CN108117680B - Rubber composition and preparation method thereof - Google Patents
Rubber composition and preparation method thereof Download PDFInfo
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- CN108117680B CN108117680B CN201711475831.4A CN201711475831A CN108117680B CN 108117680 B CN108117680 B CN 108117680B CN 201711475831 A CN201711475831 A CN 201711475831A CN 108117680 B CN108117680 B CN 108117680B
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K13/00—Use of mixtures of ingredients not covered by one single of the preceding main groups, each of these compounds being essential
- C08K13/02—Organic and inorganic ingredients
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L15/00—Compositions of rubber derivatives
- C08L15/005—Hydrogenated nitrile rubber
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K2201/00—Specific properties of additives
- C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K
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Abstract
The invention provides a rubber composition, and belongs to the field of rubber preparation. The rubber composition provided by the invention comprises the following components in parts by weight: 100 parts of rubber, 0.1-20 parts of multi-component maleimide, 0.01-20 parts of vulcanizing agent and 1-230 parts of auxiliary agent. The multicomponent maleimide of the invention replaces the traditional auxiliary crosslinking agent triallyl isocyanurate to be used as the auxiliary crosslinking agent, can achieve the effect of obviously improving the compression permanent deformation performance of rubber products, and can accelerate the vulcanization speed. The data of the examples show that the compression set (37.6%) of the rubber composition provided by the invention is reduced by 38.5% compared with the compression set (61.2%) of the rubber composition obtained by the traditional vulcanization system, and the rubber composition has excellent compression set performance.
Description
Technical Field
The invention relates to the technical field of rubber preparation, in particular to a rubber composition and a preparation method thereof.
Background
The nitrile rubber is a special rubber with excellent heat resistance, weather resistance, ozone resistance and oil resistance, is mainly applied to oil field exploitation and the automobile industry, and is widely applied to the field of high-temperature and high-pressure severe environment sealing elements and the manufacture of products such as fuel rubber tubes and the like.
With the development of industry, especially the continuous development of oil field mining industry and the continuous progress of automobile industry, the application environment of rubber products is more and more severe, so that the requirement on nitrile rubber products is higher and higher, the requirement on the service life of a sealing element under the condition of high temperature and oil resistance is higher and higher, and the requirement on the compression permanent deformation performance of the products is higher and higher.
As a prior art for solving such problems, rubber compositions containing nitrile rubber or hydrogenated nitrile rubber are generally compounded with conventional vulcanization systems, i.e., peroxide crosslinking agents and triallyl isocyanurate (TAIC), and the resulting rubber articles have poor compression set properties.
Disclosure of Invention
In view of the above, the present invention is directed to a rubber composition and a method for preparing the same. The rubber composition provided by the invention has excellent compression set performance.
In order to achieve the above object, the present invention provides the following technical solutions:
the invention provides a rubber composition which comprises the following components in parts by weight: 100 parts of rubber, 0.1-20 parts of multi-component maleimide, 0.01-20 parts of a vulcanizing agent and 1-230 parts of an auxiliary agent, wherein the rubber is hydrogenated nitrile rubber or nitrile rubber, and the multi-component maleimide at least contains one of the structures shown in formula I:
in the formula I, n is an integer of 0-30.
Preferably, the vulcanizing agent is sulfur or a peroxide vulcanizing agent.
Preferably, the peroxide curing agent is dicumyl peroxide.
Preferably, the weight part of the multicomponent maleimide is 0.2-10 parts.
Preferably, the auxiliary agent comprises the following components in parts by weight based on 100 parts by weight of rubber: 0-20 parts of an activating agent, 1-10 parts of an anti-aging agent, 0-150 parts of a filler, 0-30 parts of a plasticizer, 0-10 parts of an operation aid and 0-10 parts of a promoter.
Preferably, the filler is one or more of carbon black, mineral filler, talc, calcium carbonate, china clay, white carbon black or aluminum hydroxide.
Preferably, the processing aid is polyethylene wax and/or stearic acid.
