CN110003371A - A kind of polymerization of UV light-induced atom transferred free radical - Google Patents
A kind of polymerization of UV light-induced atom transferred free radical Download PDFInfo
- Publication number
- CN110003371A CN110003371A CN201910300779.1A CN201910300779A CN110003371A CN 110003371 A CN110003371 A CN 110003371A CN 201910300779 A CN201910300779 A CN 201910300779A CN 110003371 A CN110003371 A CN 110003371A
- Authority
- CN
- China
- Prior art keywords
- polymerization
- free radical
- light
- transferred free
- atom transferred
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 25
- 150000003254 radicals Chemical class 0.000 title claims abstract description 17
- 229920000642 polymer Polymers 0.000 claims abstract description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- 239000000178 monomer Substances 0.000 claims abstract description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000003999 initiator Substances 0.000 claims abstract description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 7
- 239000011261 inert gas Substances 0.000 claims abstract description 6
- 238000000926 separation method Methods 0.000 claims abstract description 6
- 239000002904 solvent Substances 0.000 claims abstract description 5
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 5
- PNGLEYLFMHGIQO-UHFFFAOYSA-M sodium;3-(n-ethyl-3-methoxyanilino)-2-hydroxypropane-1-sulfonate;dihydrate Chemical compound O.O.[Na+].[O-]S(=O)(=O)CC(O)CN(CC)C1=CC=CC(OC)=C1 PNGLEYLFMHGIQO-UHFFFAOYSA-M 0.000 claims description 5
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical class NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 5
- XZKFBZOAIGFZSU-UHFFFAOYSA-N 1-bromo-4-methylpentane Chemical compound CC(C)CCCBr XZKFBZOAIGFZSU-UHFFFAOYSA-N 0.000 claims description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N Vilsmeier-Haack reagent Natural products CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 4
- SIXOAUAWLZKQKX-UHFFFAOYSA-N carbonic acid;prop-1-ene Chemical compound CC=C.OC(O)=O SIXOAUAWLZKQKX-UHFFFAOYSA-N 0.000 claims description 4
- DULCUDSUACXJJC-UHFFFAOYSA-N Ethyl phenylacetate Chemical class CCOC(=O)CC1=CC=CC=C1 DULCUDSUACXJJC-UHFFFAOYSA-N 0.000 claims description 3
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 claims description 3
- -1 dichloromethane Alkane Chemical class 0.000 claims description 3
- QTKPMCIBUROOGY-UHFFFAOYSA-N 2,2,2-trifluoroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)F QTKPMCIBUROOGY-UHFFFAOYSA-N 0.000 claims description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 2
- 229940113088 dimethylacetamide Drugs 0.000 claims description 2
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 claims description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims 1
- YFDSDPIBEUFTMI-UHFFFAOYSA-N tribromoethanol Chemical compound OCC(Br)(Br)Br YFDSDPIBEUFTMI-UHFFFAOYSA-N 0.000 claims 1
- 229950004616 tribromoethanol Drugs 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 abstract description 3
- 239000002184 metal Substances 0.000 abstract description 3
- 239000012620 biological material Substances 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 238000003760 magnetic stirring Methods 0.000 abstract description 2
- 239000003863 metallic catalyst Substances 0.000 abstract description 2
- 239000002244 precipitate Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 14
- 238000000034 method Methods 0.000 description 8
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000010526 radical polymerization reaction Methods 0.000 description 5
- 238000013019 agitation Methods 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000012711 chain transfer polymerization Methods 0.000 description 2
- 238000013467 fragmentation Methods 0.000 description 2
- 238000006062 fragmentation reaction Methods 0.000 description 2
- 239000013033 iniferter Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 238000010550 living polymerization reaction Methods 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 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
- C08F120/00—Homopolymers 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
- C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F120/10—Esters
- C08F120/12—Esters of monohydric alcohols or phenols
- C08F120/14—Methyl esters, e.g. methyl (meth)acrylate
-
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerization Catalysts (AREA)
Abstract
The invention discloses a kind of polymerizations of UV light-induced atom transferred free radical, the following steps are included: catalyst, initiator and acrylate monomer are dissolved in solvent, it is placed in inert gas environment and reacts, it polymerize under the conditions of room temperature ultraviolet light under magnetic stirring, polymer is dissolved with tetrahydrofuran, it precipitates in methyl alcohol, obtains polymer after separation is dry.Polymerization process of the present invention is simple, and does not use metallic catalyst, without metal residual in obtained polymer, has huge application potential in fine chemistry industry, intelligence load medicine and technical field of biological material.
Description
Technical field
The invention belongs to polymerization technique fields, and in particular to a kind of polymerization side of UV light-induced atom transferred free radical
Method.
