CN111253882B - Antistatic pressure-sensitive adhesive, preparation method thereof and antistatic pressure-sensitive adhesive tape - Google Patents
Antistatic pressure-sensitive adhesive, preparation method thereof and antistatic pressure-sensitive adhesive tape Download PDFInfo
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- CN111253882B CN111253882B CN202010068314.0A CN202010068314A CN111253882B CN 111253882 B CN111253882 B CN 111253882B CN 202010068314 A CN202010068314 A CN 202010068314A CN 111253882 B CN111253882 B CN 111253882B
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
- C09J9/02—Electrically-conducting adhesives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/50—Use of additives, e.g. for stabilisation
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
- C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C09J7/385—Acrylic polymers
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Adhesive Tapes (AREA)
Abstract
The invention provides an antistatic pressure-sensitive adhesive, which comprises the following components in parts by weight: 20-40 parts of 1, 6-hexanediol diacrylate gel, 30-40 parts of isooctyl acrylate, 3-10 parts of AA refined acrylic acid, 10-20 parts of 1-hydroxycyclohexyl phenyl ketone and 10-20 parts of dodecyl mercaptan; 1-5 parts by weight of poly (3, 4-ethylenedioxythiophene), wherein the preparation method of the 1, 6-hexanediol diacrylate gel comprises the following steps: adding persulfate into a mixed solution of 1, 6-hexanediol diacrylate and triethanolamine in a weight ratio of 3:1-2, and uniformly mixing to obtain the 1, 6-hexanediol diacrylate gel. The UV light is used for treating the preparation process instead of heating, the processing mode is simple, the production is more energy-saving and environment-friendly, and the prepared pressure-sensitive adhesive has strong weather resistance and good radiation resistance in the aspect of electromagnetic radiation.
Description
Technical Field
The invention belongs to the technical field of adhesives, and relates to an antistatic pressure-sensitive adhesive, a preparation method thereof and an antistatic pressure-sensitive adhesive tape.
Background
With the rapid development of electronic technologies such as mobile phones, computers, touch displays and the like, the integration level of electronic materials is higher, microelectronics is more precise, and the sensitivity to static electricity is higher and higher, such as field effect transistors, chips, large-scale integrated circuits, touch screens and the like are more and more sensitive to damage caused by static electricity, and the surface resistivity of the electronic materials in a low-humidity environment is required to be below 1010 omega/□ in the processing and using processes, and an antistatic protection film with a long-acting antistatic effect is required to be selected and used, so that a pressure-sensitive adhesive with a good antistatic effect is required to be developed to prepare an antistatic protection film to lead out static electricity generated in the processing process of the electronic materials, and the damage to the electronic materials caused by static electricity accumulation in.
The conventional antistatic agent such as carbon black or graphite is added into the pressure-sensitive adhesive to prepare the antistatic protective film, which is darker or black, is not beneficial to visual observation and analysis detection and influences the attractiveness. The antistatic protective film prepared by adding metal powder into the pressure-sensitive adhesive has the phenomena that the film surface is not smooth and even damages electronic elements, and the observation is influenced due to poor transparency. The problems of poor compatibility with pressure-sensitive adhesive, degumming, adhesive layer transfer, serious mottle and the like caused by great fluctuation of the peel strength performance of the pressure-sensitive adhesive due to the adoption of conductive high molecular polymers such as polythiophene, polyaniline and the like are solved, an antistatic coating is independently coated, the pressure-sensitive adhesive is coated again, the antistatic effect is obviously weakened, and the production cost is increased due to the adoption of two coating processes.
Patent CN201310654380.6 discloses an antistatic pressure-sensitive adhesive protective film and a preparation method thereof, the method adopts the synergistic compounding of electrolyte-based polymer conductive substances and nano materials to realize the conductive effect, the maximum antistatic effect can be realized under a very small addition amount, and the peeling force of the protective film and no residual adhesive after peeling are not influenced. However, the method adopts expensive nano silver wires and nano copper wires, has high cost and limited raw material sources, and is not suitable for wide popularization and application.
