CN116285857A - UV pressure-sensitive adhesive and preparation method thereof, and UV pressure-sensitive adhesive tape and preparation method thereof - Google Patents
UV pressure-sensitive adhesive and preparation method thereof, and UV pressure-sensitive adhesive tape and preparation method thereof Download PDFInfo
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- CN116285857A CN116285857A CN202310465580.0A CN202310465580A CN116285857A CN 116285857 A CN116285857 A CN 116285857A CN 202310465580 A CN202310465580 A CN 202310465580A CN 116285857 A CN116285857 A CN 116285857A
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- sensitive adhesive
- pressure
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- electron transport
- transport material
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- 239000004820 Pressure-sensitive adhesive Substances 0.000 title claims abstract description 86
- 238000002360 preparation method Methods 0.000 title abstract description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000000463 material Substances 0.000 claims abstract description 31
- 239000000178 monomer Substances 0.000 claims abstract description 28
- 239000003381 stabilizer Substances 0.000 claims abstract description 28
- 239000003085 diluting agent Substances 0.000 claims abstract description 23
- 150000003384 small molecules Chemical class 0.000 claims abstract description 20
- 229920005749 polyurethane resin Polymers 0.000 claims abstract description 19
- 239000000758 substrate Substances 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 24
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 21
- 238000002156 mixing Methods 0.000 claims description 17
- 239000011248 coating agent Substances 0.000 claims description 16
- 238000000576 coating method Methods 0.000 claims description 16
- 238000003756 stirring Methods 0.000 claims description 10
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 claims description 9
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 claims description 9
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 9
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 9
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical group COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 9
- 229910052801 chlorine Chemical group 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 238000001723 curing Methods 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 claims description 2
- FTALTLPZDVFJSS-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl prop-2-enoate Chemical compound CCOCCOCCOC(=O)C=C FTALTLPZDVFJSS-UHFFFAOYSA-N 0.000 claims description 2
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 claims description 2
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 2
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 claims description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 2
- 238000003848 UV Light-Curing Methods 0.000 claims description 2
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 claims description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 2
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 claims description 2
- FEUIEHHLVZUGPB-UHFFFAOYSA-N oxolan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC1CCCO1 FEUIEHHLVZUGPB-UHFFFAOYSA-N 0.000 claims description 2
- 229920002803 thermoplastic polyurethane Polymers 0.000 claims description 2
- 150000003673 urethanes Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 3
- FXIVKZGDYRLHKF-UHFFFAOYSA-N C(C)OP(OC(C1=C(C=C(C=C1C)C)C)=O)(=O)C1=CC=CC=C1 Chemical compound C(C)OP(OC(C1=C(C=C(C=C1C)C)C)=O)(=O)C1=CC=CC=C1 FXIVKZGDYRLHKF-UHFFFAOYSA-N 0.000 claims 1
- NWWQVENFTIRUMF-UHFFFAOYSA-N diphenylphosphanyl 2,4,6-trimethylbenzoate Chemical compound CC1=CC(C)=CC(C)=C1C(=O)OP(C=1C=CC=CC=1)C1=CC=CC=C1 NWWQVENFTIRUMF-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 6
- 230000035699 permeability Effects 0.000 abstract description 2
- 238000002834 transmittance Methods 0.000 description 14
- 238000011056 performance test Methods 0.000 description 13
- 239000002994 raw material Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 239000002313 adhesive film Substances 0.000 description 7
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 7
- 230000001678 irradiating effect Effects 0.000 description 7
- 238000007719 peel strength test Methods 0.000 description 7
- 229920003023 plastic Polymers 0.000 description 7
- 230000003068 static effect Effects 0.000 description 7
- 238000005259 measurement Methods 0.000 description 6
- 238000005303 weighing Methods 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 description 4
- 229910001486 lithium perchlorate Inorganic materials 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002390 adhesive tape Substances 0.000 description 3
- 239000002216 antistatic agent Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 238000007865 diluting Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000002041 carbon nanotube Substances 0.000 description 2
- 229910021393 carbon nanotube Inorganic materials 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- VOBUAPTXJKMNCT-UHFFFAOYSA-N 1-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound CCCCCC(OC(=O)C=C)OC(=O)C=C VOBUAPTXJKMNCT-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 239000011231 conductive filler Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- -1 ethyl 2,4, 6-trimethyl benzoyl phenyl Chemical group 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Images
