CN106854253A - A kind of new low temperature resistant fluorubber and preparation method thereof - Google Patents
A kind of new low temperature resistant fluorubber and preparation method thereof Download PDFInfo
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- CN106854253A CN106854253A CN201510906151.8A CN201510906151A CN106854253A CN 106854253 A CN106854253 A CN 106854253A CN 201510906151 A CN201510906151 A CN 201510906151A CN 106854253 A CN106854253 A CN 106854253A
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- low temperature
- fluorubber
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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
- C08F214/22—Vinylidene fluoride
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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
- C08F2/26—Emulsion polymerisation with the aid of emulsifying agents anionic
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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
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
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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
- C08F214/22—Vinylidene fluoride
- C08F214/225—Vinylidene fluoride with non-fluorinated comonomers
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- Chemical Kinetics & Catalysis (AREA)
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- Polymers & Plastics (AREA)
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Abstract
The present invention relates to a kind of low temperature resistant fluorubber and preparation method thereof.It, with vinylidene, tetrafluoroethene, perfluoropropene as comonomer, is chain-transferring agent with alkane containing iodine with brominated/iodine alkene as cure site monomer that the low temperature resistant fluorubber is, is prepared by discontinuous emulsion polymerization.The fluorubber obtained using synthetic method of the present invention, as little as -25~-23 DEG C of its Tg, black brittleness temperature is less than -35 DEG C, can be vulcanized using peroxide vulcanizing system.
Description
Technical field
The present invention relates to new low temperature resistant fluorubber of one kind and preparation method thereof, belong to fluorination work skill
Art field.
Background technology
Fluoroelastomer is used extensively because of its excellent heat resistance, oil resistivity and chemical-resistant
In encapsulant, container and flexible pipe.International corporation, Su Wei, Du Pont, great Jin etc. are
There are low temperature resistant, the solvent resistant fluorubber of various low temperature domain requirements.Domestic also existing -20 DEG C resistance to
Low temperature fluorubber, -30 DEG C of low temperature fluorubber are developed.But do not see -25 DEG C of rank low-temperature types
Fluorubber relevant report.
Additionally, the synthetic method of low temperature fluorubber is still present some defects at present:Patent
201110451869.4 provide a kind of method for preparing low temperature fluoroelastomer, using perfluor
Methyl vinyl ether and vinylidene, tetrafluoroethene copolymerization, gained fluorubber Tg can be as little as
- 30 DEG C, but adding largely needs to add a large amount of perfluoro methyl vinyl ether (30mol%
Left and right);Patent CN201110180978.7 provides a kind of producer of low temperature resistant fluorubber
Method, copolymerization is carried out using 2~8% perfluoro methyl vinyl ethers and vinylidene, perfluoropropene,
Gained fluorubber Tg is -20 DEG C~-24 DEG C or so.Though have very much in terms of fluorubber Tg is reduced
Effect, but price is costly.Foreign countries are also had been reported that using ethene and vinylidene, perfluor
Propylene carries out copolymerization and can reduce fluorubber Tg to -24 DEG C, but course of reaction is whard to control.
The content of the invention
The present invention provides a kind of low temperature resistant fluorubber and preparation method thereof, and gained rubber Tg is
- 25 DEG C or so, possesses low temperature resistant, solvent-proof advantage.
To achieve these goals, the present invention is adopted the following technical scheme that:
A kind of low temperature resistant fluorubber, is with vinylidene, tetrafluoroethene, perfluoropropene as copolymerization
Monomer, is chain-transferring agent with alkane containing iodine with brominated/iodine alkene as cure site monomer, is passed through
What discontinuous emulsion polymerization was prepared.
In low temperature resistant fluorubber of the present invention, the vinylidene (VDF), tetrafluoroethene
(TFE), perfluoropropene (HFP) mol ratio is:75~85:0~10:15~25;It is preferred that
75~85:0~8:15~20.
In low temperature resistant fluorubber of the present invention, the cure site monomer is fluorubber gross mass
0.01~3.0%.
In low temperature resistant fluorubber of the present invention, the cure site monomer be selected from bromine ethene, 1,1 ,-
Two fluoro- 2- bromines ethene, bromomethyl vinyl ethers, iodoethylene, the iodo- 3,3,4,4- tetrafluoros butylene of 4-,
One or two in 1,1- bis- fluoro- 2- iodoethylenes, trifluoro iodoethylene, bromotrifluoroethylene, preferably
The iodo- 3,3,4,4- tetrafluoros butylene of trifluoro iodoethylene, 4-.
