JPH1036438A - Method for producing copolymer containing vinylcycloalkane residue - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a method for producing a vinylcycloalkane residue-containing copolymer which is excellent in transparency, heat resistance and weather resistance and is suitable as, for example, an optical material for an optical lens or an optical disk substrate. SOLUTION: The copolymer containing a vinylcycloalkane residue has a general formula (1): (In the formula, R ₁ represents a hydrogen atom or a methyl group, R ₂
Represents a cycloalkenyl group having 3 or more carbon atoms which may have a substituent)) is produced by hydrogenating a copolymer containing a vinylcycloalkene residue having a structural unit represented by the formula: The copolymer containing a vinylcycloalkene residue is represented by the general formula (2): (Wherein R ₁ and R ₂ are the same as described above), and are obtained by copolymerizing a monomer component containing a vinylcycloalkene represented by the formula ( ₁ ) and, if necessary, an unsaturated dicarboxylic acid derivative. As the vinylcycloalkene, 4-vinyl-1-
Cyclohexene is more preferred.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a method for producing a vinylcycloalkane residue-containing copolymer which is excellent in transparency, heat resistance and weather resistance and is suitable as an optical material for an optical lens or an optical disk substrate, for example. It is.

[0002]

2. Description of the Related Art Various methods have been proposed for producing polymers and copolymers (copolymers containing vinylcycloalkane residues) suitable as optical materials for optical lenses and optical disk substrates, for example. For example, JP-A-63-4391
No. 0 and JP-A-64-1706 disclose a method of hydrogenating polystyrene to obtain a vinylcyclohexane polymer. Also, Japanese Patent Application Laid-Open No. 1-132603
JP-A No. 2000-133873 discloses a method of hydrogenating a copolymer of maleic anhydride and styrene to obtain a vinylcyclohexane-based copolymer, and a method of hydrogenating a copolymer of methyl methacrylate, styrene, and maleimide to form a vinylcyclohexane-based copolymer. A method for obtaining a copolymer is disclosed.

[0003]

However, the polymers and copolymers obtained by the above-mentioned conventional methods have the problem that the transparency, heat resistance and weather resistance required when used as optical materials are insufficient. Have a point. Therefore, there is a need for a method capable of producing a copolymer excellent in transparency, heat resistance and weather resistance, that is, a copolymer containing a vinylcycloalkane residue.

The present invention has been made in view of the above-mentioned conventional problems, and has as its object the purpose of the present invention is to improve the transparency, heat resistance, and weather resistance, and to make the vinyl material suitable as an optical material such as an optical lens or an optical disk substrate. An object of the present invention is to provide a method for producing a copolymer containing a cycloalkane residue.

[0005]

Means for Solving the Problems In order to solve the above-mentioned conventional problems, the present inventors have made intensive studies on a method for producing a copolymer containing a vinylcycloalkane residue. As a result, it is possible to produce a vinylcycloalkane residue-containing copolymer having excellent transparency, heat resistance and weather resistance by hydrogenating a vinylcycloalkene residue-containing copolymer having a specific structural unit. They have found what they can do and have completed the present invention.

That is, the method for producing a vinylcycloalkane residue-containing copolymer according to the first aspect of the present invention has the following general formula (1):

[0007]

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Wherein R ₁ represents a hydrogen atom or a methyl group, and R ₂ represents a cycloalkenyl group having 3 or more carbon atoms which may have a substituent. It is characterized in that a copolymer containing a vinylcycloalkene residue is hydrogenated.

Further, in order to solve the above-mentioned problems, the method for producing a vinylcycloalkane residue-containing copolymer according to the present invention is characterized in that: The production method is characterized in that the vinylcycloalkene residue-containing copolymer further has an unsaturated dicarboxylic acid derivative residue.

According to the above method, a copolymer containing a vinylcycloalkane residue having excellent transparency, heat resistance and weather resistance can be produced. The vinylcycloalkane residue-containing copolymer can be suitably used, for example, as an optical material for an optical lens, an optical disk substrate, various optical components, and the like.

Hereinafter, the present invention will be described in detail. The method for producing a vinylcycloalkane residue-containing copolymer according to the present invention is a method for hydrogenating a vinylcycloalkene residue-containing copolymer having a structural unit represented by the general formula (1). The method for producing a vinylcycloalkane residue-containing copolymer according to the present invention is a method wherein the vinylcycloalkene residue-containing copolymer further has an unsaturated dicarboxylic acid derivative residue.