Classifications
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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
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
-
- 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
-
- 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]
-
- 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
- C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
- C09J2203/318—Applications of adhesives in processes or use of adhesives in the form of films or foils for the production of liquid crystal displays
-
- 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
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J2301/302—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive being pressure-sensitive, i.e. tacky at temperatures inferior to 30°C
-
- 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
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
- C09J2301/408—Additional features of adhesives in the form of films or foils characterized by the presence of essential components additives as essential feature of the adhesive layer
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polymerisation Methods In General (AREA)
Abstract
The invention discloses a UV pressure-sensitive adhesive containing a micromolecular electron transport material and a preparation method thereof, and a UV pressure-sensitive adhesive tape and a preparation method thereof. The UV pressure-sensitive adhesive containing the small molecular electron transport material comprises the following components in parts by weight: 40-60 parts of acrylic modified polyurethane resin, 30-45 parts of acrylic diluent monomer, 0.5-1 part of photoinitiator, 0.1-0.3 part of stabilizer and 5-15 parts of small molecule electron transport material. The invention selects the micromolecular electron transport material, which not only has good solubility with the solvent-free pressure-sensitive adhesive, but also has good permeability of the prepared UV pressure-sensitive adhesive, and simultaneously has better antistatic effect.
Description
Technical Field
The invention relates to the technical field of resin, in particular to a UV pressure-sensitive adhesive and a preparation method thereof, and a UV pressure-sensitive adhesive tape and a preparation method thereof.
Background
In the consumer electronics field and the screen display field, there is an increasing demand for antistatic properties of adhesives for internal components. The components and materials are used in a dry environment, the generated static electricity is required to be well led out, and the long-acting antistatic effect is achieved. Therefore, there is a need to develop a pressure-sensitive adhesive that has good conductivity and little loss of antistatic properties during use, thereby reducing damage to devices during long-term use.
At present, the common antistatic adhesive tape is mainly prepared by salt antistatic agents. The Chinese patent No. 202011395475.7 discloses an antistatic organosilicon pressure-sensitive adhesive, which is prepared by adopting yin-yang salts to prepare ionic liquid and physically crosslinking with carbon nano tubes to prepare conductive gel, and a small amount of the conductive gel is added to have an antistatic effect, but the method needs a large amount of organic solvent as a dispersion medium, and the introduction of the carbon nano tubes can deepen the color of the pressure-sensitive adhesive, so that the application of the pressure-sensitive adhesive on optical equipment is not facilitated.
Chinese patent No. CN201810811970.8 discloses a method for preparing solvent-free UV-curable low-stripping-force antistatic pressure-sensitive adhesive, which comprises adding lithium perchlorate to obtain adhesive with antistatic value of 10 7-10 Omega antistatic adhesive tape. However, lithium perchlorate belongs to inorganic salt, has poor compatibility with solvent-free oily pressure-sensitive adhesive, and has negative influence on the stripping force of the pressure-sensitive adhesive, so that the lithium perchlorate can only be used as a low-viscosity protective film, and limits the commercial range of the lithium perchlorate.
In addition, the conductive high molecular polymer such as polythiophene, polyaniline, poly (3, 4-ethylenedioxythiophene) and the like has conjugated big pi bond in the molecular structure, has conductivity, does not need to be externally added with conductive filler, but is difficult to dissolve in the solvent-free pressure-sensitive adhesive due to the larger molecular weight. For example, chinese patent No. 202010068314.0 discloses an antistatic pressure-sensitive adhesive tape, which is prepared by uniformly mixing 1, 6-hexanediol diacrylate gel and poly (3, 4-ethylenedioxythiophene) to form a complex, and adding the complex into a pressure-sensitive adhesive to bring an antistatic effect. However, the method needs to combine poly (3, 4-ethylenedioxythiophene) with water-soluble organic salt, which increases the complexity of the process.