The invention also provides a preparation method of the rubber composition in the technical scheme, which comprises the following steps:
(1) mixing rubber, an auxiliary agent, a vulcanizing agent and multi-component maleimide for mixing to obtain a mixed material;
(2) and (2) vulcanizing the mixed material obtained in the step (1) to obtain the rubber composition.
Preferably, the temperature for mixing in the step (1) is 60-160 ℃, and the time for mixing is 1-20 min.
Preferably, the vulcanization temperature in the step (2) is 120-200 ℃, and the vulcanization time is 5-90 min.
The invention provides a rubber composition which comprises the following components in parts by weight: 100 parts of rubber, 0.1-20 parts of multi-component maleimide, 0.01-20 parts of vulcanizing agent and 1-230 parts of auxiliary agent, wherein the rubber is hydrogenated nitrile rubber or nitrile rubber. The multi-component maleimide has a plurality of active reaction functional groups of maleimide, under the initiation action of a vulcanizing agent, the multi-component maleimide can generate a crosslinking reaction with unsaturated bonds on a rubber main molecular chain to generate a relatively stable crosslinking bridge of a carbon chain, and the crosslinking density of rubber is increased. As can be seen from the examples, the rubber composition provided by the invention has a compression set (37.6%) reduced by 38.5% compared with the compression set (61.2%) of the rubber composition obtained by the conventional vulcanization system, and has excellent compression set performance.
Furthermore, the multicomponent maleimide contains an aromatic structure with a plurality of benzene rings, has good affinity with the filler, can improve the interaction between the filler and the rubber, and improves the dispersion degree of the filler, thereby improving the wear resistance of the rubber composition. As can be seen from the examples, the Akron abrasion weight loss (0.154g) of the rubber composition provided by the present invention is reduced by 20.7% compared to the Akron abrasion weight loss (0.194g) of the rubber composition vulcanized by the conventional vulcanization system.
Detailed Description
The invention provides a rubber composition which comprises the following components in parts by weight: 100 parts of rubber, 0.1-20 parts of multi-component maleimide, 0.01-20 parts of vulcanizing agent and 1-230 parts of auxiliary agent, wherein the rubber is hydrogenated nitrile rubber or nitrile rubber; the multi-component maleimide at least contains one of the structures shown in the formula I:
in the formula I, n is an integer of 0-30.
The rubber composition provided by the invention comprises 100 parts by weight of rubber, wherein the rubber is nitrile rubber or hydrogenated nitrile rubber. The source of the nitrile rubber and hydrogenated nitrile rubber is not particularly limited in the present invention, and commercially available products known to those skilled in the art, specifically, HNBR-ZN35258 and NBR220S from Zainan technologies (Shanghai) Co.
The rubber composition provided by the invention comprises 0.1-20 parts by weight of multi-component maleimide, preferably 0.2-10 parts, more preferably 1-6 parts, and most preferably 2-4 parts. In the invention, the multi-component maleimide at least comprises one of structures shown in formula I, and n is preferably an integer of 1-20. The present invention is not particularly limited as to the source of said multicomponent maleimide, and may be obtained by using commercially available products well known to those skilled in the art, such as topwizapi from tsukamur chemical (shanghai) ltd. The multi-component maleimide provided by the invention has a plurality of active reaction functional groups of maleimide, and can generate cross-linking reaction with unsaturated bonds on a rubber main molecular chain under the initiation action of a vulcanizing agent, so that a relatively stable cross-linking bridge of a carbon chain is generated, the cross-linking density of rubber is increased, and the compression permanent deformation of the rubber composition is improved.
The rubber composition provided by the invention comprises 0.01-20 parts by weight of vulcanizing agent, preferably 1-10 parts by weight, and more preferably 4-6 parts by weight. In the present invention, the vulcanizing agent is preferably sulfur or a peroxide vulcanizing agent; the peroxide curative is preferably dicumyl peroxide (DCP).
