JP3445866B2 - Method for producing functional group-containing polymer - Google Patents

Description

Detailed Description of the Invention

[0001]

The present invention relates to an isobutylene polymer having at least one alkenyl group at the end of one molecule and having an average molecular weight of 1,000 to 200,000 in the presence of a platinum catalyst. The present invention relates to a method for producing a functional group-containing polymer, in which the oxygen concentration in the gas phase of the reactor is adjusted during hydrosilylation reaction.

[0002]

2. Description of the Related Art Polymers containing an unsaturated group in a molecule are used in adhesives, pressure-sensitive adhesives, paints, coatings by allowing the unsaturated group to participate in crosslinking in various ways. It is useful as a raw material for materials, sealing materials, and sealants for electrical and electronic equipment.

In particular, an unsaturated group-containing polymer has a composition of 51
In the case of an isobutylene-based polymer containing mol% or more of isobutylene units (hereinafter referred to as an isobutylene-based polymer), it is expected to have a wide range of applications by taking advantage of isobutylene's rubber elasticity, electric insulation and low water vapor permeability.

Although isobutylene-based polymers are generally produced by cationic polymerization at low temperatures, the high molecular weight isobutylene-based polymers commonly referred to as butyl rubber do not exhibit the required fluidity at room temperature and are more solvent resistant. It has poor solubility and poor moldability and workability.

The number average molecular weight of the isobutylene-based polymer is 1,000 or more 20 so as not to hinder molding or processing.
A technique of controlling the amount to less than 10,000 and obtaining a cured product by causing an unsaturated group in the molecule to participate in crosslinking by various methods is important as a technique for compensating for the drawbacks of butyl rubber while utilizing the characteristics of isobutylene. Number average molecular weight 1,000 or more 200,
As a method for producing an isobutylene-based polymer of less than 000, 1,4-bis (α-chloroisopropyl) benzene (p-
DCC) or 1,3,5-tris (α-chloroisopropyl) benzene (TCC) is used as a polymerization initiator and chain transfer agent, and cationic polymerization is performed using boron trichloride as a catalyst, and a chlorine atom bonded to a tertiary carbon atom at the end. The Inifer method of Mr. Kennedy et al. (U.S. Pat. No. 4,276,394).

Further, as a method for introducing a vinyl group into an isobutylene polymer obtained by the inifer method, a method using allyltrimethylsilane (JP-A-63-105005) and a method using non-conjugated dienes (special (Kaihei 4-288309) is publicly known.

A functional group-containing polymer obtained by introducing a hydrosilyl group-containing compound into an unsaturated group by utilizing a hydrosilylation reaction with respect to an unsaturated group-containing polymer thus synthesized is It is particularly effective as a raw material for adhesives, adhesives, and sealing materials (Japanese Patent Laid-Open No. Sho 61-96).
63-006041, JP-A-1-038407, JP-A-1-198673
JP-A 1-170681, JP-A 1-165648, JP-A 4-159371, etc.).

Conventionally, when the above isobutylene polymer and the hydrosilyl group-containing compound are reacted, when the isobutylene polymer is a liquid having a low molecular weight and a low viscosity at room temperature, it is heated without solvent under heating. , A hydrosilyl group-containing compound and a platinum catalyst are mixed. Alternatively, when the isobutylene-based polymer has a high molecular weight and is solid at room temperature due to high viscosity or crystallinity, a non-reactive good solvent is used to dissolve the isobutylene-based polymer in a good solvent to give a low viscosity, After being liquefied or after being mixed with a plasticizer to reduce the viscosity, it is carried out by heating and mixing the hydrosilyl group-containing compound and the platinum catalyst. After each reaction, the solvent and unreacted components are distilled off. It is common to obtain the desired product. Particularly in the operation on an industrial scale, in order to ensure safety, it is general to carry out the gas phase part of the reactor in the presence of an inert gas such as nitrogen or helium.

