JPH09227625A - Brominated polystyrene for flame retardant and flame retardant resin composition comprising the same - Google Patents

Abstract

(57) Abstract: [PROBLEMS] To provide a brominated polystyrene for a flame retardant and a flame-retardant resin composition comprising the same, which can significantly improve processability without deteriorating mechanical properties. A brominated polystyrene for a flame retardant having a weight average molecular weight in terms of polystyrene of 5,000 to 15,000 is produced and used.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a brominated polystyrene for a flame retardant and a composition comprising the same. The brominated polystyrene for a flame retardant and a composition comprising the same reduce mechanical properties. It is a compound useful for flame-retarding synthetic resins, and can also be used as a compounded flame-retardant for flame-retardant resins, which is often used in various electric products.

[0002]

2. Description of the Related Art As conventional flame retardants for synthetic resins, various brominated flame retardants, phosphoric acid ester flame retardants, inorganic flame retardants, etc. are used for various resins. Has been done. Typical flame retardants include decabromodiphenyl oxide, tetrabrobisphenol-A (hereinafter abbreviated as TBA), TBA-epoxy oligomer, magnesium hydroxide, aluminum hydroxide and the like. Further, the brominated polystyrene and the method for producing the same are described in, for example, JP-A-56-127876, but there is a problem that mechanical properties, processability, etc. are deteriorated depending on the type of resin to be blended.

As described above, although various flame retardants have been proposed and used for various purposes, there is a strong demand for recent regulations on flame retardancy and further improvement in the performance of blended flame retardant resins. It is desired to create an agent that complements the drawbacks of conventional products.

[0004]

DISCLOSURE OF THE INVENTION An object of the present invention is to provide a brominated polystyrene for a flame retardant, which has not been obtained by a conventional flame retardant, and which has mechanical properties maintained and greatly improved processability, and a composition comprising the same. Is provided.

[0005]

The present inventors have completed the present invention as a result of extensive studies based on such a background. That is, the present invention relates to a brominated polystyrene for a flame retardant having a weight average molecular weight in terms of polystyrene of 5,000 to 15,000 and a flame retardant resin composition comprising the same.

Hereinafter, the present invention will be described in detail.

The brominated polystyrene for flame retardant of the present invention is
Polystyrene-reduced weight average molecular weight of 5,000 to 15,
If it is 000, it is not particularly limited, but further,
For example, the bromine content is 40 to 70% by weight and the softening point is 150.
~ 250 ℃, 5% weight loss by thermobalance is 300 ℃
It is preferably a white to pale yellow powder exhibiting the above heat resistance.

If the weight average molecular weight of the obtained brominated polystyrene for flame retardant is less than 5,000 in terms of polystyrene, the heat distortion temperature of the composition may be significantly lowered and the required physical properties may not be satisfied. On the other hand, when it exceeds 15,000, the composition has poor moldability and impact resistance.

The production of the brominated polystyrene for the flame retardant of the present invention is not particularly limited. For example, the raw material polystyrene is dissolved in a solvent inert to the reaction in the presence of a catalyst, and the brominated reagent is added dropwise thereto. It is usually carried out depending on the method.

The polystyrene used in the present invention may have a weight average molecular weight of 5,000 to 15,000, and is usually
As long as it can be obtained by a polymerization reaction of a styrene monomer in the presence of a chain transfer agent, any one can be applied, and the type of the chain transfer agent is a halogen type such as carbon tetrachloride, a thiol type such as butyl mercaptan, and α-methyl. There are styrene dimers and the like, but they are not particularly specified. Examples of the polymerization method of polystyrene include radical polymerization, anionic polymerization, cationic polymerization, and the like, and the reaction form is, for example, all polystyrene obtained by solution polymerization, emulsion polymerization, suspension polymerization, etc. Is applicable as.

Examples of the catalyst applicable to the production of the brominated polystyrene for the flame retardant of the present invention include aluminum chloride, aluminum bromide, ferric chloride, ferric bromide, titanium tetrachloride, titanium trichloride, Examples thereof include antimony pentachloride, antimony trichloride, antimony tribromide, tin chloride, trifluoroborane etherate, etc. These catalysts are selected according to the desired nuclear bromination number. Further, these catalysts may be used alone or in combination of two or more kinds without causing any problems.

