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Method for preparing crosslinkable segmented copolymer by utilizing active free radical soap-free emulsion polymerization and prepared compound thereof

A soap-free emulsion polymerization and compound technology, which is applied in the field of polymer chemistry, can solve the problems that polymers contain metal impurities such as copper, are sensitive to oxygen, and require expensive nitrogen-containing or phosphorus-containing ligands, etc.

Inactive Publication Date: 2010-09-08
JIANGXI SCI & TECH NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Of course, the ATRP method also has disadvantages, such as being sensitive to oxygen, containing metal impurities such as copper in the polymer, and requiring more expensive nitrogen-containing or phosphorus-containing ligands, etc.
However, in the free radical polymerization in which allyl methacrylate (AMA) is a monomer, both the bulk polymerization and the solution polymerization system are difficult to retain the allyl double bond after the reaction; Most of the allylic double bonds are retained (Matsumoto, A; Kodama, K; Mori, Y; Aota, H. J.M.S.-Pure Appl. Chem. , 1998, A33, 1459-1472.)
So far, there is no report on the preparation of crosslinkable block copolymers by living free radical soap-free emulsion polymerization

Method used

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  • Method for preparing crosslinkable segmented copolymer by utilizing active free radical soap-free emulsion polymerization and prepared compound thereof
  • Method for preparing crosslinkable segmented copolymer by utilizing active free radical soap-free emulsion polymerization and prepared compound thereof
  • Method for preparing crosslinkable segmented copolymer by utilizing active free radical soap-free emulsion polymerization and prepared compound thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1 2

[0058] The preparation of embodiment 1 two (2-bromo-isobutyric acid) polyethylene glycol-2000 diesters (Ia)

[0059] The target compound was prepared from polyethylene glycol-2000, 2-bromoisobutyryl bromide and triethylamine.

[0060] Weigh PEG-2000 (20 g, 10 mmol) into a reaction flask, and then add dry tetrahydrofuran (30 mL). After the dissolution was complete, an excess of dry triethylamine (50 mmol, 5 times that of PEG-2000) was added. Under the protection of argon, 2-bromoisobutyryl bromide (6.9 g, 30 mmol, 3.75 mL) was dissolved in dry tetrahydrofuran (30 mL), and then slowly added dropwise into the reaction flask. The reaction system was reacted at 40°C for 48h. After the reaction was completed, filter, discard the filter cake, and distill the filtrate to remove the solvent under reduced pressure to obtain a light brown viscous liquid. Anhydrous diethyl ether was added to the viscous liquid, mixed well to precipitate solids, filtered, and the resulting filter cake w...

Embodiment 22

[0063] The preparation of embodiment 22-bromopropionic acid polyethylene glycol (800) monomethyl ether ester (Ib)

[0064] The target compound was prepared from polyethylene glycol (800) monomethyl ether, 2-bromopropionic acid, dicyclohexylcarbodiimide (DCC), and 4-N,N-dimethylaminopyridine (DMAP).

[0065] Weigh PEG-800 (8 g, 10 mmol) and 2-bromopropionic acid (1.53 g, 10 mmol) into a reaction flask, and then add dry tetrahydrofuran (25 mL). After the dissolution was complete, an excess of DCC (5.15 g, 25 mmol) was added, followed by a catalytic amount of DMAP. Under the protection of argon, the system was reacted at 25°C for 48h. After the reaction was completed, filter, discard the filter cake, and distill the filtrate to remove the solvent under reduced pressure to obtain a light brown viscous liquid. Add cold anhydrous diethyl ether to the viscous liquid, mix well to precipitate solids, filter, put the obtained filter cake in a vacuum drying oven, and dry at 40°C until ...

Embodiment 3

[0067] Example 3 Utilize the two (2-bromo-isobutyric acid) polyethylene glycol-2000 diester (Ia) prepared in Example 1 to carry out atom transfer radical emulsion polymerization of allyl methacrylate (AMA)

[0068] will be pre-treated with glacial acetic acid to remove possible CuBr 2 Impurity CuBr (0.0143g, 0.1mmol) and 2,2'-bipyridine (0.0156g, 0.1mmol) were added to the reaction flask, and an appropriate amount of deionized water (5-10g) was added to dissolve into a blue solution. Under the protection of argon, add bis(2-bromo-isobutyric acid)polyethylene glycol-2000 diester (Ia) (0.3276g, 0.14mmol) and AMA monomer (2.524g, 20mmol), stir at high speed for 30min, Until the system is stable without delamination. The above reaction was moved to a 60°C oil bath and stirred at a medium speed for 5h. During the reaction, samples were taken at regular intervals to track the progress of the reaction.

[0069] After the reaction, use lower alcohol to break the emulsion, and the m...

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Abstract

The invention discloses an active free radical soap-free emulsion polymerization reaction, a prepared crosslinkable segmented copolymer thereof and application of the copolymer. The copolymer is prepared through the following steps: under the protection of nitrogen gas or argon gas, mixing an allyl methacrylate monomer, other monomers, a compound with a structural formula (I), a catalyst and a ligand according to a certain mol ratio, stirring, reacting at the temperature of 40 to 80 DEG C for 5 to 20 hours, and purifying to obtain the copolymer. Other monomers are selected from one or more in an acrylic compound, a methacrylic compound and a styrene compound; the catalyst is selected from one of the chloride or the bromide of copper, iron, nickel or ruthenium; and the ligand is selected from one of 2, 2'-dipyridyl, 4, 4'- di(5-nonyl)dipyridyl, N, N, N', N'-tetramethylethylenediamine, pentamethyldiethylenetriamine, hexamethyltriethylenetetramine or methenamine. The invention also discloses the application of the compound with the structural formula (I) as an emulsifier and an initiator.

Description

technical field [0001] The invention relates to the field of macromolecule chemistry, in particular to a method for preparing a cross-linkable copolymer by active free radical soap-free emulsion polymerization and a compound prepared therefrom. Background technique [0002] Living / controllable radical polymerization (L / CRP) is a new type of polymerization method developed in recent years. Compared with traditional free radical polymerization, this method has the advantages of narrow molecular weight distribution, controllable molecular weight, and molecular weight. controllable structure etc. Compared with living ion polymerization, living radical polymerization has many advantages such as wide application of monomers, easy realization of reaction conditions, and the ability to carry out in different systems such as water. Living / Controlled Radical Polymerization (L / CRP) mainly includes atom transfer radical polymerization (ATRP), reversible addition-fragmentation chain tra...

Claims

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Application Information

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IPC IPC(8): C08F293/00C08F2/22C09D153/00C09D11/10C09J153/00C09D11/107
Inventor 申亮程传杰付全磊
Owner JIANGXI SCI & TECH NORMAL UNIV
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