotitanium compound and / or an organozirconium compound; And (D) a primer comprising an organic solvent; and at least two components of (A) to (D) or (A) to (C) and (D) are heat treated at 40 ° C. or higher. And a method for producing the above primer. [Effect] An effective primer can be obtained for the electrodeposition coated surface of a building member such as aluminum.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a primer composition and a method for producing the same. More specifically, it is dried at room temperature to form a strong and transparent coating on the surface of an adherend such as electrodeposition-coated aluminum, which imparts excellent adhesion between the adherend and silicone rubber. The present invention relates to a primer composition and a method for producing the same.

[0002]

2. Description of the Related Art One of the uses of room temperature curable silicone rubbers is for sealing structures. In order to bond the adherend to the room temperature curable silicone rubber, the method of treating the adherend with various primers in advance and then applying the room temperature curable silicone rubber to bond the adherend is very common. Has been done. Conventionally, secondary electrolytic colored aluminum has been widely used as an exterior material for buildings in terms of weight reduction, colorability, weather resistance and the like. However, in recent years, matte electrodeposition coating such as acrylic resin has been put into practical use, and aluminum that has been electrodeposition coated has been widely used as an exterior material for buildings. Electrodeposition coating has good coating efficiency, a uniform coating film is obtained, it is cheaper than electrostatic coating, and it can be automated, so it is suitable for mass production, and compared with secondary electrolytic colored aluminum. It has many advantages such as good corrosion resistance. On the other hand, compared with conventional secondary electrolytically colored aluminum, urethane resin coated aluminum, etc., it is extremely difficult to bond silicone rubber, and sufficient adhesive force can be obtained even with various types of primers. There wasn't.

Since there is no primer having good adhesiveness on the surface of the adherend made of these various kinds of electrodeposition-coated aluminum, conventionally, the electrodeposition-coated surface is polished by using a nylon scrubbing brush and the like. After roughening, it is often the case that a primer is used to impart an adhesive force, and the work is extremely complicated. Therefore, there has been a strong demand for the development of a primer that exhibits good adhesion to all adherends used, including electrodeposition-coated aluminum.

In order to achieve such a demand, a composition comprising a polyorganosiloxane containing a hydroxyl group or an alkoxyl group, an amino group-containing silane and a titanate ester (JP-A-2-21888) has been proposed. However, although this primer composition exhibits good adhesiveness to urethane resin-based or fluororesin-based coated aluminum, it may take a long time depending on the adherend such as acrylic resin-based electrodeposition coated aluminum. ,
There is a problem that peeling occurs from the interface when exposed to water or the like so as to be immersed or in a state where tensile restraint stress acts during immersion.

A composition comprising an organic silicon compound, a titanic acid ester, an acid and an organic solvent (JP-A-4-57).
870). However, this primer composition lacks in adhesion stability, and since it contains an acid as a component, it may corrode the surface depending on the adherend.

The primer composition containing a polyorganosiloxane having a hydroxyl group or an alkoxyl group, an amino group-containing alkoxysilane, a mercapto group-containing alkoxysilane, and an organic titanium compound and / or an organic zirconium compound was previously prepared by one of the present inventors. (Japanese Patent Laid-Open No. 6-128553) has been proposed. This composition exhibits excellent adhesiveness as a primer for adhering silicone rubber to various adherends such as painted metal and secondary electrolytically colored aluminum, but it is sufficient for matte electrodeposited aluminum. Good adhesiveness is not obtained.

[0007]

SUMMARY OF THE INVENTION The present invention has been made to solve the above-mentioned problems, and in recent years, acrylic electrodeposition, which has been widely used as a coating for aluminum-based building members, has been proposed. It is an object of the present invention to provide a primer composition effective for a painted surface and a method for producing the same.

[0008]

Means for Solving the Problems As a result of intensive studies to achieve the above object, the present inventors have found that a polyorganosiloxane having a hydroxyl group and a phenyl group bonded to a silicon atom in a molecule has a carbon atom. An organosilicon compound having a functional amino group and a silicon functional alkoxyl group,
The inventors have found that the above object can be achieved by a primer composition obtained by heat-treating a composition containing an organic titanium compound and / or an organic zirconium compound, and an organic solvent, and completed the present invention.

