CN103396666A - Thermosetting resin composition and prepreg and laminated sheet prepared with thermosetting resin composition - Google Patents
Thermosetting resin composition and prepreg and laminated sheet prepared with thermosetting resin composition Download PDFInfo
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- CN103396666A CN103396666A CN2013103419351A CN201310341935A CN103396666A CN 103396666 A CN103396666 A CN 103396666A CN 2013103419351 A CN2013103419351 A CN 2013103419351A CN 201310341935 A CN201310341935 A CN 201310341935A CN 103396666 A CN103396666 A CN 103396666A
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Abstract
The invention discloses a thermosetting resin composition comprising, by solid weight: (a) 100 parts of a modified bismaleimide prepolymer, (b) 0-200 parts of an inorganic filling material, (c) 0-40 parts of a flame retardant, and (d) 0-5 parts of a curing accelerator. The bismaleimide prepolymer is a prepolymer of a biphenyl allyl phenolic compound and bismaleimide with a mass ratio of 20-80:20-80. According to the invention, the thermosetting resin composition with excellent performances on all respects is obtained, such that the composition can be applied in the field of high-temperature aging resistance, integrated circuit packaging, and high-performance printed circuit boards with high frequency and high speed, and the like.
Description
Technical field
The invention belongs to technical field of electronic materials, relate to a kind of compositions of thermosetting resin and use prepreg and the veneer sheet of its making, can be applicable to the fields such as high temperature resistant anti-aging, integrated antenna package, high-speed high frequency.
Background technology
The fast development of electronic circuit board, traditional epoxy resin have been difficult to meet the high request of copper-clad plate (CCL) to aspects such as thermotolerance, mechanical property, processibility, dielectric properties.Therefore, some high performance resin matrixes, started progressively substituted epoxy resin as cyanate, polyphenylene oxide, benzoxazine, bismaleimides etc. and be applied in high-performance CCL field.
Cyanate ester resin is excellent in the performance of the aspects such as cohesiveness, thermotolerance, dielectric properties, but its reaction mechanism is complicated, side reaction is many, price is higher, humidity resistance is poor.The polyphenylene oxide resin dielectric properties are excellent, toughness is good, but its molecular weight is large, Resin Flow is not enough, and are simultaneously poor with the consistency of other resins.Benzoxazine resin water-intake rate is low, good heat resistance, cheap, and so its cohesiveness and toughness are poor, simultaneously the dielectric properties relative deficiency.Bismaleimides has splendid thermotolerance and humidity resistance, and dielectric properties are good, has simultaneously its relatively good cost performance and processibility, makes it become a kind of resin matrix commonly used in high performance copper clad laminate.
But the bismaleimides of non-modified is poorly soluble, and cross-linking density is high, the curing physical property is crisp, is difficult to independent use, must can use after modifier modification.At present, method of modifying commonly used is, with aromatic diamine compounds (as DDM, DDE, DDS etc.) or allylic compound, it is carried out modification, destroys crystalline texture, improves solvability and toughness etc.The aromatic diamine compounds is realized modification to bismaleimides by Michael reaction, product after modification is in the improvement that all has aspect solvability, toughness to a certain degree, but, aromatic diamine toxicity is larger, the product of modification can only be dissolved in high bp polar solvent (as DMF, NMP etc.), and still there is larger room for promotion in it aspect toughness, cohesiveness simultaneously.And the product after the allylic cpd modification (is soluble in low boiling point solvent in toughness, cohesiveness, solvability, as PM, butanone, acetone etc.) all than the aromatic diamine compounds, further improvement is arranged, be one of method of bi-maleimide modified main employing at present.The allylic compound of commonly using at present, the allyl group dihydroxyphenyl propane is arranged, as allyl group bisphenol S, phenol type allyl group phenolic aldehyde, allyl phenol oxygen, aryl allyl alkylphenol etc., yet, with the bimaleimide resin of these allylic cpd modifications, often attending to one thing and lose sight of another aspect thermotolerance, water-intake rate, mechanical property, incendivity, toughness.
