CN113150209B - High molecular weight hydrophilic zwitterionic antistatic agent and preparation method and application thereof - Google Patents
High molecular weight hydrophilic zwitterionic antistatic agent and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a high molecular weight hydrophilic zwitterionic antistatic agent, a preparation method and application thereof. Compared with conductive fillers and anionic or cationic polymer antistatic agents, the hydrophilic zwitterionic antistatic agent prepared by the invention has the following characteristics: the surface resistivity is low and can reach 10 7 Omega; the compatibility with high polymer materials is good; the antistatic property is durable; less influence on mechanical properties and the like.
Description
Technical Field
The invention belongs to the field of new material chemical synthesis, and relates to a high molecular weight hydrophilic zwitterionic antistatic agent, and a preparation method and application thereof.
Background
The high molecular materials are generally combined through stable covalent bonds and cannot be ionized, so that large forbidden band energy levels exist among molecular chains to prevent carriers from moving, and the surface resistivity of the high molecular materials is high and is generally 10 12 ～10 15 Between omega, when used as a non-insulating material, the surface of the material is easy to generate static electricity through friction, and is difficult to eliminate, so that the phenomena of dust absorption, electronic device breakdown, discharge, combustion and the like are easy to cause, and serious potential safety hazards exist. The method of adding an antistatic agent to a thermoplastic elastomer to avoid such problems has been widely used because it is relatively simple and effective.
The action mechanism of the antistatic agent is mainly as follows: (1) ionic antistatic agents increase the ionic concentration at the surface of the article, thereby increasing conductivity. (2) The hydrophilic group of the antistatic agent increases the moisture absorption of the surface of the article to form a conductive film. (3) The antistatic agent having a large dielectric constant can increase the dielectric properties of the gap between the friction bodies. (4) Increasing the smoothness of the article surface can reduce its friction factor. The compatibility of the antistatic agent with the polymer material has a great influence on the antistatic property of the polymer material. The compatibility of the antistatic agent and the antistatic agent is very good, molecules of the antistatic agent are difficult to migrate, the antistatic agent lost on the surface of the material cannot be timely supplemented, and the function is difficult to play; and the compatibility is too poor, the antistatic agent can be greatly separated out, the appearance of the product is influenced, and the antistatic effect is difficult to last. The addition of the antistatic agent has great influence on the antistatic performance of the material, and when the antistatic agent reaches a certain critical concentration, a plurality of conductive molecular layers are formed on the surface of a product, so that a good antistatic effect is achieved.
The antistatic agents commonly used in the market are mainly classified into two types, i.e., surfactant type antistatic agents and permanent antistatic agents. Surfactants antistatic agents generally contain both lipophilic and hydrophilic groups. The lipophilic groups are usually saturated long carbon chains and the hydrophilic groups are usually hydroxyl, carboxyl, sulfonic and ether linkages. According to the ionization condition of the hydrophilic group, the surfactant type antistatic agent can be classified into a cationic antistatic agent, an anionic antistatic agent, a zwitterionic antistatic agent and a nonionic antistatic agent. The anionic antistatic agent mainly comprises alkyl sulfonate and phosphate compounds, and has poor compatibility with materials; the cationic antistatic agent has good antistatic property, strong adhesive force to the surface of a high polymer material, but poor thermal stability, and solution discoloration under the high-temperature processing condition, so the cationic antistatic agent is often used as an external coating type antistatic agent; the amphoteric antistatic agent has the most outstanding characteristics of having the functions of a cationic active agent and an anionic active agent under certain conditions, having better compatibility with materials, and having antistatic performance similar to that of a cationic type, but the general amphoteric antistatic agent is prepared by adopting an anionic and cationic copolymerization method, molecules cannot reach electric neutrality and have charges, and the agglomeration and dispersion of the antistatic agent are uneven when the macromolecule physical modification is carried out. The nonionic antistatic agent has no charge, and cannot leak the charge, so the antistatic performance is not higher than that of the ionic antistatic agent, but the nonionic antistatic agent has low toxicity, good thermal stability and low corrosivity, and is not easy to cause the aging of high polymer materials. The permanent antistatic agent is a hydrophilic polymer with large relative molecular mass, and has good compatibility with matrix resin, thereby having good stability and durability. Their dispersibility in polymeric matrix resins has a significant effect on their antistatic properties. The hydrophilic polymer is in a layered dispersed structure on the surface of the matrix polymer material, and the central part is in a spherical distribution, which is called as a core-shell structure. The dispersed structure can effectively reduce the surface resistivity of the blend, has permanent antistatic performance, does not influence the thermal performance and mechanical performance of the material, and basically adopts anion-cation copolymerization or the combination of anion and cation antistatic agents, so that the aggregation phenomenon of electrostatic adsorption can occur.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides the high molecular weight hydrophilic zwitterionic antistatic agent, and the antistatic agent can improve the compatibility of the antistatic agent and a high molecular material by introducing long carbon chains and increasing the molecular weight of the antistatic agent, so that the surface resistivity of the high molecular material is greatly reduced, and the precipitation of the antistatic agent is reduced.
