CN114479708A - Preparation method of epoxy resin-based heat-conducting heat-resistant electric-conducting adhesive film - Google Patents
Preparation method of epoxy resin-based heat-conducting heat-resistant electric-conducting adhesive film Download PDFInfo
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- CN114479708A CN114479708A CN202210255033.5A CN202210255033A CN114479708A CN 114479708 A CN114479708 A CN 114479708A CN 202210255033 A CN202210255033 A CN 202210255033A CN 114479708 A CN114479708 A CN 114479708A
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- epoxy resin
- adhesive film
- heat
- conductive adhesive
- based heat
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- 239000003822 epoxy resin Substances 0.000 title claims abstract description 61
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 61
- 239000002313 adhesive film Substances 0.000 title claims abstract description 45
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 80
- 230000003712 anti-aging effect Effects 0.000 claims abstract description 35
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000007822 coupling agent Substances 0.000 claims abstract description 14
- 239000003085 diluting agent Substances 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 48
- 238000002156 mixing Methods 0.000 claims description 30
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 28
- 238000003756 stirring Methods 0.000 claims description 28
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 26
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical class [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 20
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 claims description 20
- 229910021389 graphene Inorganic materials 0.000 claims description 17
- JOLVYUIAMRUBRK-UHFFFAOYSA-N 11',12',14',15'-Tetradehydro(Z,Z-)-3-(8-Pentadecenyl)phenol Natural products OC1=CC=CC(CCCCCCCC=CCC=CCC=C)=C1 JOLVYUIAMRUBRK-UHFFFAOYSA-N 0.000 claims description 16
- YLKVIMNNMLKUGJ-UHFFFAOYSA-N 3-Delta8-pentadecenylphenol Natural products CCCCCCC=CCCCCCCCC1=CC=CC(O)=C1 YLKVIMNNMLKUGJ-UHFFFAOYSA-N 0.000 claims description 16
- JOLVYUIAMRUBRK-UTOQUPLUSA-N Cardanol Chemical compound OC1=CC=CC(CCCCCCC\C=C/C\C=C/CC=C)=C1 JOLVYUIAMRUBRK-UTOQUPLUSA-N 0.000 claims description 16
- FAYVLNWNMNHXGA-UHFFFAOYSA-N Cardanoldiene Natural products CCCC=CCC=CCCCCCCCC1=CC=CC(O)=C1 FAYVLNWNMNHXGA-UHFFFAOYSA-N 0.000 claims description 16
- PTFIPECGHSYQNR-UHFFFAOYSA-N cardanol Natural products CCCCCCCCCCCCCCCC1=CC=CC(O)=C1 PTFIPECGHSYQNR-UHFFFAOYSA-N 0.000 claims description 16
- 239000007864 aqueous solution Substances 0.000 claims description 15
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 claims description 14
- 238000001035 drying Methods 0.000 claims description 13
- BQZKNPPVHYOJLR-UHFFFAOYSA-N 1,1-dibromo-2,2-dimethylpropane Chemical compound CC(C)(C)C(Br)Br BQZKNPPVHYOJLR-UHFFFAOYSA-N 0.000 claims description 12
- NWHNXXMYEICZAT-UHFFFAOYSA-N 1,2,2,6,6-pentamethylpiperidin-4-ol Chemical compound CN1C(C)(C)CC(O)CC1(C)C NWHNXXMYEICZAT-UHFFFAOYSA-N 0.000 claims description 12
- 238000001816 cooling Methods 0.000 claims description 11
- 238000010992 reflux Methods 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 10
- 229910002804 graphite Inorganic materials 0.000 claims description 10
- 239000010439 graphite Substances 0.000 claims description 10
- 229960003506 piperazine hexahydrate Drugs 0.000 claims description 10
- AVRVZRUEXIEGMP-UHFFFAOYSA-N piperazine;hexahydrate Chemical compound O.O.O.O.O.O.C1CNCCN1 AVRVZRUEXIEGMP-UHFFFAOYSA-N 0.000 claims description 10
- 238000000227 grinding Methods 0.000 claims description 7
- 239000012286 potassium permanganate Substances 0.000 claims description 7
- 238000005119 centrifugation Methods 0.000 claims description 6
- 238000004108 freeze drying Methods 0.000 claims description 6
- 238000010907 mechanical stirring Methods 0.000 claims description 6
- 238000000967 suction filtration Methods 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 12
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract description 10
- 230000003647 oxidation Effects 0.000 abstract description 10
- 238000007254 oxidation reaction Methods 0.000 abstract description 10
- 238000004806 packaging method and process Methods 0.000 abstract description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract description 6
- 239000000853 adhesive Substances 0.000 abstract description 5
- 230000001070 adhesive effect Effects 0.000 abstract description 5
- 230000032683 aging Effects 0.000 abstract description 4
- 229910052709 silver Inorganic materials 0.000 abstract description 4
- 239000004332 silver Substances 0.000 abstract description 4
- 238000013461 design Methods 0.000 abstract description 3
- 230000002195 synergetic effect Effects 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000000203 mixture Substances 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 13
