CN112795344A - Dual-curing single-component epoxy resin adhesive and preparation method thereof - Google Patents
Dual-curing single-component epoxy resin adhesive and preparation method thereof Download PDFInfo
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- CN112795344A CN112795344A CN202110068057.5A CN202110068057A CN112795344A CN 112795344 A CN112795344 A CN 112795344A CN 202110068057 A CN202110068057 A CN 202110068057A CN 112795344 A CN112795344 A CN 112795344A
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- epoxy resin
- parts
- dual
- curing
- resin adhesive
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- 239000003822 epoxy resin Substances 0.000 title claims abstract description 120
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 120
- 239000000853 adhesive Substances 0.000 title claims abstract description 67
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 67
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 239000003999 initiator Substances 0.000 claims abstract description 17
- 239000002518 antifoaming agent Substances 0.000 claims abstract description 13
- 239000000945 filler Substances 0.000 claims abstract description 13
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000003381 stabilizer Substances 0.000 claims abstract description 13
- 239000012745 toughening agent Substances 0.000 claims abstract description 13
- 239000002994 raw material Substances 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 18
- -1 oxybis-methylene Chemical group 0.000 claims description 14
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 12
- 238000002156 mixing Methods 0.000 claims description 12
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 12
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 11
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- 229920000459 Nitrile rubber Polymers 0.000 claims description 7
- 229920002635 polyurethane Polymers 0.000 claims description 7
- 239000004814 polyurethane Substances 0.000 claims description 7
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 claims description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 5
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 5
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 5
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 claims description 5
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims description 4
- UWFHYGTWXNRUDH-UHFFFAOYSA-N 3-ethyl-3-[4-[(3-ethyloxetan-3-yl)methoxy]butoxymethyl]oxetane Chemical compound C1OCC1(CC)COCCCCOCC1(CC)COC1 UWFHYGTWXNRUDH-UHFFFAOYSA-N 0.000 claims description 4
- LMIOYAVXLAOXJI-UHFFFAOYSA-N 3-ethyl-3-[[4-[(3-ethyloxetan-3-yl)methoxymethyl]phenyl]methoxymethyl]oxetane Chemical compound C=1C=C(COCC2(CC)COC2)C=CC=1COCC1(CC)COC1 LMIOYAVXLAOXJI-UHFFFAOYSA-N 0.000 claims description 4
- CGRJJOYCFCCGPX-UHFFFAOYSA-N 3-ethyloxetane Chemical compound CCC1COC1 CGRJJOYCFCCGPX-UHFFFAOYSA-N 0.000 claims description 4
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 4
- 235000010354 butylated hydroxytoluene Nutrition 0.000 claims description 4
- 239000004359 castor oil Substances 0.000 claims description 4
- 235000019438 castor oil Nutrition 0.000 claims description 4
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 4
- RVWUHFFPEOKYLB-UHFFFAOYSA-N 2,2,6,6-tetramethyl-1-oxidopiperidin-1-ium Chemical compound CC1(C)CCCC(C)(C)[NH+]1[O-] RVWUHFFPEOKYLB-UHFFFAOYSA-N 0.000 claims description 3
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 claims description 3
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 claims description 3
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 claims description 3
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical class [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 claims description 3
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 3
- 235000021355 Stearic acid Nutrition 0.000 claims description 3
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 3
- 150000004056 anthraquinones Chemical class 0.000 claims description 3
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 claims description 3
- 229920001971 elastomer Polymers 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 3
- SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical compound [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- 229920006122 polyamide resin Polymers 0.000 claims description 3
- 229920000570 polyether Polymers 0.000 claims description 3
- 229920002379 silicone rubber Polymers 0.000 claims description 3
- 239000003549 soybean oil Substances 0.000 claims description 3
- 235000012424 soybean oil Nutrition 0.000 claims description 3
- 239000008117 stearic acid Substances 0.000 claims description 3
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical class [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 238000005303 weighing Methods 0.000 claims description 3
- 239000004944 Liquid Silicone Rubber Substances 0.000 claims description 2
- 230000009977 dual effect Effects 0.000 claims 1
- 238000003860 storage Methods 0.000 abstract description 12