However, when a hydrosilylation reaction of an isobutylene polymer having at least one alkenyl group at the end of one molecule, which is the object of the present invention, is carried out in the presence of a platinum catalyst, the gas phase portion of the reactor is When carried out in the presence of an inert gas such as nitrogen or helium, the catalytic activity in the reaction is extremely low and the rate of the hydrosilylation reaction is extremely reduced, or the reaction takes several hours, resulting in extremely high productivity. There is a cause of a problem in product quality, such as a decrease in the content of functional groups and a reduction in the desired physical properties.

On the other hand, Onopchenko, A. a.
nd Sabourin, E .: J. Org. Chem., 52, 4118 (1987)) or Lewis's paper (Lewis, LN: J. Am. Chem. Soc., 112, 5998, (1)
990)) and JP-A-5-213972, when a platinum catalyst is used, 1-octene and 1-alkene such as triethylsilane, methyldioctylsilane, trioctylsilane and dioctylsilane are used. With alkyl-, dialkyl- or trialkylsilanes, with triethylsilane and vinyltrimethylsilane or vinyltrichlorosilane, or with cyclohexene and methyldichlorosilane, 1-hexene or cyclohexene and methyldisilane. Reaction with chlorosilane, reaction with 1-hexene and dimethoxymethylsilane, 1,1,1,2,3,3,3-
Reaction of heptamethyltrisiloxane with 1-hexene or trans-2-hexene, triethylsilane with trans-
It has been reported that dissolved oxygen in the reaction system affects the reaction in the reaction with 2-hexene, the reaction between trichlorosilane and 1,5-hexadiene, and the like.

Even when the hydrosilylation reaction of an isobutylene polymer having at least one alkenyl group at the end of one molecule which is the object of the present invention is carried out in the presence of a platinum catalyst, the presence of oxygen in the reaction system Although there is a possibility that the hydrosilylation reaction can proceed stably, the reaction procedure for stabilizing the hydrosilylation reaction activity and proceeding the reaction can be carried out while avoiding the risk of explosion of the hydrosilyl group-containing compound. No methodologies have been proposed, and it is important to ensure safety, especially in operation, on an industrial scale, but it is required to propose a reaction operation method that overcomes this point.

[0012]

The present invention has been achieved after the inventors of the present invention have made extensive studies in order to solve the above-mentioned problems. That is, the present invention relates to hydrosilylation reaction of an isobutylene polymer having at least one alkenyl group at the end of one molecule and having an average molecular weight of 1,000 to 200,000 in the presence of a platinum catalyst. , At least 0.1% oxygen concentration in the gas phase of the reactor
And a method for producing a functional group-containing polymer characterized by carrying out the reaction under conditions of less than the explosion limit oxygen concentration of the compound containing a hydrosilyl group, it is possible to solve the above problems I found it.

By adjusting the oxygen concentration in the gas phase of the reactor according to the method of the present invention, the oxygen concentration in the reaction solution can be efficiently adjusted, and the hydrosilylation reaction activity of the platinum catalyst can be stably continued to obtain an adhesive agent. A functional group-containing polymer useful as a raw material for adhesives or sealing agents can be produced.

The isobutylene polymer used in the present invention has at least one alkenyl group at the end of one molecule and has an average molecular weight of 1,000 to 200,000.
As long as it is a polymer of 0 and contains an alkenyl group having a hydrosilylation reaction activity, there is no particular limitation on the production method, and all known production methods can be effectively used. Considering the industrial utility value of the functional group-containing polymer after the reaction with, the repeating unit constituting the polymer main chain is preferably saturated hydrocarbon in terms of heat resistance and weather resistance, among them, It is particularly preferable to use polyisobutylene as the main chain component.