Patent CN201510610771.7 discloses an antistatic pressure-sensitive adhesive and a preparation method thereof, and the method adopts LiAsF6 to form an ion conductive polymer by complexing with polyurethane macromolecular chains synthesized by reaction of polyoxyethylene polyol, polyoxypropylene polyol and polytetrahydrofuran polyol with isocyanate. The compatibility of the ionic conductive polymer structure and the oily acrylate resin is poor, and the prepared protective film has poor transparency under a low-temperature environment due to the crystallization temperature difference of the pressure-sensitive adhesive layer.
Patent CN201910153791.4 discloses an antistatic silicone pressure sensitive adhesive product, which is prepared by forming an antistatic layer on a substrate film, further forming a silica gel layer containing an ionic liquid type antistatic composition on the antistatic layer, and arranging a release layer on the silica gel layer. The method firstly has the advantages of complex preparation method, high preparation cost, reduced viscosity of the pressure-sensitive adhesive and small adhesive force.
Disclosure of Invention
The invention aims to solve the problem that a pressure-sensitive adhesive commonly used in electronic equipment and vehicle-mounted equipment in the prior art is stripped and charged, and the formula and the preparation method of the pressure-sensitive adhesive are deeply researched and developed to obtain an antistatic pressure-sensitive adhesive, a preparation method thereof and an antistatic pressure-sensitive adhesive tape.
In order to achieve the purposes, the specific scheme is as follows:
an antistatic pressure-sensitive adhesive comprises the following components: 20-40 parts of 1, 6-hexanediol diacrylate gel, 30-40 parts of isooctyl acrylate, 3-10 parts of AA refined acrylic acid, 10-20 parts of 1-hydroxycyclohexyl phenyl ketone and 10-20 parts of dodecyl mercaptan; 1-5 parts by weight of poly (3, 4-ethylenedioxythiophene), wherein the preparation method of the 1, 6-hexanediol diacrylate gel comprises the following steps: adding persulfate into a mixed solution of 1, 6-hexanediol diacrylate and triethanolamine in a weight ratio of 3:1-2, and uniformly mixing to obtain the 1, 6-hexanediol diacrylate gel.
Wherein the persulfate is any one of zinc sulfate or magnesium sulfate, and the 1, 6-hexanediol diacrylate is zinc salt or magnesium salt.
The AA fine acrylic acid is prepared by the following steps: absorbing and rectifying a propylene oxidation product by water to obtain crude acrylic acid containing 10-1000 ppm of acrolein, furfural and/or benzaldehyde and other impurities as a raw material, adding a polymerization inhibitor hydroquinone into the crude acrylic acid, selecting an alcohol substance containing 3-10 carbon atoms as an aldehyde removing reagent, reacting with aldehyde in the crude acrylic acid, then carrying out intermittent or continuous reduced pressure rectification, wherein the vacuum degree of the reduced pressure rectification is 0.1-50 kPa, preferably 0.5-20 kPa, obtaining polymerization grade refined acrylic acid with zero aldehyde content and the purity of the acrylic acid of more than 99.80%, then adding resveratrol with the weight part of the acrylic acid of 0.1-3% into the polymerization grade refined acrylic acid, and polymerizing for 20min under the illumination of 200-500nm of 2000LEX to obtain AA refined acrylic acid.
Preferably, in the process of preparing AA refined acrylic acid, resveratrol with the weight part of acrylic acid of 0.1-0.5 percent is added into polymer grade refined acrylic acid.
Preferably, the component formulation is as follows: 25-35 parts of 1, 6-hexanediol diacrylate gel, 30-40 parts of isooctyl acrylate, 3-5 parts of AA refined acrylic acid, 10-20 parts of 1-hydroxycyclohexyl phenyl ketone and 10-20 parts of dodecyl mercaptan; 2-8 parts of poly (3, 4-ethylenedioxythiophene).
