JPH04363312A - Hydrogenated thermoplastic norbornene polymer, method for producing the same, optical element substrates, optical elements, and lenses molded from the same - Google Patents

Abstract

PURPOSE:To provide a hydrogenated thermoplastic saturated norbornene polymer having excellent transparency and adhesivity to metal film. CONSTITUTION:The objective hydrogenated thermoplastic norbornene polymer contains <=1ppm of pigment of transition metal atom originated from polymerization catalyst. It can be produced by hydrogenating a thermoplastic norbornene polymer containing polymerization catalyst residue using a heterogeneous catalyst having a pore volume of >=0.5 cm<3>/g and obtained by supporting a catalytic metal on an adsorbent, removing the hydrogenation catalyst and recovering the obtained hydrogenated thermoplastic norbornene polymer.

Description

[Detailed description of the invention]

0001

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a hydrogenated thermoplastic norbornene polymer, a method for producing the same, and optical element substrates, optical elements, and lenses molded from the same. More specifically, the content of transition metal atoms derived from the polymerization catalyst is 1p.
Thermoplastic norbornene-based polymer hydrogenated product of pm or less,
The present invention relates to a method for manufacturing the same, an optical element substrate formed by molding the same, an optical element, and a lens.

0002

[Prior Art] In recent years, materials with high light transmittance have been required as optical materials, especially as materials for lenses.
Wavelength 400-70 when made into an injection molded product with a thickness of 3 mm
It is said that it is preferable to have a light transmittance of 90% or more in the entire range of 0 nm. In other words, if the light transmittance is poor in some visible light rays, the lens will be colored, and
When used near a strong light source, the light energy of that wavelength is absorbed and converted into heat, resulting in a high temperature, which creates a risk of melting even if the material has a certain degree of heat resistance.

Polymethyl methacrylate (PMMA) and polycarbonate (PC) have been known as optical materials. Among these, PMMA has excellent transparency,
The light transmittance of an injection molded article with a thickness of 3 mm reached 90% at a wavelength of 430 nm and 91% at a wavelength of 700 nm, but there were problems in terms of heat resistance and moisture resistance. Also, PC has better heat resistance and moisture resistance than PMMA, but
There was a problem that the light transmittance at 30 nm was about 86% at most, and the birefringence was large.

[0004] In recent years, hydrogenated thermoplastic norbornene polymers have attracted attention as optical materials with excellent heat resistance, moisture resistance, and low birefringence. However, when injection molding a molded article with a thickness of 3 mm using a hydrogenated thermoplastic norbornene polymer produced by a conventional method, the light transmittance at a wavelength of 700 nm is 90% or more, but the light transmittance at a wavelength of 430 nm is 90%. Only less than % was obtained. Furthermore, even if an information medium optical element is manufactured by depositing a metal film on a substrate formed from the hydrogenated material, the adhesion with the metal film may not be sufficient, such as blistering under high temperature and high humidity conditions. There was a desire for improvement.

As described below, the present inventors have found that the transparency and adhesion to metal films of thermoplastic norbornene-based polymer hydrogenated polymers can be improved by reducing the concentration of transition metal atoms, which are polymerization catalyst residues. I found out that. The conventional method of washing the polymer with a poor solvent and the method of treating the polymerization reaction solution with an adsorbent such as activated alumina or zeolite in the presence of a compound having a hydroxyl group (Japanese Patent Application Laid-Open No. 3-66725
Even if the polymerization catalyst residue is removed using No. 1), the concentration of transition metal atoms that are polymerization catalyst residue in the treated polymer is about 2 ppm or more, and the concentration of transition metal atoms derived from the polymerization catalyst is 1 ppm or less. Hydrogenated thermoplastic norbornene polymers were not known.

[0006] The use of a heterogeneous catalyst for the hydrogenation reaction of thermoplastic norbornene polymers is disclosed in Japanese Patent Application Laid-Open No. 1-3111.
No. 20, JP-A No. 3-66725, etc. Examples of carriers include carbon, silica, alumina, and titania. However, many of the supports conventionally used lack sufficient pore volume and specific surface area to provide adsorption performance. There were no known examples of using catalysts.