- 238000001723 curing Methods 0.000 description 51
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 239000003292 glue Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 238000013007 heat curing Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- 238000006757 chemical reactions by type Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000016 photochemical curing Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000009864 tensile test Methods 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 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
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- 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
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4014—Nitrogen containing compounds
- C08G59/4021—Ureas; Thioureas; Guanidines; Dicyandiamides
-
- 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
- C08G59/50—Amines
- C08G59/5046—Amines heterocyclic
- C08G59/5053—Amines heterocyclic containing only nitrogen as a heteroatom
- C08G59/5073—Amines heterocyclic containing only nitrogen as a heteroatom having two nitrogen atoms in the ring
-
- 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
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
- C09J163/04—Epoxynovolacs
-
- 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
- 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
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/24—Acids; Salts thereof
- C08K3/26—Carbonates; Bicarbonates
- C08K2003/265—Calcium, strontium or barium carbonate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
- C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
Abstract
The invention discloses a dual-curing single-component epoxy resin adhesive and a preparation method thereof, wherein the dual-curing single-component epoxy resin adhesive is prepared from the following raw materials in parts by weight: 20-40 parts of flexible epoxy resin, 30-50 parts of photosensitive epoxy resin, 5-14 parts of oxetane, 10-20 parts of toughening agent, 0.5-5 parts of stabilizer, 1-8 parts of photoinitiator, 5-20 parts of thermal initiator, 0.2-2 parts of defoaming agent and 2-15 parts of filler. The invention has excellent mechanical property and thixotropy, can be quickly positioned under the irradiation of ultraviolet light, has excellent storage stability, can be stored for a long time at minus 5 ℃ and can also be stored for 3 months at normal temperature.
Description
Technical Field
The invention relates to the field of adhesives, in particular to a dual-curing single-component epoxy resin adhesive and a preparation method thereof.
Background
The epoxy resin adhesive is a potting material prepared by taking epoxy resin as a matrix, adding various functional auxiliaries and matching with a proper curing agent system. Because the epoxy resin adhesive has excellent performance and good aging resistance, the epoxy resin adhesive is widely applied to various industrial assembly working conditions. With the development of economy and the advancement of science and technology, various new assembly techniques are continuously appeared, which have more and more demands on adhesives for bonding and also present more challenges to the product performance of the adhesives. The traditional epoxy resin adhesive mainly comprises a two-component reaction type product, the mechanical property of the product is excellent after the product is cured, but the two components need to be mixed, the relative operation is inconvenient, the two components are not uniformly mixed, the adhesive line cannot be too thin, and the like; the traditional single-component epoxy resin adhesive can avoid mixing of two components, but needs heating in curing, is slow in curing speed, generally needs to be stored at a low temperature of not more than-15 ℃, and is difficult to apply in some working conditions requiring quick positioning.
Disclosure of Invention
Aiming at the defects in the prior art, the invention provides the dual-curing single-component epoxy resin adhesive and the preparation method thereof, which not only have excellent mechanical property and thixotropy, can be quickly positioned under the irradiation of ultraviolet light, but also have excellent storage stability, can be stored for a long time at the temperature of-5 ℃, and can also be stored for 3 months at normal temperature.
The purpose of the invention is realized by the following technical scheme:
a dual-curing single-component epoxy resin adhesive is prepared from the following raw materials in parts by weight: 20-40 parts of flexible epoxy resin, 30-50 parts of photosensitive epoxy resin, 5-14 parts of oxetane, 10-20 parts of toughening agent, 0.5-5 parts of stabilizer, 1-8 parts of photoinitiator, 5-20 parts of thermal initiator, 0.2-2 parts of defoaming agent and 2-15 parts of filler.
Preferably, the flexible epoxy resin is at least one of soybean oil modified epoxy resin, furfuryl alcohol modified epoxy resin, castor oil modified epoxy resin, polyurethane modified epoxy resin, furan modified epoxy resin and vinyl modified epoxy resin.
