CN105348742B - Compositions of thermosetting resin, prepreg and the laminate of the benzoxazine colophony containing melamine-type - Google Patents
Compositions of thermosetting resin, prepreg and the laminate of the benzoxazine colophony containing melamine-type Download PDFInfo
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- CN105348742B CN105348742B CN201510891052.7A CN201510891052A CN105348742B CN 105348742 B CN105348742 B CN 105348742B CN 201510891052 A CN201510891052 A CN 201510891052A CN 105348742 B CN105348742 B CN 105348742B
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Abstract
The invention discloses compositions of thermosetting resin, prepreg and the laminate of a kind of benzoxazine colophony containing melamine-type.Compositions of thermosetting resin of the present invention includes following material：The parts by weight of epoxy resin 100；The parts by weight of melamine-type benzoxazine colophony 50~150；The parts by weight of styrene maleic anhydride copolymer class curing agent 10~70；The parts by weight of fire retardant 5~50；The parts by weight of inorganic filler 5 200；The parts by weight of curing accelerator 0.001~2.Compositions of thermosetting resin of the present invention, there is the advantages that additional amount of flame-retardant agent is few, and heat-resist, dielectric constant is low, and dielectric loss factor is low, excellent fireproof performance, and water absorption resistance is good.
Description
Technical field
The present invention relates to a kind of compositions of thermosetting resin of benzoxazine colophony containing melamine-type, and its half prepared
Cured sheets and laminate, suitable for high-frequency high-speed halogen-free copper-clad plate.
Background technology
With the popularization that 4G is communicated, the rise of 5G communications, and high in the clouds calculates, the extensive use of memory technology, global number
The trend that is doubled and redoubled year by year is presented according to total amount is exchanged, and to the distortion rate of signaling rate and signal requirement also more and more higher.
Signaling rate is mainly relevant with the dielectric constant of material, and dielectric constant (Dk) is smaller, and transmission speed is faster；Signal transmission damage
The owner of lost property is relevant with the dielectric loss factor (Df) of material, and dielectric loss factor is smaller, and signal transmission loss is smaller, and distortion rate is got over
It is low.Therefore, developing low Dk, Df material turns into following printed circuit board material development trend and focus.
2003, European Union promulgated《On scrapping electric/electronic device instruction》With《On being limited in electric/electronic device
System uses the instruction of some harmful components》Two files, the promulgation of the two instructions cause the exploitation of halogen-free flame-resistant electronic material
As study hotspot.The exploitation of Halogen electronic material at present be concentrated mainly in added into resin combination it is substantial amounts of phosphorous or
Nitrogenous small molecule based flame retardant, to reach good flame retardant effect.But substantial amounts of fire retardant, which adds, influences all of material
More performances, particularly heat resistance, such as glass transition temperature Tg, heat decomposition temperature Td.
The content of the invention
The invention provides a kind of thermosetting tree of benzoxazine colophony containing melamine-type for being applicable to high speed substrate
Oil/fat composition, its additional phosphonium flame retardant dosage is few, and heat-resist, dielectric constant is low, and dielectric loss factor is low, and fire resistance is excellent
Different, water absorption resistance is good, suitable for high-frequency high-speed Halogen circuit board.
Present invention also offers prepreg made of above-mentioned compositions of thermosetting resin, above-mentioned thermosetting resin is combined
Thing is dissolved into glue with solvent, and then reinforcing material is immersed in above-mentioned glue, and then heat drying removes solvent, you can
The bonding sheet of semi-cured state.
A further object of the present invention is to provide laminate made of one kind compositions of thermosetting resin, and it has low Jie
Electric constant, the low-dielectric loss factor, high glass-transition temperature, heat-resist, low water absorbable.
Present invention also offers one kind using laminate made of above-mentioned compositions of thermosetting resin, at one or two
And after prepreg superposition described above, metal foil is covered with its single or double, it is hot-forming to produce laminate.
