CN110760026B - Synthesis method of tetrafluoroethylene-propylene rubber and tetrafluoroethylene-propylene rubber thereof - Google Patents
Synthesis method of tetrafluoroethylene-propylene rubber and tetrafluoroethylene-propylene rubber thereof Download PDFInfo
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- CN110760026B CN110760026B CN201810837728.8A CN201810837728A CN110760026B CN 110760026 B CN110760026 B CN 110760026B CN 201810837728 A CN201810837728 A CN 201810837728A CN 110760026 B CN110760026 B CN 110760026B
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F214/18—Monomers containing fluorine
- C08F214/26—Tetrafluoroethene
- C08F214/262—Tetrafluoroethene with fluorinated vinyl ethers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
- C08F2/24—Emulsion polymerisation with the aid of emulsifying agents
- C08F2/30—Emulsion polymerisation with the aid of emulsifying agents non-ionic
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/04—Monomers containing three or four carbon atoms
- C08F210/06—Propene
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F216/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F216/12—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
- C08F216/14—Monomers containing only one unsaturated aliphatic radical
- C08F216/1408—Monomers containing halogen
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Abstract
The invention relates to a synthetic method of tetrafluoroethylene-propylene rubber, which mainly improves the method that tetrafluoroethylene and propylene monomers are used as raw materials, in the process of preparing the tetrafluoroethylene-propylene rubber by an emulsion polymerization method, olefin containing bromine or iodine in a vulcanization point monomer is added, and I (CF) is selected2)nI is a chain transfer agent, wherein n is an integer of 2-6. The tetrapropylene fluoride rubber obtained by the method has the characteristics of low Mooney viscosity, high tensile strength and low permanent compression set, and has excellent steam resistance and alkali resistance. The method of the invention adopts water as a medium for reaction, and through the selection of the chain transfer agent and the initiator, the excellent-performance tetrapropylene fluorocarbon rubber can be obtained only under the condition of adding the vulcanization point monomer, and other various additives are not needed, so that the raw material cost is saved, and the operation is simple.
Description
Technical Field
The invention relates to the technical field of high molecular substance synthesis, in particular to a synthetic method of tetrafluoroethylene-propylene rubber.
Background
The tetrapropylene fluoride rubber is a fluorine-containing elastomer and has excellent steam resistance, alkali resistance and high electrical insulation performance. This is a unique property which vinylidene fluoride fluororubbers do not have. The composite material is widely applied to the fields of heat-resistant electric wires, steam-resistant products and alkali-resistant products, and is mainly used as an O-shaped ring, a sealing element, a diaphragm, a gasket, a rubber sheet and the like.
In the prior art, tetrafluoroethylene-propylene is adopted as a main comonomer, a redox system is adopted, persulfate is taken as an initiator, hydrosulfite and ferric salt are taken as reducing agents, and emulsion polymerization is adopted under the condition of high pressure reaction. The obtained product has the advantages of large molecular weight, high Mooney viscosity, low polymerization speed and deep color of emulsion and copolymer. High pressure polymerization thereof, high safety; the obtained product has high Mooney viscosity, is not suitable for an extrusion molding process, and has lower strength and high compression set resistance value.
Aiming at the problems in the prior art, the application provides a novel synthetic method of tetrafluoroethylene-propylene rubber.
Disclosure of Invention
The first purpose of the invention is to provide a preparation method of tetrapropylene fluoride rubber, which mainly improves the following steps: using tetrafluoroethylene and propylene monomers as raw materials, adding olefin containing bromine or iodine in a vulcanization point monomer in the process of preparing tetrapropylene fluoride rubber by an emulsion polymerization method, and selecting I (CF)2)nI is a chain transfer agent, wherein n is an integer of 2-6;
the alkene containing bromine or iodine is one or more of perfluoro-4-bromo-1-butene, perfluoro bromoethyl vinyl ether, perfluoro iodoethyl vinyl ether, perfluoro-4-iodo-1-butene, trifluoro iodoethylene or trifluoro bromoethylene.
According to the method, the vulcanization point monomer is added, and the chain transfer agent is selected, so that the performance of the obtained tetrapropylene fluoride rubber can be effectively improved, and the tetrapropylene fluoride rubber with lower Mooney viscosity, high tensile strength and low permanent deformation can be obtained.
Preferably, a redox initiator is adopted in the reaction process, the redox initiator is a mixture of potassium persulfate and ammonium persulfate, and the reduction initiator is sodium metabisulfite. In the initiator, the decomposition temperature of ammonium persulfate is low, the half-life period is short under the reaction temperature condition, the decomposition temperature of potassium persulfate is high, but the half-life period is long, and the initiation temperature of the ammonium persulfate and the initiation temperature of the potassium persulfate can be effectively reduced by adding a reducing agent system, so that the polymerization reaction is effectively initiated and continuously carried out.