- 238000002390 rotary evaporation Methods 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 238000007792 addition Methods 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 239000002274 desiccant Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000008098 formaldehyde solution Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- 238000004821 distillation Methods 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 229960005141 piperazine Drugs 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 230000009194 climbing Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- LQBJWKCYZGMFEV-UHFFFAOYSA-N lead tin Chemical compound [Sn].[Pb] LQBJWKCYZGMFEV-UHFFFAOYSA-N 0.000 description 3
- 229910000679 solder Inorganic materials 0.000 description 3
- 238000005336 cracking Methods 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- YCOZIPAWZNQLMR-UHFFFAOYSA-N pentadecane Chemical compound CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 244000226021 Anacardium occidentale Species 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000020226 cashew nut Nutrition 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 1
- -1 good flexibility Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
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
- 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
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/62—Alcohols or phenols
- C08G59/621—Phenols
- C08G59/623—Aminophenols
-
- 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
- C09J11/04—Non-macromolecular additives inorganic
-
- 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
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
- C09J9/02—Electrically-conducting adhesives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/08—Metals
- C08K2003/0806—Silver
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K2201/00—Specific properties of additives
- C08K2201/001—Conductive additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Epoxy Resins (AREA)
Abstract
The invention discloses a preparation method of an epoxy resin-based heat-conducting heat-resistant conductive adhesive film, which relates to the field of epoxy resin-based heat-conducting heat-resistant conductive adhesive films, wherein an epoxy resin and a conductive accelerator are uniformly mixed, fully ground, added with silver powder, added with a diluent, a coupling agent and an anti-aging agent, uniformly mixed, added with a curing agent and uniformly mixed, and vacuumized to obtain the epoxy resin-based heat-conducting heat-resistant conductive adhesive film, so that the problems that the design requirements cannot be met when a conductive silver adhesive material is used for packaging and the epoxy resin-based material is cracked and deformed due to thermal oxidation aging are solved; through the synergistic effect of the epoxy resin, the conductive accelerator, the silver powder and the anti-aging agent, the epoxy resin-based heat-conducting heat-resistant conductive adhesive film has good manufacturability in application, the packaging of thinner and smaller chips is realized, and meanwhile, piperazine and piperidine are integrated in the same molecule by adopting a chemical synthesis method, so that the epoxy resin-based heat-conducting heat-resistant conductive adhesive film has a more efficient anti-aging effect.
Description
Technical Field
The invention relates to the field of epoxy resin-based heat-conducting heat-resistant electric-conductive films, in particular to a preparation method of an epoxy resin-based heat-conducting heat-resistant electric-conductive film.
Background
With the development of social science and technology, the pursuit of high-tech products by human beings is more and more intense, and products are continuously required to realize more functions on smaller and smaller external dimensions, so that semiconductor packaging needs to find a reliable solution with thinner, smaller and higher packaging density, and the solution is partly to provide materials used in manufacturing subminiature semiconductor devices;
in the traditional chip packaging connection, materials such as lead-tin solder or conductive silver adhesive are generally used, because the minimum pitch of lead-tin solder is only 0.65mm when the lead-tin solder is used for packaging, when the conductive silver adhesive material is used for packaging, the phenomenon of chip side glue climbing and chip inclination is easily caused, the further miniaturization of chip packaging is seriously influenced, the design requirement cannot be met, and the epoxy resin base material is easily subjected to the action of thermal oxidation in the using process, so that the cracking deformation caused by thermal oxidation aging of the electric adhesive film is caused, and the service life of the electric adhesive film is shortened;
in view of the technical problem in this respect, a solution is now proposed.