Preferably, the photosensitive epoxy resin is at least one of acrylic modified epoxy resin and phenolic modified epoxy resin.
Preferably, the oxetane is at least one of 3,3' - (oxybismethylene) bis (3-ethyl) oxetane, 3-ethyl-3- [4- [ (3-ethyloxetan-3-yl) methoxy ] butoxymethyl ] oxetane, and 1, 4-bis [ (3-ethyl-3-oxetanylmethoxy) methyl ] benzene.
Preferably, the toughening agent is at least one of liquid carboxyl-terminated nitrile rubber, liquid amino-terminated nitrile rubber, polyamide resin, propylene oxide rubber, liquid polyurethane, liquid silicone rubber, nano titanium dioxide, polyether and active nano calcium carbonate.
Preferably, the stabilizer is at least one of hydroquinone, p-benzoquinone, 2, 6-di-tert-butyl-p-cresol, benzoquinone, 1, 4-naphthoquinone, EDTA-4Na salt, EDTA-2Na salt, 4-methoxyphenol, anthraquinone, stearic acid, p-hydroxyanisole and 2,2,6, 6-tetramethylpiperidine oxide.
Preferably, the photoinitiator is a diaryl iodate or a triaryl iodate.
Preferably, the thermal initiator adopts at least one of diamino diphenyl sulfone, diamino diphenyl methane, dicyandiamide, 2-methylimidazole, 2-ethyl-4-methylimidazole and 2-phenylimidazole.
A preparation method of a dual-curing single-component epoxy resin adhesive comprises the following steps:
step 1, weighing flexible epoxy resin, photosensitive epoxy resin, oxetane, a toughening agent, a stabilizer, a photoinitiator, a thermal initiator, a defoaming agent and a filler according to the formula of the dual-curing single-component epoxy resin adhesive;
step 2, adding the flexible epoxy resin, the photosensitive epoxy resin, the oxetane, the defoaming agent and the stabilizer into a reaction kettle, and uniformly dispersing and mixing;
step 3, adding the toughening agent, the filler and the thermal initiator into the reaction kettle, and uniformly dispersing and mixing;
and 4, adding the photoinitiator into the reaction kettle, uniformly dispersing and mixing, and then defoaming in vacuum for 30min to obtain the dual-curing single-component epoxy resin adhesive.
Preferably, the types and contents of the photoinitiator and the thermal initiator are adjusted, so that dual-curing single-component epoxy resin adhesives with different curing speeds are prepared.
According to the technical scheme provided by the invention, the preparation process is simple and convenient, and the dual-curing single-component epoxy resin adhesive with different curing speeds can be prepared by adjusting the types and contents of the photoinitiator and the thermal initiator; the dual-curing single-component epoxy resin adhesive has excellent mechanical property and thixotropy, can be quickly positioned under the irradiation of ultraviolet light, has excellent storage stability, can be stored for a long time at the temperature of minus 5 ℃, and can also be stored for 3 months at normal temperature.
Detailed Description
The technical solutions in the present invention are clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments of the present invention without making any creative effort, shall fall within the protection scope of the present invention.
The dual-curing one-component epoxy resin adhesive and the preparation method thereof provided by the invention are described in detail below. Details which are not described in detail in the embodiments of the invention belong to the prior art which is known to the person skilled in the art.
A dual-curing single-component epoxy resin adhesive is prepared from the following raw materials in parts by weight: 20-40 parts of flexible epoxy resin, 30-50 parts of photosensitive epoxy resin, 5-14 parts of oxetane, 10-20 parts of toughening agent, 0.5-5 parts of stabilizer, 1-8 parts of photoinitiator, 5-20 parts of thermal initiator, 0.2-2 parts of defoaming agent and 2-15 parts of filler.
Wherein, the raw materials of the dual-curing single-component epoxy resin adhesive can comprise the following embodiments:
(1) the flexible epoxy resin is at least one of soybean oil modified epoxy resin, furfuryl alcohol modified epoxy resin, castor oil modified epoxy resin, polyurethane modified epoxy resin, furan modified epoxy resin and vinyl modified epoxy resin.
(2) The photosensitive epoxy resin is at least one of acrylic modified epoxy resin and phenolic modified epoxy resin.
(3) The oxetane is at least one of 3,3' - (oxybis methylene) bis (3-ethyl) oxetane, 3-ethyl-3- [4- [ (3-ethyloxetan-3-yl) methoxy ] butoxymethyl ] oxetane and 1, 4-bis [ (3-ethyl-3-oxetanylmethoxy) methyl ] benzene.
(4) The toughening agent adopts at least one of liquid carboxyl-terminated nitrile rubber, liquid amino-terminated nitrile rubber, polyamide resin, epoxypropane rubber, liquid polyurethane, liquid silicon rubber, nano titanium dioxide, polyether and active nano calcium carbonate.
(5) The stabilizer is at least one of hydroquinone, p-benzoquinone, 2, 6-di-tert-butyl-p-cresol, benzoquinone, 1, 4-naphthoquinone, EDTA-4Na salt, EDTA-2Na salt, 4-methoxyphenol, anthraquinone, stearic acid, p-hydroxyanisole and 2,2,6, 6-tetramethylpiperidine oxide.
(6) The photoinitiator adopts diaryl iodate or triaryl iodate.
(7) The thermal initiator is at least one of diamino diphenyl sulfone, diamino diphenyl methane, dicyandiamide, 2-methylimidazole, 2-ethyl-4-methylimidazole and 2-phenylimidazole.
Specifically, the preparation method of the dual-curing single-component epoxy resin adhesive can comprise the following steps:
step 1, weighing flexible epoxy resin, photosensitive epoxy resin, oxetane, a toughening agent, a stabilizer, a photoinitiator, a thermal initiator, a defoaming agent and a filler according to the formula of the dual-curing single-component epoxy resin adhesive.
And 2, adding the flexible epoxy resin, the photosensitive epoxy resin, the oxetane, the defoaming agent and the stabilizer into a reaction kettle, and uniformly dispersing and mixing at the rotating speed of 300 rpm.
And 3, adding the toughening agent, the filler and the thermal initiator into the reaction kettle, and uniformly dispersing and mixing at the rotating speed of 800 rpm.
And 4, adding the photoinitiator into the reaction kettle, uniformly dispersing and mixing at the rotating speed of 800rpm, and then defoaming in vacuum for 30min to obtain the dual-curing single-component epoxy resin adhesive.
Compared with the prior art, the dual-curing single-component epoxy resin adhesive provided by the invention at least has the following advantages:
(1) the dual-curing single-component epoxy resin adhesive provided by the invention can be cured by heat and ultraviolet irradiation, and can be quickly positioned under the irradiation of ultraviolet light, so that the working cycle is accelerated.
(2) The dual-curing single-component epoxy resin adhesive provided by the invention can be directly used without mixing the component A and the component B like a two-component reaction type product, so that the dual-curing single-component epoxy resin adhesive is simple and convenient to operate when in use, and the problems of uneven mixing of the two components and the like are avoided.
(3) The dual-curing single-component epoxy resin adhesive provided by the invention has excellent storage stability, can be stored for a long time at-5 ℃ and can also be stored for 3 months at normal temperature.
(4) The dual-curing single-component epoxy resin adhesive provided by the invention has excellent mechanical properties after curing, and has higher strength and toughness.
(5) The preparation method of the dual-curing single-component epoxy resin adhesive provided by the invention is convenient in operation process, has good thixotropy, and can be used for gluing inclined planes, vertical planes and top surfaces.
In conclusion, the embodiment of the invention has excellent mechanical property and thixotropy, can be quickly positioned under the irradiation of ultraviolet light, has excellent storage stability, can be stored for a long time at-5 ℃ and can also be stored for 3 months at normal temperature.
