CN110713616B - Material for electronics and use thereof - Google Patents

Material for electronics and use thereof Download PDF

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CN110713616B
CN110713616B CN201910951742.5A CN201910951742A CN110713616B CN 110713616 B CN110713616 B CN 110713616B CN 201910951742 A CN201910951742 A CN 201910951742A CN 110713616 B CN110713616 B CN 110713616B
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electronic material
bismaleimide
hydroxypropyl
terephthalate
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CN110713616A (en
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彭代信
宁礼健
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Suzhou Yiketai Electronic Material Co ltd
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B15/00—Layered products comprising a layer of metal
    • B32B15/14—Layered products comprising a layer of metal next to a fibrous or filamentary layer
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B15/00—Layered products comprising a layer of metal
    • B32B15/20—Layered products comprising a layer of metal comprising aluminium or copper
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B33/00—Layered products characterised by particular properties or particular surface features, e.g. particular surface coatings; Layered products designed for particular purposes not covered by another single class
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
    • B32B5/02—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by structural features of a fibrous or filamentary layer
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
    • B32B7/04—Interconnection of layers
    • B32B7/06—Interconnection of layers permitting easy separation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/24—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran
    • C07C67/26—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran with an oxirane ring
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2260/00—Layered product comprising an impregnated, embedded, or bonded layer wherein the layer comprises an impregnation, embedding, or binder material
    • B32B2260/02—Composition of the impregnated, bonded or embedded layer
    • B32B2260/021—Fibrous or filamentary layer
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2260/00—Layered product comprising an impregnated, embedded, or bonded layer wherein the layer comprises an impregnation, embedding, or binder material
    • B32B2260/04—Impregnation, embedding, or binder material
    • B32B2260/046—Synthetic resin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2262/00—Composition or structural features of fibres which form a fibrous or filamentary layer or are present as additives
    • B32B2262/10—Inorganic fibres
    • B32B2262/101—Glass fibres
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2379/00—Characterised by the use of 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 C08J2361/00 - C08J2377/00
    • C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08J2379/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • 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
    • C08K7/00—Use of ingredients characterised by shape
    • C08K7/22—Expanded, porous or hollow particles
    • C08K7/24—Expanded, porous or hollow particles inorganic
    • C08K7/26—Silicon- containing 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
    • C08K9/00—Use of pretreated ingredients
    • C08K9/10—Encapsulated ingredients

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  • Medicinal Chemistry (AREA)
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Abstract

The invention discloses an electronic material 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 mixing the bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate, bismaleimide, the mesoporous silicon dioxide coated by polyphenyl ether and a solvent uniformly, and then dipping glass cloth to prepare the electronic material. The electronic material prepared from the electronic material has good dielectric property and heat resistance, can realize remolding under a hot pressing condition, and has wide application prospect.