The rubber composition provided by the invention comprises 1-230 parts by weight of an auxiliary agent, preferably 30-180 parts by weight, and more preferably 70-100 parts by weight. In the invention, the auxiliary agent preferably comprises the following components in parts by weight, based on 100 parts by weight of rubber: 0-20 parts of an activating agent, 1-10 parts of an anti-aging agent, 0-150 parts of a filler, 0-30 parts of a plasticizer, 0-10 parts of an operation aid and 0-10 parts of a promoter.
In the invention, the auxiliary agent preferably comprises 5-15 parts by weight of an active agent, and more preferably 6-10 parts by weight. The invention is not limited to any particular type of active agent, and active agents known to those skilled in the art, such as zinc oxide, may be used.
In the invention, the auxiliary agent preferably comprises 1.5-6 parts by weight of the anti-aging agent, and more preferably 2-4 parts by weight. The kind of the antioxidant is not particularly limited in the present invention, and antioxidants known to those skilled in the art may be used, specifically, antioxidant 4020, antioxidant 4010NA, antioxidant 445, and antioxidant RD.
In the invention, the auxiliary agent preferably comprises 10-90 parts by weight of filler, and more preferably 30-60 parts by weight of filler. The filler is preferably one or more of carbon black, mineral filler, talcum powder, calcium carbonate, argil, white carbon black or aluminum hydroxide; when the filler is a mixture, the weight ratio of the carbon black, the mineral filler, the talcum powder, the calcium carbonate, the argil, the white carbon black and the aluminum hydroxide in the filler mixture is not particularly limited, and the mixture with any proportion can be adopted. In the present invention, there is no particular requirement for the source of the filler, and commercially available products known to those skilled in the art may be used, specifically, carbon black N134, N220, N234, N330, N326, N375, N550, N660, N770 or talc. In the invention, the multi-component maleimide has good affinity with the filler, so that the interaction between the filler and rubber can be improved, the dispersion degree of the filler is improved, and the wear resistance of the rubber composition is improved.
In the invention, the auxiliary agent preferably comprises 5-15 parts by weight of a plasticizer, more preferably 8-12 parts by weight, and most preferably 10 parts by weight. In the present invention, there is no particular limitation on the kind of the plasticizer, and any plasticizer known to those skilled in the art may be used, specifically, for example, the environmentally friendly ether ester type plasticizer TP-95.
In the invention, the auxiliary agent preferably comprises 2-8 parts by weight of operation auxiliary agent, and more preferably 4-6 parts. The present invention is not limited to any particular kind of processing aid, and may be any processing aid known to those skilled in the art, such as stearic acid or polyethylene wax.
In the invention, the auxiliary agent preferably comprises 1-6 parts by weight of an accelerator, and more preferably 2.5-5 parts by weight. The type of the promoter used in the present invention is not particularly limited, and any promoter known to those skilled in the art may be used, specifically, N-tetramethyldithiobisthiocarboxamine (TMTD), 2' -Dithiodibenzothiazole (DM), and N-cyclohexyl-2-benzothiazolesulfenamide (CZ).
The invention also provides a preparation method of the rubber composition in the technical scheme, which comprises the following steps:
(1) mixing rubber, an auxiliary agent, a vulcanizing agent and multi-component maleimide for mixing to obtain a mixed material;
(2) and (2) vulcanizing the mixed material obtained in the step (1) to obtain the rubber composition.
The rubber, the auxiliary agent, the vulcanizing agent and the multi-component maleimide are mixed and mixed to obtain a mixed material. In the invention, the mixing temperature is preferably 60-160 ℃, and more preferably 80-150 ℃; the mixing time is preferably 1 to 20min, and more preferably 3 to 10 min.
In the invention, the rubber, the auxiliary agent, the vulcanizing agent and the multi-component maleimide are preferably added in sequence, and the auxiliary agent and the rubber are mixed and mixed to obtain a premixed material; after the temperature of the premixed material is lower than 120 ℃, a vulcanizing agent and multi-component maleimide are added. In the invention, the temperature when the vulcanizing agent and the multicomponent maleimide are added is preferably 80-100 ℃.