Therefore, how obtaining the laminate sheet material of the thermotolerance that integrates good, thermostability, high tenacity, low water absorption, high-modulus, excellent flame retardancy and good dielectric properties, is one of problem demanding prompt solution.
Summary of the invention
The object of the invention is to provide a kind of compositions of thermosetting resin and uses prepreg and the veneer sheet of its making.
For achieving the above object, the technical solution used in the present invention is: a kind of compositions of thermosetting resin, with solid weight meter, comprising:
(a) modified bismaleimide prepolymer: 100 parts;
(b) mineral filler: 0 ~ 200 part;
(c) fire retardant: 0 ~ 40 part;
(d) curing catalyst: 0 ~ 5 part;
Described modified bismaleimide prepolymer is the prepolymer of biphenyl type allyl phenol aldehyde cpd and bismaleimides, and the mass ratio of biphenyl type allyl phenol aldehyde cpd and bismaleimides is 20 ~ 80:20 ~ 80;
The structural formula of described biphenyl type allyl phenol aldehyde cpd is:
The structural formula of described bismaleimides is:
R wherein
1For-CH
2-,-SO
2-,-C(CH
3)
2-,-O-or singly-bound, R
2And R
3Identical or different, be respectively-H ,-CH
3,-CH
2CH
3Or-CH (CH
3)
2
Above, described filler is selected from one or more in silicon-dioxide (spherical, crystal type, fusion), aluminium hydroxide, Bao Mushi, magnesium hydroxide, talcum, kaolin, aluminum oxide, zinc borate, polytetrafluorethylepowder powder etc.
Fire retardant can be brominated flame retardant, as tribromo phenyl maleimide, tetrabromo-bisphenol allyl ethers, TDE, brominated Polystyrene, brominated polycarbonate, tetrabromo-bisphenol, brominated epoxy resin; Phosphonium flame retardant, as phosphorous epoxy resin, phosphorus containing phenolic resin, phosphazene compound, phosphate compound, phosphorous cyanate, phosphorous bismaleimides etc.; Nitrogenous compound, as melamine cyanurate etc.; Silicon-containing compound, as silsesquioxane (POSS), organic silicone powder etc.Described fire retardant is selected from one or more of above-mentioned fire retardant.
Described curing catalyst can be tertiary amines, as triethylamine, tripropyl amine etc.; Or imidazoles, as glyoxal ethyline, 2-phenylimidazole, 2-ethyl-4-methylimidazole etc.; Or peroxide, as benzoyl peroxide, dicumyl peroxide etc.; Or the transition metal metal carboxylate, as zinc naphthenate, zinc octoate, aluminium acetylacetonate etc.; Or organic phosphates, as triphenyl phosphorus, triphenyl phosphorous acid ester etc.Described curing catalyst is selected from one or more in above-mentioned promotor.
Compositions of thermosetting resin of the present invention can also comprise other resin, as one or more of epoxy resin, cyanate ester resin, benzoxazine colophony, polyphenylene oxide resin.
Above-mentioned resin combination also can comprise the auxiliary agents such as the thinner, coupling agent, dispersion agent, defoamer, flow agent, anti-aging agent, oxidation inhibitor, dyestuff of 0 ~ 10 part.
In technique scheme, described modified bismaleimide prepolymer is that biphenyl type allyl phenol aldehyde cpd and bismaleimides react the prepolymer that obtained in 0.5 ~ 3 hour under 100 ~ 200 ℃.
The present invention asks for protection the prepreg that above-mentioned compositions of thermosetting resin is made simultaneously, and above-mentioned thermosetting resin is made glue with dissolution with solvents, then strongthener is immersed in above-mentioned glue; After the strongthener baking, can obtain described prepreg after flooding.
Described solvent is selected from one or more mixture of acetone, butanone, mibk, DMF, N,N-dimethylacetamide, ethylene glycol monomethyl ether, propylene glycol monomethyl ether.
