CN112574670A - Epoxy-terminated branched polysiloxane modified cyanate resin - Google Patents
Epoxy-terminated branched polysiloxane modified cyanate resin Download PDFInfo
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- CN112574670A CN112574670A CN202011425623.5A CN202011425623A CN112574670A CN 112574670 A CN112574670 A CN 112574670A CN 202011425623 A CN202011425623 A CN 202011425623A CN 112574670 A CN112574670 A CN 112574670A
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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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D187/00—Coating compositions based on unspecified macromolecular compounds, obtained otherwise than by polymerisation reactions only involving unsaturated carbon-to-carbon bonds
- C09D187/005—Block or graft polymers not provided for in groups C09D101/00 - C09D185/04
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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
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
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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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/61—Additives non-macromolecular 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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/70—Additives characterised by shape, e.g. fibres, flakes or microspheres
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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
- C09J11/04—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
- C09J187/00—Adhesives based on unspecified macromolecular compounds, obtained otherwise than by polymerisation reactions only involving unsaturated carbon-to-carbon bonds
- C09J187/005—Block or graft polymers not provided for in groups C09J101/00 - C09J185/04
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K2201/00—Specific properties of additives
- C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
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- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
Abstract
The invention provides epoxy-terminated branched polysiloxane modified cyanate ester resin, and relates to the field of preparation and application of modified cyanate ester resin with atomic oxygen etching resistance, ultraviolet aging resistance, high and low temperature resistance and low dielectric loss. The epoxy-terminated branched polysiloxane modified cyanate ester resin comprises the following components in parts by weight: 100 parts of cyanate ester resin, 10-50 parts of epoxy resin, 5-25 parts of epoxy terminated phenyl polysiloxane, 0-20 parts of inorganic filler and 0.1-1 part of curing accelerator. The coating obtained by the invention has low viscosity at 70-90 ℃, is suitable for hot-melt coating to prepare prepreg, and has the dielectric constant epsilon of less than or equal to 3.0 and the dielectric loss tangent of less than or equal to 0.015 after curing, so that the toughness of a cured product is improved; the high and low temperature resistance is good, and the atomic oxygen etching resistance and the ultraviolet aging resistance are excellent; the epoxy resin can be used as a special high-performance resin for a composite material with high and low temperature resistance, high wave transmission and ultraviolet resistance, an adhesive for a high-frequency laminated circuit board and a space-level atomic oxygen structure-resistant adhesive.
Description
Technical Field
The invention relates to a preparation method and application field of modified cyanate ester resin with atomic oxygen etching resistance, ultraviolet aging resistance, high and low temperature resistance and low dielectric loss, in particular to epoxy terminated branched polysiloxane modified cyanate ester resin.
Background
The resin and the coating with low dielectric constant and low dielectric loss are widely applied to the fields of high-frequency printed circuit boards, electromagnetic windows, high-wave-transparent antenna covers and the like. The problem that the existing high-frequency printed circuit board, electromagnetic window and high-wave-transparent antenna housing generate heat higher in the using process is always puzzled by people, and the research and development of materials with low dielectric constant and low dielectric loss are ways for solving the problem that a circuit generates heat and reducing the capacitance effect between wires.
Disclosure of Invention
Technical problem to be solved
Aiming at the defects of the prior art, the invention provides epoxy-terminated branched polysiloxane modified cyanate ester resin, which solves the problem that the prior high-frequency printed circuit board, electromagnetic window and high-wave-transparent antenna cover have higher heat productivity in the use process.
(II) technical scheme
In order to achieve the purpose, the invention is realized by the following technical scheme: an epoxy terminated branched polysiloxane modified cyanate ester resin comprises the following components in parts by weight: 100 parts of cyanate ester resin, 10-50 parts of epoxy resin, 5-25 parts of epoxy terminated phenyl polysiloxane, 0-20 parts of inorganic filler and 0.1-1 part of curing accelerator.
Preferably, the epoxy resin is low-molecular-weight epoxy organic silicon resin, the molecular weight of the molecular structure is 385-10000, the epoxy value is 30-50, and the epoxy resin is one of E51, E44 bisphenol A epoxy resin, F-48 and F-51 phenolic epoxy resin.
Preferably, the cyanate ester resin is bisphenol A type cyanate ester resin, phenolic aldehyde type epoxy resin and prepolymer thereof.