That is, in the present invention, (A) in a molecule, R (R represents a monovalent substituted or unsubstituted hydrocarbon group) bonded to a silicon atom is 0.9 per one silicon atom. To 1.55, the proportion of phenyl groups in R is 20 to 80%, and 100 parts by weight of polyorganosiloxane having at least two hydroxyl groups bonded to silicon atoms in the molecule; (B) carbon atom An organosilicon compound having at least one amino group bonded to the molecule in the molecule and at least two alkoxyl groups bonded to the silicon atom in the molecule
To 100 parts by weight; (C) 0.1 to 100 parts by weight of an organotitanium compound and / or an organic zirconium compound; and (D) 10 to 5,000 parts by weight of an organic solvent. The present invention also relates to a method for producing a primer, which comprises heat-treating a composition containing all components at 40 ° C. or higher when preparing the above primer. Furthermore, in the present invention, a composition comprising any two components of the components (A) to (C) and the component (D) is prepared, heat treated at 40 ° C. or higher, and then the components (A) to (C). The present invention relates to a method for producing the above-mentioned primer, which is characterized by blending the remaining components.

The polyorganosiloxane of component (A) used in the present invention basically comprises R ₃ SiO _1/2 units and R ₂
It is a resinous or liquid reactive polyorganosiloxane having one or more kinds of SiO unit, RSiO _3/2 unit and SiO ₂ unit (where R is as described above) as a constituent unit. Ratio of R to Si atom, that is, R
The / Si ratio is 0.7 to 1.55, preferably 1.0 to 1.5, from the viewpoint of film forming property, adhesive property and easiness of synthesis. If R / Si is less than 0.7, it is difficult to synthesize and storage stability is poor. Further, if it is less than 1.0, extreme thickening or gelation tends to occur during the heat treatment described later. When R / Si exceeds 1.55, the curing rate is insufficient and the obtained primer does not show sufficient adhesiveness depending on the adherend.

Further, the characteristic feature of the polyorganosiloxane of the component (A) is that 20 to 80 in the above R is used.
%, Preferably 30 to 70% is a phenyl group, which makes it possible to obtain a primer which is stable and has sufficient adhesiveness to a wide range of adherends including electrodeposition coated aluminum. In particular, the effect of improving the adhesiveness and stability by the heat treatment described below is great. When the proportion of the phenyl group in R is less than 20%, the reactivity of the hydroxyl group, which is a functional group bonded to the silicon atom, is high, and the components (B) and (C) are
The storage stability after blending is insufficient, and particularly when the heat treatment described below is performed, extreme thickening or gelation is likely to occur. On the other hand, when the phenyl group exceeds 80%, it is difficult to synthesize and the adhesiveness of the primer decreases. Further, in the case of having only an alkoxyl group as the functional group, the adherend cannot obtain sufficient adhesiveness to the electrodeposition-coated aluminum even after the heat treatment.

As the component (A), two or more kinds of resinous polyorganosiloxanes which are compatible with each other can be mixed and used. In this case, the above R / Si ratio and the proportion of phenyl groups in R apply for the whole of the component (A) which is a mixture.

As R other than a phenyl group, an alkyl group such as methyl, ethyl, propyl, butyl, pentyl, hexyl and decyl; a cycloalkyl group such as cyclohexyl; 2-phenylethyl, 2-phenylpropyl and the like. Aralkyl groups; alkenyl groups such as vinyl and allyl; and chloromethyl, 3-chloropropyl,
Various monovalent substituted or unsubstituted hydrocarbon groups such as substituted hydrocarbons such as 3,3,3-trifluoropropyl and 3-methoxypropyl are exemplified, and among them, alkyl such as methyl, ethyl and propyl. Groups; and haloalkyl groups such as chloromethyl, 3,3,3-trifluoropropyl. In particular, from the viewpoint of easy synthesis, good adhesiveness, and stability, the most preferable resinous polymer is that R is a methyl group and a phenyl group, and the basic unit is R ₂ SiO unit and RSiO
It is composed of _3/2 units. The method for producing such a resinous polymer is known to those skilled in the art. This resinous polymer is preferably used in the state of a solution dissolved in various organic solvents, for example, aromatic hydrocarbon solvents such as benzene, toluene and xylene.