Described strongthener can adopt glass-fiber-fabric, as D glass-fiber-fabric, E glass-fiber-fabric, NE glass-fiber-fabric, S glass-fiber-fabric and T glass-fiber-fabric.Here the thickness of glass-fiber-fabric is not particularly limited, but for the veneer sheet of producing thickness 0.03 ~ 0.20 mm, the general use opened fine cloth, flat fabric.In addition, in order to improve resin, with the interface of glass-fiber-fabric, be combined, glass-fiber-fabric generally all needs to carry out chemical treatment, and main method is coupling agent treatment, coupling agent used such as epoxy silane, aminosilane, vinyl silanes etc.
Described prepreg be temperature at 100 ~ 200 ℃, the time is that under 1 ~ 10min, oven dry preparation obtains.
The present invention asks for protection a kind of veneer sheet that adopts compositions of thermosetting resin to make simultaneously; be covered with tinsel at a single or double by above-mentioned prepreg; after perhaps at least 2 being superposeed by above-mentioned prepreg; be covered with tinsel at its single or double; compacting, can obtain described veneer sheet.
The quantity of described prepreg is to determine according to the veneer sheet thickness of customer requirement, available one or more.Described tinsel, can be Copper Foil, can be also aluminium foil, and their thickness is not particularly limited.
Described veneer sheet is in vacuum press, and pressure condition is 0.2 ~ 2MPa, and pressing-in temp is 180 ~ 250 ℃, and pressing time is that under the procedure condition of 2 ~ 4 hours, pressing makes.
Because technique scheme is used, the present invention compared with prior art has following advantages:
1. the present invention has designed a kind of new compositions of thermosetting resin, with a certain proportion of biphenyl type allyl phenol aldehyde cpd and bismaleimides synthetic prepolymer, thus obtained composition has good thermotolerance, thermostability, high tenacity, low water absorption, high-modulus and good flame retardant resistance, and it has dielectric properties preferably, obtain all excellent compositions of thermosetting resin of various aspects of performance, can be applied to better high temperature resistant anti-aging, integrated antenna package, the contour performance printed circuit board of high-frequency high-speed field.
2. adopt prepreg that resin combination of the present invention makes and veneer sheet to have good thermotolerance, thermostability, high tenacity, low water absorption, high-modulus and good flame retardant resistance and dielectric properties preferably, can be applicable to the fields such as high temperature resistant anti-aging, integrated antenna package, high-frequency high-speed, have broad application prospects.
Embodiment
The invention will be further described below in conjunction with embodiment:
Synthesis example:
Drop in proportion biphenyl phenolic aldehyde, propyl carbinol and the NaOH aqueous solution, 70 ~ 80 ℃ of lower stirring reaction 1h in reaction flask; Then, be cooled to 40 ℃, slowly drip a certain proportion of propenyl chloride, be warming up to 70 ~ 80 ℃ after reinforced the end and continue reaction 4 ~ 6h; Reaction product after suction filtration, evaporation, washing, filtration, concentrate etc. processed, obtains the brown thick liquid, i.e. biphenyl phenolic aldehyde allyl ethers.
Biphenyl phenolic aldehyde allyl ethers is packed in reaction flask, passes into nitrogen protection, is warming up to 190 ~ 200 ℃, and strictly keeps＜205 ℃, reacts with this understanding 4h, namely obtains biphenyl type allyl phenol aldehyde cpd.
Embodiment one:
55 parts of the biphenyl type allyl phenol aldehyde cpds for preparing in the employing synthesis example, 4,45 parts of 4 '-diphenyl methane dimaleimide resins, reaction 60min makes performed polymer under 150 ℃, adds proper amount of acetone to dissolve; Be uniformly mixed the glue that obtains 62% solids content;
With the above-mentioned glue of E glass-fiber-fabric dipping, and baking 5min makes prepreg in 160 ℃ of baking ovens.
