CN116463096B - Conductive adhesive and preparation method thereof - Google Patents
Conductive adhesive and preparation method thereof Download PDFInfo
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- CN116463096B CN116463096B CN202310496942.2A CN202310496942A CN116463096B CN 116463096 B CN116463096 B CN 116463096B CN 202310496942 A CN202310496942 A CN 202310496942A CN 116463096 B CN116463096 B CN 116463096B
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- 230000001070 adhesive effect Effects 0.000 title claims abstract description 62
- 239000000853 adhesive Substances 0.000 title claims abstract description 59
- 238000002360 preparation method Methods 0.000 title abstract description 16
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 40
- 239000011231 conductive filler Substances 0.000 claims abstract description 24
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims abstract description 19
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 claims abstract description 19
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 claims abstract description 19
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000002904 solvent Substances 0.000 claims abstract description 16
- SJRQTHAMRUOPBJ-UHFFFAOYSA-N 2-Propenyl 2-furancarboxylate Chemical compound C=CCOC(=O)C1=CC=CO1 SJRQTHAMRUOPBJ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000013530 defoamer Substances 0.000 claims abstract description 12
- -1 cyclohexyl allyl propionate Chemical compound 0.000 claims abstract description 11
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 claims abstract description 11
- HHWDZLSGDDXUSM-UHFFFAOYSA-N n-[4-cyano-3-(trifluoromethyl)phenyl]-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NC1=CC=C(C#N)C(C(F)(F)F)=C1 HHWDZLSGDDXUSM-UHFFFAOYSA-N 0.000 claims abstract description 10
- HFCUBKYHMMPGBY-UHFFFAOYSA-N 2-methoxyethyl prop-2-enoate Chemical compound COCCOC(=O)C=C HFCUBKYHMMPGBY-UHFFFAOYSA-N 0.000 claims abstract description 6
- SHBZGQGJTNGCBL-UHFFFAOYSA-N 1-(oxiran-2-ylmethyl)-3-prop-2-enyl-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC=C)C(=O)NC(=O)N1CC1OC1 SHBZGQGJTNGCBL-UHFFFAOYSA-N 0.000 claims abstract description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 26
- 229910021389 graphene Inorganic materials 0.000 claims description 25
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 24
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
- 238000002156 mixing Methods 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- 239000000843 powder Substances 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 12
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 claims description 10
- 244000028419 Styrax benzoin Species 0.000 claims description 5
- 235000000126 Styrax benzoin Nutrition 0.000 claims description 5
- 235000008411 Sumatra benzointree Nutrition 0.000 claims description 5
- 229960002130 benzoin Drugs 0.000 claims description 5
- 235000019382 gum benzoic Nutrition 0.000 claims description 5
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 claims description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 4
- OTKCEEWUXHVZQI-UHFFFAOYSA-N 1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CC=CC=C1 OTKCEEWUXHVZQI-UHFFFAOYSA-N 0.000 claims description 3
- ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 claims description 3
- 230000000694 effects Effects 0.000 abstract description 8
- 230000032683 aging Effects 0.000 abstract description 5
- 239000002518 antifoaming agent Substances 0.000 description 22
- 239000000126 substance Substances 0.000 description 8
- NADYEWVQIJRXJM-UHFFFAOYSA-N 1,3-bis(oxiran-2-ylmethyl)-5-prop-2-enyl-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC=C)C(=O)N1CC1CO1 NADYEWVQIJRXJM-UHFFFAOYSA-N 0.000 description 7
- 239000002356 single layer Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 4
- YYMCVDNIIFNDJK-XFQWXJFMSA-N (z)-1-(3-fluorophenyl)-n-[(z)-(3-fluorophenyl)methylideneamino]methanimine Chemical compound FC1=CC=CC(\C=N/N=C\C=2C=C(F)C=CC=2)=C1 YYMCVDNIIFNDJK-XFQWXJFMSA-N 0.000 description 3
- 244000236521 Bupleurum rotundifolium Species 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- WFCOXVISFBRIKN-UHFFFAOYSA-N 1,3-bis(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)NC(=O)N1CC1CO1 WFCOXVISFBRIKN-UHFFFAOYSA-N 0.000 description 1
- QMNWYGTWTXOQTP-UHFFFAOYSA-N 1h-triazin-6-one Chemical compound O=C1C=CN=NN1 QMNWYGTWTXOQTP-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- GCFAUZGWPDYAJN-UHFFFAOYSA-N cyclohexyl 3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1C=CC(=O)OC1CCCCC1 GCFAUZGWPDYAJN-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 230000003335 steric effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000003878 thermal aging Methods 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 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
