CN107286325A - Resin combination and its application - Google Patents
Resin combination and its application Download PDFInfo
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- CN107286325A CN107286325A CN201610202968.1A CN201610202968A CN107286325A CN 107286325 A CN107286325 A CN 107286325A CN 201610202968 A CN201610202968 A CN 201610202968A CN 107286325 A CN107286325 A CN 107286325A
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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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/62—Alcohols or phenols
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- 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
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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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
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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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
- C08G59/245—Di-epoxy compounds carbocyclic aromatic
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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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/3218—Carbocyclic compounds
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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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/38—Epoxy compounds containing three or more epoxy groups together with di-epoxy compounds
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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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4014—Nitrogen containing compounds
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- 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
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
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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
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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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
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
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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
- C09J7/00—Adhesives in the form of films or foils
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- 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
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- 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
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- 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
- B32B2457/00—Electrical equipment
- B32B2457/08—PCBs, i.e. printed circuit boards
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- 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
- C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
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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
- C08L2203/00—Applications
- C08L2203/16—Applications used for films
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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
- C08L2203/00—Applications
- C08L2203/20—Applications use in electrical or conductive gadgets
Abstract
The present invention relates to resin combination and its application.Specifically, the present invention relates to a kind of resin combination, the resin combination contains：The parts by weight of polyfunctional epoxy resin 20~35；The parts by weight of isocyanate modified epoxy resin 8~15；The parts by weight of bifunctional epoxy resin 5~10；The parts by weight of polyphenylene oxide resin 40~65；With the parts by weight of cyanate ester resin 8~16.The invention further relates to the product of the resin combination, including resin film, bonding sheet, prepreg, composite wood, laminated plates and printed circuit board (PCB).By the combination of different resins, the application realizes the superposition of properties of product so that product also has heat-resisting, low-dielectric loss and the resultant effect of easy processing while with good outward appearance.
Description
Technical field
The present invention relates to resin combination and its application.
Background technology
Polyphenylene oxide resin is symmetrical because of molecular structure, and molecular dipole has superior dielectric performance away from low, is engaged in new by vast
Developing material worker is favored.The resin matrix for making curing agent with Noryl has been widely used in composite base material and height
In frequency circuit plate.
The resin combination of prior art is：HMW polybutadiene, the vinyl containing more than 70wt%, weight is equal
Molecular weight MW is more than 100000, accounts for composition weight 0-15wt%；Low molecular weight polybutadiene resin, the second containing more than 70wt%
Alkenyl, weight average molecular weight MW is 1000-10000, accounts for composition weight 10-40wt%；Modified polyphenylene ether resin, weight average molecular weight
For 1000-5000, resin combination 5-35wt% is accounted for.Matrix resin is that unsaturated hydrocarbons is polybutadiene in said composition proportioning,
Network structure is mainly the fat chain structure being made up of carbon-to-carbon, carbon-hydrogen singly-bound after solidification crosslinking, and polarity is small, molecule segment inward turning
Turn easy, and cause clad with metal foil peel strength low, mechanical strength is low.Metal substrate is covered applied to high frequency to easily cause fishing line and fall
Line is bad.It is impregnated with that the prepreg made is inviscid or sticky very little with said composition, is not suitable for being coated with into for curved composite structures
Type.Other said composition each component is larger because of molecular weight, levelling, poor permeability to reinforcing material, the prepreg of impregnation production,
Adhesive sheet outward appearance easily goes out bubble, glue knurl, and then influences the resistance to thermal reliability of base material.
In view of this, develop cover that metal-stripping intensity is high, good moldability can be coated with and the prepreg with good appearance,
Adhesive sheet and composite base material could preferably meet high-frequency circuit use demand.
The content of the invention
It is strong it is an object of the invention to overcome the composite wood for making matrix resin with HMW unsaturated hydrocarbons to cover metal-stripping
Degree is low, and mechanical strength is low, and prepreg is coated with that mouldability is not good and outward appearance has bubble, glue knurl there is provided a kind of high
Metal adhesive strength, high mechanical properties can be coated with good moldability and the resin combination with good appearance is applied to composite wood
Production.
