CN111218002A - High-refractive-index organic silicon tackifier containing boron and epoxy groups as well as preparation method and application thereof - Google Patents
High-refractive-index organic silicon tackifier containing boron and epoxy groups as well as preparation method and application thereof Download PDFInfo
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- CN111218002A CN111218002A CN202010113117.6A CN202010113117A CN111218002A CN 111218002 A CN111218002 A CN 111218002A CN 202010113117 A CN202010113117 A CN 202010113117A CN 111218002 A CN111218002 A CN 111218002A
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- refractive index
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- containing boron
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- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 229910052710 silicon Inorganic materials 0.000 title claims abstract description 34
- 239000010703 silicon Substances 0.000 title claims abstract description 34
- 125000003700 epoxy group Chemical group 0.000 title claims abstract description 31
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 229910052796 boron Inorganic materials 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 30
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 24
- 229910000077 silane Inorganic materials 0.000 claims abstract description 24
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000004327 boric acid Substances 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 18
- 239000003054 catalyst Substances 0.000 claims abstract description 17
- 239000003960 organic solvent Substances 0.000 claims abstract description 12
- 238000002156 mixing Methods 0.000 claims abstract description 10
- -1 vinyl methyl Chemical group 0.000 claims abstract description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 239000001301 oxygen Substances 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- 239000002318 adhesion promoter Substances 0.000 claims description 9
- 229920005989 resin Polymers 0.000 claims description 8
- 239000011347 resin Substances 0.000 claims description 8
- CVQVSVBUMVSJES-UHFFFAOYSA-N dimethoxy-methyl-phenylsilane Chemical compound CO[Si](C)(OC)C1=CC=CC=C1 CVQVSVBUMVSJES-UHFFFAOYSA-N 0.000 claims description 7
- ZLNAFSPCNATQPQ-UHFFFAOYSA-N ethenyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C=C ZLNAFSPCNATQPQ-UHFFFAOYSA-N 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000129 anionic group Chemical group 0.000 claims description 3
- OTARVPUIYXHRRB-UHFFFAOYSA-N diethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C)(OCC)CCCOCC1CO1 OTARVPUIYXHRRB-UHFFFAOYSA-N 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- DOYKFSOCSXVQAN-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CCO[Si](C)(OCC)CCCOC(=O)C(C)=C DOYKFSOCSXVQAN-UHFFFAOYSA-N 0.000 claims description 2
- LZMNXXQIQIHFGC-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CO[Si](C)(OC)CCCOC(=O)C(C)=C LZMNXXQIQIHFGC-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- MNFGEHQPOWJJBH-UHFFFAOYSA-N diethoxy-methyl-phenylsilane Chemical compound CCO[Si](C)(OCC)C1=CC=CC=C1 MNFGEHQPOWJJBH-UHFFFAOYSA-N 0.000 claims description 2
- MBGQQKKTDDNCSG-UHFFFAOYSA-N ethenyl-diethoxy-methylsilane Chemical compound CCO[Si](C)(C=C)OCC MBGQQKKTDDNCSG-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 229920001296 polysiloxane Polymers 0.000 claims 1
- 229920002379 silicone rubber Polymers 0.000 abstract description 30
- 239000004945 silicone rubber Substances 0.000 abstract description 14
- 239000004954 Polyphthalamide Substances 0.000 abstract description 12
- 229920006375 polyphtalamide Polymers 0.000 abstract description 12
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract description 8
- 229910052802 copper Inorganic materials 0.000 abstract description 8
- 239000010949 copper Substances 0.000 abstract description 8
- 239000007788 liquid Substances 0.000 abstract description 4
- 238000012360 testing method Methods 0.000 description 17
- 239000003957 anion exchange resin Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 9
- 239000012496 blank sample Substances 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 6
- 229920001971 elastomer Polymers 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- 238000003760 magnetic stirring Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000004944 Liquid Silicone Rubber Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229920002545 silicone oil Polymers 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- QYLFHLNFIHBCPR-UHFFFAOYSA-N 1-ethynylcyclohexan-1-ol Chemical compound C#CC1(O)CCCCC1 QYLFHLNFIHBCPR-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- 238000004100 electronic packaging Methods 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 230000005693 optoelectronics Effects 0.000 description 2
- 231100000572 poisoning Toxicity 0.000 description 2
- 230000000607 poisoning effect Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