Background technique
Free radical polymerization has many advantages, such as that monomer is extensive, synthesis technology is various, easy to operate, industrialization is at low cost, simultaneously
It can be applied to the polymerization and copolymerization of functional monomer, 60% or more polymer all is produced to obtain by free radical polymerization.From
It is had been a hot spot of research by the living polymerization that base polymerize.Active free radical polymerization is used to prepare poly- with accurate primary structure
Object (composition, size distribution, shape, sequence distribution and regularity) is closed, the molecular weight of polymer can design prediction, obtain molecular weight
The polymer of narrowly distributing.
The main method of active free radical polymerization has Iniferter, stable nitrogen-oxygen free radical regulation polymerization at present
Method, atom transfer radical polymerization and reversible addion-fragmentation chain transfer polymerization.What wherein Iniferter obtained is poly-
The distribution of adduct molecule amount is wide, and oxynitrides used in stable nitrogen-oxygen free radical regulation polymerization could generate freedom at high temperature
Base, energy consumption is high, and the type of applicable monomer is few；The double thioes derivatives of the chain transfer agents of reversible addion-fragmentation chain transfer polymerization
Toxicity is big, and preparation process is complicated, and removal and conversion are difficult, and reagent expensive price, it is difficult to obtain；Atom transferred free radical is poly-
It closes the transition metal complex catalyst used not consume in the course of the polymerization process, hardly possible purification, metal residue will limit polymer
Application.
Summary of the invention
In view of this, the present invention provides a kind of polymerizations of UV light-induced atom transferred free radical, with organic small
Molecule obtains monomer conversion high (60% or more), molecular weight meets theoretical value, narrow molecular weight distribution (< 1.4) as catalyst
Polymer.
In order to achieve the above technical purposes, the present invention is realized especially by following technical scheme:
A kind of polymerization of UV light-induced atom transferred free radical, comprising the following steps: by catalyst, initiator and
Acrylate monomer is dissolved in solvent, is placed in inert gas environment and is reacted, under magnetic stirring room temperature ultraviolet light item
It polymerize under part, polymer is dissolved with tetrahydrofuran, is precipitated in methyl alcohol, obtains polymer after separation is dry.
Further, the molar ratio of the acrylate monomer, initiator and catalyst is 100:1:1~100:1:3.
Further, the catalyst is selected from small organic molecule hexafluorophosphoric acid triaryl sulfanilamide salt (TSPF6).
Further, the initiator is selected from the atom transfers such as 2- isobutyl ethyl bromide or alpha-brominated ethyl phenylacetate certainly
By base polymerization initiator.
Further, the acrylate monomer be selected from methyl methacrylate, methacrylic acid diamino ethyl ester,
Glycidyl methacrylate, 2-hydroxyethyl methacrylate, trifluoroethyl methacrylate, acrylonitrile, acrylic acid fourth
Ester, butyl methacrylate, lauryl methacrylate or benzyl methacrylate etc..
Further, the solvent is selected from propene carbonate, tetrahydrofuran, NN- dimethylformamide, NN- dimethyl
Acetamide, toluene, methylene chloride, chloroform or dimethyl sulfoxide.
The method of the present invention can be used for synthesizing homopolymer, can be used for synthetic copolymer (block, random, grafting, alternating).
The invention has the benefit that
1) the method for the present invention is based on organic catalyst cheap and easy to get, without using metallic catalyst, in obtained polymer
Without metal residual, there is huge application potential in fine chemistry industry, intelligence load medicine and technical field of biological material.
2) the method for the present invention is based on active free radical polymerization, and the feature of the active polymerization of obtained polymer obtains monomer
High conversion rate (60% or more), molecular weight meet the polymer of theoretical value, narrow molecular weight distribution (< 1.4).
3) low (tasteless colourless), the catalyst of catalyst toxicity of the present invention has the mild (room of highly dissoluble, reaction condition
Temperature).
Specific embodiment
Below in conjunction with specific embodiment of the present invention, technical solution of the present invention is clearly and completely described, is shown
So, described embodiments are only a part of the embodiments of the present invention, instead of all the embodiments.Based on the reality in the present invention
Example is applied, every other embodiment obtained by those of ordinary skill in the art without making creative efforts all belongs to
In the scope of protection of the invention.