[0007]

[Problems to be Solved by the Invention] As a result of intensive research into the problems of transparency and adhesion with metal films of thermoplastic norbornene-based polymer hydrogenates, the present inventors have found that The trace amounts of transition metal atoms derived from the polymerization catalyst that remain have an adverse effect on the transparency and adhesion with the metal film, and the transition metal atoms are responsible for supporting the catalyst metal on the adsorbent during the hydrogenation reaction of the polymer. Pore volume 0.5cm3/
It can be easily removed by using a heterogeneous catalyst with a weight of 1 ppm or more, and the content of transition metal atoms derived from the polymerization catalyst is 1 ppm.
It was discovered that the following thermoplastic norbornene-based polymer hydrogenated product could be obtained, and the present invention was completed.

[0008]

[Means for Solving the Problems] According to the present invention, there is provided a hydrogenated thermoplastic norbornene polymer having a content of transition metal atoms derived from a polymerization catalyst of 1 ppm or less, a method for producing the same, and a method for molding the hydrogenated product. An optical element substrate, an optical element, and a lens are provided.

(Thermoplastic norbornene polymer) In the present invention, the thermoplastic norbornene polymer contains a polymerization catalyst used in polymerizing monomers as an impurity. Specific examples of the polymer include ring-opening polymers of norbornene monomers, addition polymers of norbornene monomers, and addition polymers of norbornene monomers and olefins.

Examples of norbornene monomers include:
Norbornene and its alkyl and/or alkylidene substituents, such as 5-methyl-2-norbornene, 5-dimethyl-2-norbornene, 5-ethyl-2
-norbornene, 5-butyl-2-norbornene, 5-
Ethylidene-2-norbornene, etc., substituted with polar groups such as halogen; dicyclopentadiene, 2,3-dihydrodicyclopentadiene, etc.; dimetanooctahydronaphthalene, its alkyl and/or alkylidene substituted products, and halogen, etc. Polar group substituents, such as 6-
Methyl-1,4:5,8-dimethano-1,4,4a,5
, 6,7,8,8a-octahydronaltalene, 6-ethyl-1,4:5,8-dimethano-1,4,4a,5,
6,7,8,8a-octahydronaphthalene, 6-ethylidene-1,4:5,8-dimethano-1,4,4a,5
, 6,7,8,8a-octahydronaphthalene, 6-chloro-1,4:5,8-dimethano-1,4,4a,5,
6,7,8,8a-octahydronaphthalene, 6-cyano-1,4:5,8-dimethano-1,4,4a,5,6
,7,8,8a-octahydronaphthalene, 6-pyridyl-1,4:5,8-dimethano-1,4,4a,5,6
,7,8,8a-octahydronaphthalene, 6-methoxycarbonyl-1,4:5,8-dimethano-1,4,4
a,5,6,7,8,8a-octahydronaphthalene, etc.; cyclopentadiene trimer-tetramer, e.g. 4,9:
5,8-dimethano-3a,4,4a,5,8,8a,9
,9a-octahydro-1H-benzoindene, 4,1
1:5, 10:6,9-trimethano-3a,4,4a,
5, 5a, 6, 9, 9a, 10, 10a, 11, 11a
-dodecahydro-1H-cyclopentaanthracene; and the like.

(Polymerization method) Ring-opening polymerization of norbornene monomers is usually carried out using a catalyst consisting essentially of a transition metal compound and an organometallic compound of a metal of Groups I to IV of the periodic table. Examples of transition metal compounds include halides, oxyhalides, and oxides of transition metals such as titanium, molybdenum, and tungsten.
Cl4, TiBr4, WBr4, WCl6, WOF4,
Examples include MoBr2, MoCl5, MoOF4. In addition, as organometallic compounds of group I to IV metals,
Examples include organoaluminum compounds and organotin compounds, specifically trimethylaluminum, triphenylaluminum, ethylaluminum sesquichloride,
Examples include tetrabutyltin, diethyltin diiodide, n-butyllithium, diacylzinc, and trimethylboron.

