CN103396666B - A kind of compositions of thermosetting resin and the prepreg using it to make and veneer sheet - Google Patents
A kind of compositions of thermosetting resin and the prepreg using it to make and veneer sheet Download PDFInfo
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- CN103396666B CN103396666B CN201310341935.1A CN201310341935A CN103396666B CN 103396666 B CN103396666 B CN 103396666B CN 201310341935 A CN201310341935 A CN 201310341935A CN 103396666 B CN103396666 B CN 103396666B
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Abstract
The invention discloses 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.Present invention obtains the compositions of thermosetting resin that various aspects of performance is all excellent, high temperature resistant anti-aging, integrated antenna package, high-frequency high-speed contour performance printed circuit board field can be applied to better.
Description
Technical field
The invention belongs to technical field of electronic materials, relate to a kind of compositions of thermosetting resin and the prepreg using it to make and veneer sheet, can be applicable to high temperature resistant anti-aging, the field such as integrated antenna package, high-speed high frequency.
Background technology
The fast development of electronic circuit board, traditional epoxy resin has been difficult to meet copper-clad plate (CCL) to the high request of the aspects such as thermotolerance, mechanical property, processibility, dielectric properties.Therefore, some high performance resin matrixes, are applied in high-performance CCL field as cyanate, polyphenylene oxide, benzoxazine, bismaleimides etc. have started progressively substituted epoxy resin.
Cyanate ester resin shows excellence in cohesiveness, thermotolerance, dielectric properties etc., but its reaction mechanism is complicated, side reaction is many, price is higher, humidity resistance is poor.Polyphenylene oxide resin dielectric properties are excellent, toughness is good, but its molecular weight is comparatively large, Resin Flow is not enough, simultaneously poor with the consistency of other resins.Benzoxazine resin water-intake rate is low, good heat resistance, cheap, so its cohesiveness and toughness poor, dielectric properties relative deficiency simultaneously.Bismaleimides has splendid thermotolerance and humidity resistance, and dielectric properties are good, have its relatively good cost performance and processibility simultaneously, become a kind of conventional resin matrix in high performance copper clad laminate.
But the bismaleimides of non-modified is poorly soluble, cross-linking density is high, solidification physical property is crisp, is difficult to be used alone, can must uses after modifier modification.At present, conventional method of modifying carries out modification with aromatic diamine compounds (as DDM, DDE, DDS etc.) or allylic compound to it, destroys crystalline texture, improves solvability and toughness etc.Aromatic diamine compounds realizes the modification to bismaleimides by Michael reaction, modified product all has improvement to a certain degree in solvability, toughness, but, aromatic diamine toxicity is larger, the product of modification can only be dissolved in high bp polar solvent (as DMF, NMP etc.), and it still exists larger room for promotion in toughness, cohesiveness simultaneously.And the modified product of allylic cpd (is soluble in low boiling point solvent in toughness, cohesiveness, solvability, as PM, butanone, acetone etc.) all comparatively aromatic diamine compounds have further improvement, be one of method of current bi-maleimide modified main employing.Allylic compound conventional at present, there is allyl group dihydroxyphenyl propane, as allyl group bisphenol S, phenol type allyl group phenolic aldehyde, allyl phenol oxygen, aryl allyl alkylphenol etc., but, often attend to one thing and lose sight of another in thermotolerance, water-intake rate, mechanical property, incendivity, toughness with the bimaleimide resin of these allylic cpd modifications.
Therefore, how obtaining the laminate sheet material of thermotolerance, thermostability, high tenacity, low water absorption, high-modulus, excellent flame retardancy and the good dielectric properties integrating excellent, 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 the prepreg using it to make and veneer sheet.
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:
, wherein, n is the integer of 1 ~ 10;
The structural formula of described bismaleimides is:
，
Wherein R
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 transition metal carboxylate's class, as zinc naphthenate, zinc octoate, aluminium acetylacetonate etc.; Or organic phosphates, as triphenyl phosphorus, triphenyl phosphite 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 epoxy resin, cyanate ester resin, benzoxazine colophony, polyphenylene oxide resin one or more.