In order to more clearly show the technical scheme and the technical effects provided by the present invention, the dual-curing one-component epoxy resin adhesive and the preparation method thereof provided by the embodiment of the present invention are described in detail in the following with specific embodiments.
Example 1
The preparation method of the dual-curing one-component epoxy resin adhesive comprises the following steps (by weight):
step A1, adding 30 parts of furfuryl alcohol modified epoxy resin, 30 parts of acrylic acid modified epoxy resin, 9 parts of 3-ethyl-3- [4- [ (3-ethyloxetan-3-yl) methoxy ] butoxymethyl ] oxetane, 9 parts of defoaming agent BYK A5301 parts, 0.8 part of 2, 6-di-tert-butyl-p-cresol and 0.4 part of p-benzoquinone into a reaction kettle, and dispersing for 30min at the rotating speed of 300rpm until the mixture is uniformly mixed.
Step A2, adding 15.5 parts of liquid carboxyl nitrile rubber, 7 parts of filler ball star silicon micro powder and 16.3 parts of dicyandiamide into the reaction kettle, and dispersing for 2 hours at the rotating speed of 800rpm until the mixture is uniformly mixed.
And A3, adding 3.4 parts of diaryl iodate into the reaction kettle, dispersing for 30min at the rotating speed of 800rpm until the diaryl iodate and the diaryl iodate are uniformly mixed, and then defoaming for 30min in vacuum to obtain the dual-curing single-component epoxy resin adhesive.
Example 2
The preparation method of the dual-curing one-component epoxy resin adhesive comprises the following steps (by weight):
and step B1, adding 31.2 parts of castor oil modified epoxy resin, 44 parts of acrylic acid modified epoxy resin, 8.2 parts of 1, 4-bis [ (3-ethyl-3-oxetanylmethoxy) methyl ] benzene, 8.5 parts of defoaming agent BYK A5500.9 parts and 1.5 parts of p-hydroxyanisole into a reaction kettle, and dispersing at the rotating speed of 300rpm for 40min until the mixture is uniformly mixed.
And step B2, adding 10.7 parts of liquid polyurethane, 9 parts of filler nano calcium carbonate and 14.3 parts of dicyandiamide into the reaction kettle, and dispersing for 2 hours at the rotating speed of 800rpm until the components are uniformly mixed.
And step B3, adding 2.3 parts of diaryl iodate into the reaction kettle, dispersing for 30min at the rotating speed of 800rpm until the diaryl iodate and the diaryl iodate are uniformly mixed, and then defoaming for 30min in vacuum to obtain the dual-curing single-component epoxy resin adhesive.
Example 3
The preparation method of the dual-curing one-component epoxy resin adhesive comprises the following steps (by weight):
and step C1, adding 24.8 parts of furan modified epoxy resin, 42.7 parts of phenolic aldehyde modified epoxy resin, 6.2 parts of 3,3' - (oxybis-methylene) bis (3-ethyl) oxetane, KS 6031.7 parts of defoaming agent and 1.6 parts of 4-methoxyphenol into a reaction kettle, and dispersing at the rotating speed of 300rpm for 30min until the mixture is uniformly mixed.
And step C2, adding 14.1 parts of active nano calcium carbonate, 8.3 parts of filler glass powder and 8.5 parts of 2-methylimidazole into the reaction kettle, and dispersing at the rotating speed of 800rpm for 2 hours until the materials are uniformly mixed.
And step C3, adding 4.1 parts of triaryl iodate into the reaction kettle, dispersing for 30min at the rotating speed of 800rpm until the triaryl iodate and the epoxy resin are uniformly mixed, and then defoaming for 30min in vacuum to obtain the dual-curing single-component epoxy resin adhesive.
Performance testing
The following performance tests were performed on the dual-curing one-component epoxy resin adhesives prepared in the embodiment 1, the embodiment 2 and the embodiment 3 of the present invention, respectively:
(1) testing the photocuring positioning speed: the dual-curing single-component epoxy resin adhesive prepared in the embodiment of the invention is smeared on an aluminum plate, a small aluminum plate is covered on the aluminum plate, the glue is ensured to overflow to a certain extent, then the glue is irradiated for a certain time by an ultraviolet light source with the wavelength of 365nm, the glue has certain strength after the irradiation is carried out for a certain time, and the small aluminum plate can not move any more, so that the optical positioning speed shown in the following table 1 can be obtained.