Images
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- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/08—Macromolecular additives
-
- C—CHEMISTRY; METALLURGY
- 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
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Silicon Polymers (AREA)
- Epoxy Resins (AREA)
Abstract
The invention discloses an organic silicon tackifier with high refractive index and containing boron and epoxy groups, and a preparation method and application thereof. The method comprises the following steps: uniformly mixing boric acid, vinyl methyl dialkoxy silane, gamma-glycidyl ether oxygen propyl methyl dialkoxy silane, phenyl methyl dialkoxy silane and an organic solvent, adding an alkaline catalyst, reacting for 4-7 h at 65-95 ℃, finishing the reaction, and purifying to obtain the organic silicon tackifier containing boron and epoxy groups with high refractive index. The high-refractive-index organic silicon tackifier prepared by the invention is light orange transparent viscous liquid, has low viscosity and is easy to use. The preparation process disclosed by the invention is simple to operate, good in repeatability and controllability, capable of adjusting the refractive index of a product and remarkably improving the tackifying and connecting performance of the silicone rubber to the polyphthalamide and the copper plate.
Description
Technical Field
The invention belongs to the field of additives of organic silicon rubber, and particularly relates to an organic silicon tackifier with high refractive index and containing boron and epoxy groups, and a preparation method and application thereof.
Background
With the development and progress of electronic technology nowadays, electronic components and integrated circuits are becoming increasingly integrated, miniaturized and modularized, and the working environment is more demanding, which puts higher demands on the stability of electronic devices. The electronic packaging technology can strengthen the integrity of electronic devices, prevent moisture, dust and harmful gas from corroding the electronic devices, improve the resistance of the devices to external impact and vibration and stabilize the parameters of the devices. The properties of the encapsulating material thus determine to some extent the service life of the electronic components. Epoxy resin, polyurethane and organic silicon rubber are three electronic packaging materials which are most widely applied at present.
The addition type liquid silicone rubber is also one of organic silicone rubber, has the advantages of no by-product in the vulcanization process, low shrinkage rate, deep curing and the like, and is rapidly developed in the fields of electronic components, power circuit modules, large-scale integrated circuit boards, LEDs and the like. However, the addition type liquid silicone rubber is in a highly saturated state after being cured, and has low surface energy and poor adhesion performance with metal base materials (copper, aluminum, silver, gold, stainless steel, and the like) and non-metal base materials (PC, P BT, PPA, nylon, PCB boards, and the like). In consideration of the diversity of bonding substrates and the continuous improvement of the requirement on the bonding property in the practical application process, the development of corresponding tackifier and new species of bonding addition type liquid silica gel is always a research hotspot in the field. At present, three methods for improving the adhesion between silicone rubber and various materials are available: firstly, the surface of a substrate is treated by adopting a primer, the production process and the production time are increased, the production efficiency is reduced, and meanwhile, the primer mostly uses flammable solvents, so that the transportation danger and the environmental pollution are caused; secondly, the adhesive property is enhanced by changing the molecular structure of the base adhesive, but the method has no industrialization at present due to the complex actual production process and relatively high cost; thirdly, the adhesion is improved by adding the tackifier, the method is convenient and easy to operate, but the problems of poor compatibility with silicon rubber or silicon resin, easy poisoning of a catalyst and the like exist.
Chinese patent application CN105713201A discloses an organosilicon adhesion promoter for LED packaging high-refractive-index addition type silica gel, and a preparation method and application thereof. The preparation method comprises the steps of uniformly stirring the organosilicon compound containing hydroxyl and phenyl, the epoxy silane, the ester silane and the solvent at room temperature, adding the titanate catalyst, and reacting for a certain time at a proper temperature to prepare the organosilicon adhesion promoter containing epoxy groups and ester groups and having high refractive index.