Preferably, the usage ratio of the tetrafluoroethylene to the propylene is 40: 60-80: 20.
Preferably, the addition amount of the vulcanization point monomer is 0.1-3% of the mass of the tetrafluoroethylene and propylene monomers.
Further preferably, the cure site monomer is perfluoroiodoethyl vinyl ether, perfluoro-4-iodo-1-butene or trifluoroiodoethylene.
Preferably, the method of the present invention comprises the steps of:
adding deionized water, a pH buffering agent and an emulsifier into a reaction kettle, vacuumizing the reaction kettle, adding the tetrafluoroethylene and propylene monomers into the reaction kettle until the pressure in the reaction kettle is 0.5-3.0 MPa, heating the reaction kettle to 60-100 ℃, adding the vulcanization point monomer and the chain transfer agent into the reaction kettle, adding the redox initiator to initiate polymerization, and supplementing and adding the tetrafluoroethylene and propylene monomers in the reaction process to maintain the pressure in the reaction kettle at the initial pressure to complete the reaction.
The reaction pressure is too low to be beneficial to the reaction, but the pressure is too high to require too high material of the reaction kettle, which is not beneficial to the production, and the Mooney viscosity of the obtained product is high. The reaction temperature is lower than 60 ℃, the activity of the initiator is reduced, and the reaction is influenced; above 100 ℃, the decomposition rate of the initiator is too fast, which is not favorable for reaction control. The reaction is most advantageously carried out under the pressure and temperature conditions described above.
Preferably, the emulsifier is a perfluoropolyether peroxide.
More preferably, the addition amount of the emulsifier is 0.15 to 0.25% by mass of the polymerized monomer.
Preferably, in the redox initiation system, the mass ratio of potassium persulfate to ammonium persulfate is 1-5: 1, and the mass sum ratio of sodium metabisulfite to potassium persulfate to ammonium persulfate is 1: 1-3.
Further preferably, the mass ratio of the potassium persulfate to the ammonium persulfate is 1:1, and the mass sum ratio of the sodium metabisulfite to the potassium persulfate to the ammonium persulfate is 1: 2.
Preferably, the addition amount of the redox initiator is 0.1-1% by mass of the polymerized monomer.
More preferably, the addition amount of the redox initiator is 0.4 to 0.6% by mass of the polymerization monomer.
Preferably, the addition amount of the chain transfer agent is 0.1-2% of the mass of the polymerized monomer.
More preferably, the amount of the chain transfer agent added is 0.3 to 1.2% by mass of the polymerized monomer.
The tetrapropylene fluoride rubber obtained by the reaction of the method can be coagulated by using a saline strong electrolyte aqueous solution as a coagulant (such as magnesium chloride, sodium chloride, ammonium carbonate and the like).
Furthermore, in subsequent application, the rubber can be treated by other modes such as vulcanization and the like according to different requirements to prepare products suitable for different fields.
More preferably, the method of the present invention comprises the steps of:
adding deionized water, a pH buffering agent and an emulsifying agent into a reaction kettle, vacuumizing the reaction kettle, and adding a mixture of a raw material and a water-soluble organic solvent in a molar ratio of 70:30 of tetrafluoroethylene and propylene monomers, heating the reaction kettle to 85-95 ℃ until the pressure in the reaction kettle is 0.8-1.2 MPa, adding 1.0-1.5% of the mass of the polymerization monomers of a vulcanization point monomer perfluoroiodoethyl vinyl ether and 1.0-1.2% of the mass of the polymerization monomers of a chain transfer agent perfluorobutyl diiodo into the reaction kettle, adding a redox initiator potassium persulfate, ammonium persulfate and sodium metabisulfite, wherein the addition amount of the redox initiator is 0.4-0.6% of the mass of the polymerization monomers, the mass ratio of the potassium persulfate to the ammonium persulfate is 1:1, the mass sum ratio of the sodium metabisulfite to the potassium persulfate to the ammonium persulfate is 1:2, initiating a polymerization reaction, and supplementing the tetrafluoroethylene and propylene monomers in the reaction process to maintain the pressure in the reaction kettle at an initial pressure, thus completing the reaction.
The invention also aims to protect the tetrapropylene fluoride rubber prepared by the method.