Still a further object of the present invention is to provide printed circuit board made of a kind of above-mentioned compositions of thermosetting resin, the print
Circuit board processed has good heat-resist, excellent in flame retardance, heat-resistant stability, low-k and dielectric loss factor and additional resistance
The characteristics such as agent dosage is few are fired, suitable for the application of high-speed high frequency rate signal transmission.The circuit board includes at least one layer of foregoing layer
Pressing plate, and the circuit board can be made by known printed circuit board processing procedure.
The compositions of thermosetting resin of the present invention has preferable dielectric properties, heat resistance and higher glass transition
Temperature, the application requirement of high-frequency high-speed circuit substrate can be met.
The present invention adopts the following technical scheme that：
A kind of compositions of thermosetting resin, this kind of compositions of thermosetting resin is in terms of organic solid content parts by weight：
1) parts by weight of epoxy resin 100
2) parts by weight of melamine-type benzoxazine resin 50~150
3) parts by weight of styrene-maleic anhydride copolymer class curing agent 10~70
4) parts by weight of fire retardant 5~50
5) inorganic filler 5-200 parts by weight
6) parts by weight of curing accelerator 0.001~2.
Described epoxy resin is halogen-free epoxy resin, can be selected from the one or more in flowing epoxy：It is double
Phenol A types epoxy resin, bisphenol f type epoxy resin, nitrogen-containing epoxy thermoset, phosphorous epoxy resin, phenol aldehyde modified epoxy resin, aralkyl
Base linear phenolic epoxy resin, phenyl alkanes based epoxy resin, alicyclic based epoxy resin, biphenyl type epoxy resin, bicyclic penta
Diene type epoxy resin, naphthalene nucleus type epoxy resin, double bond containing modified epoxy, isocyanate modified epoxy resin.
Preferably, the epoxy resin is selected from phosphorous epoxy resin, aralkyl linear phenolic epoxy resin, biphenyl type epoxy
Resin, dicyclopentadiene type epoxy resin, naphthalene nucleus type epoxy resin, double bond containing modified epoxy, isocyanate-modified ring
One or more in oxygen tree fat.
Described melamine-type benzoxazine colophony has following structural formula：
Wherein R1 has following structureR2 can
Think H, halogen, through or the C1~C15 alkyl and alkoxy that are unsubstituted, through or the C6~C15 aralkyl and virtue that are unsubstituted
Alkoxy, through or C3~C15 cycloalkyl for being unsubstituted, through or the C2-C15 unsaturated alkyls that are unsubstituted or conjugation alkyl with
And bicyclic pentadiene.R3 can be warp or C1~C15 alkyl for being unsubstituted, through or C6~C15 aralkyl for being unsubstituted,
Through or C3~C15 cycloalkyl for being unsubstituted.M is 1~30.
Described melamine-type benzoxazine is with melamine modified phenolic resin, paraformaldehyde and primary amine class chemical combination
Thing is raw material, uses what solvent method formed prepared by the case where reaction temperature is 50~150 DEG C.Reaction passes through vacuum distillation after terminating
Mode remove reaction dissolvent, obtain light yellow clear hard resin.
Described styrene-maleic anhydride copolymer curing agent, it is characterised in that it has following structure
Wherein m=3,4,6 or 8；N=7~10.The thermosetting
Property resin combination in one of which or two kinds and the styrene-maleic anhydride copolymer curing agent of the above can be used.
Described fire retardant is halogen-free flame retardants, including phosphorus flame retardant, nitrogenated flame retardant, organic silicon fibre retardant and
Inorganic combustion inhibitor.Wherein, phosphorus flame retardant includes Phos, phosphinic acid compounds, hypophosphorous acid compound, phosphate compound, oxygen
Change phosphorus compound, organic nitrogen-containing phosphorus compound, phosphazene compound, the organic phosphorus compound of the structure containing DOPO and structure containing DOPO
Epoxy resin or formaldehyde-phenol resin derivative.Nitrogenated flame retardant can be melamine class compound, cyanuric acid compound, isocyanide
Acid compound and nitrogenous epoxy or phenolic resin and its derivative etc..Organic silicon fibre retardant can be organic silicon rubber, silicon
Resin etc..Inorganic combustion inhibitor includes magnesium hydroxide, aluminium hydroxide, aluminum oxide, barium monoxide etc..In the compositions of thermosetting resin
Fire retardant can be any of which fire retardant or the wherein mixture of any two and above fire retardant.
