CN101613531A - A kind of resin molding infiltration process resin and preparation method thereof - Google Patents
A kind of resin molding infiltration process resin and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a kind of resin molding infiltration process resin and preparation method thereof.By weight, 100 parts of bimaleimide resins and 50～90 parts of diallyl phenyl compounds 120～140 ℃ of prepolymerization reactions 30～60 minutes, are obtained prepolymer; Treat to add 20～300 parts of cyanate ester resins after prepolymer is cooled to 100～120 ℃,, promptly obtain bismaleimide-triazine resin (BT) resin 100～120 ℃ of pre-polymerizations 30～60 minutes; 10～50 parts of hyperbranched polyorganosiloxanes are added the BT resin, and after 20～200 minutes, the cooling film forming promptly obtains a kind of resin molding infiltration process resin molding (sheet) in 80～100 ℃ of reactions.The matrix material that is made by this diaphragm has excellent comprehensive mechanical properties, thermotolerance and excellent dielectric properties, can be used for numerous high-technology fields such as space flight and aviation, electronic information, communications and transportation.
Description
Technical field
The present invention relates to a kind of resin matrix and preparation method thereof, resin that particularly a kind of resin molding infiltration (RFI) technology is used and preparation method thereof belongs to technical field of polymer materials.It is adapted to RFI prepared matrix material, and prepared matrix material has excellent comprehensive mechanical properties, can be used for high-technology fields such as space flight and aviation, electronic information.
Background technology
The low-cost manufacturing technique of high performance composite is the new development trends that attract people's attention in the present international matrix material research field.It has broken the convention that high performance composite for a long time must have high manufacturing cost, for high performance composite have been opened up wide Application Areas.The composite material manufacturing technology that resin molding infiltration (RFI) technology occurs under this thought guidance just.It can produce fibre content height (weight ratio is near 70%), porosity extremely low (near 0) but, mechanical property excellence, goods favorable reproducibility, the large-scale composite material product of wall thickness regulated at will and the product of complicated shape, and can carry out structure design according to performance requriements.RFI technology is simple, need not to prepare prepreg, therefore; volatile matter is few; VOC in the workshop air (volatileorganic compounds, content of volatile organic compound) meets International Maritime Organizaton (IMO) standard, thereby more helps operator's healthy and environment protection.In addition, RFI technological forming pressure is low, with short production cycle, labour intensity is low, and is low to moulding stock and equipment requirements, thereby greatly reduce the manufacturing cost (than traditional technology laminated into type low 50%) of matrix material.
Because RFI technology, the processing performance of resin matrix has been proposed strict more requirement in the following aspects: (1) resin matrix is film forming at ambient temperature, middle low-temperature curing; (2) made film has good toughness, and is flexible and not broken, and tack-free; (3) low viscosity that under working temperature, can continue for some time, then its viscosity of rising along with temperature increases very fast; (4) solidification value is higher than melt temperature, makes resin can fully soak into precast body; (5) fiber preform is had good wetting property, infiltration ability (rate of permeation), matching and adhesivity during fusion, product is difficult for taking place coming off of fiber and interlaminar resin under stress condition.
At present, unsaturated polyester and Resins, epoxy are mainly as the matrix resin in the RFI technology.The unsaturated polyester poor heat resistance, over-all properties is general, so development prospect is little; The Resins, epoxy wet-hot aging performance is general, has limited further developing of RFI technology.Therefore, providing a kind of high performance resin matrix is the research emphasis of RFI technology field.In addition, some have the Application Areas of high request to resin in space flight and aviation, electronic information etc., also require resin matrix itself to have high heat resistance, excellent comprehensive mechanical properties and anti-environmental aging performance.
Cyanate (CE) and bismaleimides (BMI) are the thermosetting resins of two kinds of excellent propertys, CE has excellent mechanical property, dielectric properties (ε ≈ 3.1, tg δ=0.007) and processing performance, BMI has high heat-resisting (340 ℃ of Tg ≈), approach by chemical copolymerization or physical blending combines the two, is bismaleimide-triazine resin (being called for short the BT resin).The BT resin has been realized the excellent-excellent combination of two kinds of resin properties, has thermotolerance height (Tg=200～340 ℃) and the good advantage of dielectric properties, is the first-selected resin matrix of preparation high performance composite.But BT resin viscosity height, property is crisp under the room temperature condition, can't film forming, and need processing condition compacted under at comparatively high temps or cryogenic high pressure, be not suitable for RFI technological forming matrix material.In addition, the toughness of this material is still waiting further raising.