Description

Material for electronics and use thereof
Technical Field
The invention relates to an electronic material and a preparation method and application thereof.
Background
At present, the copper-clad plate based on bismaleimide resin is reported a lot, bismaleimide is thermosetting resin, has excellent mechanical property and heat resistance, and is widely applied to the fields of aerospace and the like, but due to the inherent defects of the thermosetting resin, the existing copper-clad plate cannot be cured for the second time, and once the defects such as resin cracks occur, the existing copper-clad plate can only be scrapped, so that serious resource waste and environmental pollution can be caused. 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 mixture prepreg 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 laminate.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
a material for electronics, the method for preparing the material for electronics comprising the steps of:
(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;
(3) impregnating the reinforcing material with a material glue solution for electronics to obtain a prepreg; heating the prepreg to obtain the electronic material.
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 bismaleimide, bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate, zinc compound and polyphenylene oxide coated mesoporous silica is 50: 75-80: 6-6.5: 1.5; in the step (3), the heating temperature is 160 ℃ and the heating time is 40-45 seconds.
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 glue solution of the electronic material.
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 reinforcing material is fiber glass cloth; 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 the novel diallyl compound containing reversible dynamic groups, which is used for modifying bismaleimide and preparing the novel electronic material containing reversible covalent bonds.
2. Compared with the traditional thermosetting SMPs, the remodelable shape memory bismaleimide prepared by the material for the electronic 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 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;
(3) impregnating the reinforcing material with a material glue solution for electronics to obtain a prepreg; heating the prepreg to obtain the electronic material.
Synthesis example
By mass, 120g of 2-allylphenol, 140g of hydrogen and oxygenMixing sodium chloride, 10g of tetrabutylammonium bromide and 230g of tetrahydrofuran, and carrying out heat preservation reaction for 1.5h at the temperature of 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%, according to the reaction formula1H-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 preparation of a Material for electronics
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%.
The resin solution was impregnated with 1080 glass cloth (Shanghai hong and Co.) to obtain a prepreg, which was then dried (160 ℃ C., 40 seconds) to remove the solvent and obtain a prepreg, i.e., an electronic material.
The 8 prepregs were stacked, copper foils (1 oz) were laminated on both sides, and high-temperature thermocompression curing was performed in a press to obtain an electronic material.
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.
And (3) overlapping 8 prepregs, pressing and covering conventional release films on two sides of the prepregs, and performing high-temperature hot-pressing curing in a press to obtain the electronic material. 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 material for comparison electronics, and preparing a comparison copper-clad plate and a comparison insulating material by the same method.
Comparative example No. two
A comparative electronic material 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 comparative copper clad laminate and 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 plate (insulating material process) is prepared, an electronic insulating material is equally divided into four blocks, any two blocks are used for initial bending strength test, the remaining two blocks are dropped by a 5512 impact instrument to the extent that a resin layer has cracks and glass cloth is not damaged, then the two dropped plates are hot-pressed for 5 hours under the conditions that the temperature is 270 ℃ and the pressure is 30MPa, and demoulding is carried out after natural cooling to obtain a secondary cured plate, wherein the appearance of the secondary cured plate has no cracks and is almost the same as the initial one. 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 Performance of examples and comparative examples
Figure BSA0000191736240000051
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 comparative performance tests, and it can be seen that the prepreg prepared by using the polyphenylene ether-coated mesoporous silica and bismaleimide together can ensure the heat resistance and simultaneously show excellent dielectric properties when used for preparing a copper-clad plate.

Claims (7)

1. An electronic material, characterized in that the preparation method of the electronic material 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; adding epoxy chloropropane into a mixed solution of 2-allyl phenol, sodium hydroxide, quaternary ammonium salt and tetrahydrofuran to react to prepare 2-allyl phenyl glycidyl ether;
(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;
(3) impregnating the reinforcing material with a material glue solution for electronics to obtain a prepreg; heating the prepreg to obtain the electronic material;
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.
2. The electronic material according to claim 1, wherein the quaternary ammonium salt is tetramethylammonium bromide and/or tetrabutylammonium 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.
3. The electronic material according to 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 ether is stirred at 130 to 135 ℃ for 50 to 60min, and then mixed with a solvent to obtain the glue solution of the electronic material.
4. The electronic material as claimed in claim 3, wherein the solid content of the electronic material glue is 60-62%; the solvent is a mixture of N, N-dimethylformamide and butanone.
5. The material for electronic use according to claim 1, wherein the heating in the step (3) is carried out at a temperature of 160 ℃ for 40 to 45 seconds.
6. The electronic material as claimed in claim 1, wherein the reinforcing material is a glass cloth.
7. Use of the electronic material according to claim 1 for the preparation of a circuit transmission material.
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Publication number Priority date Publication date Assignee Title
WO1991004284A1 (en) * 1989-09-20 1991-04-04 Hitachi, Ltd. Hexafluorobutadiene prepolymer, production thereof, polymerizable composition, and laminate
CN109021235A (en) * 2016-12-09 2018-12-18 苏州大学 A kind of low dielectric bismaleimide resin system

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991004284A1 (en) * 1989-09-20 1991-04-04 Hitachi, Ltd. Hexafluorobutadiene prepolymer, production thereof, polymerizable composition, and laminate
CN109021235A (en) * 2016-12-09 2018-12-18 苏州大学 A kind of low dielectric bismaleimide resin system

Non-Patent Citations (2)

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Title
Diallyl bisphenol A - Novolac epoxy system cocured with bisphenol-a-bismaleimide - Cure and thermal properties;Ambika Devi等;《 Journal of Applied Polymer Science》;20071231 *
阳离子苯乙烯-马来酰亚胺共聚物应用于造纸湿部的性能研究;左昕;《造纸化学品》;20071215;第19卷(第06期) *

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