Preferably, the epoxy-terminated branched polysiloxane modified cyanate ester resin contains a catalyst, and the catalyst is one of bisphenol a, phenolic resin, zinc acetylacetonate and stannous octoate.
Preferably, the inorganic filler is black ceramic powder, and the black ceramic powder comprises silicon carbide and silicon carbonitride.
Preferably, the curing accelerator is a thickening agent and a wetting leveling agent, the thickening agent is one of gas phase and precipitated white carbon black, and the wetting leveling agent is polyether modified polysiloxane.
A preparation method of epoxy terminated branched polysiloxane modified cyanate ester resin comprises the following steps:
adding a catalyst into the epoxy resin and the cyanate ester resin, carrying out prepolymerization for a period of time at a certain temperature, adding the black ceramic powder, a certain amount of thickening agent and a certain amount of wetting and leveling agent into a prepolymerization product, then adding a solvent, mixing and stirring uniformly;
the molecular weight of the prepolymerization product is 1000-100000, and the weight ratio of the epoxy resin to the cyanate ester resin is 1-10: 10, the concentration of the catalyst is 10-1000 ppm, the temperature of the prepolymerization is 80-150 ℃, and the time of the prepolymerization is 1-10 h.
Preferably, the solvent comprises at least one of butanone, toluene, mixed xylene, ethylene glycol monobutyl ether, and butyl acetate.
(III) advantageous effects
The invention provides epoxy-terminated branched polysiloxane modified cyanate ester resin. The method has the following beneficial effects:
the invention has lower viscosity at 70-90 ℃, is suitable for hot-melt coating to prepare prepreg, has the dielectric constant epsilon of less than or equal to 3.0 after curing, has the dielectric loss tangent value of less than or equal to 0.015, and improves the toughness of a cured product; the high and low temperature resistance is good, and the atomic oxygen etching resistance and the ultraviolet aging resistance are excellent; the epoxy resin can be used as a special high-performance resin for a composite material with high and low temperature resistance, high wave transmission and ultraviolet resistance, an adhesive for a high-frequency laminated circuit board and a space-level atomic oxygen structure-resistant adhesive.
Drawings
FIG. 1 is a magnetic resonance spectrum of the present invention;
FIG. 2 is an FTIR spectrum of the present invention.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The first embodiment is as follows:
as shown in fig. 1-2, an embodiment of the present invention provides an epoxy-terminated branched polysiloxane modified cyanate ester resin, which is prepared by introducing nitrogen into 10 parts of bisphenol a type E51 epoxy resin, 100 parts of cyanate ester resin, and 0.1 part of catalyst bisphenol a at 80 ℃, stirring and prepolymerizing for 10 hours, wherein the concentration of the catalyst is 100ppm, so as to obtain a paste-like light yellow epoxy modified cyanate ester prepolymer, and having an average molecular weight of 1000, then adding 10 parts of black ceramic filler, 0.1 part of thickener fumed silica, 0.05 part of wetting agent, and 110 parts of solvent butanone, mixing and stirring uniformly, so as to obtain a low dielectric loss coating, wherein the viscosity is 1500mpa.s, the curing temperature is 150 ℃, the dielectric constant epsilon of a paint film after 2 hours of curing is 3.0, and the dielectric loss tangent tan delta is 0.009.
Example two:
as shown in fig. 1-2, an embodiment of the present invention provides an epoxy-terminated branched polysiloxane modified cyanate ester resin, which is prepared by introducing nitrogen into 20 parts of bisphenol a type E44 epoxy resin, 100 parts of cyanate ester resin, 0.1 part of stannous octoate as a catalyst at 85 ℃, stirring and prepolymerizing for 8 hours, wherein the concentration of the catalyst is 250ppm, to obtain a viscous lemon yellow epoxy modified cyanate ester prepolymer, and the average molecular weight is 3500, then adding 15 parts of black ceramic filler, 0.25 part of thickener precipitated white carbon black, 0.1 part of wetting and leveling agent, and 150g of ethylene glycol monobutyl ether as a solvent, mixing and stirring uniformly, to obtain a low dielectric loss coating material, wherein the viscosity is 1350mpa.s, the curing temperature is 150 ℃, the dielectric constant epsilon of a paint film after 2.5 hours curing is 2.8, and the dielectric loss tangent tan delta is 0.012.