Beam state is just waiting the people at document " High-Performance Bismaleimide Resin Film forResin Film Infusion " (Journal of Applied Polymer Science, v81, n12, p 2918-2922, Sep 19 2001) in, disclosing a kind of is matrix with the allylic cpd MODIFIED BMI, by adding polyethersulfone resin, has developed the method for high-performance RFI film.Because the second-order transition temperature (Tg=225 ℃) of polyethersulfone is lower than BMI, and with BMI copolymerization does not take place, so, cause that the thermotolerance of resin matrix descends to some extent after the modification.
The hyperbranched polymer particular structure makes it to have the different physical and chemical performance of traditional polymer, shows that viscosity is little, solvability is good; It can also make it to have good reactivity by the distribute hyperbranched polymer of a large amount of functional groups of design surface, and therefore, hyperbranched polymer has been used for the modification of thermosetting resin.But, how to design hyperbranched polymer and come modification BT resin, make it keeping obtaining to have the more resin system that can be used for the RFI moulding of high tenacity on excellent dielectric properties of BT resin and the stable on heating basis, at present, still be the difficult problem of a pendulum in face of the investigator.
Summary of the invention
In order to overcome the existing deficiency of background technology, the object of the present invention is to provide a kind of resin molding infiltration process resin and preparation method thereof with dielectric properties of excellent comprehensive mechanical properties, thermotolerance and excellence.
The technical scheme that realizes the foregoing invention purpose provides a kind of resin molding infiltration process resin, it is characterized in that: by weight, it comprises two bismaleimide resins of 100 parts, 50～90 parts diallyl phenyl compound, 20～300 parts cyanate ester resin and 10～50 parts hyperbranched polyorganosiloxane.
Described bimaleimide resin is 4,4 '-dimaleoyl imino ditane, 4,4 '-dimaleoyl imino phenyl ether, 4,4 '-dimaleoyl imino sulfobenzide, N-phenyl substituted maleimide amine or its combination; Described diallyl phenyl compound is diallyl bisphenol, diallyl bisphenol ether, diallyl bisphenol S or its combination; Described cyanate ester resin is bisphenol A cyanate ester resin, dicyclopentadiene type ethylene rhodanate resin or its combination.
A kind of resin molding infiltration process preparation method of resin is characterized in that step comprises:
1) by weight,, obtains prepolymer with 100 parts of bimaleimide resins and 50～90 parts of diallyl phenyl compounds prepolymerization reaction 30～60 minutes under 120～140 ℃ temperature condition;
2) treat that prepolymer is cooled to 100～120 ℃ after, add 20～300 parts of cyanate ester resins, pre-polymerization is 30～60 minutes under 100～120 ℃ temperature condition, obtains bismaleimide-triazine resin;
3) 10～50 parts hyperbranched polyorganosiloxane is joined in the above-mentioned Bismaleimide Triazine, under 80～100 ℃ temperature condition, reacted 20～200 minutes, promptly obtain a kind of resin molding infiltration process resin.
Therefore reasons such as, blend difficulty big owing to thermoplastic resin melt temperature height, viscosity, exist after traditional thermoplastic resin and the thermosetting resin blending resin film forming and are separated and problem such as manufacturability difference.The invention has the advantages that: the low viscosity of utilizing hyperbranched polyorganosiloxane, has favorable manufacturability after making pure thermosetting resin modification, and, hyperbranched polyorganosiloxane with abundant reactive group make and itself and BT resin generation copolymerization guaranteed that resin has equal phase structure.In addition, hyperbranched polyorganosiloxane has been inherited outstanding thermotolerance, snappiness and the dielectric properties of polysiloxane, and therefore, prepared resin has outstanding over-all properties, is a kind of resin matrix that is applicable to that the resin molding infiltration process is used.
