JPH0977829A - Perhaloolefin copolymer and production of crosslinked molded form made therefrom - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a crosslinked molded form of high mechanical strength by efficiently chemically crosslinking at low cost a perhallolefin copolymer composed of each specific three kinds of monomer unit and excellent in moldability, adhasivilty to different kinds of material, etc. SOLUTION: Frist, the objective perhallolefin copolymer is obtained, which is composed of 10-95mol% of perhaloolefin unit (e.g. tetrafluoroethylene, chlorotrifluoroethylene), 5-60mol% of olefin unit (e.g. vinyl fluoride, ethylene) and 0.5-50mol% of vinyl alkoxysilane unit (e.g. vinyl triethoxysilane), and has a number-average molecular weight of 10,000-1,000,000 or melt viscosity of 10<2> -10<8> poise. And, the other objective crosslinked molded from is obtained by reaction of the above copolymer with moisture in the presence of a silanol condensation catalyst (e.g. dibutyltin dilaurate).

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a multi-component copolymer obtained by copolymerizing a specific perhaloolefin, an olefin and vinylalkoxysilane, and a method for producing a crosslinked molded product comprising the copolymer. This crosslinked molded article is used in various industrial fields such as automobiles, chemicals, electric wires, and semiconductors.

[0002]

2. Description of the Related Art PTFE resin, FEP resin or PCTF
Fluorine resin represented by E resin has various characteristics such as heat resistance, chemical resistance, excellent electrical characteristics, non-adhesion / lubricity and weather resistance based on the stability of C—F bond, and has a wide range. It is used in various industrial fields. Specific applications include molded products such as pipes, valves, joints, and tubes, coating materials for electric wires and optical fibers, and sealing materials such as packing and gaskets. It is also used as a film requiring weather resistance, corrosion resistance, electric insulation, releasability, and the like, an elastomer requiring excellent automobile oil resistance, and the like.

However, when used for the above-mentioned uses, the conventional fluororesins have not always been sufficiently satisfactory in mechanical strength. Further, when it is attempted to form a laminated film by bonding with a lining or a different type of resin, there is a problem that the adhesiveness is insufficient, and the fluororesin surface has to be etched or lined with glass fiber. Furthermore, since fluororesins do not dissolve in organic solvents with the exception of polyvinylidene fluoride and copolymers of vinylidene fluoride, the molding method is limited and only thermoforming methods such as compression molding and extrusion molding can be used. There was also a problem.

Generally, crosslinking is carried out as a method for improving the mechanical strength of the resin, and in the case of fluororesin, polyvinylidene fluoride or a copolymer of vinylidene fluoride and hexafluoropropylene is electron beam crosslinked. The method of doing has been put to practical use. However, since the electron beam irradiation apparatus is very expensive, a method capable of being inexpensively cross-linked has been investigated, and Japanese Patent Publication No. 11575/1991 proposes a method of reacting a silane compound during molding of polyvinylidene fluoride.

Further, a binary copolymer of a perhaloolefin such as tetrafluoroethylene or chlorotrifluoroethylene and a specific vinylalkoxysilane is known, for example, as described in JP-A-2-103563. , Is being investigated as a carrier coating agent for copying machines. However, in the binary copolymer described in the above publication,
Since the mechanical strength was insufficient, there were restrictions on the application.

[0006]

DISCLOSURE OF THE INVENTION The present invention solves the above problems and provides a multi-component copolymer composed of three specific types of monomers, which has many excellent properties peculiar to the above fluororesins. It is an object of the present invention to provide a copolymer that maintains the above properties, is easy to process, has excellent adhesiveness to different materials, and has a high yield. Another object of the method for producing a crosslinked molded article of the present invention is to provide a method for producing a crosslinked molded article having high mechanical strength by efficiently and inexpensively crosslinking the above-mentioned copolymer by chemical crosslinking.