The preparation method of the auxiliary agent is not particularly limited in the invention, and the auxiliary agent can be prepared by adopting a preparation method of a composition well known to a person skilled in the art.
After the mixed material is obtained, the mixed material is vulcanized to obtain the rubber composition. In the invention, the vulcanization temperature is preferably 120-200 ℃, and more preferably 160-180 ℃; the vulcanizing time is preferably 5-90 min, and more preferably 10-40 min.
The mixing and vulcanizing device is not particularly limited, and devices known to those skilled in the art can be adopted, specifically, an internal mixer is adopted for mixing, and a vulcanizing machine is adopted for vulcanizing.
The rubber composition and the method for producing the same according to the present invention will be described in detail with reference to the following examples, but they should not be construed as limiting the scope of the present invention.
Example 1
The rubber composition comprises the following components in parts by weight: 100 parts of hydrogenated nitrile rubber (HNBR-ZN35258), 5.0 parts of zinc oxide, 1.0 part of stearic acid, N77430 parts, N55030 parts, 4451.5 parts of anti-aging agent, TP-955.0 parts, 4.0 parts of DCP and 1.0 part of PAPI.
The preparation method comprises the following steps:
(1) putting HNBR-ZN35258, zinc oxide, stearic acid, N774, N550, an anti-aging agent 445 and TP-95 into an internal mixer, mixing for 6 minutes at 100-150 ℃ to obtain a premixed material, and adding DCP and PAPI to mix for 4 minutes after the temperature of the premixed material is lower than 100 ℃ to obtain a mixed material;
(2) and vulcanizing the mixed materials in a vulcanizing machine at 160-180 ℃ for 20 minutes, and then carrying out molding, material cutting and trimming to obtain the rubber composition.
Characterizing the Mooney viscosity of the rubber composition using the test standard ASTM D1646-07; the tensile strength is characterized using the test standard ASTM D412-2006; adopting an enterprise internal standard to represent the tensile modulus; the rubber compositions were tested for aging using ASTM D573-04 (2015); the abrasion resistance of the rubber composition is tested by GB/T1689-; the rubber compositions were tested for constant set compression set using GB/T7759-2015.
The results of the performance tests are shown in Table 1.
Example 2
Rubber compositions were prepared using the same raw materials and preparation method as in example 1, except that the amount of PAPI was 1.5 parts, and the raw material ratios and the performance test results were shown in Table 1.
Example 3
Rubber compositions were prepared using the same raw materials and preparation method as in example 1, except that the amount of PAPI was 2.0 parts, and the raw material ratios and the performance test results were shown in Table 1.
Example 4
The rubber composition comprises the following components in parts by weight: 100 parts of hydrogenated nitrile rubber (HNBR), 5.0 parts of zinc oxide, 1.0 part of stearic acid, 77430 parts of N55030 parts of antioxidant 4451.5 parts of TP-955.0 parts of DCP 4.0 parts of PAPI2.0 parts of rubber composition is prepared according to the method of example 1, and the performance test results are shown in Table 2.
Example 5
The rubber composition was prepared using the same raw materials and preparation method as in example 4 except that PAPI was 4.0 parts, and the raw material ratios and the performance test results were shown in Table 2.
Example 6
The rubber composition comprises the following components in parts by weight: 100 parts of hydrogenated nitrile rubber (HNBR), 5.0 parts of zinc oxide, 1.0 part of stearic acid, 1.5 parts of WB222 (polyethylene wax), 15 parts of talcum powder, N77420 parts, N55030 parts, 4451.5 parts of anti-aging agent, TP-9510 parts, S1.0 parts, TMTD 2.0 parts, DM 1.0 part, CZ 1.0 part and PAPI2 parts, and a rubber composition is prepared according to the method of example 1, and the performance test results are shown in Table 2.