Embodiment
Below in conjunction with embodiment the present invention is further described:
Embodiment 1:
Present embodiment technical scheme concrete steps are as follows:
γ-(2,3-epoxy third oxygen) propyl trimethoxy silicane (KH-560) and deionized water were poured in the reaction flask in 1: 1.2 in molar ratio, regulated pH=3, be heated to 60 ℃ of reaction 7hr, obtaining hyperbranched polyorganosiloxane behind the dry 4hr in the vacuum drying oven.
With 100g 4,4 '-bismaleimides ditane and 86g O, O '-diallyl bisphenol adds in the reaction flask, obtains performed polymer after being heated to 135 ℃ of prepolymerization reaction 35min.
Treat to add the 30g bisphenol A cyanate ester after performed polymer is cooled to 100 ℃,, obtain the BT resin at 100 ℃ of reaction 45min.
In the BT resin, add the hyperbranched polyorganosiloxane that 10g presses the preparation of present embodiment method, promptly obtain a kind of resin molding infiltration process resin behind the reaction 30min down at 80 ℃.Adopt the hydrostomia method after finishing or scrape embrane method film forming or sheet on polyester film, be cooled to room temperature, promptly obtain a kind of resin molding infiltration process resin molding (sheet), its outward appearance is orange-yellow transparent film, can rub folding arbitrarily, and is tack-free.
Embodiment 2
γ-(2,3-epoxy third oxygen) propyl trimethoxy silicane (KH-560) and deionized water were poured in the reaction flask in 1: 1.1 in molar ratio, regulated pH=3, be heated to 60 ℃ of reaction 7hr, dry 4hr obtains hyperbranched polyorganosiloxane in vacuum drying oven.
With 100g4,4 '-bismaleimides ditane, 30gO, O '-diallyl bisphenol and 25g diallyl bisphenol ether add in the reaction flask, are heated to 130 ℃, behind the prepolymerization reaction 30min, obtain performed polymer.
Treat to add 35g bisphenol A cyanate ester and 15g dicyclopentadiene type ethylene rhodanate after performed polymer is cooled to 120 ℃,, obtain the BT resin at 120 ℃ of reaction 30min.
After treating that the BT resin is cooled to 90 ℃, add the hyperbranched polyorganosiloxane that 20g presses the preparation of present embodiment method, promptly obtain a kind of resin molding infiltration process resin behind the reaction 40min down at 90 ℃.Adopt the hydrostomia method after finishing or scrape embrane method film forming on polyester film, be cooled to room temperature, promptly obtain a kind of resin molding infiltration process resin molding (sheet), its outward appearance is orange-yellow transparent film, can rub folding arbitrarily, and is tack-free.
Embodiment 3
With 100g 4,4 '-bismaleimides ditane and 90g O, O '-diallyl bisphenol adds in the reaction flask, obtains performed polymer after being heated to 120 ℃ of prepolymerization reaction 40min.
Treat to add the 50g bisphenol A cyanate ester after performed polymer is cooled to 100 ℃,, obtain the BT resin at 100 ℃ of reaction 60min.
After treating that the BT resin is cooled to 90 ℃, add the hyperbranched polyorganosiloxane that 16g presses the preparation of embodiment 1 method, promptly obtain a kind of resin molding infiltration process resin behind the reaction 40min down at 90 ℃.Adopt the hydrostomia method after finishing or scrape embrane method film forming on polyester film, be cooled to room temperature, promptly obtain a kind of resin molding infiltration process resin molding (sheet), its outward appearance is orange-yellow transparent film, can rub folding arbitrarily, and is tack-free.
Embodiment 4
γ-(2,3-epoxy third oxygen) propyl trimethoxy silicane (KH-560) and deionized water were poured in the reaction flask in 1: 1.2 in molar ratio, regulated pH=4, be heated to 60 ℃ of reaction 7hr, dry 4hr obtains hyperbranched polyorganosiloxane in vacuum drying oven.
With 80g 4,4 '-bismaleimides ditane, 10g 4,4 '-dimaleoyl imino phenyl ether, 10g N-phenyl methyl substituted maleimide amine, 70g O, O '-diallyl bisphenol and 20g diallyl bisphenol ether add in the reaction flask, obtain performed polymer after being heated to 140 ℃ of prepolymerization reaction 60min.