[0007]

The perhaloolefin copolymer of the first invention is composed of the following monomer units (a), (b) and (c), and is polystyrene by gel permeation chromatography. Converted number average molecular weight is 1
1 to 1,000,000, or melt viscosity by a Koka type flow tester (measurement condition: nozzle; diameter 1 mm, length 10
mm, weight: 100 kg / cm ² , temperature: 200-30
0 ° C.) is 10 ² to 10 ⁸ poise. (A) A unit based on a perhaloolefin represented by the following chemical formula: 10 to 95 mol% CF ₂ = CFX (X is Cl, F, a perfluoroalkyl group or a perfluoroalkoxy group) (b) In the following chemical formula Table 5 to 60 mole% CH ₂ = CX ₂ (X is optionally the same or different Cl, F, H, an alkyl group or a fluoroalkyl group) (c) chemical formula: units based on olefin represented units based on a vinyl alkoxysilane; 0.5-50 ^{_{mole% CH 2 = CH (R 1}} ) m Si (R 2) n (oR 3) 3-n (R 1 is an alkylene group or an oxyalkylene radical, R ² is a methyl group or an ethyl group, R ³ is an alkyl group or an alkoxyalkyl group having 1 to ³ carbon atoms, m is an integer of 0 or 1 to 10, and n is an integer of 0 or 1 to 3) (A), (b) and The total amount of c) is 100 mol%.

Examples of the monomer constituting the above-mentioned "monomer unit (a)" include tetrafluoroethylene, chlorotrifluoroethylene, hexafluoropropylene, decafluoropentene, perfluoro (methyl vinyl ether) and perfluoro (propyl). Vinyl ether) and the like. These monomers may be used alone or in combination of two or more. Among these monomers, tetrafluoroethylene and chlorotrifluoroethylene are preferable from the viewpoint of easy polymerization operation.

As the monomer constituting the above-mentioned "monomer unit (b)", vinyl fluoride, vinylidene fluoride,
Examples thereof include chlorofluoroethylene, trifluoropropylene, hexafluoroisobutylene, vinyl chloride, vinylidene chloride, ethylene, propylene and isobutylene. Among these monomers, vinyl fluoride, vinylidene fluoride, ethylene, and propylene are preferable because the chemical resistance and heat resistance of the resulting copolymer are enhanced.

Further, as the monomer constituting the above-mentioned "monomer unit (c)", vinyltrimethoxysilane, vinyltriethoxysilane, vinyltripropoxysilane, vinyltripentoxysilane, vinyltris (β-methoxy). Ethoxy) silane, vinylmethyldimethoxysilane,
Vinylmethyldiethoxysilane, vinylmethyldipropoxysilane, vinyldimethylmonomethoxysilane, vinyldimethylmonoethoxysilane, vinylethylmonomethoxysilane, vinylethylmonoethoxysilane, trimethoxysilylhexene, trimethoxysilylpropyl vinyl ether, trimethoxysilyl Examples thereof include decyl vinyl ester and triethoxysilylpropyl acrylate.

Among the various vinylalkoxysilanes mentioned above, those in which R ³ is an ethyl group or a methoxyethyl group are preferred from the viewpoint of the storage stability of the copolymer and the reactivity at the time of crosslinking, and a particularly preferred monomer The body is vinyltriethoxysilane.

In the perhaloolefin copolymer of the present invention, the amount ratio of each of the above monomer units is preferably (a).
/ (B) / (c) is 20-90 / 10-55 / 0.5-
15 mol%, more preferably 50-85 / 15-
50 / 0.5 to 10 mol% (however, the monomer unit (a),
The total amount of (b) and (c) is 100 mol%. ].

When the content of the monomer unit (a) exceeds 90 mol%, the copolymer has good heat resistance and chemical resistance, but the adhesiveness to different materials tends to be low, and the content is 20 mol%. If it is less than the above range, heat resistance and chemical resistance may decrease. Further, when the monomer unit (b) exceeds 55 mol%, the polymerizability decreases, and when it is less than 10 mol%, the molding temperature of the copolymer cannot be lowered sufficiently and the moldability deteriorates. To do. Further, when the monomer unit (c) exceeds 15 mol%, it is easy to crosslink and the adhesion is improved, but when it is made into a molded product, it tends to be brittle and the chemical resistance tends to decrease. This is 1
If it is less than mol%, the mechanical strength is not sufficiently improved, and the adhesion may be lowered, which is not preferable.

The copolymer of the present invention can be obtained by radical polymerization such as bulk polymerization, solution polymerization, suspension polymerization and emulsion polymerization. Examples of the radical polymerization initiator include organic compounds such as diisopropyl peroxydicarbonate, dinormal propyl peroxydicarbonate, isobutyryl peroxide, perfluorobutyryl peroxide, di (chlorofluoroacyl) peroxide, and di (perfluoroacyl) peroxide. Peroxides, azo compounds such as azobisisobutyronitrile, and inorganic peroxides such as ammonium persulfate and potassium persulfate can be used. It is also possible to add a reducing agent such as Rongalit or sodium sulfite to polymerize as a redox initiator.