With above-mentioned prepreg, respectively put up and down a Copper Foil, be placed in the vacuum hotpressing machine compacting and obtain copper-clad plate.Concrete process for pressing is at 1.5Mpa pressure, and 220 ℃ of temperatures were closed 4 hours.
The copper clad laminate performance that obtains is as shown in table 1.
Embodiment two:
45 parts of the biphenyl type allyl phenol aldehyde cpds for preparing in the employing synthesis example, 4,55 parts of 4 '-diphenyl methane dimaleimide resins, reaction 40min makes performed polymer under 150 ℃, adds proper amount of acetone to dissolve; Be uniformly mixed the glue that obtains 62% solids content.
Prepreg, copper clad laminate preparation method are with embodiment one.
The copper clad laminate performance that obtains is as shown in table 1.
Embodiment three:
55 parts of the biphenyl type allyl phenol aldehyde cpds for preparing in the employing synthesis example, 4,45 parts of 4 '-Diphenyl Ether Bismaleimide resins, reaction 60min makes performed polymer under 150 ℃, adds proper amount of acetone to dissolve; Be uniformly mixed the glue that obtains 62% solids content.
Prepreg, copper clad laminate preparation method are with embodiment one.
The copper clad laminate performance that obtains is as shown in table 1.
Embodiment four:
55 parts of the biphenyl type allyl phenol aldehyde cpds for preparing in the employing synthesis example, 4,45 parts of 4 '-diphenyl methane dimaleimide resins, reaction 60min makes performed polymer under 150 ℃, adds proper amount of acetone to dissolve; Add 20 parts of polyfunctional epoxy resins (502H, Japanese chemical drug), 0.2 part of triphenyl phosphorus after dissolve complete, be uniformly mixed the glue that obtains 62% solids content.
Prepreg, copper clad laminate preparation method are with embodiment one.
The copper clad laminate performance that obtains is as shown in table 1.
Embodiment five:
55 parts of the biphenyl type allyl phenol aldehyde cpds for preparing in the employing synthesis example, 4,45 parts of 4 '-diphenyl methane dimaleimide resins, reaction 60min makes performed polymer under 150 ℃, adds proper amount of acetone to dissolve; Add 100 parts of preparing spherical SiO 2s after dissolve complete, be uniformly mixed the glue that obtains 62% solids content.
Prepreg, copper clad laminate preparation method are with embodiment one.
The copper clad laminate performance that obtains is as shown in table 1.
Embodiment six:
55 parts of the biphenyl type allyl phenol aldehyde cpds for preparing in the employing synthesis example, 4,45 parts of 4 '-diphenyl methane dimaleimide resins, reaction 60min makes performed polymer under 150 ℃, adds proper amount of acetone to dissolve; Add 10 parts of brominated polycarbonates (BC-58, Chemtura) after dissolve complete, be uniformly mixed the glue that obtains 62% solids content.
Prepreg, copper clad laminate preparation method are with embodiment one.
The copper clad laminate performance that obtains is as shown in table 1.
Embodiment seven:
55 parts of the biphenyl type allyl phenol aldehyde cpds for preparing in the employing synthesis example, 4,45 parts of 4 '-diphenyl methane dimaleimide resins, reaction 60min makes performed polymer under 150 ℃, adds proper amount of acetone to dissolve; Add 15 parts of phosphonitriles (SPB-100, Japan's large tomb chemistry) after dissolve complete, be uniformly mixed the glue that obtains 62% solids content.
Prepreg, copper clad laminate preparation method are with embodiment one.
The copper clad laminate performance that obtains is as shown in table 1.
Comparative Examples one:
Adopt 55 parts of diallyl bisphenols, 4,45 parts of 4 '-diphenyl methane dimaleimide resins, reaction 40min obtains performed polymer under 150 ℃, adds proper amount of acetone to dissolve the glue that obtains 62% solids content.
Prepreg, copper clad laminate preparation method are with embodiment one.
The copper clad laminate performance that obtains is as shown in table 1.