It is a further object to provide above-mentioned resin combination preparing resin film, it is bonding sheet, prepreg, compound
Application in material and laminated plates.
The further object of the present invention is to provide application of the above-mentioned resin combination in high-frequency circuit board is prepared.
The resin combination of the present invention contains：
In one or more embodiments, imidazoles of the resin combination also containing 0.01~0.05 parts by weight promote
Enter agent.
In one or more embodiments, the polyfunctional epoxy resin is selected from：Dicyclopentadiene type polyfunctional group ring
Oxygen tree fat, O-SyL formaldehyde epoxy resin, or its combination.
In one or more embodiments, the dicyclopentadiene type polyfunctional epoxy resin has following structure：
Wherein, n is 1~10 integer.
In one or more embodiments, the O-SyL formaldehyde epoxy resin has following structure：
In various, a, b, c and d each stand alone as 1~10 integer, and each R stands alone as alkyl.
In one or more embodiments, the isocyanate modified epoxy resin is the asphalt mixtures modified by epoxy resin that TDI or MDI is modified
Fat, or its combination.
In one or more embodiments, the isocyanate modified epoxy resin has following structure：
Wherein, R1For epoxy molecule chain, R2For isocyanate molecule chain.
In one or more embodiments, the bifunctional epoxy resin be containing alicyclic ring epoxide resin, it is or de-hydroxylated
The epoxy resin of (the etherified processing of hydroxyl in strand), or its combination.
In one or more embodiments, the bifunctional epoxy resin has following structure：
Wherein, R3For aliphatic chain or aromatic rings.
In one or more embodiments, the number-average molecular weight of the polyphenylene oxide resin is 1000~3000.
In one or more embodiments, the polyphenylene oxide resin is with hydroxy-end capped.
In one or more embodiments, the polyphenylene oxide resin has following structure：
In formula, e, f and g each stand alone as 1~20 integer, and Y is key.
In one or more embodiments, the cyanate ester resin is selected from：The multifunctional cyanogen of bisphenol A cyanate ester, line style
It is more than one or both of acid ester resin, orthoresol type multifunctional cyanate ester resin and dicyclopentadiene phenolic cyanate ester resin
Combination.
In one or more embodiments, the imidazoles accelerator is selected from：2-methylimidazole (2-MI), 2- ethyls-
4-methylimidazole (2E4MI) or 2- phenylimidazoles (2-PI), or its combination.
In one or more embodiments, the resin combination contains：
The dicyclopentadiene type polyfunctional epoxy resin of 20~25 parts by weight；
The epoxy resin that the methyl diphenylene diisocyanate of 8~12 parts by weight is modified；
5~8 parts by weight contain alicyclic ring epoxide resin；
The polyphenylene oxide resin of 40~50 parts by weight；With
The bisphenol A cyanate ester of 8~12 parts by weight.
In one or more embodiments, the resin combination contains：
The O-SyL formaldehyde epoxy resin of 30~35 parts by weight；
The epoxy resin that the methyl diphenylene diisocyanate of 10~15 parts by weight is modified；
7~10 parts by weight contain alicyclic ring epoxide resin；
The polyphenylene oxide resin of 55~65 parts by weight；With
The dicyclopentadiene phenolic cyanate ester resin of 12~16 parts by weight.
Present invention additionally comprises resin film, bonding sheet or the prepreg being made of invention resin composition, using described
Composite wood or laminated plates that resin film or bonding sheet are made, and the printed circuit board (PCB) being made of the laminated plates.
The present invention also provide it is a kind of improve resin film, bonding sheet, prepreg or composite wood cover metal-stripping intensity and/or
The method of mechanical strength, methods described prepares the resin film including the use of resin combination described herein, bonding sheet, pre-
Leaching material or composite wood.
The present invention also provides a kind of method that improvement prepreg is coated with mouldability, and methods described is including the use of herein described
Resin combination prepare the prepreg.
Present invention additionally comprises invention resin composition gold is covered in raising resin film, bonding sheet, prepreg or composite wood
Belong to the application in peel strength and/or mechanical strength, or improve the application that prepreg is coated with mouldability.