The solvent used in the solution polymerization is
Tertiary butanol and fluorine-based solvents are suitable. Examples of the fluorine-based solvent include trichlorotrifluoroethane, CF ₂ ClCF ₂ Cl, CF ₂ ClCF ₂ CHCl
F, CF ₃ CHCl ₂ , octafluorocyclobutane, perfluoro cyclic ether and the like. In suspension polymerization and emulsion polymerization, the solvent is usually water, and if necessary, a fluorinated solvent, a suspension stabilizer, a pH adjuster, an emulsifier and the like can be made to coexist.

Examples of the above-mentioned suspension stabilizer include methyl cellulose, polyvinyl alcohol and the like. As the pH stabilizer, known compounds such as disodium phosphate, sodium hydrogen carbonate, potassium carbonate and sodium borate can be used. it can. Examples of emulsifiers include ammonium perfluorooctanoate and sodium dodecylbenzene sulfonate. Furthermore, in the above-mentioned polymerization system, alcohols, ketones, esters as chain transfer agents,
Ethers and mercaptans may be added.

The polymerization temperature can be selected in the same range as in the ordinary radical polymerization, for example, 0 to 100 ° C., especially 20.
The range of -50 ° C is preferred. Polymerization pressure is 1 to 50 kg /
The range of cm ² · G is preferable. The polymerization time is 3 to
It is preferably 50 hours, particularly 10 to 30 hours. As the polymerization method, a batch method in which all the monomers are charged in advance, or after the polymerization is started by charging a part of the monomers,
A sequential addition method or the like for additionally supplying a required monomer can be adopted.

The molecular weight of the perhaloolefin copolymer of the present invention can be determined by gel permeation chromatography (hereinafter referred to as GPC) if the copolymer is soluble in an organic solvent. The polystyrene-equivalent number average molecular weight by GPC is 10,000 to 1,000,000, and preferably 50,000 to 500,000. If the number average molecular weight is less than 10,000, the mechanical strength of the molded product obtained by molding the copolymer will be poor, and if it exceeds 1 million, the moldability will be poor.

When the copolymer does not dissolve in an organic solvent, a melt flow viscosity measured by a Koka type flow tester under the following conditions can be used as an index of the molecular weight. Has a melt viscosity in the range of 10 ² to 10 ⁸ poise. Melt viscosity measurement conditions: nozzle; diameter 1 mm, length 10 m
m, weight; 100 kg / cm ² , temperature; 200 to 300
° C

The method for producing a crosslinked molded article according to the second aspect of the present invention is the first aspect.
It is characterized in that it comprises a step of reacting the perhaloolefin copolymer of the invention with water in the presence of a silanol condensation catalyst.

As the above-mentioned "silanol condensation catalyst", dibutyltin dilaurate, dioctyltin dilaurate, tin octoate, tin acetate, lead naphthenate, zinc caproate,
Examples thereof include iron 2-ethylhexanoate, cobalt naphthenate, tetranonyl titanate ester, and via (acetylacetonitrile) diisopropyl titanate. Also,
Inorganic acids such as hydrochloric acid, sulfuric acid and phosphoric acid, and organic acids such as paratoluene sulfonic acid and acetic acid can also be used.
The amount of the catalyst used is 0.0001 to 10% by weight, especially 0.01 to 5% by weight, based on 100% by weight of the copolymer.
A range of weight% is preferred.

The above-mentioned "moisture" is an ordinary aqueous medium such as water, steam, warm water, a mixture of water and an organic solvent. The copolymer and the water, after molding the copolymer into a desired shape,
It is possible to "react" by immersing in warm water containing a silanol condensation catalyst, or by passing a molded article molded from a copolymer containing a silanol condensation catalyst into a steam atmosphere, whereby the copolymerization The united body is crosslinked to produce a "crosslinked molded body". It is also possible to add a small amount of water in advance before molding the copolymer into a desired shape and crosslink it during molding or during and after molding.
As the method for molding the copolymer of the present invention, compression molding, injection molding, melt molding, extrusion molding and the like can be adopted, and generally used conditions can be applied as molding conditions. In addition, when the copolymer is soluble in an organic solvent, it is also possible to adopt a method in which the solution is poured onto the surface of another article.