Chinese patent application CN104774333A discloses an addition type organic silicon rubber tackifier capable of improving adhesion between addition type silicon rubber and a base material after medium-temperature curing, a preparation method and an application method thereof, wherein the tackifier is prepared from vinyl hydroxyl silicone oil, glycidyl ether alkoxy silicon hospital and a titanate catalyst, and the preparation method comprises the following steps: uniformly mixing vinyl hydroxyl silicone oil and glycidyl ether alkoxy silane at room temperature, adding titanate under the stirring state, and heating for a certain time to prepare the tackifier.
The traditional synthesis process of the organic silicon tackifier mostly adopts homogeneous catalysts, so that the catalyst residues exist in reaction products, the catalyst residues in the products are difficult to remove, the performance of the synthesized tackifier is adversely affected, and the silicone rubber is also affected to a certain extent after the organic silicon tackifier is added into the silicone rubber. Therefore, the synthesis method which has the advantages of simple synthesis process, environment-friendly and energy-saving production process and easy removal of the catalyst in the reaction process is provided, and has important significance for preparing the organic silicon tackifier.
Disclosure of Invention
In order to solve the problem that the addition type silicone rubber in the prior art has weak adhesion to polyphthalamide (PPA) and a metal copper plate, the invention aims to provide a preparation method of an organic silicon tackifier with high refractive index and containing boron and epoxy groups.
The invention also aims to provide the organic silicon tackifier with high refractive index and containing boron and epoxy groups, which is prepared by the method.
Still another object of the present invention is to provide the use of the above-mentioned high refractive index boron and epoxy group containing organosilicon adhesion promoter.
The purpose of the invention is realized by the following technical scheme:
a preparation method of the organic silicon tackifier with high refractive index and containing boron and epoxy groups comprises the following steps:
uniformly mixing boric acid, vinyl methyl dialkoxy silane, gamma-glycidyl ether oxygen propyl methyl dialkoxy silane, phenyl methyl dialkoxy silane and an organic solvent, adding an alkaline catalyst, reacting for 4-7 h at 65-95 ℃, finishing the reaction, and purifying to obtain the organic silicon tackifier containing boron and epoxy groups with high refractive index.
Preferably, the molar ratio of hydroxyl in the boric acid to alkoxy in the reaction system is 1: 2-1: 1, and the molar ratio of the vinylmethyldialkoxysilane, the gamma-glycidoxypropylmethyldialkoxysilane and the phenylmethyldialkoxysilane is 1:1: 1-3: 4: 2.
Preferably, the ratio of the boric acid to the organic solvent is 0.1-0.2 g/ml.
Preferably, the mixing mode is as follows: dissolving boric acid in an organic solvent, and uniformly mixing the boric acid with vinyl methyl dialkoxy silane, gamma-glycidyl ether oxygen propyl methyl dialkoxy silane and phenyl methyl dialkoxy silane.
More preferably, the mixing mode is as follows: dissolving boric acid in an organic solvent, adding the boric acid into a mixture of vinyl methyl dialkoxy silane, gamma-glycidyl ether oxypropyl methyl dialkoxy silane and phenyl methyl dialkoxy silane in a dropwise adding mode, and controlling the dropwise adding within 1-2 h.
Preferably, the vinylmethyldialkoxysilane is at least one of vinylmethyldimethoxysilane, vinylmethyldiethoxysilane, γ -methacryloxypropylmethyldimethoxysilane and γ -methacryloxypropylmethyldiethoxysilane.
Preferably, the gamma-glycidoxypropylmethyldialkoxysilane is at least one of gamma-glycidoxypropylmethyldimethoxysilane and gamma-glycidoxypropylmethyldiethoxysilane.
Preferably, the phenylmethyldialkoxysilane is at least one of phenylmethyldimethoxysilane and phenylmethyldiethoxysilane.
Preferably, the organic solvent is at least one of methanol, ethanol, isopropanol, toluene, and xylene.
