CN1970648A - Method for preparing dispersive type carbon black adopting surface graft modification method - Google Patents
Method for preparing dispersive type carbon black adopting surface graft modification method Download PDFInfo
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- CN1970648A CN1970648A CN 200610155007 CN200610155007A CN1970648A CN 1970648 A CN1970648 A CN 1970648A CN 200610155007 CN200610155007 CN 200610155007 CN 200610155007 A CN200610155007 A CN 200610155007A CN 1970648 A CN1970648 A CN 1970648A
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Abstract
The invention discloses a making method of dispersing carbon black through surface grafting modifying method, which is characterized by the following: making a series of polymer with HTEMPO terminal group polymerized by controllable free radiacal; decomposing HTEMPO into polymer free radical under higher temperature; making non-paired electron on the surface of carbon black catch polymer free radical; obtaining the modified carbon black grafted by polymer; dispersing the modified carbon black in multiple organic solvents; applying in the PTC material, air-sensitive material and ink domain.
Description
Technical field
The present invention relates to a kind of employing surface graft modification legal system and be equipped with dispersed sooty method.
Background technology
Carbon black normally diameter mainly is made up of carbon at the aggregate of little carbon granule of 10～400nm, and carbon content is usually 90～99%, and its surface arrangement functional groups such as a spot of carboxyl, phenolic hydroxyl group, quinonyl and lactone group.Carbon black has been widely used in the preparation of conducing composite material, gas sensitive, coating and printing ink etc., is a kind of extremely important industrial chemicals.The basic condition that carbon black can enter these systems is that carbon black can disperse in these solvent systems or polymeric system well.Usually, carbon black is to be difficult to dispersive in these systems, and it is to improve one of effective ways of the dispersiveness of carbon black in solvent and in polymkeric substance that carbon blacksurface is carried out graft modification, also is the core technology of improving the carbon black products performance.
The method that the graft modification carbon black adopts usually has three kinds, be the surface graft modification method that the carbon blacksurface unpaired electron is caught free polymer readical, carbon blacksurface initiating group trigger monomer polymeric surface graft modification method and carbon blacksurface group and contain between the reactive end based polyalcohol surface graft modification method that condensation reaction takes place.After carbon blacksurface was introduced various initiating groups, surperficial initiating group can carry out radical polymerization, ring-opening polymerization, anionoid polymerization and cationoid polymerisation by trigger monomer, and the common step of the method for this carbon blacksurface graft modification is more loaded down with trivial details, condition is harsh.The functional group that utilizes carbon blacksurface carries out condensation reaction with the polymkeric substance that contains reactive terminal group and prepares the graft modification carbon black, and the common step of this surface graft modification sooty method is also more, narrow application range.Carbon blacksurface has condensed ring aromatic structure and quinonoid structure and unpaired electron is arranged on it, so carbon black catches effect to free radical, can make the free polymer readical of " work " terminate in carbon blacksurface, thereby reach the purpose at the carbon blacksurface graftomer.
Summary of the invention
The object of the present invention is to provide a kind of employing surface graft modification legal system to be equipped with dispersed sooty method.
The technical solution adopted for the present invention to solve the technical problems is:
Scheme 1, the dispersed sooty step of polymer manufacture that has a HTEMPO end group are as follows:
1) with initiator, monomer and 4-hydroxyl-2,2,6, the 6-tetramethyl piperidine nitrogen oxygen free radical joins in the container, reaction system under argon shield and stirring, adopts the oil bath heating after deoxygenation, earlier 95 ℃ of reactions 1 hour, be warmed up to 125 ℃ then and continue reaction, reaction is used the ethanol sedimentation product after finishing, last vacuum-drying can make the polymkeric substance that has the HTEMPO end group;
2) polymkeric substance that has the HTEMPO end group that makes with 1 part of carbon black and 4～15 parts of carbon black weight joins in the container; with N; dinethylformamide is a solvent; reaction system is after deoxygenation; under argon shield and stirring; employing oil bath heating; be warmed up to 125 ℃ of reactions 3～24 hours; after reaction finishes; products therefrom washs with tetrahydrofuran (THF) under the condition of ultra-sonic dispersion, centrifugation then, and such supersound washing-centrifugal separation processes is carried out 6～10 times repeatedly; with the drying precipitate that obtains, promptly get modified carbon black at last.