Disclosure of Invention
In order to overcome the technical problems, the invention aims to provide a preparation method of an epoxy resin-based heat-conducting heat-resistant electric-conducting adhesive film, which comprises the following steps:
(1) uniformly mixing epoxy resin and a conductive accelerator, fully grinding, adding silver powder, uniformly mixing, vacuumizing, adding a diluent, a coupling agent and an anti-aging agent, uniformly mixing, adding a curing agent, uniformly mixing, and vacuumizing to obtain the epoxy resin-based heat-conducting heat-resistant conductive adhesive film, so that the problems that when a conductive silver adhesive material is used for packaging, the side edge of a chip is subjected to adhesive climbing, the chip is inclined, and the design requirements cannot be met and the cracking and deformation caused by thermal oxidation aging of the epoxy resin-based material are solved;
(2) adding concentrated H into the beaker2SO4Then adding H3PO4And dried graphite, adding KMnO4Adding H to the system202Obtaining graphene oxide, and mixing piperazine hexahydrate and methyl propylenePropyl gallate and graphene oxide are added into a three-neck flask to obtain an intermediate A, the intermediate A, 1, 2, 2, 6, 6-pentamethyl-4-piperidinol, anhydrous toluene and sodium methoxide are added into the three-neck flask to obtain the anti-aging agent, and the problems that an epoxy resin base material is easily subjected to thermal oxidation in the using process, so that an electric adhesive film is cracked and deformed due to thermal oxidation aging, and the service life of the electric adhesive film is shortened are solved;
(3) adding cardanol, dibromoneopentane, a saturated NaOH aqueous solution and benzyltriethylammonium chloride into a four-neck flask, drying to obtain an intermediate C, adding the intermediate C and diethylenetriamine into a three-neck flask, and dropwise adding a formaldehyde aqueous solution to obtain the curing agent.
The purpose of the invention can be realized by the following technical scheme:
a preparation method of an epoxy resin-based heat-conducting heat-resistant electric-conductive adhesive film comprises the following components in parts by weight:
10-15 parts of epoxy resin, 1-2 parts of diluent, 1-5 parts of curing agent, 1-5 parts of coupling agent, 1-3 parts of conductive accelerator, 3-5 parts of anti-aging agent and 120 parts of silver powder;
the epoxy resin-based heat-conducting heat-resistant electric-conductive adhesive film is prepared by the following steps:
s1: uniformly mixing the epoxy resin and the conductive accelerant, and fully grinding;
s2: adding silver powder, mixing uniformly, vacuumizing, adding a diluent, a coupling agent and an anti-aging agent, and mixing uniformly;
s3: adding a curing agent, uniformly mixing, and vacuumizing to obtain the epoxy resin-based heat-conducting heat-resistant electric-conducting adhesive film;
the anti-aging agent is prepared by the following steps:
s11: under ice-bath conditions, concentrated H was added to the beaker2SO4Adding H when the temperature is reduced to 0-5 DEG C3PO4Mixing with dried graphite, stirring for 30-60min, adding KMnO4Continuously stirring for 10-20min, stirring at constant temperature of 40-45 ℃ for 2-4h, and continuously stirring at 95-105 ℃ for 30-40min, naturally cooling to 60-70 deg.C, and adding H into the system202Cooling to room temperature, then carrying out suction filtration, centrifugation and freeze drying to obtain graphene oxide;
s12: adding piperazine hexahydrate, propyl methacrylate and graphene oxide into a three-neck flask, stirring at room temperature for 20-30min, drying by taking ethyl acetate as an extracting agent and anhydrous sodium sulfate as a drying agent, and performing rotary evaporation to remove redundant reaction raw materials, namely propyl methacrylate and ethyl acetate serving as the extracting agent to obtain an intermediate A;
the chemical reaction formula is as follows:
s13: adding the intermediate A, 1, 2, 2, 6, 6-pentamethyl-4-piperidinol, anhydrous toluene and sodium methoxide into a three-neck flask, carrying out reflux reaction at the temperature of 150-.
The chemical reaction formula is as follows:
as a further scheme of the invention: rich H in step S112SO4、H3PO4Graphite and KMnO4The dosage ratio of (A) is 46 mL: 4mL of: 1 g: 5g of said compound H202Is 5 percent.
As a further scheme of the invention: in the step S12, the dosage ratio of piperazine hexahydrate, propyl methacrylate to graphene oxide is 1.9423 g: 2.1524 g: 10 g.
As a further scheme of the invention: in the step S13, the dosage ratio of the intermediate A, the 1, 2, 2, 6, 6-pentamethyl-4-piperidinol and the anhydrous toluene is 0.2582 g: 0.3766 g: 10mL, wherein the using amount of the sodium methoxide is 2% of the total mass of the intermediate A, the 1, 2, 2, 6, 6-pentamethyl-4-piperidinol and the anhydrous toluene.
As a further scheme of the invention: the curing agent is prepared by the following steps:
s51: adding cardanol, dibromoneopentane, saturated NaOH aqueous solution and benzyltriethylammonium chloride into a four-neck flask provided with a mechanical stirring paddle, a thermometer and a reflux condenser, and adding N2Heating to the temperature of 120-150 ℃ in the atmosphere, continuing for 6-8h, filtering off sodium salt generated by the reaction by using silica powder, then performing reduced pressure rotary evaporation by using a rotary evaporator, and drying to obtain an intermediate C;
s52: adding the intermediate C and diethylenetriamine into a three-neck flask provided with a stirring magneton, a water separator and a thermometer, heating to 80-90 ℃, reacting for 30-40min, dropwise adding aqueous formaldehyde solution, controlling the dropwise adding speed to be 1-2 drops/s, reacting for 4-5h, heating to 120-130 ℃, and reacting for 3-4h to obtain the curing agent.