Preferably, the basic catalyst is a basic anionic resin, more preferably a D296R basic anionic resin.
Preferably, the addition amount of the alkaline catalyst accounts for 1-2% of the total mass of the reactants.
Preferably, the reaction temperature is 70-90 ℃ and the reaction time is 4-6 hours.
Preferably, the purification method comprises the following steps: and (3) carrying out vacuum filtration on the crude product to remove the basic anion exchange resin catalyst, then carrying out vacuum distillation on the filtrate, and removing low-boiling-point substances in the system under the condition of 100 DEG/0.096 MPa.
The organic silicon tackifier containing boron and epoxy groups and having high refractive index is prepared by the method.
The application of the organic silicon tackifier containing boron and epoxy groups with high refractive index is disclosed.
Preferably, the application is in the field of bonding of addition type silicone rubber to polyphthalamide (PPA) and copper metal plates.
Compared with the prior art, the invention has the following advantages and beneficial effects:
(1) the preparation method has the advantages of simple preparation process, good repeatability and controllability, mild reaction conditions, easy collection of organic solvent in the reaction process and no environmental pollution.
(2) By changing the reaction conditions and the mixture ratio of reactants, the viscosity of the organic silicon tackifier with high refractive index containing boron and epoxy groups obtained by the reaction is 81.3 mPas, and the refractive index is 1.5035.
(3) The invention adopts the basic anion exchange resin as the catalyst of the reaction, and the basic anion exchange resin is easy to remove by decompression and suction filtration after the reaction is finished.
(4) The high-refractive-index organic silicon tackifier containing boron and epoxy groups, which is synthesized by the invention, can remarkably improve the bonding performance of silicon rubber, polyphthalamide (PPA) and a metal copper plate, and effectively solves the problem of weak bonding performance of addition type silicon rubber, polyphthalamide (PPA) and the metal copper plate.
(5) The organic silicon tackifier containing boron and epoxy groups and having high refractive index, which is synthesized by the invention, is suitable for addition type organic silicon rubber having high refractive index, and has good compatibility with silicon rubber and no catalyst poisoning phenomenon.
Drawings
Fig. 1 is a microscopic image of the surface of the silicone rubber after the blank sample was detached from the surface of the copper plate in test example 1.
FIG. 2 is a microscopic image of the surface of the silicone rubber after the blank sample of test example 1 was detached from the PPA surface.
Fig. 3 is a microscopic image of the surface of the silicone rubber after the adhesion promoter sample of example 1 added in test example 1 was detached from the surface of the copper plate.
FIG. 4 is a microscopic image of the surface of the silicone rubber after the sample of test example 1 with the tackifier added thereto was peeled from the PPA surface.
Detailed Description
The present invention will be described in further detail with reference to examples and drawings, but the embodiments of the present invention are not limited thereto.
The basic catalyst in the examples of this application is the D296R basic anion resin from the chemical plant of Nankai university of Tianjin.
Example 1
1.82g of methylphenyldimethoxysilane, 13.22g of vinylmethyldimethoxysilane and 39.74g of gamma-glycidyloxypropylmethyldiethoxysilane were charged into a 150ml three-necked flask equipped with magnetic stirring and temperature controller; 9.27g of boric acid solid powder was dissolved in 50ml of methanol, and then added to the above three-necked flask through a constant pressure dropping funnel, and the piston of the constant pressure funnel was adjusted to be dropped within 2 hours. The reaction temperature is increased to 75 ℃, alkaline anion exchange resin accounting for 1 percent of the total mass of the reactants is added and the reaction is carried out for 5 hours at constant temperature. After the reaction is finished, the product is decompressed and filtered to remove the alkaline anion exchange resin, then the filtrate is transferred to a round bottom distillation flask, and the by-product in the system is removed under the condition of 100 ℃/-0.096MPa, so that the light orange transparent organic silicon tackifier containing boron and epoxy groups and having high refractive index is prepared. The properties of the samples are shown in Table 1 and FIGS. 3 to 4.
