CN110643321A - Electronic material glue solution and application thereof - Google Patents
Electronic material glue solution and application thereof Download PDFInfo
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- CN110643321A CN110643321A CN201910951744.4A CN201910951744A CN110643321A CN 110643321 A CN110643321 A CN 110643321A CN 201910951744 A CN201910951744 A CN 201910951744A CN 110643321 A CN110643321 A CN 110643321A
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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
- C09J179/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09J161/00 - C09J177/00
- C09J179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C09J179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C09J179/085—Unsaturated polyimide precursors
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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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/12—Unsaturated polyimide precursors
-
- 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
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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
- 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
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- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Reinforced Plastic Materials (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
The invention discloses an electronic material glue solution and application thereof. The preparation method comprises the following steps of blending 2-allyl phenyl glycidyl ether and terephthalic acid in acetonitrile, and carrying out esterification reaction under the condition that quaternary ammonium salt is used as a catalyst to obtain bis (3- (2-allyl phenoxy) -2-hydroxypropyl) terephthalate containing reversible dynamic groups; then, the bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate, the bismaleimide, the polyphenylene oxide coated mesoporous silicon dioxide and the solvent are mixed uniformly to prepare the electronic material glue solution. The electronic material glue solution prepared by the invention has good dielectric property and heat resistance when being used for preparing electronic materials, can realize remolding under the hot pressing condition, and has wide application prospect.
Description
Technical Field
The invention relates to an electronic material glue solution, a preparation method and application thereof.
Background
Bismaleimide is a thermosetting resin, has excellent mechanical properties and heat resistance, is widely applied to the fields of aerospace and the like, and currently, copper-clad plates based on bismaleimide resin are reported in a lot.
In recent years, new demands have been made on substrates for high-frequency applications, because antennas, base stations, and satellite communications require high signal transmission speeds at high frequencies without distortion, and particularly, signal transmission capabilities under high-frequency and high-temperature and high-humidity conditions are consistent with those under normal conditions.
Disclosure of Invention
Aiming at the defects in the prior art, the invention provides the bismaleimide resin adhesive solution with secondary curing, high heat resistance and high dielectric property and the preparation method thereof, and provides a method for preparing the repairable copper-clad plate.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
an electronic material glue solution, wherein the preparation method of the electronic material glue solution comprises the following steps:
(1) reacting 2-allylphenyl glycidyl ether with terephthalic acid in the presence of quaternary ammonium salt to prepare bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate;
(2) stirring and mixing bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate, bismaleimide, a zinc compound, mesoporous silica coated by polyphenyl ether and a solvent to obtain an electronic material glue solution.
The polyphenylene ether-coated mesoporous silica is an existing material, is obtained from embodiment one of CN109021235A, and can provide good dielectric properties.
In the invention, epoxy chloropropane is added into a mixed solution of 2-allyl phenol, sodium hydroxide, quaternary ammonium salt and tetrahydrofuran to react to prepare 2-allyl phenyl glycidyl ether.
In the technical scheme, in the step (1), the mass ratio of the 2-allyl phenyl glycidyl ether to the terephthalic acid to the quaternary ammonium salt is 120: 40-50: 5-10, the reaction temperature is 65-80 ℃, and the reaction time is 8-12 hours; in the step (2), the mass ratio of the bismaleimide, the bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate, the zinc compound and the polyphenylene oxide coated mesoporous silica is 50: 75-80: 6-6.5: 1.5.
In the technical scheme, in the step (2), the mesoporous silica coated with bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate, bismaleimide, a zinc compound and polyphenyl ether is stirred at 130-135 ℃ for 50-60 min, and then mixed with a solvent to obtain the electronic material glue solution.
In the technical scheme, the quaternary ammonium salt is tetramethyl ammonium bromide and/or tetrabutyl ammonium bromide; the zinc compound is zinc acetylacetonate hydrate; the bismaleimide is one or more of N, N '-4, 4' -diphenylmethane bismaleimide, N '- (1, 4-phenylene) bismaleimide and N, N' -m-phenylene bismaleimide; the solid content of the electronic material glue solution is 60-62%; the solvent is a mixture of N, N-dimethylformamide and butanone.
The bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate and bismaleimide system has good plasticity and can be used for preparing shape memory materials and wear-resistant materials.
Compared with the prior art, the invention has the beneficial effects that:
1. the invention synthesizes a novel diallyl compound containing reversible dynamic groups, which is used for modifying bismaleimide and preparing a novel electronic material glue solution containing reversible covalent bonds.
