CN117551418A - Adhesive for aluminum plastic film and preparation process thereof - Google Patents
Adhesive for aluminum plastic film and preparation process thereof Download PDFInfo
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- CN117551418A CN117551418A CN202410046318.7A CN202410046318A CN117551418A CN 117551418 A CN117551418 A CN 117551418A CN 202410046318 A CN202410046318 A CN 202410046318A CN 117551418 A CN117551418 A CN 117551418A
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- adhesive
- plastic film
- aluminum plastic
- modified
- preparation process
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- 229910052782 aluminium Inorganic materials 0.000 title claims abstract description 47
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 title claims abstract description 47
- 239000000853 adhesive Substances 0.000 title claims abstract description 43
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 43
- 239000002985 plastic film Substances 0.000 title claims abstract description 43
- 229920006255 plastic film Polymers 0.000 title claims abstract description 43
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- 239000004642 Polyimide Substances 0.000 claims abstract description 41
- 229920001721 polyimide Polymers 0.000 claims abstract description 41
- 229920005989 resin Polymers 0.000 claims abstract description 39
- 239000011347 resin Substances 0.000 claims abstract description 39
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 claims abstract description 30
- IYTXQZMZTQHONB-UHFFFAOYSA-N 4-[(4-aminophenoxy)-dimethylsilyl]oxyaniline Chemical compound C=1C=C(N)C=CC=1O[Si](C)(C)OC1=CC=C(N)C=C1 IYTXQZMZTQHONB-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 23
- 150000004985 diamines Chemical class 0.000 claims abstract description 23
- 229920000570 polyether Polymers 0.000 claims abstract description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 22
- MERLDGDYUMSLAY-UHFFFAOYSA-N 4-[(4-aminophenyl)disulfanyl]aniline Chemical compound C1=CC(N)=CC=C1SSC1=CC=C(N)C=C1 MERLDGDYUMSLAY-UHFFFAOYSA-N 0.000 claims abstract description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 67
- 238000010438 heat treatment Methods 0.000 claims description 46
- 238000002156 mixing Methods 0.000 claims description 43
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 34
- 239000004952 Polyamide Substances 0.000 claims description 18
- 239000012153 distilled water Substances 0.000 claims description 18
- 229920002647 polyamide Polymers 0.000 claims description 18
- 239000005457 ice water Substances 0.000 claims description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- 239000006185 dispersion Substances 0.000 claims description 16
- 238000002390 rotary evaporation Methods 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 16
- 238000003756 stirring Methods 0.000 claims description 16
- 229920001684 low density polyethylene Polymers 0.000 claims description 11
- 239000004702 low-density polyethylene Substances 0.000 claims description 11
- -1 polypropylene Polymers 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical group CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 9
- 238000001816 cooling Methods 0.000 claims description 9
- 238000001704 evaporation Methods 0.000 claims description 9
- 238000001914 filtration Methods 0.000 claims description 9
- 238000005406 washing Methods 0.000 claims description 9
- 239000004743 Polypropylene Substances 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- 229920001155 polypropylene Polymers 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 6
- 229920005672 polyolefin resin Polymers 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 4
- 125000006159 dianhydride group Chemical class 0.000 claims 2
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 abstract description 18
- 239000003792 electrolyte Substances 0.000 abstract description 6
- 239000002994 raw material Substances 0.000 abstract description 4
- 238000005260 corrosion Methods 0.000 abstract description 3
- 230000007797 corrosion Effects 0.000 abstract description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract description 2
- 238000004132 cross linking Methods 0.000 abstract description 2
- 238000009459 flexible packaging Methods 0.000 abstract description 2
- ZHPNWZCWUUJAJC-UHFFFAOYSA-N fluorosilicon Chemical compound [Si]F ZHPNWZCWUUJAJC-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052744 lithium Inorganic materials 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 239000011888 foil Substances 0.000 description 3
- 238000007731 hot pressing Methods 0.000 description 3
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000005022 packaging material Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WWBPNLAHHCMPJF-UHFFFAOYSA-N 4-dimethylsilyloxyaniline Chemical compound C[SiH](C)OC1=CC=C(N)C=C1 WWBPNLAHHCMPJF-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
Classifications
-
- 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
- C09J179/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09J161/00 - C09J177/00
- C09J179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C09J179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1039—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors comprising halogen-containing substituents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
- C08G73/106—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain containing silicon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
- C08G73/1064—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
- C08G73/1071—Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain
-
- 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
- C09J11/08—Macromolecular additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2207/00—Properties characterising the ingredient of the composition
- C08L2207/06—Properties of polyethylene
- C08L2207/066—LDPE (radical process)
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- 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
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention relates to the technical field of flexible packaging of lithium batteries, in particular to an adhesive for an aluminum plastic film and a preparation process thereof; in order to improve the high temperature resistance and electrolyte corrosion resistance of the finally prepared aluminum plastic film, the invention prepares modified polyimide bonding resin, uses bis (4-aminophenoxy) dimethylsilane to react with hexafluorodianhydride to obtain dianhydride raw materials containing fluorine-silicon element, and increases the high temperature resistance and water resistance of the polyimide material; the invention further prepares polyether modified diamine by using ethylene glycol diglycidyl ether and 4,4' -diaminodiphenyl disulfide to react, long carbon chains are introduced into the polyether modified diamine by limiting raw materials, and ether bonds in the polyether modified diamine are utilized to increase deformability of the adhesive, so that the problem of reduced adhesive force caused by reduced crosslinking property of the adhesive due to rigid carbocycles is avoided, and finally, the high temperature resistance and electrolyte resistance of the adhesive are improved while the adhesive force is maintained.