Example 2
1.82g of methylphenyldimethoxysilane, 13.22g of vinylmethyldimethoxysilane and 39.74g of gamma-glycidyloxypropylmethyldiethoxysilane were charged into a 150ml three-necked flask equipped with magnetic stirring and a temperature controller, and 9.27g of boric acid solid powder was dissolved in 50ml of methanol and then charged into the above three-necked flask through a constant pressure dropping funnel, and the piston of the constant pressure funnel was adjusted to be dropped within 2 hours. The reaction temperature is increased to 65 ℃, alkaline anion exchange resin accounting for 1 percent of the total mass of the reactants is added and the reaction is carried out for 7 hours at constant temperature. After the reaction is finished, the product is decompressed and filtered to remove the alkaline anion exchange resin, then the filtrate is transferred to a round bottom distillation flask, and the by-product in the system is removed under the condition of 100 ℃/-0.096MPa, so that the light orange transparent organic silicon tackifier containing boron and epoxy groups and having high refractive index is prepared. The properties of the test specimens are shown in Table 1.
Example 3
1.82g of methylphenyldimethoxysilane, 13.22g of vinylmethyldimethoxysilane and 39.74g of gamma-glycidyloxypropylmethyldiethoxysilane were charged into a 150ml three-necked flask equipped with magnetic stirring and a temperature controller, and 9.27g of boric acid solid powder was dissolved in 50ml of methanol and then charged into the above three-necked flask through a constant pressure dropping funnel, and the piston of the constant pressure funnel was adjusted to be dropped within 2 hours. The reaction temperature is raised to 85 ℃, alkaline anion exchange resin accounting for 1 percent of the total mass of the reactants is added and the reaction is carried out for 4 hours at constant temperature. After the reaction is finished, the product is decompressed and filtered to remove the alkaline anion exchange resin, then the filtrate is transferred to a round bottom distillation flask, and the by-product in the system is removed under the condition of 100 ℃/-0.096MPa, so that the light orange transparent organic silicon tackifier containing boron and epoxy groups and having high refractive index is prepared. The properties of the test specimens are shown in Table 1.
Example 4
3.64g of methylphenyldimethoxysilane, 13.22g of vinylmethyldimethoxysilane and 39.74g of gamma-glycidyloxypropylmethyldiethoxysilane were charged into a 150ml three-necked flask equipped with magnetic stirring and a temperature controller, 9.27g of boric acid solid powder was dissolved in 50ml of methanol and then charged into the above three-necked flask through a constant pressure dropping funnel, and the piston of the constant pressure funnel was adjusted to be dropped within 2 hours. The reaction temperature is increased to 75 ℃, alkaline anion exchange resin accounting for 1 percent of the total mass of the reactants is added and the reaction is carried out for 5 hours at constant temperature. After the reaction is finished, the product is decompressed and filtered to remove the alkaline anion exchange resin, then the filtrate is transferred to a round bottom distillation flask, and the by-product in the system is removed under the condition of 100 ℃/-0.096MPa, so that the light orange transparent organic silicon tackifier containing boron and epoxy groups and having high refractive index is prepared. The properties of the test specimens are shown in Table 1.
Example 5
3.64g of methylphenyldimethoxysilane, 13.22g of vinylmethyldimethoxysilane and 49.68g of gamma-glycidyloxypropylmethyldiethoxysilane were charged into a 150ml three-necked flask equipped with magnetic stirring and a temperature controller, 9.27g of boric acid solid powder was dissolved in 50ml of methanol and then charged into the above three-necked flask through a constant pressure dropping funnel, and the piston of the constant pressure funnel was adjusted to be dropped within 2 hours. The reaction temperature is increased to 75 ℃, alkaline anion exchange resin accounting for 1 percent of the total mass of the reactants is added and the reaction is carried out for 5 hours at constant temperature. After the reaction is finished, the product is decompressed and filtered to remove the alkaline anion exchange resin, then the filtrate is transferred to a round bottom distillation flask, and the by-product in the system is removed under the condition of 100 ℃/-0.096MPa, so that the light orange transparent organic silicon tackifier containing boron and epoxy groups and having high refractive index is prepared. The properties of the test specimens are shown in Table 1.
