CN108102041A - A kind of Carbon nano-tube dispersant and preparation method thereof - Google Patents
A kind of Carbon nano-tube dispersant and preparation method thereof Download PDFInfo
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- CN108102041A CN108102041A CN201711391772.2A CN201711391772A CN108102041A CN 108102041 A CN108102041 A CN 108102041A CN 201711391772 A CN201711391772 A CN 201711391772A CN 108102041 A CN108102041 A CN 108102041A
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- 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
- C08F283/065—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals on to unsaturated polyethers, polyoxymethylenes or polyacetals
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- 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/01—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to unsaturated polyesters
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- 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/04—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polycarbonamides, polyesteramides or polyimides
- C08F283/045—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polycarbonamides, polyesteramides or polyimides on to unsaturated polycarbonamides, polyesteramides or polyimides
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Abstract
The invention discloses a kind of Carbon nano-tube dispersant and preparation method thereof, which is prepared by N vinyl pyrrolidones, unsaturated polymeric monomer A polymerizations.Carbon nano-tube dispersant disclosed by the invention has the advantages that good dispersion effect, good stability, preparation process be simple, structure-controllable, can be applied to the field of dispersions of carbon nanotubes, also acts as the dispersant, suspending agent, stabilizer of other field.
Description
Technical field
The present invention relates to field of carbon nanotubes, particularly a kind of dispersant for dispersing Nano carbon tubes；The present invention also relates to
And the preparation method of foregoing carbon nanotubes dispersant.
Background technology
Carbon nanotubes (CNTs) since 1991 find since, with its excellent chemical characteristic, mechanical property, hot property,
Optical property, electrical property etc. are constantly subjected to the extensive concern of scientific worker.But carbon nanotubes is tubular nanometer material, has pole
Big draw ratio and specific surface area, while there is stronger Van der Waals force between CNTs, make it that winding reunion etc. easily occur existing
As, therefore be difficult to disperse in the base, and then the serious performance for constraining product.Therefore, the superiority of CNTs has been given play to
Can, how uniformly and stably to disperse the critical problem that CNTs is urgent need to resolve.
It can change CNTs surface textures using acid with strong oxidizing property, other functional groups are accessed on its surface, it can be by surface
Chemical modification, enhance the compatibility of CNTs and decentralized medium, and then be conducive to obtain uniform and stable dispersion liquid.It but should
Method destroys the surface texture of CNTs, causes to be unable to ordered arrangement between tube wall, make its electric conductivity, electromagnetically, mechanical property
Deng significantly reducing.The method that non-covalent processing can be used in domestic and international lot of documents and patent report divides CNTs
It dissipates, i.e., using the dispersant of special construction and CNTs phase separations, realization aligns and Stable distritation, and enhancing CNTs is scattered
Dispersiveness in medium.As Shanghai Silicate Inst., Chinese Academy of Sciences CN 101773801A propose to disperse carbon with biomolecule
Nanotube can be achieved to disperse CNTs in the case of not destroying carbon nanometer tube structure, however such biology base dispersant
Complex production process, and be difficult to obtain, it is expensive.Southern Yangtze University CN 106587013A design a kind of switching mode and disperse
Agent can disperse CNTs in aqueous solution, but the dispersant needs to be passed through nitrogen, air or heat resolve in use,
Application method is complicated, and only disperses in aqueous solution, and application conditions relatively limit to.
The content of the invention
The purpose of the present invention is provide a kind of structure-controllable, cost economy in view of the deficiencies of the prior art and can stablize point
Dissipate the dispersant of CNTs.
It is another object of the present invention to provide the preparation methods of above-mentioned dispersant.
The purpose of the present invention is achieved through the following technical solutions：
A kind of Carbon nano-tube dispersant is prepared by n-vinyl pyrrolidone, unsaturated polymeric monomer A polymerizations,
Middle unsaturation polymeric monomer A general structures are as shown in formula I：
Wherein, R1For H or C1-C4Alkyl；W is-CH2-、-CH2CH2-、-CH2CH2CH2-、 -OCH2CH2CH2CH2-
OrGroup；The integer that X is O or NH, n are 1-100；Z for H, alkoxy orR2For C1-C20's
Alkyl；
Y is polyethers, polyester or polyamide, and general structure is respectively as shown in formula II, III, IV：
Wherein, k and m is the integer of 0-100, and is 0 during k with m differences；R3、R4、R5、R6、R7And R8For C1-C18Alkylene
Base, C1-C24Aryl or aryl alkylene；P, q, s and t are the integer of 1-100；
Unsaturated polymeric monomer A is the one or more combination of each structure in structure shown in formula I general formula；
Monomer A and the molar ratio of unsaturated polymeric monomer A are 1:1~30:1.