Further, in order to give a primer having both excellent adhesiveness and stability, especially by heat treatment, the resinous polyorganosiloxane of the component (A) is directly bonded to a silicon atom as a silicon functional group. It is necessary to have at least two hydroxyl groups in one molecule.

The organosilicon compound as the component (B) used in the present invention contributes as an adhesion improver. Examples of such organosilicon compounds include 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, N- (2-aminoethyl) -3-aminopropyltrimethoxysilane, and N- (2-aminoethyl). −
3-aminopropyltriethoxysilane, 4-aminobutyltrimethoxysilane, 3-aminopropylmethyldimethoxysilane, 3-aminopropylmethyldiethoxysilane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, etc. Examples of amino-based silane coupling agents, and partial hydrolysis-condensation products thereof,
It may be used alone or in combination of two or more kinds.
Since it is easily available and has a great effect of improving the adhesiveness, N-
(2-Aminoethyl) -3-aminopropyltrimethoxysilane is preferred.

The blending amount of the component (B) is 100 parts of the component (A).
0.1 to 100 parts by weight, preferably 1 to 100 parts by weight
It is in the range of 20 parts by weight. If the amount is less than 0.1 parts by weight, the adhesiveness is not sufficient. However, both are not preferable.

The organotitanium compound and / or organozirconium compound of the component (C) used in the present invention act as a curing catalyst, form a strong coating with the polyorganosiloxane (A), and improve the adhesiveness. It is what makes me. Here, the organic titanium compound and the organic zirconium compound are not limited to compounds each having an organic group directly bonded to a titanium or zirconium atom, and an organic group bonded to the metal atom via an oxygen atom or the like, and And / or a compound having an organic group bonded to form a chelate ring with a central metal atom.

Examples of such organic titanium compounds include titanic acid esters and titanium chelate compounds. As the titanic acid ester, tetraethyl titanate,
Tetra-n-propyl titanate, tetraisopropyl titanate, tetra-n-butyl titanate, tetra-sec-butyl titanate, tetra-tert-butyl titanate, tetrahexyl titanate, tetra (2-ethylhexyl titanate) And substituted or unsubstituted alkyl esters such as tetra (2-methoxyethyl) titanate, tetra (2-ethoxyethyl) titanate and tetra (2-butoxyethyl) titanate, and partial hydrolysates thereof. . Examples of titanium chelate compounds include acetylacetonato titanium compounds such as diisopropoxytitanium bis (acetylacetonate) and 1,3-bropandioxytitanium bis (acetylacetonate); and diisopropoxytitanium bis (methylacetoacetate), diisopropoxytitanium bis (acetylacetonate). Propoxy titanium bis (ethyl acetoacetate),
Examples are alkylacetoacetato titanium compounds such as 1,3-propanedioxytitanium bis (ethylacetoacetate) and dibutoxytitanium bis (ethylacetoacetate).

Examples of zirconium compounds include alkoxy zirconium compounds and zirconium chelate compounds. Examples of the alkoxy zirconium compound include tetraisopropoxy zirconium and tetra-
Illustrative are n-butoxy zirconium and their partial hydrolysis products. Examples of the zirconium chelate compound include dibutoxyzirconium bis (acetylacetonate), dipropoxyacetylacetonylstearyloxyzirconium, dibutoxyacetylacetonylstearyloxyzirconium compounds such as zirconium compounds; and dibutoxyzirconium bis (ethylacetate). Alkyl acetoacetato zirconium compounds such as acetate) are exemplified.

Organotitanium compounds are preferred because they provide an excellent curing rate as a catalyst and an excellent adhesion to the primer. Further, in order to impart excellent adhesiveness and storage stability to the primer by the heat treatment described below, it is preferable to have at least one alkoxyl group bonded to a titanium atom or a zirconium atom in the molecule.

The blending amount of the component (C) is 100 parts of the component (A).
0.1 to 100 parts by weight, preferably 1 to 2 parts by weight
It is in the range of 0 parts by weight. If the amount is less than 0.1 part by weight, the film forming property and the adhesive property are not sufficient, and if the amount exceeds 100 parts by weight, the strength of the formed film is lowered and the wettability to an adherend is unfavorable.