Disclosure of Invention
In order to solve the technical problems, the invention provides a UV pressure-sensitive adhesive containing a micromolecular electron transport material and a preparation method thereof, and a UV pressure-sensitive adhesive tape and a preparation method thereof. The small molecular electron transport material selected by the invention has good solubility with the solvent-free pressure-sensitive adhesive, and the prepared UV pressure-sensitive adhesive has good permeability and good antistatic effect, and can well solve the trouble caused by the technical problems.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
in a first aspect, a UV pressure-sensitive adhesive comprising a small molecule electron transport material, comprising the following components in parts by weight: 40-60 parts of acrylic modified polyurethane resin, 30-45 parts of acrylic diluent monomer, 0.5-1 part of photoinitiator, 0.1-0.3 part of stabilizer and 5-15 parts of small molecule electron transport material;
the structural formula of the small molecule electron transport material is shown as (I):
wherein R1 is a C6-C10 alkyl chain, n is an integer of 1 or 2, and X is a fluorine or chlorine atom.
In the present invention, the acrylic-modified urethane resin has a Mn molecular weight range of 25000 to 45000 and contains a carbon-carbon double bond.
In the present invention, the acrylic acid diluting monomer includes acrylic acid, isobornyl acrylate, hydroxyethyl acrylate, hydroxypropyl acrylate, N-vinylpyrrolidone, acryloylmorpholine, tetrahydrofuranyl acrylate, ethoxyethoxyethyl acrylate, glycidyl methacrylate, 1,6-
One or more of hexanediol diacrylate, neopentyl glycol diacrylate, trimethylolpropane triacrylate.
In the present invention, the photoinitiator comprises 2-hydroxy-2-methyl-1-phenyl-1-propanone,
One or more of 1-hydroxy cyclohexyl phenyl ketone, diphenyl- (2, 4, 6-trimethyl benzoyl) phosphorus oxide and ethyl 2,4, 6-trimethyl benzoyl phenyl phosphonate.
In the present invention, the stabilizer is p-methoxyphenol.
In a second aspect, a method for preparing a UV pressure-sensitive adhesive comprising a small molecule electron transport material, the method comprising the steps of: adding the micromolecular electron transport material into an acrylic acid diluted monomer, mixing with acrylic acid modified polyurethane resin, a photoinitiator and a stabilizer, stirring after mixing,
and obtaining the antistatic UV pressure-sensitive adhesive.
In the present invention, the stirring is for 1 to 2 hours at room temperature.
In a third aspect, a pressure-sensitive adhesive tape comprising a substrate and the UV pressure-sensitive adhesive of the first aspect or the second aspect as described above cured on the substrate.
In a fourth aspect, a method for preparing a pressure-sensitive adhesive tape, comprising the steps of: and coating the UV pressure-sensitive adhesive on a substrate, and carrying out irradiation curing by a UV curing lamp to obtain the antistatic UV pressure-sensitive adhesive tape.
Compared with the prior art, the invention has the following beneficial effects:
the invention selects a specific small molecular electron transport material, is synthesized for the first time and is used in the pressure-sensitive adhesive for the first time, and has the advantages of simple synthesis, fixed molecular weight, no need of salinization treatment compared with a conductive high molecular polymer, and can be mixed with a solvent-free UV pressure-sensitive adhesive, and insoluble matters are not seen in the glue preparation process, and the prepared glue film has no influence on the optical performance; in addition, in the structural formula of the specific small molecular electron transport material, the end of the structure is provided with a strong electron withdrawing group, so that an A-D-A structure of electron withdrawing-electron donating-electron withdrawing (accepter-Donor-accepter) is formed, and the Ultraviolet (UV) pressure sensitive adhesive with better antistatic effect can be obtained as an effective electron transport structure.
Drawings
In order to more clearly illustrate the solution of the present invention, a brief description will be given below of the drawings required for the description of the embodiments, it being obvious that the drawings in the following description are some embodiments of the present invention, and that other drawings may be obtained from these drawings without inventive effort for a person skilled in the art.
