CN107286272A - A kind of method of macromolecular grafted polymerization - Google Patents
A kind of method of macromolecular grafted polymerization Download PDFInfo
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- CN107286272A CN107286272A CN201710624953.9A CN201710624953A CN107286272A CN 107286272 A CN107286272 A CN 107286272A CN 201710624953 A CN201710624953 A CN 201710624953A CN 107286272 A CN107286272 A CN 107286272A
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- macromolecule
- free radical
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- 238000000034 method Methods 0.000 title claims abstract description 32
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 8
- 150000003254 radicals Chemical class 0.000 claims abstract description 34
- 229920002521 macromolecule Polymers 0.000 claims abstract description 31
- 239000000178 monomer Substances 0.000 claims abstract description 23
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 15
- 229920000642 polymer Polymers 0.000 claims abstract description 14
- 239000003999 initiator Substances 0.000 claims abstract description 10
- 239000003504 photosensitizing agent Substances 0.000 claims abstract description 5
- 239000007787 solid Substances 0.000 claims abstract description 4
- 230000002186 photoactivation Effects 0.000 claims abstract description 3
- 230000001235 sensitizing effect Effects 0.000 abstract description 13
- 229920001519 homopolymer Polymers 0.000 abstract description 10
- 230000000977 initiatory effect Effects 0.000 abstract description 8
- 238000010438 heat treatment Methods 0.000 abstract description 5
- 238000005406 washing Methods 0.000 abstract description 4
- 230000003321 amplification Effects 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 238000003199 nucleic acid amplification method Methods 0.000 abstract description 3
- 230000008569 process Effects 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000002033 PVDF binder Substances 0.000 description 6
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 6
- QAIPRVGONGVQAS-DUXPYHPUSA-N trans-caffeic acid Chemical compound OC(=O)\C=C\C1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-DUXPYHPUSA-N 0.000 description 6
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000006392 deoxygenation reaction Methods 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- ACEAELOMUCBPJP-UHFFFAOYSA-N (E)-3,4,5-trihydroxycinnamic acid Natural products OC(=O)C=CC1=CC(O)=C(O)C(O)=C1 ACEAELOMUCBPJP-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 229940074360 caffeic acid Drugs 0.000 description 3
- 235000004883 caffeic acid Nutrition 0.000 description 3
- QAIPRVGONGVQAS-UHFFFAOYSA-N cis-caffeic acid Natural products OC(=O)C=CC1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-UHFFFAOYSA-N 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 238000005286 illumination Methods 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 235000015511 Liquidambar orientalis Nutrition 0.000 description 2
- 239000004870 Styrax Substances 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920000578 graft copolymer Polymers 0.000 description 2
- 238000010559 graft polymerization reaction Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- -1 polypropylene Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 241000736148 Styrax Species 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000005260 alpha ray Effects 0.000 description 1
- 150000008365 aromatic ketones Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000005251 gamma ray Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000006897 homolysis reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000005217 methyl ethers Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000007342 radical addition reaction Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000009738 saturating Methods 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
- 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
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- 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
- C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
- C08F255/02—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having two or three carbon atoms
-
- 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
- C08F259/00—Macromolecular compounds obtained by polymerising monomers on to polymers of halogen containing monomers as defined in group C08F14/00
- C08F259/08—Macromolecular compounds obtained by polymerising monomers on to polymers of halogen containing monomers as defined in group C08F14/00 on to polymers containing fluorine
Abstract
The invention belongs to technical field of function materials, a kind of method of macromolecular grafted polymerization is disclosed, it is characterised in that：Macromolecule is put into photosensitizing agent solution first and carries out ultraviolet light irradiation, macromolecule is occurred photoactivation, polymeric initiator is generated；Then, add monomer and heat, polymeric initiator is decomposed generation high molecular free radical and semipinacol free radical, high molecular free radical is graft-polymerized with monomer again, obtains modified high-molecular.Described macromolecule is Polymer Solution or solid.This method can reduce homopolymer generation, be conducive to improving grafting rate, second step heating removes unnecessary sensitising agent without washing before triggering, simple to operate, and larger liquor capacity can be used during heating initiation grafting, and macromolecule treating capacity is big, and process is easy to amplification.During using Polymer Solution, macromolecule and sensitising agent and the abundant haptoreaction of monomer can be made, be conducive to improving grafting rate.