2. Compared with the traditional thermosetting SMPs, the remodelable shape memory bismaleimide prepared by the glue solution has good shape memory performance and remodeling performance.
3. Compared with the traditional 2, 2' -diallyl bisphenol A, the novel diallyl compound-bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate provided by the invention is synthesized without high-temperature rearrangement, the synthesis process is simple, and the required energy consumption is low; compared with the traditional 2, 2' -diallyl bisphenol A, the bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate synthesized by the method is non-bisphenol A type, so that the risks of carcinogenesis, teratogenicity, influence on fertility and the like of the bisphenol A are avoided.
Drawings
FIG. 1 is a reaction scheme for synthesizing 2-allylphenyl glycidyl ether and bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate prepared according to the present invention.
FIG. 2 shows the NMR spectrum of 2-allylphenyl glycidyl ether prepared in example 1 of the present invention: (1H-NMR)。
FIG. 3 is a drawing showing bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate prepared in example 1 of the present invention1H-NMR。
FIG. 4 is a NMR spectrum of bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate prepared in example 1 of the present invention (C13C-NMR)。
FIG. 5 is a high resolution mass spectrum of bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate prepared in example 1 of the present invention.
Detailed Description
The technical solution of the present invention is further described with reference to the accompanying drawings and examples.
The preparation method of the electronic material glue solution comprises the following steps:
(1) reacting 2-allylphenyl glycidyl ether with terephthalic acid in the presence of quaternary ammonium salt to prepare bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate;
(2) stirring and mixing bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate, bismaleimide, a zinc compound, mesoporous silica coated by polyphenyl ether and a solvent to obtain an electronic material glue solution.
Synthesis example
Mixing 120g of 2-allylphenol, 140g of sodium hydroxide, 10g of tetrabutylammonium bromide and 230g of tetrahydrofuran by mass, and carrying out heat preservation reaction for 1.5h at 35 ℃ under the stirring condition to obtain a solution A; slowly dropwise adding 270g of epoxy chloropropane into the solution A, and keeping the temperature at 35 ℃ and stirring for reacting for 6 hours; and after the reaction is finished, removing tetrahydrofuran and epichlorohydrin by vacuum rotary evaporation to obtain a crude product. Washing the crude product with saturated ammonium chloride solution (200mL × 2) and deionized water (200mL × 2), and separating and purifying with chromatographic column to obtain yellow transparent liquid, i.e. 2-allyl phenyl glycidyl ether, with yield of about 93%, its reaction formula and1H-NMR is shown in the attached figures 1 and 2 respectively. Mixing 120g of 2-allyl phenyl glycidyl ether, 45g of terephthalic acid, 10g of tetrabutylammonium bromide and 230g of acetonitrile by mass, and carrying out heat preservation reaction for 8 hours at 70 ℃ under the stirring condition; after the reaction is finished, removing acetonitrile by vacuum rotary evaporation to obtain a crude product. Washing the crude product with saturated sodium bicarbonate solution (200mL × 2) and deionized water (200mL × 2), and separating and purifying with chromatographic column to obtain yellow transparent viscous liquid, i.e. bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate with yield of 86%, according to the reaction formula,1H-NMR、13C-NMR and high resolution mass spectra are shown in FIGS. 1, 3, 4 and 5, respectively, for the following examples.
Completely dissolving 2g of polyphenylene oxide (vinyl-terminated polyphenylene oxide (PPO. MX9000-111) with the number average molecular weight of 1100) in 25ml of toluene to obtain a polyphenylene oxide solution, then adding 0.6g of mesoporous silica (UC-S-1), stirring and dispersing, adding into 500ml of aqueous solution of sodium dodecyl sulfate surfactant with the mass concentration of 0.15% to form an oil-in-water system, stirring for 4 hours, washing and filtering precipitates, and performing vacuum drying at 120 ℃ for 4 hours to obtain the polyphenylene oxide-coated mesoporous silica, wherein the mass ratio of the polyphenylene oxide to the mesoporous silica is 3.3: 1. Because the polyphenyl ether is insoluble in water, the separated polyphenyl ether can be deposited or adsorbed on the surface of the mesoporous silicon dioxide along with the gradual volatilization of the toluene solvent, and the mesopores are sealed.