In order to achieve the above technical objects, the present invention provides the following technical solutions.
A high molecular weight hydrophilic zwitterionic antistatic agent has the following structural formula:
wherein x and y are structural unit percentages, z is the number of carbon atoms, x is 60-95%, y is 5-40%, and z is ≧ 10.
As shown in the structure, the anions and cations of the antistatic agent are uniformly distributed on the same side chain, the molecules are electrically neutral and hardly agglomerate, and the antistatic agent has the advantages of various types of antistatic agents.
Preferably, the high molecular weight hydrophilic zwitterionic antistatic agent has a weight average molecular weight
Is 1.0X 10 4 ～8.0 ×10 4 。
Another object of the present invention is to provide a method for preparing the above high molecular weight hydrophilic zwitterionic antistatic agent, which comprises a two-step synthesis process, wherein the first step is to synthesize amphoteric monomer (2-methacryloyloxy) ethyl dimethyl alkyl acid ammonium bromide, the second step is to use potassium iodide as a catalyst for synthesizing antistatic agent monomer, and acrylamide as one of copolymerization components of the antistatic agent, and the copolymerization is carried out with amphoteric monomer. By introducing the zwitterionic monomer into the hydrophilic polyacrylamide, the antistatic agent endows the high molecular material with anionic or cationic antistatic agent performance under different use conditions, and can be compounded and combined with the anionic or cationic antistatic agent for use.
The preparation method of the high molecular weight hydrophilic zwitterionic antistatic agent comprises the following raw materials in parts by weight:
the chemical formula of the alkyl bromide acid is Br (CH) 2 ) Z COOH，z≧10。
Preferably, the mass ratio of the dimethylaminoethyl methacrylate to the alkyl bromide acid is 1.
Preferably, potassium iodide is 0.05 parts.
Preferably, the water-soluble azo initiator is one of azobisisobutylimidazoline hydrochloride (VA-044 initiator), azobisisobutylamidine hydrochloride (V-50 initiator) and azobiscyanovaleric acid (V-501 initiator).
Preferably, the emulsifier is one or more of sodium dodecyl sulfate, cetyl trimethyl ammonium bromide and alkylphenol polyoxyethylene.
Preferably, the preparation method of the high molecular weight hydrophilic zwitterionic antistatic agent comprises the following steps:
(1) Adding dimethylaminoethyl methacrylate and alkyl bromide acid into a reactor according to a certain proportion, adding absolute ethyl alcohol and potassium iodide, and introducing nitrogen into the reactor to remove oxygen;
(2) Under the protection of nitrogen, performing constant-temperature water bath at 50-70 ℃ and magnetic stirring reaction for 24-72 h;
(3) Filtering and drying the product obtained in the step (2), adding water to dissolve the dried crude product, extracting with diethyl ether, and freeze-drying the obtained water phase to obtain amphoteric monomer (2-methacryloyloxy) ethyl dimethyl alkyl acid ammonium bromide;
(5) Weighing the amphoteric monomer, the acrylamide and the emulsifier according to a proportion, adding distilled water, stirring to completely dissolve the amphoteric monomer, introducing nitrogen at room temperature to remove oxygen, adding a water-soluble azo initiator, and continuously introducing nitrogen to remove oxygen; carrying out constant-temperature water bath reaction at the temperature of 40-80 ℃ for 24-48 h;
(5) And (3) immersing the product in acetone to remove unreacted monomers, then performing vacuum drying, crushing and grinding into powder to obtain the hydrophilic zwitterionic antistatic agent.
Preferably, the reaction temperature in step (4) is 50 ℃ to 70 ℃. This is most advantageous for the water-soluble azo type initiator to function. The initiator is cheap, and is easy to react to generate linear molecules, so that the branching reaction is reduced, and the molecular weight is improved. While other types of initiators, like organic peroxy-type initiators, redox-type initiators, either use too high temperatures or undergo branching reactions leading to lower molecular weights.
Preferably, the ammonium bromide (2-methacryloyloxy) ethyl dimethylalkylate has the following structural formula:
wherein z ≧ 10.
Use of a high molecular weight hydrophilic zwitterionic antistatic agent as described in any one of the preceding claims in an antistatic material.