FIG. 1a is a schematic diagram of the structure of ICDOT-4F as a small molecule electron transport material according to the present invention;
FIG. 1b is a schematic diagram of the structure of ICDOT-4Cl as a small molecule electron transport material according to the present invention;
FIG. 2 is a schematic diagram of a synthetic route of a small molecule electron transport material according to the present invention; in the figure, NBS is N-bromosuccinimide, LDA is lithium diisopropylamide, THF is tetrahydrofuran, tol is toluene, CF is chloroform, and Pyridine is Pyridine;
FIG. 3a is a structural hydrogen spectrum of ICDOT-4F of the small molecule electron transport material of the present invention;
FIG. 3b is a structural hydrogen spectrum of ICDOT-4Cl as a small molecule electron transport material according to the present invention.
Detailed Description
In order to solve the technical problems described in the background art, the present inventors propose a UV pressure-sensitive adhesive containing a small molecule electron transport material, which comprises the following components in parts by weight: 40-60 parts of acrylic modified polyurethane resin, 30-45 parts of acrylic diluent monomer, 0.5-1 part of photoinitiator, 0.1-0.3 part of stabilizer and 5-15 parts of small molecule electron transport material.
The structural formula of the small molecule electron transport material is shown as (I).
Wherein R1 is a C6-C10 alkyl chain, n is an integer of 1 or 2, X is a fluorine or chlorine atom
According to structural formula (I), the synthetic small molecule electron transport materials ICDOT-4F and ICDOT-4Cl have structures shown in fig. 1a and 1b, synthetic routes are shown in fig. 2, and hydrogen spectra of the ICDOT-4F structures are shown in fig. 3a, 1H NMR (400 MHz, CDCl 3) delta 9.09 (s, 2H), 8.50 (dd, J=10.0, 6.4Hz, 2H), 7.63 (t, J=7.6 Hz, 2H), 7.57 (t, J=3.2 Hz, 2H), 4.23 (s, 4H), 4.14 (s, 4H), 1.97 (s, 4H), 1.54-1.47 (m, 8H), 1.31 (m, 50H), 1.10-0.83 (m, 28H), 0.74 (t, J=6.8 Hz, 6H), 0.63 (t, J=7.2 Hz, 6H); the hydrogen spectrum of ICDOT-4Cl structure is shown in FIG. 3b, 1H NMR (500 MHz, CDCl 3) delta 9.04 (t, J=3.0 Hz, 2H), 8.67 (s, 2H), 7.85 (s, 2H), 7.60 (s, 2H), 4.23 (s, 4H), 4.15 (t, J=7.8 Hz, 4H), 2.07-1.92 (m, 4H), 1.62 (s, 2H), 1.50 (s, 6H), 1.38-1.22 (m, 50H), 1.05-0.87 (m, 28H), 0.75 (t, J=6.5 Hz, 6H), 0.66 (t, J=7.2 Hz, 6H).
As shown in fig. 2, wherein when n=1, r1=c8, compound 1 is known to have CAS number 259139-23-6; compound 2 is known as CAS number 920504-00-3; compound 3 is known to have CAS number 2083617-82-5 when x=f and compound 3 is known to have CAS number 2197167-50-1 when x=cl.
The following description of the technical solutions in the embodiments of the present invention will be clear and complete, and it is obvious that the described embodiments are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
The raw materials and equipment used in the invention are common raw materials and equipment in the field unless specified otherwise; the methods used in the present invention are conventional in the art unless otherwise specified.
Unless otherwise defined, all terms used in the specification have the same meaning as commonly understood by one of ordinary skill in the art, but are defined in the specification to be used in the event of a conflict.
For a better description of the objects, technical solutions and advantages of the present invention, the present invention will be further described with reference to the following specific examples.