Example three:
as shown in fig. 1-2, an embodiment of the present invention provides an epoxy-terminated branched polysiloxane modified cyanate ester resin, which is prepared by introducing nitrogen into 30 parts of phenolic F-48 epoxy resin, 100 parts of cyanate ester resin, 0.15 part of zinc acetylacetonate as a catalyst at 75 ℃, stirring and prepolymerizing for 8 hours, wherein the concentration of the catalyst is 500ppm, to obtain a colloidal brown-yellow epoxy modified cyanate ester prepolymer, and having an average molecular weight of 10000, then adding an equal amount of a mixture of 20 parts of a black ceramic filler, 0.3 part of a thickener fumed silica, 0.15 part of a wetting and leveling agent, and 200 parts of a solvent, namely toluene and mixed xylene, mixing and stirring uniformly, to obtain a low dielectric loss coating material, wherein the viscosity is 1400mpa.s, the curing temperature is 150 ℃, the dielectric constant epsilon of a paint film after 3 hours of curing is 2.9, and the dielectric loss tangent tan delta is 0.015.
Example four:
as shown in fig. 1-2, an embodiment of the present invention provides an epoxy-terminated branched polysiloxane modified cyanate ester resin, which is prepared by introducing nitrogen into 45 parts of phenolic F-51 epoxy resin, 100 parts of cyanate ester resin, and 0.15 part of catalyst bisphenol a at 135 ℃, stirring and prepolymerizing for 10 hours, wherein the concentration of the catalyst is 580ppm, to obtain a viscous brown yellow epoxy modified cyanate ester prepolymer, and having an average molecular weight of 15800, then adding 20 parts of black ceramic filler, 0.6 part of thickener precipitated white carbon black, 0.25 part of wetting and leveling agent, and 350 parts of an equal mixture of solvent butanone, toluene, and butyl acetate, mixing and stirring uniformly, to obtain a low dielectric loss coating material, having a viscosity of 1460mpa.s, a curing temperature of 150 ℃, a dielectric constant e of a paint film after 3.5 hours of curing being 2.7, and a dielectric loss tangent tan δ being 0.009.
The coating can be well dissolved in a solvent, the solid content of the coating is 20-60%, the coating can be sprayed, rolled and the like, and the coating with the solid content of 100% can also be melted into liquid at 80-100 ℃, and the liquid is directly sprayed or rolled on the surface of a base material.
Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that changes, modifications, substitutions and alterations can be made in these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (8)
1. An epoxy-terminated branched polysiloxane modified cyanate ester resin, which is characterized in that: the composition comprises the following components in parts by weight: 100 parts of cyanate ester resin, 10-50 parts of epoxy resin, 5-25 parts of epoxy terminated phenyl polysiloxane, 0-20 parts of inorganic filler and 0.1-1 part of curing accelerator.
2. The epoxy-terminated branched polysiloxane modified cyanate ester resin according to claim 1, wherein: the epoxy resin is low-molecular-weight epoxy organic silicon resin, the molecular weight of the molecular structure of the epoxy resin is 385-10000, the epoxy value is 30-50, and the epoxy resin is one of E51, E44 bisphenol A epoxy resin, F-48 and F-51 phenolic epoxy resin.
3. The epoxy-terminated branched polysiloxane modified cyanate ester resin according to claim 1, wherein: the cyanate resin is bisphenol A type cyanate resin, phenolic aldehyde type epoxy resin and prepolymer thereof.
4. The epoxy-terminated branched polysiloxane modified cyanate ester resin according to claim 1, wherein: the epoxy-terminated branched polysiloxane modified cyanate ester resin contains a catalyst, and the catalyst is one of bisphenol A, phenolic resin, zinc acetylacetonate and stannous octoate.
5. The epoxy-terminated branched polysiloxane modified cyanate ester resin according to claim 1, wherein: the inorganic filler is black ceramic powder, and the black ceramic powder comprises silicon carbide and silicon carbonitride.
6. The epoxy-terminated branched polysiloxane modified cyanate ester resin according to claim 1, wherein: the curing accelerator is a thickening agent and a wetting leveling agent, the thickening agent is one of gas phase and precipitated white carbon black, and the wetting leveling agent is polyether modified polysiloxane.