Treat to add 60g bisphenol A cyanate ester and 40g dicyclopentadiene type ethylene rhodanate after performed polymer is cooled to 120 ℃,, obtain the BT resin at 120 ℃ of reaction 60min.
After treating that the BT resin is cooled to 100 ℃, add the hyperbranched polyorganosiloxane that 30g press the preparation of present embodiment method) and 20g press the hyperbranched polyorganosiloxane that embodiment 2 methods prepare, after reacting 60min under 100 ℃, promptly obtaining a kind of resin molding infiltration process resin.Adopt the hydrostomia method after finishing or scrape embrane method film forming on polyester film, be cooled to room temperature, promptly obtain a kind of resin molding infiltration process resin molding (sheet).
Embodiment 5
γ-methacryloxypropyl trimethoxy silane (KH570) and deionized water were poured in the reaction flask in 1: 1.3 in molar ratio, regulated pH=3, be heated to 60 ℃ of reaction 7hr, obtaining hyperbranched polyorganosiloxane behind the dry 4hr in the vacuum drying oven.
With 100g 4,4 '-diphenyl methane dimaleimide, 35g O, O '-diallyl bisphenol, 10g diallyl bisphenol ether and 5g diallyl bisphenol S add in the reaction flask, obtain performed polymer after being heated to 140 ℃ of prepolymerization reaction 30min.
Treat to add the 20g bisphenol A cyanate ester after performed polymer is cooled to 120 ℃,, obtain the BT resin at 120 ℃ of reaction 30min.
After treating that the BT resin is cooled to 100 ℃, add the 10g hyperbranched polyorganosiloxane of pressing the preparation of present embodiment method, promptly obtain a kind of resin molding infiltration process resin behind the reaction 20min down at 100 ℃.Adopt the hydrostomia method after finishing or scrape embrane method film forming on polyester film, be cooled to room temperature, promptly obtain a kind of resin molding infiltration process resin molding (sheet), its outward appearance is orange-yellow transparent film, can rub folding arbitrarily, and is tack-free.
Embodiment 6
γ-methacryloxypropyl trimethoxy silane (KH570) and deionized water were poured in the reaction flask in 1: 1.1 in molar ratio, regulated pH=2, be heated to 50 ℃ of reaction 7hr, dry 4hr obtains hyperbranched polyorganosiloxane in vacuum drying oven.
With 100g 4,4 '-bismaleimides ditane and 75g O, O '-diallyl bisphenol and 10g diallyl bisphenol S add in the reaction flask, obtain performed polymer after being heated to 135 ℃ of prepolymerization reaction 40min.
Treat to add the 300g dicyclopentadiene type ethylene rhodanate resin after performed polymer is cooled to 110 ℃,, obtain the BT resin at 110 ℃ of reaction 40min.
After treating that the BT resin is cooled to 85 ℃, add the hyperbranched polyorganosiloxane that 40g presses the preparation of present embodiment method, promptly obtain a kind of resin molding infiltration process resin behind the reaction 200min down at 95 ℃.Adopt the hydrostomia method after finishing or scrape embrane method film forming on polyester film, be cooled to room temperature, promptly obtain a kind of resin molding infiltration process resin molding (sheet).
Embodiment 7
γ-(2,3-epoxy third oxygen) propyl trimethoxy silicane (KH-560) and deionized water were poured in the reaction flask in 1: 1.1 in molar ratio, regulated pH=4, be heated to 60 ℃ of reaction 7hr, dry 3hr obtains hyperbranched polyorganosiloxane in vacuum drying oven.
With 100g 4,4 '-bismaleimides ditane and 86g O, O '-diallyl bisphenol adds in the reaction flask, obtains performed polymer after being heated to 135 ℃ of prepolymerization reaction 35min.
Treat to add the 250g bisphenol A cyanate ester after performed polymer is cooled to 110 ℃,, obtain the BT resin at 110 ℃ of reaction 45min.