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
- C09J163/10—Epoxy resins modified by unsaturated compounds
-
- 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
- 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
- C08K2003/085—Copper
-
- 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
-
- 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
- C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention discloses a conductive adhesive and a preparation method thereof, wherein the conductive adhesive is prepared from the following components in parts by weight: 40 parts of rosin-based epoxy acrylate prepolymer, 3-5 parts of N- (4-cyano-3-trifluoromethylphenyl) methacrylamide, 2-4 parts of aniline tetramer, 3-bis (oxiranylmethyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6 (1H, 3H, 5H) -trione 3-5 parts of 2-methoxyethyl acrylate 8-12 parts, 1-2 parts of vinyl trimethoxysilane, 1-3 parts of octavinyl POSS, 0.5-1 part of allyl furoate, 4-6 parts of cyclohexyl allyl propionate, 30-40 parts of conductive filler, 2-4 parts of photoinitiator, 0.5-0.8 part of defoamer and 5-10 parts of solvent. The conductive adhesive has good conductive effect, good adhesive property, enough heat aging resistance, sufficient performance stability and long service life.
Description
Technical Field
The invention relates to the technical field of adhesives, in particular to a conductive adhesive and a preparation method thereof.
Background
With the continuous development of the electronic and electric industry, the requirement of conductive adhesive for connecting various conductive materials together to form an electric path between the connected materials is increasing, and the performance requirement is also increasing. The conductive adhesive generally uses matrix resin and conductive filler, namely conductive particles, as main components, and combines the conductive particles together through the bonding action of the matrix resin to form a conductive path so as to realize conductive connection of the adhered materials. The ideal conductive adhesive is required to have not only good conductivity but also very high adhesive strength and performance stability.
The traditional conductive adhesive generally uses inorganic materials such as metal powder, graphite powder and the like as conductive fillers, and has the defects of high cost, easy oxidation, easy surface falling and the like. The existing conductive adhesive also has more or less technical problems that color change can occur along with the time extension after use, heat resistance, conductivity, peel strength and reliability are required to be further improved, and the like.
Application number ZL201810883840.5 discloses an epoxy resin adhesive compounded by single-layer graphene macromolecules and a preparation method thereof, and the method adopts solvation to completely avoid the reagglomeration of the single-layer graphene and ensure the single-layer structure. However, the single-layer graphene used in the method is obtained by directly thermally or chemically reducing single-layer graphene oxide, and the preparation method of the single-layer graphene oxide can cause defects to the lamellar structure of the graphene, reduce the regularity and influence the mechanical property of the graphene in an epoxy matrix and the electric conduction and heat conduction enhancement effect, so that the mechanical property and the electric conduction and heat conduction performance of the epoxy resin adhesive compounded by the single-layer graphene macromolecules are poor.
Therefore, there is still a need in the art for a conductive adhesive with good conductive effect, good adhesion, sufficient thermal aging resistance, sufficient performance stability and long service life, and a preparation method thereof.
Disclosure of Invention
The invention mainly aims to provide the conductive adhesive with good conductive effect, good adhesive property, enough heat aging resistance, sufficient performance stability and long service life and the preparation method thereof.
In order to achieve the purpose, the invention provides a conductive adhesive which is prepared from the following components in parts by weight: 40 parts of rosin-based epoxy acrylate prepolymer, 3-5 parts of N- (4-cyano-3-trifluoromethylphenyl) methacrylamide, 2-4 parts of aniline tetramer, 3-bis (oxiranylmethyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6 (1H, 3H, 5H) -trione 3-5 parts of 2-methoxyethyl acrylate 8-12 parts, 1-2 parts of vinyl trimethoxysilane, 1-3 parts of octavinyl POSS, 0.5-1 part of allyl furoate, 4-6 parts of cyclohexyl allyl propionate, 30-40 parts of conductive filler, 2-4 parts of photoinitiator, 0.5-0.8 part of defoamer and 5-10 parts of solvent.
