CN105176005A - Low-water-absorptivity dicyandiamide-curing epoxy composite - Google Patents
Low-water-absorptivity dicyandiamide-curing epoxy composite Download PDFInfo
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- CN105176005A CN105176005A CN201510698495.4A CN201510698495A CN105176005A CN 105176005 A CN105176005 A CN 105176005A CN 201510698495 A CN201510698495 A CN 201510698495A CN 105176005 A CN105176005 A CN 105176005A
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Abstract
The invention discloses a low-water-absorptivity dicyandiamide-curing epoxy composite is prepared by the comprising the following steps: adding an organosilicon modified epoxy compound with 3-10 epoxy groups into a single-component epoxy resin system, and mixing to react. The mass ratio of the organosilicon modified epoxy compound to the resin in the single-component epoxy resin system is (0.1-10):100. The added compound can greatly lower the water absorptivity of the dicyandiamide-curing epoxy composite; and the core-shell toughening rubber, wetting agent and reactive dehydrator, which do not influence the heat resistance, are used as auxiliary materials to greatly enhance the bonding property of the dicyandiamide-curing system in the damp heat state, enhance the water resistance of the bonding, packaging and coating materials and improve the electric properties and bonding properties.
Description
Technical field
Embodiments of the present invention relate to the field of epoxy resin composite formulating of recipe, more specifically, embodiments of the present invention relate to the adhesiveproperties after a kind of solidification and wet-heat resisting ability strong, be particularly suitable for being applied in the low water absorption dicyandiamide cure epoxy cpd in field of more severe (high pressure, high temperature and the high humidity) adhering with epoxy resin of environment for use, encapsulation and coating.
Background technology
It is good that Dyhard RU 100 has middle low-temperature storage as the solidifying agent of epoxy resin, and high temperature can quick-setting advantage, is widely used in that electronics is bonding, encapsulation and coating industry.But Dyhard RU 100 is due to itself structure, the easy moisture absorption, and the material after solidification has higher water-intake rate.
In general, under high temperature, high humidity or condition of high voltage, after curable epoxide, the water-intake rate of material can sharply raise, and water-intake rate is higher except affecting except electrical property, also may because bonding decline (as Fig. 1) under high temperature, high humidity or high pressure conditions, steam is caused easily to infiltrate from bonding interface and cured article surface, materials water-resistant declines, and occurs as corrosion chip, affects the results such as bonding, have a strong impact on material property.
So, have in the electronic product of requirement at some will have strict control to water-intake rate to hydrothermal aging.And if latent curing agent such as imidazoles or the modified amine of product are used alone as an alternative, water-intake rate can be relatively low, but this kind of material price is very expensive, often can only use as promotor, so people still more wish to be suitable for the higher dicyandiamide cure system of cost performance.Therefore, the water-intake rate how reducing dicyandiamide cure system has just become all the time very concerned topic, is subject to the extensive concern of industry.
Method common at present adds wetting agent or coupling agent carries out process to suppress water-intake rate to filler and solidifying agent, can play limited effect to a certain extent.But, in order to improve the water tolerance of the rear material of solidification further, just just must optimize from following three aspects: (1) improves the hydrophobic ability of system; (2) cross-linking density of cured article is improved; (3) the hydrolysis ability of system under high temperature is improved.
Summary of the invention
Instant invention overcomes the deficiencies in the prior art, a kind of low water absorption dicyandiamide cure epoxy cpd is provided, to expect to solve the high problem of dicyandiamide cure epoxy cpd water-intake rate.
For solving above-mentioned technical problem, one embodiment of the present invention by the following technical solutions:
A kind of low water absorption dicyandiamide cure epoxy cpd, it is the silicon-modified epoxy compound by adding in single component epoxy system containing 3 ~ 10 epoxy group(ing), then mixes, reacts and obtain.Silicon-modified epoxy compound and epoxy resin that the present invention uses have good consistency, can improve the cross-linking density of system, thermotolerance the surface energy that reduces, raising hydrophobicity, thus reduce the water-intake rate under damp and hot condition of high voltage after solidification.
Described silicon-modified epoxy compound is 0.1 ~ 10:100 with the resin quality ratio in single component epoxy system.