[0012] In addition-type polymerization of norbornene-based monomers or addition-type polymerization of norbornene-based monomers and olefins, ring-opening polymerization may be carried out by a known method using a known transition metal catalyst. Usually, a catalyst formed from a titanium compound or vanadium compound supported on a magnesium compound and an alkyl aluminum compound is used. The titanium compound or vanadium compound supported on the magnesium compound is a composite containing at least magnesium, titanium, and halogen, and its manufacturing method is described, for example, in JP-A-48-16986.
No., JP-A-51-20297, JP-A-52-8748
No. 9, Japanese Unexamined Patent Publication No. 53-2580, etc. Vanadium compounds include VCl4, VOBr2, V
O(OCH3)2Cl, VO(OC3H7)3, VO(
Examples include OC4H9)Cl2 and mixtures thereof. Examples of alkyl aluminum compounds include trialkyl aluminum, dialkyl aluminum halide,
Examples include alkyl aluminum dihalides and mixtures thereof.

[0013] After the polymerization has progressed to a molecular weight suitable for the purpose, the polymerization is stopped. To stop the polymerization, the polymerization catalyst is inactivated and then removed. In order to deactivate the polymerization catalyst, for example, a catalyst deactivator such as water or alcohol may be added to the polymerization reaction solution. This causes the polymerization catalyst to precipitate out, but if it is refluxed, the precipitated polymerization catalyst becomes hard and large lumps, making it easier to remove. To remove the polymerization catalyst, for example, the inactivated and precipitated polymerization catalyst may be removed by centrifugation or filtration, or the polymerization reaction solution after the reaction has been stopped may be washed with a large amount of poor solvent. Alternatively, the polymerization reaction solution may be treated with an adsorbent such as activated alumina or zeolite in the presence of a compound having a hydroxyl group. Removal by these methods usually leaves about 2 to 10 ppm of transition metal atoms derived from the polymerization catalyst.

(Hydrogenation reaction) Thermoplastic norbornene-based polymers are produced by saturating the olefinically unsaturated groups in their molecules, that is, the double bonds in the main chain and the double bonds in the unsaturated rings. It can be a polymeric hydrogenated product.

The hydrogenation catalyst is not particularly limited as long as it is a heterogeneous catalyst that can be used for hydrogenation of olefin compounds and has a pore volume of 0.5 cm 3 /g or more, in which a catalytic metal is supported on an adsorbent. The adsorbent referred to in the present invention has the ability to adsorb polymerization catalyst residue, gelled resin, and the like. For example, the heterogeneous catalyst used in the present invention has a pore volume of 0.5 cm3/g or more, preferably 0.7 c
m3/g or more, and preferably a specific surface area of 250 m2/g
Examples include those in which the above-mentioned magnesia, activated alumina, synthetic zeolite, etc. support a catalytic metal. Activated alumina, synthetic zeolite, etc. are preferable because they have excellent adsorption ability for polymerization catalyst residues, gelled resin, etc. Among them, activated alumina is particularly preferable because it maintains high activity with less decrease in catalyst activity due to adsorption of impurities. Examples of the catalytic metal include nickel, palladium, platinum, and the like.

The method for producing the heterogeneous catalyst may be according to a known method, as described in Japanese Patent Publication Nos. 15474-1982 and 3rd Edition of Japanese Patent Publication No. 1983-1983.
No. 2187, Special Publication No. 11312, Special Publication No. 11312, Special Publication No. 1971-
According to No. 48479 etc., depending on the drying and firing conditions,
The adsorption capacity of the carrier may be controlled. For example, in the case of a heterogeneous catalyst in which nickel is supported on activated alumina, the concentration is 10~
Aluminum hydroxide powder is suspended in a 20% nickel sulfate or nickel nitrate aqueous solution at a concentration of 10 to 20%, and then hydrolyzed with sodium hydroxide to support nickel hydroxide on the surface of the aluminum hydroxide. This powder was collected by filtration, solidified by extrusion, and
Calcinate at 450°C, reduce the surface by contacting with hydrogen at 100-200°C, and further heat at 80-120°C in the presence of oxygen.
By heating the metal surface to oxidize and form an oxide film, a nickel catalyst supported on activated alumina can be obtained. Note that the surface of nickel is covered with nickel oxide, but in the hydrogenation reaction system, nickel oxide becomes nickel due to reduction and functions as a catalyst.