In particular, the field of application of the functional group polymer is one in which the characteristics as a cross-linked polymer are utilized, adhesives,
When used for applications such as weather resistance, heat resistance, and permeation resistance of adhesives, paints, sealing materials, waterproof materials, etc., the main chain component of the polymer is a copolymer whose main component is isobutylene unit. More preferably, That is, the composition is 51 mol%
Or more, preferably 80 mol% or more, more preferably 90 mol% or more.
It is desired to contain more than mol% isobutylene units.
The remaining components can be arbitrarily selected from cationically polymerizable monomers that can be copolymerized with isobutylene. For example, olefins having 5 to 12 carbon atoms, conjugated dienes, non-conjugated dienes, vinyl ethers , Aromatic vinyl compounds, norbornenes, cyclopentadiene,
Examples thereof include dicyclopentadiene and vinylsilanes. These components may be copolymerized alone with isobutylene, or may be copolymerized with two or more components used in combination.

Specific examples of the hydrosilyl group-containing compound used in the present invention include, for example, trichlorosilane,
Halogenated silanes such as methyldichlorosilane, dimethylchlorosilane, trimethylsiloxydichlorosilane,
Alkoxysilanes such as trimethoxysilane, triethoxysilane, methyldimethoxysilane, dimethylmethoxysilane, phenyldimethoxysilane, 1,3,3,5,5,7,7-heptamethyl-1,1-dimethoxytetrasiloxane, methyl Acyloxysilanes such as diacetoxysilane and trimethylsiloxymethylacetoxysilane, ketoxymate silanes such as bis (diethylketoximate) trimethylsiloxysilane, dimethylsilane, trimethylsiloxymethylsilane, 1,1,3,3- Tetramethyldisiloxane,
S in the molecule of 1,3,5-trimethylcyclotrisiloxane
Examples thereof include hydrosilanes having two or more iH bonds and alkenyloxysilanes such as methyldi (isopropenyloxy) silane, but are not limited thereto.

Among these compounds, chlorosilanes such as trichlorosilane and methyldichlorosilane, which have high activity in the hydrosilylation reaction, are preferable, and the obtained functional group-containing polymer has mild hydrolyzability. , And alkoxysilanes such as trimethoxysilane and methyldimethoxysilane are preferable.

When a hydrosilane having two or more SiH bonds in the molecule is used, the molecular weight of the isobutylene polymer can be controlled to double or triple the molecular weight depending on the amount used. There is a side that becomes,
It has the advantage that the range in terms of molecular weight control can be expanded.

The amount of the hydrosilyl group-containing compound used is not particularly limited, but is preferably 0.2 to 20 moles per 1 mole of the alkenyl group in the isobutylene polymer component, but it is economical in industrial operation. In consideration of the characteristics, 0.5 to 10 mol is preferable, and a more preferable operating range is 0.8 to 3 mol.

As the platinum catalyst for hydrosilylation used in the present invention, platinum metal, platinum compound and platinum complex on a carrier can be preferably used. Specifically, for example, platinum metal, alumina, silica, platinum metal on a carrier in which solid platinum is supported on a carrier such as carbon black, chloroplatinic acid, a complex of chloroplatinic acid with alcohol, aldehyde, ketone, etc. Platinum compound such as platinum-olefin complex (for example, Pt
_{(CH 2 = CH 2) 2} (PPh 3) 2 Pt (CH 2 = CH
₂ ) ₂ Cl ₂ ), platinum-vinyl siloxane complex (for example, Pt _n (ViMe ₂ SiOSiMe ₂ Vi) _m , P
t [(MeViSiO) ₄ ] _m ), platinum-phosphine complex (for example, Pt (PPh ₃ ) ₄ and Pt (PBu ₃ ).
₄ ), platinum-phosphite complex (for example, Pt [P (O
Ph) ₃ ] ₄ ), [wherein Me represents a methyl group, Bu represents a butyl group, Vi represents a vinyl group, Ph represents a phenyl group, m,
n represents an integer] and the like.