As a further scheme of the invention: in the step S51, the use amount ratio of cardanol, dibromoneopentane to a saturated NaOH aqueous solution is 30.2 g: 12.1 g: 100mL, wherein the mass of the benzyltriethylammonium chloride is 0.15% of the total mass of the cardanol, the dibromoneopentane and the saturated NaOH aqueous solution.
As a further scheme of the invention: in the step S52, the dosage ratio of the intermediate C, the diethylenetriamine and the formaldehyde aqueous solution is 32.2 g: 5.2 g: 8.1g, wherein the mass fraction of the formaldehyde aqueous solution is 37%.
The invention has the following beneficial effects:
(1) the epoxy resin-based heat-conducting heat-resisting and electricity-conducting adhesive film has good manufacturability in application through the synergistic effect of the epoxy resin, the electricity-conducting accelerator, the silver powder and the anti-aging agent, and can realize the encapsulation of thinner and smaller chips;
(2) adding concentrated H into the beaker2SO4Then adding H3PO4And dried graphite, adding KMnO4Adding H to the system202The anti-aging agent is obtained by adding piperazine hexahydrate, propyl methacrylate and graphene oxide into a three-neck flask to obtain an intermediate A, adding the intermediate A, 1, 2, 2, 6, 6-pentamethyl-4-piperidinol, anhydrous toluene and sodium methoxide into the three-neck flask to obtain the anti-aging agent, wherein the anti-aging agent not only has good light stability effect, but also has good thermal oxidation resistance, the light stability of the anti-aging agent is 2-4 times higher than that of an ultraviolet absorbent, singlet oxygen can be quenched, hydroperoxide is decomposed to generate a stable functional group NO, the NO can eliminate macromolecular free radicals and thermal oxidation resistant free radicals generated in the oxidation process, the anti-aging agent can be regenerated in the reaction process, the piperazine has low alkalinity, has weak interaction with other acidic components, is good in compatibility with resin and has good oxidation effect, by utilizing the characteristic of piperazine, piperazine and piperidine are integrated in the same molecule by adopting a chemical synthesis method, so that the piperazine and piperidine have more efficient anti-aging effect;
(3) adding cardanol, dibromoneopentane, a saturated NaOH aqueous solution and benzyltriethylammonium chloride into a four-neck flask, drying to obtain an intermediate C, adding the intermediate C and diethylenetriamine into a three-neck flask, dropwise adding a formaldehyde aqueous solution to obtain the curing agent, wherein the cardanol is a main component of natural cashew shell oil and is a phenol derivative with a pentadecane unsaturated long chain in a meta position, the side chain of the cardanol is a C15 cis structure containing 0-3 unsaturated bonds, and the C15 long chain structure enables the cardanol to have the characteristics of aliphatic compounds such as good flexibility, excellent hydrophobicity and low permeability and the like and the high temperature resistance characteristic of aromatic compounds, polar hydroxyl can provide wetting and activity of a system on a contact surface, and the cardanol with a unique unsaturated long chain is applied to modified epoxy resin to play a toughening role, the epoxy resin can be cured on a moist surface even with water, the phase separation phenomenon occurs in the curing process, the mechanism similar to that of toughening epoxy by natural rubber and thermoplastic resin is adopted, the impact strength of the epoxy resin material is improved, and the phenomenon of side glue climbing is avoided by the rapid curing of the epoxy resin.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1:
the embodiment is an epoxy resin-based heat-conducting heat-resistant electric-conductive adhesive film, which comprises the following components in parts by weight:
12 parts of epoxy resin, 2 parts of diluent, 5 parts of curing agent, 5 parts of coupling agent, 3 parts of conductive accelerator, 5 parts of anti-aging agent and 120 parts of silver powder;
the epoxy resin-based heat-conducting heat-resistant electric-conductive adhesive film is prepared by the following steps:
s1: uniformly mixing the epoxy resin and the conductive accelerant, and fully grinding;
s2: adding silver powder, mixing uniformly, vacuumizing, adding a diluent, a coupling agent and an anti-aging agent, and mixing uniformly;
s3: adding a curing agent, uniformly mixing, and vacuumizing to obtain the epoxy resin-based heat-conducting heat-resistant electric-conducting adhesive film;
the anti-aging agent is prepared by the following steps:
s11: under ice-bath conditions, 46mL of concentrated H was added to the beaker2SO4Adding 4mL of H when the temperature is reduced to 5 DEG C3PO4And 1g of dried graphite, stirred for 60min, 5g of KMnO was added4Stirring for 20min, stirring at 40 deg.C for 2 hr, stirring at 105 deg.C for 40min, naturally cooling to 70 deg.C, and adding 5% H202Cooling to room temperature, then carrying out suction filtration, centrifugation and freeze drying to obtain graphene oxide;
