JPH02274708A - Resin modifier and resin composition - Google Patents

Abstract

PURPOSE:To obtain a resin modifier useful for improving the heat resistance of a plastic by using a copolymer of a specified polymerizable component in a naphtha oil with maleic anhydride. CONSTITUTION:A polymerizable component in a naphtha oil based on 8 to 11C aromatic hydrocarbons which are hydrocarbon oils desirably comprising 70 to 99wt.% indene, 0.5 to 29.5wt.% styrene and 0.5 to 29.5wt.% at least one member selected from among (alpha-)methylstyrene, methylindene, dimethylstyrene, trimethylstyrene, coumaron and dicyclopentadiene is reacted with maleic anhydride in a solvent in the presence of a radical reaction initiator to obtain a resin modifier having a copolymer of a number-average MW of 1200 to 50000 as an effective component. This modifier is mixed with a thermoplastic resin to obtain a resin composition.

Description

Detailed Description of the Invention <Industrial Application Field> The present invention relates to the effective use of coal-based or petroleum-based naphtha oil, which is mainly composed of aromatic hydrocarbons having 8 to 11 carbon atoms. The present invention also relates to a resin modifier containing a copolymer of a polymeric component in naphtha oil and maleic anhydride as an active ingredient, and a resin composition or coating composition containing the same.

<Prior art> A copolymer of styrene and maleic anhydride has attracted attention as a heat-resistant resin, and is widely used in ABS resin, polycarbonate resin (
It is known that heat resistance can be improved by blending with PC resin), polyvinyl chloride resin (PVC resin), polystyrene resin, nylon, etc.
cPlast, Eng, 8nnu, Tech, conf
,,vol1.45. NO, 45pp1384-1387
(+987), J, Appl, Polym, Sci,
, vo132 NO, 8, p96131-6149 (
1986).

<Problem to be solved by the invention> However, since the thermal decomposition initiation temperature of the copolymer of styrene and maleic anhydride itself is approximately 200°C, it is difficult to process at temperatures exceeding 200°C for extrusion molding or injection molding. When heating the styrene-maleic anhydride copolymer, phenomena such as weight loss, coloring, and foaming due to gasification of low-boiling-point components due to the scission of the main chain and side chain of the styrene-maleic anhydride copolymer are observed. Although it has the performance as a resin modifier for improving heat resistance and a resin composition for improving heat resistance, there is a problem that it cannot be used in practice.

The present invention has better heat resistance than resin compositions containing styrene-maleic anhydride copolymers, and can be mixed with general-purpose plastics at around 250°C (-J) and used without problems when performing extrusion molding, injection molding, etc. The object of the present invention is to provide a resin modifier containing as an active ingredient a copolymer of indene or a polymerization component in naphtha oil and maleic anhydride, and a resin composition containing the same.

<Means to solve the problem> Coal-based or petroleum-based naphtha oil is mainly composed of aromatic hydrocarbons having 8 to 11 carbon atoms, and this naphtha oil contains indene as a main polymerization component. Contains components with reactive double bonds (polymerization components). Inden is
Since it has a bicyclic structure and is more rigid than styrene, resins containing indene are expected to have improved heat resistance. Therefore, the inventors investigated the production of a copolymer of naphtha oil and maleic anhydride, which contains indene as the main polymerization component, and found that
Makromol, Chem, 62,120 (19B
We discovered that it is possible to industrially produce copolymers of naphtha oil polymerization components and maleic anhydride of various molecular weights with higher yields than those reported in 3) and by combining reaction conditions. Moreover, these copolymers are effective as alkali hydrolysates, esterified products, sulfonated products, alkali hydrolyzed esterified products, and alkali hydrolyzed sulfonated products as various dispersants, paint compositions, and adhesives. I found that.

In addition, when a copolymer of the polymerization component in naphtha oil and maleic anhydride was tested using a thermobalance etc., it was found that the heat resistance was 30.
It was found that it does not thermally decompose up to temperatures close to 0°C, and that it is compatible with a wide range of general-purpose plastics such as vinyl chloride, ABS resin, and PC resin, and that it improves the heat resistance of these general-purpose plastics, leading to the present invention. Ta.

That is, in order to achieve the above object, according to the first aspect of the present invention, a polymeric component in naphtha oil containing aromatic hydrocarbons having 8 to 11 carbon atoms as a main component and maleic anhydride. A resin modifier containing a copolymer of the present invention as an active ingredient, and a resin composition containing the same are provided.