Preferably, the solvent is at least one of N, N-dimethylformamide and N, N-dimethylacetamide.
Preferably, the defoaming agent is AT least one of a defoaming agent AT-99 and a defoaming agent D6800; the manufacturer of the defoaming agent AT-99 is field chemical technology Co., ltd; the manufacturer of the defoaming agent D6800 is a modesty chemical industry Co.
Preferably, the photoinitiator is at least one of benzoin diethyl ether, benzoin isopropyl ether, diphenyl ethanone and 2, 4-dihydroxybenzophenone.
Preferably, the conductive filler is a mixture formed by mixing Super P, conductive carbon black VXC-72, nano ATO conductive powder, graphene and conductive copper powder according to the mass ratio of (1-3): 2 (0.2-0.5): 0.8-1.2): 1-1.5.
Preferably, the Super P is Super P with a Super high model number of MA-EN-CO-01; the conductive carbon black VXC-72 is cabot conductive carbon black VXC-72; the nanometer ATO conductive powder is provided by BoHuasi nanotechnology (Ningbo) limited company and has the product number of Brofos-ATO-50; the graphene is produced by Ningbo ink technology limited company and is of the model Morsh-P2; the conductive copper powder is conductive copper powder with a product number Brofos-Cu-W01 provided by BoHuasi nanotechnology (Ningbo) limited company.
Preferably, the source of the aniline tetramer is not particularly limited, and in one embodiment of the present invention, the aniline tetramer is prepared according to the method of example 1 in chinese patent No. 103866423B.
Preferably, the source of the rosin-based epoxy acrylate prepolymer is not particularly limited, and in one embodiment of the present invention, the rosin-based epoxy acrylate prepolymer is prepared according to the method of example 1 in chinese patent No. CN 103254405B.
The invention provides a preparation method of the conductive adhesive, which comprises the following steps: and uniformly mixing the components according to the parts by weight to obtain a finished conductive adhesive product.
Due to the application of the technical scheme, the invention has the following beneficial effects:
(1) The preparation method of the conductive adhesive disclosed by the invention has the advantages of simple process, convenience in operation and use, small equipment dependence, high preparation efficiency and high finished product qualification rate, and is suitable for continuous large-scale production.
(2) The invention discloses a conductive adhesive which is prepared from the following components in parts by weight: 40 parts of rosin-based epoxy acrylate prepolymer, 3-5 parts of N- (4-cyano-3-trifluoromethylphenyl) methacrylamide, 2-4 parts of aniline tetramer, 3-bis (oxiranylmethyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6 (1H, 3H, 5H) -trione 3-5 parts of 2-methoxyethyl acrylate 8-12 parts, 1-2 parts of vinyl trimethoxysilane, 1-3 parts of octavinyl POSS, 0.5-1 part of allyl furoate, 4-6 parts of cyclohexyl allyl propionate, 30-40 parts of conductive filler, 2-4 parts of photoinitiator, 0.5-0.8 part of defoamer and 5-10 parts of solvent; through reasonable selection of components and proportions thereof, the prepared conductive adhesive has good conductive effect, good bonding performance, enough heat aging resistance, sufficient performance stability and long service life.
(3) The conductive filler is a mixture formed by mixing Super P, conductive carbon black VXC-72, nano ATO conductive powder, graphene and conductive copper powder according to the mass ratio of (1-3) 2 (0.2-0.5) (0.8-1.2) (1-1.5), and the mixture is interacted with aniline tetramer, so that the prepared adhesive has good conductive performance; the components vinyl trimethoxy silane and rosin-based epoxy acrylate prepolymer can enable the conductive fillers to be uniformly dispersed to form an effective conductive network; and the conductive fillers can be better contacted through the combination of particle size and types, so that the probability of forming an effective electronic channel is increased, the contact resistance is improved, and the conductivity is improved.