Further, during the above-mentioned crosslinking operation, various materials such as aramid fiber, carbon fiber, graphite and bronze can be added and blended to improve the strength of the crosslinked molded article. Furthermore, when a multilayer film is formed by using the copolymer of the first invention, the silanol condensation catalyst contributes to the adhesion to different films if the cross-linking is performed after forming the multilayer, and the adhesive force between the two films is increased. It can also be strengthened.

[0024]

BEST MODE FOR CARRYING OUT THE INVENTION The present invention will be described below based on Examples and Comparative Examples. Example 1 (1) Production of Perhalo-Olefin Copolymer In an autoclave with a volume of 1 liter equipped with a stirrer,
360 g of 1,1,2-trifluoro-1,2,2-trichloroethane (hereinafter referred to as F113) and vinyltriethoxysilane (hereinafter referred to as VTRIES) 4.5.
After deaeration and nitrogen substitution were repeated 3 times, the mixture was deaerated again and chlorotrifluoroethylene (hereinafter referred to as CTFE).
Say. ) 250 g and vinylidene fluoride (hereinafter VdF
Say. ) 82 g was charged.

Thereafter, the mixture was heated to 40 ° C., 2.5 g of a 50 wt% methanol solution of dinormal propyl peroxydicarbonate was press-fitted, and polymerization was initiated.
After polymerizing for 22 hours, unreacted CTFE and VdF were purged and the autoclave was opened. After recovering F113 from the obtained polymerization solution, ethanol was added to wash the copolymer, and the copolymer was dried. Thus, 322 g (yield: 96% by weight) of a white soft copolymer was obtained.

The above copolymer is soluble in acetone and tetrahydrofuran (hereinafter referred to as "THF"), and DSC
Glass transition temperature of copolymer (hereinafter, T
It is called g. ) Was 11 ° C., and the polystyrene reduced number average molecular weight measured by GPC was 120,000.

When the infrared absorption spectrum was measured, a peak attributable to the Si--O bond was observed near 1050 cm ^-1 . In addition, the peak due to CH ₂ is 30
A peak due to CF ₂ is 1100 near 00 cm ^−1.
It was observed in the vicinity of 1280 cm ^-1 . According to elemental analysis of the copolymer, F = 50.8% by weight, Cl = 22.
6% by weight, C = 25.1% by weight, Si = 0.20% by weight
The composition of the copolymer based on these analysis results is
CTFE / VdF / VTRIES = 62/37/1 (mol%).

(2) Production of crosslinked molded product The above copolymer was dissolved in acetone to prepare a 30% by weight solution, and this solution was applied to the surface of a hard vinyl chloride molded plate (manufactured by Nippon Test Panel Co., Ltd.). Polymer film thickness is 30
It was adjusted with an applicator so as to have a thickness of μm and then painted. Then, it was dried to remove acetone and a copolymer film was formed on the molded plate. Then, the molded plate on which this film is formed is dipped in an aqueous suspension containing 5% by weight of dibutyltin dilaurate, and allowed to stand at room temperature for 24 hours to crosslink, thereby forming a crosslinked molded film on the surface of the hard vinyl chloride molded plate. A composite plate in which was formed was obtained.

An attempt was made to extract the crosslinked molded body by immersing the above composite plate in acetone, but the crosslinked molded body was hardly dissolved in acetone, and the crosslinking rate (weight ratio of acetone insoluble matter) was 82.
%Met. In addition, the result of the base sheet cellophane tape peeling test according to JIS K5400 was 100/100, and there was no peeling at all, and the crosslinked molded body film was firmly adhered to the molded plate. Furthermore, when the film was heated in a dryer set at 60 ° C. for 30 minutes, no deformation or shrinkage of the film was observed.

Example 2 (1) Production of Copolymer In an autoclave with a capacity of 1 liter equipped with a stirrer, 400 g of water and 10 g of ammonium perfluorooctanoate were added.
And 12 g of sodium hydrogencarbonate are added, and VTRI is further added.
After charging 2.5 g of ES, repeating deaeration and nitrogen substitution three times, and then deaeration again, tetrafluoroethylene (hereinafter, T
It is called FE. ) 24 g and 0.4 g of ethylene were charged.