Compared with the prior art, the invention has the following beneficial effects:
the invention prepares the antistatic agent with polyacrylamide as the main chain by molecular structure design and an emulsion polymerization method, has good hydrophilicity and large relative molecular mass, can improve the compatibility of the antistatic agent and a high polymer material by introducing long carbon chains and increasing the molecular weight of the antistatic agent, greatly reduces the surface resistivity of the high polymer material, reduces the precipitation of the antistatic agent, improves the durability of the antistatic effect, has excellent antistatic performance, and can be used as the antistatic agent or the antistatic material. The hydrophilic main chain has strong hygroscopicity and permanent antistatic property, and has good antistatic property no matter in dry or humid environment, and the defects of poor durability, large dependence on air humidity, delayed effect and the like of a surfactant antistatic agent are overcome.
In the preparation process, each pair of anions and cations are positioned on one side chain, so that the number of the anions and the number of the cations in the antistatic agent molecules are completely equal and are electrically neutral, the aggregation is not easy to occur in the processing process, the molecular weight is large, and the antistatic effect is durable; the invention takes water as a medium, avoids the troubles of using expensive solvents and recovering the solvents and has environmental protection property; the method is simple to operate, easy for large-scale production and wide in market prospect.
The antistatic agent has good compatibility with polymer materials, forms a more stable network structure in polymers, has better antistatic effect, and is a novel functional material with promising development prospect. In addition, the carbon-carbon long chain and the rubber-based molecular chain of the elastomer are mutually entangled, so that the elastomer has good compatibility; the hydrophilic polymer can release charges on the surface of the material and also can release charges inside the material, so that the surface resistance and the volume resistance of the material can be simultaneously reduced.
Detailed Description
The present invention will be described in further detail with reference to the following examples. This should not be understood as limiting the scope of the above-described subject matter of the present invention to the following examples. All the technologies realized based on the above contents of the present invention belong to the scope of the present invention.
The invention provides a high molecular weight hydrophilic zwitterionic antistatic agent which is formed by the following components in parts by weight:
the alkyl bromide acid is Br (CH) 2 ) Z COOH，z≧10。
The preparation method of the high molecular weight hydrophilic zwitterionic antistatic agent comprises the following steps:
adding dimethylaminoethyl methacrylate and alkyl bromide acid into a three-neck flask, using absolute ethyl alcohol as a solvent and potassium iodide as a catalyst. And introducing nitrogen into the three-neck flask to remove oxygen, wherein the time for introducing the nitrogen can be adjusted according to needs, and the time is selected to be 30min. Under the protection of nitrogen, performing constant-temperature water bath at 50-70 ℃ and performing magnetic stirring reaction for 24-72 h. The product solution was filtered and the crude product was dried. The dried crude product was dissolved in water, extracted with diethyl ether, and the resulting aqueous phase was freeze-dried to give an amphoteric monomer white powder, ammonium (2-methacryloyloxy) ethyl dimethyl alkanoate bromide having the structure shown below:
wherein z is ≧ 10;
weighing an amphoteric monomer (2-methacryloyloxy) ethyl dimethyl alkyl acid ammonium bromide, acrylamide and an emulsifier, placing the amphoteric monomer, the acrylamide and the emulsifier in a three-neck flask filled with distilled water, stirring to completely dissolve the amphoteric monomer, introducing nitrogen at room temperature, carrying out bubbling to remove oxygen, and adjusting the time of introducing the nitrogen according to needs, wherein the selection time is 30min; adding water-soluble azo initiator and continuously introducing nitrogen. Heating to 40-80 ℃, and placing in a constant-temperature water bath for reaction for 24-80 h. The obtained product is immersed in acetone to remove unreacted monomers, and then is dried in vacuum, crushed and ground into powder, so that the hydrophilic zwitterionic antistatic agent is obtained, and the structural formula of the hydrophilic zwitterionic antistatic agent is as follows:
wherein x and y are structural unit percentages, z is the number of carbon atoms, x is 60-95%, y is 5-40%, and z is ≧ 10.
The high molecular weight hydrophilic zwitterionic antistatic agent prepared according to the above method has a weight average molecular weight
Is 1.0X 10 4 ～ 8.0×10 4 。
Through molecular structure design, the invention synthesizes amphoteric monomer (2-methacryloyloxy) ethyl dimethyl alkyl acid ammonium bromide by taking dimethylaminoethyl methacrylate and alkyl bromide acid as raw materials, takes a water-soluble azo initiator as an initiator for synthesizing an antistatic agent monomer, and adopts an emulsion method to carry out free radical copolymerization on the amphoteric monomer and acrylamide to prepare the high molecular weight hydrophilic amphoteric ionic antistatic agent. Because the anions and the cations are positioned on one monomer, the number of the anions and the cations in the antistatic agent molecule is completely equal and is electrically neutral, the aggregation is not easy to occur in the processing process, the molecular weight is large, and the antistatic effect is durable.