Described inorganic filler, counted based on organic drained weight part, be 5~200 parts, preferably 30~100 mass parts.Institute
State inorganic filler be selected from powdered quartz, fused silica, preparing spherical SiO 2, calcium silicates, carborundum, calcium carbonate,
One in aluminum oxide, aluminium hydroxide, aluminium nitride, boron nitride, titanium dioxide, barium titanate, barium sulfate, talcum powder, polytetrafluoroethylene (PTFE)
Kind is several.
Described curing accelerator is selected from tertiary amines accelerator, imidazoles and imidazole salt accelerator, transition metal and organised
The one or more of compound class accelerator.Selected curing accelerator can any known can accelerate anhydride-cured epoxy
The accelerator of resin or benzoxazine colophony curing rate.
Present invention also offers prepreg made of above-mentioned compositions of thermosetting resin is selected, by above-mentioned thermosetting resin
Composition is dissolved into glue with solvent, and then reinforcing material is immersed in above-mentioned glue, and then heat drying removes solvent, i.e.,
The bonding sheet of semi-cured state can be obtained.
Preferably, solvent is selected from acetone, butanone, cyclohexanone, toluene, DMF, N, N- dimethylacetamides
One or more in amine, glycol monoethyl ether, propylene glycol monomethyl ether.
Preferably, one kind in organic fabric, inorganic fabric, natural fiber, organic synthetic fibers of reinforcing material or
It is several.
Preferably, above-mentioned compositions of thermosetting resin is mixed evenly, finely dispersed glue is made；By glass-fiber-fabric
Foregoing glue is impregnated, is then toasted 2~15 minutes at 80~180 DEG C, you can prepreg is made.
Present invention also offers it is a kind of using above-mentioned compositions of thermosetting resin made by laminate, it is above-mentioned at one
Prepreg single or double is covered with metal foil, or by after two and prepreg described above superposition, in its one side or double
Face is covered with metal foil, hot-forming to produce laminate.
Preferably, prepreg quantity used in laminate can determine that the metal foil can according to laminate thickness
To be copper foil or aluminium foil, thickness determines according to laminate thickness.
Preferably, the step of using above-mentioned prepreg manufacture high-frequency high-speed circuit with substrate (laminate), is as follows：Will be upper
One or more layers is superimposed with each other and forms layer of prepreg the prepreg stated, and gold is covered with the one or both sides of layer of prepreg
Belong to paper tinsel, at a temperature of 0.5MPa~5MPa pressure and 150 DEG C~250 DEG C suppress 1-5 hours form.
The present invention has the following technical effect that：
(1) compositions of thermosetting resin of the present invention, few with additional amount of flame-retardant agent, heat-resist, dielectric constant is low, is situated between
The advantages that electrical loss factor is low, excellent fireproof performance, and water absorption resistance is good.
(2) using prepreg and the additional amount of flame-retardant agent of copper-clad laminate made from above-mentioned compositions of thermosetting resin
Less, the advantages that heat-resist, dielectric constant is low, and dielectric loss factor is low, excellent fireproof performance, and water absorption resistance is good.
Embodiment
To achieve these goals, will be further described below by specific embodiment.It is however, following specific real
Example is applied to be only used for explaining the present invention, the protection domain being not intended to limit the present invention.Used instrument in the present invention, equipment,
Method etc. is instrument commonly used in the art, device and method as do not specialized.
In the examples below, embodiment 1 is melamine-type (synthesis of MP-a) benzoxazine colophonies, embodiment 2~4
It is preparation and the performance evaluation of compositions of thermosetting resin with comparative example 1~4.
The preferred embodiment of the present invention is elaborated below, is the synthesis of melamine-type benzoxazine colophony and system as follows
Raw material used in standby compositions of thermosetting resin：
Melamine modified phenolic resin, producer：Wuxi intelligence science and technology
Paraformaldehyde, producer：Jinan Zheng Zhou Chemical Industry Science Co., Ltd
Aniline, producer：Tianjin Kermel Chemical Reagent Co., Ltd.
Toluene, producer：Guangdong Xi Long chemical plant
Epoxy resin 1, producer：The Chemical Co., Ltd. of Suzhou Ancient one, phosphorous epoxy resin
Epoxy resin 2, producer：Changchun Artificial Resin Factory Co. Ltd., novolac modified epoxy
BA-a resins, producer：Huntsman Hensels step chemical industry, bisphenol-A-aniline type benzoxazine colophony
P-ddm resins, producer：Sichuan Dongcai Technology Group Co., Ltd, 4,4 '-MDA phenol type
Benzoxazine colophony
P-dds resins, producer：Changchun Artificial Resin Factory Co. Ltd., 4,4 '-diaminodiphenyl ether phenol type benzo
Oxazine resin
Curing agent EF-30, producer：TOTAL Cray Valley, styrene-maleic anhydride copolymer (St:MA=3:1)
Curing agent EF-40, producer：TOTAL Cray Valley, styrene-maleic anhydride copolymer (St:MA=4:1)
Curing accelerator, producer：Shikoku Chem, 2-ethyl-4-methylimidazole
Phosphonium flame retardant, producer：Sichuan Dongcai Technology Group Co., Ltd, phenoxy group ring phosphonitrile fire retardant
Filler, producer：Silicon is than section, silica
Coupling agent, producer：DOW CORNING, silane coupler
Solvent, producer：Hangzhou Sheng Li Chemical Co., Ltd.s, butanone
Embodiment 1
MP-a types BOZ synthesis step is as follows：The cyanurotriamide modified phenolic aldehyde of 152g is added in 500ml four-hole boiling flask
(hydroxyl equivalent 150-155g/eq) resin (MP) and 200g toluene, after heating stirring is completely dissolved to MP, add 90g aniline
With 63g paraformaldehydes, 90 DEG C of reaction 6h are warming up to, after reaction terminates, the water for reacting generation and solvent are passed through into vacuum distillation
Mode removes, and obtains flaxen transparent solid 246g, yield 91%.Gel time 720s is measured at 210 DEG C of gained resin,
GPC measures number-average molecular weight 836, weight average molecular weight 1070.
As the formula described in table 1, all components are dissolved with organic solvent-acetone, adjust consolidating for compositions of thermosetting resin
Content is 65wt%, prepares resin adhesive liquid.
The compositions of thermosetting resin is impregnated and is coated on E types glass cloth (2116), and is toasted in 170 DEG C of baking ovens
Resin content 50%wt prepreg is made afterwards.
Take obtained resin content 50%wt prepreg have altogether 6 it is stacked together, then respectively put a copper up and down
Paper tinsel (H OZ), it is placed in compacting in vacuum hotpressing machine and obtains copper-clad laminate.Specific process for pressing is under 2MPa pressure 200
Pressed 2 hours at a temperature of DEG C.The performance of gained doublesided copperclad laminate is shown in Table 1, uses method of testing as follows：
(1) glass transition temperature (Tg), method of testing differential scanning calorimetry (DSC)
(2) flammability, according to U.S.'s UL94 vertical combustions measure
(3) thermal coefficient of expansion (CTE), method of testing use thermomechanical analysis (TMA)
(4) thermally stratified layer time (T288), method of testing use thermomechanical analysis (TMA)
(5) heat decomposition temperature (Td), method of testing use thermogravimetry (TGA)
(6) dielectric constant (Dk) and dielectric loss (Df), method of testing is according to ASTM-D150 and IPC-TM-
6502.5.5.9 measurement
(7) peel strength, method of testing measure according to IPC-TM-6502.4.9.
Table 1
As can be known from the above table, the obtained copper-clad laminate excellent combination property of the present invention, its copper-clad laminate Dk, Df is low,
Additional amount of flame-retardant agent is few, excellent fireproof performance, and Tg, Td are high, and water absorption rate is low, there is preferable PCT performances, and PCB processabilities
Can be excellent, it is suitable for use in halogen-less high frequency high speed printed circuit.
To sum up, the compositions of thermosetting resin of the benzoxazine colophony of the invention containing melamine-type and prepreg, lamination
In the technical scheme of plate, the benzoxazine colophony contains melamine rings so that resin nitrogen content is increased dramatically, and can significantly subtract
The use of few phosphorous or nitrogenous small molecule based flame retardant.Laminate obtained by the present invention has high Tg and Td, excellent resistance
Performance, low-k and the low-dielectric loss factor are fired, while there is low water absorption and low cure shrinkage, suitable for Halogen height
Frequency high speed circuit board.
The present invention chooses preferred embodiment and the principle and technical characteristic of the present invention is described in detail, and not limits this
The protection domain of invention.Any those familiar with ordinary skill in the art, according to thought provided by the invention, in specific embodiment party
In place of the change that formula is made, belong to the protection domain that the present invention is advocated.
Claims (9)
- A kind of 1. compositions of thermosetting resin suitable for high speed substrate, it is characterized in that including following material：The parts by weight of epoxy resin 100；The parts by weight of melamine-type benzoxazine colophony 50~150；The parts by weight of styrene-maleic anhydride copolymer class curing agent 10~70；The parts by weight of fire retardant 5~50；Inorganic filler 5-200 parts by weight；The parts by weight of curing accelerator 0.001~2；Described melamine-type benzoxazine colophony has following structural formula：Wherein, R1 has following structureR2 be H or Halogen, through or the C1~C15 alkyl and alkoxy that are unsubstituted, through or the C6~C15 aralkyl and aralkoxy that are unsubstituted, Through or C3~C15 cycloalkyl for being unsubstituted, through or the C2-C15 unsaturated alkyls that are unsubstituted；R3 is passed through or is unsubstituted C1~C15 alkyl, through or C6~C15 aralkyl for being unsubstituted, through or C3~C15 cycloalkyl for being unsubstituted；M is 1~30.
- 2. compositions of thermosetting resin as claimed in claim 1, it is characterised in that：Described epoxy resin is halogen-free epoxy Resin, the one or more in flowing epoxy：Bisphenol A type epoxy resin, bisphenol f type epoxy resin, nitrogenous epoxy Resin, phosphorous epoxy resin, phenol aldehyde modified epoxy resin, phenyl alkanes based epoxy resin, alicyclic based epoxy resin, biphenyl type Epoxy resin, dicyclopentadiene type epoxy resin, naphthalene nucleus type epoxy resin, double bond containing modified epoxy, isocyanates change Property epoxy resin.
- 3. compositions of thermosetting resin as claimed in claim 1, it is characterised in that：Described melamine-type benzoxazine is Using melamine modified phenolic resin, paraformaldehyde and primary amine compound as raw material, use solvent method in reaction temperature for 50 It is prepared at~150 DEG C；After reaction terminates, reaction dissolvent is removed by way of vacuum distillation, obtains light yellow clear Hard resin.
- 4. compositions of thermosetting resin as claimed in claim 1, it is characterised in that：Described styrene-maleic anhydride copolymer Thing curing agent, there is following structureWherein, m=3,4,6 or 8；n =7~10；One of which or two kinds and the styrene-maleic anhydride copolymer of the above are used in described compositions of thermosetting resin Thing curing agent.
- 5. compositions of thermosetting resin as claimed in claim 1, it is characterised in that：Described fire retardant is halogen-free flame retardants, One or more mixtures in phosphorus flame retardant, nitrogenated flame retardant, organic silicon fibre retardant and inorganic combustion inhibitor.