Example 1
The raw materials are prepared according to the following components in percentage by weight:
60 parts of acrylic modified polyurethane resin
Diluting monomer 45 parts
1 part of photoinitiator
0.3 part of stabilizer
ICDOT-4F:15 parts;
firstly, respectively weighing and uniformly mixing a diluent monomer and ICDOT-4F, then mixing with acrylic acid modified polyurethane resin, a photoinitiator and a stabilizer, and stirring for 2 hours at room temperature, wherein the measured viscosity is about 8110 mPa.s, thus obtaining the antistatic UV pressure-sensitive adhesive. Wherein the diluent monomer comprises 6 parts of acrylic acid, 6 parts of isobornyl acrylate, 15 parts of hydroxyethyl acrylate, 9 parts of N-vinyl pyrrolidone and 9 parts of acryloylmorpholine; the photoinitiator is 0.5 part of 2-hydroxy-2-methyl-1-phenyl-1-acetone and diphenyl0.5 part of- (2, 4, 6-trimethyl benzoyl) phosphorus oxide and 0.3 part of p-methoxyphenol serving as a stabilizer. And (3) coating/coating the antistatic UV pressure-sensitive adhesive on a PET substrate, and irradiating the PET substrate for 45s by a UV lamp to cure the PET substrate to obtain the UV cured pressure-sensitive adhesive tape. The PET substrate had a thickness of 25. Mu.m, and the adhesive film had a thickness of 25. Mu.m. Performance test: the peel force 739gf/25mm measured according to the 180 degree peel strength test method of the national standard GB/T2792-1998 pressure-sensitive adhesive tape, and the surface resistance value measured according to the static performance test method of the national standard GB/T33375-2016 pressure-sensitive adhesive tape are 7.9 x 10 7 Omega, the transmittance measured according to the national standard GB/T2410-2008 transparent plastic transmittance and haze measurement is 91.8%.
Example 2
The raw materials are prepared according to the following components in percentage by weight:
40 parts of acrylic modified polyurethane resin
Diluting monomer 30 parts
0.5 part of photoinitiator
0.1 part of stabilizer
ICDOT-4F:5 parts;
firstly, respectively weighing and uniformly mixing a diluent monomer and ICDOT-4F, then mixing with acrylic acid modified polyurethane resin, a photoinitiator and a stabilizer, and stirring for 1 hour at room temperature, wherein the measured viscosity is about 7940 mPa.s, thus obtaining the antistatic UV pressure-sensitive adhesive. Wherein the diluent monomers comprise 4 parts of acrylic acid, 4 parts of isobornyl acrylate, 10 parts of hydroxyethyl acrylate, 6 parts of N-vinyl pyrrolidone and 6 parts of acryloylmorpholine; the photoinitiator is 0.25 part of 2-hydroxy-2-methyl-1-phenyl-1-acetone, 0.25 part of diphenyl- (2, 4, 6-trimethyl benzoyl) phosphorus oxide and 0.1 part of p-methoxyphenol serving as a stabilizer. And (3) coating/coating the antistatic UV pressure-sensitive adhesive on a PET substrate, and irradiating the PET substrate for 45s by a UV lamp to cure the PET substrate to obtain the UV cured pressure-sensitive adhesive tape. The PET substrate had a thickness of 25. Mu.m, and the adhesive film had a thickness of 25. Mu.m. Performance test: the peel force 1034gf/25mm measured according to the 180 degree peel strength test method of the national standard GB/T2792-1998 pressure-sensitive adhesive tape, and the surface resistance value measured according to the static performance test method of the national standard GB/T33375-2016 pressure-sensitive adhesive tape are 6.3 x 10 10 Omega, the transmittance measured according to the national standard GB/T2410-2008 transparent plastic transmittance and haze measurement is 92.4%.