The synthetic method of described silicon-modified epoxy compound is:
Method a: hydrogeneous ring body or the viscosity at least containing 3 Si-H keys obtain described silicon-modified epoxy compound by addition reaction of silicon with hydrogen lower than the containing hydrogen silicone oil of 100cs and double bond containing active epoxy thinner under platinum complex katalysis, and the epoxy-functional number of this product is relevant with the molar ratio of the number of Si-H and active epoxy thinner; Described double bond containing active epoxy thinner can select glycidyl allyl ether or glycidyl methacrylate etc.;
Method b: vinyl ring body, octamethylcyclotetrasiloxane or viscosity obtain described silicon-modified epoxy compound by rearrangement reaction with the silane coupling agent of band epoxy group(ing) lower than the silicone oil of 100cs under acid catalysis, the epoxy-functional number of this product is relevant with the molar ratio of the silane coupling agent of band epoxy group(ing).
Above-mentioned viscosity is all silicone oil or the containing hydrogen silicone oil of short chain lower than the silicone oil of 100cs or containing hydrogen silicone oil.The technique effect that technical scheme of the present invention can not use full-bodied silicone oil or containing hydrogen silicone oil to reach identical.
Aforesaid method a and b is the synthetic route that those skilled in the art indicate silicon-modified epoxy compound, on this basis, they can obtain corresponding silicon-modified epoxy compound, herein without the need to limiting each raw-material consumption by regulating each raw-material consumption.
Described single component epoxy system comprises the following component by mass parts metering:
Resin 100 parts, 2 ~ 20 parts, solidifying agent, subsidence feed 0.1 ~ 15 part, toughner 0 ~ 20 part, wetting agent 0 ~ 5 part, response type water-removal agent 0 ~ 10 part, filler 0 ~ 500 part.
Described resin is bisphenol A epoxide resin, bisphenol F epoxy resin, phenol aldehyde modified epoxy resin, one or more in other epoxy prepolymers that can react with Dyhard RU 100.
Described solidifying agent is one or more in the cyanoguanidine derivative of Dyhard RU 100, modification.
Described subsidence feed is one or more in substituted urea, imidazoles or modified amine.
Described toughner is the particle modified rubber of nano core-shell, as polyhutadiene core shell rubbers, organosilicon core shell rubbers, butylbenzene core shell rubbers one or more.Although the particle modified toughner of nano core-shell directly can not play the effect reducing water-intake rate, the bonding effect with interface after mixture solidification can be improved, and minimizing stress.
Described wetting agent is BYK-337, BYK-333, BYK-310, BYK-320, BYK-330, BYK-306, BYK-307 of Bi Ke chemistry, one or more in Wet240, Wet250, Wet260, Wet265, Wet270, Wet280, Wet4000, Wet4100, WetKL245 of Tego.These wetting agents to reduce capillary auxiliary agent, the wetting capacity to base material can be improved, improve the bonding of interface, under avoiding high pressure, humid tropical condition, aqueous vapor is from contacting permeation, it can also move to cured article surface, improve the water contact angle of cured article, suppress steam toward the infiltration of cured article inside.Bi Ke chemistry, Tego refer to the Liang Jia chemical assistant company of Germany.
Described response type water-removal agent is one or more of silane coupling agent of band epoxy group(ing), as 3-(2,3 epoxy third oxygen) propyl trimethoxy silicane, 3-(2,3 epoxy third oxygen) propyl-triethoxysilicane, 3-(2,3 epoxy third oxygen) hydroxypropyl methyl diethoxy silane etc., response type water-removal agent can participate in the curing cross-linked of mixture.
Filler can carry out selecting and adding as required, can select one or more of silicon powder, calcium carbonate, aluminium hydroxide, aluminum oxide, white carbon black, wollastonite, kaolin, carbon black etc.Amount of colorant can also be added, as carbon black color paste.
Compared with prior art, one of beneficial effect of the present invention is: the present invention utilizes containing participating in single component epoxy system high-temperature solidification process compared with the silicon-modified epoxy compound of polyepoxy crosslinked, has the following advantages: (1) forms the infiltration that higher cross-linking density suppresses water molecules; (2) the Si-O structure after solidification, has better thermotolerance; (3) surface energy is lower, thus after solidification, the hydrophobicity of system is improved.As can be seen from above, adding of this compound allows the water-intake rate of dicyandiamide cure epoxy cpd significantly be reduced, and be aided with the nucleocapsid toughening rubber, wetting agent and the response type water-removal agent that do not affect thermotolerance simultaneously, bonding under humid tropical condition of dicyandiamide cure system can be improved to a greater extent, improve bonding, encapsulation, coating material water tolerance, improve its electrical property and adhesiveproperties.