In low temperature resistant fluorubber of the present invention, the chain-transferring agent is fluorubber gross mass
0.02~1.5%.
In low temperature resistant fluorubber of the present invention, the chain-transferring agent be selected from 1,2- ethylidene periodides,
One or more in iodoform, iodomethane, iodoethane 1,3- diiodo propanes.
The present invention is matched by adjusting comonomer, makes it in specific proportioning compatibility, so as to have
Effect control Tg;It is cure site monomer to use brominated/iodine alkene simultaneously, is conducive to further reduction
The Tg of fluorubber, and for the peroxide vulcanizing system vulcanization of finished product provides vulcanization crosslinking point.
It is chain-transferring agent to use special alkane iodide, and the control for being conducive to molecular weight is simultaneously product
Peroxide systems vulcanization provide crosslinking points.With fluorubber obtained in formula of the present invention
With low temperature resistant, solvent-proof advantage.
The present invention also provides the preparation method of above-mentioned low temperature resistant fluorubber, comprises the following steps:
(1) deionized water, pH buffer, emulsifying agent are added in a kettle.;Nitrogen adds
Pressure, after evacuating degassing, to addition vinylidene, tetrafluoroethene, perfluoropropene in reactor
Mix monomer;
(2) in 0.3~5.0MPa of pressure, initiator is added under the conditions of 50~120 DEG C of temperature,
Initiated polymerization;At any time to mix monomer is added in reactor in course of reaction, to maintain
Pressure in kettle;
(3) after polymerisation starts, to addition cure site monomer and chain-transferring agent in reactor
RIX;When reacting dose is accumulated to aimed quality, stop reaction, reclaim unreacted and completely mix
Monomer, while being condensed with magnesium chloride solution, obtains elastomeric solid;
Wherein, R is 1~6 alkyl, X=1~3.
In the preparation method of low temperature resistant fluorubber of the present invention, in step (1), the pH
Buffer is the pH buffers commonly used in the art such as dipotassium hydrogen phosphate.
In the preparation method of low temperature resistant fluorubber of the present invention, in step (1), the breast
Agent is by sodium octyl, PFPE carboxylic acid ammonium with mass ratio 1:3~3:1 prepares and obtains.
It is described to draw in step (2) in the preparation method of low temperature resistant fluorubber of the present invention
Hair agent is 15% (wt) ammonium persulfate aqueous solution.
In the preparation method of low temperature resistant fluorubber of the present invention, in step (2), reaction pressure
Power is preferably 1.5~2.5MPa, and temperature is 80~100 DEG C.Suitable reaction pressure is conducive to reaction
Carry out, and it is less demanding to reactor material.And suitable reaction temperature both ensures initiator
Activity, it is ensured that reaction is normally carried out, while decomposition of initiator excessive velocities are avoided, effectively control
Reaction speed.
The synthetic method of low temperature resistant fluorubber of the present invention need not add a large amount of perfluoro-methyl second
Alkene ether, with low cost, reaction condition temperature is controllable;Using synthesis side of the present invention
As little as -25~-23 DEG C of method gained fluorubber Tg, black brittleness temperature is less than -35 DEG C, can use
Peroxide vulcanizing system is vulcanized.
Specific embodiment
Following examples are used to illustrate the present invention, but are not limited to the scope of the present invention.If
Do not specialize, reagent used is conventional commercial reagent in embodiment, institute in embodiment
The conventional meanses that technological means is well known to those skilled in the art.
The performance test methods of fluoroelastomer are as follows:
121 DEG C of tests of rubber Mooney ML (1+10) are according to ASTM D1646.
Wherein, sulfurizing formula is:
232 DEG C × 4h of one section vulcanization 168 DEG C × 10min post vulcanizations.
Tensile strength method of testing is according to ASTM D412.
Permanent compression set method of testing is according to ASTM D1414.