Example 3
The raw materials are prepared according to the following components in percentage by weight:
acrylic acid modified polyurethane resin 50 parts
36 parts of diluent monomer
0.8 part of photoinitiator
0.2 part of stabilizer
ICDOT-4F:12 parts;
firstly, respectively weighing and uniformly mixing a diluent monomer and ICDOT-4F, then mixing with acrylic acid modified polyurethane resin, a photoinitiator and a stabilizer, and stirring for 2 hours at room temperature, wherein the measured viscosity is about 6590 mPa.s, thus obtaining the antistatic UV pressure-sensitive adhesive. Wherein the diluent monomers comprise 4.8 parts of acrylic acid, 4.8 parts of isobornyl acrylate, 12 parts of hydroxyethyl acrylate, 7.2 parts of N-vinyl pyrrolidone and 7.2 parts of acryloylmorpholine; the photoinitiator is 0.25 part of 2-hydroxy-2-methyl-1-phenyl-1-acetone, 0.25 part of diphenyl- (2, 4, 6-trimethyl benzoyl) phosphorus oxide and 0.2 part of p-methoxyphenol serving as a stabilizer. And (3) coating/coating the antistatic UV pressure-sensitive adhesive on a PET substrate, and irradiating the PET substrate for 45s by a UV lamp to cure the PET substrate to obtain the UV cured pressure-sensitive adhesive tape. The PET substrate had a thickness of 25. Mu.m, and the adhesive film had a thickness of 25. Mu.m. Performance test: the peel force 842gf/25mm measured according to the 180 DEG peel strength test method of the national standard GB/T2792-1998 pressure-sensitive adhesive tape, and the surface resistance value measured according to the static performance test method of the national standard GB/T33375-2016 pressure-sensitive adhesive tape are 2.7 x 10 6 Omega, the transmittance measured according to the national standard GB/T2410-2008 transparent plastic transmittance and haze measurement is 92.3%.
Example 4
The raw materials are prepared according to the following components in percentage by weight:
acrylic acid modified polyurethane resin 50 parts
36 parts of diluent monomer
0.8 part of photoinitiator
0.2 part of stabilizer
ICDOT-4Cl:12 parts of
Firstly, respectively weighing and uniformly mixing a diluent monomer and ICDOT-4Cl, then mixing with acrylic acid modified polyurethane resin, a photoinitiator and a stabilizer, stirring for 1 hour at room temperature, and obtaining the anti-aging agent with the measured viscosity of about 8630 mPa.sAn electrostatic UV pressure sensitive adhesive. Wherein the diluent monomers comprise 4.8 parts of acrylic acid, 4.8 parts of isobornyl acrylate, 12 parts of hydroxyethyl acrylate, 7.2 parts of N-vinyl pyrrolidone and 7.2 parts of acryloylmorpholine; the photoinitiator is 0.25 part of 2-hydroxy-2-methyl-1-phenyl-1-acetone, 0.25 part of diphenyl- (2, 4, 6-trimethyl benzoyl) phosphorus oxide and 0.2 part of p-methoxyphenol serving as a stabilizer. And (3) coating/coating the antistatic UV pressure-sensitive adhesive on a PET substrate, and irradiating the PET substrate for 45s by a UV lamp to cure the PET substrate to obtain the UV cured pressure-sensitive adhesive tape. The PET substrate had a thickness of 25. Mu.m, and the adhesive film had a thickness of 25. Mu.m. Performance test: the peel force 809gf/25mm measured according to the 180 degree peel strength test method of the national standard GB/T2792-1998 pressure sensitive adhesive tape, and the surface resistance value measured according to the static performance test method of the national standard GB/T33375-2016 adhesive tape are 5.1 x 10 6 Omega, the transmittance measured according to the national standard GB/T2410-2008 transparent plastic transmittance and haze measurement is 92.3%.
Comparative example 1
The raw materials are prepared according to the following components in percentage by weight:
40 parts of acrylic modified polyurethane resin
36 parts of diluent monomer
0.5 part of photoinitiator
0.2 parts of stabilizer;
the components are respectively weighed and put into a single-neck flask, and stirred for 1 hour at room temperature, and the measured viscosity is about 5900 mPa.s, so that the antistatic UV pressure-sensitive adhesive is obtained. Wherein the diluent monomers comprise 4.8 parts of acrylic acid, 4.8 parts of isobornyl acrylate, 12 parts of hydroxyethyl acrylate, 7.2 parts of N-vinyl pyrrolidone and 7.2 parts of acryloylmorpholine; the photoinitiator is 0.25 part of 2-hydroxy-2-methyl-1-phenyl-1-acetone, 0.25 part of diphenyl- (2, 4, 6-trimethyl benzoyl) phosphorus oxide and 0.2 part of p-methoxyphenol serving as a stabilizer. And (3) coating/coating the antistatic UV pressure-sensitive adhesive on a PET substrate, and irradiating the PET substrate for 45s by a UV lamp to cure the PET substrate to obtain the UV cured pressure-sensitive adhesive tape. The PET substrate had a thickness of 25. Mu.m, and the adhesive film had a thickness of 25. Mu.m. Performance test: the peel force 1197gf/25mm measured according to the 180 degree peel strength test method of the national standard GB/T2792-1998 pressure-sensitive adhesive tape, and the surface resistance value measured according to the static performance test method of the national standard GB/T33375-2016 pressure-sensitive adhesive tape are 5.6x10 14 Omega, according toThe transmittance measured by the determination of the transmittance and haze of the national standard GB/T2410-2008 transparent plastic is 92.6%.