Further, according to the second aspect of the present invention, 5wt of polymerized component
% or more, and the polymerization component is indene 50% or more.
Provided are a resin modifier containing as an active ingredient a copolymer of a polymeric component in naphtha oil and maleic anhydride, which is composed of % by weight or more, and a resin composition containing the same.

Further, according to the third aspect of the present invention, the polymerization component is 5wt.
% or more, and the polymerization component is the following component (a
), (b) and (c) in weight percentages, and a resin modifier containing as an active ingredient a copolymer of a polymeric component in naphtha oil and maleic anhydride, and a resin composition formed by blending the same. things are provided.

(a) Indene 70-99 wt% (b) Styrene 0.5-29.5 wt% (c) Carried from the group consisting of α-methylstyrene, methylstyrene, methylindene, dimethylstyrene, trimethylstyrene, coumaron and dicyclopentadiene In addition, according to the fourth aspect of the present invention, a resin modifier containing a copolymer of indene and maleic anhydride as an active ingredient. A resin composition containing the same is provided.

The present invention will be explained in more detail below.

Naphtha oil is a neutral oil produced using coal and petroleum as raw materials.It has a boiling point range of 80℃ to 220℃, contains aromatic hydrocarbons with 8 to 11 carbon atoms as its main component, and has a boiling point of 80℃ to 220℃. The main ingredients are benzene, toluene, xylenes, trimethylbenzenes, ethyltoluenes, indanes, tetramethylbenzenes, methylindanes,
Components of naphtha oil that do not have reactive double bonds, such as propylbenzenes and naphthalenes, and components that have reactive double bonds, specifically styrene, α-methylstyrenes, and methylstyrene. It is composed of dimethylstyrenes, trimethylstyrenes, indenes, methylindenes, dicyclopentadiene, coumarons, etc. In addition, acidic substances, basic (nitrogen-containing) substances, and sulfur-containing substances are also present to some extent, but their contents vary greatly depending on the pretreatment method of naphtha oil.

The polymerization component in naphtha oil in the present invention refers to a mixture whose main components are indene present in naphtha oil and an aromatic hydrocarbon oil having reactive double bonds.

The composition of naphtha oil varies depending on the distillation method and raw materials, but on average, the total amount of indene, which is a polymerization component, and aromatic hydrocarbon oil with reactive double bonds is 5 to 8.
It is about 0wt%. If precision distillation is further performed, it is possible to increase the content of polymerization components to 100%, but this is not very desirable from operational or cost standpoints.

The higher the content of the polymerization component in naphtha oil, the raw material for the copolymer in the present invention, the easier the production of the copolymer. It has the advantage that there is no need for a step of isolating polymerized components, and that non-polymerized components can be used as a reaction solvent during the production of the copolymer of the present invention.

Indene has the largest content among the polymerization components, and for coal tar naphtha oil, indene accounts for 50 wt% or more of the polymerization components.

The copolymer used in the present invention is a copolymer obtained from such coltal naphtha oil.

The polymerization component in naphtha oil in the present invention is mainly composed of aromatic hydrocarbon oil having reactive double bonds, and the composition is as follows: the main component is indene, and the polymerization component of naphtha oil is It contains 5wL% or more, and its polymerization components are composed of the following components (a), (b), and (c) in weight percentages, and (a), (b), and (c) are specifically shown. (a) Indene 70-99 wt% (b) Styrene 05-29.5 wt% (c) α-methylstyrene, methylstyrene, methylindene, dimethylstyrene, trimedylstyrene, coumaron 13 and dicyclopentadiene The sum of (a), (b) and (c) is 05 to 29.5 wt% depending on one or two sides of the back side.
(a)+(b)4-(c)-100wt%.

The copolymer used in the present invention is a copolymer of maleic anhydride and a naphtha oil polymerization component whose main component is an aromatic hydrocarbon having a reactive polybond as described in (3) above.

This copolymer is produced by subjecting a polymeric component in naphtha oil to a radical polymerization reaction with maleic anhydride. The composition of the copolymer may vary depending on the components of the aromatic hydrocarbon oil having reactive double bonds in the naphtha oil used, or an aromatic hydrocarbon oil within the composition range of (a) to (c) below, for example. It is a copolymer of hydrocarbon oil and maleic anhydride.

