JP2003201408A - Curable organic resin composition - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a curable organic resin composition having excellent moldability, curable without deteriorating curability of the curable organic resin itself during curing and having characteristics such as excellent adhesion to a substrate such as a metal. <P>SOLUTION: The curable organic resin composition comprises (A) 100 pts.wt. of the curable organic resin and (B) 0.01-100 pts.wt. of a thiocyanate group- containing organoalkoxysilane or an isothiocyanate group-containing organoalkoxysilane represented by general formula (I) X-R<SP>1</SP>-Si(OR<SP>2</SP>)<SB>n</SB>R<SP>3</SP><SB>3-n</SB>(1) (wherein, X is NCS or SCN; R<SP>1</SP>is an alkylene group or an alkyleneoxyalkylene group; R<SP>2</SP>and R<SP>3</SP>are each monovalent hydrocarbon group; and n is 1, 2 or 3). <P>COPYRIGHT: (C)2003,JPO

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a curable organic resin composition.
The present invention relates to a curable organic resin composition having excellent adhesion to a substrate such as metal.

[0002]

2. Description of the Related Art Conventionally, it has been known that when an epoxy group-containing organosilane, an amino group-containing organoalkoxysilane or a mercapto group-containing organoalkoxysilane is blended with an epoxy resin, its adhesiveness is improved. For example, in JP-A-63-309566, an epoxy resin powder coating is prepared by adding γ-glycidoxypropylmethyldiethoxylane, N-phenyl-γ-aminopropyltrimethoxylane, γ-mercaptopropyltrimethoxysilane and the like. A coating composition in which a silane coupling agent is blended to improve its adhesiveness has been proposed. Further, JP-A-2-185584 proposes an adhesive composition in which γ-mercaptopropyltrimethoxysilane is mixed with an epoxy resin. However, the composition containing an epoxy group-containing alkoxysilane does not always have sufficient adhesiveness to a substrate such as a metal and cannot be used depending on the application. Further, the composition containing the amino group-containing organoalkoxysilane or the mercapto group-containing organoalkoxysilane has a problem that the original curability of the epoxy resin is significantly impaired. On the other hand, an organic rubber composition containing a thiocyanato group-containing organoalkoxysilane and the thiocyanato group-containing organoalkoxysilane is known. For example, Japanese Patent Laid-Open No. 4-277
In Japanese Patent No. 534, there is proposed a composition in which thiocyanatopropyltrimethoxysilane is mixed with ethylene propylene diene rubber (EPDM), and this composition has physical properties after vulcanization in the presence of an organic peroxide. It is said that it will be a rubber molded product with little deterioration and a small compression set. Further, JP-A-5-214171 proposes a composition in which thiocyanatopropyltrimethoxysilane is mixed with a vulcanizable organic rubber such as natural rubber (NR), styrene-butadiene rubber (SBR), and EPDM. However, this composition is said to be a rubber molded product with little deterioration in physical properties when vulcanized in the presence of sulfur. However, by blending a thiocyanato group-containing organoalkoxysilane with an organic resin, an organic resin composition in which the moldability of the organic resin and the adhesiveness to a substrate such as a metal with which the organic resin contacts during curing are simultaneously improved The thing is unknown.

[0003]

As a result of diligent efforts, the present inventors have found that the above problems can be solved by blending an epoxy resin with a thiocyanato group-containing organoalkoxysilane. Further, they have found that if a thermosetting organic resin such as a phenol resin or an imide resin is blended with a thiocyanato group-containing organoalkoxysilane, its adhesiveness is improved, and the present invention has been accomplished. That is, the object of the present invention is to
Provided is a curable organic resin composition which is excellent in moldability and cures without impairing the curability of the thermosetting organic resin itself upon curing, and has excellent adhesiveness to a substrate such as a metal that contacts during curing. Especially.