Test example 1
72g of vinyl MQ silicon resin (product number is CF90-7, manufactured by Sichuan morning photoelectric technology Co., Ltd.), 6g of hydrogen-containing silicone oil and 0.39g of chloroplatinic acid catalyst are mixed and stirred uniformly to prepare an addition type liquid silicone rubber base rubber, the base rubber is divided into 6 parts, each part is 13g, and the parts are respectively marked as example 1, example 2, and,
Example 3, example 4, example 5 and a blank were added in a corresponding relationship with 0.13g of the tackifier prepared in each example, and the blank was added without any other additives, the samples were stirred uniformly, put into a vacuum drying oven for deaeration for 30min, then filled into a tensile sample, and put into an oven for curing at 90 ℃ for 1h and 150 ℃ for 2 h. The samples were tested for shear strength using a universal tester and the results are shown in Table 1. Adding the tackifier prepared in example 1 into silicone rubber, and performing SEM test on the silicone rubber subjected to the shear strength test, wherein the test results are shown in FIGS. 3-4; the blank sample is taken for the silicon rubber subjected to the shear strength test and is subjected to SEM test, and the test result is shown in figures 1-2.
Test example 2
98g of vinyl MQ silicon resin (Sichuan morning flying opto-electronic technology Co., Ltd., product number of CF90-7), 7g of hydrogen-containing silicon oil, 1.05g of inhibitor (1-ethynylcyclohexanol) and 0.525g of chloroplatinic acid catalyst are mixed and stirred uniformly to prepare an addition type liquid silicon rubber base rubber, the base rubber is divided into 6 parts, each part is 15g, the parts are respectively marked as example 1, example 2, example 3, example 4, example 5 and a blank sample, 0.23g of the tackifier prepared in each example is respectively added according to the corresponding relation, the blank sample is not added with any other additive, the various samples are stirred uniformly, put into a vacuum drying oven for defoaming for 30min, then filled into a tensile sample strip, and put into an oven to be cured for 1h at the temperature of 90 ℃ and cured for 2h at the temperature of 150 ℃. The samples were tested for shear strength using a universal tester and the results are shown in Table 1.
Test example 3
84g of vinyl MQ silicon resin (product number is CF90-7, manufactured by Sichuan morning flying opto-electronic technology Co., Ltd.), 6g of hydrogen-containing silicon oil, 0.9g of inhibitor (1-ethynylcyclohexanol) and 0.45g of chloroplatinic acid catalyst are mixed and stirred uniformly to prepare an addition type liquid silicon rubber base rubber, the base rubber is divided into 6 parts, each part is 15g, the parts are respectively marked as example 1, example 2, example 3, example 4, example 5 and a blank sample, 0.23g of the tackifier prepared in each example is respectively added according to the corresponding relation, the blank sample is not added with any other additive, the various samples are stirred uniformly, the mixture is placed into a vacuum drying oven for defoaming for 30min, then the mixture is filled into a tensile sample strip, and the tensile sample strip is placed in an oven to be cured for 1h at the temperature of 90 ℃ and cured for 2h at the temperature of 150 ℃. The samples were tested for shear strength using a universal tester and the results are shown in Table 1.
The test methods for the properties of the samples in table 1 are as follows:
1. measuring the viscosity of the synthesized organic silicon tackifier according to GB/T2794-1995;
2. measuring the refractive indexes of the synthesized organic silicon tackifier and the addition type liquid silicone rubber according to GB/T614-2006;
3. the shear strength of the addition-type silicone rubber and the bonded substrate was measured according to GB/T13936-1992.