(a) Indene 70-99wt% (b) Styrene 0.5-29.5wt% (c) Consists of α-methylstyrene, methylstyrene, methylindene, dimethylstyrene, 1-dimethylstyrene, coumaron, and dicyclopentadiene at least one selected from the group,
or two or more golden words" 05 to 29.5 wt% The copolymer of the polymeric component and maleic anhydride in the naphtha oil obtained has a number average molecular i (Mn) of 1,200 to 50
,000 white powder, which can be widely used as a resin modifier, fluidizing agent, dye and pigment dispersant, adhesive, paper sizing agent, etc. It is particularly useful as a modifier for thermoplastic resins, which will be described in detail later.

In general, considering that styrene is industrially produced by the dehydrogenation reaction of ethylhenzene, the copolymer of styrene and maleic anhydride is also expensive, as it is an expensive raw material. The copolymer of the polymeric component and maleic anhydride is an industrially attractive product.

The above-mentioned copolymer is obtained by subjecting maleic anhydride to a radical polymerization reaction with a naphtha oil polymerization component whose main component is an aromatic hydrocarbon having a reactive double bond.

Is it possible to concentrate only the polymerized components from naphtha oil and copolymerize them with maleic anhydride? Or, if naphtha oil is used as is, the step of concentrating the polymerized components in naphtha oil can be omitted. This is preferable because hydrocarbon compounds other than the polymerization components therein can be used as a solvent during the radical polymerization reaction.

The copolymer is produced by a radical reaction between the polymerization component in naphtha oil and maleic anhydride at a temperature range of 0°C to 180°C. It is possible to produce it by using a copolymerization reaction.

However, if the entire amount of naphtha oil containing 5 wt% or more of polymerization components and maleic anhydride is charged into the polymerization reactor from the beginning, and a radical reaction is initiated by a radical reaction initiator or thermal radicals caused by the reaction temperature, Since temperature control is considerably difficult due to the heat of reaction, this is not an industrially suitable method. Therefore, it is preferable to add either or both of naphtha oil and maleic anhydride into the polymerization reactor at a rate that can control the reaction temperature to an appropriate temperature.

In radical polymerization reactions, it is essential to generate radicals by an appropriate method. In this case, there is a method of inducing thermal radicals by adding a radical reaction initiator or raising the reaction temperature, but in the case of the polymerization component in naphtha oil and maleic anhydride copolymer, thermal radicals The temperature at which this occurs must be as high as 130° C. or higher, and the resulting copolymer will be colored, which is not preferable. Therefore, in this method, it is better to use a method that utilizes a radical reaction initiator.

The radical reaction initiator used may be either an azo radical reaction initiator or a peroxide radical initiator, but the temperature range in which radicals work effectively is 50°C.
-130°C, and more specifically, a radical reaction initiator having a half-life at the reaction temperature of 0.1 to 10 hours is preferably selected. Preferably, as a polymerization initiator, azobisisobutyronitrile, benzoyl peroxide, dicumyl peroxide, Perbutyl I (manufactured by Shiraki Yushi ■), Barbdel Z (manufactured by NOF ■), etc. are used.

As for the method of adding the radical reaction initiator, it is not appropriate to charge the entire amount into the polymerization vessel because decomposition will start at the same time. Therefore, it is best to gradually charge the radical reaction initiator into the polymerization kettle.Depending on the type of radical reaction initiator, some are solid, so it is preferable to dissolve it in naphtha oil or maleic anhydride solution and add it to the polymerization kettle.

The amount of radical reaction initiator used is 0.0 based on the total number of moles of polymerization component and maleic anhydride in naphtha oil.
It may be from 5 mol% to 5 mol%. Note that maleic anhydride is solid at room temperature, so if it is added gradually, it must be dissolved in a solvent inert to the reaction or in naphtha oil.

The properties of the solvent that can be used in this reaction are such that it does not cause any chemical reaction with maleic anhydride, dissolves maleic anhydride, is compatible with naphtha oil, and does not alter the quality of the copolymer produced. No. Such solvents include solvent components other than the polymerization components contained in naphtha oil, such as benzene, toluene, xylenes, trimedylhenzenes, tetramethylbenzenes, indane, methylindane, ethylbenzene, propylbenzene, etc. Other than aromatic hydrocarbons or naphtha oil components, ketones such as acetone, methyl ethyl ketone, methyl propyl ketone, methyl isobutyl ketone, and cyclohexanone, alkyl halides such as 1,2-dichloroethane,
Examples include ethers such as ethyl ether, dioxane, anisole, and tetrahydrofuran.