Concrete condition is:
The initiator that is adopted when 1) preparing the polystyrene that has the HTEMPO end group is a Diisopropyl azodicarboxylate, and its consumption is 6.0 * 10
-2Mol/L; 4-hydroxyl-2,2,6, the mol ratio of 6-tetramethyl piperidine nitrogen oxygen free radical and Diisopropyl azodicarboxylate are 1.0;
The initiator that is adopted when 2) preparing poly-(vinylbenzene-co-maleic anhydride) of being with the HTEMPO end group is a benzoyl peroxide, and its consumption is 3.3 * 10
-2Mol/L; 4-hydroxyl-2,2,6, the mol ratio of 6-tetramethyl piperidine nitrogen oxygen free radical and Oxybenzene formyl is 1.8;
3) monomer of Jia Ruing is the mixture of vinylbenzene or vinylbenzene and maleic anhydride, and the consumption of maleic anhydride is the vinylbenzene of 10mol%;
4) adopt the method vacuumize to remove oxygen in the reaction system;
5) centrifugation is 30 minutes, 3000 rev/mins of rotating speeds;
6) content of polymkeric substance is 4～32% in the above-mentioned modified carbon black that makes;
7) the above-mentioned modified carbon black particle diameter that makes is at 126～198nm.
8) the above-mentioned polystyrene modified carbon black that makes and poly-(vinylbenzene-co-maleic anhydride) modified carbon black can be dispersed in organic solvent such as tetrahydrofuran (THF), N well, in dinethylformamide, the chloroform etc.
Scheme 2, the dispersed sooty step of polymer manufacture that has a HTEMPO end group are as follows:
1) with initiator, monomer and 4-hydroxyl-2,2,6, the 6-tetramethyl piperidine nitrogen oxygen free radical joins in the container, reaction system under argon shield and stirring, adopts the oil bath heating after deoxygenation, earlier 95 ℃ of reactions 1 hour, be warmed up to 130 ℃ then and continue reaction, reaction is used the ether sedimentation product after finishing, last vacuum-drying promptly makes the polymkeric substance that has the HTEMPO end group;
2) polymkeric substance that has the HTEMPO end group that makes with 1 part of carbon black and 4～15 parts of carbon black weight joins in the container two neck bottles, and with N, dinethylformamide is a solvent; reaction system is after deoxygenation; under argon shield and stirring, adopt the oil bath heating, be warmed up to 125 ℃ of reactions 3～24 hours.After reaction finished, products therefrom was used N under the condition of ultra-sonic dispersion, and dinethylformamide washs, centrifugation then, and such supersound washing-centrifugal separation processes is carried out 6～10 times repeatedly, at last with the drying precipitate that obtains, promptly makes modified carbon black.
Concrete condition is:
1) preparation have the HTEMPO end group poly-(4-vinylpyridine) time initiator that adopted be benzoyl peroxide, its consumption is 1.84 * 10
-2Mol/L; 4-hydroxyl-2,2,6, the mol ratio of 6-tetramethyl piperidine nitrogen oxygen free radical and benzoyl peroxide are 1.30;
The initiator that is adopted when 2) preparing poly-[vinylbenzene-co-(4-vinylpyridine)] that has the HTEMPO end group is a Diisopropyl azodicarboxylate, and its consumption is 2.5 * 10
-2Mol/L; 4-hydroxyl-2,2,6, the mol ratio of 6-tetramethyl piperidine nitrogen oxygen free radical and Diisopropyl azodicarboxylate are 1.8;
3) monomer of Jia Ruing is the mixture of 4-vinylpyridine or vinylbenzene and 4-vinylpyridine;
4) adopt the method vacuumize to remove oxygen in the reaction system;
5) centrifugation is 30 minutes, 3000 rev/mins of rotating speeds;
6) content of polymkeric substance is 12～26% in the above-mentioned modified carbon black that makes;
7) the above-mentioned modified carbon black particle diameter that makes is at 200～317nm;
8) above-mentioned poly-(4-vinylpyridine) modified carbon black that makes and poly-[vinylbenzene-co-(4-vinylpyridine)] modified carbon black can be dispersed in polar organic solvent such as N well, in dinethylformamide, the ethanol etc.