TABLE 1
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (10)
1. The preparation method of the organic silicon tackifier with high refractive index and containing boron and epoxy groups is characterized by comprising the following steps:
uniformly mixing boric acid, vinyl methyl dialkoxy silane, gamma-glycidyl ether oxygen propyl methyl dialkoxy silane, phenyl methyl dialkoxy silane and an organic solvent, adding an alkaline catalyst, reacting for 4-7 h at 65-95 ℃, finishing the reaction, and purifying to obtain the organic silicon tackifier containing boron and epoxy groups with high refractive index.
2. The method for preparing the organosilicon tackifier with high refractive index and containing boron and epoxy groups according to claim 1, wherein the molar ratio of hydroxyl groups in the boric acid to alkoxy groups in a reaction system is 1: 2-1: 1, and the molar ratio of the vinylmethyldialkoxysilane, the gamma-glycidoxypropylmethyldialkoxysilane and the phenylmethyldialkoxysilane is 1:1: 1-3: 4: 2.
3. The method of claim 1 or 2, wherein the vinylmethyldialkoxysilane is at least one of vinylmethyldimethoxysilane, vinylmethyldiethoxysilane, γ -methacryloxypropylmethyldimethoxysilane, and γ -methacryloxypropylmethyldiethoxysilane;
the gamma-glycidoxypropylmethyldiethoxysilane is at least one of gamma-glycidoxypropylmethyldimethoxysilane and gamma-glycidoxypropylmethyldiethoxysilane;
the phenylmethyldialkoxysilane is at least one of phenylmethyldimethoxysilane and phenylmethyldiethoxysilane.
4. The preparation method of the high-refractive-index boron and epoxy group-containing organosilicon tackifier according to claim 1 or 2, wherein the basic catalyst is a basic anionic resin, and the addition amount of the basic catalyst accounts for 1-2% of the total reaction mass.
5. The method for preparing the high-refractive-index organosilicon adhesion promoter containing boron and epoxy groups according to claim 1 or 2, wherein the mixing is carried out by: dissolving boric acid in an organic solvent, and uniformly mixing the boric acid with vinyl methyl dialkoxy silane, gamma-glycidyl ether oxygen propyl methyl dialkoxy silane and phenyl methyl dialkoxy silane.
6. The method for preparing the high refractive index boron and epoxy group containing organosilicon adhesion promoter according to claim 5, wherein the mixing is performed by: dissolving boric acid in an organic solvent, adding the boric acid into a mixture of vinyl methyl dialkoxy silane, gamma-glycidyl ether oxypropyl methyl dialkoxy silane and phenyl methyl dialkoxy silane in a dropwise adding mode, and controlling the dropwise adding within 1-2 h.
7. The method for preparing the organosilicon tackifier containing boron and epoxy groups and having high refractive index according to claim 1 or 2, wherein the ratio of the boric acid to the organic solvent is 0.1-0.2 g/ml; the reaction temperature is 70-90 ℃, and the reaction time is 4-6 hours.
8. The method for preparing the high refractive index organosilicon adhesion promoter containing boron and epoxy groups according to claim 1 or 2, wherein the organic solvent is at least one of methanol, ethanol, isopropanol, toluene and xylene.
9. A high refractive index organosilicon adhesion promoter containing boron and epoxy groups obtainable by a process as claimed in any one of claims 1 to 8.