Embodiment 1
A kind of non-metallic organocatalyst of UV light-induced atom transfer radical polymerization, described is nonmetallic organic
Its structural formula of catalyst is as follows:
A kind of polymerization of UV light-induced atom transferred free radical, comprising the following steps:
By methyl methacrylate, 2- isobutyl ethyl bromide and hexafluorophosphoric acid triaryl sulfanilamide salt (8000:80:240) add
Enter into reaction tube (propene carbonate accounts for 50%), magneton is added, lead to inert gas (nitrogen or argon gas) 3 minutes, closes anti-
Should pipe piston, at room temperature under magnetic agitation, and cause methyl methacrylate polymerization with ultraviolet light, beaten after 6h
Reaction tube is opened, polymer is dissolved with tetrahydrofuran, is precipitated in methyl alcohol, polymer is obtained after separation is dry, is turned after weighing
Rate is 60%, theoretical molecular weight 6000.It is 6500 with the molecular weight that gel permeation chromatography measures polymer, molecular weight
It is distributed as 1.33.
Embodiment 2
A kind of polymerization of UV light-induced atom transferred free radical, comprising the following steps:
By methyl methacrylate, alpha-brominated ethyl phenylacetate and hexafluorophosphoric acid triaryl sulfanilamide salt (8000:80:240)
It is added in reaction tube (propene carbonate accounts for 50%), magneton is added, lead to inert gas (nitrogen or argon gas) 3 minutes, close
Reaction tube piston at room temperature under magnetic agitation, and causes methyl methacrylate polymerization with ultraviolet light, after 4h
Reaction tube is opened, polymer is dissolved with tetrahydrofuran, is precipitated in methyl alcohol, polymer is obtained after separation is dry, is obtained after weighing
Conversion ratio is 55%, theoretical molecular weight 5500.It is 6400 with the molecular weight that gel permeation chromatography measures polymer, molecule
Amount is distributed as 1.33.
Embodiment 3
A kind of polymerization of UV light-induced atom transferred free radical, comprising the following steps:
By benzyl methacrylate, 2- isobutyl ethyl bromide and hexafluorophosphoric acid triaryl sulfanilamide salt (8000:80:80) add
Enter into reaction tube (tetrahydrofuran accounts for 50%), magneton is added, lead to inert gas (nitrogen or argon gas) 3 minutes, closes reaction
Pipe piston causes polymerization with ultraviolet light under magnetic agitation at room temperature, opens reaction tube after 3h, poly- with tetrahydrofuran dissolution
Object is closed, is precipitated in n-hexane, obtains polymer after separation is dry, it is 90% that conversion ratio is obtained after weighing, theoretical molecular weight
It is 16000.It is 14000 with the molecular weight that gel permeation chromatography measures polymer, molecular weight distribution 1.40.
It although an embodiment of the present invention has been shown and described, for the ordinary skill in the art, can be with
Understand without departing from the principles and spirit of the present invention can to these examples carry out it is a variety of variation, modification, replacement and
Modification, the scope of the present invention is defined by the appended.
Claims (6)
1. a kind of polymerization of UV light-induced atom transferred free radical, which comprises the following steps:
Catalyst, initiator and acrylate monomer are dissolved in solvent, is placed in inert gas environment and reacts, is stirred in magnetic force
It mixes and polymerize under the conditions of lower room temperature ultraviolet light, polymer is dissolved with tetrahydrofuran, is precipitated in methyl alcohol, obtained after separation is dry
Polymer.
2. a kind of polymerization of UV light-induced atom transferred free radical according to claim 1, which is characterized in that institute
The molar ratio of acrylate monomer, initiator and the catalyst stated is 100:1:1~100:1:3.
3. a kind of polymerization of UV light-induced atom transferred free radical according to claim 2, which is characterized in that institute
The catalyst stated is selected from small organic molecule hexafluorophosphoric acid triaryl sulfanilamide salt.
4. a kind of polymerization of UV light-induced atom transferred free radical according to claim 2, which is characterized in that institute
It is poly- for atom transferred free radical that the initiator stated is selected from 2- isobutyl ethyl bromide, alpha-brominated ethyl phenylacetate or ethobrom etc.
The initiator of conjunction.
5. a kind of polymerization of UV light-induced atom transferred free radical according to claim 2, which is characterized in that institute
The acrylate monomer stated is selected from methyl methacrylate, methacrylic acid diamino ethyl ester, methyl propenoic acid glycidyl
Ester, 2-hydroxyethyl methacrylate, trifluoroethyl methacrylate, acrylonitrile, butyl acrylate or methacrylic acid benzyl
Ester, butyl methacrylate, lauryl methacrylate etc..