The beneficial effect that the present invention has is: preparation process is simple, only needs two steps usually, and the scope of application is wider.Can be used for carbon black catching to styrene homopolymers free radical, styrol copolymer free radical, 4-vinylpyridine homopolymer free radical and 4-vinylpyridine multipolymer free radical; Thereby can make the series polymer modified carbon black.
Description of drawings
Fig. 1 carbon black is caught the mechanism of polystyrene free radical;
The AFM figure of poly-(4-vinylpyridine) modified carbon black of Fig. 2;
The TEM figure of poly-(vinylbenzene-co-maleic anhydride) modified carbon black of Fig. 3;
Fig. 4 gathers (vinylbenzene-co-maleic anhydride) modified carbon black (A, B) deployment conditions in THF and poly-(4-vinylpyridine) modified carbon black (C, D) deployment conditions in ethanol.
A, B: poly-(vinylbenzene-co-maleic anhydride) modified carbon black leaves standstill the situation after 2 months in tetrahydrofuran (THF); C, D: poly-(4-vinylpyridine) modified carbon black leaves standstill the situation after 2 months in ethanol.
Embodiment
Embodiment 1
1) 10mL vinylbenzene (87.4mmol), 98.5mg Diisopropyl azodicarboxylate (0.6mmol) and 103.8mgHTEMPO (0.6mmol) are joined in the there-necked flask of 50ml; reaction system is after deoxygenation; under argon shield and stirring; employing oil bath heating; react 1h down at 95 ℃ earlier, be warmed up to 125 ℃ then and continue reaction 7h.Reaction is used the ethanol sedimentation product after finishing, and last vacuum-drying can make the polystyrene that has the HTEMPO end group.
2) with 50mg carbon black, 5mlN, the polystyrene of the band HTEMPO end group that dinethylformamide and 0.20g make joins in the 25ml two neck bottles, and reaction system under argon shield and stirring, adopts the oil bath heating after deoxygenation, be warmed up to 130 ℃ of reactions 24 hours.After reaction finished, products therefrom washed centrifugation then down ultrasonic with tetrahydrofuran (THF); Such supersound washing-centrifugal separation processes is carried out 6 times repeatedly, and the throw out that obtains at last promptly makes the polystyrene modified carbon black through super-dry.The mechanism that carbon black is caught the polystyrene free radical as shown in Figure 1.
Embodiment 2
1) 5mL vinylbenzene (43.7mmol), 0.4285g maleic anhydride (4.37mmol), 40mg benzoyl peroxide (0.165mmol) and 51.2mg HTEMPO (0.297mmol) are joined in the there-necked flask of 50ml; reaction system is after deoxygenation; under argon shield and stirring; employing oil bath heating; react 1h down at 100 ℃ earlier, be warmed up to 125 ℃ then and continue reaction 7h.Reaction is used the ethanol sedimentation product after finishing, and last vacuum-drying can make poly-(vinylbenzene-co-maleic anhydride) of being with the HTEMPO end group.
2) with 50mg carbon black, 5mlN; poly-(vinylbenzene-co-maleic anhydride) of the band HTEMPO end group that dinethylformamide and 0.20g make joins in the 25ml two neck bottles, and reaction system is after deoxygenation, under argon shield and stirring; employing oil bath heating is warmed up to 130 ℃ of reactions 24 hours.After reaction finished, products therefrom washed centrifugation then down ultrasonic with tetrahydrofuran (THF); Such supersound washing-centrifugal separation processes is carried out 6 times repeatedly, and the throw out that obtains at last promptly makes poly-(vinylbenzene-co-maleic anhydride) modified carbon black through super-dry.The TEM figure of poly-(vinylbenzene-co-maleic anhydride) modified carbon black as shown in Figure 3.
Embodiment 3
1) 3mL 4-vinylpyridine (28.5mmol), 13.4mg benzoyl peroxide (0.0553mmol) and 12.4mg HTEMPO (0.0721mmol) are joined in the there-necked flask of 50ml; reaction system is after deoxygenation; under argon shield and stirring; employing oil bath heating; react 1h down at 100 ℃ earlier, be warmed up to 125 ℃ then and continue reaction 7h.Reaction is used the ether sedimentation product after finishing, and last vacuum-drying promptly makes poly-(4-vinylpyridine) of being with the HTEMPO end group.