s12: adding 1.9423g of piperazine hexahydrate, 2.1524g of propyl methacrylate and 10g of graphene oxide into a three-neck flask, stirring at room temperature for 20min, drying by using ethyl acetate as an extracting agent and anhydrous sodium sulfate as a drying agent, and performing rotary evaporation to remove redundant reaction raw materials of propyl methacrylate and ethyl acetate serving as the extracting agent to obtain an intermediate A;
s13: adding 0.2582g of intermediate A, 0.3766g of 1, 2, 2, 6, 6-pentamethyl-4-piperidinol, 10mL of anhydrous toluene and 0.025g of sodium methoxide into a three-neck flask, carrying out reflux reaction at 180 ℃ for 12h, removing toluene by adopting a reduced pressure distillation method, washing with hot water to remove sodium methoxide, taking ethyl acetate as an extracting agent, collecting an organic phase, concentrating and recrystallizing to obtain the anti-aging agent;
the curing agent is prepared by the following steps:
s51: a four-necked flask equipped with a mechanical stirring paddle, a thermometer and a reflux condenser was charged with 30.2g of cardanol, 12.1g of dibromoneopentane, 100mL of a saturated aqueous NaOH solution and benzyltriethylammonium chloride, and the mixture was stirred in a nitrogen atmosphere2Heating to 120 ℃ in the atmosphere, continuing for 6 hours, filtering off sodium salt generated in the reaction by using silica powder, then carrying out reduced pressure rotary evaporation by using a rotary evaporator, and drying to obtain an intermediate C;
s52: 32.2g of the intermediate C and 5.2g of diethylenetriamine are added into a three-neck flask provided with a stirring magneton, a water separator and a thermometer, the mixture is heated to 90 ℃ and reacts for 30min, 8.1g of aqueous formaldehyde solution is added dropwise, the dropping speed is controlled to be 2 drops/s, the mixture is heated to 120 ℃ after reacting for 4h, and the curing agent is obtained after reacting for 3 h.
Example 2:
the embodiment is an epoxy resin-based heat-conducting heat-resistant electric-conductive adhesive film, which comprises the following components in parts by weight:
10 parts of epoxy resin, 1 part of diluent, 1 part of curing agent, 5 parts of coupling agent, 3 parts of conductive accelerator, 5 parts of anti-aging agent and 100 parts of silver powder;
the epoxy resin-based heat-conducting heat-resistant electric-conductive adhesive film is prepared by the following steps:
s1: uniformly mixing the epoxy resin and the conductive accelerant, and fully grinding;
s2: adding silver powder, mixing uniformly, vacuumizing, adding a diluent, a coupling agent and an anti-aging agent, and mixing uniformly;
s3: adding a curing agent, uniformly mixing, and vacuumizing to obtain the epoxy resin-based heat-conducting heat-resistant electric-conducting adhesive film;
the anti-aging agent is prepared by the following steps:
s11: under ice-bath conditions, 46mL of concentrated H was added to the beaker2SO4Adding 4mL of H when the temperature is reduced to 0 DEG C3PO4And 1g of dried graphite, stirred for 30min, 5g of KMnO was added4Stirring for 20min, stirring at 40 deg.C for 2H, stirring at 95 deg.C for 30min, cooling to 60 deg.C, and adding 5% H202Cooling to room temperature, then carrying out suction filtration, centrifugation and freeze drying to obtain graphene oxide;
s12: adding 1.9423g of piperazine hexahydrate, 2.1524g of propyl methacrylate and 10g of graphene oxide into a three-neck flask, stirring at room temperature for 20min, drying by using ethyl acetate as an extracting agent and anhydrous sodium sulfate as a drying agent, and performing rotary evaporation to remove redundant reaction raw materials of propyl methacrylate and ethyl acetate serving as the extracting agent to obtain an intermediate A;
s13: adding 0.2582g of intermediate A, 0.3766g of 1, 2, 2, 6, 6-pentamethyl-4-piperidinol, 10mL of anhydrous toluene and 0.025g of sodium methoxide into a three-neck flask, refluxing and reacting at 150 ℃ for 12h, removing toluene by adopting a reduced pressure distillation method, washing with hot water to remove sodium methoxide, taking ethyl acetate as an extracting agent, collecting an organic phase, concentrating and recrystallizing to obtain the anti-aging agent;
the curing agent is prepared by the following steps:
s51: a four-necked flask equipped with a mechanical stirring paddle, a thermometer and a reflux condenser was charged with 30.2g of cardanol, 12.1g of dibromoneopentane, 100mL of a saturated aqueous NaOH solution and benzyltriethylammonium chloride, and the mixture was stirred in a nitrogen atmosphere2Heating to 120 ℃ in the atmosphere, continuing for 6 hours, filtering off sodium salt generated in the reaction by using silica powder, then carrying out reduced pressure rotary evaporation by using a rotary evaporator, and drying to obtain an intermediate C;
s52: 32.2g of the intermediate C and 5.2g of diethylenetriamine are added into a three-neck flask provided with a stirring magneton, a water separator and a thermometer, the mixture is heated to 80 ℃ and reacts for 30min, 8.1g of aqueous formaldehyde solution is added dropwise, the dropwise adding speed is controlled to be 1 drop/s, the mixture is heated to 120 ℃ after reacting for 4h, and the curing agent is obtained after reacting for 3 h.