6. a kind of polymerization of UV light-induced atom transferred free radical according to claim 1, which is characterized in that institute
The solvent stated is selected from propene carbonate, tetrahydrofuran, NN- dimethylformamide, NN- dimethyl acetamide, toluene, dichloromethane
Alkane, chloroform or dimethyl sulfoxide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910300779.1A CN110003371B (en) | 2019-04-15 | 2019-04-15 | Ultraviolet light induced atom transfer free radical polymerization method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910300779.1A CN110003371B (en) | 2019-04-15 | 2019-04-15 | Ultraviolet light induced atom transfer free radical polymerization method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN110003371A true CN110003371A (en) | 2019-07-12 |
| CN110003371B CN110003371B (en) | 2021-04-09 |
Family
ID=67171959
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910300779.1A Active CN110003371B (en) | 2019-04-15 | 2019-04-15 | Ultraviolet light induced atom transfer free radical polymerization method |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN110003371B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111072825A (en) * | 2020-01-10 | 2020-04-28 | 西北大学 | Carbon nitride catalyzed atom transfer radical polymerization method |
| CN115894773A (en) * | 2022-12-07 | 2023-04-04 | 郑州德派医疗器械有限公司 | Light-cured 3D printing resin for dentistry and preparation method thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105601777A (en) * | 2016-03-22 | 2016-05-25 | 苏州大学 | Visible-radiation-based water-soluble monomer atom transfer radical polymerization (ATRP) method |
-
2019
- 2019-04-15 CN CN201910300779.1A patent/CN110003371B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105601777A (en) * | 2016-03-22 | 2016-05-25 | 苏州大学 | Visible-radiation-based water-soluble monomer atom transfer radical polymerization (ATRP) method |
Non-Patent Citations (1)
| Title |
|---|
| IAN A. BARKER AND ANDREW P. DOVE: "《Triarylsulfonium hexafluorophosphate salts as photoactivated acidic catalysts for ring-opening polymerisation》", 《CHEMCOMM》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111072825A (en) * | 2020-01-10 | 2020-04-28 | 西北大学 | Carbon nitride catalyzed atom transfer radical polymerization method |
| CN115894773A (en) * | 2022-12-07 | 2023-04-04 | 郑州德派医疗器械有限公司 | Light-cured 3D printing resin for dentistry and preparation method thereof |
| CN115894773B (en) * | 2022-12-07 | 2024-05-14 | 郑州德派医疗器械有限公司 | Photo-curing 3D printing resin for dentistry and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN110003371B (en) | 2021-04-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6355718B1 (en) | Microgels and process for their preparation | |
| EP0089530A2 (en) | Polimerization process of optically active polymer and catalyst therefor | |
| EP0229481A2 (en) | Pentacyanocobaltate(II) catalytic chain transfer agents for molecular weight control in free radical polymerization | |
| Liu et al. | Dihydroxyl-terminated telechelic polymers prepared by RAFT polymerization using functional trithiocarbonate as chain transfer agent | |
| CN110003371A (en) | A kind of polymerization of UV light-induced atom transferred free radical | |
| MXPA97002791A (en) | Polymerization process of radicals lib | |
| US20140256898A1 (en) | Process for preparing branched polymer | |
| Abu-Surrah et al. | Pentacoordinated iron (II) complexes with 2, 6-bis [(imino) ethyl] pyridine-Schiff base ligands as new catalyst systems mediated atom transfer radical polymerization of (meth) acrylate monomers | |
| CA1313922C (en) | Macromonomer compositions | |
| CN102167766A (en) | Vinyl amino acid (ester) polymer and preparation method thereof | |
| CN101003590A (en) | Hydrophilic macromonomer, and preparation method | |
| CN106046221B (en) | The catalyst and polymerization of a kind of reversible-suspend mode free radical polymerization | |
| JP2009024162A (en) | Difunctional living radical polymerization initiator and method for producing polymer | |
| CN114149527A (en) | Method for realizing controllable free radical polymerization in air atmosphere and application thereof | |
| JP2014133801A (en) | Chain transfer agent, and method for producing block copolymer | |
| CN1297459A (en) | Method for production of polymers from N-vinyl compounds | |
| CN102321198B (en) | Method for preparing bimodal distribution polymer | |
| Zhu et al. | Study on reversible addition-fragmentation chain transfer (RAFT) polymerization of MMA in the presence of 2-cyanoprop-2-yl 1-dithiophenanthrenate (CPDPA) | |
| JP2957919B2 (en) | Living random (meth)acrylic copolymers and copolymers obtained therefrom and methods for their anionic copolymerization | |
| CN115043985B (en) | Series agent for core-shell structure water-based paint and preparation method and application thereof | |
| CN110305271A (en) | A kind of method of UV light-induced one-pot synthesis block polymer | |
| TWI838455B (en) | (Meth)acrylate monomers and polymers containing cyclic carbonate groups | |
| CN102432722A (en) | Method for preparing rosin-based regular polymers | |
| CN102746476A (en) | Trithiocarbonate compound containing epoxy group, preparation method and application thereof | |
| CN103242466B (en) | The method of RAFT polymer ends thiocarbonyl is removed under a kind of room temperature |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |