CN104212167B - A kind of preparation and its application of low cost low-k thermosetting resin - Google Patents
A kind of preparation and its application of low cost low-k thermosetting resin Download PDFInfo
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- CN104212167B CN104212167B CN201410445263.3A CN201410445263A CN104212167B CN 104212167 B CN104212167 B CN 104212167B CN 201410445263 A CN201410445263 A CN 201410445263A CN 104212167 B CN104212167 B CN 104212167B
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- resin
- cyanate
- epoxy resin
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- phenolic resin
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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
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
- C08L61/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
-
- 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
- B32B19/00—Layered products comprising a layer of natural mineral fibres or particles, e.g. asbestos, mica
- B32B19/02—Layered products comprising a layer of natural mineral fibres or particles, e.g. asbestos, mica the layer of fibres or particles being impregnated or embedded in a plastic substance
-
- 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
- B32B27/00—Layered products comprising a layer of 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
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/38—Layered products comprising a layer of synthetic resin comprising epoxy resins
-
- 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
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/42—Layered products comprising a layer of synthetic resin comprising condensation resins of aldehydes, e.g. with phenols, ureas or melamines
-
- 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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- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions 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 C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
-
- 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
- C08L2203/20—Applications use in electrical or conductive gadgets
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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 present invention relates to method and the applications of a kind of synthesis of the novel phenolic resins containing phenylate structure (thermoplasticity and thermosetting property) and its modified heat convertible resin.The resin is obtained by 2 kinds in cyanate, epoxy resin, the phenolic resin containing phenylate structure or 3 kinds by co-curing behavior.The group of the resin raw material becomes in cyanate, epoxy resin, the phenolic resin containing phenylate structure 2 kinds or 3 kinds, and the mass percent of component is：Cyanate：10 ~ 99%, epoxy resin：0% ~ 100%, novel phenolic resins：10~100%.The thermosetting resin of the present invention has excellent dielectric properties and high impact strength, has a wide range of applications in fields such as high performance print wiring boards.
Description
Technical field
The present invention relates to polymeric material fields, and in particular to a kind of phenolic resin and its modified thermoset containing phenylate structure
The preparation method of property resin.
Background technology
21 century is the epoch of electronic information rapid development, and current information network comes into 4G developing stage, with letter
The increasingly increase for the treatment of capacity is ceased, information processing capability and information transfer rate to electronic product propose higher and higher want
It asks, therefore electronics and IT products are also towards the direction high speed development of lightening, densification, multifunction, high-frequency high-speed.It is high
Carrier of the frequency high speed printing wiring board (PCB) as signal transmission is used for the material of PCB substrate to realize the high speed of transmission
Material is needed with high reliability, high moisture-proof, high-fire resistance, high dielectric property (low-k and low-dielectric loss), good
The performances such as processability and low cost.Cyanate ester resin because it has the characteristics that excellent dielectric properties, high-fire resistance and easy processing,
It is concerned in aerospace, electric etc., it is considered to be optimal copper-clad plate matrix resin.But cyanic acid
Ester resin is there are curing process poor (solidification temperature height, time are long) and cures big two big disadvantage of resin brittleness, while cyanic acid
The price of ester resin is more expensive, these defects limit the extensive use of cyanate ester resin.
Therefore, in order to obtain the cyanate of excellent combination property, toughening modifying is always the main of cyanate resin modifier
Research contents.
Although being copolymerized or being blended with cyanate ester resin using high-performance thermosetting resin, thermoplastic resin and rubber
The toughness of cyanate ester resin can be improved, but these toughening modifying methods can sacrifice the dielectric properties of cyanate ester resin and heat-resisting
Performance.Therefore, developing a kind of preparation method of the modified cyanic acid ester resin of high comprehensive performance has important application value, packet
Include excellent toughness, simple curing process, high-fire resistance and excellent dielectric properties.
Polyphenylene oxide resin has low-k and low-dielectric loss, good heat resistance, agent of low hygroscopicity and good ruler
Very little stability.The present invention develops a kind of novel phenolic resin, has phenylate structure and phenolic hydroxyl structure, while having high score
The characteristic of son amount, dissolubility is good, melting viscosity is low and excellent rheological property to showing, and not only solves polyphenylene oxide tree
The problems such as melting temperature existing for fat is high, fluidity of molten is poor and is insoluble in usual vehicle, and can be copolymerized with cyanate
Reaction increases compatibility.
High molecular weight phenolic resin with phenylate structure is introduced cyanate ester resin by the present invention, due to benzene in phenolic resin
The effect of ether structure and phenolic hydroxyl group can not only reduce the solidification temperature of cyanate, but also can improve the tough of cyanate ester resin
Property, while excellent heat resistance and dielectric properties can also be kept.
Epoxy resin not only has many advantages, such as excellent adhesive property, good moulding process and low cost, Er Qieke
To react respectively with cyanate ester resin, phenolic resin, to obtain the thermosetting resin of excellent combination property.
The present invention utilizes the high molecular weight novel phenolic resins containing phenylate structure, it and cyanate ester resin copolymerization is anti-
It answers, while introducing epoxy resin and preparing terpolymer resin, keeping former cyanate ester resin excellent dielectric performance and heat resistance
On the basis of, a kind of new modified cyanate ester resin with high tenacity, low cost of research and development.Also find no relevant report at present.
Invention content
The present invention the main contents include：A kind of novel phenolic resins modified heat convertible resin containing phenylate structure is provided
Method and performance description.
Novel phenolic resins according to the present invention have reactivity, and molecular weight is high and controllable, changes with cyanate ester resin
Property system have fabulous compatibility.Epoxy resin not only have excellent adhesive property, good processing and forming technology, it is low at
This features such as, and can be copolymerized simultaneously with cyanate ester resin and phenolic resin.Phenolic resin/cyanate ester resin/ring
Modified cyanic acid ester resin obtained by oxygen resin ternary polymerization has unique design feature, has good wet-hot aging performance, heat
Performance, dielectric properties and it is of low cost the advantages that, have a wide range of applications in fields such as high performance print wiring boards.
The implementation method of the present invention is as follows：
A kind of novel phenolic resins containing phenylate structure, including 2 kinds of synthetic methods, its feature of thermoplastic phenolic resin exist
It is as shown in Figure 1 in structural formula：
N is the integer more than 7 in formula.
The preparation method of wherein thermoplastic phenolic resin is as follows：
Using phenol, in the presence of a lewis acid catalyst, and in Chinese patent application publication number CN101186564A
The methoxyalkyl hexichol ether oligomer for the method synthesis being related to, is made by condensation reaction.Detailed process is：By the benzene of melting
Phenol, methoxyalkyl hexichol ether oligomer be added flask in, lewis acid catalyst is added afterwards, stirs evenly, 140 DEG C, 160
DEG C, 180 DEG C of next stage heating modes, after reaction vacuum distillation remove extra phenol and small molecule, collect faint yellow in flask
Residue be phenolic resin.Weight average molecular weight is more than 1000, and free phenol is low.
The preparation method of wherein thermosetting phenolic resin is as follows：
Using phenol, in the presence of a lewis acid catalyst, and in Chinese patent application publication number CN101186564A
The methoxyalkyl hexichol ether oligomer for the method synthesis being related to, is made by condensation reaction.Detailed process is：By the benzene of melting
Phenol, methoxyalkyl hexichol ether oligomer be added flask in, lewis acid catalyst is added afterwards, stirs evenly, 140 DEG C, 160
DEG C, 180 DEG C of next stage heating modes, after reaction vacuum distillation remove extra phenol and small molecule, collect faint yellow in flask
Residue.By flaxen residue dissolving in receiving flask, formaldehyde and ammonium hydroxide is then added, reacts 40min at 90 DEG C, subtracts
After pressing vacuum removal hydrone, the as solution of thermosetting phenolic resin.Weight average molecular weight is more than 1000, and free phenol is low.
Above 2 kinds of novel phenolic resins containing phenylate structure, can be applied alone can also compound use.
Modified heat convertible resin proposed by the present invention, by 2 kinds in cyanate, epoxy resin, novel phenolic resins (MPF) or
3 kinds of compositions, the mass percent of component are：
Cyanate 10% ~ 99%
Epoxy resin 0% ~ 100%
The novel phenolic resin (MPF) 10 ~ 100% containing phenylate structure
In the present invention, the cyanate ester monomer includes：Bisphenol A cyanate ester (4,4 '-dicyanate base phenyl-propans,
BADCy), bis-phenol L-type cyanate (4,4 '-dicyanate base phenyl-ethanes, BEDCy), bis-phenol M types cyanate (4,4 '-[1,3-
Phenyl is bis- (1- methyl-ethylenes)] double phenylcyanates), Novolac Cyanate Eater Resin (PT), alkyl diphenyl ether type cyanate, alkyl
It is any in xylol type cyanate etc., or can be any in its prepolymer.
In the present invention, the epoxy resin is that the commercialization epoxy resin of the various trades mark can be used.
Modified heat convertible resin preparation method proposed by the present invention, by the way of melting mixing or solution mixing.
Melting mixing：At 100 ~ 140 DEG C, heating cyanate, epoxy resin, MPF keep its melting mixing uniform, obtain shallow
The uncured modified resin of yellow.Its curing process be 160 DEG C/2h+180 DEG C/2h+200 DEG C/2h+220 DEG C/2h+240 DEG C/
2h。
Solution mixes：Cyanate ester resin, epoxy resin, the phenolic resin containing phenylate are dissolved in acetone and other organic solvent,
It is made into certain density solution.Its curing process is 160 DEG C/2h+180 DEG C/2h+200 DEG C/2h+220 DEG C/2h+240 DEG C/2h.
Modified heat convertible resin of the present invention is faint yellow light-transmitting solid resin, has good dielectric properties, resistance to
Hot property and mechanical property.Uncured resin is dissolved in acetone and is prepared into certain density glue, can be used for impregnating enhancing fine
Dimension prepares composite material.It the composite can be widely applied to high performance print circuit board, transparent structure material and high tenacity structure material
In material.
The advantage of the invention is that：The introducings of novel phenolic resins realizes cyanate, phenolic resin, epoxy resin
Co-curing behavior solves the phenomenon that traditional modified cyanic acid ester resin is easily separated, and obtains the thermosetting of high comprehensive performance
Property resin material；The introducing of epoxy resin, which can not only improve impact property, can also reduce cost.Meanwhile the ratio of each component is closed
The molecular weight of system and phenolic resin can make adjustment according to actual application requirement.This resin material is in high performance circuit
Plate, transparent structure material and high tenacity structure material etc. have a wide range of applications.
The present invention tests the heat resistance, dielectric properties and impact property of co-cured resin.
Description of the drawings
Fig. 1 is the structural formula figure of thermoplastic phenolic resin；
Fig. 2 is the dielectric properties and impact property datagram of embodiment 1-9.
Specific implementation mode
Embodiment 1
Epoxy resin (E51) 100g, the phenolic resin 200g containing phenylate structure are weighed, acetone is dissolved in and is configured to solid content and be
60% glue, is then brushed on 7628 glass-fiber-fabrics and prepreg is made, and hangs be put into 100 DEG C of baking ovens afterwards for 24 hours at room temperature, wait for
Volatile matter is less than 1%, takes out in the case of fluidity is suitable, stacks layer by layer, and laminate thickness is controlled in 2.0mm, at 140 DEG C
Pressurization, according to 140 DEG C/2h+160 DEG C/2h+180 DEG C/2h+200 DEG C/2h techniques cure, natural cooling, according to require cut institute
Need size.
Embodiment 2
Bisphenol A cyanate ester 90g is weighed, the phenolic resin 10g containing phenylate structure, melting mixing is uniform at 120 DEG C,
Enter in pre-heated mold, vacuum outgas 0.5h, then in vacuum drying oven according to 160 DEG C/2h+180 DEG C/2h+200 DEG C/
The curing process of 2h+220 DEG C/2h+240 DEG C/2h is cured.
Embodiment 3
Bisphenol A cyanate ester 70g is weighed, the phenolic resin 30g containing phenylate structure, melting mixing is uniform at 120 DEG C,
Enter in pre-heated mold, vacuum outgas 0.5h, then in vacuum drying oven according to 160 DEG C/2h+180 DEG C/2h+200 DEG C/
The curing process of 2h+220 DEG C/2h+240 DEG C/2h is cured.
Embodiment 4
Bisphenol A cyanate ester 50g is weighed, the phenolic resin 50g containing phenylate structure, melting mixing is uniform at 120 DEG C,
Enter in pre-heated mold, vacuum outgas 0.5h, then in vacuum drying oven according to 160 DEG C/2h+180 DEG C/2h+200 DEG C/
The curing process of 2h+220 DEG C/2h+240 DEG C/2h is cured.