(2) Heat curing positioning speed test: taking four containers, putting 10g of the dual-curing single-component epoxy resin adhesive prepared in the embodiment of the invention into each container, then respectively putting the containers into ovens at 70 ℃, 80 ℃, 90 ℃ and 100 ℃ for baking, and observing how much time the adhesive is cured and has certain hardness, so that the 70 ℃, 80 ℃, 90 ℃ and 100 ℃ heat curing speeds shown in the following table 1 can be obtained.
(3) And (3) testing the shear strength after photocuring: cutting a PC substrate into standard shear slices with the size of 25mm x 100mm, then coating the dual-curing single-component epoxy resin adhesive prepared in the embodiment of the invention on the standard shear slices, overlapping to form a bonding area with the size of 12.5mm x 25mm, applying a certain external force, and irradiating for 10min by using ultraviolet light with the wavelength of 365nm for curing, thereby obtaining a sample to be tested. After the glue is completely cured, the two ends of the sample piece to be tested are fastened by using a tensile testing machine, and the tensile shear strength of the sample piece to be tested is tested at the speed of 5mm/min, so that the shear strength of the PC substrate after being irradiated for 10min shown in the following table 1 can be obtained.
(4) Shear strength test after heat curing: cutting an aluminum substrate into standard cut pieces with the size of 25mm x 100mm, then coating the dual-curing single-component epoxy resin adhesive prepared in the embodiment of the invention on the standard cut pieces, overlapping to form a bonding area with the size of 12.5mm x 25mm, and then applying a certain external force to perform thermosetting, thereby obtaining the sample piece to be tested. After the glue is completely cured, the two ends of the sample piece to be tested are fastened by using a tensile testing machine, and the tensile shear strength of the sample piece to be tested is tested at the speed of 5mm/min, so that the thermal-cured aluminum shear strength shown in the following table 1 can be obtained.
(5) And (4) testing the storage stability: after the dual-curing single-component epoxy resin adhesive in the embodiment of the invention is prepared, the viscosity of the product is tested at normal temperature (24 ℃), and then the product is stored under the following conditions:
condition 1: stored at room temperature (24 ℃) for 3 months
Condition 2: storage at-5 ℃ for 18 months
After the storage is finished, the product is heated to 24 ℃, the viscosity of the product is tested, and the viscosity increase is not more than 50 percent, namely the storage property is qualified. The viscosities were measured as shown in table 1 below.
TABLE 1
As can be seen from table 1: the dual-curing single-component epoxy resin adhesive prepared in the embodiments 1 to 3 of the invention can be rapidly positioned under the irradiation of ultraviolet light. The dual-curing single-component epoxy resin adhesive prepared in the embodiments 1 to 3 of the invention can obtain products with different curing speeds after using different initiator components and content ratios, is suitable for various different curing working conditions, has higher mechanical strength after curing, has stronger thixotropy, and can be suitable for different bonding requirements. The viscosity increase of the dual-curing single-component epoxy resin adhesive prepared in the embodiments 1 to 3 is not more than 50% after being stored at 24 ℃ for 3 months, the viscosity increase of the dual-curing single-component epoxy resin adhesive is not more than 50% after being stored at-5 ℃ for 18 months, and the storage property is qualified, which indicates that the dual-curing single-component epoxy resin adhesive prepared in the embodiments of the present invention has excellent storage stability, can be stored at-5 ℃ for a long time, and can also be stored at normal temperature for 3 months.
In conclusion, the embodiment of the invention has excellent mechanical property and thixotropy, can be quickly positioned under the irradiation of ultraviolet light, has excellent storage stability, can be stored for a long time at-5 ℃ and can also be stored for 3 months at normal temperature.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any changes or substitutions that can be easily conceived by those skilled in the art within the technical scope of the present invention are included in the scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the claims.