The above-mentioned copolymer containing a vinylcycloalkene residue is represented by the following general formula (2):

[0013]

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(Wherein, R ₁ represents a hydrogen atom or a methyl group, and R ₂ represents a cycloalkenyl group having 3 or more carbon atoms which may have a substituent); And, if necessary, a monomer component containing an unsaturated dicarboxylic acid derivative.

In the vinylcycloalkene represented by the general formula (2), the substituent represented by R ₁ is a hydrogen atom or a methyl group, and the substituent represented by R ₂ is further substituted. Any cycloalkenyl group having 3 or more carbon atoms which may have a substituent may be used, and is not particularly limited, but a compound having 8 or less carbon atoms in the cycloalkenyl group is more preferable.

The "cycloalkenyl group" in the present invention includes a cycloalkadienyl group having two double bonds, a cycloalkatrienyl group having three double bonds, and the like. That is, the “cycloalkenyl group” in the present invention represents a cyclic unsaturated hydrocarbon monovalent group having at least one double bond. However,
The unsaturated hydrocarbon monovalent group does not include an aromatic hydrocarbon monovalent group.

As the vinylcycloalkene, specifically, for example, 1-vinyl-1-cyclopropene, 3-vinyl-1-cyclopropene, 1-vinyl-1-cyclobutene, 3-vinyl-1-cyclobutene, 1-vinyl-1
-Cyclopentene, 3-vinyl-1-cyclopentene,
4-vinyl-1-cyclopentene, 1-vinyl-1-cyclohexene, 3-vinyl-1-cyclohexene, 4-
Vinyl-1-cyclohexene, 1-vinyl-1-cycloheptene, 3-vinyl-1-cycloheptene, 4-vinyl-1-cycloheptene, 5-vinyl-1-cycloheptene, 1-isopropenyl-1-cyclohexene, 3-
Isopropenyl-1-cyclohexene, 4-isopropenyl-1-cyclohexene, each isomer of vinylmethylcyclohexene, each isomer of vinylbutylcyclohexene, each isomer of vinyldimethylcyclohexene, each isomer of vinylchlorocyclohexene, 1- Vinyl-1,3
-Cyclopentadiene, 2-vinyl-1,3-cyclopentadiene, 5-vinyl-1,3-cyclopentadiene, and isomers of vinylcyclohexadiene. One of these vinylcycloalkenes may be used alone, or two or more thereof may be used in combination. Among the compounds exemplified above, 4-vinyl-1-cyclohexene is more preferred. The proportion of vinylcycloalkene in the monomer component is preferably in the range of 5% by weight to 95% by weight, and more preferably in the range of 10% by weight to 75% by weight.
When the proportion of the vinylcycloalkene is out of the above range, it is not preferable because a copolymer containing a vinylcycloalkane residue having excellent transparency, heat resistance and weather resistance cannot be obtained.

The above-mentioned unsaturated dicarboxylic acid derivative optionally used includes maleic anhydride and a maleimide monomer. Specific examples of the maleimide-based monomer include, for example, maleimide; N-methylmaleimide, N-ethylmaleimide, Nn-propylmaleimide, N-isopropylmaleimide, N-butylmaleimide, N-phenylmaleimide, N-substituted maleimides such as-(methylphenyl) maleimide, N- (methoxyphenyl) maleimide, N- (carboxyphenyl) maleimide, N-cyclohexylmaleimide, N- (chlorophenyl) maleimide, N- (bromophenyl) maleimide; No.

One of these unsaturated dicarboxylic acid derivatives may be used alone, or two or more thereof may be used in combination. Among the compounds exemplified above, N-phenylmaleimide and N-cyclohexylmaleimide are more preferable from the viewpoints of availability, economy, and the like. When the unsaturated dicarboxylic acid derivative is used, the ratio of the unsaturated dicarboxylic acid derivative in the monomer component is from 5% by weight to 95% by weight.
%, More preferably in the range of 25% to 90% by weight. If the proportion of the unsaturated dicarboxylic acid derivative exceeds 95% by weight, a vinylcycloalkane residue-containing copolymer excellent in transparency, heat resistance and weather resistance cannot be obtained, which is not preferred.