The reaction vessel (polymerization pot, etc.) to be used may be made of a material that does not inhibit radical reactions, such as glass or stainless steel.
For example, if mild steel is used as the material for the polymerization pot, if the surface becomes somewhat corroded due to air oxidation, radical decomposition will be promoted in that area, and the reaction will often proceed rapidly, so control the reaction temperature. It is difficult and dangerous. In particular, when a peroxide-based initiator is used as an initiator, special care must be taken because an abnormal decomposition reaction rapidly proceeds at the corrosion site of mild steel.

The method for producing the copolymer will be described in more detail in Examples, but the outline will be as follows. Maleic anhydride dissolved in a solvent is charged into a glass polymerization kettle equipped with a stirrer, an external heater for heating, and a cooler, or a polymerization kettle with a glass-coated reaction solution contact part, or a stainless steel polymerization kettle, and maintained at reflux temperature. By this,
Dissolved oxygen in the solution can also be degassed. Since oxygen captures radicals, it must be removed by nitrogen substitution in general radical reactions.

IQ (Removal of dissolved oxygen from the reaction system is a necessary operation in the case of producing a copolymer of the polymerization component in naphtha oil and maleic anhydride, even if the reaction format is changed.

Then, naphtha oil is gradually added through the charging port at the top of the polymerization reactor using an appropriate method such as pump charging or dripping.

At this time, the naphtha oil may be diluted with the above-mentioned inert solvent. Further, the radical reaction initiator may be added by dissolving it in the naphtha oil to be added from the beginning and adding it together with the naphtha oil, or by gradually adding the radical reaction initiator separately from a separate charging port. It is necessary that the radical reaction initiator is a solid, dissolved in the above-mentioned solvent, and then added.

Regarding the reaction method, naphtha oil or naphtha oil diluted with a suitable solvent is charged in a polymerization reactor, and the maleic anhydride solution is pumped together with the radical reaction initiator or separately from the radical reaction initiator. It may be added to the polymerization vessel by an appropriate method such as dropwise addition.Furthermore, at the start of the reaction, only the solvent is charged, the temperature is brought to reflux, and the naphtha oil, maleic anhydride, and radical reaction initiator are added together or in an appropriate manner. They may be divided into different combinations and added to the polymerization tank by an appropriate method such as pumping or dropping. However, when maleic anhydride is added to the polymerization reactor, since maleic anhydride is a solid, it is necessary to dissolve it in an appropriate amount of the above-mentioned solvent and then add it.

Furthermore, even when maleic anhydride is dissolved in naphtha oil and added, it is difficult to dissolve in naphtha oil alone, so it is better to dilute it with an appropriate amount of solvent.

A polymerization reaction is performed using any of the above methods to produce a copolymer of the polymerization component in naphtha oil and maleic anhydride.

When adding the reaction raw materials, due to the heat of reaction, the ratio changes to that before the start of addition.
It can be observed that the solution in the polymerization vessel is violently refluxed in the cooling tube. As the addition rate increases, the intensity of the reflux increases.

Therefore, it is necessary to control the reaction so as not to cause bumping, and the addition rate requires 0.5 to 5 hours.

After the addition, it is necessary to maintain the temperature at the same temperature as at the time of addition until the reaction is completed, but generally, 0.5 to 2 times the addition time is sufficient and the reaction is almost complete.

The yield is determined by the following formula (1).

Copolymer yield (wt%) of the polymerized component in naphtha oil and maleic anhydride...Formula (1) The obtained copolymer was analyzed using infrared absorption spectroscopy (IR).
The analysis was carried out by method, nuclear magnetic resonance (NMR) method and Kerbermeation chromatography (GPC) method.

The above describes the method for producing the copolymer according to the third aspect of the present invention, or the method for producing the copolymer according to the first, second, and fourth aspects of the present invention can also be obtained in the same manner. Kategiru.

Furthermore, the method for producing the copolymer is not limited to the above method.

Further, the indene in the fourth aspect of the present invention is not limited to that obtained from naphtha oil.

When the thermal properties of the copolymer obtained using this indene or naphtha oil and maleic anhydride as raw materials were measured, it was found that 30
There is no weight loss up to a temperature around 0°C, and there is no change in the weight or molecular weight of the copolymer even if it is held for a long time under a nitrogen gas atmosphere at around 250°C, which is the general kneading temperature for general-purpose plastics. There was no change.

This is because indene, or indene, which is the main polymeric component in naphtha oil, has a bicyclic structure and is more thermally stable than the conventionally used styrene.