Thereafter, the mixture is heated to 35 ° C., 1 g of ammonium persulfate and 0.5 g of sodium sulfite.
An aqueous solution prepared by dissolving each of these in 10 cc of water was injected under pressure to initiate polymerization. After initiation of the polymerization, 100 g of a monomer mixture consisting of 84 to 16 weight ratio of TFE and ethylene was post-added in several times, and VTRIES was added at the 3rd, 7th and 10th hours after the initiation of the polymerization. 1.0 g of each was added and the polymerization was continued for a total of 19 hours. Then, after unreacted TFE and ethylene were purged and the autoclave was opened, the copolymer was separated from the obtained milky white emulsion by freeze coagulation, washed with water and dried to give 98 g (yield; 75% by weight).
A copolymer of

The above copolymer was insoluble in acetone, toluene and hexane and had a melting point (hereinafter referred to as Tm) of 240 ° C. measured by DSC. In addition, when a flow test was performed using a Koka type flow tester (manufactured by Shimadzu Corporation), the melt viscosity at 290 ° C. was 8 × 10.
It was ³ poise.

Further, when the infrared absorption spectrum was measured, a peak attributable to the Si--O bond was observed near 1050 cm ^-1 . In addition, the peak due to CH ₂ is 30
A peak due to CF ₂ is 1100 near 00 cm ^−1.
It was observed in the vicinity of 1280 cm ^-1 . Further, according to the elemental analysis of the copolymer, F = 60.5% by weight, Si = 0.8
% By weight, C = 34.7% by weight, and the composition of the copolymer based on these analysis results was TFE / ethylene / VTR.
IES = 58/40/2 (mol%).

(2) Production of Crosslinked Molded Body 10 g of the above copolymer was placed in a metal mold having an inner surface plated with chrome, and mounted on a press machine. Then, at 300 ° C
After dewatering for 30 minutes by holding at 50kg / cm
A pressure of ² was applied for compression molding. Immediately after molding, it was cooled to obtain a molded product having a thickness of 1 mm. Next, the molded body is immersed in a suspension water containing 5% by weight of dibutyltin dilaurate,
The temperature was raised to 0 ° C. and crosslinking was performed for 24 hours. ASTM D638
When a tensile test of this crosslinked molded article was conducted in accordance with
The strength was 450 kg / cm ² , and the elongation was 500%.

Example 3 (1) Production of Copolymer The polymerization solvent was changed to 180 g of perfluoro cyclic ether (manufactured by 3M, trade name "Florinato FC72") and 180 g of water, and the monomer was changed to 350 g of CTFE.
68 g of propylene and 20 g of vinyltris (β-methoxyethoxy) silane (hereinafter referred to as VTRIMES)
Polymerization was performed in the same manner as in Example 1 except that the above was changed to. After completion of the polymerization, water was separated, poured into ethanol, washed and dried to obtain 200 g (yield: 46% by weight) of a copolymer.

The above copolymers are acetone, toluene, T
It is soluble in HF and has a Tg of 41 ° C and a number average molecular weight of 50.
It was 000. According to elemental analysis of this copolymer, F = 33.3% by weight, Cl = 20.7% by weight, C =
37.8% by weight and Si = 0.9% by weight, and the composition of the copolymer based on these analysis results was CTFE / propylene / VTRIMES = 50/47/3 (mol%).

(2) Production of cross-linked molded product The above copolymer was dissolved in toluene to prepare a 50 wt% solution. Then, to this solution, 0.5% by weight of dibutyltin dilaurate and 3% by weight of water were added to 100% by weight of the copolymer, and the film thickness of the copolymer film was 30 μm on the surface of the hard vinyl chloride molded plate. It was adjusted with an applicator and painted. Crosslinking was carried out as it was at room temperature for 1 week to obtain a composite plate having a crosslinked molded body film formed on the molded plate.

An attempt was made to extract the crosslinked molded product by immersing the above composite plate in acetone, but the crosslinked molded product was hardly dissolved in acetone and the crosslinking rate was calculated to be 88%.
In addition, the result of the base cellophane tape peeling test is 100/10.
It was 0, and the film was firmly adhered to the molded plate. In addition, the film was heated for 30 minutes in a dryer set at 80 ° C., but no deformation or shrinkage of the film was observed.