The catalyst can be added in any amount with respect to the styrene unit unit constituting the polystyrene used in the reaction. In consideration of reactivity, economy, etc., 0.01 mol / mol% The range of ˜100 mol / mol% is preferred. More preferably, 0.1 mol / mol%
˜30 mol / mol%.

The bromination reagent applicable to the present invention is not particularly limited and includes, for example, bromine, bromine chloride, etc., and the desired nuclear bromination number, the catalyst to be used and the bromine for the obtained flame retardant. Used or mixed depending on the target quality of the styrene compound.

The term "bromination reagent" as used herein is a generic term for reagents that substitute hydrogen atoms or other substituents of general organic compounds with bromine atoms and reagents that add bromine atoms to unsaturated bonds such as olefins. . Further, the nuclear bromination number refers to the number of bromine atoms bonded on the aromatic ring of the styrene unit forming polystyrene.

The amount of the brominated reagent added is varied depending on the nuclear bromination number of the target unit unit of brominated styrene. Usually, equimolar amount to target nuclear bromination number ~
A 5-fold molar amount is used, but preferably an equimolar amount to 1.
The amount is 5 times the molar amount, and the amount of the bromination reagent used is determined depending on the type of catalyst used and reaction conditions.

As the solvent used in the reaction, any solvent can be applied as long as it is inert to the bromination reagent and the catalyst, and examples thereof include dichloromethane, dibromomethane, chloroform, bromoform and carbon tetrachloride. To be

The solvent can be used in any amount ratio to 100 parts by weight of polystyrene used in the reaction, but is preferably 120 in view of the viscosity of the reaction solution and economical efficiency.
It is in the range of parts by weight to 8000 parts by weight.

The reaction temperature varies depending on the bromination reagent, the catalyst and the desired degree of nuclear bromination. Usually, when bromine is used, it is, for example, 0 ° C. to 60 ° C., bromine chloride or a combination system of bromine and bromine chloride. For example, it is carried out at -30 ° C to 20 ° C.

Since the reaction is exothermic and hydrogen chloride gas is generated, the reaction time can be controlled and the generated hydrogen chloride gas can be captured outside the system. There is no particular limitation. After adding the bromination reagent,
Post-treatment may be carried out immediately, or aging may be carried out at a predetermined temperature for 1 to 8 hours.

After the reaction is completed, excess bromination reagent is added, for example,
Hydrazine, sodium bisulfite and other reducing agents to remove harm, then, for example, washed with water, added to a poor solvent such as methanol to crystallize, further filtered, dried brominated polystyrene of the target by Obtained as a white to pale yellow powder.

The composition comprising the brominated polystyrene for a flame retardant of the present invention may be obtained by adding a synthetic resin such as a thermosetting resin, a thermoplastic resin or a flame retardant auxiliary to the brominated polystyrene for a flame retardant. Further, if necessary, additives such as an ultraviolet absorber, a light stabilizer, an antioxidant, an antistatic agent and an inorganic filler may be added.

Examples of the synthetic resin which can be blended with the brominated polystyrene for flame retardant of the present invention include thermosetting resins such as phenol resin, urea resin, melamine resin, unsaturated polyester, alkyd resin and epoxy resin,
Low density polyethylene, high density polyethylene, ethylene-
Vinyl acetate copolymer, polystyrene, high impact polystyrene, expanded polystyrene, acrylonitrile-styrene copolymer, acrylonitrile-butadiene-styrene copolymer (abbreviated as ABS hereinafter), polypropylene,
Examples thereof include petroleum resins, polymethylmethacrylate, polyamide, polycarbonate, polyacetal, polyethylene terephthalate, polybutylene terephthalate, and thermoplastic resins such as polyphenylene ether. The synthetic resin that brings out the features of the brominated polystyrene for the flame retardant of the present invention, polystyrene, impact-resistant polystyrene,
Expanded polystyrene, acrylonitrile-styrene copolymer, acrylonitrile-styrene-butadiene copolymer, polypropylene, petroleum resin, polymethylmethacrylate, polyamide, polycarbonate, polyacetal, polyethylene terephthalate, polybutylene terephthalate, polyphenylene ether, and the like. Polymer alloys typified by polycarbonate-ABS, polyphenylene ether-polystyrene, and the like, in which two or more types of thermoplastic resins are mixed, can be cited.