Example 7
The rubber composition comprises the following components in parts by weight: 100 parts of nitrile rubber (NBR220S), 5.0 parts of zinc oxide, 1.0 part of stearic acid, 77430 parts of N33030 parts, 1.5 parts of antioxidant RD, TP-955.0 parts of DCP and 0.5 part of PAPI, and the rubber compositions prepared by the method of example 1 and having the performance test results shown in Table 3.
Example 8
Rubber compositions were prepared using the same raw materials and preparation methods as in example 7, except that the amount of PAPI was 1.5 parts, and the raw material ratios and the performance test results were shown in Table 3.
Example 9
The rubber composition comprises the following components in parts by weight: 100 parts of nitrile rubber (NBR220S), 5.0 parts of zinc oxide, 1.0 part of stearic acid, 77430 parts of N33030 parts, 1.5 parts of antioxidant RD, TP-9510 parts, 1.0 part of S, 1.5 parts of TMTD, 0.5 part of DM, 0.5 part of CZ and 0.5 part of PAPI, rubber compositions were prepared according to the method of example 1, and the results of the performance tests are shown in Table 3.
Example 10
A rubber composition was prepared using the same raw materials and preparation method as in example 9, except that the amount of PAPI was 1.0 part, and the raw material ratios and the performance test results were shown in Table 3.
Comparative example 1
Rubber compositions were prepared using the same raw materials and preparation method as in example 1 except that 1.0 part of PAPI was replaced with 1.5 parts of TAIC, and the raw material ratios and performance test results are shown in Table 1.
Comparative example 2
Rubber compositions were prepared using the same raw materials and preparation method as in example 4 except that 2.0 parts of PAPI was replaced with 1.5 parts of TAIC and WB222 and talc were not used, TP-95 was 10 parts, and the material ratios and performance test results are shown in Table 2.
Comparative example 3
The rubber composition was prepared using the same raw materials and preparation method as in comparative example 2 except that 2.0 parts of PAPI was additionally added, and the raw material ratio and the performance test results are shown in Table 2.
Comparative example 4
Rubber compositions were prepared using the same raw materials and preparation methods as in example 6 except that no PAPI was added and the raw material ratios and performance test results were shown in Table 2.
Comparative example 5
A rubber composition was prepared using the same raw materials and preparation method as in example 7, except that 0.5 part of PAPI was replaced with 1.5 parts of TAIC and TP-95 was 10 parts, and the raw material ratios and the performance test results were as shown in Table 3.
Comparative example 6
Rubber compositions were prepared using the same raw materials and preparation methods as in example 9, except that no PAPI was added, and the raw material ratios and performance test results are shown in Table 3.
Table 1 raw material ratios and performance test results
As can be seen from Table 1, the compression set (37.6%) of the rubber composition of example 3 provided by the present invention was reduced by 38.6% as compared to the compression set (61.2%) of the hydrogenated nitrile rubber composition obtained in comparative example 1 using TAIC as a crosslinking aid.
Meanwhile, the weight loss of Akron abrasion (0.154g) of the rubber composition of example 3 provided by the present invention was also reduced by 20% as compared to the weight loss of Akron abrasion (0.194g) of comparative example 1, and it can be seen that the abrasion resistance of the rubber composition of the present invention was significantly improved as compared to the comparative example.
In addition, the dynamic loss factor Tan (0.148) of the rubber composition of example 3 provided by the present invention was also reduced by 12% as compared with the dynamic loss factor Tan (0.168) of comparative example 1, and it can be seen that the rubber composition of the present invention has a significant improvement in the relative ratio of filler dispersion and heat generation.
Table 2 raw material ratios and performance test results
As can be seen from table 2: when the vulcanizing agent is peroxide, the compression set of the hydrogenated nitrile rubber composition (examples 4 and 5) prepared by using the multi-component maleimide as the crosslinking assistant is reduced by 26-36% compared with the hydrogenated nitrile rubber composition (comparative example 2) prepared by using TAIC as the crosslinking assistant; when the vulcanizing agent was sulfur, the amount of compression set of the hydrogenated nitrile rubber composition prepared by adding multicomponent maleimide as a crosslinking aid (example 6) was reduced by 6.6% as compared to the hydrogenated nitrile rubber composition of comparative example 4. The multi-component maleimide serving as a crosslinking assistant obviously improves the compression set resistance of the hydrogenated nitrile rubber composition.