Accompanying drawing explanation
Fig. 1 is the effect tendency string diagram that tensile shear strength is subject to temperature, humidity and pressure.
Embodiment
In order to make object of the present invention, technical scheme and advantage clearly understand, below in conjunction with drawings and Examples, the present invention is further elaborated.Should be appreciated that specific embodiment described herein only in order to explain the present invention, be not intended to limit the present invention.
First by the silicon-modified epoxy compound a of synthesis example 1 ~ 4 preparation containing 3 ~ 10 epoxy group(ing), b, c, d.
Synthesis example 1
Add 240g tetramethyl-hydrogen cyclotetrasiloxane 503g glycidyl allyl ether in a kettle., 0.5g platinum complex is added when stirring, be warmed up to 80 DEG C of reaction 5h, underpressure distillation subsequently removes unreacted raw material, obtains silicon-modified epoxy compound a.
Synthesis example 2
Add 35g vinyl ring body, 150g3-(2 in a kettle., 3 epoxy third oxygen) propyl trimethoxy silicane, the sulfonate resin of 2g drying is added when stirring, be warmed up to 80 DEG C of reaction 5h, underpressure distillation subsequently removes unreacted raw material, obtains silicon-modified epoxy compound b.
Synthesis example 3
Add 100g containing hydrogen silicone oil (Si-H bond number amount >=3 in a kettle., viscosity < 100cs), 40g glycidyl methacrylate, 0.5g platinum complex is added when stirring, be warmed up to 80 DEG C of reaction 5h, underpressure distillation subsequently removes unreacted raw material, obtains silicon-modified epoxy compound c.
Synthesis example 4
Add 30g octamethylcyclotetrasiloxane, 120g3-(2 in a kettle., 3 epoxy third oxygen) propyl-triethoxysilicane, the sulfonate resin of 2g drying is added when stirring, be warmed up to 80 DEG C of reaction 5h, underpressure distillation subsequently removes unreacted raw material, obtains silicon-modified epoxy compound d.
Adopt the silicon-modified epoxy compound of synthesis example 1 ~ 4 gained to prepare low water absorption dicyandiamide cure epoxy cpd below, and carry out performance test to it, the performance test results of each embodiment is in table 1.
Embodiment 1
E51 bisphenol A epoxide resin 50g is sequentially added in planet stirring, polyhutadiene core shell rubbers 5g, carbon black color paste 1g, Dyhard RU 100 6g, substituted urea 2g, silicon-modified epoxy compound a 5g, wetting agent (BYK-333) 0.2g, molten silicon micro mist 50g, 3-(2,3 epoxy third oxygen) propyl trimethoxy silicane 0.3g, obtain mixture after stirring 1h.
Embodiment 2
E51 bisphenol A epoxide resin 50g is sequentially added in planet stirring, polyhutadiene core shell rubbers 5g, carbon black color paste 1g, Dyhard RU 100 6g, substituted urea 2g, silicon-modified epoxy compound b5g, wetting agent (BYK-333) 0.2g, molten silicon micro mist 50g, 3-(2,3 epoxy third oxygen) propyl trimethoxy silicane 0.3g, obtain mixture after stirring 1h.
Embodiment 3
E51 bisphenol A epoxide resin 50g is sequentially added in planet stirring, polyhutadiene core shell rubbers 5g, carbon black color paste 1g, Dyhard RU 100 6g, substituted urea 2g, silicon-modified epoxy compound c5g, wetting agent (BYK-333) 0.2g, molten silicon micro mist 50g, 3-(2,3 epoxy third oxygen) propyl trimethoxy silicane 0.3g, obtain mixture after stirring 1h.
Embodiment 4
E51 bisphenol A epoxide resin 50g is sequentially added in planet stirring, polyhutadiene core shell rubbers 5g, carbon black color paste 1g, Dyhard RU 100 6g, substituted urea 2g, silicon-modified epoxy compound d5g, wetting agent (BYK-333) 0.2g, molten silicon micro mist 50g, 3-(2,3 epoxy third oxygen) propyl trimethoxy silicane 0.3g, obtain mixture after stirring 1h.