A kind of Carbon nano-tube dispersant, Y polyether structures are preferable over polyoxyethylene ether, polyethenoxy ether, polyoxy second
The one or more of alkene polyethenoxy ether.
A kind of Carbon nano-tube dispersant, Y polyester constructions be preferable over polyethyleneglycol adipate, polytetramethylene glycol oneself two
Acid esters, poly- hexylene glycol succinate, Polyethylene Terephthalates, makrolon, polycaprolactone, poly- 12- hydroxy stearic acid esters
One or more.
A kind of Carbon nano-tube dispersant, Y polyamide structures are preferable over PA 66, polyadipate fourth two
Amine, poly-succinic hexamethylene diamine, poly- terephthalic acids hexamethylene diamine, polycaprolactam, one kind or several of poly- terephthalate p-phenylenediamine
Kind.
A kind of Carbon nano-tube dispersant, unsaturated polymeric monomer A may be selected from one kind in polyethers, polyester, polyamide
It is or several.
A kind of Carbon nano-tube dispersant, weight average molecular weight 10000-1000000.
The preparation method of the Carbon nano-tube dispersant, is as follows：
(1) initiator is dissolved in solvent, mixed solution F is made；
(2) n-vinyl pyrrolidone, unsaturated polymeric monomer A, chain-transferring agent are dissolved in solvent, mixed solution G is made；
(3) mixed solution G is added drop-wise in mixed solution F under conditions of oil bath perseverance gentle agitation, reaction temperature is
40-120 DEG C, when time for adding is 0.5-5 small；
(4) be added dropwise completely follow-up continuation of insurance temperature 0.5-3 it is small when, make that the reaction was complete.
The solvent is water, ethyl alcohol, tetrahydrofuran, dioxane, dimethyl sulfoxide (DMSO), N,N-dimethylformamide, N, N bis-
Methylacetamide, dimethylbenzene, toluene, the one or more combination of N-Methyl pyrrolidone.
The initiator is azodiisobutyronitrile, azobisisoheptonitrile, dibenzoyl peroxide, persulfate, hydrogen peroxide
One or more of combination, initiator be monomer gross mass 0.3%-2.5%.
The chain-transferring agent is mercaptoethanol, thioacetic acid, mercaptopropionic acid, lauryl mercaptan, hexadecyl mercaptan, ten
One or more of eight alkyl hydrosulfides, thioglycollic acid-2-ethyl hexyl ester, isooctyl thioglycolate or isooctyl mercaptopropionate,
Chain tra nsfer dosage is the 0.2%-4.0% of monomer gross mass..
The beneficial effects of the invention are as follows：
The present invention designs the combed dispersant using polyethers, polyester or polyamide as solvent chain, and is applied to
The field of dispersions of CNTs has the advantages that dispersion effect is good, preparation process is simple, structure-controllable.
Compared with polyvinylpyrrolidone homopolymer, the solvent chain that dispersant of the invention carries can play space bit
Repulsive interaction is hindered, enhances the stability of CNTs slurries so that slurry has longer storage time.Also, point of the present invention
Powder structure-controllable can optimize its structure according to practical application condition, improve the dispersion stabilization of CNTs.
Specific embodiment
With reference to embodiment, the present invention is described in further detail, but the implementation of the present invention is not limited to this.
Monomer structure is as follows used in embodiment：
Embodiment 1
Weigh 1.2g azodiisobutyronitriles and be dissolved in 60g tetrahydrofurans and mixed solution F is made, weigh 108.6g A1,
11.1g N- vinyl pyrrolidones, 1.2g isooctyl thioglycolates, which are dissolved in 60g tetrahydrofurans, is made mixed solution G, 80
DEG C and stirring under conditions of mixed solution G is added drop-wise in mixed solution F, time for adding for 2 it is small when；It is protected after being added dropwise completely
Dispersant is made when small in temperature 1.