Description
Technical Field
The invention relates to the technical field of flexible packaging of lithium batteries, in particular to an adhesive for an aluminum plastic film and a preparation process thereof.
Background
With the development of new energy automobiles in recent years, the demand of batteries is gradually developed to two aspects of high energy density and safety performance; the traditional metal battery outer packaging material has limitations, and the requirements of diversified shapes and light weight cannot be met, so that the aluminum plastic film becomes a main stream packaging material of the battery due to the excellent mechanical property and packaging property of the aluminum plastic film.
Although aluminum plastic films offer many advantages, there are some drawbacks to be solved: the existing aluminum plastic film generally uses polypropylene or modified polypropylene as an innermost layer, but because polypropylene is a nonpolar substance, the adhesion between the polypropylene and aluminum is poor, and in the use process, the adhesive in the aluminum plastic film is limited by the working environment faced by the aluminum plastic film, and electrolyte corrosion and high temperature are always required to be faced, which clearly presents higher challenges for the performance of the aluminum plastic film.
Disclosure of Invention
The invention aims to provide an adhesive for an aluminum plastic film and a preparation process thereof, so as to solve the problems in the background technology.
In order to solve the technical problems, the invention provides the following technical scheme: a preparation process of an adhesive for an aluminum plastic film comprises the following steps:
s1, preparing modified polyimide bonding resin;
s11, dispersing bis (4-aminophenoxy) dimethylsilane into DMF under the nitrogen atmosphere, heating to 85-90 ℃, and mixing for 10-15min to prepare a bis (4-aminophenoxy) dimethylsilane solution; dispersing hexafluorodianhydride into DMF, carrying out ice water bath treatment to constant temperature, stirring and mixing for 5-8 hours, slowly and uniformly dropwise adding a bis (4-aminophenoxy) dimethylsilane solution for 5-8 hours, heating to 75-80 ℃ after the dropwise adding is finished, stirring and reacting for 18-24 hours, and removing redundant solvent by rotary evaporation to obtain fluorosilicone modified dianhydride;
s12, dispersing ethylene glycol diglycidyl ether into tetrahydrofuran in a nitrogen atmosphere, mixing for 15-30min to obtain ethylene glycol diglycidyl ether dispersion liquid, dispersing 4,4' -diaminodiphenyl disulfide into pure DMF, heating to 85-95 ℃, slowly dropwise adding the ethylene glycol diglycidyl ether dispersion liquid for 3-4.5h, continuing to react for 2-4h after the dropwise adding is finished, and removing redundant solvent by rotary evaporation to obtain polyether modified diamine;
s13, mixing the fluorosilicone modified dianhydride prepared in the step S11, dissolving in DMF, treating in an ice water bath under a nitrogen atmosphere to constant temperature, adding polyether modified diamine, heating to room temperature, reacting for 4-12h, adding octanediamine, heating to 40-50 ℃, and continuing to react for 4-8h to obtain a modified polyamide solution;
s14, carrying out imidization reaction on the modified polyamide solution prepared in the step S13 for 6-18h in a nitrogen atmosphere, cooling to room temperature, transferring the obtained product into distilled water, filtering, alternately washing for 2-3 times by using distilled water and absolute ethyl alcohol, and evaporating in vacuum to constant weight to obtain the modified polyimide bonding resin;
s2, dissolving the modified polyimide bonding resin prepared in the step S1 in an organic solvent, uniformly mixing, adding polyolefin resin, continuously mixing for 30-45min, and removing bubbles in vacuum to obtain the adhesive for the aluminum plastic film.
Further, the adhesive for the aluminum plastic film comprises the following components in parts by weight: 10-20% of modified polyimide bonding resin, 5-10% of polyolefin resin and the balance of organic solvent.
Further, the polyolefin resin is any one of low-density polyethylene and low-density polypropylene.
Further, the organic solvent is N-methyl pyrrolidone.
Further, in the step S11, the mass ratio of the bis (4-aminophenoxy) dimethylsilane to the hexafluorodianhydride is (2.7-3.5): 10.
further, in the step S12, the mass ratio of the ethylene glycol diglycidyl ether to the 4,4' -diaminodiphenyl disulfide is (0.38-0.45) in parts by weight: 1.
further, in the step S13, the mass ratio of the fluorosilicone modified dianhydride, the polyether modified diamine and the octanediamine is (10.5-12): (3-4): (0.6-0.75).
Further, in step S14, the imidization reaction temperature is 170 to 190 ℃.
Compared with the prior art, the invention has the following beneficial effects:
1. in order to improve the high temperature resistance and electrolyte corrosion resistance of the finally prepared aluminum plastic film, the modified polyimide bonding resin is prepared, the bonding of the plastic substrate and the aluminum foil layer is realized by utilizing the excellent bonding performance of polyimide, and the polyimide also has excellent thermal stability, so that the bonding strength and stability of the polyimide can be effectively maintained in a high temperature environment, and the aluminum plastic film can bear higher temperature in the processing and using processes;
2. in order to further improve the performance of the adhesive for the aluminum plastic film, the invention also limits the raw materials of the adhesive and the preparation process thereof; firstly, the invention uses the bi (4-aminophenoxy) dimethyl silane to react with the hexafluorodianhydride, and limits the reaction conditions, thus obtaining the dianhydride raw material containing fluorine-silicon element, wherein the fluorine and silicon elements have stronger electronegativity, can effectively improve the internal charge distribution in polyimide molecules, and enhances the polarity difference between molecules. The polyimide molecules are less prone to interact with water molecules, so that the water resistance of polyimide is improved, and fluorocarbon bonds and silicon-oxygen bonds have extremely high bond energy, and the chemical structural stability of the polyimide can be improved, so that the high-temperature performance and the water resistance of the polyimide material are further improved;
3. the invention prepares the fluorine-silicon modified dianhydride, which contains more benzene ring structures, and can cause the problem of reduced curing and crosslinking degree of the adhesive while increasing the high temperature resistance of the adhesive, so that the invention further prepares polyether modified diamine synthesized by using ethylene glycol diglycidyl ether and 4,4' -diaminodiphenyl disulfide for reaction aiming at the phenomenon.
Detailed Description
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.
Bis (4-aminophenoxy) dimethylsilane, hexafluorodianhydride, as used herein, is provided by Shanghai Honghai biomedical technologies, inc.; ethylene glycol diglycidyl ether, 4' -diaminodiphenyl disulfide, and octanediamine used were supplied by Shanghai Ala Biochemical technologies Co., ltd; the low-density polyethylene is 2801H0W type low-density polyethylene provided by Dongguan poly (N-vinyl acetate) plastic raw material Co., ltd;
example 1. A preparation process of an adhesive for an aluminum plastic film comprises the following steps:
s1, preparing modified polyimide bonding resin;
s11, dispersing 2.7 parts of bis (4-aminophenoxy) dimethylsilane into DMF (dimethyl formamide) in a nitrogen atmosphere, heating to 85 ℃, and mixing for 10 minutes to prepare a bis (4-aminophenoxy) dimethylsilane solution; dispersing 10 parts of hexafluorodianhydride into DMF (dimethyl formamide), carrying out ice water bath treatment to constant temperature, stirring and mixing for 5 hours, slowly and uniformly dropwise adding a bis (4-aminophenoxy) dimethylsilane solution for 5 hours, heating to 75 ℃ after the dropwise adding is finished, stirring and reacting for 18 hours, and removing redundant solvent by rotary evaporation to obtain fluorosilicone modified dianhydride;
s12, dispersing 0.38 part of ethylene glycol diglycidyl ether into tetrahydrofuran in a nitrogen atmosphere according to parts by weight, mixing for 15min to obtain ethylene glycol diglycidyl ether dispersion, dispersing 1 part of 4,4' -diaminodiphenyl disulfide into pure DMF, heating to 85 ℃, slowly dropwise adding the ethylene glycol diglycidyl ether dispersion for 3h, continuing to react for 2h after the dropwise adding is finished, and removing redundant solvent by rotary evaporation to obtain polyether modified diamine;
s13, according to parts by weight, dissolving 10.5 parts of the fluorosilicone modified dianhydride prepared in the step S11 in DMF, treating in an ice water bath under a nitrogen atmosphere until the temperature is constant, adding 3 parts of polyether modified diamine, heating to room temperature, reacting for 4 hours, adding 0.6 part of octanediamine, heating to 40 ℃, and continuing to react for 4 hours to obtain a modified polyamide solution;
s14, heating the modified polyamide solution prepared in the step S13 to 170 ℃ in a nitrogen atmosphere, carrying out imidization reaction for 6 hours, cooling to room temperature, transferring the obtained product into distilled water, filtering, alternately washing for 3 times by using distilled water and absolute ethyl alcohol, and evaporating in vacuum to constant weight to obtain the modified polyimide bonding resin;
s2, dissolving 10 parts of the modified polyimide bonding resin prepared in the step S1 into 85 parts of N-methyl pyrrolidone, uniformly mixing, adding 5 parts of low-density polyethylene resin, continuously mixing for 30min, and removing bubbles in vacuum to obtain the adhesive for the aluminum plastic film.
Example 2. A preparation process of an adhesive for an aluminum plastic film comprises the following steps:
compared with example 1, this example increases the addition amount of bis (4-aminophenoxy) dimethylsilane in step S11;
s1, preparing modified polyimide bonding resin;
s11, dispersing 3.5 parts of bis (4-aminophenoxy) dimethylsilane into DMF (dimethyl formamide) in a nitrogen atmosphere, heating to 85 ℃, and mixing for 10 minutes to prepare a bis (4-aminophenoxy) dimethylsilane solution; dispersing 10 parts of hexafluorodianhydride into DMF (dimethyl formamide), carrying out ice water bath treatment to constant temperature, stirring and mixing for 5 hours, slowly and uniformly dropwise adding a bis (4-aminophenoxy) dimethylsilane solution for 5 hours, heating to 75 ℃ after the dropwise adding is finished, stirring and reacting for 18 hours, and removing redundant solvent by rotary evaporation to obtain fluorosilicone modified dianhydride;
s12, dispersing 0.38 part of ethylene glycol diglycidyl ether into tetrahydrofuran in a nitrogen atmosphere according to parts by weight, mixing for 15min to obtain ethylene glycol diglycidyl ether dispersion, dispersing 1 part of 4,4' -diaminodiphenyl disulfide into pure DMF, heating to 85 ℃, slowly dropwise adding the ethylene glycol diglycidyl ether dispersion for 3h, continuing to react for 2h after the dropwise adding is finished, and removing redundant solvent by rotary evaporation to obtain polyether modified diamine;
s13, according to parts by weight, dissolving 10.5 parts of the fluorosilicone modified dianhydride prepared in the step S11 in DMF, treating in an ice water bath under a nitrogen atmosphere until the temperature is constant, adding 3 parts of polyether modified diamine, heating to room temperature, reacting for 4 hours, adding 0.6 part of octanediamine, heating to 40 ℃, and continuing to react for 4 hours to obtain a modified polyamide solution;
s14, heating the modified polyamide solution prepared in the step S13 to 170 ℃ in a nitrogen atmosphere, carrying out imidization reaction for 6 hours, cooling to room temperature, transferring the obtained product into distilled water, filtering, alternately washing for 3 times by using distilled water and absolute ethyl alcohol, and evaporating in vacuum to constant weight to obtain the modified polyimide bonding resin;
s2, dissolving 10 parts of the modified polyimide bonding resin prepared in the step S1 into 85 parts of N-methyl pyrrolidone, uniformly mixing, adding 5 parts of low-density polyethylene resin, continuously mixing for 30min, and removing bubbles in vacuum to obtain the adhesive for the aluminum plastic film.