The above-mentioned monomer component may contain a vinylcycloalkene and, if necessary, an unsaturated dicarboxylic acid derivative. May be included (hereinafter, referred to as a vinyl monomer). As the vinyl monomer, specifically, for example, acrylic acid,
Methacrylic acid, itaconic acid, acrylonitrile, methacrylonitrile; methyl acrylate, ethyl acrylate,
Propyl acrylate, butyl acrylate, acrylic acid-
Alkyl acrylates such as 2-ethylhexyl, cyclohexyl acrylate, methyl cyclohexyl acrylate, tert-butylcyclohexyl acrylate; methyl methacrylate, ethyl methacrylate, propyl methacrylate, butyl methacrylate, 2-ethylhexyl methacrylate; Methacrylic acid alkyl esters such as cyclohexyl methacrylate, methylcyclohexyl methacrylate, and t-butylcyclohexyl methacrylate; α-olefins such as ethylene, propylene, isobutene and 4-methyl-1-pentene; diolefins such as butadiene and isoprene; Vinylcyclopropane, vinylcyclobutane, vinylcyclopentane, vinylcyclohexane,
Vinylcycloalkanes such as vinylcycloheptane, isopropenylcyclohexane, isomers of vinylmethylcyclohexane, isomers of vinylbutylcyclohexane, isomers of vinyldimethylcyclohexane, and isomers of vinylchlorocyclohexane; and the like. ,
There is no particular limitation. These vinyl monomers are
Only one type may be used, or two or more types may be used in combination. The type and amount of the vinyl monomer may be appropriately set according to the desired physical properties and the like of the obtained vinylcycloalkane residue-containing copolymer.

The method for copolymerizing the monomer components is not particularly limited, and conventionally known polymerization methods, for example,
Bulk polymerization, solution polymerization, suspension polymerization, emulsion polymerization and the like can be employed.

When copolymerizing the monomer components, a solvent can be used if necessary. The solvent is not particularly limited as long as it is a compound capable of dissolving the monomer component. As the solvent, specifically, for example, saturated hydrocarbons such as hexane, heptane, octane, and cyclohexane; butyl alcohol, heptyl alcohol, octyl alcohol, nonyl alcohol,
Alcohols such as decyl alcohol; ketones such as methyl ethyl ketone and methyl isobutyl ketone; ethers such as tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and ethyl benzene;
Halogenated hydrocarbons such as chloroform and carbon tetrachloride; and the like. These solvents may be used alone or as a mixture of two or more. Among the solvents exemplified above, aromatic hydrocarbons are more preferred. The amount of the solvent used may be appropriately set according to the composition of the monomer component, the reaction conditions, and the like, and is not particularly limited.

When copolymerizing the monomer components, a polymerization initiator is used. As the polymerization initiator, specifically, for example, cumene hydroperoxide, diisopropylbenzene hydroperoxide, di-t-butyl peroxide, p-menthane hydroperoxide, lauroyl peroxide, benzoyl peroxide,
t-butyl peroxy isopropyl carbonate,
1,1-bis (t-butylperoxy) -3,3,5-
Organic peroxides such as trimethylcyclohexane, di-t-butylperoxy hexahydroterephthalate, t-butylperoxy-2-ethylhexanoate; ammonium persulfate, potassium persulfate, sodium persulfate, hydrogen peroxide, etc. Inorganic peroxide; 2,2′-azobisisobutyronitrile, 2,2′-azobis (4-methoxy-
Radical polymerization initiators such as 2,4-dimethylvaleronitrile), azo compounds such as 1,1′-azobis (cyclohexane-1-carbonitrile) and azobenzene; and the like, but are not particularly limited. One of these polymerization initiators may be used alone, or two or more thereof may be used in combination. Further, the peroxide, a sulfite,
A redox initiator can also be used in combination with a reducing agent such as bisulfite, thiosulfate, formamidine sulfinic acid, and ascorbic acid. The amount of the polymerization initiator to be used may be appropriately set according to the composition of the monomer component, the reaction conditions, and the like, and is not particularly limited.