Comparative example 1
In planet stirring, be sequentially added into E51 bisphenol A epoxide resin 50g, polyhutadiene core shell rubbers 5g, carbon black color paste 1g, Dyhard RU 100 6g, substituted urea 2g, molten silicon micro mist 50g, after stirring 1h, obtain mixture.
Comparative example 2
E51 bisphenol A epoxide resin 50g is sequentially added in planet stirring, polyhutadiene core shell rubbers 5g, carbon black color paste 1g, Dyhard RU 100 6g, substituted urea 2g, wetting agent (BYK-333) 0.2g, molten silicon micro mist 50g, 3-(2,3 epoxy third oxygen) propyl trimethoxy silicane 0.3g, obtains mixture after stirring 1h.
Solidification and test condition:
Condition of cure: take 3.5g mixture, 120 DEG C of solidification 2h obtain cured article;
Steaming and decocting under high pressure condition: 2atm, 121 DEG C, boiling 8h;
Soak at room temperature condition: 25 DEG C, 24h.
The performance test results of table 1 each embodiment gained mixture
Remarks: testing method is that soak at room temperature or steaming and decocting under high pressure terminate rear taking-up, uses thieving paper wipe surfaces, carries out test of weighing within 10min.Weigh before soak at room temperature or steaming and decocting under high pressure and be denoted as m
1, weigh after soak at room temperature or steaming and decocting under high pressure and be denoted as m
2.
Water-intake rate=(m
2-m
1) × 100/m
1
Embodiment 1 ~ 4 is the formulas that with the addition of silicon-modified epoxy compound, and comparative example 1 does not have silicon-modified epoxy compound and without the formula of wetting agent and water-removal agent, comparative example 2 does not add organic-silicon-modified epoxy compounds, but have the formula without wetting agent and water-removal agent.
This patent is by as follows to the comparing result of embodiment and comparative example:
As can be seen from the data of table 1, by adding this series of material, the water-intake rate of dicyandiamide cure epoxy cpd can be reduced greatly, make it be more suitable for being applied in the field of more severe (high pressure, high temperature and the high humidity) adhering with epoxy resin of environment for use, encapsulation and coating.
Except above-described embodiment, following examples can also be adopted to prepare low water absorption dicyandiamide cure epoxy cpd.
Embodiment 5
In planet stirring, be sequentially added into bisphenol F epoxy resin 50g; butylbenzene core shell rubbers 3g; Dyhard RU 100 4g; substituted urea 6g, silicon-modified epoxy compound a 0.5g, wetting agent (Wet4100) 1g; kaolin 100g; 3-(2,3 epoxy third oxygen) hydroxypropyl methyl diethoxy silane 4g, after stirring 1h, obtain mixture.
Embodiment 6
In planet stirring, be sequentially added into phenol aldehyde modified epoxy resin 50g; butylbenzene core shell rubbers 3g; Dyhard RU 100 4g; substituted urea 6g, silicon-modified epoxy compound a 2g, wetting agent (BYK-320) 1g; carbon black 200g; 3-(2,3 epoxy third oxygen) hydroxypropyl methyl diethoxy silane 4g, after stirring 1h, obtain mixture.
Embodiment 5 ~ 6 gained meets the normal temperature water-intake rate of thing and high temperature steaming water-intake rate drops in the scope of embodiment 1 ~ 4.
Although with reference to multiple explanatory embodiment of the present invention, invention has been described here, but, should be appreciated that, those skilled in the art can design a lot of other amendment and embodiment, these amendments and embodiment will drop within spirit disclosed in the present application and spirit.More particularly, in scope disclosed in the present application, multiple modification and improvement can be carried out to the building block of subject combination layout and/or layout.Except the modification of carrying out building block and/or layout is with except improvement, to those skilled in the art, other purposes also will be obvious.
Claims (10)
1. a low water absorption dicyandiamide cure epoxy cpd, is characterized in that it is the silicon-modified epoxy compound by adding in single component epoxy system containing 3 ~ 10 epoxy group(ing), then mixing, react and obtain.