Example 3. A preparation process of an adhesive for an aluminum plastic film comprises the following steps:
compared with example 1, this example increases the amount of ethylene glycol diglycidyl ether added in step S12;
s1, preparing modified polyimide bonding resin;
s11, dispersing 2.7 parts of bis (4-aminophenoxy) dimethylsilane into DMF (dimethyl formamide) in a nitrogen atmosphere, heating to 85 ℃, and mixing for 10 minutes to prepare a bis (4-aminophenoxy) dimethylsilane solution; dispersing 10 parts of hexafluorodianhydride into DMF (dimethyl formamide), carrying out ice water bath treatment to constant temperature, stirring and mixing for 5 hours, slowly and uniformly dropwise adding a bis (4-aminophenoxy) dimethylsilane solution for 5 hours, heating to 75 ℃ after the dropwise adding is finished, stirring and reacting for 18 hours, and removing redundant solvent by rotary evaporation to obtain fluorosilicone modified dianhydride;
s12, dispersing 0.45 part of ethylene glycol diglycidyl ether into tetrahydrofuran in a nitrogen atmosphere according to parts by weight, mixing for 15min to obtain ethylene glycol diglycidyl ether dispersion, dispersing 1 part of 4,4' -diaminodiphenyl disulfide into pure DMF, heating to 85 ℃, slowly dropwise adding the ethylene glycol diglycidyl ether dispersion for 3h, continuing to react for 2h after the dropwise adding is finished, and removing redundant solvent by rotary evaporation to obtain polyether modified diamine;
s13, according to parts by weight, dissolving 10.5 parts of the fluorosilicone modified dianhydride prepared in the step S11 in DMF, treating in an ice water bath under a nitrogen atmosphere until the temperature is constant, adding 3 parts of polyether modified diamine, heating to room temperature, reacting for 4 hours, adding 0.6 part of octanediamine, heating to 40 ℃, and continuing to react for 4 hours to obtain a modified polyamide solution;
s14, heating the modified polyamide solution prepared in the step S13 to 170 ℃ in a nitrogen atmosphere, carrying out imidization reaction for 6 hours, cooling to room temperature, transferring the obtained product into distilled water, filtering, alternately washing for 3 times by using distilled water and absolute ethyl alcohol, and evaporating in vacuum to constant weight to obtain the modified polyimide bonding resin;
s2, dissolving 10 parts of the modified polyimide bonding resin prepared in the step S1 into 85 parts of N-methyl pyrrolidone, uniformly mixing, adding 5 parts of low-density polyethylene resin, continuously mixing for 30min, and removing bubbles in vacuum to obtain the adhesive for the aluminum plastic film.
Example 4. A preparation process of an adhesive for an aluminum plastic film comprises the following steps:
compared with example 1, this example increases the addition amount of the modified polyimide bonding resin in step S2;
s1, preparing modified polyimide bonding resin;
s11, dispersing 2.7 parts of bis (4-aminophenoxy) dimethylsilane into DMF (dimethyl formamide) in a nitrogen atmosphere, heating to 85 ℃, and mixing for 10 minutes to prepare a bis (4-aminophenoxy) dimethylsilane solution; dispersing 10 parts of hexafluorodianhydride into DMF (dimethyl formamide), carrying out ice water bath treatment to constant temperature, stirring and mixing for 5 hours, slowly and uniformly dropwise adding a bis (4-aminophenoxy) dimethylsilane solution for 5 hours, heating to 75 ℃ after the dropwise adding is finished, stirring and reacting for 18 hours, and removing redundant solvent by rotary evaporation to obtain fluorosilicone modified dianhydride;
s12, dispersing 0.38 part of ethylene glycol diglycidyl ether into tetrahydrofuran in a nitrogen atmosphere according to parts by weight, mixing for 15min to obtain ethylene glycol diglycidyl ether dispersion, dispersing 1 part of 4,4' -diaminodiphenyl disulfide into pure DMF, heating to 85 ℃, slowly dropwise adding the ethylene glycol diglycidyl ether dispersion for 3h, continuing to react for 2h after the dropwise adding is finished, and removing redundant solvent by rotary evaporation to obtain polyether modified diamine;
s13, according to parts by weight, dissolving 10.5 parts of the fluorosilicone modified dianhydride prepared in the step S11 in DMF, treating in an ice water bath under a nitrogen atmosphere until the temperature is constant, adding 3 parts of polyether modified diamine, heating to room temperature, reacting for 4 hours, adding 0.6 part of octanediamine, heating to 40 ℃, and continuing to react for 4 hours to obtain a modified polyamide solution;
s14, heating the modified polyamide solution prepared in the step S13 to 170 ℃ in a nitrogen atmosphere, carrying out imidization reaction for 6 hours, cooling to room temperature, transferring the obtained product into distilled water, filtering, alternately washing for 3 times by using distilled water and absolute ethyl alcohol, and evaporating in vacuum to constant weight to obtain the modified polyimide bonding resin;
s2, dissolving 20 parts of the modified polyimide bonding resin prepared in the step S1 into 75 parts of N-methyl pyrrolidone, uniformly mixing, adding 5 parts of low-density polyethylene resin, continuously mixing for 30min, and removing bubbles in vacuum to obtain the adhesive for the aluminum plastic film.