7. A preparation method of epoxy terminated branched polysiloxane modified cyanate ester resin is characterized by comprising the following steps: the preparation process comprises the following steps:
adding a catalyst into the epoxy resin and the cyanate ester resin, carrying out prepolymerization for a period of time at a certain temperature, adding the black ceramic powder, a certain amount of thickening agent and a certain amount of wetting and leveling agent into a prepolymerization product, then adding a solvent, mixing and stirring uniformly;
the molecular weight of the prepolymerization product is 1000-100000, and the weight ratio of the cyanate ester resin to the epoxy resin is 1-10: 10, the concentration of the catalyst is 10-1000 ppm, the temperature of the prepolymerization is 80-150 ℃, and the time of the prepolymerization is 1-10 h.
8. The method for preparing epoxy terminated branched polysiloxane modified cyanate ester resin according to claim 7, wherein: the solvent comprises at least one of butanone, toluene, mixed xylene, ethylene glycol monobutyl ether and butyl acetate.
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| CN202011425623.5A CN112574670A (en) | 2020-12-07 | 2020-12-07 | Epoxy-terminated branched polysiloxane modified cyanate resin |
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| CN202011425623.5A CN112574670A (en) | 2020-12-07 | 2020-12-07 | Epoxy-terminated branched polysiloxane modified cyanate resin |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113278357A (en) * | 2021-05-21 | 2021-08-20 | 广东腐蚀科学与技术创新研究院 | Graphene oxide nanosheet modified oxazine ring structure temperature-resistant corrosion-resistant inert coating and preparation method thereof |
Citations (5)
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| US20120018072A1 (en) * | 2009-03-27 | 2012-01-26 | Mitsubishi Gas Chemical Company, Inc. | Method for storing resin solution, and method for producing prepreg and laminate |
| CN102676112A (en) * | 2012-06-08 | 2012-09-19 | 黑龙江省科学院石油化学研究院 | Low-temperature curing cyanate ester adhesive and preparation method thereof |
| CN105219255A (en) * | 2015-11-11 | 2016-01-06 | 江苏和成新材料有限公司 | A kind of low-dielectric loss black matt coating and preparation method thereof and application |
| US20180334567A1 (en) * | 2017-05-19 | 2018-11-22 | Shin-Etsu Chemical Co., Ltd. | Silicone-modified epoxy resin composition and semiconductor device |
| CN109943071A (en) * | 2019-03-29 | 2019-06-28 | 中南大学 | A kind of polysiloxane-modified cyanate resin base shape-memory material and preparation method thereof with high glass-transition temperature |
-
2020
- 2020-12-07 CN CN202011425623.5A patent/CN112574670A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20120018072A1 (en) * | 2009-03-27 | 2012-01-26 | Mitsubishi Gas Chemical Company, Inc. | Method for storing resin solution, and method for producing prepreg and laminate |
| CN102676112A (en) * | 2012-06-08 | 2012-09-19 | 黑龙江省科学院石油化学研究院 | Low-temperature curing cyanate ester adhesive and preparation method thereof |
| CN105219255A (en) * | 2015-11-11 | 2016-01-06 | 江苏和成新材料有限公司 | A kind of low-dielectric loss black matt coating and preparation method thereof and application |
| US20180334567A1 (en) * | 2017-05-19 | 2018-11-22 | Shin-Etsu Chemical Co., Ltd. | Silicone-modified epoxy resin composition and semiconductor device |
| CN109943071A (en) * | 2019-03-29 | 2019-06-28 | 中南大学 | A kind of polysiloxane-modified cyanate resin base shape-memory material and preparation method thereof with high glass-transition temperature |
Non-Patent Citations (3)
| Title |
|---|
| SHANKAI DAI等: "Preparation and properties of cyanate ester/polyorganosiloxane blends with lower dielectric loss and improved toughness", 《POLYMERS ADVANCED TECHNOLOGIES》 * |
| 李子东: "《实用粘结手册》", 31 March 1988, 上海科学技术文献出版社 * |
| 李琼瑶等: "《交通事故物证勘查和检验（第二版）》", 30 September 2003, 中国人民公安大学出版社 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113278357A (en) * | 2021-05-21 | 2021-08-20 | 广东腐蚀科学与技术创新研究院 | Graphene oxide nanosheet modified oxazine ring structure temperature-resistant corrosion-resistant inert coating and preparation method thereof |
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Application publication date: 20210330 |