Above-mentioned resin combination also can comprise the auxiliary agent such as 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 obtained for 0.5 ~ 3 hour at 100 ~ 200 DEG C.
The present invention asks the prepreg protecting above-mentioned compositions of thermosetting resin to make simultaneously, and above-mentioned thermosetting resin dissolution with solvents is made glue, is then immersed in by strongthener in above-mentioned glue; After flooding after strongthener baking, described prepreg can be obtained.
One or more mixture of described solvent selected from 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 producing the veneer sheet of thickness 0.03 ~ 0.20mm, general use fibrillation cloth, flat fabric.In addition, in order to improve the interface cohesion of resin and glass-fiber-fabric, glass-fiber-fabric generally all needs to carry out chemical treatment, and main method is coupling agent treatment, coupling agent used as epoxy silane, aminosilane, vinyl silanes etc.
Described prepreg be temperature at 100 ~ 200 DEG C, the time be under 1 ~ 10min dry preparation obtain.
The present invention asks to protect a kind of veneer sheet adopting compositions of thermosetting resin to make simultaneously; tinsel is covered with by the single or double of above-mentioned prepreg at one; or after at least 2 are superposed by above-mentioned prepreg; tinsel is covered with at its single or double; compacting, can obtain described veneer sheet.
The quantity of described prepreg determines according to the laminate thickness of customer requirement, available one or more.Described tinsel can be Copper Foil, and also can be aluminium foil, their thickness be not particularly limited.
Described veneer sheet is in vacuum press, and pressure condition is 0.2 ~ 2MPa, and pressing-in temp is 180 ~ 250 DEG C, and pressing time is that under the procedure condition of 2 ~ 4 hours, pressing obtains.
Because technique scheme is used, the present invention compared with prior art has following advantages:
1. the present invention devises 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 excellent thermotolerance, thermostability, high tenacity, low water absorption, high-modulus and excellent flame retardant resistance, and it has good dielectric properties, obtain the compositions of thermosetting resin that various aspects of performance is all excellent, high temperature resistant anti-aging, integrated antenna package, high-frequency high-speed contour performance printed circuit board field can be applied to better.
2. the prepreg adopting resin combination of the present invention to obtain and veneer sheet have excellent thermotolerance, thermostability, high tenacity, low water absorption, high-modulus and excellent flame retardant resistance and good dielectric properties, can be applicable to high temperature resistant anti-aging, the field such as integrated antenna package, high-frequency high-speed, have broad application prospects.
Embodiment
Below in conjunction with embodiment, the invention will be further described:
Synthesis example:
Biphenyl phenolic aldehyde, propyl carbinol and the NaOH aqueous solution is dropped in proportion, stirring reaction 1h at 70 ~ 80 DEG C in reaction flask; Then, be cooled to 40 DEG C, slowly drip a certain proportion of propenyl chloride, be warming up to 70 ~ 80 DEG C after reinforced end and continue reaction 4 ~ 6h; Reaction product, after suction filtration, evaporation, washing, filtration, concentrate etc. processes, obtains brown thick liquid, i.e. biphenyl phenolic aldehyde allyl ethers.
Biphenyl phenolic aldehyde allyl ethers loads in reaction flask, passes into nitrogen protection, is warming up to 190 ~ 200 DEG C, and strict maintenance <205 DEG C, react 4h with this understanding, namely obtain biphenyl type allyl phenol aldehyde cpd.
Embodiment one:
Adopt the biphenyl type allyl phenol aldehyde cpd 55 parts prepared in synthesis example, 4,4 '-diphenyl methane dimaleimide resin 45 parts, reacts 60min and obtains performed polymer at 150 DEG C, adds proper amount of acetone and dissolves; Be uniformly mixed the glue obtaining 62% solids content;
Flood above-mentioned glue with E glass-fiber-fabric, and in 160 DEG C of baking ovens, dry 5min obtain prepreg.