The reaction conditions for copolymerizing the monomer component may be appropriately set according to the composition of the monomer component and the like.
Although not particularly limited, the reaction temperature is 90 ° C.
A temperature in the range of 150 ° C. is preferred. The reaction time may be appropriately set according to the composition of the monomer components, the amount of the polymerization initiator used, the reaction temperature, and the like, but is preferably about 1 hour to 24 hours. In addition, in order to remove the vinylcycloalkene residue-containing copolymer from the solvent, that is, the reaction solution, for example, the reaction solution is poured into a large excess of alcohol to precipitate the vinylcycloalkene residue-containing copolymer. What is necessary is just to employ | adopt the so-called alcohol coagulation method; the so-called solvent removal method which removes a solvent using an extruder;

By copolymerizing the above monomer components, a copolymer containing a vinylcycloalkene residue can be obtained. That is, from the vinylcycloalkene represented by the general formula (2), a corresponding structural unit represented by the general formula (1), that is, a vinylcycloalkene residue is formed, while an unsaturated dicarboxylic acid derivative is formed. Form the corresponding unsaturated dicarboxylic acid derivative residue. Incidentally, a corresponding vinyl monomer residue is formed from the vinyl monomer.

The copolymer having a vinylcycloalkene residue preferably has a glass transition temperature (Tg) of from 120 ° C. to 2 ° C.
The temperature is 50 ° C, more preferably 150 ° C to 220 ° C. The weight average molecular weight (Mw) of the copolymer containing a vinylcycloalkene residue is preferably in the range of 1,000 to 500,000, and more preferably in the range of 1,000 to 100,000. If the weight average molecular weight is outside the above range, it is not preferable because a vinylcycloalkane residue-containing copolymer excellent in transparency, heat resistance and weather resistance cannot be obtained.

The method for hydrogenating the vinylcycloalkene residue-containing copolymer is not particularly limited, and various conventionally known methods such as a method using an autoclave can be employed.

When hydrogenating a copolymer containing a vinylcycloalkene residue, a hydrogenation catalyst is used. The hydrogenation catalyst is not particularly limited, but is preferably a carrier obtained by supporting a metal such as palladium, ruthenium, rhodium, and platinum on a carrier such as carbon. The amount of the metal supported on the support is not particularly limited, but is more preferably in the range of 0.05% by weight to 20% by weight. The amount of the hydrogenation catalyst used may be appropriately set according to the type of the vinylcycloalkene residue-containing copolymer, the reaction conditions and the like, and is not particularly limited.

When hydrogenating the copolymer containing a vinylcycloalkene residue, a solvent can be used, if necessary. The solvent is not particularly limited as long as it is a compound that can dissolve the vinylcycloalkene residue-containing copolymer and does not inhibit hydrogenation. As the solvent, all compounds generally used for hydrogenation can be used. Specifically, for example,
Ketones such as methyl ethyl ketone and methyl isobutyl ketone; ethers such as tetrahydrofuran and dioxane; halogenated hydrocarbons such as chloroform and carbon tetrachloride; These solvents may be used alone or as a mixture of two or more.
The amount of the solvent used is not particularly limited, and may be appropriately set according to the type of the vinylcycloalkene residue-containing copolymer, the reaction conditions, and the like.

The reaction conditions for hydrogenating the vinylcycloalkene residue-containing copolymer, that is, the hydrogen pressure, reaction temperature, reaction time, etc., depend on the type of the vinylcycloalkene residue-containing copolymer. The hydrogen pressure may be appropriately set and is not particularly limited, but the hydrogen pressure is 5 kg / cm ^{2 to} 150 k.
g / cm ² is preferred. The reaction temperature is
It is preferably in the range of 50C to 250C, and 90C to 150C.
It is more preferable to be within the range of ° C.

By hydrogenating a copolymer containing a vinylcycloalkene residue, the copolymer containing a vinylcycloalkane residue according to the present invention can be produced. still,
The hydrogenation catalyst can be easily removed by filtration. Further, in order to separate the obtained vinylcycloalkane residue-containing copolymer and the solvent, for example, the vinylcycloalkane residue-containing copolymer is precipitated by pouring the reaction solution into a large excess of alcohol, What is necessary is just to employ | adopt the so-called alcohol coagulation method; the so-called solvent removal method which removes a solvent using an extruder;

As described above, the method for producing a vinylcycloalkane residue-containing copolymer according to the present invention comprises the step of converting a vinylcycloalkene residue-containing copolymer having a structural unit represented by the above general formula (1) to hydrogen. It is a method to become. Further, as described above, the method for producing a vinylcycloalkane residue-containing copolymer according to the present invention is a method wherein the vinylcycloalkene residue-containing copolymer further has an unsaturated dicarboxylic acid derivative residue. .