Since the fine structure of activated alumina changes depending on extrusion conditions, firing temperature and pressure, etc., the pore volume is 0.5 cm3/g or more, preferably 0.7 cm3/g.
The conditions are preferably selected so that the specific surface area is 250 m2/g or more. Furthermore, in the case of hydrogenation at a high temperature, the thicker the oxide film, the more heat resistant it is, so preferred conditions may be selected by adjusting the oxidation temperature, time, oxygen concentration, etc. The thus obtained calcined product is pulverized to obtain a heterogeneous catalyst.

The hydrogenation reaction of the thermoplastic norbornene polymer in the present invention is usually carried out in an inert organic solvent. As the organic solvent, hydrocarbon solvents are preferred;
Among these, cyclic hydrocarbon solvents are particularly preferred since they have excellent solubility for the norbornene polymer produced. Specific examples include aromatic hydrocarbons such as benzene and toluene, aliphatic hydrocarbons such as n-pentane and hexane, cyclohexane,
Examples include alicyclic hydrocarbons such as decalin, halogenated hydrocarbons such as methylene dichloride, dichloroethane, etc., and two or more of these can also be used in combination. When a solvent is used, the amount of the solvent used is 1 to 20 parts by weight, preferably 1 to 20 parts by weight, per 1 part by weight of the norbornene polymer.
It is 10 parts by weight.

The hydrogenation reaction is carried out under a hydrogen pressure of 1 to 150 atmospheres and at a temperature of 0 to 280°C, preferably 20 to 230°C, depending on the type of heterogeneous catalyst. When synthetic zeolite or activated alumina is used, from the viewpoint of reaction efficiency, the higher the temperature, the more the reaction progresses. Especially when using nickel supported on activated alumina, the temperature is preferably 200 to 250°C, and 220 to 250°C. 230°C is more preferred. The hydrogenation rate can be arbitrarily adjusted by changing hydrogen pressure, reaction temperature, reaction time, catalyst concentration, etc.

(Removal of Catalyst) The heterogeneous catalyst may be removed by conventional methods such as centrifugation and filtration. Centrifugation and filtration methods can be used under conditions that allow removal of the heterogeneous catalyst used.
Not particularly limited. Removal by oxidation is preferred because it is simple and efficient. When filtering, pressure filtration or suction filtration may be used, and from the viewpoint of efficiency, it is preferable to use a filter aid such as diatomaceous earth or perlite.

Furthermore, the heterogeneous catalyst which is a hydrogenation catalyst has a particle size of 0.2 μm or more, that is, a particle size of 0.2 μm or more.
When using a material that does not substantially contain anything less than 2 μm,
This is preferred because the heterogeneous catalyst can be easily removed by filtration. If the particle size is too small, it will easily leak during filtration, and it will be difficult to remove even by centrifugation. Become. In addition, if a filter with a small pore size is used to prevent leakage, clogging is likely to occur, resulting in poor work efficiency.

(Thermoplastic norbornene-based polymer hydrogenated product) The thermoplastic norbornene-based polymer hydrogenated product of the present invention has the same properties as conventional thermoplastic norbornene-based polymer hydrogenated products such as heat resistance, heat deterioration resistance, and light resistance. Not only does it have excellent deterioration resistance, moisture resistance, and chemical resistance, but it also has a low content of transition metal atoms, with the content of transition metal atoms derived from the polymerization catalyst being 1p.
pm or less. Due to the small content of transition metal atoms, the thermoplastic norbornene-based polymer hydrogenated product of the present invention has excellent transparency compared to conventional ones, and also has, for example,
In information recording medium optical elements having metal reflective films, metal recording films, etc., which will be described later, have good adhesion to metal films, etc., such that blistering does not occur even under high temperature and high humidity conditions.