Description
The invention belongs to technical field of function materials.
Background technology
By being modified to macromolecule, thus it is possible to vary high molecular hydrophilic and hydrophobic, mechanical property, chemical property, biology
Compatibility etc..Macromolecule modified method mainly has blending method, graft polymerization method etc..Graft polymerization method refers to utilize chemistry, thing
Reason means form activated centre on macromolecule, then trigger monomer to be graft-polymerized on macromolecule by activated centre.Grafting is poly-
It is legal to radiate initiation grafting, light-initiated grafting etc. including high-energy ray.
High-energy ray radiation initiation grafting is to utilize high-energy ray (such as X-ray, gamma-rays, alpha ray) on macromolecule
Free radical activated centre and then initiation grafting are produced, can be reacted at normal temperatures, is post-processed fairly simple.Energy of γ ray is high, wears
Saturating power is strong, and reaction is uniform, is usually used in the more stable polymer modification of the chemical property such as PTFE, PVDF, but this method needs are high
Expensive irradiation apparatus and harsh experiment condition, are unfavorable for commercial Application.
Light-initiated grafting is to trigger monomer to polymerize with macromolecular grafted using ultraviolet light irradiation.It is light-initiated grafting mostly according to
Radical addition polymerization mechanism is carried out, it is necessary first to is generated high molecular free radical, can be divided according to the difference of free radical producing method
For containing three kinds of triggering mechanisms such as photosensitive based polyalcohol irradiation decomposition method, free radical chain transfer method and hydrogen abstraction reaction methods.(1) containing photosensitive
Based polyalcohol irradiates decomposition method.When some polymer containing optical active group are by ultraviolet light, it may occur that NorrishI types
Reaction.For example, be excited after carbonyl absorption ultraviolet light, homolysis easily occurs for the α keys of carbonyl, the surface free radical of generation and free
Free radical can trigger monomer to polymerize, generation graft copolymer and homopolymer.(2) free radical chain transfer method.Utilize free basal orientation
The transfer of polymer produces free radical, further initiation grafting reaction in polymer surfaces.Styrax class sensitising agent (such as styrax
Double methyl ethers, benzoin ethyl ether, benzoin isobutyl ether etc.) by the reaction of NorrishI types after ultraviolet irradiation, can be undergone, produce two
Free radical, when monomer concentration is very low, two free basal orientation polymer surfaces chain tra nsfers, produce surface free radical and then initiation connects
Branch polymerisation, but two free radicals can also trigger monomer to produce monomer radical, further generate homopolymer.(3) hydrogen is taken by force anti-
Ying Fa.Fragrant ketone sensitising agent (such as benzophenone), the higher singlet of energy, Ran Houxun are excited to after ultraviolet light is absorbed
Jump is altered between speed system to the triplet state that energy is relatively low but the life-span is longer.Being in the aromatic ketone of triplet state can take by force from polymer surface
Hydrogen is taken, semipinacol free radical itself is reduced into, while generating a macromolecular radical, big point in polymer surface
Sub- free radical can trigger the polymerization of monomer, generate macromolecular chain.Semipinacol free radical activity is relatively low, is difficult radical polymerization
Close, but chain termination reaction is participated in easily by coupling reaction, therefore the grafting efficiency of this method is higher.
Hydrogen abstraction reaction method is divided into one-step method and two-step method again.(1) one-step method.Macromolecule is placed in the molten of sensitising agent and monomer
Photografting polymerization is directly carried out in liquid, it is easy to operate, but because the sensitising agent of excitation state is when capturing high molecular hydrogen atom,
The hydrogen atom formation monomer radical on monomer can be captured, substantial amounts of homopolymer is produced, cause wastage of material and grafting rate to reduce.