Comparative Examples two:
Adopt 55 parts, phenol type allyl group phenolic aldehyde, 4,45 parts of 4 '-diphenyl methane dimaleimide resins, reaction 40min obtains performed polymer under 150 ℃, adds proper amount of acetone to dissolve the glue that obtains 62% solids content.
Prepreg, copper clad laminate preparation method are with embodiment one.
The copper clad laminate performance that obtains is as shown in table 1.
Table 1 adopts the copper clad laminate performance of different embodiment and Comparative Examples gained
In table, the testing method of characteristic is as follows:
1) humidity resistance (PCT): getting 3 10cm * 10cm, thickness is the sample that tinsel is removed on 0.80mm, two sides, 100 ℃ of dryings 2 hours, then pressure-cook test (Pressure Cooker test) machine, processed 2 hours under 121 ℃, 2 normal atmosphere, wicking 10 minutes in the tin stove of 288 ℃ again, whether visual observations has demixing phenomenon.In 3, if any 0,1,2,3 demixing phenomenons are designated as respectively 0/3,1/3,2/3,3/3.
2) the measurement thickness of sample is 1.6mm, and joining this structure is 8 7628 glass-fiber-fabrics.
3) impelling strength test: use 5512 Apparatus for Impacting at low-temp, Apparatus for Impacting at low-temp height of the fall 45cm, whereabouts weight weight 1kg.The judge that toughness is good and bad: cross bar is clear and very thin, illustrates that the toughness of product is better; On the contrary, cross bar is fuzzy or there is no cross bar, illustrates that the toughness of product is poor.With+number expression, ++ +++best ,+the poorest.
From upper table as seen, in Comparative Examples one, allylic cpd is the allyl group dihydroxyphenyl propane, compare with biphenyl type allyl phenol aldehyde cpd, have that water-intake rate is high, poor fire, Tg and the problem such as TD is low, in Comparative Examples two, allylic cpd is phenol type allyl phenol urea formaldehyde, compare with biphenyl type allyl phenol aldehyde cpd, have the problems such as water-intake rate is high, dielectric properties are poor, toughness is not enough.And veneer sheet of the present invention has good thermotolerance, thermostability, high tenacity, low water absorption, high-modulus and good flame retardant resistance and good dielectric properties, can be applicable to the fields such as high temperature resistant anti-aging, integrated antenna package, high-frequency high-speed, have broad application prospects.
Claims (4)
1. a compositions of thermosetting resin, is characterized in that,, with solid weight meter, comprising:
(a) modified bismaleimide prepolymer: 100 parts;
(b) mineral filler: 0 ~ 200 part;
(c) fire retardant: 0 ~ 40 part;
(d) curing catalyst: 0 ~ 5 part;
Described modified bismaleimide prepolymer is the prepolymer of biphenyl type allyl phenol aldehyde cpd and bismaleimides, and the mass ratio of biphenyl type allyl phenol aldehyde cpd and bismaleimides is 20 ~ 80:20 ~ 80;
The structural formula of described biphenyl type allyl phenol aldehyde cpd is:
The structural formula of described bismaleimides is:
R wherein
1For-CH
2-,-SO
2-,-C(CH
3)
2-,-O-or singly-bound, R
2And R
3Identical or different, be respectively-H ,-CH
3,-CH
2CH
3Or-CH (CH
3)
2
2. compositions of thermosetting resin according to claim 1, it is characterized in that: described modified bismaleimide prepolymer is that biphenyl type allyl phenol aldehyde cpd and bismaleimides react the prepolymer that obtained in 0.5 ~ 3 hour under 100 ~ 200 ℃.
3. a prepreg that adopts compositions of thermosetting resin as claimed in claim 1 to make, is characterized in that: thermosetting resin claimed in claim 1 is made glue with dissolution with solvents, then strongthener is immersed in above-mentioned glue; After the strongthener baking, can obtain described prepreg after flooding.