Black brittleness temperature testing method is according to ASTM D 2137-2005
Medium-resistance method of testing is according to ASTM D471-1998
Embodiment 1
The present embodiment provides a kind of preparation method of low temperature fluorubber, comprises the following steps:
(1) in the 5L stainless steel cauldrons with agitator, 3L deionized waters are added,
2g dipotassium hydrogen phosphates, 2g emulsifying agents (PFPE peroxide and sodium octyl 3:1 mixes
Compound), after repeating nitrogen pressurization, evacuation degassing, added in reactor with compressor
The mix monomer of VDF/HFP=85/15 (mol ratio);
(2) 1.5MPa is boosted at 80 DEG C, 15% (wt) of 20g is pumped into by metering
Ammonium persulfate aqueous solution, initiated polymerization;At any time to being added in reactor in course of reaction
The mix monomer of VDF/HFP=85/15 (mol ratio), to maintain pressure in kettle;
(3) after polymerisation starts, in reactor add trifluoro iodoethylene 40g and
ICH2CH2I 5g, reaction continues 6h, fluorubber emulsion 4.5kg or so is obtained, using chlorination
The magnesium aqueous solution is condensed, washs, continuing drying out 16h in air blower electrical heating baking oven, obtains
Obtain low temperature fluorubber product 1.4kg.
Properties of product are as shown in table 1.
The low temperature resistant fluorubber properties of product table of table 1
Embodiment 2
The present embodiment provides a kind of preparation method of low temperature fluorubber, comprises the following steps:
(1) in the 5L stainless steel cauldrons with agitator, 3L deionized waters are added,
2g dipotassium hydrogen phosphates, 2g emulsifying agents (PFPE carboxylic acid ammonium and sodium octyl 3:1 mixing
Thing), after repeating nitrogen pressurization, evacuation degassing, added in reactor with compressor
The mix monomer of VDF/TFE/HFP=80/4/16 (mol ratio);
(2) 1.5MPa is boosted at 80 DEG C, 15% (wt) of 20g is pumped into by metering
Ammonium persulfate aqueous solution, initiated polymerization;At any time to being added in reactor in course of reaction
The mix monomer of VDF/TFE/HFP=80/4/16 (mol ratio), to maintain pressure in kettle;
(3) after polymerisation starts, to addition 40g iodoethylenes, ICH in reactor2CH2I
8g, reaction continues 6h, fluorubber emulsion 4.5kg or so is obtained, using magnesium chloride brine
It is condensed, washs, 16h is continued drying out in air blower electrical heating baking oven, obtains low temperature fluorine
Rubber product 1.4kg.
Properties of product are as shown in table 2
The low temperature resistant fluorubber properties of product table of table 2
Embodiment 3
The present embodiment provides a kind of preparation method of low temperature fluorubber, comprises the following steps:
(1) in the 5L stainless steel cauldrons with agitator, 3L deionized waters are added,
2g dipotassium hydrogen phosphates, 2g emulsifying agents (PFPE carboxylic acid ammonium and sodium octyl 3:1 mixing
Thing), after repeating nitrogen pressurization, evacuation degassing, added in reactor with compressor
The mix monomer of VDF/TFE/HFP=75/8/17 (mol ratio);
(2) 1.8MPa is boosted at 80 DEG C, is then pumped into the 15% of 10g by metering
(wt) ammonium persulfate aqueous solution, initiated polymerization;At any time to reactor in course of reaction
In add the mix monomer of VDF/TFE/HFP=75/8/17 (mol ratio), keep reactor
Interior pressure is 1.8MPa;
(3) after polymerisation starts, to the addition tetrafluoro fourths of 20g4- iodo- 3,3,4,4- in reactor
Alkene, ICH2CH2I 6g, reaction continues 8h, obtains fluorubber emulsion 4.5kg or so, uses
Magnesium chloride brine is condensed, washs, continuing drying out 16h in air blower electrical heating baking oven,
Obtain low temperature fluorubber product 1.4kg.