- 6. compositions of thermosetting resin as claimed in claim 1, it is characterised in that：Described inorganic filler is selected from crystal type two Silica, fused silica, preparing spherical SiO 2, calcium silicates, carborundum, calcium carbonate, aluminum oxide, aluminium hydroxide, aluminium nitride, One or more in boron nitride, titanium dioxide, barium titanate, barium sulfate, talcum powder.
- 7. compositions of thermosetting resin as claimed in claim 1, it is characterised in that：Described curing accelerator is selected from tertiary amines Accelerator, imidazoles and imidazole salt accelerator, the one or more of transition metal organometallic compound class accelerator.
- A kind of 8. prepreg, it is characterized in that the compositions of thermosetting resin solvent described in claim any one of 1-7 is molten Then reinforcing material is immersed in described glue, heat drying removes solvent, you can obtain semi-cured state by solution into glue Bonding sheet；Described solvent be selected from acetone, butanone, cyclohexanone, toluene, N,N-dimethylformamide, DMAC N,N' dimethyl acetamide, One or more mixing in glycol monoethyl ether, propylene glycol monomethyl ether；Described reinforcing material is selected from organic fabric, without woven One or more in thing, natural fiber, organic synthetic fibers.
- A kind of 9. laminate, it is characterised in that：Gold will be covered with a prepreg single or double as claimed in claim 8 Belong to copper foil or aluminium foil, or by after multiple prepreg superpositions as claimed in claim 8, metallic copper is covered with single or double Paper tinsel or aluminium foil, it is hot-forming to produce described laminate.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR102372638B1 (en) * | 2017-07-10 | 2022-03-10 | 디아이씨 가부시끼가이샤 | Laminate, printed wiring board, flexible printed wiring board and molded article using the same |
| CN108410132B (en) * | 2018-02-12 | 2020-08-28 | 浙江华正新材料股份有限公司 | Low-dielectric halogen-free resin composition and low-fluidity prepreg thereof |
| CN108586685B (en) * | 2018-04-13 | 2020-08-11 | 淮北绿洲新材料有限责任公司 | Melamine type benzoxazine prepolymer, copolymer resin and preparation method thereof |
| CN111662616A (en) * | 2020-07-09 | 2020-09-15 | 周红岩 | Thermosetting resin composition and application thereof |
| CN115521427B (en) * | 2022-10-14 | 2024-02-06 | 四川金象赛瑞化工股份有限公司 | Preparation method of melamine-based benzoxazine resin containing Schiff base structure |
| CN115612246A (en) * | 2022-12-15 | 2023-01-17 | 成都科宜高分子科技有限公司 | Composition for forming PCB (printed Circuit Board) hole plugging resin, preparation method, application and filling process |
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| WO1999050352A1 (en) * | 1998-04-01 | 1999-10-07 | Borden Chemical, Inc. | A benzoxazine polymer composition |
| CN103554834B (en) * | 2013-09-04 | 2016-04-20 | 东莞联茂电子科技有限公司 | A kind of halogen-less high frequency resin composition |
| CN104927353B (en) * | 2015-06-12 | 2017-07-11 | 四川东材科技集团股份有限公司 | Fire-retardant non-halogen non-phosphate resin combination and application thereof and for prepreg, laminate, copper-clad plate preparation method |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140073736A1 (en) * | 2012-09-07 | 2014-03-13 | E I Du Pont Nemours And Company | Curable composition comprising bis-benzoxazine, method of curing, and the cured composition so formed |
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Patent Citations (3)
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|---|---|---|---|---|
| WO1999050352A1 (en) * | 1998-04-01 | 1999-10-07 | Borden Chemical, Inc. | A benzoxazine polymer composition |
| CN103554834B (en) * | 2013-09-04 | 2016-04-20 | 东莞联茂电子科技有限公司 | A kind of halogen-less high frequency resin composition |
| CN104927353B (en) * | 2015-06-12 | 2017-07-11 | 四川东材科技集团股份有限公司 | Fire-retardant non-halogen non-phosphate resin combination and application thereof and for prepreg, laminate, copper-clad plate preparation method |
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