Example 5. A preparation process of an adhesive for an aluminum plastic film comprises the following steps:
s1, preparing modified polyimide bonding resin;
s11, dispersing 3.5 parts of bis (4-aminophenoxy) dimethylsilane into DMF (dimethyl formamide) in a nitrogen atmosphere, heating to 90 ℃, and mixing for 15 minutes to prepare a bis (4-aminophenoxy) dimethylsilane solution; dispersing 10 parts of hexafluorodianhydride into DMF (dimethyl formamide), carrying out ice water bath treatment to constant temperature, stirring and mixing for 8 hours, slowly and uniformly dropwise adding a bis (4-aminophenoxy) dimethylsilane solution for 8 hours, heating to 80 ℃ after the dropwise adding is finished, stirring and reacting for 24 hours, and removing redundant solvent by rotary evaporation to obtain fluorosilicone modified dianhydride;
s12, dispersing 0.45 part of ethylene glycol diglycidyl ether into tetrahydrofuran in a nitrogen atmosphere according to parts by weight, mixing for 30min to obtain ethylene glycol diglycidyl ether dispersion, dispersing 1 part of 4,4' -diaminodiphenyl disulfide into pure DMF, heating to 95 ℃, slowly dropwise adding the ethylene glycol diglycidyl ether dispersion for 4.5h, continuing to react for 4h after the dropwise adding is finished, and removing redundant solvent by rotary evaporation to obtain polyether modified diamine;
s13, according to parts by weight, dissolving 12 parts of the fluorosilicone modified dianhydride prepared in the step S11 in DMF, treating in an ice water bath under a nitrogen atmosphere to constant temperature, adding 4 parts of polyether modified diamine, heating to room temperature, reacting for 12 hours, adding 0.75 part of octanediamine, heating to 40 ℃, and continuing to react for 4 hours to obtain a modified polyamide solution;
s14, heating the modified polyamide solution prepared in the step S13 to 190 ℃ in a nitrogen atmosphere, carrying out imidization reaction for 18 hours, cooling to room temperature, transferring the obtained product into distilled water, filtering, alternately washing for 3 times by using distilled water and absolute ethyl alcohol, and evaporating in vacuum to constant weight to obtain the modified polyimide bonding resin;
s2, dissolving 20 parts of the modified polyimide bonding resin prepared in the step S1 in 70 parts of N-methyl pyrrolidone, uniformly mixing, adding 10 parts of low-density polyethylene resin, continuously mixing for 30min, and removing bubbles in vacuum to obtain the adhesive for the aluminum plastic film.
Comparative example 1. A preparation process of an adhesive for an aluminum plastic film, comprising the following steps:
in comparison to example 1, the polyether modified diamine was not prepared in this example;
s1, preparing modified polyimide bonding resin;
s11, dispersing 2.7 parts of bis (4-aminophenoxy) dimethylsilane into DMF (dimethyl formamide) in a nitrogen atmosphere, heating to 85 ℃, and mixing for 10 minutes to prepare a bis (4-aminophenoxy) dimethylsilane solution; dispersing 10 parts of hexafluorodianhydride into DMF (dimethyl formamide), carrying out ice water bath treatment to constant temperature, stirring and mixing for 5 hours, slowly and uniformly dropwise adding a bis (4-aminophenoxy) dimethylsilane solution for 5 hours, heating to 75 ℃ after the dropwise adding is finished, stirring and reacting for 18 hours, and removing redundant solvent by rotary evaporation to obtain fluorosilicone modified dianhydride;
s12, according to parts by weight, dissolving 10.5 parts of the fluorosilicone modified dianhydride prepared in the step S11 in DMF, treating in an ice water bath to constant temperature under a nitrogen atmosphere, adding 1.2 parts of octanediamine, heating to 40 ℃, and continuing to react for 4 hours to obtain a modified polyamide solution;
s14, heating the modified polyamide solution prepared in the step S12 to 170 ℃ in a nitrogen atmosphere, carrying out imidization reaction for 6 hours, cooling to room temperature, transferring the obtained product into distilled water, filtering, alternately washing for 3 times by using distilled water and absolute ethyl alcohol, and evaporating in vacuum to constant weight to obtain the modified polyimide bonding resin;
s2, dissolving 10 parts of the modified polyimide bonding resin prepared in the step S1 into 85 parts of N-methyl pyrrolidone, uniformly mixing, adding 5 parts of low-density polyethylene resin, continuously mixing for 30min, and removing bubbles in vacuum to obtain the adhesive for the aluminum plastic film.