Implement resin combination and its application of the present invention, with following beneficial effect：
Embodiment
The resin combination of the present invention uses symmetrical configuration, and the small multiple functionality epoxide resin of molecular dipole moment, solidification is handed over
Join density high, it is ensured that product has high heat resistance.Said composition is changed using the excellent isocyanates of heat resistance, pliability simultaneously
Property epoxy resin, a large amount of N-C=O keys are contained in the resinous molecular structure so that curing substrate, which has, good covers metallicity.Gu
Agent uses symmetrical configuration, and the low polyphenylene oxide resin of polarity and a small amount of cyanate ester resin ensure that product has excellent dielectricity
Energy.Epoxy resin of the compound use containing alicyclic ring or de-hydroxylated difunctionality low molecule amount, reduces resin system viscosity, improves
To the infiltration permeability of enhancing material.By the combination of different resins, the application realizes the superposition of properties of product so that product
Also there is heat-resisting, low-dielectric loss and the resultant effect of easy processing while with good outward appearance.
Specifically, the present invention provides a kind of resin combination, and the resin combination contains polyfunctional epoxy resin, isocyanide
Acid esters modified epoxy, bifunctional epoxy resin, polyphenylene oxide and cyanate ester resin.
In the application, polyfunctional epoxy resin refers to the resin that per molecule on average contains 3 or more than 3 epoxide groups.
Preferably there is symmetrical structure suitable for the polyfunctional epoxy resin of the application, solidification post-crosslinking density is high so that
The resin combination heat resistance of the application is high.Therefore, in certain embodiments, the polyfunctional epoxy resin may be selected from：It is double
Cyclopeutadiene type polyfunctional epoxy resin, O-SyL formaldehyde epoxy resin, or its combination.Preferably symmetrical configuration is multifunctional
Epoxy resin.
As an example, dicyclopentadiene type polyfunctional epoxy resin can have following structure：
Wherein, n is 1~10 integer, such as 1~8,3~10,3~8 integer.
As an example, O-SyL formaldehyde epoxy resin can have following structure：
In various, a, b, c and d each stand alone as 1~10 integer, such as 1~8,3~10,3~8 integer；Each R
Stand alone as alkyl.
In the application, " alkyl " is often referred to saturated hydrocarbyl, and its atomicity is generally in the scope of 1-30, such as 1-20
It is individual, 1-15,1-10,3-10,3-15,3-20,5-10.
Dicyclopentadiene type polyfunctional epoxy resin known in the art and O-SyL formaldehyde epoxy resin can be used
Prepare the resin combination of the application.
Resin combination described herein usually contains the polyfunctional epoxy resin of 20~35 parts by weight.Implement some
In scheme, the content of polyfunctional epoxy resin can such as 20~30 parts by weight, 20~25 parts by weight, 23~35 parts by weight,
Within the scope of 23~30 parts by weight, 25~35 parts by weight, 30~35 parts by weight etc..
Isocyanate modified epoxy resin suitable for the application is usually to have excellent heat resistance and flexible isocyanide
Acid esters modified epoxy.It should be understood that " isocyanate modified epoxy resin " in the application composition with composition
" polyfunctional epoxy resin " and " bifunctional epoxy resin " refer to different epoxy resin." polyfunctional epoxy resin " and
" bifunctional epoxy resin " does not include the epoxy resin of " isocyanate-modified ".
In the application, isocyanate modified epoxy resin generally includes TDI (toluene di-isocyanate(TDI)) or MDI (diphenyl
Methane diisocyanate) modified epoxy resin, or its combination.It is highly preferred that containing N-C=in the molecular structure of the resinoid
O keys, so that curing substrate covers metallicity with good.
Therefore, in certain embodiments, isocyanate modified epoxy resin has following structure：
Wherein, R1For epoxy molecule chain, R2For isocyanate molecule chain.
For example, when the isocyanate modified epoxy resin is TDI (toluene di-isocyanate(TDI)) or MDI (diphenyl methanes
Diisocyanate) modified epoxy resin when, the R2For toluene di-isocyanate(TDI) or point of methyl diphenylene diisocyanate
Subchain.