Example 3:
the embodiment is an epoxy resin-based heat-conducting heat-resistant electric-conductive adhesive film, which comprises the following components in parts by weight:
10 parts of epoxy resin, 2 parts of diluent, 5 parts of curing agent, 5 parts of coupling agent, 3 parts of conductive accelerator, 5 parts of anti-aging agent and 120 parts of silver powder;
the epoxy resin-based heat-conducting heat-resistant electric-conductive adhesive film is prepared by the following steps:
s1: uniformly mixing the epoxy resin and the conductive accelerant, and fully grinding;
s2: adding silver powder, mixing uniformly, vacuumizing, adding a diluent, a coupling agent and an anti-aging agent, and mixing uniformly;
s3: adding a curing agent, uniformly mixing, and vacuumizing to obtain the epoxy resin-based heat-conducting heat-resistant electric-conducting adhesive film;
the anti-aging agent is prepared by the following steps:
s11: under ice-bath conditions, 46mL of concentrated H was added to the beaker2SO4Adding 4mL of H when the temperature is reduced to 0 DEG C3PO4And 1g of dried graphite, stirred for 30min, 5g of KMnO was added4Stirring for 10min, stirring at 40 deg.C for 2 hr, stirring at 95 deg.C for 30min, naturally cooling to 60 deg.C, and adding 5% H202Cooling to room temperature, then carrying out suction filtration, centrifugation and freeze drying to obtain graphene oxide;
s12: adding 1.9423g of piperazine hexahydrate, 2.1524g of propyl methacrylate and 10g of graphene oxide into a three-neck flask, stirring at room temperature for 20min, drying by using ethyl acetate as an extracting agent and anhydrous sodium sulfate as a drying agent, and performing rotary evaporation to remove redundant reaction raw materials of propyl methacrylate and ethyl acetate serving as the extracting agent to obtain an intermediate A;
s13: adding 0.2582g of intermediate A, 0.3766g of 1, 2, 2, 6, 6-pentamethyl-4-piperidinol, 10mL of anhydrous toluene and 0.025g of sodium methoxide into a three-neck flask, refluxing and reacting at 150 ℃ for 12h, removing toluene by adopting a reduced pressure distillation method, washing with hot water to remove sodium methoxide, taking ethyl acetate as an extracting agent, collecting an organic phase, concentrating and recrystallizing to obtain the anti-aging agent;
the curing agent is prepared by the following steps:
s51: a four-necked flask equipped with a mechanical stirring paddle, a thermometer and a reflux condenser was charged with 30.2g of cardanol, 12.1g of dibromoneopentane, 100mL of a saturated aqueous NaOH solution and benzyltriethylammonium chloride, and the mixture was stirred in a nitrogen atmosphere2Heating to 150 ℃ in the atmosphere, continuing for 8 hours, filtering off sodium salt generated in the reaction by using silica powder, then carrying out reduced pressure rotary evaporation by using a rotary evaporator, and drying to obtain an intermediate C;
s52: 32.2g of intermediate C and 5.2g of diethylenetriamine are added into a three-neck flask provided with a stirring magneton, a water separator and a thermometer, the mixture is heated to 90 ℃ and reacts for 40min, 8.1g of aqueous formaldehyde solution is dripped into the mixture, the dripping speed is controlled to be 2 drops/s, the mixture is heated to 130 ℃ after the reaction is carried out for 5h, and the curing agent is obtained after the reaction is carried out for 4 h.