Properties of product are as shown in table 3
The low temperature resistant fluorubber properties of product table of table 3
Performance | Unit | Index |
Mooney | MU | 35 |
Tg | ℃ | -23.2 |
Black brittleness temperature | ℃ | -33 |
Tensile strength | MPa | 21.3 |
Permanent compression set | % (200 DEG C × 70h) | 20 |
Resistance to 3# marks oil | Volume change, % | +2.3 |
M15 | Volume change | +23 |
Embodiment 4
The present embodiment provides a kind of preparation method of low temperature fluorubber, comprises the following steps:
(1) in the 5L stainless steel cauldrons with agitator, 3L deionized waters are added,
2g dipotassium hydrogen phosphates, 2g emulsifying agents (PFPE carboxylic acid ammonium and sodium octyl 3:1 mixing
Thing), after repeating nitrogen pressurization, evacuation degassing, added in reactor with compressor
The mix monomer of VDF/TFE/HFP=75/8/17 (mol ratio);
(2) 1.8MPa is boosted at 80 DEG C, 15% (wt) of 10g is pumped into by metering
Ammonium persulfate aqueous solution, initiated polymerization;At any time to being added in reactor in course of reaction
The mix monomer of VDF/HFP/TFE=75/8/17 (mol ratio), keeps reacting kettle inner pressure
It is 1.8MPa;
(3) after polymerisation starts, to addition 20g iodoethylenes, ICH in reactor2CH2I
4.2g, reaction continues 6.5h, obtains fluorubber emulsion 4.5kg or so, water-soluble using magnesium chloride
Liquid is condensed, washs, 16h is continued drying out in air blower electrical heating baking oven, obtains low temperature
Fluorubber product 1.4kg.
Properties of product are as shown in table 4
The low temperature resistant fluorubber properties of product table of table 4
Performance | Unit | Index |
Mooney | MU | 50 |
Tg | ℃ | -23.5 |
Black brittleness temperature | ℃ | -32 |
Tensile strength | MPa | 20.1 |
Permanent compression set | % (200 DEG C × 70h) | 28 |
Resistance to 3# marks oil | Volume change, % | +1.9 |
M15 | Volume change | +24 |
Embodiment 5
The present embodiment provides a kind of preparation method of low temperature fluorubber, comprises the following steps:
(1) in the 5L stainless steel cauldrons with agitator, 3L deionized waters are added,
2g dipotassium hydrogen phosphates, 2g emulsifying agents (PFPE carboxylic acid sodium and sodium octyl 3:1 mixing
Thing), after repeating nitrogen pressurization, evacuation degassing, added in reactor with compressor
The mix monomer of VDF/HFP=83/17 (mol ratio);
(2) 2.5MPa is boosted at 80 DEG C, 15% (wt) of 10g is pumped into by metering
Ammonium persulfate aqueous solution, initiated polymerization;At any time to being added in reactor in course of reaction
The mix monomer of VDF/HFP=83/17 (mol ratio), holding reacting kettle inner pressure is 2.5MPa;
(3) after polymerisation starts, to the addition tetrafluoro fourths of 20g4- iodo- 3,3,4,4- in reactor
Alkene, iodoform 3.5g, reaction continues 5h, fluorubber emulsion 4.5kg or so is obtained, using chlorine
Change the magnesium aqueous solution be condensed, wash, continuing drying out 16h in air blower electrical heating baking oven,
Obtain low temperature fluorubber product 1.4kg.
Properties of product are as shown in table 5
The low temperature resistant fluorubber properties of product table of table 5
Performance | Unit | Index |
Mooney | MU | 60 |
Tg | ℃ | -24.8 |
Black brittleness temperature | ℃ | -35 |
Tensile strength | MPa | 21.2 |
Permanent compression set | % (200 DEG C × 70h) | 25 |
Resistance to 3# marks oil | Volume change, % | +3.2 |
M15 | Volume change | +46 |
Although above making to the present invention with a general description of the specific embodiments
Description in detail, but on the basis of the present invention, it can be made some modifications or improvements, this
Will be apparent to those skilled in the art.Therefore, without departing from spirit of the invention
On the basis of these modifications or improvements, belong to the scope of protection of present invention.
Claims (10)
1. a kind of low temperature resistant fluorubber, it is characterised in that with vinylidene, tetrafluoroethene,
Perfluoropropene is comonomer, with brominated/iodine alkene as cure site monomer, is with alkane containing iodine
Chain-transferring agent, is prepared by discontinuous emulsion polymerization.
2. low temperature resistant fluorubber according to claim 1, it is characterised in that the inclined fluorine
Ethene, tetrafluoroethene, perfluoropropene mol ratio are:75~85:0~10:15~25.
3. low temperature resistant fluorubber according to claim 2, it is characterised in that it is described partially
PVF, tetrafluoroethene, perfluoropropene mol ratio are 75~85:0~8:15~20.