In addition, light trigger can also crosslink grafted chain from abstract hydrogen atoms on the polymer chain of grafting.(2) two-step method.It is first
Macromolecule is first put into illumination certain time in photosensitizing agent solution, sensitising agent abstract hydrogen atoms formation surface from macromolecule is free
Base and semipinacol free radical, under conditions of monomer-free presence, both form polymeric initiator at coupling；Then, by high score
Son takes out washing, places into monomer solution and irradiates, and the polymeric initiator of first step generation resolves into high molecular free radical again
With semipinacol free radical, high molecular free radical again with monomer reaction, formed graft polymers.Because semipinacol free radical is lived
Property it is low, and be easy to be coupled or terminate increase chain, so two-step method can reduce the formation of homopolymer.Further, since macromolecule
The formation of initiator and the generation that is graft-polymerized are in different step, so grafting density and grafted chain length can be controlled effectively.
But, due to being still grafted in the second step of two-step method using illumination, need washing to remove unnecessary sensitising agent before illumination, to avoid
A large amount of homopolymers are generated, thickness, macromolecule treating capacity to monomer solution etc. also have certain limitations, and there is cumbersome and process
The problems such as being difficult amplification.
The content of the invention
It is an object of the invention to overcome the shortcoming of traditional high-molecular optical initiation grafting method, using the pre- work of ultraviolet light
Change/heating triggers two-step method to carry out modification of graft to macromolecule.
The principle of technical solution of the present invention is：Macromolecule is put into photosensitizing agent solution first and carries out ultraviolet light irradiation, light
Quick dose of abstract hydrogen atoms formation surface free radical and semipinacol free radical from macromolecule, under conditions of monomer-free presence,
Both form polymeric initiator at coupling, exist due to only having macromolecule in the step with sensitising agent, can improve high molecular work
Change efficiency；Then, add monomer and heat, polymeric initiator is decomposed generation high molecular free radical and semipinacol freedom
Base, high molecular free radical is graft-polymerized with monomer again, obtains modified high-molecular.Described macromolecule is Polymer Solution or solid
Body.This method can reduce homopolymer generation, be conducive to improving grafting rate, it is unnecessary that second step heating is removed before triggering without washing
Sensitising agent, it is simple to operate, larger liquor capacity can be used during heating initiation grafting, macromolecule treating capacity is big, and process is easy
In amplification.During using Polymer Solution, macromolecule and sensitising agent and the abundant haptoreaction of monomer can be made, be conducive to improving grafting
Rate.
A kind of method of macromolecular grafted polymerization, it is characterised in that：Macromolecule is put into photosensitizing agent solution first and carried out
Ultraviolet light irradiation, occurs high molecular smooth pre-activate, generates polymeric initiator；Then, add monomer and heat, macromolecule draws
Send out agent and decompose generation high molecular free radical and semipinacol free radical, high molecular free radical is graft-polymerized with monomer, changed again
Property macromolecule.Described macromolecule is polymeric solid or solution.
Embodiment
Technical scheme is further described with reference to embodiment.
Embodiment 1：Polypropylene grafted acrylic acid
1.067g polypropylene (7wt%) and 0.74605g benzophenone (5wt%) dissolving are added in 15mL DMF, leads to nitrogen
After gas deoxygenation, a period of time is stirred under ultraviolet lighting；Then polypropylene is washed and removes unnecessary sensitising agent, add propylene
Acid, inflated with nitrogen deoxygenation is heated to 60 DEG C of stirring 2h.Product is centrifuged, 24h is extracted in cable type extractor according with ethanol, removes not anti-
The acrylic acid and homopolymer answered, dry product, grafting rate reach 2.72%.
Embodiment 2：Kynoar is grafted 4-vinylpyridine
PVDF powder (1.067g) is dissolved in 15ml DMF and obtains 7wt% Polymer Solutions；Add sensitising agent BP
After (0.746g, 5wt%) fully dissolving, N is passed through215min removes the O in solution2；After ultraviolet light irradiation activation 40min,
Generate PVDF initiator molecules.In PVDF solution after UV photoactivation, addition 4-vinylpyridine (4-VP) 1mL (0.984g,
6.49wt%), after stirring, N is led to210min, excludes the O in container2；Stirring reaction 1h under normal temperature, makes the activity on PVDF
Group fully reacts with 4-VP；Then heat to 60 DEG C of reaction 2h；It is cooled to after room temperature, adds ethanol in reaction solution, make production
Thing is separated out, and is centrifuged (10000rpm, 3min)；Then washed with ethanol dispersed with stirring remove for 3 times unreacted BP, 4-VP and
Homopolymer.It is dried in vacuo (60 DEG C), obtains modified high-molecular PVDF-4VP, yield is 95.31%, and grafting rate is 4.13%.
