CN104893649A - Heat-resistant solid composite adhesive - Google Patents
Heat-resistant solid composite adhesive Download PDFInfo
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- CN104893649A CN104893649A CN201510381243.9A CN201510381243A CN104893649A CN 104893649 A CN104893649 A CN 104893649A CN 201510381243 A CN201510381243 A CN 201510381243A CN 104893649 A CN104893649 A CN 104893649A
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Abstract
The invention relates to a heat-resistant solid composite adhesive. The heat-resistant solid composite adhesive is prepared from raw materials namely polyimide resin powder, stuffing, a silane coupling agent, a cyanate ester resin prepolymer, an epoxy resin prepolymer, silica sol, thioacetamide, a dispersing agent, succinic anhydride and zinc nitrate hexahydrate according to a mass ratio of 100:(20-37):(8-10):(25-32):(21-32):(25-36):(6-8):(2-3):(13-21):(2-5). The heat-resistant solid adhesive disclosed by the invention is reasonable in composition, all components are well compatible, the heat-resistant solid composite adhesive prepared thereby has excellent oxidation resistance and flame resistance and particularly has excellent mechanical property and heat resistance, and requirements on development and application of the heat-resistant solid composite adhesive are met.
Description
Technical field
The invention belongs to advanced composite material technical field, be specifically related to a kind of refractory solid composite gum.
Background technology
Material is the pillar of modern science and technology and social development, and the competition of modern high technology depends on the development of Materials science to a great extent.To material, particularly to the level of understanding of high performance material, grasp and application power, directly embodying scientific and technological level and the economic strength of country, is also the mark of a national overall national strength and civilization and progress speed.Therefore, the exploitation of novel material is the guide that Materials science develops with research, is the foundation stone of 21st century six large high-tech area.Matrix material is type material, because it is fire-retardant, intensity is high, rigidity is large, lightweight, can design, diversified function and the outstanding performance such as antifatigue, high temperature resistant, vibration damping, be used widely in fields such as the Aeronautics and Astronautics over nearly 30 years, the energy, traffic, machinery, building, chemical industry, biomedicine and physical culture, 21 century Material Field opened one's arms and met the arrival in matrix material epoch.Along with matrix material development and application, matrix material has been formed in the middle of network penetration to industry-by-industry field.
First the development of solid glue stick starts from abroad, so far the history in existing more than 70 years.Initial solid glue stick development is the solidification of liquid-type tackiness agent, allows tackiness agent use in solid form exactly.Deepening continuously and developing along with research, also regenerates in continuous renewal as bonding tackiness agent.Through the development of decades, the investigation and application technology comparative maturity of external solid glue stick, some companies have the solid gums product-feed of the multiple trade mark.
Solid glue stick is also known as solid glue, and compared with liquid glue water, solid glue stick is not only easy to carry, and does not trickle, tack-free, therefore well received.Traditional solid glue stick be a kind of with gelatin, gelatin antithrombotics, soap, solvent, sanitas for main raw material, add the material of some easy coagulation forming again as gelifying agent, add wetting Agent for Printing Inks, softening agent and flavouring agent again, to improve the performance of the aspects such as its use, storage, smell and outward appearance, above-mentioned various raw material is fully mixed through certain technique by selected formula, disperse equal Uniform after to reinject cooling forming in Lipstick-type packaging vessel, the product finally obtained.Solid glue stick can for pasting various paper in-20 DEG C to 40 DEG C environment.