4. according to any described low temperature resistant fluorubber of claim 1-3, it is characterised in that
The cure site monomer be selected from bromine ethene, 1,1 ,-two fluoro- 2- bromines ethene, bromomethyl vinyl ethers,
The iodo- 3,3,4,4- tetrafluoros butylene of iodoethylene, 4-, the fluoro- 2- iodoethylenes of 1,1- bis-, trifluoro iodoethylene,
One or two in bromotrifluoroethylene;It is preferred that the iodo- 3,3,4,4- tetrafluoros fourth of trifluoro iodoethylene, 4-
Alkene.
5. according to any described low temperature resistant fluorubber of claim 1-3, it is characterised in that
The cure site monomer consumption is the 0.01~3.0% of fluorubber gross mass.
6. according to any described low temperature resistant fluorubber of claim 1-4, it is characterised in that
The chain-transferring agent is the 0.02~1.5% of fluorubber gross mass.
7. according to any described low temperature resistant fluorubber of claim 1-6, it is characterised in that
The chain-transferring agent is selected from 1,2- ethylidene periodides, iodoform, iodomethane, iodoethane 1,3- diiodo-s third
One or more in alkane.
8. the preparation method of any low temperature resistant fluorubber of claim 1-7, it is characterised in that
Comprise the following steps:
(1) deionized water, pH buffer, emulsifying agent are added in a kettle.;Nitrogen adds
Pressure, after evacuating degassing, to addition vinylidene, tetrafluoroethene, perfluoropropene in reactor
Mix monomer;
(2) in 0.3~5.0MPa of pressure, initiator is added under the conditions of 50~120 DEG C of temperature,
Initiated polymerization;At any time to mix monomer is added in reactor in course of reaction, to maintain
Pressure in kettle;
(3) after polymerisation starts, to addition cure site monomer and chain-transferring agent in reactor
RIX;When reacting dose is accumulated to aimed quality, stop reaction, reclaim unreacted and completely mix
Monomer, while being condensed with magnesium chloride solution, obtains elastomeric solid;
Wherein, R is 1~6 alkyl, X=1~3.
9. preparation method according to claim 8, it is characterised in that in step (1),
The emulsifying agent is by sodium octyl, PFPE carboxylic acid ammonium with mass ratio 1:3~3:1 prepare and
.
10. preparation method according to claim 8, it is characterised in that in step (2),
Reaction pressure is 1.5~2.5MPa, and temperature is 80~100 DEG C.
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
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CN110903428A (en) * | 2018-09-17 | 2020-03-24 | 中昊晨光化工研究院有限公司 | Low-temperature-resistant fluoroether rubber and preparation method and application thereof |
CN111363076A (en) * | 2020-04-24 | 2020-07-03 | 四川道弘科技有限公司 | Ternary peroxide fluororubber and preparation method thereof, and intelligent wearing material and preparation method thereof |
CN111875732A (en) * | 2020-08-18 | 2020-11-03 | 山东非金属材料研究所 | Low-temperature-resistant fluororubber and preparation method thereof |
CN115340623A (en) * | 2022-08-15 | 2022-11-15 | 万华化学集团股份有限公司 | Method for preparing polyvinylidene fluoride resin |
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CN104448095A (en) * | 2014-12-15 | 2015-03-25 | 中昊晨光化工研究院有限公司 | Preparation method of fluororubber capable of being vulcanized by peroxide |
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
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CN110903428A (en) * | 2018-09-17 | 2020-03-24 | 中昊晨光化工研究院有限公司 | Low-temperature-resistant fluoroether rubber and preparation method and application thereof |
CN110903428B (en) * | 2018-09-17 | 2021-10-22 | 中昊晨光化工研究院有限公司 | Low-temperature-resistant fluoroether rubber and preparation method and application thereof |
CN111363076A (en) * | 2020-04-24 | 2020-07-03 | 四川道弘科技有限公司 | Ternary peroxide fluororubber and preparation method thereof, and intelligent wearing material and preparation method thereof |
CN111875732A (en) * | 2020-08-18 | 2020-11-03 | 山东非金属材料研究所 | Low-temperature-resistant fluororubber and preparation method thereof |
CN115340623A (en) * | 2022-08-15 | 2022-11-15 | 万华化学集团股份有限公司 | Method for preparing polyvinylidene fluoride resin |
CN115340623B (en) * | 2022-08-15 | 2023-12-19 | 万华化学集团股份有限公司 | Method for preparing polyvinylidene fluoride resin |
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