2) with 50mg carbon black, 5mlN; poly-(4-vinylpyridine) of dinethylformamide and 0.75g band HTEMPO end group joins in the 25ml two neck bottles, and reaction system is after deoxygenation, under argon shield and stirring; employing oil bath heating is warmed up to 130 ℃ of reactions 12 hours.After reaction finished, products therefrom used N, dinethylformamide to wash down ultrasonic, centrifugation then; Such supersound washing-centrifugal separation processes is carried out 6 times repeatedly, and the throw out that obtains at last promptly makes poly-(4-vinylpyridine) modified carbon black through super-dry.The AFM figure of poly-(4-vinylpyridine) modified carbon black as shown in Figure 2.
Embodiment 4
1) 5.72mL vinylbenzene (50mmol), 2.28ml 4-vinylpyridine (21.7mmol), 28.5mg Diisopropyl azodicarboxylate (0.2mmol) and 67.4mg HTEMPO (0.36mmol) are joined in the there-necked flask of 50ml; reaction system is after deoxygenation; under argon shield and stirring; employing oil bath heating; react 1h down at 95 ℃ earlier, be warmed up to 125 ℃ then and continue reaction 7h.Reaction is used the ether sedimentation product after finishing, and last vacuum-drying promptly makes poly-[vinylbenzene-co-(4-vinylpyridine)] of being with the HTEMPO end group.
2) with 50mg carbon black, 5mlN; poly-[vinylbenzene-co-(4-vinylpyridine)] of dinethylformamide and 0.50g band HTEMPO end group joins in the 25ml two neck bottles, and reaction system is after deoxygenation, under argon shield and stirring; employing oil bath heating is warmed up to 130 ℃ of reactions 12 hours.After reaction finished, products therefrom used N, dinethylformamide to wash down ultrasonic, centrifugation then; Such supersound washing-centrifugal separation processes is carried out 6 times repeatedly, and the throw out that obtains at last promptly makes poly-[vinylbenzene-co-(4-vinylpyridine)] modified carbon black through super-dry.
The test-results of table one polystyrene modified carbon black
| Run | Reaction times (h) | Polymer content (%) | Particle diameter (nm) |
| 1 2 3 4 | 3 6 12 24 | 11.67 13.03 16.68 21.17 | 138 179 185 193 |
Add fashionable polystyrene/carbon black (wt/wt)=4; Polymer content (%) is measured with TGA; Particle diameter (nm) is measured with dynamic light scattering.
The test-results of table dimerization (4-vinylpyridine) modified carbon black
| Run | Reaction times (h) | R | Polymer content (%) | Particle diameter (nm) |
| 1 2 3 | 12 12 12 | 4 10 15 | 15.60 18.53 26.87 | 200 310 317 |
Add poly-(the 4-vinylpyridine)/carbon black (wt/wt) of fashionable R=; Polymer content (%) is measured with TGA; Particle diameter (nm) is measured with dynamic light scattering.
The test-results of table trimerization (vinylbenzene-co-maleic anhydride) modified carbon black
| Run | Reaction times (h) | Polymer content (%) | Particle diameter (nm) |
| 1 2 3 4 | 3 6 12 24 | 4.88 8.92 14.81 32.68 | 126 155 176 198 |
Add fashionable poly-(vinylbenzene-co-maleic anhydride)/carbon black (wt/wt)=4; Polymer content (%) is measured with TGA; Particle diameter (nm) is measured with dynamic light scattering.
The test-results of poly-[vinylbenzene-co-(the 4-vinylpyridine)] modified carbon black of table four
| Run | Reaction times (h) | R | Polymer content (%) | Particle diameter (nm) |
| 1 2 3 | 6 12 12 12 | 4 4 10 15 | 12.31 16.17 21.77 25.67 | 287 203 267 272 |
Add poly-(vinylbenzene-co-the maleic anhydride)/carbon black (wt/wt) of fashionable R=; Polymer content (%) is measured with TGA; Particle diameter (nm) is measured with dynamic light scattering.