Dicarbonyldichloroplatinum and Ashby US Pat. Nos. 3,159,601 and 3,159,6.
Also included are the platinum-hydrocarbon complexes described in 62, as well as the platinum alcoholate catalysts described in Lamoreaux, US Pat. No. 3,220,972. Further, the platinum chloride-olefin composites described in Modic US Pat. No. 3,516,946 are also useful in the present invention.

These catalysts may be used alone or 2
From the viewpoint of catalytic activity, chloroplatinic acid, a platinum-olefin complex, a platinum-acetylacetonate complex, and a platinum-vinylsiloxane complex are preferable, although they can be used in combination.

The amount of the catalyst used is not particularly limited, but Pt is 10 ^-1 to 10 ^-8 mol, preferably 10 ^-3 to 1 mol of the alkenyl group in the isobutylene polymer.
It is preferable to use it in the range of 10 ^-6 mol. When it is less than 10 ^-8 mol, hydrosilylation may not proceed sufficiently. Further, it is preferable not to use more than 10 ^-1 mol from the viewpoint of economical efficiency, corrosiveness and generation of by-products.

The catalyst may be diluted with an inert solvent for easy handling and stabilization. As the solvent therefor, hydrocarbon solvents such as benzene, toluene and xylene, and polar solvents such as alcohols, various glycols and esters are preferable.

A solvent can be used in the reaction of the present invention. This solvent has a boiling point higher than the reaction temperature used, can dissolve the isobutylene polymer and the compound containing a hydrosilyl group, and is not particularly limited as long as it does not inhibit the reaction. For example, when the polymer main chain constituting the isobutylene-based polymer is polyisobutylene, hexane, heptane, octane, aliphatic hydrocarbons such as decane, benzene, aromatic hydrocarbons such as toluene, methylene chloride. , Halogenated hydrocarbons such as ethane dichloride, ethers such as ethylene diglycol,
Alternatively, a mixed solvent of two or more of these may be mentioned.

The method of the present invention can also be carried out in the presence of a plasticizer. The plasticizer used in the present invention is not particularly limited as long as it has good compatibility with the isobutylene polymer, has a relatively high boiling point, and does not inhibit the reaction. For example, when the main chain skeleton of the isobutylene polymer is a saturated hydrocarbon such as polyisobutylene, polybutene, hydrogenated polybutene, α-methylstyrene oligomer,
Hydrocarbon compounds such as biphenyl, triphenyl, triaryldimethane, alkylenetriphenyl, liquid polybutadiene, hydrogenated liquid polybutadiene and alkyldiphenyl, BAA-15 (Dahachi Chemical Industry Co., Ltd.), P-103, W32
0 (Dainippon Ink), PN-150 (Adeka Argus)
Adipate compounds such as TOTM, TITM
(Nippon Rika), W-700 (Dainippon Ink) and other trimellitic acid ester compounds, NS-100, NM-2
6, NP-24, PS-32 (Idemitsu Kosan) and other petroleum-based process oils, Alken-68 (Nippon Petroleum Detergent), BF
-1000 (Adeka Argus), KE-828 (Arakawa Kagaku), DOTP (New Japan Rika), etc. are preferable, and Alken-68, PS-32, DOT in that the weight loss upon heating is particularly small.
P, NS-100, TOTM and the like are particularly preferable, but not limited thereto.

The amount of these plasticizers to be used may be appropriately determined depending on the effect of lowering the viscosity of the functional group-containing polymer and the total amount of the plasticizer used in the intended use of the polymer. Specifically, for example, about 10 to 100 parts by weight based on the isobutylene polymer is preferable.

The reaction temperature of the present invention can be varied over a wide range, and in particular, the optimum temperature of the reaction depends on the concentration of the catalyst and the nature of the reactants, but can be carried out in the range of 30 to 200 ° C. It can be carried out preferably in the range of 50 to 120 ° C.