Generally use polyvinylpyrrolidone as tackiness agent in the world, the glue rod made can provide enough physical strengths.On this basis, someone utilizes water-soluble polymers as tackiness agent, and soap glue, as excipient, have developed a kind of solid glue stick, has stronger adhesiveproperties and physical strength.Except main gel and gelifying agent, some auxiliary agents can also be added to improve the performance of solid glue stick.The kind aspect of external interpolation auxiliary agent is more domestic will be enriched many, and the glue rod properties therefore made is also just more superior.The auxiliary agent abroad used includes thickening material, sanitas, pigment, filler, essence, antioxidant, resin, dextrin, Mierocrystalline cellulose, starch derivative etc., and graphite, talcum, polymolecularity silicon soil, colloidal substance clay, silicon ore, chalk, magnesium oxide and glass fibre etc. wherein can be used as pigment and filler.A kind of solid glue stick that Germany develops, no matter all very superior in outward appearance or performance, this product appearance is transparent, the pure white exquisiteness of quality, hardness is moderate, and just the sticky time is short, and bounding force is strong, stringiness and moisture retention good, after ambient temperatare puts 1 year, still there is very strong bonding force and moisture retention.
The research of domestic solid glue stick is started late, and develops also slower.Current domestic be mainly devoted to research use various different starting material as the tackiness agent of solid glue stick, reach best effects to making the over-all properties of solid glue stick.Although polyvinylpyrrolidone is fine as the tackiness agent effect of solid glue stick, not soluble in water, cost is higher, is also unfavorable for environmental protection simultaneously.Although the solid glue stick cost using polyimide resin powder-aqueous polyvinyl acetate emulsion to make is lower, but this type of glue rod quality is fineless and smooth, and period of storage is short, and in the short period of time, (about once week) forms thin film on the surface of glue rod, have impact on use coating, practicality is little.Long for although master makes solid glue stick period of storage with the water-soluble polymers one soap class solid agent of acyl acid anhydride base, just the sticky time is long, and cost is also high.In order to improve the quality of products further, reduce selling price, meeting the need of market, many experts and technician are by great many of experiments, and it is good to have made viscosity, and the smooth exquisiteness of colloid, is coated with the glue rod of equal Uniform.Such as the moon and equality are using polyimide resin powder formal glue as tackiness agent, by sodium stearate as excipient, and in colloid, add various indicator, make the solid glue stick in various bright-colored, outward appearance is fine and smooth, and hardness is moderate, smears equal Uniform and lubricates, high and the speed of bonding strength fast (Zhejiang chemical industry .2005,36 (1): 23-25).
Prepare the solid glue stick having more premium properties, give full play to the functional of glue rod, also need to find more suitable raw material and auxiliary agent, and determine its optimum formula and reaction conditions, and wherein most importantly select suitable, there is functional tackiness agent.As the main component of solid glue stick, the selection of tackiness agent is vital.Bonding force should be selected strong, have stronger dissemination or water-soluble to glassware for drinking water, and be easy to spreadable organic high molecular compound as tackiness agent.Solid glue stick tackiness agent conventional both at home and abroad at present has Walocel MT 20.000PV, polyvinylpyrrolidone (PVP), polyimide resin powder formal, macromolecule resin mixture, starch, gelatine or gelatin etc.In these raw materials, the sticky paper effect of polyvinylpyrrolidone is fine, but not soluble in water, is soluble in organic solvent, makes its cost higher; Although starch, gelatine etc. are inexpensive, apt to deteriorate, thermo-labile; And the glue rod quality that existing raw material obtains is fineless and smooth, have impact on coating during use, and non-refractory, functional difference.
Summary of the invention
The object of this invention is to provide a kind of refractory solid composite gum, it is excellent that it has excellent adhesiveproperties, particularly thermal characteristics, still bonding under the high temperature conditions.