Meanwhile, compared with the rubber composition in the comparative example 2, the rubber composition in the examples 4 and 5 of the invention has the advantages that the Akron abrasion weight loss is reduced by 44%, and the abrasion resistance of the rubber composition provided by the invention is obviously improved.
Table 3 raw material ratios and performance test results
As can be seen from Table 3, the nitrile rubber composition prepared with the multicomponent maleimide as the crosslinking coagent (example 7) had a reduction in compression set of 47% when compared to the nitrile rubber composition prepared with TAIC as the crosslinking coagent (comparative example 5) when the vulcanizing agent was a peroxide; when the vulcanizing agent was sulfur, the amount of compression set of the hydrogenated nitrile rubber composition prepared by adding multicomponent maleimide as a crosslinking aid (example 10) was reduced by 19% compared to the hydrogenated nitrile rubber composition of comparative example 6. The compression set resistance of the nitrile rubber composition is obviously improved by taking the multi-component maleimide as a crosslinking assistant.
At the same time, the weight loss of Akron abrasion was reduced by 15% for the nitrile rubber composition prepared with the addition of multicomponent maleimide as a crosslinking aid (example 10) compared to the nitrile rubber composition of comparative example 6. The nitrile rubber composition of the present invention has excellent abrasion resistance.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (7)
1. A rubber composition comprises the following components in parts by weight: 100 parts of rubber, 0.1-20 parts of multi-component maleimide, 0.01-20 parts of vulcanizing agent and 1-230 parts of auxiliary agent; the rubber is hydrogenated nitrile rubber or nitrile rubber, and the multi-component maleimide at least contains one of the structures shown in the formula I:
in the formula I, n is an integer of 1-30;
based on 100 parts by weight of rubber, the auxiliary agent comprises the following components in parts by weight: 0-20 parts of an activator, 1-10 parts of an anti-aging agent, 0-150 parts of a filler, 0-30 parts of a plasticizer, 0-10 parts of an operation aid and 1-6 parts of a promoter; the accelerant is N, N-tetramethyl dithio carbonyl amine, 2' -dithio dibenzothiazyl, N-cyclohexyl-2-benzothiazole sulfonamide;
the vulcanizing agent is dicumyl peroxide;
the anti-aging agent is anti-aging agent 4020, anti-aging agent 4010NA, anti-aging agent 445 or anti-aging agent RD.
2. The rubber composition according to claim 1, wherein the multicomponent maleimide is present in an amount of 0.2 to 10 parts by weight.
3. The rubber composition of claim 1, wherein the filler is one or more of carbon black, talc, calcium carbonate, china clay, white carbon, or aluminum hydroxide.
4. The rubber composition of claim 1, wherein the processing aid is a polyethylene wax and/or stearic acid.
5. A process for producing the rubber composition according to any one of claims 1 to 4, comprising the steps of:
(1) mixing rubber, an auxiliary agent, a vulcanizing agent and multi-component maleimide for mixing to obtain a mixed material;
(2) and (2) vulcanizing the mixed material obtained in the step (1) to obtain the rubber composition.
6. The method according to claim 5, wherein the temperature of the kneading in the step (1) is 60 to 160 ℃ and the kneading time is 1 to 20 min.
7. The preparation method according to claim 5, wherein the temperature of the vulcanization in the step (2) is 120 to 200 ℃ and the time of the vulcanization is 5 to 90 min.
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CN113248836B (en) * | 2021-05-24 | 2023-06-20 | 大冢材料科技(上海)有限公司 | Ethylene propylene diene monomer composition and preparation method thereof |
CN116855004B (en) * | 2023-08-29 | 2024-02-20 | 东莞市万觅新材料科技有限公司 | Rubber composition and preparation method thereof |
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