The amount of the brominated polystyrene for flame retardant of the present invention to be added to the synthetic resin varies depending on the type of resin to be added and the desired flame retardant performance, but is usually 5 parts by weight per 100 parts by weight of the resin. Add ~ 50 parts by weight.

In blending the brominated polystyrene for flame retardant of the present invention with a synthetic resin, a flame retardant aid such as antimony trioxide or sodium antimonate may be added.
10 to 80 parts by weight are used with respect to 100 parts by weight of brominated polystyrene for flame retardant. Further, if necessary, a benzotriazole-based ultraviolet absorber, a light stabilizer of a 2,2,6,6-tetramethylpiperidine derivative, a hindered phenol-based antioxidant, etc. are each contained in an amount of 0.05% by weight to
You may add 5 weight%. In addition, an antistatic agent, talc, an inorganic filler such as glass fiber may be added, if necessary.

Further, in order to obtain a flame-retardant resin composition having flame retardancy and non-drip property (property that droplets are not generated during combustion), it is usually 100 weight of the synthetic resin although it depends on the kind of the synthetic resin. 5 parts to 5 parts by weight of brominated polystyrene for flame retardant and 5 parts of glass fiber
˜200 parts by weight, 0.1-10 parts by weight of emulsion-polymerized Teflon as a drip suppressing agent, and 1 to 140 parts by weight of antimony trioxide or sodium antimonate as a flame retardant aid. The glass fiber and the emulsion-polymerized Teflon may be used in different types and amounts depending on the physical properties of the desired composition and the degree of drip suppression, and the processability is improved by using brominated polystyrene for flame retardants.

As a method for compounding the brominated polystyrene for flame retardant of the present invention with a synthetic resin, when compounded with a thermosetting resin, it may be dispersed in a resin raw material in advance and then cured. In the case of blending, for example, a conical blender, a tumbler mixer or the like may be used to mix the necessary blending reagents, and the mixture may be made into a pellet using a twin-screw extruder or the like, or after melt-mixing with a Banbury mixer, a pressure kneader, or the like. It may be pelletized using a shaft extruder or the like. The method for processing the obtained brominated polystyrene composition for flame retardant is not particularly limited, and the desired molded article can be obtained by, for example, extrusion molding, injection molding or the like.

[0027]

EXAMPLES The present invention will be described below in more detail with reference to examples, but the present invention is not limited to these examples.

Production Example 1 Production Example of Brominated Polystyrene with a Nuclear Bromide Number of 3 for Flame Retardants 5 equipped with a stirrer and a dropping funnel with a cooling jacket
In a three-necked round-bottomed flask having a volume of 1 liter, 100 g of polystyrene having a weight average molecular weight of 1.05 × 10 ^{4 in} terms of polystyrene, 21.9 g of antimony trichloride and 1000 of dichloromethane.
g, and cooled to 0 ° C. on an ice bath.

Then, at 5 ° C., 246 g of bromine and 109 of chlorine
g and bromine chloride prepared from 900 g of dichloromethane 3
A dichloromethane solution containing 55 g was charged into a cooling jacket, cooled at 0 ° C., added dropwise over 6 hours, and further aged at the same temperature for 3 hours.

To the resulting reaction solution was added 150 g of a 5% hydrazine aqueous solution, the bromine chloride was removed, the mixture was washed 3 times with 500 ml of water, separated, and then added to 5 l of stirred isopropanol to crystallize. Sedimentation, filtration, 1 mmH
By drying under reduced pressure of 120 ° C. for 4 hours, 255 g of a target brominated polystyrene for flame retardant was obtained.

The results of elemental analysis, softening point, gel permeation chromatography (GPC) and thermobalance measurement of the obtained brominated polystyrene for flame retardant are shown below.