Preferably, the weight part ratio of the 1, 6-hexanediol diacrylate gel to the poly (3, 4-ethylenedioxythiophene) and AA refined acrylic acid is 5:1: 1.
The preparation method of the antistatic pressure-sensitive adhesive comprises the following steps: firstly, uniformly mixing 1, 6-hexanediol diacrylate gel and poly (3, 4-ethylenedioxythiophene) to form a complex, then adding isooctyl acrylate, 1-hydroxycyclohexyl phenyl ketone and dodecyl mercaptan, adding into a container, uniformly stirring, and finally adding AA fine acrylic acid under the illumination of the intensity of 2200lex and the wavelength of 500 nm; and (4) stirring for 20-50min under illumination to obtain the antistatic pressure-sensitive adhesive.
The antistatic pressure-sensitive adhesive tape is prepared by coating the antistatic pressure-sensitive adhesive.
Compared with the prior art, the invention has the following technical effects:
1. the UV light is used for treating the preparation process instead of heating, the processing mode is simple, the production is more energy-saving and environment-friendly, and the prepared pressure-sensitive adhesive has strong weather resistance and good radiation resistance in the aspect of electromagnetic radiation.
2. The AA refined acrylic acid which is specially processed has unexpected technical effect on the aspect of high temperature resistance, and compared with the existing antistatic pressure-sensitive adhesive, the AA refined acrylic acid has stronger viscosity and longer high temperature resistance time.
3. Through a large number of innovations and tests, the viscosity and the antistatic effect of the prepared antistatic subsensitive adhesive tape are in the best state when the weight part ratio of the specially prepared 1, 6-hexanediol diacrylate gel to the poly (3, 4-ethylenedioxythiophene) and the AA fine acrylic acid is 5:1: 1.
Detailed Description
The technical solution of the present invention will be clearly and completely described below with reference to the embodiments of the present invention. It is to be understood that the described embodiments are merely exemplary of the invention, and not restrictive of the full scope of the invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The invention provides an antistatic pressure-sensitive adhesive, which comprises the following components: 1, 6-hexanediol diacrylate gel, isooctyl acrylate, AA refined acrylic acid, 1-hydroxycyclohexyl phenyl ketone, dodecyl mercaptan and poly (3, 4-ethylenedioxythiophene).
The preparation method of the 1, 6-hexanediol diacrylate gel comprises the following steps: adding zinc persulfate into a mixed solution of zinc 1, 6-hexanediol diacrylate and triethanolamine in a weight ratio of 3:1-2, and uniformly mixing, wherein the weight ratio of the zinc persulfate to the zinc 1, 6-hexanediol diacrylate is 1: 20-30, and obtaining the 1, 6-hexanediol diacrylate gel. .
The preparation process of the AA refined acrylic acid comprises the following steps: absorbing and rectifying a propylene oxidation product with water to obtain crude acrylic acid containing 10-1000 ppm of acrolein, furfural and/or benzaldehyde and other impurities as a raw material, adding a polymerization inhibitor hydroquinone into the crude acrylic acid, selecting an alcohol substance containing 3-10 carbon atoms as an aldehyde removing reagent, reacting with aldehyde in the crude acrylic acid, then carrying out intermittent or continuous reduced pressure rectification, wherein the vacuum degree of the reduced pressure rectification is 0.1-50 kPa, preferably 0.5-20 kPa, obtaining polymerization grade refined acrylic acid with the aldehyde content of zero and the acrylic acid purity of more than 99.80%, then adding resveratrol with the weight part of acrylic acid of 0.1-0.5% into the polymerization grade refined acrylic acid, and polymerizing for 20min under the illumination of 2000LEX200-500nm to obtain AA refined acrylic acid.
Example 1
The embodiment provides an antistatic pressure-sensitive adhesive which comprises the following components in parts by weight: 20 parts by weight of 1, 6-hexanediol diacrylate gel, 30 parts by weight of isooctyl acrylate, 3 parts by weight of AA fine acrylic acid, 12 parts by weight of 1-hydroxycyclohexyl phenyl ketone, 18 parts by weight of dodecyl mercaptan and 5 parts by weight of poly (3, 4-ethylenedioxythiophene).