After treating that the BT resin is cooled to 90 ℃, add the hyperbranched polyorganosiloxane that 20g presses the preparation of present embodiment method, promptly obtain a kind of resin molding infiltration process resin behind the reaction 35min down at 90 ℃.Adopt the hydrostomia method after finishing or scrape embrane method film forming on polyester film, be cooled to room temperature, promptly obtain a kind of resin molding infiltration process resin molding (sheet).
Embodiment 8
Prepare hyperbranched polyorganosiloxane by embodiment 1 method.
With 100g 4,4 '-bismaleimides ditane and 86g O, O '-diallyl bisphenol adds in the reaction flask, obtains performed polymer after being heated to 135 ℃ of prepolymerization reaction 35min.
Treat to add 130g bisphenol A cyanate ester and 80g dicyclopentadiene type ethylene rhodanate resin after performed polymer is cooled to 110 ℃,, obtain the BT resin at 110 ℃ of reaction 45min.
After treating that the BT resin is cooled to 90 ℃, add the hyperbranched polyorganosiloxane that 20g presses the preparation of embodiment 1 method, promptly obtain a kind of resin molding infiltration process resin behind the reaction 35min down at 90 ℃.Adopt the hydrostomia method after finishing or scrape embrane method film forming on polyester film, be cooled to room temperature, promptly obtain a kind of resin molding infiltration process resin molding (sheet).
Claims (5)
1. resin molding infiltration process resin, it is characterized in that: by weight, it comprises two bismaleimide resins of 100 parts, 50～90 parts diallyl phenyl compound, 20～300 parts cyanate ester resin and 10～50 parts hyperbranched polyorganosiloxane.
2. a kind of resin molding infiltration process resin according to claim 1, it is characterized in that: described bimaleimide resin is 4,4 '-dimaleoyl imino ditane, 4,4 '-dimaleoyl imino phenyl ether, 4,4 '-dimaleoyl imino sulfobenzide, N-phenyl substituted maleimide amine or its combination.
3. a kind of resin molding infiltration process resin according to claim 1 is characterized in that: described diallyl phenyl compound is diallyl bisphenol, diallyl bisphenol ether, diallyl bisphenol S or its combination.
4. a kind of resin molding infiltration process resin according to claim 1 is characterized in that: described cyanate ester resin is bisphenol A cyanate ester resin, dicyclopentadiene type ethylene rhodanate resin or its combination.
5. a resin molding infiltration process is characterized in that step comprises with the preparation method of resin:
1) by weight,, obtains prepolymer with 100 parts of bimaleimide resins and 50～90 parts of diallyl phenyl compounds prepolymerization reaction 30～60 minutes under 120～140 ℃ temperature condition;
2) treat that prepolymer is cooled to 100～120 ℃ after, add 20～300 parts cyanate ester resin, pre-polymerization is 30～60 minutes under 100～120 ℃ temperature condition, obtains bismaleimide-triazine resin;
3) 10～50 parts hyperbranched polyorganosiloxane is joined in the above-mentioned bismaleimide-triazine resin, under 80～100 ℃ temperature condition, reacted 20～200 minutes, obtain a kind of resin molding infiltration process resin.