(4) The conductive adhesive disclosed by the invention has the advantages that the components containing unsaturated olefinic bonds, such as rosin-based epoxy acrylate prepolymer, N- (4-cyano-3-trifluoromethyl phenyl) methacrylamide, 1, 3-bis (oxiranylmethyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6 (1H, 3H, 5H) -trione, 2-methoxyethyl acrylate, vinyl trimethoxysilane, octavinyl POSS, allyl furoate and cyclohexyl allyl propionate, are cured under the action of a photoinitiator, and simultaneously, amino groups on the aniline tetramer can also have epoxy ring-opening reaction with epoxy groups on 1, 3-bis (oxiranylmethyl) -1,3, 5-triazine-2, 4,6 (1H, 3H, 5H) -trione to form a multiple interpenetrating network structure, so that the conductive filler can be better contacted, and the aging resistance, the conductivity and the heat resistance of the adhesive can be effectively improved. By the components, structures such as rosin group, cyano group, trifluoromethyl phenyl group, amide group, cyclohexyl ester, trimethoxy silane, triazinone and the like are simultaneously introduced into the molecular structure of the adhesive, and the manufactured adhesive product has better ageing resistance, heat resistance and performance stability and longer service life under the multiple actions of electronic effect, steric effect and conjugation effect.
Detailed Description
The following description is presented to enable one of ordinary skill in the art to make and use the invention. The preferred embodiments in the following description are by way of example only and other obvious variations will occur to those skilled in the art.
Example 1
The conductive adhesive is prepared from the following components in parts by weight: 40 parts of rosin-based epoxy acrylate prepolymer, 3 parts of N- (4-cyano-3-trifluoromethylphenyl) methacrylamide, 2 parts of aniline tetramer, 3 parts of 1, 3-bis (oxiranylmethyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6 (1H, 3H, 5H) -trione, 3 parts of 2-methoxyethyl 2-acrylate, 8 parts of vinyl trimethoxysilane, 1 part of octavinyl POSS, 0.5 part of allyl furoate, 4 parts of cyclohexyl allyl propionate, 30 parts of conductive filler, 2 parts of photoinitiator, 0.5 part of defoamer and 5 parts of solvent.
The solvent is N, N-dimethylformamide; the defoaming agent is a defoaming agent AT-99, and a manufacturer of the defoaming agent AT-99 is a field chemical technology Co., ltd; the photoinitiator is benzoin diethyl ether; the conductive filler is a mixture formed by mixing Super P, conductive carbon black VXC-72, nano ATO conductive powder, graphene and conductive copper powder according to a mass ratio of 1:2:0.2:0.8:1.
The Super P is Super P with the Super high model of MA-EN-CO-01; the conductive carbon black VXC-72 is cabot conductive carbon black VXC-72; the nanometer ATO conductive powder is provided by BoHuasi nanotechnology (Ningbo) limited company and has the product number of Brofos-ATO-50; the graphene is produced by Ningbo ink technology limited company and is of the model Morsh-P2; the conductive copper powder is conductive copper powder with a product number of Brofos-Cu-W01 provided by BoHuasi nanotechnology (Ningbo) limited company; the aniline tetramer is prepared according to the method of example 1 in Chinese patent No. 103866423B; the rosin-based epoxy acrylate prepolymer was prepared according to the method of example 1 in chinese patent No. CN 103254405B.
The preparation method of the conductive adhesive comprises the following steps: and uniformly mixing the components according to the parts by weight to obtain a finished conductive adhesive product.
Example 2
The conductive adhesive is prepared from the following components in parts by weight: 40 parts of rosin-based epoxy acrylate prepolymer, 3.5 parts of N- (4-cyano-3-trifluoromethylphenyl) methacrylamide, 2.5 parts of aniline tetramer, 3-bis (oxiranylmethyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6 (1H, 3H, 5H) -trione 3.5 parts of 2-methoxyethyl acrylate 9 parts, vinyl trimethoxysilane 1.2 parts, octavinyl POSS 1.5 parts, allyl furoate 0.7 parts, cyclohexyl allyl propionate 4.5 parts, 33 parts of conductive filler, 2.5 parts of photoinitiator, 0.6 parts of defoamer and 6 parts of solvent.
The solvent is N, N-dimethylacetamide; the defoaming agent is a defoaming agent D6800; the manufacturer of the defoaming agent D6800 is a modesty chemical industry Co., ltd; the photoinitiator is benzoin isopropyl ether; the conductive filler is a mixture formed by mixing Super P, conductive carbon black VXC-72, nano ATO conductive powder, graphene and conductive copper powder according to a mass ratio of 1.5:2:0.3:0.9:1.1.