The preparation method of the antistatic pressure-sensitive adhesive comprises the following steps: firstly, uniformly mixing 1, 6-hexanediol diacrylate gel and poly (3, 4-ethylenedioxythiophene) to form a complex, then adding isooctyl acrylate, 1-hydroxycyclohexyl phenyl ketone and dodecyl mercaptan, adding into a container, uniformly stirring, and finally adding AA fine acrylic acid under the illumination of the intensity of 2200lex and the wavelength of 500 nm; and (3) stirring for 20-50min under illumination to obtain the antistatic pressure-sensitive adhesive of the example 1.
The using method comprises the following steps: the prepared antistatic pressure-sensitive adhesive is placed into a foaming machine for foaming and then coated on the front surface and the back surface of the base material, and then the release film is pasted.
Examples 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 were prepared as in example 1, with the following formulation:
comparative example 1
The embodiment provides a pressure-sensitive adhesive which comprises the following components in parts by weight: 20 parts by weight of ordinary 1, 6-hexanediol diacrylate, 30 parts by weight of isooctyl acrylate, 3 parts by weight of ordinary acrylic acid, 12 parts by weight of 1-hydroxycyclohexyl phenyl ketone, 18 parts by weight of dodecanethiol.
The preparation method of the electric pressure-sensitive adhesive comprises the following steps: firstly, adding 1, 6-hexanediol diacrylate, isooctyl acrylate, 1-hydroxycyclohexyl phenyl ketone and dodecyl mercaptan into a container, uniformly stirring, and finally adding acrylic acid under the illumination of the intensity of 2200lex and the wavelength of 500 nm; and (3) stirring for 20-50min under illumination to obtain the pressure-sensitive adhesive of the comparative example 1.
The using method comprises the following steps: the prepared pressure-sensitive adhesive is placed into a foaming machine for foaming and then coated on the front surface and the back surface of the base material, and then the release film is pasted.
Comparative examples 2-12 were prepared in the same manner and the specific formulations were as follows:
the viscosity and antistatic effect of examples 1 to 12 and comparative examples 1 to 12 were compared and the results were as follows:
the test results for comparative examples 1-12 are:
as can be seen from the above examples, the examples 1 to 12 have significant advantages in terms of viscosity compared with the comparative examples 1 to 12, especially the examples 2, 9 and 12 have great advantages in terms of viscosity sensitivity, especially in antistatic rooms, and the examples have remarkable advantages compared with the prior art.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (6)
1. An antistatic pressure-sensitive adhesive comprises the following components: 20-40 parts of 1, 6-hexanediol diacrylate gel, 30-40 parts of isooctyl acrylate, 3-10 parts of AA refined acrylic acid, 10-20 parts of 1-hydroxycyclohexyl phenyl ketone and 10-20 parts of dodecyl mercaptan; 2-10 parts by weight of poly (3, 4-ethylenedioxythiophene);
the preparation method of the 1, 6-hexanediol diacrylate gel comprises the following steps: adding persulfate into a mixed solution of 1, 6-hexanediol diacrylate and triethanolamine in a weight ratio of 3:1-2, and uniformly mixing to obtain 1, 6-hexanediol diacrylate gel;
the preparation method of the AA fine acrylic acid comprises the following steps: absorbing and rectifying the propylene oxidation product with water to obtain crude acrylic acid containing 10-1000 ppm of acrolein, furfural and/or benzaldehyde impurities as a raw material, adding a polymerization inhibitor hydroquinone into the crude acrylic acid, selecting an alcohol substance containing 3-10 carbon atoms as an aldehyde removing reagent, reacting with aldehyde in the crude acrylic acid, and then performing intermittent or continuous reduced pressure rectification with the vacuum degree of 0.1-50 kPa to obtain polymer grade refined acrylic acid with zero aldehyde content and the acrylic acid purity of more than 99.80%, then adding resveratrol accounting for 0.1-0.5% of the weight of the acrylic acid into the polymer grade refined acrylic acid, and polymerizing for 20min under the illumination of 2000LEX200-500nm to obtain AA refined acrylic acid;
the preparation method of the antistatic pressure-sensitive adhesive comprises the following steps: firstly, uniformly mixing 1, 6-hexanediol diacrylate gel and poly (3, 4-ethylenedioxythiophene) to form a complex, then adding isooctyl acrylate, 1-hydroxycyclohexyl phenyl ketone and dodecyl mercaptan, adding into a container, uniformly stirring, and finally adding AA fine acrylic acid under the illumination of the intensity of 2200LEX with the wavelength of 500 nm; and (4) stirring for 20-50min under illumination to obtain the antistatic pressure-sensitive adhesive.