The present invention can be implemented using isocyanate modified epoxy resin known in the art.Resin group described herein
Compound usually contains the isocyanate modified epoxy resin of 8~15 parts by weight.In certain embodiments, isocyanate-modified ring
The content of oxygen tree fat can be such as 8~12 parts by weight, 8~10 parts by weight, 10~15 parts by weight or 12~15 parts by weight
Within the scope of.
Can be containing alicyclic ring epoxide resin or de-hydroxylated (hydroxyl strand suitable for the bifunctional epoxy resin of the application
The etherified processing of base) epoxy resin, or its combination.It is preferred that, the use of this kind of bifunctional epoxy resin can reduce resinite
It is viscosity, improves the infiltration permeability to enhancing material.
In one or more embodiments, the bifunctional epoxy resin can have following structure：
Wherein, R3For aliphatic chain or aromatic rings.
In the application, aliphatic chain is often referred to the carbochain from aliphatic acid, can be saturation or unsaturation, and its carbon number leads to
Often in the range of 2~30, such as 2~4,6~12,14~24,4~24.Fragrant fourth finger has the planar ring system of conjugation,
Typical aromatic rings includes benzene, naphthalene, pyridine and indoles etc..
Can be using known in the art various containing alicyclic ring epoxide resin or de-hydroxylated (the etherified place of hydroxyl in strand
Reason) epoxy resin prepare the resin combination of the application.Resin combination described herein usually contains 5~10 weight
The isocyanate modified epoxy resin of part.In certain embodiments, the content of isocyanate modified epoxy resin can be in example
Within the scope of such as 5~8 parts by weight, 6~9 parts by weight, 5~7 parts by weight or 7~10 parts by weight.
Number-average molecular weight suitable for the polyphenylene oxide of the present invention is usual in the range of 1000~3000.Preferably, it is described
Polyphenylene oxide is with hydroxy-end capped.In certain embodiments, polyphenylene oxide symmetrical configuration.In other embodiments, polyphenylene oxide has
Relatively low polarity.Polyphenylene oxide resin for the application should cause prepared resin combination product to have excellent dielectricity
Energy.
In one or more embodiments, the application uses the polyphenylene oxide resin with following structure：
In formula, e, f and g each stand alone as 1~20 integer, such as 1~15,1~10,3~15,3~10,5~15
Integer；Y is key.
In certain embodiments, f=g.
Known polyphenylene oxide resin can be used to prepare the resin combination of the present invention.Resin combination described herein
Usually contain the polyphenylene oxide resin of 40~65 parts by weight.In certain embodiments, the content of polyphenylene oxide resin can be for example
40~60 parts by weight, 45~60 parts by weight, 45~65 parts by weight, 40~50 parts by weight, 40~55 parts by weight or 50~65 weight
Within the scope of part is waited.
Cyanate ester resin suitable for the present invention can be various cyanate ester resins well known in the art, such as bisphenol A-type
Cyanate, line style multifunctional cyanate ester resin, orthoresol type multifunctional cyanate ester resin and dicyclopentadiene phenolic cyanate resin
Combination more than one or both of fat.Preferably, the use of this kind of cyanate ester resin, coordinates polyphenylene oxide resin so that
Preparation-obtained resin combination has required dielectric properties.
Resin combination described herein usually contains the cyanate ester resin of 8~16 parts by weight.In some embodiments
In, the content of cyanate ester resin can be in such as 8~12 parts by weight, 8~10 parts by weight, 10~16 parts by weight, 10~13 weight
Within the scope of part or 12~16 parts by weight etc..
For different purposes, also it can routinely be added in the resin combination of the application containing this area in resin combination
Other additives, including but not limited to described resin combination also contains hardening accelerator, fire retardant, inorganic filler, solvent
At least one of with surfactant.
Hardening accelerator can be the various hardening accelerators standby for resin-made well known in the art, especially may include miaow
Azole accelerator, such as 2-methylimidazole (2-MI), 2-ethyl-4-methylimidazole (2E4MI), 2- phenylimidazoles (2-PI), or
It is combined.
Generally, resin combination of the invention can the hardening accelerator containing 0.01~0.05 parts by weight.