10. Use of a high refractive index boron and epoxy group containing silicone adhesion promoter according to claim 9.
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113698611A (en) * | 2021-09-01 | 2021-11-26 | 福建师范大学 | Polymer with main chain of Si-O-B-O structure and method for toughening and modifying polylactic acid by using polymer |
CN113773503A (en) * | 2021-08-17 | 2021-12-10 | 广东万木新材料科技有限公司 | Boron-containing organic silicon tackifier and preparation method and application thereof |
CN114231247A (en) * | 2021-11-30 | 2022-03-25 | 湖北双键精细化工有限公司 | Room-temperature-curing two-component addition-type self-adhesive high-temperature-resistant silica gel and preparation method thereof |
CN114854022A (en) * | 2022-04-12 | 2022-08-05 | 华南理工大学 | High-refractive-index methacryloxy-containing organic silicon tackifier and preparation method and application thereof |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20110112221A1 (en) * | 2005-04-07 | 2011-05-12 | Momentive Performance Materials Inc. | Epoxy silane oligomer and coating composition containing same |
CN102566278A (en) * | 2010-09-22 | 2012-07-11 | Jsr株式会社 | Siloxane polymer composition, cured film and method for forming the cured film |
CN105802532A (en) * | 2016-05-26 | 2016-07-27 | 清远市美乐仕油墨有限公司 | Silicon boron tackifier, preparation method thereof and application thereof in double-component LED packaging gel |
CN108164704A (en) * | 2017-12-23 | 2018-06-15 | 广东新翔星科技股份有限公司 | The preparation method of high refractive index additional organosilicon packaging plastic adhesive accelerant |
CN109762167A (en) * | 2018-12-14 | 2019-05-17 | 中国科学院深圳先进技术研究院 | A kind of LED small-size chips heat conductive insulating die bond material and preparation method thereof |
CN109824899A (en) * | 2019-02-27 | 2019-05-31 | 华南理工大学 | A kind of boracic organic silicon rigidity-increasing stick of linear structure and preparation method thereof |
CN109824903A (en) * | 2019-02-27 | 2019-05-31 | 华南理工大学 | A kind of high refractive index boracic organic silicon rigidity-increasing stick and preparation method thereof |
-
2020
- 2020-02-24 CN CN202010113117.6A patent/CN111218002B/en not_active Expired - Fee Related
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20110112221A1 (en) * | 2005-04-07 | 2011-05-12 | Momentive Performance Materials Inc. | Epoxy silane oligomer and coating composition containing same |
CN102566278A (en) * | 2010-09-22 | 2012-07-11 | Jsr株式会社 | Siloxane polymer composition, cured film and method for forming the cured film |
CN105802532A (en) * | 2016-05-26 | 2016-07-27 | 清远市美乐仕油墨有限公司 | Silicon boron tackifier, preparation method thereof and application thereof in double-component LED packaging gel |
CN108164704A (en) * | 2017-12-23 | 2018-06-15 | 广东新翔星科技股份有限公司 | The preparation method of high refractive index additional organosilicon packaging plastic adhesive accelerant |
CN109762167A (en) * | 2018-12-14 | 2019-05-17 | 中国科学院深圳先进技术研究院 | A kind of LED small-size chips heat conductive insulating die bond material and preparation method thereof |
CN109824899A (en) * | 2019-02-27 | 2019-05-31 | 华南理工大学 | A kind of boracic organic silicon rigidity-increasing stick of linear structure and preparation method thereof |
CN109824903A (en) * | 2019-02-27 | 2019-05-31 | 华南理工大学 | A kind of high refractive index boracic organic silicon rigidity-increasing stick and preparation method thereof |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113773503A (en) * | 2021-08-17 | 2021-12-10 | 广东万木新材料科技有限公司 | Boron-containing organic silicon tackifier and preparation method and application thereof |
CN113773503B (en) * | 2021-08-17 | 2022-08-19 | 广东万木新材料科技有限公司 | Boron-containing organic silicon tackifier and preparation method and application thereof |
CN113698611A (en) * | 2021-09-01 | 2021-11-26 | 福建师范大学 | Polymer with main chain of Si-O-B-O structure and method for toughening and modifying polylactic acid by using polymer |
CN114231247A (en) * | 2021-11-30 | 2022-03-25 | 湖北双键精细化工有限公司 | Room-temperature-curing two-component addition-type self-adhesive high-temperature-resistant silica gel and preparation method thereof |
CN114231247B (en) * | 2021-11-30 | 2023-04-07 | 湖北双键精细化工有限公司 | Room-temperature-curing two-component addition-type self-adhesive high-temperature-resistant silica gel and preparation method thereof |
CN114854022A (en) * | 2022-04-12 | 2022-08-05 | 华南理工大学 | High-refractive-index methacryloxy-containing organic silicon tackifier and preparation method and application thereof |
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