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| CN101824148A (en) * | 2010-04-13 | 2010-09-08 | 苏州大学 | Bismaleimide-triazine resin and preparation method thereof |
| CN101974226A (en) * | 2010-11-11 | 2011-02-16 | 苏州大学 | Flame-retardant bismaleimide resin and preparation method thereof |
| CN101775139B (en) * | 2009-12-31 | 2012-02-01 | 苏州大学 | Method for preparing modified bismaleimide resin |
| CN102643543A (en) * | 2011-02-18 | 2012-08-22 | 中国科学院深圳先进技术研究院 | Composite dielectric material, copper-clad foil prepreg manufactured and copper-clad foil laminated board by using composite dielectric material |
| CN104830059A (en) * | 2015-05-22 | 2015-08-12 | 苏州生益科技有限公司 | Resin composition and prepreg laminated board manufactured by employing same |
| CN105199297A (en) * | 2015-10-13 | 2015-12-30 | 湖北三江航天江北机械工程有限公司 | Bismaleimide resin premix with good dielectric property as well as preparation method and device of bismaleimide resin premix |
| WO2018025921A1 (en) * | 2016-08-05 | 2018-02-08 | 日本化薬株式会社 | Maleimide resin composition, prepreg, cured product of same and semiconductor device |
| JP2019089929A (en) * | 2017-11-14 | 2019-06-13 | 三菱瓦斯化学株式会社 | Resin composition, prepreg, metal foil-clad laminate, resin sheet and printed wiring board |
| CN110372861A (en) * | 2019-06-27 | 2019-10-25 | 扬州天启新材料股份有限公司 | The preparation method of modification dicyclopentadiene type ethylene rhodanate resin with agent of low hygroscopicity |
| CN114685988A (en) * | 2020-12-29 | 2022-07-01 | 洛阳尖端技术研究院 | Modified bismaleimide resin and preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1213084C (en) * | 2003-08-19 | 2005-08-03 | 梁国正 | Preparation method and application of modified double maleimide resin |
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- 2009-07-02 CN CN2009101813499A patent/CN101613531B/en not_active Expired - Fee Related
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| CN101775139B (en) * | 2009-12-31 | 2012-02-01 | 苏州大学 | Method for preparing modified bismaleimide resin |
| CN101824148A (en) * | 2010-04-13 | 2010-09-08 | 苏州大学 | Bismaleimide-triazine resin and preparation method thereof |
| CN101974226A (en) * | 2010-11-11 | 2011-02-16 | 苏州大学 | Flame-retardant bismaleimide resin and preparation method thereof |
| CN101974226B (en) * | 2010-11-11 | 2012-09-12 | 苏州大学 | Flame-retardant bismaleimide resin and preparation method thereof |
| CN102643543A (en) * | 2011-02-18 | 2012-08-22 | 中国科学院深圳先进技术研究院 | Composite dielectric material, copper-clad foil prepreg manufactured and copper-clad foil laminated board by using composite dielectric material |
| CN102643543B (en) * | 2011-02-18 | 2014-09-17 | 中国科学院深圳先进技术研究院 | Composite dielectric material, copper-clad foil prepreg manufactured and copper-clad foil laminated board by using composite dielectric material |
| CN104830059A (en) * | 2015-05-22 | 2015-08-12 | 苏州生益科技有限公司 | Resin composition and prepreg laminated board manufactured by employing same |
| CN105199297A (en) * | 2015-10-13 | 2015-12-30 | 湖北三江航天江北机械工程有限公司 | Bismaleimide resin premix with good dielectric property as well as preparation method and device of bismaleimide resin premix |
| WO2018025921A1 (en) * | 2016-08-05 | 2018-02-08 | 日本化薬株式会社 | Maleimide resin composition, prepreg, cured product of same and semiconductor device |
| CN109563344A (en) * | 2016-08-05 | 2019-04-02 | 日本化药株式会社 | Maleimide resin composition, prepreg, its hardening thing and semiconductor device |
| JPWO2018025921A1 (en) * | 2016-08-05 | 2019-06-20 | 日本化薬株式会社 | Maleimide resin composition, prepreg, cured product thereof and semiconductor device |
| JP2019089929A (en) * | 2017-11-14 | 2019-06-13 | 三菱瓦斯化学株式会社 | Resin composition, prepreg, metal foil-clad laminate, resin sheet and printed wiring board |
| JP6994174B2 (en) | 2017-11-14 | 2022-01-14 | 三菱瓦斯化学株式会社 | Resin composition, prepreg, metal foil-clad laminate, resin sheet and printed wiring board |
| CN110372861A (en) * | 2019-06-27 | 2019-10-25 | 扬州天启新材料股份有限公司 | The preparation method of modification dicyclopentadiene type ethylene rhodanate resin with agent of low hygroscopicity |
| CN110372861B (en) * | 2019-06-27 | 2020-04-28 | 扬州天启新材料股份有限公司 | Preparation method of modified dicyclopentadiene type cyanate ester resin with low hygroscopicity |
| CN114685988A (en) * | 2020-12-29 | 2022-07-01 | 洛阳尖端技术研究院 | Modified bismaleimide resin and preparation method and application thereof |
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