4. veneer sheet that adopts compositions of thermosetting resin as claimed in claim 1 to make, it is characterized in that: at a single or double by prepreg claimed in claim 3, be covered with tinsel, after perhaps at least 2 being superposeed by prepreg claimed in claim 3, be covered with tinsel at its single or double, compacting, can obtain described veneer sheet.
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| CN201310341935.1A CN103396666B (en) | 2013-08-07 | 2013-08-07 | A kind of compositions of thermosetting resin and the prepreg using it to make and veneer sheet |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104861652A (en) * | 2015-05-28 | 2015-08-26 | 苏州生益科技有限公司 | Thermosetting resin composition, and prepreg and laminated board made from thermosetting resin composition |
| KR20170023812A (en) * | 2014-07-01 | 2017-03-06 | 메이와가세이가부시키가이샤 | Allyl ether-modified biphenyl aralkyl novolac resin, allyl-modified biphenyl aralkyl novolac resin, method for producing same and composition using same |
| CN110655791A (en) * | 2019-09-30 | 2020-01-07 | 艾蒙特成都新材料科技有限公司 | High heat-resistant low-dielectric active ester resin composition and preparation method of laminated board |
| CN112679901A (en) * | 2020-12-22 | 2021-04-20 | 广东盈骅新材料科技有限公司 | Thermosetting resin composition and use thereof |
| CN114231030A (en) * | 2021-12-30 | 2022-03-25 | 东莞联茂电子科技有限公司 | Resin composition, resin liquid solution, prepreg, laminate, and printed wiring board |
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20170023812A (en) * | 2014-07-01 | 2017-03-06 | 메이와가세이가부시키가이샤 | Allyl ether-modified biphenyl aralkyl novolac resin, allyl-modified biphenyl aralkyl novolac resin, method for producing same and composition using same |
| CN106795276A (en) * | 2014-07-01 | 2017-05-31 | 明和化成株式会社 | The modified biphenyl aralkyl novolac resin of allyl ether, the modified biphenyl aralkyl novolac resin of pi-allyl, its manufacture method and its composition is used |
| CN106795276B (en) * | 2014-07-01 | 2019-09-24 | 明和化成株式会社 | Allyl ether or the modified biphenyl aralkyl novolac resin of allyl, its manufacturing method and the composition for having used it |
| TWI728950B (en) * | 2014-07-01 | 2021-06-01 | 日商明和化成股份有限公司 | Allyl ether modified biphenyl aralkyl phenolic resin, allyl modified biphenyl aralkyl phenolic resin, manufacturing method thereof, and composition using the same |
| KR102413139B1 (en) * | 2014-07-01 | 2022-06-27 | 우베 가부시키가이샤 | Allyl ether-modified biphenyl aralkyl novolac resin, allyl-modified biphenyl aralkyl novolac resin, method for producing same and composition using same |
| CN104861652A (en) * | 2015-05-28 | 2015-08-26 | 苏州生益科技有限公司 | Thermosetting resin composition, and prepreg and laminated board made from thermosetting resin composition |
| CN110655791A (en) * | 2019-09-30 | 2020-01-07 | 艾蒙特成都新材料科技有限公司 | High heat-resistant low-dielectric active ester resin composition and preparation method of laminated board |
| CN110655791B (en) * | 2019-09-30 | 2022-03-01 | 艾蒙特成都新材料科技有限公司 | High heat-resistant low-dielectric active ester resin composition and preparation method of laminated board |
| CN112679901A (en) * | 2020-12-22 | 2021-04-20 | 广东盈骅新材料科技有限公司 | Thermosetting resin composition and use thereof |
| CN112679901B (en) * | 2020-12-22 | 2023-03-10 | 广东盈骅新材料科技有限公司 | Thermosetting resin composition and use thereof |
| CN114231030A (en) * | 2021-12-30 | 2022-03-25 | 东莞联茂电子科技有限公司 | Resin composition, resin liquid solution, prepreg, laminate, and printed wiring board |
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