Claims (4)
1. one kind is adopted the surface graft modification legal system to be equipped with dispersed sooty method, it is characterized in that adopting the dispersed sooty step of the polymer manufacture that has the HTEMPO end group as follows:
1) with initiator, monomer and 4-hydroxyl-2,2,6, the 6-tetramethyl piperidine nitrogen oxygen free radical joins in the container, reaction system under argon shield and stirring, adopts the oil bath heating after deoxygenation, earlier 95 ℃ of reactions 1 hour, be warmed up to 125 ℃ then and continue reaction, reaction is used the ethanol sedimentation product after finishing, last vacuum-drying can make the polymkeric substance that has the HTEMPO end group;
2) polymkeric substance that has the HTEMPO end group that makes with 1 part of carbon black and 4～15 parts of carbon black weight joins in the container; with N; dinethylformamide is a solvent; reaction system is after deoxygenation; under argon shield and stirring; employing oil bath heating; be warmed up to 125 ℃ of reactions 3～24 hours; after reaction finishes; products therefrom washs with tetrahydrofuran (THF) under the condition of ultra-sonic dispersion, centrifugation then, and such supersound washing-centrifugal separation processes is carried out 6～10 times repeatedly; with the drying precipitate that obtains, promptly get modified carbon black at last.
2. a kind of method that adopts the surface graft modification legal system to be equipped with modified carbon black according to claim 1 is characterized in that:
The initiator that is adopted when 1) preparing the polystyrene that has the HTEMPO end group is a Diisopropyl azodicarboxylate, and its consumption is 6.0 * 10
-2Mol/L; 4-hydroxyl-2,2,6, the mol ratio of 6-tetramethyl piperidine nitrogen oxygen free radical and Diisopropyl azodicarboxylate are 1.0;
The initiator that is adopted when 2) preparing poly-(vinylbenzene-co-maleic anhydride) of being with the HTEMPO end group is a benzoyl peroxide, and its consumption is 3.3 * 10
-2Mol/L; 4--hydroxyl-2,2,6, the mol ratio of 6-tetramethyl piperidine nitrogen oxygen free radical and Oxybenzene formyl is 1.8;
3) monomer of Jia Ruing is the mixture of vinylbenzene or vinylbenzene and maleic anhydride, and the consumption of maleic anhydride is a 10mol% vinylbenzene;
4) adopt the method vacuumize to remove oxygen in the reaction system;
5) centrifugation is 30 minutes, 3000 rev/mins of rotating speeds;
6) content of polymkeric substance is 4～32% in the above-mentioned modified carbon black that makes;
7) the above-mentioned modified carbon black particle diameter that makes is at 126～198nm;
8) the above-mentioned polystyrene modified carbon black that makes and poly-(vinylbenzene-co-maleic anhydride) modified carbon black can be dispersed in organic solvent such as tetrahydrofuran (THF), N well, in dinethylformamide, the chloroform etc.
3. one kind is adopted the surface graft modification legal system to be equipped with dispersed sooty method, it is characterized in that adopting the dispersed sooty step of the polymer manufacture that has the HTEMPO end group as follows:
1) with initiator, monomer and 4-hydroxyl-2,2,6, the 6-tetramethyl piperidine nitrogen oxygen free radical joins in the container, reaction system under argon shield and stirring, adopts the oil bath heating after deoxygenation, earlier 95 ℃ of reactions 1 hour, be warmed up to 125 ℃ then and continue reaction, reaction is used the ether sedimentation product after finishing, last vacuum-drying promptly makes the polymkeric substance that has the HTEMPO end group;
2) polymkeric substance that has the HTEMPO end group that makes with 1 part of carbon black and 4～15 parts of carbon black weight joins in the container two neck bottles, and with N, dinethylformamide is a solvent; reaction system is after deoxygenation; under argon shield and stirring, adopt the oil bath heating, be warmed up to 125 ℃ of reactions 3～24 hours.After reaction finished, products therefrom was used N under the condition of ultra-sonic dispersion, and dinethylformamide washs, centrifugation then, and such supersound washing-centrifugal separation processes is carried out 6～10 times repeatedly, at last with the drying precipitate that obtains, promptly makes modified carbon black.