[0004]

The present invention provides (A) curability
Organic resin (100 parts by weight) and (B) general formula (1): X-
R¹-Si (OR²)_nR³ _3-n(Where X is NCS-or
Is SCN- and R¹ Is an alkylene group or alkyle
Is an oxyalkylene group, and R²And R³Is monovalent carbonization
It is a hydrogen group, and n is 1, 2 or 3. )
A thiocyanato group-containing organoalkoxysilane or
Organoalkoxysilane containing isothiocyanato group
(0.01 to 100 parts by weight)
And a curable organic resin composition.

[0005]

DESCRIPTION OF THE PREFERRED EMBODIMENTS To explain this, (A) the curable organic resin is liquid or solid at room temperature and
Any organic resin can be used as long as it can be cured by irradiation with high energy rays such as ultraviolet rays, radiation, and electron beams, and the type thereof is not particularly limited, but an organic resin that is cured by heating (thermosetting organic resin) is preferable. . Examples of such curable organic resin include epoxy resin, phenol resin, formaldehyde resin, xylene resin, xylene-formaldehyde resin, ketone-formaldehyde resin, furan resin, urea resin, imide resin, melamine resin, alkyd resin, unsaturated polyester. Examples thereof include resins, aniline resins, sulfone-amide resins and silicone resins. Among these, epoxy resin, phenol resin and imide resin are preferable.

The component (B) is a characteristic component of the composition of the present invention, and functions to improve the moldability of the composition of the present invention and to improve the adhesion to a substrate such as metal. Component (B) has the general ^{formula: X-R 1 -Si (OR} 2) n R 3
_3-n (wherein, X is NCS- or SCN-, R ¹ is an alkylene group or an alkyleneoxyalkylene group, R ² and R ³ are monovalent hydrocarbon groups, and n is 1, 2 or
Or 3. ) Is a thiocyanato group-containing organoalkoxysilane or isothiocyanato group-containing organoalkoxysilane. In the above formula, examples of the alkylene group for R ¹ include a methylene group, an ethylene group, a methylmethylene group, a propylene group, a methylethylene group, and a butylene group. Examples of the alkyleneoxyalkylene group for R ¹ include a methyleneoxymethylene group, a methyleneoxyethylene group, an ethyleneoxyethylene group, and an ethyleneoxypropylene group. Of these, an alkylene group is preferable. Examples of the monovalent hydrocarbon group of R ² and R ³ include an alkyl group such as a methyl group, an ethyl group, a propyl group and an isopropyl group; an alkenyl group such as a vinyl group, an allyl group and butenyl; a phenyl group, a tolyl group, a xylyl group. And aryl groups such as Of these, an alkyl group is preferable. n is 1, 2 or 3, preferably 2 and 3.

The component (B) containing a thiocyanato group
Organoalkoxysilane or isothiocyanato group
The content of organoalkoxysilane is as follows.
An example is a compound. NCS (CH₂)₃Si (OCH₃)₃ NCS (CH₂)₃Si (OCH₂CH₃)₃ NCS (CH₂)₃Si [OCH (CH₃)₂]₃ NCS (CH₂)₃Si [O (CH₂)₂CH₃]₃ NCS (CH₂)₃Si [O (CH₂)₃CH₃]₃ NCSCH₂CH (CH₃) CH₂Si (OCH₃)₃ NCSCH2CH (CH₃) CH₂Si (OCH₂CH₃)
₃ SCN (CH₂)₃Si (OCH₃)₃ SCN (CH₂)₃Si (OCH₂CH₃)₃ SCN (CH₂)₃Si [OCH (CH₃)₂]₃ SCNCH₂CH (CH₃) CH₂Si (OCH₃)₃ SCNCH₂CH (CH₃) CH₂Si (OCH₂CH₃)₃ SCNCH₂CH (CH₃) CH₂Si [OCH (CH₃)
₂]₃ SCNCH₂CH (CH₃) CH₂Si [O (CH₂)₃CH
₃]₃ NCS (CH₂)₃SiCH₃(OCH₃)₂ NCS (CH₂)₃SiCH₃(OCH₂CH₃)₂ NCS (CH₂)₃Si (OC₆H_Five)₃ NCSCH₂CH (CH₃) CH₂SiCH₃(OCH₃)₃ The component (B) is 2 or more kinds even if it is added alone to the component (A).
You may mix the above.