The organic solvent of the component (D) used in the present invention has a solubility in the components (A) to (C), a boiling point suitable for heat-treating the composition, and a deposition as a primer during the coating operation. It is selected in consideration of the wettability to the body and the evaporation property. Examples of such organic solvents include aromatic hydrocarbons such as benzene, toluene, xylene, ethylbenzene and isopropylbenzene; aliphatic hydrocarbons such as n-hexane, n-heptane and cyclohexane; trichloroethylene and tetrachloroethylene. Halogenated hydrocarbons; ethers such as tetrahydrofuran; alcohols such as ethanol, isopropanol, butanol; ether alcohols such as 2-methoxyethanol, 2-ethoxyethanol, 2-butoxyethanol; acetone, methyl ethyl ketone Such ketones are exemplified. These organic solvents are used alone or as a mixed solvent of two or more kinds. The blending amount of the component (D) is 10 to 5,000 parts by weight, preferably 1,000 to 100 parts by weight of the component (A), because a stable composition is obtained during the heat treatment.
It is in the range of 2,000 parts by weight. Below 10 parts by weight,
When each component is blended, gelation or precipitation may occur, and a composition suitable for coating operation cannot be obtained. On the other hand, when the amount exceeds 5,000 parts by weight, the ratio of the active ingredient decreases and stable adhesiveness cannot be obtained.

The primer of the present invention comprises the above-mentioned component (A).
~ (D) is included, but according to the finding of the present inventors, when the primer is prepared, a composition containing all of the above components is heat treated or (A) ~
It is preferable to heat-treat a composition comprising any two components of (C) and (D), and then blend the remaining components of (A) to (C). As a result, the adhesion to electrodeposition-coated aluminum, especially after immersion in hot water, can be further improved. It is particularly preferable that the heat treatment is performed on the composition containing the four components (A) to (D) because it has a great effect of improving the adhesiveness of the primer. The heating temperature is 40 ° C. or higher at atmospheric pressure, more preferably 50 ° C. or higher, and is preferably near or below the boiling point of the component (D) used. The heat treatment may be performed, for example, in a reflux state of the component (D). The heating time can be arbitrarily set to 1 hour or more. It is also possible to raise the boiling point of the component (D) to be used and increase the heating temperature by applying pressure.

By such heat treatment, a condensation reaction between the hydroxyl group of the component (A) and the alkoxyl group of the component (B) and / or the component (C), which have been subjected to the heat treatment, occurs,
Since a cocondensate having a functional group left is obtained, the stability during storage is increased. At the same time, a polyorganosiloxane that increases the molecular weight by partial condensation of the component (A) with each other by hydroxyl groups and forms a cured coating film having adhesiveness in a shorter time after application is formed. As a result, it is possible to obtain a primer which is excellent in adhesiveness and does not cause thickening, gelation, precipitation or the like over time and is excellent in storage stability. When two or more kinds of cocondensates of the above-mentioned components (A), (B) and (C) are formed, the amount thereof in the primer is (A), (B) of each starting material. ) And / or (C)
It is included in the compounding amount of.

If necessary, a part of the organic solvent which is the component (D) is extracted by distillation during the heat treatment, or the organic solvent used as the component (D) after the heat treatment,
Alternatively, different kinds of organic solvents may be blended to prepare a viscosity suitable for the primer coating operation.

In the present invention, a carbon-functional organosilicon compound other than the component (B) may be added to the composition before heat treatment or the primer after heat treatment, if necessary. Examples of such organosilicon compounds include 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, and 3-mercaptopropyltrimethoxysilane.

[0027]

EFFECTS OF THE INVENTION The primer of the present invention has excellent storage stability and air-drying property, and is intended to bond a room temperature curable silicone rubber to various adherends that are in contact with the curing process, firmly and with good durability. Used for pretreatment of the adherend.

Pretreatment of an electrodeposited aluminum substrate with the primer of the present invention allows the room temperature curable silicone rubber to adhere firmly and with good durability, and is therefore suitable as a primer for sealing work in construction. In particular, when the adherend is electrodeposited aluminum, the effect is greater than that of a conventional primer, and it is particularly suitable as a primer when a low modulus silicone rubber is used as a sealing material.