In general, an anionic monomer and a cationic monomer are copolymerized, the number of positive and negative charges introduced into a molecule is random, and the whole molecule is charged and agglomerated. The invention introduces alkyl bromide acid, can provide long carbon chain and anion group at the same time, make each pair of anion and cation in the antistatic agent molecule in the same side chain, the positive and negative charge number is completely equal, cause the whole molecule to present the electrical neutrality, avoid taking place the agglomeration problem that the electrostatic adsorption causes in the subsequent use.
In the present invention, the ratio of the amount of dimethylaminoethyl methacrylate to the amount of alkyl bromide acid is preferably 1.1-1.4, which enables the dimethylaminoethyl methacrylate to react completely.
The invention takes acrylamide as a main chain, so that the antistatic agent has good hydrophilic performance, the hydrophilic main chain has strong hygroscopicity and permanent antistatic property, and the antistatic property is good no matter in a dry or wet environment.
In the invention, the initiator added in the reaction is a water-soluble azo initiator, and in the embodiment, the initiator is preferably one of azobisisobutylimidazoline hydrochloride (VA-044 initiator), azobisisobutylamidine hydrochloride (V-50 initiator) and azobiscyanovaleric acid (V-501 initiator). The initiator is easy to react to generate linear molecules, and the branching reaction is reduced, so that the molecular weight is improved, and the whole reaction takes water as a medium, thereby avoiding the troubles of using expensive solvents and recovering the solvents and having environmental protection.
The emulsifier is one or more of sodium dodecyl sulfate, cetyl trimethyl ammonium bromide and alkylphenol polyoxyethylene.
The reaction temperature after the initiator is added is controlled between 50 and 70 ℃, and the water-soluble azo initiator is most beneficial to play a role at the temperature.
The performance test method of the antistatic agent prepared by the method comprises the following steps: taking the weight ratio of 8:100 of the hydrophilic zwitterionic antistatic agent provided by the invention and TPV with the hardness of 87A produced by Nanjing Polylon science and technology Co., ltd are subjected to melt blending to prepare samples, the samples are injection-molded into sample pieces with the thickness of 90mm multiplied by 2mm, and the antistatic performance, the mechanical performance and the antistatic performance after washing for 4 weeks (once washing per week, and the resistance is measured after natural drying).
In order to further illustrate the present invention, the following will describe in detail the antistatic agent provided by the present invention and the preparation method thereof with reference to examples.
Example 1
A high molecular weight hydrophilic zwitterionic antistatic agent comprises the following raw materials in parts by weight:
amphoteric sheetThe temperature of the bulk synthesis is 50 ℃, and the reaction time is 48h; the synthesis temperature of the antistatic agent is 50 ℃, and the reaction time is 72h. The molecular weight of the antistatic agent obtained by GPC was 7X 10 4 。
Example 2
A high molecular weight hydrophilic zwitterionic antistatic agent comprises the following raw materials in parts by weight:
the synthesis temperature of the amphoteric monomer is 60 ℃, and the reaction time is 48h; the synthesis temperature of the antistatic agent is 70 ℃, and the reaction time is 24h. The molecular weight of the antistatic agent obtained is 4X 10 by GPC 4 。
Example 3
A high molecular weight hydrophilic zwitterionic antistatic agent comprises the following raw materials in parts by weight:
the synthesis temperature of the amphoteric monomer is 60 ℃, and the reaction time is 72 hours; the synthesis temperature of the antistatic agent is 60 ℃, and the reaction time is 72 hours. The molecular weight of the antistatic agent obtained is 3X 10 by GPC 4 。
Example 4
A high molecular weight hydrophilic zwitterionic antistatic agent comprises the following raw materials in parts by weight:
the synthesis temperature of the amphoteric monomer is 60 ℃, and the reaction time is 72h; the synthesis temperature of the antistatic agent is 60 ℃, and the reaction time is 72h. Prepared by GPC measurementThe molecular weight of the antistatic agent is 2X 10 4 。
Example 5
A high molecular weight hydrophilic zwitterionic antistatic agent comprises the following raw materials in parts by weight:
the synthesis temperature of the amphoteric monomer is 60 ℃, and the reaction time is 72 hours; the synthesis temperature of the antistatic agent is 50 ℃, and the reaction time is 72 hours. The molecular weight of the antistatic agent obtained by GPC was 4.5X 10 4 。
Example 6
A high molecular weight hydrophilic zwitterionic antistatic agent comprises the following raw materials in parts by weight:
the synthesis temperature of the amphoteric monomer is 60 ℃, and the reaction time is 72 hours; the synthesis temperature of the antistatic agent is 50 ℃, and the reaction time is 72 hours.