By above-mentioned prepreg, respectively put a Copper Foil up and down, be placed in vacuum hotpressing machine compacting and obtain copper-clad plate.Concrete process for pressing is at 1.5Mpa pressure, and 220 DEG C of temperatures close 4 hours.
The copper clad laminate performance obtained is as shown in table 1.
Embodiment two:
Adopt the biphenyl type allyl phenol aldehyde cpd 45 parts prepared in synthesis example, 4,4 '-diphenyl methane dimaleimide resin 55 parts, reacts 40min and obtains performed polymer at 150 DEG C, adds proper amount of acetone and dissolves; Be uniformly mixed the glue obtaining 62% solids content.
Prepreg, copper clad laminate preparation method are with embodiment one.
The copper clad laminate performance obtained is as shown in table 1.
Embodiment three:
Adopt the biphenyl type allyl phenol aldehyde cpd 55 parts prepared in synthesis example, 4,4 '-Diphenyl Ether Bismaleimide resin 45 parts, reacts 60min and obtains performed polymer at 150 DEG C, adds proper amount of acetone and dissolves; Be uniformly mixed the glue obtaining 62% solids content.
Prepreg, copper clad laminate preparation method are with embodiment one.
The copper clad laminate performance obtained is as shown in table 1.
Embodiment four:
Adopt the biphenyl type allyl phenol aldehyde cpd 55 parts prepared in synthesis example, 4,4 '-diphenyl methane dimaleimide resin 45 parts, reacts 60min and obtains performed polymer at 150 DEG C, adds proper amount of acetone and dissolves; Dissolve completely and add 20 parts of polyfunctional epoxy resins (502H, Japanese chemical drug), 0.2 part of triphenyl phosphorus, be uniformly mixed the glue obtaining 62% solids content.
Prepreg, copper clad laminate preparation method are with embodiment one.
The copper clad laminate performance obtained is as shown in table 1.
Embodiment five:
Adopt the biphenyl type allyl phenol aldehyde cpd 55 parts prepared in synthesis example, 4,4 '-diphenyl methane dimaleimide resin 45 parts, reacts 60min and obtains performed polymer at 150 DEG C, adds proper amount of acetone and dissolves; Dissolve completely and add 100 parts of preparing spherical SiO 2s, be uniformly mixed the glue obtaining 62% solids content.
Prepreg, copper clad laminate preparation method are with embodiment one.
The copper clad laminate performance obtained is as shown in table 1.
Embodiment six:
Adopt the biphenyl type allyl phenol aldehyde cpd 55 parts prepared in synthesis example, 4,4 '-diphenyl methane dimaleimide resin 45 parts, reacts 60min and obtains performed polymer at 150 DEG C, adds proper amount of acetone and dissolves; Dissolve completely and add 10 parts of brominated polycarbonates (BC-58, Chemtura), be uniformly mixed the glue obtaining 62% solids content.
Prepreg, copper clad laminate preparation method are with embodiment one.
The copper clad laminate performance obtained is as shown in table 1.
Embodiment seven:
Adopt the biphenyl type allyl phenol aldehyde cpd 55 parts prepared in synthesis example, 4,4 '-diphenyl methane dimaleimide resin 45 parts, reacts 60min and obtains performed polymer at 150 DEG C, adds proper amount of acetone and dissolves; Dissolve completely and add 15 parts of phosphonitriles (SPB-100, Japan's large tomb chemistry), be uniformly mixed the glue obtaining 62% solids content.
Prepreg, copper clad laminate preparation method are with embodiment one.
The copper clad laminate performance obtained is as shown in table 1.
Comparative example one:
Adopt diallyl bisphenol 55 parts, 4,4 '-diphenyl methane dimaleimide resin 45 parts, reacts 40min and obtains performed polymer at 150 DEG C, adds proper amount of acetone and dissolves the glue obtaining 62% solids content.
Prepreg, copper clad laminate preparation method are with embodiment one.
The copper clad laminate performance obtained is as shown in table 1.