The reaction time to complete the reaction depends on the operating temperature,
Depending on the reaction conditions, depending on the pressure, amount of catalyst, and mass of the reactive group, the completion of the reaction is determined by gas chromatography, I
It can be known by using analytical instruments such as R and NMR.

The selection of the reactor is not particularly limited, and the batch type, the semi-batch type and the continuous type basically have a gas-liquid interface and an oxygen atmosphere regardless of the difference in structure. The reaction can be carried out as long as the reaction can be performed.

Here, the determination of the explosion limit oxygen concentration in the reactor, the method of introducing oxygen, etc. are the most important features of the present invention, and are as follows. The method of supplying oxygen to the reactor is not particularly limited, but it is preferable to adjust a mixed gas in which the amount of oxygen present in the inert gas is regulated in advance with a cylinder or a diluter (regulator). Injecting into the reactor, adjusting the flow rate of inert gas and air or oxygen into the reactor, adjusting oxygen by the ratio of the flow rate of air or oxygen to the flow rate of inert gas, etc. Can be adopted. Further, the oxygen concentration in the reactor is adjusted by introducing an inert gas and air or oxygen into the reactor gas phase portion by valve operation while detecting the oxygen concentration in the gas phase portion or the liquid phase portion with a sensor or the like. can do.

Regarding the amount of oxygen used in the reaction, the upper limit of the oxygen concentration in the gas phase of the reactor can be determined by measuring the explosion limit oxygen concentration of the hydrosilyl group-containing compound used in the hydrosilylation reaction. Here, the explosion limit oxygen concentration is generally determined from an experimental result of whether or not an explosion occurs when the composition of oxygen / inert gas / hydrosilyl group-containing compound is changed. The term "below the explosion limit oxygen concentration" refers to the range of oxygen concentration below point A shown in FIG. 1, and indicates the range below the explosion limit oxygen concentration as the shaded area. Here, as an example of the hydrosilyl group-containing compound, the results obtained by carrying out the explosion experiment are shown for dimethoxymethylsilane for which data on the explosion limit oxygen concentration is not presented. In this figure, ○ indicates the result of explosion when an ignition source was applied when nitrogen and dimethoxymethylsilane with different oxygen concentrations were changed to the desired mixing ratio, and × indicates no explosion. The result is shown. Therefore, in the case of dimethoxymethylsilane, it can be seen from FIG. 1 that the explosion limit oxygen concentration is 9.5% of point A, and the oxygen concentration range that can be adopted as the reaction condition in the present invention is 9.5.
That is less than%. By obtaining the experimental data on the oxygen concentration at the explosion limit, the upper limit of the oxygen concentration in the gas phase of the reactor can be determined even when any compound containing a hydrosilyl group is used. However, if the hydrosilylation reaction is carried out under oxygen concentration conditions higher than this range, a serious accident may occur if any ignition source is present, and it will be used as an operating condition on an industrial scale. Doing so is not preferable.

On the other hand, the lower limit of the oxygen concentration in the gas phase of the reactor is
Although not particularly limited, when the oxygen concentration is extremely low, the reaction rate decreases, so that the reaction time increases, which leads to a decrease in productivity and an increase in equipment. It is required to be 1% or more, more preferably 1% or more.

As the inert gas to be mixed with air or oxygen, helium, argon, neon, xenon, nitrogen or the like can be used alone or in combination, but argon, helium or nitrogen is preferable.

The operating pressure during the reaction is not particularly limited, but it is preferably carried out at atmospheric pressure or higher. This is because when the hydrosilylation reaction is performed, the platinum catalytic activity depends on the dissolved oxygen concentration in the reaction system, so when considering the explosive range in particular, when introducing a mixed gas adjusted to a predetermined oxygen concentration into the reactor. The higher the operating pressure in the gas phase, the higher the dissolved oxygen concentration in the reaction system, which can be adjusted.