4. a kind of employing surface graft modification legal system according to claim 3 is equipped with dispersed sooty method, it is characterized in that:
1) preparation have the HTEMPO end group poly-(4-vinylpyridine) time initiator that adopted be benzoyl peroxide, its consumption is 1.84 * 10
-2Mol/L; 4-hydroxyl-2,2,6, the mol ratio of 6-tetramethyl piperidine nitrogen oxygen free radical and benzoyl peroxide are 1.30;
The initiator that is adopted when 2) preparing poly-[vinylbenzene-co-(4-vinylpyridine)] that has the HTEMPO end group is a Diisopropyl azodicarboxylate, and its consumption is 2.5 * 10
-2Mol/L; 4-hydroxyl-2,2,6, the mol ratio of 6-tetramethyl piperidine nitrogen oxygen free radical and Diisopropyl azodicarboxylate are 1.8;
3) monomer of Jia Ruing is the mixture of 4-vinylpyridine or vinylbenzene and 4-vinylpyridine;
4) adopt the method vacuumize to remove oxygen in the reaction system;
5) centrifugation is 30 minutes, 3000 rev/mins of rotating speeds;
6) content of polymkeric substance is 12～26% in the above-mentioned modified carbon black that makes;
7) the above-mentioned modified carbon black particle diameter that makes is at 200～317nm;
8) above-mentioned poly-(4-vinylpyridine) modified carbon black that makes and poly-[vinylbenzene-co-(4-vinylpyridine)] modified carbon black can be dispersed in polar organic solvent such as N well, in dinethylformamide, the ethanol etc.
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| CN102229759A (en) * | 2011-05-06 | 2011-11-02 | 北京化工大学 | Method for preparing white carbon black hybridized material prepared by modification with end chlorosilane polymer |
| CN103980743A (en) * | 2014-05-12 | 2014-08-13 | 梁洪奎 | Method for producing a chemically modified carbon black |
| CN104193922A (en) * | 2014-09-02 | 2014-12-10 | 三明学院 | Water-based grafting modified carbon black and preparation method thereof |
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| CN102229759A (en) * | 2011-05-06 | 2011-11-02 | 北京化工大学 | Method for preparing white carbon black hybridized material prepared by modification with end chlorosilane polymer |
| CN102229759B (en) * | 2011-05-06 | 2013-05-01 | 北京化工大学 | Method for preparing white carbon black hybridized material prepared by modification with end chlorosilane polymer |
| CN103980743A (en) * | 2014-05-12 | 2014-08-13 | 梁洪奎 | Method for producing a chemically modified carbon black |
| CN103980743B (en) * | 2014-05-12 | 2016-08-24 | 潍坊世纪阳光知识产权代理有限公司 | A kind of production method of chemical method modified carbon black |
| CN104193922A (en) * | 2014-09-02 | 2014-12-10 | 三明学院 | Water-based grafting modified carbon black and preparation method thereof |
| CN104193922B (en) * | 2014-09-02 | 2017-07-14 | 三明学院 | A kind of aqueous graft modification carbon black and preparation method thereof |
| CN108598482A (en) * | 2018-04-02 | 2018-09-28 | 合肥国轩高科动力能源有限公司 | A kind of carbon black modified water system SBR lithium ion battery binders and preparation method thereof |
| CN108467447A (en) * | 2018-04-03 | 2018-08-31 | 陕西科技大学 | A kind of graphene is modified NO free radical polymer material and preparation method thereof |
| CN113088133A (en) * | 2021-02-07 | 2021-07-09 | 纳琳威纳米科技南通有限公司 | High-blackness UV nano high-speed code spraying color paste and preparation method thereof |
| CN113462105A (en) * | 2021-05-31 | 2021-10-01 | 浙江科赛新材料科技有限公司 | Expanded polytetrafluoroethylene material and preparation method thereof |
| CN113999547A (en) * | 2021-11-20 | 2022-02-01 | 广东九彩新材料有限公司 | Preparation method of high-content carbon black master batch |
| CN116790139A (en) * | 2023-06-28 | 2023-09-22 | 安徽黑猫新材料有限公司 | Preparation method of grinding-free self-dispersing carbon black |
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