Fire retardant can be the compound with anti-flammability element or anti-flammability functional group well known in the art, can be phosphorous
Compound, nitrogen-containing compound or bromine-containing compound, such as bis-phenol diphenyl phosphoester, APP, hydroquinones-bis--(hexichol
Base phosphate), bisphenol-A-bis--(diphenyl phosphoester) etc..
The consumption of fire retardant can be its conventional consumption in resin combination, and those skilled in the art can be according to conventional skill
Art means are readily determined.Generally, the consumption of fire retardant can be 0.5 to 30 parts by weight in invention resin composition.
Inorganic filler can be the various inorganic fillers that this area is routinely used in resin combination, including but not
Be limited to silica (molten state, non-melt state, many empty matter or hollow type), aluminum oxide, aluminium hydroxide, magnesia, magnesium hydroxide,
Calcium carbonate, aluminium nitride, boron nitride, aluminum silicon carbide, carborundum, titanium dioxide, zinc oxide, zirconium oxide, mica, boehmite, calcining
Talcum, talcum, silicon nitride, calcined kaolin or its combination.
The consumption of inorganic filler can be readily determined according to the practical use of resin combination.Generally, resin of the present invention
The consumption of inorganic filler can be between 10~100 parts by weight in composition, such as 30~80 parts by weight.
Solvent can be the various solvents for resin combination well known in the art, including but not limited to methanol, ethanol,
Glycol monoethyl ether, acetone, butanone (also known as methyl ethyl ketone), methyl iso-butyl ketone (MIBK), cyclohexanone, toluene, dimethylbenzene, methoxy
Base ethylhexoate, ethoxyethyl acetate, Among acetic acid esters, ethyl acetate, dimethylformamide, propane diols first
Base ether equal solvent or its mixed solvent.
Amount to organic solvent is not limited, generally, and 100~300 parts by weight can be used in the resin combination of every 100 parts by weight
Organic solvent, such as 100~220 parts by weight.Preferably, the amount of the organic solvent used causes consolidating for the resin solution of gained
Content is within the scope of 50~65% (mass percents).
Surfactant can be the various surfactants for resin well known in the art, including but not limited to silane
Compound or silicone compounds.The consumption of surfactant can be 0.1 parts by weight to 10 weights in invention resin composition
Measure part.
The resin combination of the application can be used for preparing resin film, bonding sheet, prepreg, laminated plates or printed circuit board (PCB)
Deng.
For example, it can be made to solidify to form resin film the resin combination Baking out of the application.
Or, each composition of resin combination can be mixed according to its consumption proportion, be added in organic solvent and be configured to
Solid content is the resin solution of 50~65% (mass percents).Then the resin combination is attached to benefit the mode such as to be impregnated with
On strong material, and via high-temperature heating (such as 80~180 DEG C) formation semi-solid preparation state, so as to obtain bonding sheet or the preimpregnation of the application
Material.In other words, the bonding sheet or prepreg of the application generally has the resin combination of reinforcing material and the present invention.
In certain embodiments, the high-temperature heating treatment includes：80~85 DEG C/2~3 minutes, 130~135 DEG C/3~4
Minute and subsequent 175~180 DEG C/5~6 minutes.
Reinforcing material can be fibrous material, weave cotton cloth and adhesive-bonded fabric, such as glass fabric, strong with the machinery for increasing the bonding sheet
Degree.
Further, can be using the bonding sheet of the semi-solid preparation or resin film (being used as the insulating barrier in laminated plates), by setting
Number stack, two-sided or one side mixes metal foil, and metal foil need not be matched somebody with somebody during composite wood, laminated plates are pressed at high temperature under high pressure
Or composite wood.The material of metal foil can be copper, aluminium, nickel, platinum, silver, gold or its alloy.High temperature is usually 180~240 DEG C, high pressure
Usually 200~450psi.Therefore, when copper is being used, the laminated plates are copper-clad plate.Laminated plates can also be further via circuit
Printed circuit board (PCB), especially high-frequency circuit board is made after processing procedure processing.
Therefore, the application includes resin finished product, and the resin finished product includes resin film, bonding sheet, prepreg, laminated plates or print
Printed circuit board, especially high-frequency circuit board, are prepared using the resin combination of the application.