In the past, when the content of indene among the polymeric components in naphtha oil increased, the heat resistance of the copolymer of the polymeric component in naphtha oil and maleic anhydride improved, and indene was 50wt among the polymeric components in naphtha oil. Even if a copolymer with maleic anhydride is produced using ordinary naphtha oil containing 50% or more as a raw material, the thermal stability is improved compared to a styrene-maleic anhydride copolymer, and it is difficult to mix with general-purpose Plus Deck. Even if it is molded using an appropriate method, there will be no problem, and the heat resistance of general-purpose plastics will be improved.

The copolymer can be prepared from ABS resin, PC resin, p
VC resin, polystyrene resin, nylon, and other thermoplastic resins alone or in a mixture are blended in the desired proportions, mixed at around 250°C using a suitable means such as a single-screw or twin-screw kneader, and processed by conventional methods such as extrusion molding and injection molding. A heat-resistant resin composition or coating composition can be obtained by the following method.

The resin composition of the present invention may also contain various fillers, if necessary.
Admixtures, anti-aging agents, etc. can be added.

<Examples> The present invention will be specifically described below based on Examples, but the present invention is not limited thereto.

(Example 1) Glass polymerization pot (stirrer I) with an internal volume of 500 mj2,
(=J, water order)
Dissolve 24.5 g (0.25 mol) of maleic acid in 100 mfL of methyl ethyl ketone and charge it into a container.

While stirring with a stirrer, the temperature is maintained at reflux with an external heater. Thereafter, 60 g of naphtha oil (polymerization component contains 48 wt% (0.25 mol) in terms of indene (molecular weight 116)) and azoisobutyronitrile (AI) as a radical polymerization initiator are added to the dropping funnel suspended above the polymerization pot.
A solution containing 410 mg of BN) was added, and this solution was slowly added dropwise over 1 hour. After the dropwise addition was completed, the reaction solution was left under reflux for 2 hours to complete the reaction. This reaction solution was then returned to room temperature and used as a precipitation tank with an internal volume of 1
300 mJ2 of normal hexane was placed in a beaker of ρ, and it was gradually added thereto to precipitate a white copolymer. Next, it is separated by suction filtration, dried under reduced pressure,
A copolymer of the polymerization component in naphtha oil and maleic anhydride was obtained in a yield of 95 wt%. The yield was determined from the above formula (1).

Prior to the synthesis experiment, the composition of the naphtha oil was determined by gas chromatography (GC) analysis, and the composition was as follows.

Composition of naphtha oil Composition of polymerization components The obtained copolymer had a number average molecular weight of 13.500.

(Example 2) 27 g of indene was placed in a glass polymerization pot with an internal volume of 500 mfl (with a stirrer, 2 dropping funnels with wood, and a water-cooled cooling pipe).
(0.25 mol) was diluted with 100 mu of methyl isobutyl ketone and kept at reflux temperature with an external heater while stirring with a stirrer.

Then, one of the two wooden dropping funnels was charged with a solution of 24.5 g of maleic anhydride dissolved in 100 mjZ of methyl isobutyl ketone. On the other tree, as a radical reaction initiator, 50 mg of Verbutyl Z (a product of NOF ■), which is a peroxide-based radical reaction initiator, was added to the other tree.
mft of methyl isobutyl ketone and charged.

Thereafter, the solutions charged in the two wooden dropping funnels were simultaneously started dropping, and both were slowly dropped over a period of 1 hour. After the dropwise addition was completed, the reflux temperature was maintained for 1 hour to complete the reaction.

The reaction solution was returned to room temperature, and 300 mJ2 of glue groin was filled in a glass beaker with an internal volume of I°C as a precipitation tank, and was gradually added thereto to precipitate white indene and maleic anhydride copolymer. . This precipitate was separated by suction filtration and dried under reduced pressure to obtain an indene and maleic anhydride copolymer with a yield of 96 wt%.

The obtained copolymer had a number average molecular weight of 12,000.

(Example 3) Prior to the experiment, the composition of naphtha oil was determined by gas chromatography (GC) analysis, and the composition was as follows.