[0036]

EXAMPLES Next, the method for producing the functional group-containing polymer of the present invention will be specifically described with reference to examples, but the present invention is not limited thereto. Example 1 50 g of an isobutylene polymer having a vinyl group introduced into both ends at a ratio of about 90% and a molecular weight of about 5,000 and 50 g of heptane were dissolved in a four-neck separable flask having an inner volume of 500 mL. , Platinum vinyl siloxane complex solution [xylene solution: Pt equivalent 8.3 × 10 ^-6 mmol / μL: Pt
_n (ViMe ₂ SiOSiMe ₂ Vi) _m ] is 2 × 1 with respect to the number of moles of the vinyl group contained in the isobutylene polymer.
After adjusting to 0 ^-4 mol and charging in the reactor,
The air was diluted with nitrogen and adjusted so that the oxygen concentration in the gas phase of the reactor was about 8%. However, the oxygen concentration in the gas phase and the oxygen concentration in the reaction solution were measured with a Central Scientific oxygen meter (UC-12-SOL).

Further, the temperature inside the reactor is 75 ° C. in an oil bath.
The temperature was raised with stirring so that the amount of dimethoxymethylsilane was 1.5 mol per 1 mol of the vinyl group contained in the isobutylene polymer, and the amount was introduced into the reactor through the dropping funnel.

The results are shown in FIG. 2 as the reaction rate of the change with time of the hydrosilylation reaction. Reaction rate (X)
Is an area conversion of the absorption of vinyl by FT-IR analysis (Simadzu DR-8000) and is arranged by the following equation.

X = (S−S _f ) / (S _o −S _f ) S _o : Area of vinyl peak before reaction, S _f : Area of vinyl peak at completion of reaction, S: Area of vinyl peak at completion of sampling reaction . Examples 2 to 5 Experiments were performed in the same manner as in Example 1 except that the oxygen concentration in the gas phase part was changed as shown in Table 1. The results are shown in FIG. 2 as the reaction rate of the change with time of the hydrosilylation reaction. Comparative Example 1 Except that the oxygen concentration in the gas phase was changed as shown in Table 1,
The experiment was performed in the same manner as in Example 1. The results are shown in FIG. 2 as the reaction rate of the change with time of the hydrosilylation reaction.

[0040] Examples 6 to 7 The catalyst was chloroplatinic acid (isopropyl alcohol solution: 8.
(02 × 10 ⁻⁵ mol / mL) and the hydrosilyl reaction was carried out under the same temperature and concentration conditions as in Example 1, an experiment was conducted by setting the oxygen concentration in the gas phase part as shown in Table 2. The results are shown in FIG. 3 as the reaction rate of the change with time of the hydrosilylation reaction.

[0041] Example 8 50 g of isobutylene polymer was used as a plasticizer PS-32.
(Idemitsu Kosan) Example 1 except mixing and dissolving at 25 g
The experiment was carried out under the condition. The results are shown in FIG. 4 as the reaction rate of the change with time of the hydrosilylation reaction. Comparative Example 2 Example 8 except that the oxygen concentration in the gas phase was 0.01%.
The experiment was carried out under the condition. The results are shown in FIG. 4 as the reaction rate of the change with time of the hydrosilylation reaction. Example 9 100 g of an isobutylene polymer having a vinyl group introduced into both ends at a ratio of about 95% and a molecular weight of about 10,000 and 50 g of PS-32 (Idemitsu Kosan) as a plasticizer were used.
Dissolve in a pressure resistant glass reactor with a jacket of 00 mL, and then use a platinum vinyl siloxane complex solution [xylene solution: P
t conversion 8.3 × 10 ⁻⁶ mmol / μL: Pt _n (ViMe ₂
[SiOSiMe ₂ Vi) _m ] was adjusted to be 2 × 10 ⁻⁴ mol with respect to the number of moles of vinyl groups contained in the isobutylene polymer and charged into the reactor, and then the oxygen concentration in the gas phase part of the reactor was adjusted. Was diluted with nitrogen so as to be about 8% and introduced while adjusting.