If the blending amount of the component (B) is too small, the adhesiveness to a substrate such as a metal will be lowered, and if it is too large, the mechanical strength will be lowered. Within the range of 01 to 100 parts by weight, preferably
It is in the range of 0.1 to 50 parts by weight.

The composition of the present invention comprises the components (A) and (B) as described above. In addition to these components,
Various additives known to be added to the component (A), for example, a curing agent or a curing accelerator for promoting the curing of the component (A), a filler, a pigment, a heat-resistant agent, a flame retardant,
Antioxidant, photosensitizer, plasticizer or flexibility-imparting agent,
An organic solvent can be added.

Examples of the curing agent or curing accelerator include primary or secondary amino compounds, tertiary amine compounds, carboxylic anhydrides such as phthalic anhydride and tetrahydrophthalic anhydride, imidazole compounds, and phenol novolac. Examples thereof include resins and novolac resin compounds such as cresol novolac resins, organic metal compounds such as aluminum and zirconium, organic phosphorus compounds such as phosphine, boron complex compounds, organic ammonium salts, organic sulfonium salts, and organic peroxides.

It is preferable to add 0.1 to 30 parts by weight of such a curing agent to 100 parts by weight of the component (A). However, when a novolac resin is used as a curing agent for the epoxy resin, it is preferable to mix 10 to 400 parts by weight of the novolac resin with respect to 100 parts by weight of the epoxy resin. Further, the curing accelerator is the component (A) 100
It is preferable to mix 0.01 to 10 parts by weight with respect to parts by weight.

As the filler, glass fiber, asbestos, alumina fiber, ceramic fiber containing alumina and silica as a component, boron fiber, zirconia fiber, silicon carbide fiber, metal fiber, polyester fiber, aramid fiber, nylon fiber, phenol fiber. Fibrous fillers such as natural animal and vegetable fibers; fused silica, precipitated silica, fumed silica, calcined silica, zinc oxide, calcined clay, carbon black, glass beads, alumina, talc, calcium carbonate, clay, aluminum hydroxide, Examples of the granular fillers include barium sulfate, titanium dioxide, aluminum nitride, silicon carbide, magnesium oxide, beryllium oxide, kaolin, mica and zirconia. When the curable organic resin composition is not in the liquid state, such a filler is used as the component (A) 1
10 to 500 parts by weight with respect to 00 parts by weight, preferably 0 to 50 parts by weight when the curable organic resin composition is liquid.

Examples of the plasticizer or the flexibility-imparting agent include higher fatty acid metal salts, ester waxes, silicone oils, silicone oils containing an organic functional group, silicone rubbers, and organic rubbers.

The composition of the present invention comprises the above-mentioned components (A) and (B), and can be easily produced by uniformly mixing the above-mentioned additives, if necessary. Examples of the apparatus for producing the composition of the present invention include a continuous mixing extruder, a Ross mixer, a kneader mixer, and a twin roll. Further, in order to obtain a molded article from the composition of the present invention, a conventionally known method known as a molding method of the component (A), for example, compression molding method, transfer molding method, injection molding method, potting molding method, casting A molding method, a coating method, or the like can be applied.

The composition of the present invention as described above is excellent in moldability and is excellent in adhesiveness to a base material such as a metal which is contacted during curing. Here, examples of the material of the metal base material include copper, nickel, brass, iron, steel, stainless steel, aluminum, duralumin, titanium, and silver, and other base materials include glass, ceramics, stone materials, and semiconductors. It is illustrated.
Taking advantage of such characteristics, the composition of the present invention is, for example,
It can be widely used as a sealing agent, packaging agent, coating agent, adhesive agent, etc. for electric / electronic parts, devices / machines, construction and automobiles.