According to the above method, a copolymer containing a vinylcycloalkane residue excellent in transparency, heat resistance and weather resistance can be produced. The vinylcycloalkane residue-containing copolymer can be suitably used, for example, as an optical material for an optical lens, an optical disk substrate, various optical components, and the like. Incidentally, the copolymer containing a vinylcycloalkane residue can be easily molded by a known molding method such as extrusion molding, injection molding, and compression molding.

The copolymer containing a vinylcycloalkane residue may optionally contain an antioxidant, a release agent, a plasticizer,
Fluidity improvers, heat stabilizers, light fastness stabilizers, antistatic agents,
Various additives such as a coloring agent may be included. In addition, the addition amount of these additives is not particularly limited.

The vinylcycloalkane residue-containing copolymer obtained by the above production method has compatibility with synthetic resins. The above synthetic resin is not particularly limited, and any conventionally known synthetic resin, that is, a thermoplastic resin and a thermosetting resin can be employed. As the thermoplastic resin, specifically, for example, polymethyl methacrylate, polystyrene, AS (acrylonitrile-styrene) resin, polycarbonate and the like are particularly suitable. As the thermosetting resin, specifically, for example, an epoxy resin, an unsaturated polyester resin, an alkyd resin, a polyurethane or the like is suitable. In addition, only one type of synthetic resin may be used, or two or more types may be used in combination.

The method of mixing the synthetic resin and the vinylcycloalkane residue-containing copolymer is not particularly limited. For example, the method of mixing the synthetic resin and the vinylcycloalkane residue-containing copolymer with an appropriate solvent The solution is poured into a large excess of alcohol to cause a mixture to precipitate, a so-called alcohol coagulation method; kneading a synthetic resin and a vinylcycloalkane residue-containing copolymer using an extruder, so-called A kneading method may be employed. Since the synthetic resin and the vinylcycloalkane residue-containing copolymer are compatible with each other, they are uniformly mixed by forming the mixture.

The solvent is not particularly limited as long as it is a compound capable of dissolving the synthetic resin and the copolymer containing a vinylcycloalkane residue. Specific examples of the solvent include the solvents exemplified above. The weight ratio of the synthetic resin to the vinylcycloalkane residue-containing copolymer (synthetic resin / copolymer) is not particularly limited, but is preferably in the range of 1/99 to 99/1, and is preferably 10/99. More preferably, it is in the range of 90 to 90/10.

Incidentally, vinylcycloalkane, which is a hydride of vinylcycloalkene represented by the general formula (2), is generally very expensive and has low purity as compared with the vinylcycloalkene. Therefore, when a vinylcycloalkane residue-containing copolymer is produced by copolymerizing a monomer component containing the vinylcycloalkane,
The resulting vinylcycloalkane residue-containing copolymer is very expensive and of low quality. In other words, by employing the production method according to the present invention, an inexpensive and high-quality copolymer containing a vinylcycloalkane residue can be industrially obtained.

[0039]

EXAMPLES The present invention will be described in more detail with reference to the following Examples, but it should not be construed that the invention is limited thereto. In the examples, "parts" means "parts by weight".
Is shown.

Example 1 A 1 L flask equipped with a reflux condenser, a nitrogen gas inlet tube, a thermometer, and a stirrer was used as a reaction vessel. In this reaction vessel, 4-vinyl-1-cyclohexene 25 as a vinylcycloalkene was added.
Part, unsaturated dicarboxylic acid derivative (maleimide monomer)
Was charged with 25 parts of N-cyclohexylmaleimide, 50 parts of toluene as a solvent, and 0.33 part of Kayacaron BIC-75 (trade name; manufactured by Kayaku Akzo Co., Ltd.) as a polymerization initiator. The gas was replaced.
Therefore, the monomer component is composed of 4-vinyl-1-cyclohexene and N-cyclohexylmaleimide.

Then, the content was heated to 110 ° C. while stirring the above contents under a nitrogen gas stream, and a polymerization reaction was carried out for 8 hours while maintaining the temperature. After completion of the reaction, the reaction solution was cooled and the reaction solution was poured into a large excess of methyl alcohol to precipitate a copolymer (4-vinyl-1-cyclohexene / N-cyclohexylmaleimide copolymer). Thereafter, the copolymer was filtered out and dried. Thus, a copolymer containing a vinylcycloalkene residue was obtained.