Elemental analysis result: C H Br Cl measurement value (% by weight) 31.4 1.8 67.5 0.6 Softening point (° C.): 200 to 203 Gel permeation chromatograph (GPC): Weight average molecular weight (Mw) = 1.12 × 10 ⁴ , number average molecular weight (Mn) = 6.18 × 10 ³ , weight average molecular weight (Mw) / number average molecular weight (Mn) = 1.
81 Thermobalance (temperature increase rate: 10 ° C / min): 5% weight loss (337 ° C), 10% weight loss (353 ° C), 50% weight loss (390 ° C), 90% weight loss (502 ° C) Production Example 2 Nuclear bromine Production Example of Brominated Polystyrene for Flame Retardant with Chemical Number 3 5 equipped with stirrer and dropping funnel with cooling jacket
In a 3-necked round-bottomed flask having a volume of 1 liter, 100 g of polystyrene having a weight-average molecular weight of 2.94 × 10 ^{4 in} terms of polystyrene, 21.9 g of antimony trichloride and 1200 ml of dichloromethane.
g, and cooled to 0 ° C. on an ice bath.

Then, at 5 ° C., 246 g of bromine and 115 of chlorine
g and bromine chloride prepared from 900 g of dichloromethane 3
A dichloromethane solution containing 75 g was charged in a cooling jacket, cooled at 0 ° C., added dropwise over 6 hours, and further aged at the same temperature for 3 hours.

158 g of a 5% hydrazine aqueous solution was added to the obtained reaction solution, the bromine chloride was removed, the mixture was washed 3 times with 500 ml of water, separated, and then added to 5 l of stirred isopropanol to crystallize. Sedimentation, filtration, 1 mmH
257 g of the target brominated polystyrene for flame retardant was obtained by drying under reduced pressure at 120 ° C. for 4 hours.

The results of elemental analysis, softening point, gel permeation chromatography (GPC) and thermobalance of the obtained brominated polystyrene for flame retardant are shown below.

Elemental analysis result: C H Br Cl measurement value (% by weight) 30.0 1.8 67.6 0.8 Softening point (° C.): 220 to 225 Gel permeation chromatograph (GPC): Weight average molecular weight (Mw) = 3.02 × 10 ⁴ , number average molecular weight (Mn) = 1.45 × 10 ⁴ , weight average molecular weight (Mw) / number average molecular weight (Mn) = 2.
08 Thermobalance (temperature increase rate: 10 ° C / min): 5% weight loss (339 ° C), 10% weight loss (350 ° C), 50% weight loss (387 ° C), 90% weight loss (505 ° C) Flame retardant obtained The brominated polystyrene for use was subjected to a flammability test, workability (fluidity), impact resistance, a tensile test, a bending test, and the like by the methods described below.

<Evaluation method of flammability test> A test piece was prepared from a sample obtained by injection molding, and the oxygen index was JIS-K.
In accordance with -7201, the UL combustion test was performed according to the UV94V vertical flammability test method.

<Evaluation Method of Workability (Flowability)> Using the obtained pellets, the melt flow rate (275 ° C. × 325 g) was measured according to JIS-K-6760.

<Impact resistance> A test piece was prepared from a sample obtained by injection molding and conformed to ASTM-D-256.
The Izod impact value was measured.

<Tensile Test> A sample obtained by injection molding was punched out with a No. 3 dumbbell to obtain a tensile rate of 20.
It was measured at 0 mm / min.

<Bending Test> A test piece was prepared from the sample obtained by injection molding and measured according to JIS-K-7203.

Example 1 As shown in Table 1, the brominated polystyrene for flame retardant obtained in Production Example 1 was mixed with 6,6-nylon (Amylan CM manufactured by Toray).
3001) 30 parts by weight and 10 parts by weight of antimony trioxide were mixed with 100 parts by weight, and a twin-screw extruder (L / D: 2) was used.
5) was kneaded at 270 to 280 ° C to prepare pellets. Using these pellets, a melting temperature of 280 to 285 ° C,
Injection molding was performed at a mold temperature of 80 ° C. From these samples,
Test pieces for workability (fluidity), impact resistance, tensile test, bending test and flammability test were prepared, measured and evaluated. The results are shown in Table 1.

Workability (flowability), impact resistance, tensile test,
Both the bending test and the flammability test were satisfactory.

Table 1 also shows various evaluation results of 6,6-nylon (Amilan CM3001 manufactured by Toray) alone.

[0045]

[Table 1]

Example 2 As shown in Table 1, the brominated polystyrene for flame retardant obtained in Production Example 1 (having a weight average molecular weight of 1.
12 × 10 ⁴ ) 15 parts by weight and 5 parts by weight of antimony trioxide were added, and the same procedure as in Example 1 was performed to prepare test pieces for workability (fluidity), impact resistance, tensile test and bending test. Then, it was measured and evaluated.