Example 4:
the embodiment is an epoxy resin-based heat-conducting heat-resistant electric-conductive adhesive film, which comprises the following components in parts by weight:
15 parts of epoxy resin, 2 parts of diluent, 5 parts of curing agent, 5 parts of coupling agent, 3 parts of conductive accelerator, 5 parts of anti-aging agent and 120 parts of silver powder;
the epoxy resin-based heat-conducting heat-resistant electric-conductive adhesive film is prepared by the following steps:
s1: uniformly mixing the epoxy resin and the conductive accelerant, and fully grinding;
s2: adding silver powder, mixing uniformly, vacuumizing, adding a diluent, a coupling agent and an anti-aging agent, and mixing uniformly;
s3: adding a curing agent, uniformly mixing, and vacuumizing to obtain the epoxy resin-based heat-conducting heat-resistant electric-conducting adhesive film;
the anti-aging agent is prepared by the following steps:
s11: under ice-bath conditions, 46mL of concentrated H was added to the beaker2SO4Adding 4mL of H when the temperature is reduced to 5 DEG C3PO4And 1g of dried graphite, stirring for 60min, and adding 5g of KMnO4Stirring for 20min, stirring at 45 deg.C for 4H, stirring at 105 deg.C for 40min, cooling to 70 deg.C, and adding 5% H202Cooling to room temperature, then carrying out suction filtration, centrifugation and freeze drying to obtain graphene oxide;
s12: adding 1.9423g of piperazine hexahydrate, 2.1524g of propyl methacrylate and 10g of graphene oxide into a three-neck flask, stirring at room temperature for 30min, drying by using ethyl acetate as an extracting agent and anhydrous sodium sulfate as a drying agent, and performing rotary evaporation to remove redundant reaction raw materials of propyl methacrylate and ethyl acetate serving as the extracting agent to obtain an intermediate A;
s13: adding 0.2582g of intermediate A, 0.3766g of 1, 2, 2, 6, 6-pentamethyl-4-piperidinol, 10mL of anhydrous toluene and 0.025g of sodium methoxide into a three-neck flask, refluxing and reacting for 15h at 180 ℃, removing toluene by adopting a reduced pressure distillation method, washing with hot water to remove sodium methoxide, taking ethyl acetate as an extracting agent, collecting an organic phase, concentrating and recrystallizing to obtain the anti-aging agent;
the curing agent is prepared by the following steps:
s51: a four-necked flask equipped with a mechanical stirring paddle, a thermometer and a reflux condenser was charged with 30.2g of cardanol, 12.1g of dibromoneopentane, 100mL of a saturated aqueous NaOH solution and benzyltriethylammonium chloride, and the mixture was stirred in a nitrogen atmosphere2Heating to 150 ℃ in the atmosphere, continuing for 8 hours, filtering off sodium salt generated by the reaction by silica gel powder, then carrying out reduced pressure rotary evaporation by using a rotary evaporator, and drying to obtain an intermediate C;
s52: 32.2g of intermediate C and 5.2g of diethylenetriamine are added into a three-neck flask provided with a stirring magneton, a water separator and a thermometer, the mixture is heated to 90 ℃ and reacts for 40min, 8.1g of aqueous formaldehyde solution is dripped into the mixture, the dripping speed is controlled to be 2 drops/s, the mixture is heated to 130 ℃ after the reaction is carried out for 5h, and the curing agent is obtained after the reaction is carried out for 4 h.
Comparative example 1:
comparative example 1 differs from example 1 in that no curing agent is added.
Comparative example 2:
comparative example 2 a commercially available electro-adhesive film was used.
Performance testing
The electric adhesive films of examples 1-4 and comparative examples 1-2 were tested;
the results are shown in the following table:
as can be seen from the above table, the thermal resistance of the examples reached 1.10 to 1.46, the thermal resistance of comparative example 1 without the addition of the curing agent was 2.89, the thermal resistance of comparative example 2 using a commercially available adhesive film was 1.78, the on-resistance of the examples reached 0.025 to 0.065, the on-resistance of comparative example 1 without the addition of the curing agent was 0.887, the on-resistance of comparative example 2 using a commercially available adhesive film was 0.102, the adhesion resistance at 260 ℃ of the examples reached 0.94 to 0.98, the adhesion resistance at 260 ℃ of comparative example 1 without the addition of the curing agent was 1.56, the adhesion resistance at 260 ℃ of comparative example 2 using a commercially available adhesive film was 1.01, the adhesion resistance at room temperature of the examples reached 0.94 to 0.98, the adhesion resistance at room temperature of comparative example 1 without the addition of the curing agent was 1.56, the adhesion resistance at room temperature of comparative example 2 using a commercially available adhesive film was 1.01, and the data of the examples were superior to each other, the epoxy resin-based heat-conducting heat-resistant electric-conductive adhesive film prepared by the invention has more excellent electrical properties.