The scheme of the invention has the following beneficial effects:
1) according to the method, water is used as a medium for reaction, and the chain transfer agent and the initiator are selected, so that the excellent-performance tetrapropylene fluoride rubber can be obtained only under the condition of adding the vulcanization point monomer, other various additives are not needed, the raw material cost is saved, the reaction can be carried out under lower pressure, and the operation is simple.
2) The tetrapropylene fluoride rubber obtained by the invention has the characteristics of low Mooney viscosity, high tensile strength and low permanent compression set, and has excellent steam and alkali resistance. The Mooney viscosity is 15-45 (1+10min @121 ℃), the tensile strength is 18-22 MPa, the elongation is 265-295%, and the permanent compression set is 20-30% (hot air, 200 ℃ x 70 h).
3) The tetrapropylene fluoride rubber is generally vulcanized by adopting a peroxide vulcanization system at the later stage, and the invention can provide a crosslinking point for the vulcanization of the peroxide vulcanization system by adding a vulcanization point monomer and a chain transfer agent with 'I'. Because the bond energy of the C-Br or C-I bond is low, the Br and I atoms are easy to be removed to form free radicals in the free radical vulcanization process, and the free radicals and a cross-linking agent are subjected to addition reaction to form a cross-linked network structure, so that the vulcanization purpose is achieved, and the application performance of the product is improved. The rubber prepared by the method has high vulcanization speed, wherein the first-stage vulcanization is carried out at 180 ℃ for 10min, and the second-stage vulcanization is carried out at 230 ℃ for 4 h.
Detailed Description
The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
Example 1
The embodiment relates to a preparation method of tetrafluoroethylene-propylene rubber, which comprises the following steps:
adding 3L of deionized water, 2g of dipotassium hydrogen phosphate and 3g of emulsifier ammonium perfluoropolyethercarboxylate into a 5L stainless steel reaction kettle with a stirrer, repeatedly pressurizing with nitrogen, vacuumizing and degassing, adding a mixed monomer with the molar ratio of tetrafluoroethylene to propylene being 70:30 into the reaction kettle, increasing the pressure to 0.5MPa, starting the reaction kettle stirrer, then increasing the temperature to 70 ℃, continuously adding the mixed monomer and increasing the pressure to 2.0MPa, adding 10g of vulcanization point monomer perfluorobromoethyl vinyl ether through a metering pump, adding a mixture of 2.5g of ammonium persulfate and 2.5g of potassium persulfate, 2.5g of sodium metabisulfite as an oxidation reduction initiator, and 5g of I (CF) as an initiator (5 g of sodium metabisulfite is 2.5g of sodium metabisulfite)2CF2)2I, when the polymerization reaction is started and the pressure of the reaction kettle is reduced by 0.01MPa, supplementing TFE/P mixed monomer into the reaction kettle, and maintaining the pressure in the reaction kettleIs 2.0 MPa.
The reaction was stopped when 1500g of TFE/P was continuously fed. And (3) obtaining the tetrafluoroethylene-propylene rubber emulsion, coagulating the tetrafluoroethylene-propylene rubber emulsion by using a magnesium chloride aqueous solution, washing the tetrafluoroethylene-propylene rubber emulsion by using deionized water, and continuously drying the tetrafluoroethylene-propylene rubber emulsion for 14 hours in a vacuum drying oven at the temperature of 90 ℃ and the pressure of-0.09 MPa to obtain a rubber product.
The Mooney viscosity of the product, 30(ML (1+10min @121 ℃)), was vulcanized using the following recipe.
The vulcanization formula is as follows:
| raw rubber | 100 portions of |
| ShuangErwu, 75% | 4 |
| TAIC | 3 |
| N990 | 20 |
| One stage vulcanization | 170℃×10min |
| Two stage vulcanization | 232℃×4h |
The results obtained were:
example 2
The embodiment relates to a preparation method of tetrafluoroethylene-propylene rubber, which comprises the following steps:
A5L stainless steel reaction kettle with a stirrer is added with 3L deionized water, 2g dipotassium hydrogen phosphate and 3g emulsifier, after nitrogen pressurization and evacuation and degassing are repeatedly carried out, a mixed monomer of tetrafluoroethylene and propylene is added into the reaction kettle, the molar ratio of TFE/P is 70:30, the pressure is increased to 0.5MPa, the reaction kettle stirrer is started, then the temperature is increased to 70 ℃, the mixed monomer of TFE/P is 70:30 is continuously added, the pressure is increased to 3.0MPa, 10g perfluoro bromoethyl vinyl ether of a vulcanization point monomer, 2.5g ammonium persulfate and 2.5g potassium persulfate are mixed through a metering pump, 2.5g partial weight of sodium sulfite and 5g of I (CF) of a chain transfer agent are added2CF2)2I, starting a polymerization reaction, and supplementing TFE/P mixed monomer into the reaction kettle when the pressure of the reaction kettle is reduced by 0.01MPa, and maintaining the pressure in the reaction kettle to be 3.0 MPa.