2. The antistatic pressure sensitive adhesive of claim 1, wherein: the persulfate is any one of zinc sulfate or magnesium sulfate.
3. The antistatic pressure sensitive adhesive of claim 1, wherein: the formula of the components is as follows: 25-35 parts of 1, 6-hexanediol diacrylate gel, 30-40 parts of isooctyl acrylate, 3-5 parts of AA refined acrylic acid, 10-20 parts of 1-hydroxycyclohexyl phenyl ketone and 10-20 parts of dodecyl mercaptan; 2-8 parts of poly (3, 4-ethylenedioxythiophene).
4. The antistatic pressure sensitive adhesive of claim 1, wherein: the weight portion ratio of the 1, 6-hexanediol diacrylate gel to the poly (3, 4-ethylenedioxythiophene) and AA refined acrylic acid is 5:1: 1.
5. A method for preparing the antistatic pressure-sensitive adhesive according to any one of claims 1 to 4, comprising the steps of: firstly, uniformly mixing 1, 6-hexanediol diacrylate gel and poly (3, 4-ethylenedioxythiophene) to form a complex, then adding isooctyl acrylate, 1-hydroxycyclohexyl phenyl ketone and dodecyl mercaptan, adding into a container, uniformly stirring, and finally adding AA fine acrylic acid under the illumination of the intensity of 2200LEX with the wavelength of 500 nm; and (3) stirring for 20-50min under illumination to obtain the antistatic pressure-sensitive adhesive as claimed in any one of claims 1-4.
6. An antistatic pressure sensitive adhesive tape characterized by: prepared by coating the antistatic pressure-sensitive adhesive as claimed in any one of claims 1 to 4.
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| CN202010068314.0A CN111253882B (en) | 2020-01-21 | 2020-01-21 | Antistatic pressure-sensitive adhesive, preparation method thereof and antistatic pressure-sensitive adhesive tape |
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| CN202010068314.0A CN111253882B (en) | 2020-01-21 | 2020-01-21 | Antistatic pressure-sensitive adhesive, preparation method thereof and antistatic pressure-sensitive adhesive tape |
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| CN111253882B true CN111253882B (en) | 2021-05-25 |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1717462A (en) * | 2002-12-04 | 2006-01-04 | 蒂萨股份公司 | Anti-static self-adhesive strip |
| CN101085733A (en) * | 2007-06-29 | 2007-12-12 | 上海华谊丙烯酸有限公司 | Method for preparing refined acrylic acid by removing micro-impurity aldehyde |
| CN101265048A (en) * | 2008-04-24 | 2008-09-17 | 北京朗巍时代科技有限责任公司 | Acrylate grouting liquid and preparation method thereof |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1717462A (en) * | 2002-12-04 | 2006-01-04 | 蒂萨股份公司 | Anti-static self-adhesive strip |
| CN101085733A (en) * | 2007-06-29 | 2007-12-12 | 上海华谊丙烯酸有限公司 | Method for preparing refined acrylic acid by removing micro-impurity aldehyde |
| CN101265048A (en) * | 2008-04-24 | 2008-09-17 | 北京朗巍时代科技有限责任公司 | Acrylate grouting liquid and preparation method thereof |
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