(Additives) The hydrogenated thermoplastic norbornene polymer of the present invention may contain well-known additives, such as antioxidants, light stabilizers, ultraviolet absorbers, lubricants,
It can be used as a resin composition by blending plasticizers, flame retardants, antistatic agents, heat stabilizers, hydrogenated petroleum resins, dyes, pigments, inorganic and organic fillers, and the like.

(Molding Process) The hydrogenated thermoplastic norbornene polymer of the present invention can be molded into an optical element substrate by a conventional method. The molding method is not particularly limited, and ordinary plastic molding methods such as injection molding, extrusion molding, and compression molding can be applied.

An information recording medium optical element is obtained by forming an information recording film layer on the optical element substrate obtained by molding. As the information recording film layer, a metal film is usually used as a metal reflective film or a metal recording film, and an information recording medium element optical element, such as an optical recording medium disk or an optical recording medium card, is manufactured. The formation of a metal reflective film is carried out by depositing a metal with high reflectance, such as nickel, aluminum, gold, etc., and in the case of a metal recording film,
This is carried out by depositing a general Tb-Fe-Co alloy or the like as a magneto-optical recording film. The method of vapor deposition of the metal film onto the optical element substrate is not particularly limited either, and ordinary vapor deposition methods such as vacuum vapor deposition, sputtering, etc. can be applied.

[0026] Also, known injection molding methods, such as Japanese Patent Application Laid-open No. 6
Plastic lenses can also be molded according to methods such as JP-A No. 0-141518, JP-A-60-225722, and JP-A-61-144316.

In addition, an optical element, such as a Fresnel lens, can be manufactured by bonding an optical element pattern to an optical element substrate using a known method.

[0028]

[Example] The present invention will be explained in more detail by referring to Reference Examples, Examples, and Comparative Examples below.

Reference Example 1 6-ethyl-1,4:5,8-dimethano-1,4,4a
,5,6,7,8,8a-octahydronaphthalene 60
Part by weight was dissolved in 200 parts by weight of cyclohexane, and 1 part of 1-hexene was added as a molecular weight regulator. In this solution, as a polymerization catalyst, 10 parts by weight of a 15% solution of triethylaluminum in cyclohexane, 5 parts by weight of triethylamine,
and 10 parts by weight of a 20% cyclohexane solution of titanium tetrachloride were added to initiate ring-opening polymerization at 30°C.

30 minutes after the start of polymerization, when the conversion rate from monomer to polymer reached 85%, a 5% cyclohexane solution of tungsten hexachloride was added and stirred for an additional 30 minutes.
The conversion rate from monomer to polymer was 100%.

[0031] 0.9 parts by weight of isopropyl alcohol and 7 parts by weight of ion-exchanged water were added to the cyclohexane solution of this polymer.
Parts by weight were sequentially added and refluxed at 80°C for 1 hour. As a result, the polymerization catalyst is hydrolyzed into a polymer solution and a heterogeneous component, which is made of 800 mesh diatomaceous earth (Radiolite #
800 (manufactured by Showa Kagaku) was removed by pressure filtration as a filtration layer to obtain a colorless and transparent solution. Volatile components were removed using a partially vertical cylindrical concentrator (Hitachi Control, manufactured by Hitachi, Ltd.) to obtain a polymer.

10 parts by weight of this ring-opened polymer was dissolved in 90 parts by weight of cyclohexane, and the concentration of titanium atoms, which are transition metal catalyst residues, was measured by atomic absorption spectrometry.
The amount was 5 ppm relative to the ring-opening polymer hydrogenated product.