To achieve the above object of the invention, the technical solution used in the present invention is: a kind of refractory solid composite gum, makes by after organic-inorganic composite body mold pressing; Described organic-inorganic composite body is 100 by mass ratio: (20 ~ 37): (8 ~ 10): (25 ~ 32): (21 ~ 32): (25 ~ 36): (6 ~ 8): (2 ~ 3): (13 ~ 21): the polyimide resin powder of (2 ~ 5), filler, silane coupling agent, cyanate ester resin prepolymer, epoxy prepolymer, silicon sol, thioacetamide, dispersion agent, Succinic anhydried, zinc nitrate hexahydrate are that raw material obtains;
Described filler is prepared by with under type: be 10: after (50 ~ 55) mix in mass ratio by silicon carbide, oyster shell whiting, at 700 DEG C of sintering 6h in retort furnace, obtains solid; Then cross 200 mesh sieves after being pulverized by described solid, extracting screen underflow is filler;
The molecular weight of described polyimide resin powder is 3000 ~ 5000;
Described cyanate ester resin prepolymer molecular weight is 1800 ~ 3000;
Described epoxy prepolymer molecular weight is 4800 ~ 6500;
Described dispersion agent is sulfuric acid ester dispersion agent.
In the present invention, described silane coupling agent is KH550 or KH560.
In the present invention, cyanate ester resin is bisphenol A cyanate ester resin, bonding, reactive good; Epoxy resin is four-functional group epoxy resin, such as AG-80 or JD-919, and thermotolerance is better, reactive strong, good stability.
In the present invention, in silicon sol, solid content is 45 ~ 50%; The particle diameter of silicon-dioxide is 150 ~ 430 nanometers.Silicon sol is not only beneficial to the dispersion of system, increases the normal temperature cementability of solid gums, absorbing heat by when high temperature, prevents glue to lose efficacy, increases the reactivity of system simultaneously.
Preferably, described organic-inorganic composite body is 100 by mass ratio: (25 ~ 30): (8 ~ 9): (28 ~ 30): (25 ~ 28): (30 ~ 32): 7: 2: (15 ~ 16): the polyimide resin powder of (3 ~ 4), filler, silane coupling agent, cyanate ester resin prepolymer, epoxy prepolymer, silicon sol, thioacetamide, dispersion agent, Succinic anhydried, zinc nitrate hexahydrate are that raw material obtains.
In the present invention, organic object is the primary bond composition of solid gums, the molecular weight of polyimide resin powder is 3000 ~ 5000, cyanate ester resin prepolymer molecular weight is 1800 ~ 3000, epoxy prepolymer molecular weight is 4800 ~ 6500, the bonding force that molecular weight shows for solid gums has material impact, in particular concerns the high temperature bonding of solid gums; Low filmogen rate of drying is comparatively slow, and high resin system is not good to the wettability of inorganic filler.Organic-compound system of the present invention not only has the function of effectively solidification at normal temperatures, and can not melt during high temperature and cause adhesive failure.
In the present invention, described dispersion agent is sulfuric acid ester dispersion agent, the model that such as German Bi Ke company produces is the product of BYK170, BYK161, BYK110, these dispersion agents are the high molecular weight block copolymer solution containing filler affinity groups, its effect is that dispersed those are difficult to be dissolved in the solid particulate of liquid, also can prevent sedimentation and the cohesion of solid particulate simultaneously; There is filler affinity groups, improve filler and soak, also make filler dispersion stable dispersion by space stability ultimate load effect.
In the present invention, by cyanate resin alicyclic monomer in 95 DEG C of reactions 15 ~ 20 minutes, obtain cyanate ester resin prepolymer; By epoxy monomer in 150 DEG C of reactions 25 ~ 40 minutes, obtain epoxy prepolymer; Filler, silane coupling agent, silicon sol are mixed, obtains mixture; Successively thioacetamide, dispersion agent, Succinic anhydried, polyimide resin powder are added in mixture, stir 1 ~ 2 hour, then add cyanate ester resin prepolymer, epoxy prepolymer, stir 1.5 ~ 2 hours in 80 ~ 90 DEG C; Finally add zinc nitrate hexahydrate, stir 2 ~ 3 hours in 50 ~ 60 DEG C, obtain organic-inorganic composite body; Again organic-inorganic composite body is inserted in mould, cold pressing (pressure of colding pressing is 0.2 ~ 0.3MPa); Temperature is room temperature, namely obtains high temperature resistant solid gums.