The reaction was stopped when 1500g of TFE/P was continuously fed. And (3) obtaining the tetrafluoroethylene-propylene rubber emulsion, coagulating the tetrafluoroethylene-propylene rubber emulsion by using a magnesium chloride aqueous solution, washing the tetrafluoroethylene-propylene rubber emulsion by using deionized water, and continuously drying the tetrafluoroethylene-propylene rubber emulsion for 14 hours in a vacuum drying oven at the temperature of 90 ℃ and the pressure of-0.09 MPa to obtain a rubber product.
Example 3
The embodiment relates to a preparation method of tetrafluoroethylene-propylene rubber, which comprises the following steps:
A5L stainless steel reaction kettle with a stirrer is added with 3L deionized water, 2g dipotassium hydrogen phosphate and 3g emulsifier, after nitrogen pressurization and evacuation and degassing are repeatedly carried out, a mixed monomer of tetrafluoroethylene and propylene is added into the reaction kettle, the molar ratio of TFE/P is 80:20, the pressure is increased to 0.5MPa, the reaction kettle stirrer is started, then the temperature is increased to 70 ℃, the mixed monomer of TFE/P is 80:20 is continuously added, the pressure is increased to 3.0MPa, 10g perfluoro bromoethyl vinyl ether of a vulcanization point monomer is added through a metering pump, a redox initiator is mixed with 2.5g ammonium persulfate and 2.5g potassium persulfate, 2.5g sodium metabisulfite and 5g I (CF) of a chain transfer agent2CF2)2When the polymerization reaction starts and the pressure of the reaction kettle is reduced by 0.01MPa, the TFE/P mixed monomer is supplemented into the reaction kettle, and the pressure in the reaction kettle is maintained to be 3.0 MPa.
The reaction was stopped when 1500g of TFE/P was continuously fed. And (3) obtaining the tetrafluoroethylene-propylene rubber emulsion, coagulating the tetrafluoroethylene-propylene rubber emulsion by using a magnesium chloride aqueous solution, washing the tetrafluoroethylene-propylene rubber emulsion by using deionized water, and continuously drying the tetrafluoroethylene-propylene rubber emulsion for 14 hours in a vacuum drying oven at the temperature of 90 ℃ and the pressure of-0.09 MPa to obtain a rubber product.
Examples 4 to 8
Compared with the examples 1-3, the reaction steps are the same, and only the reaction conditions are adjusted, and the specific steps are as follows:
comparative example 1
The difference compared with example 1 is that perfluorobromoethyl vinyl ether, a vulcanization point monomer, is not added during the polymerization.
Comparative example 2
The difference compared to example 1 is that the chain transfer agent is 5g of methanol.
Comparative example 3
Compared with the example 1, the difference is that the polymerization process does not add the sulfuration point monomer perfluorobromoethyl vinyl ether, does not adopt iodoalkane as a chain transfer agent, and adopts 5g of methanol as a chain transfer agent.
Examples of the experiments
The performances of examples 1 to 8 and comparative examples 1 to 3 obtained by the method of the present application were examined, and the results were:
although the invention has been described in detail hereinabove by way of general description, specific embodiments and experiments, it will be apparent to those skilled in the art that many modifications and improvements can be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.
Claims (11)
1. A synthetic method of tetrafluoroethylene-propylene rubber is characterized in that tetrafluoroethylene and propylene monomers are used as raw materials, in the process of preparing the tetrafluoroethylene-propylene rubber by an emulsion polymerization method, olefin containing bromine or iodine in a vulcanization point monomer is added, and I (CF) is selected2)nI is a chain transfer agent, wherein n is an integer of 2-6;
the alkene containing bromine or iodine is one or more of perfluoro-4-bromo-1-butene, perfluoro bromoethyl vinyl ether, perfluoro iodoethyl vinyl ether, perfluoro-4-iodo-1-butene, trifluoro iodoethylene or trifluoro bromoethylene.
2. The method of claim 1, wherein a redox initiator is used in the reaction, the redox initiator is a mixture of potassium persulfate and ammonium persulfate, and the reduction initiator is sodium metabisulfite.
3. The method according to claim 1, wherein the amount ratio of the tetrafluoroethylene to the propylene is 40:60 to 80: 20.