Comparative example two:
Adopt 55 parts, phenol type allyl group phenolic aldehyde, 4,4 '-diphenyl methane dimaleimide resin 45 parts, reacts 40min and obtains performed polymer at 150 DEG C, adds proper amount of acetone and dissolves the glue obtaining 62% solids content.
Prepreg, copper clad laminate preparation method are with embodiment one.
The copper clad laminate performance obtained is as shown in table 1.
Table 1 adopts the copper clad laminate performance of different embodiment and comparative example gained
In table, the testing method of characteristic is as follows:
1) humidity resistance (PCT): get 3 pieces of 10cm × 10cm, thickness is 0.80mm, two sides removes the sample of tinsel, 100 DEG C of dryings 2 hours, then test (PressureCookertest) machine is pressure-cooked, 2 hours are processed under 121 DEG C, 2 normal atmosphere, wicking 10 minutes in the tin stove of 288 DEG C again, whether visual observations has demixing phenomenon.If any 0 in 3 pieces, 1,2,3 pieces of demixing phenomenons are designated as 0/3,1/3,2/3,3/3 respectively.
2) 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 do not have cross bar, illustrates that the toughness of product is poor.With+number to represent, +++ ++ best ,+the poorest.
From upper table, in comparative example one, allylic cpd is allyl group dihydroxyphenyl propane, compared with biphenyl type allyl phenol aldehyde cpd, there is the problems such as water-intake rate is high, poor fire, Tg and TD are low, in comparative example two, allylic cpd is phenol type allyl phenol urea formaldehyde, compared with biphenyl type allyl phenol aldehyde cpd, there is 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 excellent thermotolerance, thermostability, high tenacity, low water absorption, high-modulus and excellent flame retardant resistance and good dielectric properties, can be applicable to high temperature resistant anti-aging, the field such as 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:
, wherein, n is the integer of 1 ~ 10;
The structural formula of described bismaleimides is:
，
Wherein R
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, is characterized in that: described modified bismaleimide prepolymer is that biphenyl type allyl phenol aldehyde cpd and bismaleimides react the prepolymer obtained for 0.5 ~ 3 hour at 100 ~ 200 DEG C.
3. the prepreg adopting compositions of thermosetting resin as claimed in claim 1 to make, is characterized in that: compositions of thermosetting resin dissolution with solvents according to claim 1 is made glue, is then immersed in by strongthener in above-mentioned glue; After flooding after strongthener baking, described prepreg can be obtained.
4. the veneer sheet adopting compositions of thermosetting resin as claimed in claim 1 to make, it is characterized in that: be covered with tinsel at one by the single or double of prepreg according to claim 3, or after at least 2 are superposed by prepreg according to claim 3, tinsel is covered with at its single or double, compacting, can obtain described veneer sheet.
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| 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 |
| CN104861652B (en) * | 2015-05-28 | 2017-05-10 | 苏州生益科技有限公司 | Thermosetting resin composition, and prepreg and laminated board made from thermosetting resin composition |
| 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 |
| 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 |
| CN114231030B (en) * | 2021-12-30 | 2024-06-07 | 东莞联茂电子科技有限公司 | Resin composition, resin glue solution, prepreg, laminated board and printed wiring board |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1989005315A1 (en) * | 1987-11-30 | 1989-06-15 | Mitsubishi Rayon Co., Ltd. | Resin composition for composite material |
| EP0352868A1 (en) * | 1988-07-29 | 1990-01-31 | Shell Internationale Researchmaatschappij B.V. | Bismaleimide-containing thermosetting composition |
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|---|---|---|---|---|
| CN102304343B (en) * | 2011-08-19 | 2013-09-18 | 腾辉电子（苏州）有限公司 | Glue solution for copper-clad substrate, and preparation method thereof |
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2013
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1989005315A1 (en) * | 1987-11-30 | 1989-06-15 | Mitsubishi Rayon Co., Ltd. | Resin composition for composite material |
| EP0352868A1 (en) * | 1988-07-29 | 1990-01-31 | Shell Internationale Researchmaatschappij B.V. | Bismaleimide-containing thermosetting composition |
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