[0016]

EXAMPLES Hereinafter, the composition of the present invention will be described in detail with reference to Examples. The viscosity in the examples is a value at 25 ° C. Further, the moldability, adhesiveness, and viscosity change rate of the curable organic resin composition were evaluated by the following methods. ○ Moldability The fluidity of the curable organic resin composition under pressure was evaluated by measuring the spiral flow. The spiral flow was measured by a method according to the EMMI standard (EMMI-1-66). ○ Adhesiveness (A) The curable organic resin composition was applied to two nickel plates (length 5c).
m, width 1 cm, thickness 0.5 mm), and compression-molded at a predetermined temperature and a predetermined pressure to produce an adhesion test piece in which a nickel plate and a cured product of the curable organic resin composition are integrated. did. The ends of two nickel plates of this test piece were fixed to jigs of a tensile tester and pulled vertically at a pulling speed of 50 mm / min to separate the cured product of the organic resin composition and the nickel plate. . Then, the fractured state of the fractured surface of the cured product of the curable organic resin composition and the nickel plate was visually observed. The results are expressed as follows. ⊚: Adhesiveness is extremely good (broken in the cured product layer of the curable organic resin. Cohesive failure rate 100%) ○: Adhesiveness is good (partial interfacial peeling. Cohesive failure rate 95
% Or more) x: Poor adhesion (peeled at the interface between the cured product of the curable organic resin and the nickel plate. Cohesive failure rate of 50% or less) Adhesiveness (B) Two curable organic resin compositions were used. (Length 5c
m, width 1 cm, thickness 0.5 mm), and compression-molded at a predetermined temperature and a predetermined pressure to prepare an adhesion test piece in which a nickel plate and a cured product of a curable organic resin are integrated. Further, an adhesion test body in which a copper plate and a cured product of the curable organic resin composition were integrated was prepared in the same manner as above. The end portions of the two metal plates of these test bodies were fixed to jigs of a tensile tester and pulled vertically at a pulling speed of 50 mm / min,
The cured product of the curable organic resin composition and the metal plate were peeled off. The stress required for peeling at this time was measured, and the adhesive force (Kgf / c
m ² ). ○ Viscosity change rate: 23 ° C after the production of the curable organic resin composition
The sample was allowed to stand for 24 hours, and the degree of increase in viscosity was measured and used as the rate of change in viscosity. Viscosity change rate = (viscosity of curable organic resin composition after standing for 24 hours−viscosity of curable organic resin composition immediately after production) × 100 / viscosity of curable organic resin composition immediately after production

[0017]

[Example 1] 35 parts by weight of phenol resin (manufactured by Mitsui Chemicals, Inc .: phenol novolac resin, Milex XLC-3L, softening point 70 ° C, hydroxyl equivalent 170), 3-thiocyanatopropyltrimethoxysilane {NCS (C
H ₂ ) ₃ Si (OCH ₃ ) ₃ } 3 parts by weight, fused silica powder 65
By weight, 4 parts by weight of hexamethylenetetramine and 1 part by weight of carnauba wax were kneaded with a heating roll at 90 ° C. to produce a curable phenol resin composition. The composition was crushed and the crushed product was mixed with two nickel plates (length 5 mm).
cm, width 1 cm, thickness 0.5 mm), temperature 1
Compression molding was performed under the conditions of 75 ° C., pressure of 70 kg / cm ² , and heating time of 3 minutes. Then, it was heated at 180 ° C. for 2 hours to complete the curing, and an adhesion test piece in which the nickel plate and the cured product of the phenol resin composition were integrated was prepared. For this test body, the adhesiveness of the curable organic resin composition to the nickel plate was measured by the method described in the adhesiveness test (A) above,
The results are shown in Table 1.

[0018]

Comparative Example 1 A phenol novolac resin composition was prepared in the same manner as in Example 1 except that 3-glycidoxypropyltrimethoxysilane was used instead of 3-thiocyanatopropyltrimethoxysilane. did. The adhesion of this composition to a nickel plate was measured in the same manner as in Example 1, and the results are also shown in Table 1.