The results are shown in Table 1.

The workability (flowability), impact resistance, tensile test and bending test were all satisfactory.

Comparative Example 1 As shown in Table 1, 30 parts by weight of commercially available brominated polystyrene having a weight average molecular weight of 200,000 in terms of polystyrene equivalent to 100 parts by weight of 6,6-nylon (Amylan CM3001 manufactured by Toray), The same procedure as in Example 1 was carried out except that 10 parts by weight of antimony trioxide was added, and test pieces for workability (fluidity), impact resistance, tensile test, bending test and flammability test were prepared, measured and evaluated. . The results are shown in Table 1.

The impact resistance, tensile test, bending test and flammability test were satisfied to some extent, but the workability (flowability) was poor.

Comparative Example 2 As shown in Table 1, the brominated polystyrene for a flame retardant obtained in Production Example 2 (the weight average molecular weight of polystyrene is 3.
02 × 10 ⁴ ) was added in the same manner as in Example 1 except that 30 parts by weight and 10 parts by weight of antimony trioxide were blended with 100 parts by weight of 6,6-nylon (Amilan CM3001 manufactured by Toray), and processability ( Flowability), impact resistance, tensile test, bending test and flammability test specimens were prepared, measured and evaluated.

The results are shown in Table 1.

The impact resistance, tensile test, bending test and flammability test were satisfied to some extent, but the workability (flowability) was poor.

Comparative Example 3 As shown in Table 1, the same procedure as in Example 1 was repeated except that 15 parts by weight of a commercially available brominated polystyrene having a weight average molecular weight of 200,000 in terms of polystyrene and 5 parts by weight of antimony trioxide were blended. Test pieces for workability (fluidity), impact resistance, tensile test and bending test were prepared, measured and evaluated. The result is
The results are shown in Table 1.

Although the impact resistance, tensile test and bending test were satisfied to some extent, the workability (flowability) was poor.

Comparative Example 4 As shown in Table 1, the brominated polystyrene for a flame retardant obtained in Production Example 2 (having a weight average molecular weight of 3.
02 × 10 ⁴ ) 15 parts by weight and 5 parts by weight of antimony trioxide were added, and the same procedure as in Example 1 was performed to prepare test pieces for workability (fluidity), impact resistance, tensile test and bending test. Then, it was measured and evaluated.

The results are shown in Table 1.

Although the impact resistance, tensile test and bending test were satisfied, the workability (flowability) was poor.

Example 3 and Comparative Examples 5 and 6 As shown in Table 2, bromination for a flame retardant obtained by the same production method as in Production Example 1 (weight average molecular weight in terms of polystyrene was 1.
12 × 10 ⁴ ), a commercially available brominated polystyrene having a molecular weight of 200,000 and a commercially available dibromostyrene polymer having a molecular weight of 50,000 are used as 6,6-nylon (Amylan CM3301 manufactured by Toray).
32.3 parts by weight, 16.1 parts by weight of antimony trioxide, and 100 parts by weight of glass fiber (glass fiber chopped strand 03M made by Asahi Glass Fiber Co., Ltd.
A419) 64.5 parts by weight, emulsion-polymerized Teflon (FLUONCD4 manufactured by Asahi IC Polymers Co., Ltd.) 2.2
2 parts by weight using a twin-screw extruder (L / D: 25).
Kneading was performed at 70 to 280 ° C. to prepare pellets.
Using these pellets, a melting temperature of 280 to 285 ° C,
Injection molding was performed at a mold temperature of 80 ° C. From these samples, workability (fluidity), impact resistance, tensile test, bending test and flammability test pieces were prepared and measured and evaluated respectively.
The results are shown in Table 2.

The brominated polystyrene for flame retardant of the present invention was superior in combustion performance and processability (fluidity) to other commercial agents.

Further, various evaluation results of the reinforced product in which 42.9 parts by weight of glass fiber (Glass Ron chopped strand 03MA419 made by Asahi Glass Fiber) are mixed with 100 parts by weight of 6,6-nylon (Amilan CM3001 made by Toray) are also shown. Shown in 2.