Compared with prior art, the present invention has the advantages that：
1st, the present invention contains a large amount of aromatic rings due to having used in the symmetrical polyfunctional epoxy resin of structure, strand, Gu
Change crosslink density high so that solidfied material has good heat resistance and mechanical strength.
2nd, the isocyanate-modified epoxy that the present invention is used, due to rigidly being tied containing a large amount of five-ring heterocycles in molecular backbone
Structure, product has excellent heat resistance and toughness.Contain a large amount of N-C=O keys in the molecular structure simultaneously so that curing substrate has
Good covers metallicity
3rd, it is of the invention because curing agent uses symmetrical configuration, low polarity, the polyphenylene oxide of low molecule amount so that composition component
Between intermiscibility it is good, in the absence of problem of phase separation, it is ensured that product has excellent, homogeneous dielectric properties.
4th, molecular weight is low, viscosity is low, symmetrical configuration containing alicyclic ring or de-hydroxylated low point due to having used simultaneously by the present invention
Son amount bifunctional epoxy resin causes product to have the comprehensive advantage of low-dielectric loss and good appearance.
5th, simple production process of the present invention, has a extensive future in bonding sheet, prepreg, composite wood and circuit substrate.
Obtained composite wood or circuit substrate have that high heat-resisting and dielectric loss is low, are suitable as high-frequency circuit substrate.
Hereafter the present invention will be described in the way of specific embodiment.It should be understood that these embodiments are only illustrative, and
Unrestricted protection scope of the present invention.Method, reagent and condition employed in embodiment, unless otherwise stated, being this
Field conventional method, reagent and condition.
Moreover, it will be understood that unless otherwise indicated, comparatively the parts by weight for each component being related in the application are
, i.e., described resin combination contain the polyfunctional epoxy resin of 20~35 parts by weight, 8~15 parts by weight it is isocyanate-modified
Epoxy resin, the bifunctional epoxy resin of 5~10 parts by weight, the polyphenylene oxide resin of 40~65 parts by weight and 8~16 parts by weight
Cyanate ester resin, it is intended that the polyfunctional epoxy resin of every 20~35 parts by weight uses the isocyanate-modified ring of 8~15 parts by weight
Oxygen tree fat, the bifunctional epoxy resin of 5~10 parts by weight, the cyanogen of the polyphenylene oxide resin of 40~65 parts by weight and 8~16 parts by weight
Acid ester resin.
Embodiment 1
Weigh the dicyclopentadiene type polyfunctional epoxy resin, 8 parts by weight MDI modified epoxies, 5 weight of 20 parts by weight
Part contains alicyclic ring epoxide resin, 40 parts by weight of polyphenyleneoxide, 8 parts by weight of bisphenol A types cyanates and 0.01 parts by weight 2-methylimidazole (2-
MI), it is added to the resin solution for being made into that solid content is 60% in 122 parts by weight butanone.
Immersed in above-mentioned resin solution, be impregnated with 8 (200mm*200mm) 7628 quartz fabrics.By 80 DEG C/2 minutes+
Bakee in an oven within+175 DEG C/5 minutes 130 DEG C/3 minutes, the bonding sheet of semi-cured state is made.
Above-mentioned 8 bonding sheets are superimposed and alignd, up and down the copper foil respectively with 1 35um.In vacuum press, by temperature 210
DEG C, pressure 25kgf/cm2Condition, suppress 160 minutes, be made thickness be 1.6mm double face copper.
Embodiment 2
Weigh 35 parts by weight O-SyL aldehyde type polyfunctional epoxy resins, 15 parts by weight MDI modified epoxies, 10 weight
Part contains alicyclic ring epoxide resin, 65 parts by weight of polyphenyleneoxide, 16 parts by weight dicyclopentadiene phenolic cyanate ester resins and 0.05 parts by weight
2-methylimidazole (2-MI), be added to be made into 212 parts by weight butanone solid content be 60% resin solution.
Immersed in above-mentioned resin solution, be impregnated with 8 (200mm*200mm) 7628 quartz fabrics.By 80 DEG C/2 minutes+
Bakee in an oven within+175 DEG C/5 minutes 130 DEG C/3 minutes, the bonding sheet of semi-cured state is made.