Further, the temperature inside the reactor is 75 ° C. in an oil bath.
After the temperature was raised with stirring so that the internal pressure was 0 kg / cm ² G (normal pressure) while keeping the oxygen concentration in the gas phase constant.
Adjusted to. After confirming that the state in the reactor reached a steady state, dimethoxymethylsilane was quantitatively adjusted to 1.5 mol per 1 mol of the vinyl group contained in the isobutylene polymer and reacted from the dropping funnel. It was introduced in the vessel.

The reaction results are shown in FIG. 5 as the reaction rate of the change with time of the hydrosilylation reaction. Example 10 An experiment was conducted under the conditions of Example 9 except that the oxygen concentration in the gas phase part was changed to 2 kg / cm ² G. The results are shown in FIG. 5 as the reaction rate of the change with time of the hydrosilylation reaction.

From these results, by controlling the oxygen concentration in the gas phase portion of the reactor by the method of the present invention, the oxygen concentration in the reaction solution can be efficiently controlled, and the hydrosilylation reaction activity of the platinum catalyst can be stabilized. Glue, which can be continued
It can be seen that a functional group-containing polymer useful as a raw material for an adhesive or a sealing agent can be efficiently produced.

[0045]

The effect of the present invention is evaluated by examining the production ratio of the main product and the time required for the reaction in the hydrosilylation reaction of the isobutylene polymer containing at least one alkenyl group at the terminal. can do. When the oxygen concentration in the gas phase is low, the reaction rate is extremely low and it takes an excessive amount of time to introduce the functional group.
When the introduction of a functional group is small, it is difficult to obtain a polymer having preferable physical properties. It is possible to control the reaction rate according to the oxygen concentration of the part, the amount of catalyst used, the reaction temperature, and the pressure, and to control the stable introduction of functional groups under conditions that avoid the risk of explosion, which is desirable. The functional group-containing polymer can be produced.

[Brief description of drawings]

FIG. 1 is a diagram showing a range below an explosion limit oxygen concentration of dimethoxymethylsilane.

FIG. 2 is a diagram showing an example of changes over time in a hydrosilylation reaction.

FIG. 3 is a diagram showing an example of changes over time in a hydrosilylation reaction.

FIG. 4 is a diagram showing an example of changes over time in a hydrosilylation reaction.

FIG. 5 is a diagram showing an example of changes over time in a hydrosilylation reaction.

─────────────────────────────────────────────────── ─── Continuation of the front page (56) References JP-A-7-165817 (JP, A) JP-A-1-197509 (JP, A) JP-A 64-38407 (JP, A) JP-A-3- 162405 (JP, A) JP-A-59-24704 (JP, A) JP-B-45-30833 (JP, B1) (58) Fields investigated (Int.Cl. ⁷ , DB name) C08F 8/00-8 / 50

Claims (5)

(57) [Claims] 1. A molecule having at least one alkenyl group at the end and having an average molecular weight of 1,000 to 20.
In carrying out a hydrosilylation reaction of an isobutylene-based polymer of 10,000 in the presence of a platinum catalyst, the oxygen concentration in the gas phase of the reactor is at least 0.1%, and the explosive limit oxygen concentration of the compound containing a hydrosilyl group. A method for producing a functional group-containing polymer, characterized in that the reaction is carried out under the condition of less than. 2. The method according to claim 1, wherein the reaction is carried out in the presence of a plasticizer. 3. The oxygen or air diluted with an inert gas is used as oxygen to be introduced into the reactor.
The method described in. 4. The method according to claim 1, wherein the oxygen is adjusted by the ratio of the flow rate of air or oxygen to the flow rate of the inert gas. 5. The method according to any one of claims 1 to 4, wherein the operating pressure of the gas phase portion is carried out in a pressure range of atmospheric pressure or higher.