Embodiment 2
It weighs 0.8g dibenzoyl peroxides and is dissolved in 82gN- methyl pyrrolidones obtained mixed solution F, weigh 108.6g
A2,55.5g n-vinyl pyrrolidone, 0.5g isooctyl thioglycolates, which are dissolved in 82gN- methyl pyrrolidones, is made mixing
Solution G is added drop-wise at 100 DEG C and under conditions of stirring by mixed solution G in mixed solution F, when time for adding is 1 small；It waits to drip
Dispersant is made when heat preservation 3 is small after adding entirely.
Embodiment 3
It weighs 2.4g dibenzoyl peroxides and is dissolved in 79gN- methyl pyrrolidones obtained mixed solution F, weigh 101.8g
It is molten that A3,55.5g n-vinyl pyrrolidone, 3.1g lauryl mercaptans are dissolved in 79gN- methyl pyrrolidones obtained mixing
Liquid G is added drop-wise at 100 DEG C and under conditions of stirring by mixed solution G in mixed solution F, when time for adding is 4 small；It waits to be added dropwise
Dispersant is made when heat preservation 0.5 is small after completely.
Embodiment 4
It weighs 3.4g azodiisobutyronitriles and is dissolved in 69gN- methyl pyrrolidones obtained mixed solution F, weigh 108.7g
A4,27.8g n-vinyl pyrrolidone, 5.5g lauryl mercaptans, which are dissolved in 69gN- methyl pyrrolidones, is made mixed solution
G is added drop-wise at 120 DEG C and under conditions of stirring by mixed solution G in mixed solution F, when time for adding is 2 small；It waits to drip
Dispersant is made when heat preservation 2 is small after complete.
Embodiment 5
It weighs 2.4g potassium peroxydisulfates and is dissolved in 81g water obtained mixed solution F, weigh 106.8g A5,55.5g N- vinyl
Pyrrolidones, 3.2g mercaptoethanols, which are dissolved in 81g water, is made mixed solution G, by mixed solution under conditions of 40 DEG C with stirring
G is added drop-wise in mixed solution F, when time for adding is 1 small；Dispersant is made when heat preservation 1 is small after being added dropwise completely.
Embodiment 6
It weighs 1.7g potassium peroxydisulfates and is dissolved in 106g water obtained mixed solution F, weigh 156.6g A6,55.5g N- ethylene
Base pyrrolidones, 3.2g thioacetic acid, which are dissolved in 106g water, is made mixed solution G, will mixing at 60 DEG C and under conditions of stirring
Solution G is added drop-wise in mixed solution F, when time for adding is 1.5 small；Dispersant is made when heat preservation 1.5 is small after being added dropwise completely.
Embodiment 7
It weighs 2.8g hydrogen peroxide and is dissolved in 70g water obtained mixed solution F, weigh 83.7g A7,55.5g N- vinylpyridines
Pyrrolidone, 3.5g mercaptopropionic acids, which are dissolved in 70g water, is made mixed solution G, by mixed solution G under conditions of 80 DEG C with stirring
It is added drop-wise in mixed solution F, when time for adding is 0.5 small；Dispersant is made when heat preservation 2 is small after being added dropwise completely.
Embodiment 8
It weighs 1.3g azodiisobutyronitriles and is dissolved in 56g dioxane obtained mixed solution F, weigh 13.7g A1,41.9g
It is molten that A8,55.5g n-vinyl pyrrolidone, 3.3g thioglycollic acid-2-ethyl hexyl esters are dissolved in 56g dioxane obtained mixing
Liquid G is added drop-wise at 80 DEG C and under conditions of stirring by mixed solution G in mixed solution F, when time for adding is 3 small；It waits to be added dropwise
Dispersant is made when heat preservation 1 is small after completely.
Embodiment 9
It weighs 1.4g dibenzoyl peroxides and is dissolved in 69gN, mixed solution F is made in dinethylformamide, weighs
17.8g A1,35.6g A5,83.3g n-vinyl pyrrolidone, 2.7g hexadecyl mercaptans are dissolved in 69gN, N- dimethyl methyls
Mixed solution G is made in amide, is added drop-wise at 80 DEG C and under conditions of stirring by mixed solution G in mixed solution F, during dropwise addition
Between for 2 it is small when；Dispersant is made when heat preservation 1 is small after being added dropwise completely.