[0019]

Comparative Example 2 A phenol novolac resin composition was produced in the same manner as in Example 1 except that 3-thiocyanatopropyltrimethoxysilane was not added. The adhesion of this composition to a nickel plate was measured in the same manner as in Example 1, and the results are also shown in Table 1.

[0020]

[Table 1]

[0021]

Example 2 CH₃SiO_3/2Unit 40 mol%, C₆H
_Five(CH₃) SiO_2/2Unit 10 mol%, C₆H_FiveSiO_3/2
40 mol% unit, and (C₆H_Five)₂SiO_2/2Unit 10
5% by weight of the hydroxyl group which is composed of mol% and is directly bonded to the silicon atom.
% Methylphenylpolysiloxane resin content 13%
And Orthocresol Novolac Epoxy Resin
Yaku Co., Ltd .: EOCN-1020, softening point 80 ° C., d
Poxy equivalent 220) 13 parts by weight, 3-thiocyanatopro
Pyrmethyldimethoxysilane {NCS (CH₂ )₃Si
CH₃(OCH₃)₂} 2 parts by weight, fused silica powder 74 parts by weight
Parts, 0.90 parts by weight of aluminum acetylacetonate
And 1 part by weight of carnauba wax at 90 ° C
The mixture was kneaded with a resin to produce a thermosetting epoxy resin composition.
The spiral flow of this thermosetting epoxy resin composition
It was measured. Then, apply this thermosetting resin composition to two sheets of
Of a shell plate (length 5 cm, width 1 cm, thickness 0.5 mm)
Sandwiched between them, temperature 175 ° C, pressure 70 kg / cm²,heating
It was compression molded under the condition of time of 2 minutes. Then 180 ° C
After heating for 12 hours to complete the curing,
Adhesion test body in which a cured product of a volatile organic resin composition is integrated
Created. About this test piece, the curable resin composition
Adhesion to a deckle plate as described in the adhesion test (A) above
The results are shown in Table 2.

[0022]

Example 3 In Example 2, 3-isothiocyanatopropyltrimethoxysilane {SCN (CH ₂ ) ₃ Si was used instead of 3-thiocyanatopropylmethyldimethoxysilane.
A thermosetting epoxy resin composition was produced in the same manner as in Example 2 except that (OCH ₃ ) ₃ } was added. The spiral flow and the adhesion to a nickel plate of this composition were measured in the same manner as in Example 2, and the results are shown in Table 2.

[0023]

Comparative Example 3 In Example 2, 3-mercaptopropyltrimethoxysilane {HS (CH ₂ ) ₃ Si was used instead of 3-thiocyanatopropylmethyldimethoxysilane.
A thermosetting epoxy resin composition was produced in the same manner as in Example 2 except that (OCH ₃ ) ₃ } was added. The spiral flow of this composition and the adhesion to a nickel plate were measured by the method described in the above adhesion test (A), and the results are also shown in Table 2.

[0024]

Comparative Example 4 A thermosetting epoxy resin composition was produced in the same manner as in Example 2 except that 3-thiocyanatopropylmethyldimethoxysilane was not added. The moldability (spiral flow) and the adhesion to a nickel plate of this composition were measured in the same manner as in Example 2, and the results are also shown in Table 2.

[0025]

[Table 2]

[0026]

Example 4 35 parts by weight of a bismaleimide-triazine type thermosetting polyimide resin (manufactured by Mitsubishi Gas Chemical Co., Inc.), 3-thiocyanatopropyltrimethoxysilane {N
4 parts by weight of CS (CH ₂ ) ₃ Si (OCH ₃ ) ₃ }, 65 parts by weight of fused silica powder, 1 part by weight of carnauba wax, and 0.32 part by weight of aluminum benzoate were kneaded with a heating roll at 90 ° C. A thermosetting imide resin composition was produced.
The spiral flow of this composition was measured. Subsequently, this composition was applied to two nickel plates (length 5 cm, width 1 cm,
It is sandwiched between a thickness of 0.5 mm), temperature 220 ° C, pressure 70
It was compression molded under the conditions of kg / cm ² and heating time of 4 minutes. Then, it was heated at 230 ° C. for 3 hours to complete the curing, and an adhesion test body in which a nickel plate and a cured product of the thermosetting imide resin composition were integrated was prepared. With respect to this test body, the adhesiveness of the thermosetting imide resin composition to the nickel plate was measured by the method described in the adhesiveness test (A), and the results are shown in Table 3.