In the description herein, references to the description of "one embodiment," "an example," "a specific example," etc., mean that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the invention. In this specification, the schematic representations of the terms used above do not necessarily refer to the same embodiment or example. Furthermore, the particular features, structures, materials, or characteristics described may be combined in any suitable manner in any one or more embodiments or examples.
The foregoing is illustrative and explanatory only and is not intended to be exhaustive or to limit the invention to the precise embodiments described, and various modifications, additions, and substitutions may be made by those skilled in the art without departing from the scope of the invention or exceeding the scope of the claims.
Claims (7)
1. The preparation method of the epoxy resin-based heat-conducting heat-resistant electric-conductive adhesive film is characterized by comprising the following components in parts by weight:
10-15 parts of epoxy resin, 1-2 parts of diluent, 1-5 parts of curing agent, 1-5 parts of coupling agent, 1-3 parts of conductive accelerator, 3-5 parts of anti-aging agent and 120 parts of silver powder;
the epoxy resin-based heat-conducting heat-resistant electric-conductive adhesive film is prepared by the following steps:
s1: uniformly mixing the epoxy resin and the conductive accelerant, and fully grinding;
s2: adding silver powder, mixing uniformly, vacuumizing, adding a diluent, a coupling agent and an anti-aging agent, and mixing uniformly;
s3: adding a curing agent, uniformly mixing, and vacuumizing to obtain the epoxy resin-based heat-conducting heat-resistant electric-conducting adhesive film;
the anti-aging agent is prepared by the following steps:
s11: under ice-bath conditions, concentrated H was added to the beaker2SO4Then adding H3PO4And dried graphite, adding KMnO4Adding H to the system202Cooling to room temperature, then carrying out suction filtration, centrifugation and freeze drying to obtain graphene oxide;
s12: adding piperazine hexahydrate, propyl methacrylate and graphene oxide into a three-neck flask to obtain an intermediate A;
s13: and adding the intermediate A, 1, 2, 2, 6, 6-pentamethyl-4-piperidinol, anhydrous toluene and sodium methoxide into a three-neck flask to obtain the anti-aging agent.
2. According to claim1, the preparation method of the epoxy resin-based heat-conducting heat-resistant electric-conductive adhesive film is characterized in that in the step S11, the concentrated H is2SO4、H3PO4Graphite and KMnO4The dosage ratio of (1) is 46 mL: 4mL of: 1 g: 5g of said compound H202Is 5 percent.
3. The method for preparing an epoxy resin-based heat-conducting heat-resistant electric-conductive adhesive film according to claim 1, wherein the dosage ratio of piperazine hexahydrate, propyl methacrylate and graphene oxide in step S12 is 1.9423 g: 2.1524 g: 10 g.
4. The method for preparing an epoxy resin-based heat-conducting heat-resistant electric-conductive adhesive film according to claim 1, wherein the dosage ratio of the intermediate A, 1, 2, 2, 6, 6-pentamethyl-4-piperidinol and anhydrous toluene in step S13 is 0.2582 g: 0.3766 g: 10mL, wherein the using amount of the sodium methoxide is 2% of the total mass of the intermediate A, the 1, 2, 2, 6, 6-pentamethyl-4-piperidinol and the anhydrous toluene.
5. The method for preparing the epoxy resin-based heat-conducting heat-resistant electric-conductive adhesive film according to claim 1, wherein the curing agent is prepared by the following steps:
s51: adding cardanol, dibromoneopentane, saturated NaOH aqueous solution and benzyltriethylammonium chloride into a four-neck flask provided with a mechanical stirring paddle, a thermometer and a reflux condenser, and drying to obtain an intermediate C;
s52: and adding the intermediate C and diethylenetriamine into a three-neck flask provided with a stirring magneton, a water separator and a thermometer, and dropwise adding a formaldehyde aqueous solution to obtain the curing agent.
6. The preparation method of the epoxy resin-based heat-conducting heat-resistant electric-conductive adhesive film according to claim 5, wherein the using amount ratio of the cardanol, dibromoneopentane to the saturated NaOH aqueous solution in step S51 is 30.2 g: 12.1 g: 100mL, wherein the mass of the benzyltriethylammonium chloride is 0.15% of the total mass of the cardanol, the dibromoneopentane and the saturated NaOH aqueous solution.
7. The method for preparing an epoxy resin-based heat-conducting heat-resistant electric-conductive adhesive film according to claim 5, wherein the amount ratio of the intermediate C, diethylenetriamine and formaldehyde aqueous solution in step S52 is 32.2 g: 5.2 g: 8.1g, wherein the mass fraction of the formaldehyde aqueous solution is 37%.
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| CN101333286A (en) * | 2007-06-26 | 2008-12-31 | 上海经天新材料科技有限公司 | Amine epoxy curing agent modified by cardanol |
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