[0029]

EXAMPLES The present invention will be described in more detail with reference to Examples and Comparative Examples. The present invention is not limited to these examples. In the examples and comparative examples,
All parts mean parts by weight. The following abbreviations are used in the table. M _50: 50% elongation at a stress _{^{(kgf / cm 2) T max}} : maximum stress at break (kgf / cm ²⁾ E: Maximum elongation (%) CF: cohesive failure rate (%)

Examples 1 and 2, Comparative Examples 1 and 2 34 mol% CH ₃ SiO _3/2 units, 26 mol% (CH ₃ ) ₂ SiO units and 40 mol% (C ₆ H ₅ ) SiO _3/2 units. 100 parts of a 60% xylene solution (A-1) of a resinous polymer having a ratio of a hydrocarbon group bonded to a silicon atom to a hydroxyl group of 1 to 0.7 (the same applies hereinafter by infrared absorption spectrum analysis). , N- (2-aminoethyl) -3
-Aminopropyltrimethoxysilane 11.2 parts, tetra-n-butyl titanate 2.72 parts and toluene 96
0 parts were mixed by stirring and further heated and stirred at 70 ° C. for 2 hours to obtain the primer of Example 1. Example 2
As the above, a primer having the same composition as in Example 1 and not subjected to heat treatment was prepared. Furthermore, as Comparative Example 1, A-1
Instead of CH ₃ SiO _3/2 units 74 mol% and (CH ₃ ).
₂ SiO _3/2 unit _{consisting of} 26 mol%, except that a 60% xylene solution (A-2) of a resinous polymer having a ratio of methyl groups bonded to silicon atoms to hydroxyl groups of 1: 0.4 was used. A primer having the same composition as in Example 1 was heat-treated at 70 ° C. for 2 hours to obtain a primer. As Comparative Example 2,
A primer having the same composition as in Comparative Example 1 but not subjected to heat treatment was prepared.

These primers were applied by brush to various test panels shown in Table 1. After drying at room temperature for 30 minutes, Aminoxy type low modulus type silicone sealing material Tosseal 361 (trade name, manufactured by Toshiba Silicone Co., Ltd.) is applied to form a type 2 test specimen for a tensile adhesion test specified in JIS A5758. It was left to cure in the air at room temperature for 7 days and then at 50 ° C. for 7 days. Normal,
Tensile tests were conducted at a tensile speed of 50 mm / min for each of the test pieces immersed in warm water of 50 ° C. for 7 days. Table 1 shows the appearance and the results of the tensile adhesion test under normal conditions and after immersion in warm water.

[0032]

[Table 1]

Examples 3 to 7 and Comparative Examples 3 to 7 60% xylene solution (A-1) of the polyorganosiloxane resinous polymer used in Example 1 or CH ₃ SiO 2.
_3/2 unit 37 mol%, (CH ₃ ) ₂ SiO unit 5 mol%,
41 mol% C ₆ H ₅ SiO _3/2 units and (C ₆ H ₅ ) ₂
60% xylene solution (A-3) of a resinous polymer consisting of 17 mol% of SiO unit and having a ratio of hydrocarbon groups bonded to silicon atoms to hydroxyl groups of 1: 1.25, and the amounts shown in Table 2. Stir each component of room temperature at room temperature to mix, then 70 ℃
The mixture was heated and stirred for 10 hours to obtain a primer.

[0034]

[Table 2]

The appearance of each of these primers was observed. Immediately after the preparation, each of these primers was treated on a matte electrodeposition coated aluminum (Company T) to prepare Example 1
A type 2 specimen was prepared and cured in the same manner as in. A tensile adhesion test was performed on a normal type and a type 2 test piece immersed in warm water of 50 ° C. for 7 days at a pulling speed of 50 mm / min. Table 3 shows the results.

[0036]

[Table 3]

On the other hand, in order to evaluate storage stability, 50 ° C.
The appearance of the primers after the accelerated test for 14 days was similarly observed in the constant temperature bath of No. 3 and the tensile adhesion test by the type 2 test piece was performed for the primers of Examples 3 to 7 in the same manner as after the primer preparation. went. The primer of Comparative Example 3 gelled during the accelerated test and was unprocessable. The results are shown in Table 4.