4. A process according to any one of claims 1 to 3, wherein the amount of said cure site monomer added is from 0.1 to 3% by mass of the tetrafluoroethylene and propylene monomers.
5. The method of claim 2, comprising the steps of:
adding deionized water, a pH buffering agent and an emulsifier into a reaction kettle, vacuumizing the reaction kettle, adding the tetrafluoroethylene and propylene monomers into the reaction kettle until the pressure in the reaction kettle is 0.5-3.0 MPa, heating the reaction kettle to 60-100 ℃, adding the vulcanization point monomer and the chain transfer agent into the reaction kettle, adding the redox initiator to initiate polymerization, and supplementing and adding the tetrafluoroethylene and propylene monomers in the reaction process to maintain the pressure in the reaction kettle at the initial pressure to finish the reaction.
6. The method according to claim 5, wherein in the redox initiation system, the mass ratio of potassium persulfate to ammonium persulfate is 1-5: 1, and the mass sum ratio of the sodium metabisulfite to the potassium persulfate to the ammonium persulfate is 1:1 to 3.
7. The method according to claim 6, wherein the redox initiator is added in an amount of 0.1 to 1% by mass based on the mass of the monomer to be polymerized.
8. A method according to any one of claims 5 to 7, wherein the chain transfer agent is added in an amount of 0.1 to 2% by mass based on the mass of the monomers to be polymerized.
9. A process according to any one of claims 5 to 7, wherein the emulsifier is a perfluoropolyether peroxide.
10. The method of claim 2, comprising the steps of:
adding deionized water, a pH buffering agent and an emulsifying agent into a reaction kettle, vacuumizing the reaction kettle, and adding a mixture of a raw material and a water-soluble organic solvent in a molar ratio of 70:30 of tetrafluoroethylene and propylene monomers, heating the reaction kettle to 85-95 ℃ until the pressure in the reaction kettle is 0.8-1.2 MPa, adding 1.0-1.5% of the mass of the polymerization monomers of a vulcanization point monomer perfluoroiodoethyl vinyl ether and 1.0-1.2% of the mass of the polymerization monomers of a chain transfer agent perfluorobutyl diiodo into the reaction kettle, adding a redox initiator potassium persulfate, ammonium persulfate and sodium metabisulfite, wherein the addition amount of the redox initiator is 0.4-0.6% of the mass of the polymerization monomers, the mass ratio of the potassium persulfate to the ammonium persulfate is 1:1, the mass sum ratio of the sodium metabisulfite to the potassium persulfate to the ammonium persulfate is 1:2, initiating a polymerization reaction, and supplementing the tetrafluoroethylene and propylene monomers in the reaction process to maintain the pressure in the reaction kettle at an initial pressure, thus completing the reaction.
11. Tetrapropylene fluoride rubber obtainable by a process according to any one of claims 1 to 10.
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| US4943622A (en) * | 1987-06-04 | 1990-07-24 | Nippon Mektron, Limited | Process for producing peroxide-vulcanizable, fluorine-containing elastomer |
| CN1431248A (en) * | 1996-11-29 | 2003-07-23 | 日本梅克特隆株式会社 | Fluorine contg. elastomer compsns. |
| CN103342772A (en) * | 2013-07-12 | 2013-10-09 | 中昊晨光化工研究院有限公司 | Preparation method of fluorinated elastomer capable of being vulcanized by using peroxide |
| CN106317290A (en) * | 2015-07-08 | 2017-01-11 | 中昊晨光化工研究院有限公司 | Perfluoroether elastomer and preparation method thereof |
| CN107814863A (en) * | 2017-10-19 | 2018-03-20 | 浙江巨圣氟化学有限公司 | A kind of preparation method of low temperature resistant fluorine-containing rubber |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4943622A (en) * | 1987-06-04 | 1990-07-24 | Nippon Mektron, Limited | Process for producing peroxide-vulcanizable, fluorine-containing elastomer |
| CN1431248A (en) * | 1996-11-29 | 2003-07-23 | 日本梅克特隆株式会社 | Fluorine contg. elastomer compsns. |
| CN103342772A (en) * | 2013-07-12 | 2013-10-09 | 中昊晨光化工研究院有限公司 | Preparation method of fluorinated elastomer capable of being vulcanized by using peroxide |
| CN106317290A (en) * | 2015-07-08 | 2017-01-11 | 中昊晨光化工研究院有限公司 | Perfluoroether elastomer and preparation method thereof |
| CN107814863A (en) * | 2017-10-19 | 2018-03-20 | 浙江巨圣氟化学有限公司 | A kind of preparation method of low temperature resistant fluorine-containing rubber |
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