[0027]

Comparative Example 5 A thermosetting imide resin composition was produced in the same manner as in Example 4, except that 3-thiocyanatopropyltrimethoxysilane was not added. The spiral flow of this composition and the adhesion to a nickel plate were measured in the same manner as in Example 4, and the results are also shown in Table 3.

[0028]

[Table 3]

[0029]

Example 5 Orthocresol novolac epoxy resin (manufactured by Nippon Kayaku Co., Ltd .: EOCN-1020, softening point 8)
0 ° C, epoxy equivalent 220) 75 parts by weight, fused silica 2
60 parts by weight, Carnauba wax 1 part by weight, phenol novolac resin (Mitsui Chemicals, Inc .: Milex XL
C-3L, softening point 70 ° C., hydroxyl group equivalent 170) 35 parts by weight, triphenylphosphine 0.6 parts by weight, 3-thiocyanatopropyltrimethoxysilane {NCS (C
5 parts by weight of H ₂ ) ₃ Si (OCH ₃ ) ₃ } was kneaded on a heating roll at 90 ° C. to produce a thermosetting epoxy resin composition. The spiral flow of this composition was measured. Subsequently, this composition was applied to two nickel plates (length 5 cm, width 1
cm, thickness 0.5 mm), and compression molded under the conditions of a temperature of 150 ° C., a pressure of 70 kg / cm ² , and a heating time of 3 minutes. Then, it was heated at 180 ° C. for 4 hours to complete the curing, and an adhesion test piece in which the nickel plate and the cured product of the thermosetting epoxy resin composition were integrated was prepared. With respect to this test body, the adhesiveness of the thermosetting epoxy resin composition to the nickel plate was measured by the method described in the adhesiveness test (A), and the results are shown in Table 4.

[0030]

Comparative Example 6 A thermosetting epoxy resin composition was prepared in the same manner as in Example 5 except that 3-glycidoxypropyltrimethoxysilane was used instead of 3-thiocyanatopropyltrimethoxysilane. Was manufactured. The spiral flow of this composition and the adhesiveness to a nickel plate were measured by the method described in the above adhesiveness test (A), and the results are also shown in Table 4.

[0031]

Comparative Example 7 In Example 5, 3-thiocyanatopropyltrimethoxysilane {NCS (CH ₂ ) ₃ Si (OC)
H _{3) 3}} except for not blending was prepared to to thermosetting epoxy resin composition as in Example 5. The spiral flow of this composition and the adhesiveness to a nickel plate were measured by the method described in the above adhesiveness test (A), and the results are also shown in Table 4.

[0032]

[Table 4]

[0033]

Example 6 20 parts by weight of a liquid epoxy resin (ERL-4221 manufactured by Union Carbide Co., Ltd.), a liquid acid anhydride (3
And 4-methylhexahydrophthalic anhydride) 22 parts by weight, tin octylate 0.3 parts by weight, 3-thiocyanatopropyltrimethoxysilane {NCS (CH ₂ ) ₃ Si (O
2 parts by weight of CH ₃ ) ₃ } was thoroughly mixed at room temperature and then degassed to produce a thermosetting liquid epoxy resin composition. The viscosity change rate of this composition was measured. Subsequently, this composition was applied to two nickel plates or two copper plates (each having a length of 5c).
m, width 1 cm, thickness 0.5 mm), temperature 12
Compression molding was carried out under conditions of 0 ° C., pressure of 70 kg / cm ² , and heating time of 3 minutes. Then, it was heated at 150 ° C. for 3 hours to complete the curing, and an adhesion test piece in which a cured product of the thermosetting epoxy resin composition was integrated with a nickel plate or a copper plate was prepared. The adhesiveness of these test bodies was measured by the method described in the adhesiveness test (B), and the results are shown in Table 5.