Comparative example 2
The raw materials are prepared according to the following components in percentage by weight:
40 parts of acrylic modified polyurethane resin
36 parts of diluent monomer
0.5 part of photoinitiator
0.2 part of stabilizer
Additive quaternary ammonium salt cationic antistatic agent SH-105 parts;
firstly, respectively weighing and mixing a diluent monomer and SH-105, then mixing with acrylic acid modified polyurethane resin, a photoinitiator and a stabilizer, and stirring for 1-2 hours at room temperature, wherein the measured viscosity is about 6090 mPa.s, thus obtaining the antistatic UV pressure-sensitive adhesive. Wherein the diluent monomers comprise 4 parts of acrylic acid, 4 parts of isobornyl acrylate, 10 parts of hydroxyethyl acrylate, 6 parts of N-vinyl pyrrolidone and 6 parts of acryloylmorpholine; the photoinitiator is 0.25 part of 2-hydroxy-2-methyl-1-phenyl-1-acetone, 0.25 part of diphenyl- (2, 4, 6-trimethyl benzoyl) phosphorus oxide and 0.2 part of p-methoxyphenol serving as a stabilizer. And (3) coating/coating the antistatic UV pressure-sensitive adhesive on a PET substrate, and irradiating the PET substrate for 45s by a UV lamp to cure the PET substrate to obtain the UV cured pressure-sensitive adhesive tape. The PET substrate had a thickness of 25. Mu.m, and the adhesive film had a thickness of 25. Mu.m. Performance test of SH-105 due to poor solubility: the peel force 767gf/25mm measured according to the 180 DEG peel strength test method of the national standard GB/T2792-1998 pressure-sensitive adhesive tape, and the surface resistance value measured according to the test method of the electrostatic property of the national standard GB/T33375-2016 pressure-sensitive adhesive tape are 9.1 x 10 10 Omega, the transmittance measured according to the national standard GB/T2410-2008 transparent plastic transmittance and haze measurement is 88.3%.
Comparative example 3
The raw materials are prepared according to the following components in percentage by weight:
40 parts of acrylic modified polyurethane resin
36 parts of diluent monomer
0.5 part of photoinitiator
0.2 part of stabilizer
Additive type antistatic agent Atmer163 12 parts;
atmer163 is a liquid ethoxylated amine. Firstly, respectively weighing and mixing a diluent monomer and an Atmer163, then mixing with an acrylic modified polyurethane resin, a photoinitiator and a stabilizer, and stirring for 1-2 hours at room temperature, wherein the measured viscosity is about 5990 mPa.s, thus obtaining the antistatic UV pressure-sensitive adhesive. Wherein the diluent monomers comprise 4 parts of acrylic acid, 4 parts of isobornyl acrylate, 10 parts of hydroxyethyl acrylate, 6 parts of N-vinyl pyrrolidone and 6 parts of acryloylmorpholine; the photoinitiator is 0.25 part of 2-hydroxy-2-methyl-1-phenyl-1-acetone, 0.25 part of diphenyl- (2, 4, 6-trimethyl benzoyl) phosphorus oxide and 0.2 part of p-methoxyphenol serving as a stabilizer. And (3) coating/coating the antistatic UV pressure-sensitive adhesive on a PET substrate, and irradiating the PET substrate for 45s by a UV lamp to cure the PET substrate to obtain the UV cured pressure-sensitive adhesive tape. The PET substrate had a thickness of 25. Mu.m, and the adhesive film had a thickness of 25. Mu.m. The performance test is as follows: the peel force 854gf/25mm measured according to the 180 degree peel strength test method of the national standard GB/T2792-1998 pressure-sensitive adhesive tape, and the surface resistance value measured according to the static performance test method of the national standard GB/T33375-2016 pressure-sensitive adhesive tape are 3.1 x 10 9 Omega, the transmittance measured according to the national standard GB/T2410-2008 transparent plastic transmittance and haze measurement is 90.6%.