Embodiment 3：Kynoar is grafted caffeic acid
1.067g Kynoar (PVDF, 7wt%) and 0.74605g benzophenone (5wt%) are added in 15mL DMF
Dissolving, leads to after nitrogen deoxygenation, and a period of time is stirred under ultraviolet lighting, caffeic acid is then added, inflated with nitrogen deoxygenation is heated to 60
DEG C stirring 2h.Product is centrifuged, 24h is extracted in cable type extractor according with ethanol, removes unreacted caffeic acid and the poly- coffee of homopolymer
Coffee acid, dry product, grafting rate reaches 1.13%.
Claims (2)
1. a kind of method of macromolecular grafted polymerization, it is characterised in that：Macromolecule is put into photosensitizing agent solution first and carries out purple
Outer light irradiation, makes macromolecule occur photoactivation, generates polymeric initiator；Then, add monomer and heat, trigger macromolecule
Generation high molecular free radical and semipinacol free radical are decomposed in agent, and high molecular free radical is graft-polymerized with monomer, is modified again
Macromolecule.
2. method according to claim 1, it is characterised in that：Described macromolecule is Polymer Solution or solid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710624953.9A CN107286272A (en) | 2017-07-27 | 2017-07-27 | A kind of method of macromolecular grafted polymerization |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710624953.9A CN107286272A (en) | 2017-07-27 | 2017-07-27 | A kind of method of macromolecular grafted polymerization |
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| CN107286272A true CN107286272A (en) | 2017-10-24 |
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| CN201710624953.9A Pending CN107286272A (en) | 2017-07-27 | 2017-07-27 | A kind of method of macromolecular grafted polymerization |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116179080A (en) * | 2023-03-10 | 2023-05-30 | 深圳市纳能科技有限公司 | Anti-fouling high-weather-resistance damping coating and preparation method thereof |
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|---|---|---|---|---|
| CN1508171A (en) * | 2002-12-18 | 2004-06-30 | 中国科学院生态环境研究中心 | Dynamic method for polymer surface photografting |
| CN101302279A (en) * | 2008-06-06 | 2008-11-12 | 北京化工大学 | Method for preparing block copolymer by using re-initiating dormant group |
| CN101307122A (en) * | 2008-06-27 | 2008-11-19 | 北京化工大学 | Light polymerization process for preparing block or graft polymer |
| CN101386653A (en) * | 2007-09-11 | 2009-03-18 | 中国科学院生态环境研究中心 | Homogeneous ultraviolet radiation graft method and equipment |
| CN105622866A (en) * | 2016-03-27 | 2016-06-01 | 北京化工大学 | Method for preparing water-soluble graft polymers based on active/controllable radical polymerization |
-
2017
- 2017-07-27 CN CN201710624953.9A patent/CN107286272A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1508171A (en) * | 2002-12-18 | 2004-06-30 | 中国科学院生态环境研究中心 | Dynamic method for polymer surface photografting |
| CN101386653A (en) * | 2007-09-11 | 2009-03-18 | 中国科学院生态环境研究中心 | Homogeneous ultraviolet radiation graft method and equipment |
| CN101302279A (en) * | 2008-06-06 | 2008-11-12 | 北京化工大学 | Method for preparing block copolymer by using re-initiating dormant group |
| CN101307122A (en) * | 2008-06-27 | 2008-11-19 | 北京化工大学 | Light polymerization process for preparing block or graft polymer |
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Cited By (2)
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| CN116179080A (en) * | 2023-03-10 | 2023-05-30 | 深圳市纳能科技有限公司 | Anti-fouling high-weather-resistance damping coating and preparation method thereof |
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