The antistatic agent has a molecular weight of 5X 10 as determined by GPC 4 。
The performance data of the antistatic TPV and of the pure TPV of examples 1 to 6 are shown in the following tables:
remarking: the samples were tested after being left at 23 ℃ for 24 hours, with the test environment being 23 ℃ and 50% RH.
From the above examples, it is clear that the antistatic property of the present invention is excellent and the antistatic effect is durable. The antistatic agent has large molecular weight, has enough chain length to be tangled with rubber molecular chains when being blended with TPV elastomer, and is not easy to run off when being washed by water; and the longer the side chain, the longer the lipophilic carbon chain, the better the compatibility with TPV, and the slower the migration speed. However, excessive addition of the amphoteric monomer results in a significant decrease in mechanical properties and a reduction in antistatic effect.
In addition, the antistatic agent has good compatibility with a high polymer material through long-time molecule precipitation and test piece blooming.
In conclusion, compared with the conductive filler and the anionic or cationic polymer antistatic agent, the hydrophilic zwitterionic antistatic agent prepared by the invention has low surface resistivity which can reach 10 7 Omega; the compatibility with high polymer materials is good; the antistatic property is durable; has little influence on the mechanical property.
Although the present invention has been described with reference to the preferred embodiments, it is not intended to be limited thereto. Those skilled in the art can make various changes and modifications without departing from the spirit and scope of the invention. Therefore, the protection scope of the present invention should be determined by the appended claims.
Claims (7)
1. A high molecular weight hydrophilic zwitterionic antistatic agent is characterized in that,
the weight average molecular weight of the antistatic agent is 1.0 multiplied by 10 4 ～8.0×10 4 ；
The used raw materials comprise the following components in parts by weight:
the chemical formula of the alkyl bromide acid is Br (CH) 2 ) Z COOH，z≧10；
The preparation method comprises the following steps:
(1) Adding dimethylaminoethyl methacrylate and alkyl bromide acid into a reactor according to a certain proportion, adding absolute ethyl alcohol and potassium iodide, and introducing nitrogen into the reactor to remove oxygen;
(2) Under the protection of nitrogen, performing constant-temperature water bath at 50-70 ℃ and magnetically stirring for reaction for 24-72 h;
(3) Filtering and drying the product obtained in the step (2), adding water to dissolve the dried crude product, extracting with diethyl ether, and freeze-drying the obtained water phase to obtain amphoteric monomer (2-methacryloyloxy) ethyl dimethyl alkyl acid ammonium bromide;
(4) Weighing the amphoteric monomer, the acrylamide and the emulsifier according to a proportion, adding distilled water, stirring to completely dissolve the amphoteric monomer, introducing nitrogen at room temperature to remove oxygen, adding a water-soluble azo initiator, and continuously introducing nitrogen to remove oxygen; carrying out constant-temperature water bath reaction at the temperature of 40-80 ℃ for 24-48 h;
(5) And immersing the product in acetone to remove unreacted monomers, then drying in vacuum, crushing and grinding into powder to obtain the hydrophilic zwitterionic antistatic agent.
2. The high molecular weight hydrophilic zwitterionic antistatic agent of claim 1 wherein the mass ratio of dimethylaminoethyl methacrylate to bromoalkyl acid is from 1.1 to 1.4.
3. The high molecular weight hydrophilic zwitterionic antistatic agent of claim 1 wherein said water soluble azo initiator is one of azobisisobutyrimidazoline hydrochloride, azobisisobutylamidine hydrochloride, azobiscyanovaleric acid.
4. The high molecular weight hydrophilic zwitterionic antistatic agent of claim 1, wherein the emulsifier is one or more of sodium dodecyl sulfate, cetyltrimethylammonium bromide, and alkylphenol ethoxylates.
5. The high molecular weight hydrophilic zwitterionic antistatic agent of claim 1 wherein the reaction temperature in step (4) is from 50 ℃ to 70 ℃.
6. The high molecular weight hydrophilic zwitterionic antistatic agent of claim 1 wherein said ammonium (2-methacryloyloxy) ethyl dimethyl alkanoate bromide is of the formula:
wherein z ≧ 10.
7. Use of a high molecular weight hydrophilic zwitterionic antistatic agent as claimed in any one of claims 1 to 6 in an antistatic material.
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