CN107417853A - A kind of preparation method of porous polypropylene nitrile - Google Patents
A kind of preparation method of porous polypropylene nitrile Download PDFInfo
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- CN107417853A CN107417853A CN201710826918.5A CN201710826918A CN107417853A CN 107417853 A CN107417853 A CN 107417853A CN 201710826918 A CN201710826918 A CN 201710826918A CN 107417853 A CN107417853 A CN 107417853A
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- porous polypropylene
- oil phase
- polypropylene nitrile
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- -1 polypropylene Polymers 0.000 title claims abstract description 18
- 239000004743 Polypropylene Substances 0.000 title claims abstract description 16
- 150000002825 nitriles Chemical class 0.000 title claims abstract description 16
- 229920001155 polypropylene Polymers 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 239000012071 phase Substances 0.000 claims abstract description 16
- 239000008346 aqueous phase Substances 0.000 claims abstract description 14
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims abstract description 12
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims abstract description 12
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 7
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims abstract description 7
- 238000005286 illumination Methods 0.000 claims abstract description 6
- 239000011148 porous material Substances 0.000 claims abstract description 5
- 238000012805 post-processing Methods 0.000 claims abstract description 3
- 238000003756 stirring Methods 0.000 claims abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000003431 cross linking reagent Substances 0.000 claims abstract 5
- 239000008367 deionised water Substances 0.000 claims abstract 2
- 229910021641 deionized water Inorganic materials 0.000 claims abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 claims description 17
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 2
- 238000012546 transfer Methods 0.000 claims description 2
- 239000007870 radical polymerization initiator Substances 0.000 claims 4
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical group C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 1
- ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000003505 polymerization initiator Substances 0.000 claims 1
- 229930192474 thiophene Natural products 0.000 claims 1
- 238000001291 vacuum drying Methods 0.000 claims 1
- 239000003999 initiator Substances 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 101710141544 Allatotropin-related peptide Proteins 0.000 description 11
- 238000010526 radical polymerization reaction Methods 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000003643 water by type Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 239000003863 metallic catalyst Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- QJMWBGFDDXANCP-UHFFFAOYSA-L bis(2,6-ditert-butylphenoxy)-methylalumane Chemical compound [Al+2]C.CC(C)(C)C1=CC=CC(C(C)(C)C)=C1[O-].CC(C)(C)C1=CC=CC(C(C)(C)C)=C1[O-] QJMWBGFDDXANCP-UHFFFAOYSA-L 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- WIWBLJMBLGWSIN-UHFFFAOYSA-L dichlorotris(triphenylphosphine)ruthenium(ii) Chemical compound [Cl-].[Cl-].[Ru+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 WIWBLJMBLGWSIN-UHFFFAOYSA-L 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/42—Nitriles
- C08F220/44—Acrylonitrile
-
- 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
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/26—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof by elimination of a solid phase from a macromolecular composition or article, e.g. leaching out
-
- 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
- C08F2438/00—Living radical polymerisation
- C08F2438/01—Atom Transfer Radical Polymerization [ATRP] or reverse ATRP
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2201/00—Foams characterised by the foaming process
- C08J2201/04—Foams characterised by the foaming process characterised by the elimination of a liquid or solid component, e.g. precipitation, leaching out, evaporation
- C08J2201/046—Elimination of a polymeric phase
- C08J2201/0462—Elimination of a polymeric phase using organic solvents
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention provides a kind of preparation method of porous polypropylene nitrile.The step of this method is：（1）The preparation of aqueous phase：Polyvinylpyrrolidone, deionized water are mixed, obtain clear solution；（2）The preparation of oil phase：Acrylonitrile, crosslinking agent, organic light trigger, atom transferred free radical initiator are mixed, obtain oil phase；（3）The aqueous phase of gained is added slowly in oil phase under stirring, illumination polymerize at room temperature after being added dropwise, and by post processing, porous polypropylene nitrile is made.The present invention using light irradiation polymerize, have it is simple to operate, cost is cheap, and obtained porous polypropylene nitrile uniform pore diameter, there is larger specific surface area.
Description
Technical field
The invention belongs to synthesis of polymer material field, specifically a kind of preparation method of porous polypropylene nitrile.
Background technology：
Porous material is widely used in the neck such as seperation film, adsorbent, gas storing media, catalyst carrier and tissue engineering bracket
Domain.Hole size and distribution, porosity, the surface chemistry of hole wall and pore structure determine the property and work(of porous material
Can, the simple method for efficiently preparing regular ordered porous structural of development is all the emphasis of research all the time.