Above-mentioned 8 bonding sheets are superimposed and alignd, up and down the copper foil respectively with 1 35um.In vacuum press, by temperature 210
DEG C, pressure 25kgf/cm2Condition, suppress 160 minutes, be made thickness be 1.6mm double face copper.
Comparative example
Weigh 20 parts by weight HMW polybutadienes, 35 parts by weight low molecular weight polybutadiene resins, 45 weight
The polyphenylene oxide resin of part adds q. s. toluene mixing, adds 11 parts of parts by weight TAIC crosslinking agents, 6 parts by weight DCP initiators, normal temperature
Under be stirred until homogeneous.
Immersed in above-mentioned resin solution, bakeed 6 minutes with 110 DEG C with 8 (200mm*200mm) 7628 quartz fabrics.It is made
The bonding sheet of semi-cured state.
Other conditions are same as Example 1, and the double face copper that thickness is 1.6mm is made.
Test case
Comparative example is compared with Examples 1 and 2 using existing process conditions, as a result such as table 1：
Table 1
It can be seen that, using the prepreg and composite wood made by the resin combination of the present invention not only have it is good it is heat-resisting,
Mechanical strength, metal adhesive strength and dielectric properties, and the prepreg that makes of impregnation has good outward appearance and suitable
It is coated with shaping viscosity.
Claims (24)
1. a kind of resin combination, it is characterised in that the resin combination contains：
2. resin combination as claimed in claim 1, it is characterised in that the polyfunctional epoxy resin is selected from：Bicyclic penta 2
Ene-type polyfunctional epoxy resin, O-SyL formaldehyde epoxy resin or its combination.
3. resin combination as claimed in claim 2, it is characterised in that the dicyclopentadiene type polyfunctional epoxy resin
With following structure：
In formula, n is 1~10 integer.
4. resin combination as claimed in claim 2, it is characterised in that the O-SyL formaldehyde epoxy resin has following knot
Structure：
In various, a, b, c and d are respectively 1~10 integer, and each R stands alone as alkyl.
5. resin combination as claimed in claim 1, it is characterised in that the isocyanate modified epoxy resin is toluene two
Isocyanate-modified epoxy resin, the epoxy resin of methyl diphenylene diisocyanate modification or its combination, and the isocyanide
Acid esters modified epoxy contains N-C=O keys.
6. resin combination as claimed in claim 5, it is characterised in that the isocyanate modified epoxy resin has following
Structure：
Wherein, R1For epoxy molecule chain, R2For isocyanate molecule chain.
7. resin combination as claimed in claim 1, it is characterised in that the bifunctional epoxy resin is tree containing alicyclic epoxy
The de-hydroxylated epoxy resin of the etherified processing of hydroxyl in fat, or strand, or its combination.
8. resin combination as claimed in claim 7, it is characterised in that the bifunctional epoxy resin has following structure：
Wherein, R3For aliphatic chain or aromatic rings.
9. resin combination as claimed in claim 1, it is characterised in that the number-average molecular weight of the polyphenylene oxide resin is 1000
~3000.
10. resin combination as claimed in claim 9, it is characterised in that the polyphenylene oxide resin is with hydroxy-end capped.
11. resin combination as claimed in claim 10, it is characterised in that the polyphenylene oxide resin has following structure：
In formula, e, f and g each stand alone as 1~20 integer, and Y is key.
12. resin combination as claimed in claim 1, it is characterised in that the cyanate ester resin is selected from：Bisphenol A-type cyanic acid
In ester, line style multifunctional cyanate ester resin, orthoresol type multifunctional cyanate ester resin and dicyclopentadiene phenolic cyanate ester resin
One or more kinds of combinations.
13. resin combination as claimed in claim 12, it is characterised in that the cyanate ester resin is selected from：Bisphenol A-type cyanic acid
Ester, dicyclopentadiene phenolic cyanate ester resin or its combination.