[0034]

[Comparative Example 8] A thermosetting epoxy resin composition was produced in the same manner as in Example 6 except that 3-mercaptopropyltrimethoxysilane was added instead of 3-thiocyanatopropyltrimethoxysilane. did. The viscosity change rate and adhesiveness of this composition were measured by the method described in the above-mentioned adhesiveness test (B), and the results are also shown in Table 5.

[0035]

Comparative Example 9 A thermosetting epoxy resin composition was prepared in the same manner as in Example 6 except that 3-glycidoxypropyltrimethoxysilane was added instead of 3-thiocyanatopropyltrimethoxysilane. Was manufactured. The viscosity change rate and the adhesiveness of this composition were measured by the adhesiveness test (B).
The measurement was carried out by the method described in 1 and the results are also shown in Table 5.

[0036]

Comparative Example 10 A thermosetting epoxy resin composition was produced in the same manner as in Example 6 except that 3-thiocyanatopropyltrimethoxysilane was not added. This was cured in the same manner as in Example 6. The viscosity change rate and adhesiveness of this composition were measured by the method described in the above-mentioned adhesiveness test (B), and the results are also shown in Table 5.

[0037]

[Table 5]

[0038]

The curable organic resin composition of the present invention comprises
It consists of the component (A) and the component (B), and in particular, the general formula of the component (B): X—R ¹ —Si (OR ² ) _n R ³ _3−n (wherein X is
Is NCS- or SCN-, R ¹ is an alkylene group or an alkyleneoxyalkylene group, R ² and R ³ are monovalent hydrocarbon groups, and n is 1, 2 or 3. ) Represents a thiocyanato group-organoalkoxysilane or an isothiocyanato group-containing organoalkoxysilane (0.01 to 100 parts by weight), so that it has excellent moldability and at the time of curing, the thermosetting organic resin itself is cured. It is characterized in that it cures without impairing its properties and has excellent adhesiveness to a base material such as a metal that comes into contact with it during curing.

   ─────────────────────────────────────────────────── ─── Continued front page    (72) Inventor Akihiko Shirahata             2-2 Chikusaigan, Ichihara-shi, Chiba Toray Dow             Corning Silicone Co., Ltd. R & D             In headquarters F-term (reference) 4J002 CC031 CC121 CC151 CC161                       CC181 CD001 CF011 CF211                       CM041 CN051 CP031 EX086                       FD010 FD020 GH00 GJ01                       GQ05

Claims (5)

[Claims] 1. A curable organic resin (A) (100 parts by weight)
And (B) general formula: X-R¹-Si (OR²)_nR³ _3-n(formula
Wherein X is NCS- or SCN-, R¹ Is Archi
Rene group or alkyleneoxyalkylene group, R
²And R³Is a monovalent hydrocarbon group, n is 1, 2 or
It is 3. ) Organoa containing thiocyanato group represented by
Organo containing lucoxysilane or isothiocyanato group
Made from alkoxysilane (0.01-100 parts by weight)
A curable organic resin composition comprising: 2. The curable organic resin composition according to claim 1, wherein the component (A) is a thermosetting organic resin. 3. The curable organic resin composition according to claim 2, wherein the component (A) is a phenol resin, an epoxy resin or an imide resin. 4. A general formula for the component (B): X—R.¹-S
i (OR²)_nR³ _3-n Medium, R¹Is an alkylene group, R²
And R³Is an alkyl group, and n is 2 or 3.
The curable organic resin composition according to claim 1.
object. 5. The curable organic compound according to claim 1, wherein the component (B) is 3-thiocyanatopropyltrimethoxysilane, 3-thiocyanatopropylmethyldimethoxysilane or 3-isothiocyanatopropyltrimethoxysilane. Resin composition.