ATRP（Atom transfer radical polymerization, ATRP）It is 90 years
A kind of activity polymerizating technology that generation grows up, there is significant application value.Nineteen ninety-five, the king of Univ Carnegie Mellon of the U.S.
Bright and beautiful mountain doctor, KMatyjaszewski professors [Controlled/living radical polymerization. atom
transfer radical polymerization in the presence of transition-metal
Complexes, J Am Chem Soc, 1995,117,5614-5615.] and the pool of Kyoto Univ Japan this light south professor
[Polymerization of methyl methacrylate with the carbon tetrachloride/
dichlorotris (triphenylphosphine)ruthenium(II)/ Methylaluminum Bis (2, 6-di-
tert-butylphenoxide) initiating system: possibility of living radical
polymerization. Macromolecules,1995,28:1721-1723] independently report it is transition metal-catalyzed
Active free radical polymerization.ATRP polymerization opens a new way to carry out Polymer supported catalyst, and wide with polymerized monomer
General, reaction condition is gentle, reaction not by the impurity effects such as water, polymer molecule Mass Distribution is narrow the advantages that, it can be said that
The research of ATRP polymerization techniques will be one of most promising research topic of several years inner macromolecule synthesis chemical field from now on.
ATRP is a more complicated system, including polymerized monomer, transferable halogen atom draw
Hair agent, the transition-metal catalyst and its part for having multiple valence states.And reduce the dosage of metallic catalyst in ATRP systems always
It is one of target that researcher pursues, it is convenient that the reduction of amount of metal catalyst can be brought to the post processing of product.
Photo-polymerization process refers to, in visible ray, ultraviolet light or in the presence of high-energy ray, in the effect of light trigger draw
Bill body carries out the process that polymerisation prepares polymer.Photopolymerization reaction process has many advantages, such as：Environmentally friendly, pollution
Less, polymerization speed is fast, polymerizate excellent performance, energy-conservation.Photopolymerization is combined with ATRP, can be with
Overcome some shortcomings of ATRP.
The content of the invention
The technical problem to be solved in the invention is：1st, ATRP temperature is high；2nd, atom transfer is free
Base polymerize；3rd, the limitation that ATRP is difficult to remove using metallic catalyst, there is provided one kind is without metal catalytic
Photoinduction atom transferred free radical polymerization system.
The present invention relates to a kind of preparation method of porous polypropylene nitrile, it is characterised in that the non-metal catalyst of photoinduction is deposited
Atom transition free radical polymerization reaction prepare porous polypropylene nitrile.
, can be without using other heaters due to the atom transition free radical polymerization reaction using photoinduction.
The invention has the characteristics that：（1）Overcome traditional ATRP using metallic catalyst and
It is difficult to the deficiency removed completely.（2）The polymerisation can be carried out at room temperature, and reaction condition is gentle.（3）Turn with conventional atom
Move radical polymerization technique to compare, technique is simpler.
Specific embodiment：
Embodiment 1：
Take 0.5g polyvinylpyrrolidones, 100mL deionized waters mixing, until formed polyvinylpyrrolidone be dissolved into it is transparent molten
Liquid, obtain aqueous phase.By 5.0mL acrylonitrile, 0.2g N, N'- methylene-bisacrylamides, 24.3mg α-bromo-acid ethyl ester,
1mg is mixed to get oil phase.The aqueous phase of gained is added slowly in oil phase, stirred, after being added dropwise under light illumination
24h, filtering, is extracted to obtain porous polypropylene nitrile with absolute methanol.
Embodiment 2：
Take 0.5g polyvinylpyrrolidones, 100mL deionized waters mixing, until formed polyvinylpyrrolidone be dissolved into it is transparent molten
Liquid, obtain aqueous phase.By 5.0mL acrylonitrile, 0.2g N, N'- methylene-bisacrylamides, 18.1mg2- ethyl bromides, 1mg
It is mixed to get oil phase.The aqueous phase of gained is added slowly in oil phase, stirred, 24h under light illumination after being added dropwise,
Filtering, is extracted to obtain porous polypropylene nitrile with absolute methanol.
Embodiment 3：
Take 0.5g polyvinylpyrrolidones, 100mL deionized waters mixing, until formed polyvinylpyrrolidone be dissolved into it is transparent molten
Liquid, obtain aqueous phase.By 5.0mL acrylonitrile, 0.2g N, N'- methylene-bisacrylamides, 18.1mg2- ethyl bromides,
0.8mg phenthazine is mixed to get oil phase.The aqueous phase of gained is added slowly in oil phase, stirred, in light after being added dropwise
The lower 24h of irradiation, filtering, is extracted to obtain porous polypropylene nitrile with absolute methanol.