Example 4 The polymerization solvent was F113 and water (200 g each), and the monomer was VdF7.
Polymerization was performed in the same manner as in Example 1 except that 1 g, TFE 63 g, and VTRIES 7.1 g were used. Immediately after completion of the polymerization, F113 was recovered, and then the copolymer was separated with a 200-mesh filter cloth. Yield 71 after washing and drying
It was g (yield; 50% by weight).

The above copolymer was insoluble in acetone, toluene and hexane, and had a Tm of 185 ° C. and a melt viscosity at 40 ° C. of 10 ³ poise. According to the elemental analysis of the copolymer, F = 64.7% by weight, C = 31.1% by weight,
Si = 1.1% by weight, H = 2.1% by weight, and the composition of the copolymer based on these analysis results was TFE / VdF /
VTRIES = 44/5/3/3 (mol%). Further, when heat molding and crosslinking were carried out in the same manner as in Example 2 and a tensile test was performed on the obtained crosslinked molded article, a strength of 30 was obtained.
It was 0 Kg / cm ² and the elongation was 600%.

Comparative Example 1 A copolymer was obtained in the same manner as in Example 1 except that VTRIES was not used. The Tg of this copolymer was 6 ° C., and the composition of the copolymer was CTFE / VdF = 65/35.
(Mol%). Then, in the same manner as in Example 1, a film having a thickness of 30 μm was formed on the surface of the hard vinyl chloride molded plate. When it was dried at room temperature and subjected to an acetone extraction test, the entire film was dissolved. In addition, the result of the base cellophane tape peeling test was 0/100, and the above film was completely peeled from the molded plate. Furthermore, when heated for 30 minutes in a dryer set at 60 ° C., shrinkage of the film was observed.

Comparative Example 2 A copolymer was obtained in the same manner as in Example 2 except that VTRIES was not used. The Tm of this copolymer was 280 ° C., and the composition of the copolymer was TFE / ethylene = 51/49.
(Mol%). Then, after heat-molding in the same manner as in Example 2 (however, since the Tm was high, the molding temperature was also increased to 330 ° C.), a tensile test was conducted, and a strength of 41 was obtained.
The results were 0 kg / cm ² and an elongation of 300%, which were inferior to those of Example 2.

[0043]

EFFECT OF THE INVENTION The perhaloolefin copolymer of the first invention has a high yield, maintains many of the excellent properties peculiar to fluororesins, is easy to process, and has excellent adhesiveness to different materials. . Further, the method for producing a crosslinked molded article according to the second aspect of the invention is chemical crosslinking, is inexpensive, and can be efficiently crosslinked, and a crosslinked molded article having high mechanical strength can be obtained.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Internal reference number FI Technical display location C08L 5/00 CEW C08L 5/00 CEW // C08L 27:12 (72) Inventor Akito Iida Aichi 1 Touna Gosei Co., Ltd., Nagoya Research Institute, 1 Funami-cho, Minato-ku, Nagoya, Japan

Claims (2)

[Claims] 1. A number average molecular weight in terms of polystyrene by gel permeation chromatography, which is composed of the following monomer units (a), (b) and (c), is 10,000 to 1,000,000, or Melt viscosity by Koka type flow tester (measurement condition: nozzle; diameter 1 mm, length 10 m
m, weight; 100 kg / cm ² , temperature; 200 to 300
Perhaloolefin copolymer having a temperature of 10 ² to 10 ⁸ poise. (A) A unit based on a perhaloolefin represented by the following chemical formula: 10 to 95 mol% CF ₂ = CFX (X is Cl, F, a perfluoroalkyl group or a perfluoroalkoxy group) (b) In the following chemical formula Table 5 to 60 mole% CH ₂ = CX ₂ (X is optionally the same or different Cl, F, H, an alkyl group or a fluoroalkyl group) (c) chemical formula: units based on olefin represented units based on a vinyl alkoxysilane; 0.5-50 ^{_{mole% CH 2 = CH (R 1}} ) m Si (R 2) n (oR 3) 3-n (R 1 is an alkylene group or an oxyalkylene radical, R ² is a methyl group or an ethyl group, R ³ is an alkyl group or an alkoxyalkyl group having 1 to ³ carbon atoms, m is an integer of 0 or 1 to 10, and n is an integer of 0 or 1 to 3) (A), (b) and The total amount of c) is 100 mol%. 2. A method for producing a crosslinked molded article comprising a perhaloolefin copolymer, which comprises a step of reacting the copolymer according to claim 1 with water in the presence of a silanol condensation catalyst.