Embodiment 5
Weigh bisphenol A cyanate ester 70g, epoxy resin (E51) 100g, the phenolic resin 30g containing phenylate structure, 120
Melting mixing is uniform at DEG C, pours into pre-heated mold, vacuum outgas 0.5h, then in vacuum drying oven according to 160 DEG C/
The curing process of 1h+180 DEG C/1h+200 DEG C/1h+220 DEG C/1h+240 DEG C/2h is cured.
Embodiment 6
Weigh bisphenol A cyanate ester 70g, epoxy resin (E51) 50g, the phenolic resin 30g containing phenylate structure, at 120 DEG C
Lower melting mixing is uniform, pours into pre-heated mold, and vacuum outgas 0.5h, resin curing process is the same as example 5.
Embodiment 7
Weigh bisphenol A cyanate ester 70g, epoxy resin (E51) 66g, the phenolic resin 30g containing phenylate structure, at 120 DEG C
Lower melting mixing is uniform, pours into pre-heated mold, and vacuum outgas 0.5h, resin curing process is the same as example 5.
Embodiment 8
Weigh bisphenol A cyanate ester 50g, epoxy resin (E51) 100g, the phenolic resin 50g containing phenylate structure, 120
Melting mixing is uniform at DEG C, pours into pre-heated mold, and vacuum outgas 0.5h, resin curing process is the same as example 5.
Embodiment 9
Weigh bisphenol A cyanate ester 50g, epoxy resin (E51) 66g, the phenolic resin 50g containing phenylate structure, at 120 DEG C
Lower melting mixing is uniform, pours into pre-heated mold, and vacuum outgas 0.5h, resin curing process is the same as example 5.
Claims (4)
1. a kind of modified heat convertible resin, which is characterized in that by cyanate, epoxy resin, the phenolic resin containing phenylate structure 2
Kind or 3 kinds of compositions, the mass percent of component are：
Cyanate 25~90%
Epoxy resin 0%~50%
Phenolic resin MPF 10~25% containing phenylate structure；
Wherein, the structural formula of the phenolic resin containing phenylate structure isN is more than 7
Integer.
2. modified heat convertible resin according to claim 1, which is characterized in that the monomer of the cyanate includes：Bisphenol-A
Type cyanate, bis-phenol L-type cyanate, bis-phenol M types cyanate, Novolac Cyanate Eater Resin, alkyl diphenyl ether type cyanate, alkyl-dimethyl
It is any in benzene-type cyanate.
3. a kind of preparation method of modified heat convertible resin as described in claim 1, which is characterized in that use melting mixing
Method, i.e., at 100~140 DEG C, heating cyanate, epoxy resin, the phenolic resin containing phenylate structure keep its melting mixing uniform,
Degassed, curing process obtains modified heat convertible resin.
4. a kind of preparation method of modified heat convertible resin as described in claim 1, which is characterized in that mixed using solution
Cyanate, epoxy resin, the phenolic resin containing phenylate structure are dissolved in acetone, are made into certain density solution by method.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410445263.3A CN104212167B (en) | 2014-09-03 | 2014-09-03 | A kind of preparation and its application of low cost low-k thermosetting resin |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410445263.3A CN104212167B (en) | 2014-09-03 | 2014-09-03 | A kind of preparation and its application of low cost low-k thermosetting resin |
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| Publication Number | Publication Date |
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| CN104212167A CN104212167A (en) | 2014-12-17 |
| CN104212167B true CN104212167B (en) | 2018-09-11 |
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Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115490993B (en) * | 2022-10-28 | 2024-03-01 | 西安西电电工材料有限责任公司 | Epoxy resin composition, preparation method and epoxy glass cloth laminated board |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5264500A (en) * | 1991-07-30 | 1993-11-23 | Allied-Signal Inc. | APT resins |
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- 2014-09-03 CN CN201410445263.3A patent/CN104212167B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5264500A (en) * | 1991-07-30 | 1993-11-23 | Allied-Signal Inc. | APT resins |
Non-Patent Citations (2)
| Title |
|---|
| High performance cyanate ester resins/reactive porous polymeric microsphere systems with low-temperature processability;Chao Lin et al;《Composites Science and Technology》;20130702;第85 卷;第148页右栏倒数第1段-第149页右栏第1段，第153页表1，第154页3.4，第155页左栏第2段 * |
| 酚醛改性二苯醚衍生物树脂的研制及其应用;易继涛;《绝缘材料通讯》;19971215(第6期);第19页1.3.1、1.3.2，第20页2.1、2.2.1、2.3 * |
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