All numbers or expressions referring to amounts of components, process conditions, etc. used in the specification and claims are to be understood as modified in all instances by "about". All ranges directed to the same component or property are inclusive of the endpoints, which endpoints are independently combinable. Because these ranges are continuous, they include every value between the minimum and maximum values. It should also be understood that any numerical range recited herein is intended to include all sub-ranges within that range.
The above examples only show embodiments of the present invention, and the description thereof is more specific and detailed, but should not be construed as limiting the scope of the invention, but all technical solutions obtained by equivalent substitution or equivalent transformation shall fall within the scope of the invention.
Claims (10)
1. The UV pressure-sensitive adhesive containing the small molecular electron transport material is characterized by comprising the following components in parts by weight: 40-60 parts of acrylic modified polyurethane resin, 30-45 parts of acrylic diluent monomer, 0.5-1 part of photoinitiator, 0.1-0.3 part of stabilizer and 5-15 parts of small molecule electron transport material;
the structural formula of the small molecule electron transport material is shown as (I):
wherein R1 is a C6-C10 alkyl chain, n is an integer of 1 or 2, and X is a fluorine or chlorine atom.
2. The UV pressure-sensitive adhesive containing a small molecule electron transport material according to claim 1, wherein the acrylic-modified urethane resin has Mn molecular weight in the range of 25000 to 45000 and contains carbon-carbon double bonds.
3. The UV pressure-sensitive adhesive of claim 1 or 2, wherein the acrylic diluent monomer comprises one or more of acrylic acid, isobornyl acrylate, hydroxyethyl acrylate, hydroxypropyl acrylate, N-vinyl pyrrolidone, acryloylmorpholine, tetrahydrofuranyl acrylate, ethoxyethoxyethyl acrylate, glycidyl methacrylate, 1, 6-hexanediol diacrylate, neopentyl glycol diacrylate, trimethylolpropane triacrylate.
4. The UV pressure sensitive adhesive comprising a small molecule electron transport material according to claim 3, wherein the photoinitiator comprises one or more of 2-hydroxy-2-methyl-1-phenyl-1-propanone, 1-hydroxycyclohexyl phenyl ketone, diphenyl- (2, 4, 6-trimethylbenzoyl) oxyphosphorus, ethyl 2,4, 6-trimethylbenzoyl phenylphosphonate.
5. The UV pressure sensitive adhesive containing a small molecule electron transport material according to claim 4, wherein the stabilizer is p-methoxyphenol.
6. The method for preparing the UV pressure-sensitive adhesive containing the small molecule electron transport material according to any one of claims 1 to 5, comprising the steps of: adding the micromolecular electron transport material into an acrylic acid diluted monomer, mixing with acrylic acid modified polyurethane resin, a photoinitiator and a stabilizer, and stirring after mixing to obtain the UV pressure-sensitive adhesive.
7. The method for preparing a UV pressure-sensitive adhesive according to claim 6, wherein the stirring is performed for 1 to 2 hours at room temperature.
8. A pressure-sensitive adhesive tape comprising a substrate and, cured thereon, the UV pressure-sensitive adhesive according to any one of claims 1 to 5 or the UV pressure-sensitive adhesive produced by the production method according to claim 6 or 7.
9. The method for producing a pressure-sensitive adhesive tape as claimed in claim 8, comprising the steps of: and coating the UV pressure-sensitive adhesive on a substrate, and carrying out irradiation curing by a UV curing lamp to obtain the UV pressure-sensitive adhesive tape.
10. The method for producing a pressure-sensitive adhesive tape according to claim 9, wherein the curing time is 30 to 60 seconds.
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