Example 1 A heterogeneous catalyst with a pore volume of 0.8 cm3/g and a specific surface area of 300 m2/g was prepared using activated alumina as a carrier, supporting 0.35 g of nickel and 0.2 g of nickel oxide per 1 g of the heterogeneous catalyst. The particles were sieved through a 150 mesh screen and the larger ones were selected to obtain a catalyst with a minimum particle size of 0.2 μm or more. A 20% cyclohexane solution of the polymer obtained in Reference Example 1 was placed in a pressure-resistant reaction vessel, 2% by weight of the above catalyst was added to the polymer, and a hydrogenation reaction was carried out at a hydrogen pressure of 45 kg/cm2 and a temperature of 230°C for 3 hours. After this, the reaction solution was filtered by layering 800 mesh diatomaceous earth (Radiolite #800) and 300 mesh diatomaceous earth (Radiolite #300, manufactured by Showa Kagaku), and filtered with a 0.5 μm cartridge filter. Further, the catalyst was removed by filtration using a 0.2 μm cartridge filter. Next, volatile components were removed using a vertical cylindrical concentrator to obtain a hydrogenated thermoplastic norbornene polymer. This hydrogenated thermoplastic norbornene polymer has a hydrogenation rate of approximately 10 by H1-NMR.
It was confirmed that it was 0%.

[0034] When 10 parts by weight of this ring-opening polymer hydrogenate was dissolved in 90 parts by weight of cyclohexane, the concentrations of titanium atoms and nickel atoms were measured by atomic absorption spectrometry. Both were below the detection limit of 1 ppm.

Example 2 Molecular sieves were used as a carrier to support 0.35 g of nickel and 0.2 g of nickel oxide per 1 g of heterogeneous catalyst, pore volume 0.8 cm3/g, specific surface area 300 m2/g.
The heterogeneous catalysts were sieved through a 150 mesh screen and the larger ones were selected to obtain catalysts with a minimum particle size of 0.2 μm or more. A 20% cyclohexane solution of the polymer obtained in Reference Example 1 was placed in an autoclave, and the above catalyst was added to the polymer at a ratio of 2
Added by weight%, hydrogen pressure 45 kg/cm2, temperature 230
After carrying out the hydrogenation reaction at ℃ for 3 hours, the reaction solution was filtered by layering 800 mesh diatomaceous earth (Radiolite #800) and 300 mesh diatomaceous earth (Radiolite #300), and then filtered into a 0.5 μm cartridge. The catalyst was removed by filtration using a filter and further filtration using a 0.2 μm cartridge filter. Next, volatile components were removed using a vertical cylindrical concentrator to obtain a hydrogenated thermoplastic norbornene polymer. This hydrogenated thermoplastic norbornene polymer has a hydrogenation rate of approximately 100 according to H1-NMR.
It was confirmed that %.

10 parts by weight of this hydrogenated ring-opening polymer were dissolved in 90 parts by weight of cyclohexane, and the concentrations of titanium atoms and nickel atoms were measured by atomic absorption spectrometry. Both were below the detection limit of 1 ppm.

Comparative Example 1 A nickel catalyst (N-113, manufactured by JGC Chemical Co., Ltd., nickel per 1 g) in which nickel was supported using diatomaceous earth as a carrier.
35g, supporting nickel oxide 0.2g, pore volume 0.2
~0.3cm3/g, specific surface area 100m2/g) 15
The particles were sieved through a 0-mesh screen and the larger ones were selected to obtain a catalyst with a minimum particle size of 0.2 μm or more. A 20% cyclohexane solution of the polymer obtained in Reference Example 1 was placed in a pressure-resistant reaction vessel, 5% by weight of the above nickel catalyst was added to the polymer, and 2% by weight of isopropyl alcohol was added to the solution to activate the catalyst. After carrying out a hydrogenation reaction at a hydrogen pressure of 45 kg/cm2 and a temperature of 190° C. for 3 hours, a portion was collected and a hydrogenation reaction was carried out for an additional 2 hours. Layering 800 mesh diatomaceous earth (Radiolite #800) and 300 mesh diatomaceous earth (Radiolite #300), filtering the reaction solution of 3-hour hydrogenation and 5-hour hydrogenation, and using a 0.5 μm cartridge filter. The catalyst was removed by filtration with a 0.2 μm cartridge filter, and volatile components were removed with a vertical cylindrical concentrator to obtain a thermoplastic norbornene polymer hydrogenated product. H1-
It was confirmed by NMR that the hydrogenation rates of the hydrogenated thermoplastic norbornene polymer hydrogenated for 3 hours and 5 hours were approximately 85% and approximately 100%, respectively.