EXAMPLE A preparation of an electronic Material glue solution
Mixing 50g of N, N '-4, 4' -diphenylmethane bismaleimide, 76.17g of bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate, 6.29g (22.3mmol) of zinc acetylacetonate hydrate and 1.5g of polyphenylene oxide-coated mesoporous silica, stirring at 130 ℃, carrying out prepolymerization for 60min to obtain a prepolymer, and sampling and testing DSC (10 ℃/min, the maximum reaction exothermic peak is 242.8 ℃); and cooling the prepolymer to room temperature, adding the cooled prepolymer into a mixture of N, N-dimethylformamide and butanone in a mass ratio of 2: 8, and stirring at room temperature for 2 hours to obtain an electronic material glue solution, wherein the solid content of the electronic material glue solution is 60%.
Preparation of copper-clad plate
Using 1080 fiber glass cloth (Shanghai macrosum) to dip the resin liquid to obtain a prepreg, and then drying (160 ℃ for 40 seconds) to remove the solvent to obtain a prepreg; and (3) overlapping 8 prepregs, covering copper foils (1 ounce) on two sides of the prepregs, and performing high-temperature hot-pressing curing in a press to prepare the electronic material glue solution.
The high-temperature hot-pressing curing process comprises the following steps: 150 ℃/1h/0.5MPa +180 ℃/2h/1MPa +200 ℃/1h/1MPa +220 ℃/1h/2 MPa; and naturally cooling and demoulding to obtain the copper-clad plate.
Preparation of electronic insulating material
And (3) overlapping 8 semi-cured sheets of the embodiments, pressing and covering conventional release films on two sides of the semi-cured sheets, and performing high-temperature hot-pressing curing in a press to prepare the electronic material glue solution. The high-temperature hot-pressing curing process comprises the following steps: 150 ℃/1h/0.5MPa +180 ℃/2h/1MPa +200 ℃/1h/1MPa +220 ℃/1h/2 MPa; and naturally cooling and demoulding to obtain the electronic insulating material.
Comparative example 1
50g of N, N '-4, 4' -diphenylmethane bismaleimide, 76.17g of bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate and 6.29g of zinc acetylacetonate hydrate were mixed, and stirred at 130 ℃ to perform prepolymerization for 60min, thereby obtaining a prepolymer. And replacing the prepolymer in the first embodiment with the prepolymer in the second embodiment, keeping the rest unchanged to obtain a comparison electronic material glue solution, and preparing a comparison copper-clad plate and a comparison insulating material by the same method.
Comparative example No. two
A comparative electronic material glue solution was obtained by replacing bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate of example one with 73.41g (139.5mmol) of bis (3- (2-allylphenoxy) -2-hydroxypropyl) adipate, and the remainder was unchanged, and a comparative copper clad laminate and a comparative insulating material were prepared in the same manner.
Performance testing
Secondary curing capability. According to the IPC-TM-6502.4.4, a bending strength test board (process for preparing an electronic insulating material) is prepared by equally dividing one electronic insulating material into four pieces, taking any two pieces for initial bending strength test, and using a 5512 impact instrument to drop the weight of the rest two pieces to the extent that a resin layer has cracks and glass cloth is not damaged, and then, using the board to test the bending strength of the boardAnd (3) hot-pressing the two boards after the dropping hammer for 5h under the conditions that the temperature is 270 ℃ and the pressure is 30MPa, naturally cooling and demoulding to obtain a secondary solidified board, wherein the appearance of the secondary solidified board is not cracked and is almost the same as the initial board. The flexural strength is measured according to the standard (three averages in N/mm)2) The initial values are 493 (warp direction) and 457 (weft direction), and the secondary values are 486 (warp direction) and 450 (weft direction) after secondary curing. In the same method, if the diallyl bisphenol A modified bismaleimide resin is adopted to prepare the plate (with a conventional formula), secondary curing cannot be performed, the plate is hot-pressed for 5 hours at the temperature of 270 ℃ and the pressure of 30MPa, and the plate is demoulded after natural cooling, and the drop hammer is still fuzzy and has cracks.
Table 1 copper-clad plate prepared by embodiment and comparative example
Wherein, TgThe glass transition temperature is obtained by DMA test (1Hz, 3 ℃/min, 20-350 ℃, three-point bending); the dielectric constant and dielectric loss of the panels at room temperature were tested using a Novocontrol Concept 80 dielectric tester, Germany.
Table 1 shows the above examples and the performance tests related to the comparative examples, and it can be seen that the glue solution prepared by using the polyphenylene oxide-coated mesoporous silica and bismaleimide together can ensure the heat resistance and simultaneously show excellent dielectric properties when used for preparing the copper-clad plate.
Claims (10)
1. The electronic material glue solution is characterized in that the preparation method of the electronic material glue solution comprises the following steps:
(1) reacting 2-allylphenyl glycidyl ether with terephthalic acid in the presence of quaternary ammonium salt to prepare bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate;
(2) stirring and mixing bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate, bismaleimide, a zinc compound, mesoporous silica coated by polyphenyl ether and a solvent to obtain an electronic material glue solution.