14. resin combination as claimed in claim 1, it is characterised in that
The polyfunctional epoxy resin is selected from：Dicyclopentadiene type polyfunctional epoxy resin, O-SyL formaldehyde epoxy resin or
It is combined；Wherein, the dicyclopentadiene type polyfunctional epoxy resin has following structure：
In formula, n is 1~10 integer；
The O-SyL formaldehyde epoxy resin has following structure：
In various, a, b, c and d are respectively 1~10 integer, and each R stands alone as alkyl；
The isocyanate modified epoxy resin is the epoxy resin or the isocyanide of diphenyl methane two that toluene di-isocyanate(TDI) is modified
The epoxy resin that acid esters is modified, and with following structure：
Wherein, R1For epoxy molecule chain, R2For isocyanate molecule chain；
The bifunctional epoxy resin is the de-hydroxylated epoxy containing the etherified processing of hydroxyl in alicyclic ring epoxide resin or strand
Resin, it is described that there is following structure containing alicyclic ring epoxide resin：
The de-hydroxylated epoxy resin of the etherified processing of hydroxyl has following structure in the strand：
Wherein, R3For aliphatic chain or aromatic rings；
The polyphenylene oxide resin has following structure：
In formula, e, f and g each stand alone as 1~20 integer, and Y is key；With
The cyanate ester resin is selected from：Bisphenol A cyanate ester, dicyclopentadiene phenolic cyanate ester resin or its combination.
15. resin combination as claimed in claim 14, it is characterised in that the resin combination contains：
The dicyclopentadiene type polyfunctional epoxy resin of 20~25 parts by weight；
The epoxy resin that the methyl diphenylene diisocyanate of 8~12 parts by weight is modified；
5~8 parts by weight contain alicyclic ring epoxide resin；
The polyphenylene oxide resin of 40~50 parts by weight；With
The bisphenol A cyanate ester of 8~12 parts by weight.
16. resin combination as claimed in claim 14, it is characterised in that the resin combination contains：
The O-SyL formaldehyde epoxy resin of 30~35 parts by weight；
The epoxy resin that the methyl diphenylene diisocyanate of 10~15 parts by weight is modified；
7~10 parts by weight contain alicyclic ring epoxide resin；
The polyphenylene oxide resin of 55~65 parts by weight；With
The dicyclopentadiene phenolic cyanate ester resin of 12~16 parts by weight.
17. the resin combination as any one of claim 1-16, it is characterised in that the resin combination also contains
There are at least one of hardening accelerator, fire retardant, inorganic filler, solvent and surfactant.
18. resin combination as claimed in claim 17, it is characterised in that the resin combination contains 0.01~0.05 weight
Measure the hardening accelerator of part.
19. resin combination as claimed in claim 18, it is characterised in that the hardening accelerator is imidazoles accelerator,
Selected from 2-methylimidazole, 2-ethyl-4-methylimidazole, 2- phenylimidazoles, or its combination.
20. resin combination as claimed in claim 17, it is characterised in that the resin combination contains solvent, with quality
Percentage meter, the solid content of the resin combination is within the scope of 50~65%.
21. a kind of resin film, bonding sheet or prepreg, it is characterised in that the resin film, bonding sheet or prepreg use right
It is required that the resin combination any one of 1-20 is made.
22. a kind of composite wood or laminated plates, it is characterised in that the composite wood or laminated plates are using the tree described in claim 21
Adipose membrane or bonding sheet are made.
23. a kind of printed circuit board (PCB), it is characterised in that the printed circuit board (PCB) is using the laminated plates system described in claim 22
Into.
24. the resin combination any one of claim 1-20 is improving resin film, bonding sheet, prepreg or compound
The application covered in metal-stripping intensity and/or mechanical strength of material, or improving the application that prepreg is coated with mouldability.
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| CN109135652A (en) * | 2018-08-09 | 2019-01-04 | 陕西生益科技有限公司 | A kind of high thermal conductivity toughened resin composition and its application |
| CN109181234A (en) * | 2018-08-09 | 2019-01-11 | 陕西生益科技有限公司 | A kind of high thermal conductivity high tenacity resin combination and its application |
| WO2019127992A1 (en) * | 2017-12-29 | 2019-07-04 | 洛阳尖端技术研究院 | Prepreg, composite material, and preparation methods therefor and uses thereof |
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| CN111100423A (en) * | 2019-12-27 | 2020-05-05 | 惠柏新材料科技（上海）股份有限公司 | Single-liquid epoxy resin composition and fiber-reinforced composite material |
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