Embodiment 10
Weigh 1.6g dibenzoyl peroxides and be dissolved in 81g dimethyl sulfoxide (DMSO)s and mixed solution F is made, weigh 15.8g A1,
31.6g A4,31.0g A5,83.3g n-vinyl pyrrolidone, 1.6g hexadecyl mercaptans are dissolved in 81g dimethyl sulfoxide (DMSO)s
Mixed solution G is made, is added drop-wise at 90 DEG C and under conditions of stirring by mixed solution G in mixed solution F, time for adding 1.5
Hour；Dispersant is made when heat preservation 1.5 is small after being added dropwise completely.
Applicating evaluating：
Dispersant prepared by the dispersant and patent CN 103087554A embodiments 3 prepared using Examples 1 to 10 is to carbon
Nanotube is disperseed, and process for dispersing is as follows：By 10g carbon nanotubes, 10g dispersants, 1000g N-Methyl pyrrolidones first exist
It is added to after high speed dispersion is uniform under 2000rpm in the resistance to nano-dispersed machines of speeding of 500ml, when 25 DEG C of grindings 6 are small, after prepared by slurry
Malvern particle instrument and viscosimeter is respectively adopted to test the grain size and viscosity of dispersed paste, evaluation result such as 1 institute of table
Show：
1. carbon nanotubes dispersed paste evaluation result of table
As can be seen from Table 1, the viscosity of the grain size of carbon nanotubes and slurry be less than comparative example, and stand 72 it is small when,
Each embodiment is homogeneous solution, and comparative example bottom slightly has sediment, illustrates that dispersant of the embodiment of the present invention has carbon nanotubes
There are preferable dispersion effect, function admirable.
Claims (9)
1. a kind of Carbon nano-tube dispersant, which is characterized in that the dispersant is by n-vinyl pyrrolidone, unsaturated polymeric monomer A
Polymerization prepares, wherein, unsaturated polymeric monomer A has structure shown in formula I general formula：
Wherein, R1For H or C1-C4Alkyl；W is-CH2-、-CH2CH2-、-CH2CH2CH2-、-OCH2CH2CH2CH2- orGroup；X is O or NH；N is the integer of 1-100；Z for H, alkoxy orR2For C1-C20Alkyl；
Y is polyethers, polyester or polyamide, and general structure is respectively as shown in formula II, III, IV：
Wherein, k and m is the integer of 0-100, and is 0 during k with m differences；R3、R4、R5、R6、R7And R8For C1-C18Alkylidene, C1-
C24Aryl or aryl alkylene；P, q, s and t are the integer of 1-100；
Unsaturated polymeric monomer A is the one or more combination of each structure in structure shown in formula I general formula；
N-vinyl pyrrolidone and the molar ratio of unsaturated polymeric monomer A are 1~30:1.
2. a kind of Carbon nano-tube dispersant according to claim 1, which is characterized in that the Y is polyether structure, is selected poly-
Ethylene oxide ether, polyethenoxy ether, the one or more of polyoxyethylene poly-oxygen propylene aether.
3. a kind of Carbon nano-tube dispersant according to claim 1, which is characterized in that the Y is polyester construction, is selected poly-
Glycol adipate, polytetramethylene glycol adipate ester, poly- hexylene glycol succinate, Polyethylene Terephthalates, makrolon,
The one or more of polycaprolactone, poly- 12- hydroxy stearic acid esters.
4. a kind of Carbon nano-tube dispersant according to claim 1, which is characterized in that Y is polyamide structure, selects and gathers oneself
It is diacid hexamethylene diamine, polyadipate butanediamine, poly-succinic hexamethylene diamine, poly- terephthalic acids hexamethylene diamine, polycaprolactam, poly- to benzene two
The one or more of acyl p-phenylenediamine.
A kind of 5. Carbon nano-tube dispersant according to claim 1, it is characterised in that Carbon nano-tube dispersant Weight-average molecular
It measures as 10000-1000000.