Comparative example 2. A preparation process of an adhesive for an aluminum plastic film, comprising the following steps:
in comparison with example 1, the present comparative example did not prepare fluorosilicone-modified dianhydride, but used only pyromellitic dianhydride instead of the equivalent amount;
s1, preparing modified polyimide bonding resin;
s11, dispersing 0.38 part of ethylene glycol diglycidyl ether into tetrahydrofuran in a nitrogen atmosphere according to parts by weight, mixing for 15min to obtain ethylene glycol diglycidyl ether dispersion, dispersing 1 part of 4,4' -diaminodiphenyl disulfide into pure DMF, heating to 85 ℃, slowly dropwise adding the ethylene glycol diglycidyl ether dispersion for 3h, continuing to react for 2h after the dropwise adding is finished, and removing redundant solvent by rotary evaporation to obtain polyether modified diamine;
s12, according to parts by weight, 2.18 parts of pyromellitic dianhydride is dissolved in DMF, under the nitrogen atmosphere, 3 parts of polyether modified diamine is added after the ice water bath treatment is carried out to constant temperature, the temperature is raised to room temperature, 0.6 part of octanediamine is added after the reaction is carried out for 4 hours, the temperature is raised to 40 ℃, and the reaction is continued for 4 hours, thus obtaining modified polyamide solution;
s13, heating the modified polyamide solution prepared in the step S12 to 170 ℃ in a nitrogen atmosphere, carrying out imidization reaction for 6 hours, cooling to room temperature, transferring the obtained product into distilled water, filtering, alternately washing for 3 times by using distilled water and absolute ethyl alcohol, and evaporating in vacuum to constant weight to obtain the modified polyimide bonding resin;
s2, dissolving 10 parts of the modified polyimide bonding resin prepared in the step S1 into 85 parts of N-methyl pyrrolidone, uniformly mixing, adding 5 parts of low-density polyethylene resin, continuously mixing for 30min, and removing bubbles in vacuum to obtain the adhesive for the aluminum plastic film.
And (3) detection: the adhesive prepared in examples 1-5 and comparative examples 1-2 was uniformly coated on the bright side of a 40 μm-thick passivated aluminum foil in an amount of 3g/m 2 Compounding a PP (polypropylene) base film with the thickness of 40 micrometers to an aluminum foil layer in a hot-pressing mode, wherein the hot-pressing temperature is 100 ℃, and the hot-pressing pressure is 0.4MPa; cutting the test sample into test samples with the width of 15 mm and the length of 100mm, and testing the peeling strength by using a universal tensile tester; then the sample is soaked into electrolyte at 85 ℃ and the peel strength is tested after 24 hours, 7 days and 28 days respectively, wherein the electrolyte contains 1mol/L lithium hexafluorophosphate; the test pieces were subjected to heat peeling strength test according to GB/T8808-1988 at 120℃and peeling stretching speed of 200mm/min in a stretching direction 180 DEG to the non-peeled portion; the detection results are shown in the following table;
finally, it should be noted that: the foregoing description is only a preferred embodiment of the present invention, and the present invention is not limited thereto, but it is to be understood that modifications and equivalents of some of the technical features described in the foregoing embodiments may be made by those skilled in the art, although the present invention has been described in detail with reference to the foregoing embodiments. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (8)
1. The preparation process of the adhesive for the aluminum plastic film is characterized by comprising the following steps of:
s1, preparing modified polyimide bonding resin;
s11, dispersing bis (4-aminophenoxy) dimethylsilane into DMF under the nitrogen atmosphere, heating to 85-90 ℃, and mixing for 10-15min to prepare a bis (4-aminophenoxy) dimethylsilane solution; dispersing hexafluorodianhydride into DMF, carrying out ice water bath treatment to constant temperature, stirring and mixing for 5-8 hours, slowly and uniformly dropwise adding a bis (4-aminophenoxy) dimethylsilane solution for 5-8 hours, heating to 75-80 ℃ after the dropwise adding is finished, stirring and reacting for 18-24 hours, and removing redundant solvent by rotary evaporation to obtain fluorosilicone modified dianhydride;
s12, dispersing ethylene glycol diglycidyl ether into tetrahydrofuran in a nitrogen atmosphere, mixing for 15-30min to obtain ethylene glycol diglycidyl ether dispersion liquid, dispersing 4,4' -diaminodiphenyl disulfide into pure DMF, heating to 85-95 ℃, slowly dropwise adding the ethylene glycol diglycidyl ether dispersion liquid for 3-4.5h, continuing to react for 2-4h after the dropwise adding is finished, and removing redundant solvent by rotary evaporation to obtain polyether modified diamine;
s13, dissolving the fluorosilicone modified dianhydride prepared in the step S11 in DMF, treating in an ice water bath under a nitrogen atmosphere to a constant temperature, adding polyether modified diamine, heating to room temperature, reacting for 4-12h, adding octanediamine, heating to 40-50 ℃, and continuing to react for 4-8h to obtain a modified polyamide solution;
s14, carrying out imidization reaction on the modified polyamide solution prepared in the step S13 for 6-18h in a nitrogen atmosphere, cooling to room temperature, transferring the obtained product into distilled water, filtering, alternately washing for 2-3 times by using distilled water and absolute ethyl alcohol, and evaporating in vacuum to constant weight to obtain the modified polyimide bonding resin;
s2, dissolving the modified polyimide bonding resin prepared in the step S1 in an organic solvent, uniformly mixing, adding polyolefin resin, continuously mixing for 30-45min, and removing bubbles in vacuum to obtain the adhesive for the aluminum plastic film.