Embodiment 4：
Take 0.5g polyvinylpyrrolidones, 100mL deionized waters mixing, until formed polyvinylpyrrolidone be dissolved into it is transparent molten
Liquid, obtain aqueous phase.By 5.0mL acrylonitrile, 0.2g N, N'- methylene-bisacrylamides, 18.1mg2- ethyl bromides,
0.5mg3,4,9,10- tetra-（12- alkoxy carbonyl groups）It is mixed to get oil phase.The aqueous phase of gained is added slowly in oil phase, stirred
Mix, 24h under light illumination after being added dropwise, filtering, extracted to obtain porous polypropylene nitrile with absolute methanol.
Embodiment 5：
Take 0.5g polyvinylpyrrolidones, 100mL deionized waters mixing, until formed polyvinylpyrrolidone be dissolved into it is transparent molten
Liquid, obtain aqueous phase.By 5.0mL acrylonitrile, 0.2g N, N'- methylene-bisacrylamides, 18.1mg2- ethyl bromides,
0.1mg5,10- diphenyl -5,10- dihydro phenthazine is mixed to get oil phase.The aqueous phase of gained is added slowly in oil phase,
Stirring, 24h under light illumination being added dropwise after, filter, extracted to obtain porous polypropylene nitrile with absolute methanol.
Claims (6)
- A kind of 1. preparation method of porous polypropylene nitrile；It is characterized in that：（1）The preparation of aqueous phase：Polyvinylpyrrolidone, deionized water are mixed, obtain clear solution；（2）The preparation of oil phase：By acrylonitrile, crosslinking agent, organic light trigger, atom transfer radical polymerization initiator, obtain Oil phase；（3）The aqueous phase of gained is added slowly in oil phase under stirring, after being added dropwise, letting nitrogen in and deoxidizing, room temperature Lower illumination, carry out polymerisation；After reaction terminates, by post processing, uniform pore diameter, porous poly- the third of large specific surface area is made Alkene nitrile.
- 2. organic light trigger according to claim 1, it is characterised in that described organic light trigger is, 3,4,9, 10- tetra-（12- alkoxy carbonyl groups）, phenthazine, 5,10- diphenyl -5,10- dihydros phenthazine, the bromo- N- methyl fen thiophenes of 3,7- bis- Piperazine.
- 3. atom transfer radical polymerization initiator according to claim 1, it is characterised in that described atom transfer is certainly It is α-bromo-acid ethyl ester, 2 bromopropionic acid ethyl ester by base polymerization initiator.
- 4. crosslinking agent according to claim 1, it is characterised in that described crosslinking agent is divinylbenzene, N, N'- methylenes Base bisacrylamide.
- 5. acrylonitrile according to claim 1, atom transfer radical polymerization initiator, organic light trigger, its feature It is that described acrylonitrile, atom transfer radical polymerization initiator, the mol ratio of organic light trigger are（50-2000）： （1）：（0.001-0.1）；The addition of crosslinking agent is acrylonitrile mass number（1-10%）.
- 6. the method according to claim 1 for preparing porous polypropylene nitrile, it is characterised in that the porous polypropylene nitrile of gained Extracted 24 hours with absolute methanol, dried in vacuum drying chamber.
Priority Applications (1)
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| CN201710826918.5A CN107417853A (en) | 2017-09-14 | 2017-09-14 | A kind of preparation method of porous polypropylene nitrile |
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| CN201710826918.5A CN107417853A (en) | 2017-09-14 | 2017-09-14 | A kind of preparation method of porous polypropylene nitrile |
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Family
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113346080A (en) * | 2021-05-24 | 2021-09-03 | 上海交通大学 | Sulfur-containing positive electrode material for secondary battery, preparation method of sulfur-containing positive electrode material and secondary battery |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113346080A (en) * | 2021-05-24 | 2021-09-03 | 上海交通大学 | Sulfur-containing positive electrode material for secondary battery, preparation method of sulfur-containing positive electrode material and secondary battery |
| CN113346080B (en) * | 2021-05-24 | 2023-01-24 | 上海交通大学 | Sulfur-containing positive electrode material for secondary battery, preparation method of sulfur-containing positive electrode material and secondary battery |
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