The Super P is Super P with the Super high model of MA-EN-CO-01; the conductive carbon black VXC-72 is cabot conductive carbon black VXC-72; the nanometer ATO conductive powder is provided by BoHuasi nanotechnology (Ningbo) limited company and has the product number of Brofos-ATO-50; the graphene is produced by Ningbo ink technology limited company and is of the model Morsh-P2; the conductive copper powder is conductive copper powder with a product number of Brofos-Cu-W01 provided by BoHuasi nanotechnology (Ningbo) limited company; the aniline tetramer is prepared according to the method of example 1 in Chinese patent No. 103866423B; the rosin-based epoxy acrylate prepolymer was prepared according to the method of example 1 in chinese patent No. CN 103254405B.
The preparation method of the conductive adhesive comprises the following steps: and uniformly mixing the components according to the parts by weight to obtain a finished conductive adhesive product.
Example 3
The conductive adhesive is prepared from the following components in parts by weight: 40 parts of rosin-based epoxy acrylate prepolymer, 4 parts of N- (4-cyano-3-trifluoromethylphenyl) methacrylamide, 3 parts of aniline tetramer, 4 parts of 1, 3-bis (oxiranylmethyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6 (1H, 3H, 5H) -trione, 10 parts of 2-methoxyethyl 2-acrylate, 1.5 parts of vinyl trimethoxysilane, 2 parts of octavinyl POSS, 0.75 part of allyl furoate, 5 parts of cyclohexyl allyl propionate, 35 parts of conductive filler, 3 parts of photoinitiator, 0.65 part of defoamer and 7 parts of solvent.
The solvent is N, N-dimethylformamide; the defoaming agent is a defoaming agent AT-99, and a manufacturer of the defoaming agent AT-99 is a field chemical technology Co., ltd; the photoinitiator is diphenyl ethanone; the conductive filler is a mixture formed by mixing Super P, conductive carbon black VXC-72, nano ATO conductive powder, graphene and conductive copper powder according to a mass ratio of 2:2:0.35:1:1.3.
The Super P is Super P with the Super high model of MA-EN-CO-01; the conductive carbon black VXC-72 is cabot conductive carbon black VXC-72; the nanometer ATO conductive powder is provided by BoHuasi nanotechnology (Ningbo) limited company and has the product number of Brofos-ATO-50; the graphene is produced by Ningbo ink technology limited company and is of the model Morsh-P2; the conductive copper powder is conductive copper powder with a product number of Brofos-Cu-W01 provided by BoHuasi nanotechnology (Ningbo) limited company; the aniline tetramer is prepared according to the method of example 1 in Chinese patent No. 103866423B; the rosin-based epoxy acrylate prepolymer was prepared according to the method of example 1 in chinese patent No. CN 103254405B.
The preparation method of the conductive adhesive comprises the following steps: and uniformly mixing the components according to the parts by weight to obtain a finished conductive adhesive product.
Example 4
The conductive adhesive is prepared from the following components in parts by weight: 40 parts of rosin-based epoxy acrylate prepolymer, 4.5 parts of N- (4-cyano-3-trifluoromethylphenyl) methacrylamide, 3.5 parts of aniline tetramer, 4.5 parts of 1, 3-bis (oxiranylmethyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6 (1H, 3H, 5H) -trione, 11 parts of 2-methoxyethyl 2-acrylate, 1.8 parts of vinyl trimethoxysilane, 2.5 parts of octavinyl POSS, 0.9 part of allyl furoate, 5.5 parts of cyclohexyl allyl propionate, 38 parts of conductive filler, 3.5 parts of photoinitiator, 0.75 parts of defoamer and 9 parts of solvent.
The solvent is a mixture formed by mixing N, N-dimethylformamide and N, N-dimethylacetamide according to a mass ratio of 1:2; the defoaming agent is a mixture formed by mixing a defoaming agent AT-99 and a defoaming agent D6800 according to a mass ratio of 3:5; the manufacturer of the defoaming agent AT-99 is field chemical technology Co., ltd; the manufacturer of the defoaming agent D6800 is a modesty chemical industry Co., ltd; the photoinitiator is a mixture formed by mixing benzoin diethyl ether, benzoin isopropyl ether, diphenyl ketone and 2, 4-dihydroxybenzophenone according to a mass ratio of 1:1:3:1.