6. the preparation method of Carbon nano-tube dispersant described in a kind of claim 1, which is characterized in that the preparation method includes following
Specific steps：
(1) initiator is dissolved in solvent, mixed solution F is made；
(2) n-vinyl pyrrolidone, unsaturated polymeric monomer A, chain-transferring agent are dissolved in solvent, mixed solution G is made；
(3) mixed solution G being instilled in mixed solution F under conditions of oil bath perseverance gentle agitation, reaction temperature is 40-120 DEG C,
When time for adding is 0.5-5 small；
(4) be added dropwise completely follow-up continuation of insurance temperature 0.5-3 it is small when, make that the reaction was complete, the obtained Carbon nano-tube dispersant；Wherein：
Unsaturated polymeric monomer A has structure shown in formula I general formula：
Wherein, R1For H or C1-C4Alkyl；W is-CH2-、-CH2CH2-、-CH2CH2CH2-、-OCH2CH2CH2CH2- or base
Group；X is O or NH；N is the integer of 1-100；Z for H, alkoxy or；R2For C1-C20 alkyl；
Y is polyethers, polyester or polyamide, and general structure is respectively as shown in formula II, III, IV：
Wherein, k and m is the integer of 0-100, and is 0 during k with m differences；R3、R4、R5、R6、R7And R8For C1-C18Alkylidene, C1-
C24Aryl or aryl alkylene；P, q, s and t are the integer of 1-100；
Unsaturated polymeric monomer A is the one or more combination of each structure in structure shown in formula I general formula；
N-vinyl pyrrolidone and the molar ratio of unsaturated polymeric monomer A are 1~30:1.
7. the preparation method of Carbon nano-tube dispersant according to claim 6, it is characterised in that：The solvent is water, second
Alcohol, tetrahydrofuran, dioxane, dimethyl sulfoxide (DMSO), N,N-dimethylformamide, N, N dimethyl acetamide, dimethylbenzene, toluene,
The one or more combination of N-Methyl pyrrolidone.
8. the preparation method of Carbon nano-tube dispersant according to claim 6, it is characterised in that：The initiator is azo
The combination of one or more of bis-isobutyronitrile, azobisisoheptonitrile, dibenzoyl peroxide, persulfate, hydrogen peroxide, initiator
For the 0.3%-2.5% of monomer gross mass.
9. the preparation method of Carbon nano-tube dispersant according to claim 6, it is characterised in that：The chain-transferring agent is mercapto
Base ethyl alcohol, thioacetic acid, mercaptopropionic acid, lauryl mercaptan, hexadecyl mercaptan, Stearyl mercaptan, thioacetic acid -2- second
One or more of the own ester of base, isooctyl thioglycolate or isooctyl mercaptopropionate, chain-transferring agent dosage are monomer gross mass
0.2%-4.0%.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109455696A (en) * | 2018-10-24 | 2019-03-12 | 苏州世名科技股份有限公司 | A kind of aqueous carbon nano tube paste and preparation method thereof |
| CN110437373A (en) * | 2018-05-03 | 2019-11-12 | 史增谦 | Carbon nano-tube dispersant and its preparation method and application |
| CN115322293A (en) * | 2022-05-26 | 2022-11-11 | 世名(苏州)新材料研究院有限公司 | Dispersing agent, preparation method and application of dispersing agent in preparation of carbon nano tube dispersion liquid |
| CN115975126A (en) * | 2022-12-26 | 2023-04-18 | 上海宇昂水性新材料科技股份有限公司 | Comb-type polymer and preparation method and application thereof |
| WO2024139144A1 (en) * | 2022-12-31 | 2024-07-04 | 上海宇昂水性新材料科技股份有限公司 | Pvp comb copolymer and preparation method therefor and use thereof |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109455696A (en) * | 2018-10-24 | 2019-03-12 | 苏州世名科技股份有限公司 | A kind of aqueous carbon nano tube paste and preparation method thereof |
| CN115322293A (en) * | 2022-05-26 | 2022-11-11 | 世名(苏州)新材料研究院有限公司 | Dispersing agent, preparation method and application of dispersing agent in preparation of carbon nano tube dispersion liquid |
| CN115322293B (en) * | 2022-05-26 | 2024-03-15 | 世名(苏州)新材料研究院有限公司 | Dispersing agent, preparation method and application thereof in preparation of carbon nanotube dispersion liquid |
| CN115975126A (en) * | 2022-12-26 | 2023-04-18 | 上海宇昂水性新材料科技股份有限公司 | Comb-type polymer and preparation method and application thereof |
| WO2024139144A1 (en) * | 2022-12-31 | 2024-07-04 | 上海宇昂水性新材料科技股份有限公司 | Pvp comb copolymer and preparation method therefor and use thereof |
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