Composition of naphtha oil Composition of polymerization components: Toluene was charged at 300 m°C into a glass polymerization kettle (stirrer, dropping funnel (JL), with a volume of 1°C), and while stirring with a stirrer, In an oil bath with a temperature controller, the temperature was maintained at which the solvent in the polymerization kettle refluxed.Into a dropping funnel, 464 g of naphtha oil, 98 g of maleic anhydride, 1 to 16 g of azoisobutyroni, and 16 g of toluene+00+nJ2 were charged as a homogeneous solution, and about 1 This solution was slowly added dropwise over time, or about 8 minutes after the start of dropping, the reaction solution became cloudy.

Thereafter, the reaction temperature was maintained for 2 hours to complete the reaction.

After the reaction was completed, the temperature was returned to room temperature, and fine particles produced were separated by suction filtration, followed by drying under reduced pressure to obtain a copolymer of the polymerization component in naphtha oil and maleic anhydride at a yield of 93 wt%.

The number average molecular weight of the obtained copolymer was determined to be 7.0 by GPC method.
It was 200.

(Example 4) The weight loss of the copolymer obtained in Example 1 was measured by Rigak under nitrogen atmosphere at 3°C/m1n (room temperature to y, temperature).
When measured using a thermobalance manufactured by U Co., Ltd., it was 310
Weight loss was observed from ℃.

(Comparative Example 1) The weight reduction of the copolymer of styrene and maleic anhydride was
When measured under the same conditions as in Example 4, weight loss was observed from 280°C.

(Example 5) The copolymer obtained in Example 3 was heated to 270% under nitrogen atmosphere.
Rigaku (2'A:
When the weight loss was measured using a thermobalance manufactured by ),
No weight loss was observed. Furthermore, when the molecular weight of the copolymer used in the measurement was measured by GPC,
Since there is no change in the molecular weight, it is considered that cleavage of the main chain and side chains of the copolymer does not proceed at a temperature of 270°C.

(Comparative Example 2) When a copolymer of styrene and maleic anhydride (commercially available) was measured for weight loss under the same conditions as in Example 5, a weight loss of 5% of the total weight was observed at the end of the measurement. It was done. From this, it can be said that a copolymer of styrene and maleic anhydride has poorer thermal stability than a copolymer of a naphtha oil polymerization component and maleic anhydride.

<Effects of the Invention> Since the present invention is configured as described above, a resin modifier containing indene or a copolymer of J, 1 synthetic component in naphtha oil and maleic anhydride as an active ingredient; It has excellent heat resistance and is useful as a resin composition or coating composition containing it.

Claims (8)

[Claims] (1) Resin modification characterized in that the active ingredient is a copolymer of a polymeric component in naphtha oil containing an aromatic hydrocarbon having 8 to 11 carbon atoms as a main component and maleic anhydride. agent. (2) A copolymer of maleic anhydride and a polymeric component in naphtha oil containing 5 wt% or more of a polymeric component, and the polymeric component is composed of 50 wt% or more of indene as an active ingredient. Characteristic resin modifier. (3) Polymerized components and maleic anhydride in naphtha oil containing 5 wt% or more of polymerized components and composed of the following components (a), (b), and (c) in weight percentages: A resin modifier characterized by containing a copolymer with as an active ingredient. (a) Indene 70-99 wt% (b) Styrene 0.5-29.5 wt% (c) Selected from the group consisting of α-methylstyrene, methylstyrene, methylindene, dimethylstyrene, trimethylstyrene, coumaron, and dicyclopentadiene total of at least one or two or more of 0.5 to 29.
5wt%. (4) A resin modifier characterized by containing a copolymer of indene and maleic anhydride as an active ingredient. (5) A resin composition prepared by blending a copolymer of a polymeric component in naphtha oil containing an aromatic hydrocarbon having 8 to 11 carbon atoms as a main component, maleic anhydride, and a thermoplastic resin. (6) A copolymer of a polymeric component in naphtha oil containing 5 wt% or more of a polymeric component, and the polymeric component is composed of 50 wt% or more of indene, maleic anhydride, and a thermoplastic resin. A resin composition. (7) Polymerized components and maleic anhydride in naphtha oil containing 5 wt% or more of polymerized components and composed of the following components (a), (b), and (c) in weight percentages: A resin composition formed by blending a copolymer with and a thermoplastic resin. (a) Indene 70-99 wt% (b) Styrene 0.5-29.5 wt% (c) Selected from the group consisting of α-methylstyrene, methylstyrene, methylindene, dimethylstyrene, trimethylstyrene, coumaron, and dicyclopentadiene total of at least one or two or more of 0.5 to 29.
5wt% (8) A resin composition comprising a copolymer of indene and maleic anhydride and a thermoplastic resin.