[0038]

[Table 4]

Examples 8 to 16 As in Example 1, 60% xylene solutions (A-1) and N- (2) of the polyorganosiloxane resinous polymer used in Example 1 in the amounts shown in Table 5 were used. -Aminoethyl) -3-aminopropyltrimethoxysilane, tetra-n-titanate
Butyl and toluene were mixed by stirring, and
The mixture was heated and stirred under the conditions shown in to obtain primers (Examples 8 to 12), respectively. Further, three components other than the 60% xylene solution (A-1) of the polyorganosiloxane resinous polymer are stirred and mixed, and after heating and stirring at 70 ° C. for 2 hours,
What added 60% xylene solution (A-1) of polyorganosiloxane resinous polymer (Example 13), N-
Three components other than (2-aminoethyl) -3-aminopropyltrimethoxysilane were stirred and mixed, and the mixture was stirred at 70 ° C. for 2 hours.
After heating and stirring for an hour, N- (2-aminoethyl) -3-
Aminopropyltrimethoxysilane was added (Example 14) and three components other than tetra-n-butyl titanate were stirred and mixed, and the mixture was heated and stirred at 70 ° C. for 2 hours, and then tetra-n titanate was added. -Butyl was added (Example 15). Further, as Example 16, a product was prepared in which the above components were simply mixed uniformly and not subjected to heat treatment.

[0040]

[Table 5]

Each of the primers obtained under the conditions shown in Table 5 was treated with a matte electrodeposition coated aluminum (S company) to prepare a type 2 test piece in the same manner as in Example 1 and curing. went. Tensile tests were performed on the normal test pieces and the test pieces immersed in warm water of 50 ° C. for 7 days at a pulling speed of 50 mm / min. Table 6 shows the results.

[0042]

[Table 6]

Examples 17, 18 and Comparative Examples 8-11 Table 7 shows resinous polymers having the siloxane units shown in Table 7 and the ratio of silicon atom-bonded hydrocarbon groups to hydroxyl groups or alkoxyl groups. The amounts of the respective components shown in Table 7 were stirred and mixed at room temperature with a solvent and a solution having a concentration, and further stirred at 50 ° C. for 8 hours to obtain primers.

These primers were treated on a matte electrodeposition coated aluminum (Company S) to give 2 as in Example 1.
A shaped specimen was prepared and cured. This type 2 specimen
A tensile adhesion test was performed at a tensile rate of 50 mm / min for each of the normal state and the one immersed in warm water at 50 ° C. for 7 days. The results are shown in Table 7.

[0045]

[Table 7]

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Internal reference number FI technical display location C09D 185/00 PMW

Claims (3)

[Claims] 1. In (A) molecule, R (R represents a monovalent substituted or unsubstituted hydrocarbon group) bonded to a silicon atom is 0.9 to 1.55 per silicon atom. The number of phenyl groups in R is 20 to 80%,
100 parts by weight of polyorganosiloxane having at least two hydroxyl groups bonded to silicon atoms in the molecule; (B) at least one amino group bonded to carbon atoms in the molecule, and an alkoxyl group bonded to silicon atoms in the molecule 0.1 having at least two organic silicon compounds
To 100 parts by weight; (C) 0.1 to 100 parts by weight of an organic titanium compound and / or an organic zirconium compound; and (D) 10 to 5,000 parts by weight of an organic solvent, or (A) and (B) above. And (C) a mutual condensate of two or more kinds. 2. In the molecule (A), R (R represents a monovalent substituted or unsubstituted hydrocarbon group) bonded to a silicon atom is 0.9 to 1.55 with respect to one silicon atom in the molecule. The number of phenyl groups in R is 20 to 80%,
100 parts by weight of polyorganosiloxane having at least two hydroxyl groups bonded to silicon atoms in the molecule; (B) at least one amino group bonded to carbon atoms in the molecule, and an alkoxyl group bonded to silicon atoms in the molecule 0.1 having at least two organic silicon compounds
˜100 parts by weight; (C) a composition containing 0.1 to 100 parts by weight of an organic titanium compound and / or an organic zirconium compound; and (D) 10 to 5,000 parts by weight of a organic solvent, and heat-treated at 40 ° C. or higher. A method for producing a primer, comprising: 3. A composition comprising any two components (A) to (C) according to claim 2 and component (D) at 40 ° C.
A method for producing a primer, comprising the above heat treatment, and then blending the remaining components of the components (A) to (C).