When 10 parts by weight of this hydrogenated ring-opened polymer with a hydrogenation rate of approximately 100% was dissolved in 90 parts by weight of cyclohexane and subjected to atomic absorption spectrometry, it was found that the hydrogenated ring-opened polymer had a transition The concentration of titanium atoms, which are metal catalyst residues, was 2 ppm, and the concentration of nickel atoms was 400 ppm.

Example 3 Using an injection molding machine (manufactured by Sumitomo Heavy Industries, Model DISK5-3M), Example 1 was carried out at a mold temperature of 110°C and an injection temperature of 300°C.
The polymer hydrogenated product obtained in 1.2 mm thick and 130 m
It was molded into an optical disk substrate with a diameter of m. Metallic aluminum was vacuum-deposited on this substrate and subjected to a high temperature and high humidity test at 70° C. and 90% humidity for 24 hours, but no abnormality such as blistering was observed in the adhesion between the metal aluminum film and the substrate.

Comparative Example 2 An optical disk substrate was molded in the same manner as in Example 3, except that the polymer hydrogenate obtained in Comparative Example 1 was used instead of the polymer hydrogenate obtained in Example 1, and metal aluminum was molded. vapor deposited,
A high-temperature, high-humidity test was conducted, but blisters were observed between the metal aluminum film and the substrate, and there were problems with adhesion.

Example 4 Using an injection molding machine (manufactured by Sumitomo Heavy Industries, Model DISK5-3M), the hydrogenated polymer obtained in Example 1 was molded into a mold with a thickness of 3 mm at a mold temperature of 145°C and an injection temperature of 290°C. Projection T
A lens for V was molded and cooled to 90° C. 6 minutes after injection. When the light transmittance was measured using a spectrophotometer, 4
It was 90% or more in the entire region from 00 nm to 700 nm, and the minimum was 90.4%.

Comparative Example 3 A lens was molded in the same manner as in Example 4 except that the hydrogenated polymer obtained in Comparative Example 1 was used instead of the hydrogenated polymer obtained in Example 1. In this region, the light transmittance was 88% or less, and the maximum was 87.9%.

[0043]

Effect of the invention: The thermoplastic norbornene polymer hydrogenated product of the present invention has the same heat resistance, moisture resistance, etc. as conventional thermoplastic norbornene resins, but the content of transition metal atoms derived from the polymerization catalyst is 1 ppm or less. Therefore, the transparency is improved, and the light transmittance at 430 nm is 90% or more in a molded product with a thickness of 3 mm, and the molded product has good adhesion to a metal film or the like.

Claims (7)

[Claims] 1. A hydrogenated thermoplastic norbornene polymer containing 1 ppm or less of transition metal atom pigment derived from a polymerization catalyst. [Claim 2] A thermoplastic norbornene-based polymer containing polymerization catalyst residue is hydrogenated using a heterogeneous catalyst with a pore volume of 0.5 cm3/g or more in which a catalytic metal is supported on an adsorbent. A method for producing a thermoplastic norbornene polymer hydrogenate, which comprises removing a catalyst and recovering the thermoplastic norbornene polymer hydrogenate. 3. The method for producing a hydrogenated thermoplastic norbornene polymer according to claim 2, wherein the adsorbent is activated alumina or synthetic zeolite. 4. An optical element substrate formed by molding the hydrogenated thermoplastic norbornene polymer according to claim 1. 5. An information recording medium optical element comprising an information recording film laminated on the optical element substrate according to claim 4. 6. An optical element comprising an optical element pattern laminated on the optical element substrate according to claim 4. 7. A lens formed by molding the hydrogenated thermoplastic norbornene polymer according to claim 1.