The conductive filler is a mixture formed by mixing Super P, conductive carbon black VXC-72, nano ATO conductive powder, graphene and conductive copper powder according to a mass ratio of 2.5:2:0.45:1.1:1.4; the Super P is Super P with the Super high model of MA-EN-CO-01; the conductive carbon black VXC-72 is cabot conductive carbon black VXC-72; the nanometer ATO conductive powder is provided by BoHuasi nanotechnology (Ningbo) limited company and has the product number of Brofos-ATO-50; the graphene is produced by Ningbo ink technology limited company and is of the model Morsh-P2; the conductive copper powder is conductive copper powder with a product number of Brofos-Cu-W01 provided by BoHuasi nanotechnology (Ningbo) limited company; the aniline tetramer is prepared according to the method of example 1 in Chinese patent No. 103866423B; the rosin-based epoxy acrylate prepolymer was prepared according to the method of example 1 in chinese patent No. CN 103254405B.
The preparation method of the conductive adhesive comprises the following steps: and uniformly mixing the components according to the parts by weight to obtain a finished conductive adhesive product.
Example 5
The conductive adhesive is prepared from the following components in parts by weight: 40 parts of rosin-based epoxy acrylate prepolymer, 5 parts of N- (4-cyano-3-trifluoromethylphenyl) methacrylamide, 4 parts of aniline tetramer, 5 parts of 1, 3-bis (oxiranylmethyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6 (1H, 3H, 5H) -trione, 12 parts of 2-methoxyethyl 2-acrylate, 2 parts of vinyl trimethoxysilane, 3 parts of octavinyl POSS, 1 part of allyl furoate, 6 parts of allyl cyclohexyl propionate, 40 parts of conductive filler, 4 parts of photoinitiator, 0.8 part of defoamer and 10 parts of solvent.
The solvent is N, N-dimethylformamide; the defoaming agent is a defoaming agent AT-99, and a manufacturer of the defoaming agent AT-99 is a field chemical technology Co., ltd; the photoinitiator is benzoin diethyl ether; the conductive filler is a mixture formed by mixing Super P, conductive carbon black VXC-72, nano ATO conductive powder, graphene and conductive copper powder according to a mass ratio of 3:2:0.5:1.2:1.5; the Super P is Super P with the Super high model of MA-EN-CO-01; the conductive carbon black VXC-72 is cabot conductive carbon black VXC-72; the nanometer ATO conductive powder is provided by BoHuasi nanotechnology (Ningbo) limited company and has the product number of Brofos-ATO-50; the graphene is produced by Ningbo ink technology limited company and is of the model Morsh-P2; the conductive copper powder is conductive copper powder with a product number of Brofos-Cu-W01 provided by BoHuasi nanotechnology (Ningbo) limited company; the aniline tetramer is prepared according to the method of example 1 in Chinese patent No. 103866423B; the rosin-based epoxy acrylate prepolymer was prepared according to the method of example 1 in chinese patent No. CN 103254405B.
The preparation method of the conductive adhesive comprises the following steps: and uniformly mixing the components according to the parts by weight to obtain a finished conductive adhesive product.
Comparative example 1
A conductive adhesive was substantially the same as in example 1 except that aniline tetramer and allyl cyclohexylpropionate were not added, and Super P was used in place of conductive carbon black VXC-72 in the conductive filler.
Comparative example 2
A conductive adhesive was substantially the same as in example 1 except that 1, 3-bis (oxiranylmethyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6 (1 h,3h,5 h) -trione and allyl furoate were not added, and that graphene was replaced with conductive copper powder in the conductive filler.
In order to further illustrate the beneficial technical effects of the conductive adhesives prepared in the examples of the present invention, the conductive adhesives prepared in examples 1-5 and comparative examples 1-2 were subjected to the relevant performance test, the test results are shown in table 1, and the test methods are as follows:
(1) Volume resistivity: for the volume resistivity of the cured conductive adhesive in each example, the volume resistivity of the solid material specified in GB/T1410-2006 was measured by using an ultraviolet lamp with intensity of 1000mw/cm for XC210 (wavelength of 365 nm) of IGE 2 The time was 15 seconds.