Claims (10)
1. The dual-curing single-component epoxy resin adhesive is characterized by being prepared from the following raw materials in parts by weight:
20-40 parts of flexible epoxy resin, 30-50 parts of photosensitive epoxy resin, 5-14 parts of oxetane, 10-20 parts of toughening agent, 0.5-5 parts of stabilizer, 1-8 parts of photoinitiator, 5-20 parts of thermal initiator, 0.2-2 parts of defoaming agent and 2-15 parts of filler.
2. The dual-curing single-component epoxy resin adhesive according to claim 1, wherein the flexible epoxy resin is at least one of soybean oil modified epoxy resin, furfuryl alcohol modified epoxy resin, castor oil modified epoxy resin, polyurethane modified epoxy resin, furan modified epoxy resin and vinyl modified epoxy resin.
3. The dual-curing single-component epoxy resin adhesive according to claim 1 or 2, wherein the photosensitive epoxy resin is at least one of acrylic modified epoxy resin and phenolic modified epoxy resin.
4. The dual cure one-component epoxy resin adhesive according to claim 1 or 2, wherein the oxetane is at least one of 3,3' - (oxybis-methylene) bis (3-ethyl) oxetane, 3-ethyl-3- [4- [ (3-ethyloxetan-3-yl) methoxy ] butoxymethyl ] oxetane, and 1, 4-bis [ (3-ethyl-3-oxetanylmethoxy) methyl ] benzene.
5. The dual-curing single-component epoxy resin adhesive according to claim 1 or 2, wherein the toughening agent is at least one of liquid carboxyl-terminated nitrile rubber, liquid amino-terminated nitrile rubber, polyamide resin, propylene oxide rubber, liquid polyurethane, liquid silicone rubber, nano titanium dioxide, polyether and active nano calcium carbonate.
6. The dual-curing one-component epoxy resin adhesive according to claim 1 or 2, wherein the stabilizer is at least one of hydroquinone, p-benzoquinone, 2, 6-di-tert-butyl-p-cresol, benzoquinone, 1, 4-naphthoquinone, EDTA-4Na salt, EDTA-2Na salt, 4-methoxyphenol, anthraquinone, stearic acid, p-hydroxyanisole, and 2,2,6, 6-tetramethylpiperidine oxide.
7. The dual-curing one-component epoxy resin adhesive according to claim 1 or 2, wherein the photoinitiator is a diaryl iodate or a triaryl iodate.
8. The dual-curing one-component epoxy resin adhesive according to claim 1 or 2, wherein the thermal initiator is at least one of diaminodiphenyl sulfone, diaminodiphenyl methane, dicyandiamide, 2-methylimidazole, 2-ethyl-4-methylimidazole and 2-phenylimidazole.
9. The preparation method of the dual-curing single-component epoxy resin adhesive is characterized by comprising the following steps of:
step 1, weighing flexible epoxy resin, photosensitive epoxy resin, oxetane, a toughening agent, a stabilizing agent, a photoinitiator, a thermal initiator, a defoaming agent and a filler according to the formula of the dual-curing single-component epoxy resin adhesive as claimed in any one of claims 1 to 8;
step 2, adding the flexible epoxy resin, the photosensitive epoxy resin, the oxetane, the defoaming agent and the stabilizer into a reaction kettle, and uniformly dispersing and mixing;
step 3, adding the toughening agent, the filler and the thermal initiator into the reaction kettle, and uniformly dispersing and mixing;
and 4, adding the photoinitiator into the reaction kettle, uniformly dispersing and mixing, and then defoaming in vacuum for 30min to obtain the dual-curing single-component epoxy resin adhesive as claimed in any one of claims 1 to 8.
10. The method for preparing the dual-curing one-component epoxy resin adhesive according to claim 9, wherein the types and contents of the photoinitiator and the thermal initiator are adjusted to obtain dual-curing one-component epoxy resin adhesives with different curing speeds.
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