2. The preparation process of the adhesive for the aluminum plastic film according to claim 1, which is characterized in that: the adhesive for the aluminum plastic film comprises the following components in parts by weight: 10-20% of modified polyimide bonding resin, 5-10% of polyolefin resin and the balance of organic solvent.
3. The preparation process of the adhesive for the aluminum plastic film according to claim 1, which is characterized in that: the polyolefin resin is any one of low-density polyethylene and low-density polypropylene.
4. The preparation process of the adhesive for the aluminum plastic film according to claim 1, which is characterized in that: the organic solvent is N-methyl pyrrolidone.
5. The preparation process of the adhesive for the aluminum plastic film according to claim 1, which is characterized in that: in the step S11, the mass ratio of the bis (4-aminophenoxy) dimethylsilane to the hexafluorodianhydride is (2.7-3.5) according to the weight parts: 10.
6. the preparation process of the adhesive for the aluminum plastic film according to claim 1, which is characterized in that: in the step S12, the mass ratio of the ethylene glycol diglycidyl ether to the 4,4' -diaminodiphenyl disulfide is (0.38-0.45) according to the weight part: 1.
7. the preparation process of the adhesive for the aluminum plastic film according to claim 1, which is characterized in that: in the step S13, the mass ratio of the fluorine-silicon modified dianhydride to the polyether modified diamine to the octanediamine is (10.5-12): (3-4): (0.6-0.75).
8. The preparation process of the adhesive for the aluminum plastic film according to claim 1, which is characterized in that: in step S14, the imidization reaction temperature is 170-190 ℃.
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| CA1331387C (en) * | 1988-11-14 | 1994-08-09 | Chung J. Lee | Polyimidesiloxanes and methods for their preparation and use |
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| CN106010420A (en) * | 2015-03-30 | 2016-10-12 | 荒川化学工业株式会社 | Polyimide-based adhesive, film adhesive, adhesive layer, adhesive sheet, copper-clad laminate, wiring board and its manufacturing method |
| US20180340100A1 (en) * | 2015-12-13 | 2018-11-29 | International Business Machines Corporation | Enhanced adhesive materials and processes for 3d applications |
| CN116691097A (en) * | 2023-07-07 | 2023-09-05 | 上海人民塑料印刷厂有限公司 | High-barrier aluminum-plastic packaging film and preparation process thereof |
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2024
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Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CA1331387C (en) * | 1988-11-14 | 1994-08-09 | Chung J. Lee | Polyimidesiloxanes and methods for their preparation and use |
| CN1092448A (en) * | 1993-03-16 | 1994-09-21 | 西方化学公司 | Three-layer polyimidesiloxane adhesive tape |
| JP2004146620A (en) * | 2002-10-25 | 2004-05-20 | Sumitomo Bakelite Co Ltd | Film adhesive and semiconductor adhesive tape |
| CN106010420A (en) * | 2015-03-30 | 2016-10-12 | 荒川化学工业株式会社 | Polyimide-based adhesive, film adhesive, adhesive layer, adhesive sheet, copper-clad laminate, wiring board and its manufacturing method |
| US20180340100A1 (en) * | 2015-12-13 | 2018-11-29 | International Business Machines Corporation | Enhanced adhesive materials and processes for 3d applications |
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