The amount of the obtained copolymer containing a vinylcycloalkene residue was 17.7 parts.
-77% by weight of a structural unit consisting of cyclohexylmaleimide (residue of an unsaturated dicarboxylic acid derivative). FIG. 1 shows a chart of an infrared absorption spectrum of the copolymer containing a vinylcycloalkene residue. FIG. 2 is a chart of ¹ H-NMR of the copolymer containing a vinylcycloalkene residue.
Shown in As a result of measuring GPC (gel permeation chromatography), the weight average molecular weight (Mw) of the vinylcycloalkene residue-containing copolymer was 7,700 in terms of polystyrene. As a result of a thermal analysis, the glass transition temperature of the copolymer containing a vinylcycloalkene residue was 195 ° C.

Subsequently, the above-mentioned vinylcycloalkene residue-containing copolymer 10 was placed in a 1 L autoclave equipped with a hydrogen gas inlet tube, a thermometer, a pressure gauge and a stirrer.
, 5 parts by weight of palladium-carbon as a hydrogenation catalyst, and 90 parts of tetrahydrofuran as a solvent were charged and sealed. Next, in order to maintain the pressure (hydrogen pressure) in the autoclave at 20 kg / cm ² (gauge pressure), the mixture was stirred at 120 ° C. for 4 hours while supplying hydrogen gas to the autoclave through a hydrogen gas introduction pipe, and hydrogenated. Was done.

After the completion of the hydrogenation, the reaction solution was cooled, and the reaction solution was filtered to remove 5% by weight of palladium-carbon.
Next, the copolymer was precipitated by pouring the filtrate into a large excess of methyl alcohol. Thereafter, the copolymer was filtered out and dried. Thus, a copolymer containing a vinylcycloalkane residue according to the present invention was obtained.

[0045] The ¹ H-NMR of the obtained vinyl cycloalkane residue-containing copolymer was measured, the results were compared with the chart, a ¹ H-NMR chart of a vinyl cycloalkene residue-containing copolymer, the The hydrogenation rate by hydrogenation is 99
%Met.

Further, a copolymer containing a vinylcycloalkane residue is dissolved in chloroform so as to have a predetermined concentration.
By casting (coating) the obtained chloroform solution on a glass plate, a film composed of a copolymer containing a vinylcycloalkane residue was prepared. The obtained film was colorless and transparent, and was excellent in transparency, heat resistance, weather resistance and fluidity.

[0047]

The method for producing a vinylcycloalkane residue-containing copolymer according to claim 1 of the present invention is as described above.
General formula (1)

[0048]

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(Wherein, R ₁ represents a hydrogen atom or a methyl group, and R ₂ represents a cycloalkenyl group having 3 or more carbon atoms which may have a substituent). This is a method for hydrogenating a copolymer containing a vinylcycloalkene residue.

According to the method for producing a vinylcycloalkane residue-containing copolymer according to claim 2 of the present invention, as described above, the vinylcycloalkene residue-containing copolymer has an unsaturated dicarboxylic acid derivative residue. It is also a method to have.

This has the effect of producing a vinylcycloalkane residue-containing copolymer having excellent transparency, heat resistance and weather resistance. The vinylcycloalkane residue-containing copolymer can be suitably used, for example, as an optical material for an optical lens, an optical disk substrate, various optical components, and the like.

[Brief description of the drawings]

FIG. 1 is a chart of an infrared absorption spectrum of a copolymer containing a vinylcycloalkene residue obtained in one example of the present invention.

FIG. 2 shows the copolymer of the above vinylcycloalkene residue.
It is a chart of < ¹ > H-NMR.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁶ Identification number Agency reference number FI Technical display location G11B 7/135 G11B 7/135 A 7/24 526 8721-5D 7/24 526N // (C08F 210 / 14 222: 40)

Claims (2)

[Claims] 1. A compound of the general formula (1) (In the formula, R ₁ represents a hydrogen atom or a methyl group, R ₂
Represents a cycloalkenyl group having 3 or more carbon atoms which may have a substituent), wherein a vinylcycloalkene residue-containing copolymer having a structural unit represented by the formula: is hydrogenated. A method for producing a residue-containing copolymer. 2. The process for producing a vinylcycloalkane residue-containing copolymer according to claim 1, wherein the vinylcycloalkene residue-containing copolymer further has an unsaturated dicarboxylic acid derivative residue.