[0062]

[Table 2]

Example 4 and Comparative Examples 7 and 8 As shown in Table 3, the brominated flame retardant obtained by the same production method as in Production Example 1 (weight average molecular weight in terms of polystyrene was 1.
12 × 10 ⁴ ), a commercially available brominated polystyrene having a molecular weight of 200,000 and a commercially available tetrabromobisphenol-A phenoxy resin having a molecular weight of 20,000 are used as polybutylene terephthalate (hereinafter abbreviated as PBT, Novadur 501 manufactured by Mitsubishi Chemical Corporation).
0) 20 parts by weight and 4 parts by weight of antimony trioxide were added to 100 parts by weight, and a twin-screw extruder (L / D: 2) was used.
5) was kneaded at 240 to 250 ° C. to prepare pellets. Using these pellets, a melting temperature of 26
Injection molding was performed at 5 to 275 ° C and a mold temperature of 80 ° C.
From these samples, workability (fluidity), impact resistance, tensile test, bending test and flammability test pieces were prepared and measured and evaluated respectively. The results are shown in Table 3.

The brominated polystyrene for flame retardant of the present invention was superior in combustion performance and processability (fluidity) to other commercially available agents.

In addition, PBT (Novadul 5 manufactured by Mitsubishi Chemical)
The results of various evaluations for (010) are also shown in Table 3.

[0066]

[Table 3]

Example 5 and Comparative Examples 8 and 9 As shown in Table 4, bromination for a flame retardant obtained by the same production method as in Production Example 1 (weight average molecular weight in terms of polystyrene was 1.
12 × 10 ⁴ ), a commercially available brominated polystyrene having a molecular weight of 200,000 and a commercially available tetrabromobisphenol-A phenoxy resin having a molecular weight of 20,000, were added to 15 parts each of 15 parts by weight of PBT (Novadur 5010 manufactured by Mitsubishi Chemical).
8 parts by weight, 5.3 parts by weight of antimony trioxide, 52.6 parts by weight of glass fiber (Asahi glass fiber-made glassron chopped strand 03MA419), emulsion polymerization Teflon (FLUON made by Asahi IC Fluoropolymers)
CD4) 1.8 parts by weight, and twin screw extruder (L / D: 2
5) was kneaded at 240 to 250 ° C. to prepare pellets. Using these pellets, a melting temperature of 26
Injection molding was performed at 5 to 275 ° C and a mold temperature of 80 ° C.
From these samples, workability (fluidity), impact resistance, tensile test, bending test and flammability test pieces were prepared and measured and evaluated respectively. Table 4 shows the results.

The brominated polystyrene for flame retardant of the present invention was superior in processability (fluidity) to other commercially available agents, and was superior in flame retardancy to the commercially available tetrabromobisphenol-A phenoxy resin.

In addition, PBT (Novadul 5 made by Mitsubishi Chemical
010) 100 parts by weight of glass fiber (Asahi glass fiber made glassron chopped strand 0
3MA419) Table 4 also shows the results of various evaluations of the reinforced product containing 70.6 parts by weight.

[0070]

[Table 4]

[0071]

EFFECTS OF THE INVENTION The brominated polystyrene for flame retardant of the present invention and the flame-retardant resin composition comprising the same greatly improve processability without deteriorating mechanical properties, and are useful as flame retardants for synthetic resins. It is useful and can be used as a compounded flame retardant for a flame retardant resin, which is often used in various electric products and the like.

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Claims (4)

[Claims] 1. A weight average molecular weight in terms of polystyrene of 5,
Brominated polystyrene for flame retardants, characterized in that it is 000 to 15,000. 2. A flame-retardant resin composition comprising the brominated polystyrene for a flame retardant according to claim 1 and a synthetic resin. 3. The flame-retardant resin composition according to claim 2, which comprises 5 to 50 parts by weight of the brominated polystyrene for a flame retardant according to 100 parts by weight of a synthetic resin. . 4. 100 parts by weight of synthetic resin, 5 to 200 parts by weight of brominated polystyrene for flame retardant, 5 to 200 parts by weight of glass fiber, 1 part of antimony trioxide or sodium antimonate as claimed in claim 1. The flame-retardant resin composition according to claim 2, wherein the flame-retardant resin composition comprises ˜140 parts by weight and the emulsion-polymerized Teflon is 0.1 to 10 parts by weight.