2. low water absorption dicyandiamide cure epoxy cpd according to claim 1, is characterized in that described silicon-modified epoxy compound is 0.1 ~ 10:100 with the resin quality ratio in single component epoxy system.
3. low water absorption dicyandiamide cure epoxy cpd according to claim 1, is characterized in that the synthetic method of described silicon-modified epoxy compound is:
Method a: hydrogeneous ring body or the viscosity at least containing 3 Si-H keys obtain described silicon-modified epoxy compound by addition reaction of silicon with hydrogen lower than the containing hydrogen silicone oil of 100cs and double bond containing active epoxy thinner under platinum complex katalysis;
Method b: vinyl ring body, octamethylcyclotetrasiloxane or viscosity obtain described silicon-modified epoxy compound by rearrangement reaction with the silane coupling agent of band epoxy group(ing) lower than the silicone oil of 100cs under acid catalysis.
4. low water absorption dicyandiamide cure epoxy cpd according to claim 1, is characterized in that described single component epoxy system comprises the following component by mass parts metering:
Resin 100 parts, 2 ~ 20 parts, solidifying agent, subsidence feed 0.1 ~ 15 part, toughner 0 ~ 20 part, wetting agent 0 ~ 5 part, response type water-removal agent 0 ~ 10 part, filler 0 ~ 500 part.
5. low water absorption dicyandiamide cure epoxy cpd according to claim 4, it is characterized in that described resin is bisphenol A epoxide resin, bisphenol F epoxy resin, phenol aldehyde modified epoxy resin, one or more in other epoxy prepolymers that can react with Dyhard RU 100.
6. low water absorption dicyandiamide cure epoxy cpd according to claim 4, is characterized in that described solidifying agent is one or more in the cyanoguanidine derivative of Dyhard RU 100, modification.
7. low water absorption dicyandiamide cure epoxy cpd according to claim 4, is characterized in that described subsidence feed is one or more in substituted urea, imidazoles or modified amine.
8. low water absorption dicyandiamide cure epoxy cpd according to claim 4, is characterized in that described toughner is the particle modified rubber of nano core-shell.
9. low water absorption dicyandiamide cure epoxy cpd according to claim 4, it is characterized in that described wetting agent is BYK-337, BYK-333, BYK-310, BYK-320, BYK-330, BYK-306, BYK-307 of Bi Ke chemistry, one or more in Wet240, Wet250, Wet260, Wet265, Wet270, Wet280, Wet4000, Wet4100, WetKL245 of Tego.
10. low water absorption dicyandiamide cure epoxy cpd according to claim 4, is characterized in that described response type water-removal agent is one or more of silane coupling agent of band epoxy group(ing).
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| CN111019577A (en) * | 2019-12-05 | 2020-04-17 | 杭州之江新材料有限公司 | Method for recovering performance of hot curing adhesive return material |
| CN112724896A (en) * | 2020-12-21 | 2021-04-30 | 东风汽车集团有限公司 | Structural adhesive with excellent moisture and heat resistance and preparation method thereof |
| CN113105864A (en) * | 2021-03-01 | 2021-07-13 | 华南理工大学 | Epoxy modified organic silicon gel and preparation method and application thereof |
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| CN107652933A (en) * | 2017-10-25 | 2018-02-02 | 绵阳惠利电子材料有限公司 | Magnetic core bonding nanoscale one-component tough epoxy compound and preparation method thereof |
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| CN111019577A (en) * | 2019-12-05 | 2020-04-17 | 杭州之江新材料有限公司 | Method for recovering performance of hot curing adhesive return material |
| CN111019577B (en) * | 2019-12-05 | 2021-04-02 | 杭州之江新材料有限公司 | Method for recovering performance of hot curing adhesive return material |
| CN112724896A (en) * | 2020-12-21 | 2021-04-30 | 东风汽车集团有限公司 | Structural adhesive with excellent moisture and heat resistance and preparation method thereof |
| CN112724896B (en) * | 2020-12-21 | 2022-06-07 | 东风汽车集团有限公司 | Structural adhesive with excellent moisture and heat resistance and preparation method thereof |
| CN113105864A (en) * | 2021-03-01 | 2021-07-13 | 华南理工大学 | Epoxy modified organic silicon gel and preparation method and application thereof |
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