(2) Tensile shear strength: each adhesive was coated onto a sheet of ABS material to form a uniform film of 0.3mm thickness, and after curing, the tensile shear strength at room temperature of 20℃was determined using GB/T7124-1986. Curing with an IGE XC210 (365 nm wavelength) UV lamp with a light intensity of 1000mw/cm 2 The time was 15 seconds.
(3) Wet heat resistance: and (3) placing each cured adhesive sample at 85 ℃ under the environment condition with the relative humidity of 93% for 90 hours, cooling to the room temperature, detecting the tensile shear strength again according to the method in (2), and calculating the retention rate of the tensile shear strength, wherein the larger the value is, the better the wet heat resistance is.
TABLE 1
| Project | Volume resistivity | Tensile shear Strength | Moisture and heat resistance |
| Unit (B) | 10 -4 Ω.cm | MPa | % |
| Example 1 | 1.3 | 4.0 | 98.3 |
| Example 2 | 1.0 | 4.2 | 98.8 |
| Example 3 | 0.8 | 4.5 | 99.0 |
| Example 4 | 0.6 | 4.6 | 99.3 |
| Example 5 | 0.5 | 4.8 | 99.5 |
| Comparative example 1 | 2.2 | 3.4 | 96.7 |
| Comparative example 2 | 2.8 | 3.0 | 95.2 |
As can be seen from Table 1, the conductive adhesive disclosed in the examples of the present invention has more excellent adhesive property, conductive property and wet heat resistance than the comparative example product, and the addition of aniline tetramer, allyl cyclohexylpropionate, conductive carbon black VXC-72, 1, 3-bis (oxiranylmethyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6 (1H, 3H, 5H) -trione, allyl furoate, graphene is beneficial to improving the above properties.
The foregoing has shown and described the basic principles, principal features and advantages of the invention. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, and that the above embodiments and descriptions are merely illustrative of the principles of the present invention, and various changes and modifications may be made therein without departing from the spirit and scope of the invention, which is defined by the appended claims. The scope of the invention is defined by the appended claims and equivalents thereof.
Claims (7)
1. The conductive adhesive is characterized by being prepared from the following components in parts by weight: 40 parts of rosin-based epoxy acrylate prepolymer, 3-5 parts of N- (4-cyano-3-trifluoromethylphenyl) methacrylamide, 2-4 parts of aniline tetramer, 3-bis (oxiranylmethyl) -5- (2-propenyl) -1,3, 5-triazine-2, 4,6 (1H, 3H, 5H) -trione 3-5 parts of 2-methoxyethyl acrylate 8-12 parts, 1-2 parts of vinyl trimethoxysilane, 1-3 parts of octavinyl POSS, 0.5-1 part of allyl furoate, 4-6 parts of cyclohexyl allyl propionate, 30-40 parts of conductive filler, 2-4 parts of photoinitiator, 0.5-0.8 part of defoamer and 5-10 parts of solvent; the conductive filler is a mixture formed by mixing Super P, conductive carbon black VXC-72, nano ATO conductive powder, graphene and conductive copper powder according to the mass ratio of (1-3) 2 (0.2-0.5) 0.8-1.2 (1-1.5).
2. The conductive adhesive of claim 1, wherein the solvent is at least one of N, N-dimethylformamide, N-dimethylacetamide.
3. The conductive adhesive of claim 1, wherein the defoamer is AT least one of defoamer AT-99, defoamer D6800.
4. The conductive adhesive of claim 1, wherein the photoinitiator is at least one of benzoin diethyl ether, benzoin isopropyl ether, diphenyl ethanone, 2, 4-dihydroxybenzophenone.
5. The conductive adhesive of claim 1, wherein the conductive carbon black VXC-72 is cabot conductive carbon black VXC-72.
6. The conductive adhesive of claim 1, wherein the graphene is of the type Morsh-P2.
7. A method for preparing the conductive adhesive according to any one of claims 1 to 6, comprising the steps of: and uniformly mixing the components according to the parts by weight to obtain a finished conductive adhesive product.
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