2. The electronic material glue solution of claim 1, wherein epoxy chloropropane is added into a mixed solution of 2-allyl phenol, sodium hydroxide, quaternary ammonium salt and tetrahydrofuran to react to prepare 2-allyl phenyl glycidyl ether.
3. The electronic material glue solution according to claim 1, wherein in the step (1), the mass ratio of the 2-allyl phenyl glycidyl ether to the terephthalic acid to the quaternary ammonium salt is 120: 40-50: 5-10, the reaction temperature is 65-80 ℃, and the reaction time is 8-12 hours.
4. The electronic material glue solution of claim 1, wherein the quaternary ammonium salt is tetramethylammonium bromide and/or tetrabutylammonium bromide; the zinc compound is zinc acetylacetonate hydrate.
5. The electronic material glue solution of claim 1, wherein in the step (2), the mass ratio of the bismaleimide, the bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate, the zinc compound and the polyphenylene oxide coated mesoporous silica is 50: 75-80: 6-6.5: 1.5.
6. The electronic material glue solution of claim 1, wherein in the step (2), the mesoporous silica coated with bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate, bismaleimide, a zinc compound and polyphenylene oxide is stirred at 130-135 ℃ for 50-60 min, and then mixed with a solvent to obtain the electronic material glue solution.
7. The electronic material glue solution according to claim 6, wherein the solid content of the electronic material glue solution is 60-62%; the solvent is a mixture of N, N-dimethylformamide and butanone.
8. The electronic material glue solution of claim 7, wherein the mass ratio of the N, N-dimethylformamide to the butanone is 2: 8.
9. The electronic material glue solution of claim 1, wherein the bismaleimide is one or more of N, N '-4, 4' -diphenylmethane bismaleimide, N '- (1, 4-phenylene) bismaleimide, and N, N' -m-phenylene bismaleimide.
10. The use of the electronic material glue solution of claim 1 in the preparation of circuit transmission materials.
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| CN104974346A (en) * | 2015-07-16 | 2015-10-14 | 大连理工大学 | Preparation method of liquid-crystal allyl-compound-modified bismaleimide resin |
| US20160168330A1 (en) * | 2014-12-11 | 2016-06-16 | Nan Ya Plastics Corporation | Fluorine-containing modified bismaleimide resin |
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| US20180179424A1 (en) * | 2016-12-23 | 2018-06-28 | Industrial Technology Research Institute | Adhesive composition and composite substrate employing the same |
| CN109232890A (en) * | 2016-12-09 | 2019-01-18 | 苏州大学 | A kind of preparation method of low dielectric bismaleimide resin system performed polymer |
| CN109929109A (en) * | 2019-03-19 | 2019-06-25 | 武汉理工大学 | A kind of high tenacity high-low temperature resistant Bismaleimides resin pre-polymer and preparation method thereof |
| CN110088153A (en) * | 2016-12-20 | 2019-08-02 | Dic株式会社 | Composition, solidfied material and laminated body |
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2019
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Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US20160168330A1 (en) * | 2014-12-11 | 2016-06-16 | Nan Ya Plastics Corporation | Fluorine-containing modified bismaleimide resin |
| CN104861652A (en) * | 2015-05-28 | 2015-08-26 | 苏州生益科技有限公司 | Thermosetting resin composition, and prepreg and laminated board made from thermosetting resin composition |
| CN104974346A (en) * | 2015-07-16 | 2015-10-14 | 大连理工大学 | Preparation method of liquid-crystal allyl-compound-modified bismaleimide resin |
| CN108047715A (en) * | 2015-09-02 | 2018-05-18 | 苏州益可泰电子材料有限公司 | The preparation method of high-frequency electronic dielectric material |
| CN109232890A (en) * | 2016-12-09 | 2019-01-18 | 苏州大学 | A kind of preparation method of low dielectric bismaleimide resin system performed polymer |
| CN110088153A (en) * | 2016-12-20 | 2019-08-02 | Dic株式会社 | Composition, solidfied material and laminated body |
| US20180179424A1 (en) * | 2016-12-23 | 2018-06-28 | Industrial Technology Research Institute | Adhesive composition and composite substrate employing the same |
| CN109929109A (en) * | 2019-03-19 | 2019-06-25 | 武汉理工大学 | A kind of high tenacity high-low temperature resistant Bismaleimides resin pre-polymer and preparation method thereof |
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