Because technique scheme is used, the present invention compared with prior art has following advantages:
1. the organic-inorganic composite body that the present invention utilizes forms rationally, between each component, consistency is good, has prepared refractory solid composite gum thus, has good oxidation-resistance, adhesiveproperties, there is excellent resistance toheat especially, meet the development and application of refractory solid composite gum.
2. disclosed by the inventionly prepare in refractory solid composite gum raw material, raw material is simple and easy to get, and without the need to the complex reaction of prior art, the refractory solid composite gum of preparation has excellent adhesiveproperties, ambient cure is effective, when being heated, filler increases the thermal characteristics of system on the one hand, on the other hand silicon sol and the slow dehydration of zinc nitrate hexahydrate, catalyzing organic reacts further, form stable structure, high temperature bonding stability is strong, achieves beyond thought effect; And avoid solid gums melted by heat in prior art and cause the defect of adhesive failure.
Embodiment
Below in conjunction with embodiment, the invention will be further described:
Embodiment one
After 100g silicon carbide, 500g oyster shell whiting being mixed, at 700 DEG C of sintering 6h in retort furnace, obtain solid; Then cross 200 mesh sieves after being pulverized by described solid, extracting screen underflow is filler; By bisphenol A cyanate ester resin monomer in 95 DEG C of reactions 15 minutes, obtain cyanate ester resin prepolymer (molecular weight is 1800 ~ 2200); By epoxy resin AG-80 monomer in 150 DEG C of reactions 25 minutes, obtain epoxy prepolymer (molecular weight is 4800 ~ 5500); By 30g silicon sol, (solid content is 45%; The particle diameter of silicon-dioxide is 150 ~ 260 nanometers), 25g filler, 8g Silane coupling agent KH550 mix 1 hour, obtains mixture; Successively 7g thioacetamide, 2g dispersant B YK170,16g Succinic anhydried, 100g polyimide resin powder (molecular weight 3000 ~ 4000) are added in mixture, stir 1 hour, then add 28g cyanate ester resin prepolymer, 28g epoxy prepolymer, stir 1.5 hours in 80 DEG C; Finally add 3g zinc nitrate hexahydrate, stir 2 hours in 50 DEG C, obtain organic-inorganic composite body; Insert in mould by organic-inorganic composite body again, room temperature mold pressing (molding pressure is 0.2MPa), namely obtains refractory solid composite gum.
Embodiment two
The filler of Example one; By bisphenol A cyanate ester resin monomer in 95 DEG C of reactions 20 minutes, obtain cyanate ester resin prepolymer (molecular weight is 2400 ~ 3000); By epoxy resin AG-80 monomer in 150 DEG C of reactions 30 minutes, obtain epoxy prepolymer (molecular weight is 5800 ~ 6500); By 32g silicon sol, (solid content is 50%; The particle diameter of silicon-dioxide is 250 ~ 360 nanometers), 30g filler, 9g silane coupling agent KH560 mix 1 hour, obtains mixture; Successively 7g thioacetamide, 2g dispersant B YK161,15g Succinic anhydried, 100g polyimide resin powder (molecular weight 3500 ~ 4300) are added in mixture, stir 1 hour, then add 30g cyanate ester resin prepolymer, 25g epoxy prepolymer, stir 1.5 hours in 80 DEG C; Finally add 4g zinc nitrate hexahydrate, stir 2 hours in 50 DEG C, obtain organic-inorganic composite body; Insert in mould by organic-inorganic composite body again, room temperature mold pressing (molding pressure is 0.2MPa), namely obtains refractory solid composite gum.
Embodiment three
The filler of Example one; By bisphenol A cyanate ester resin monomer in 95 DEG C of reactions 18 minutes, obtain cyanate ester resin prepolymer (molecular weight is 2200 ~ 2800); By epoxy resin JD-919 monomer in 150 DEG C of reactions 27 minutes, obtain epoxy prepolymer (molecular weight is 5200 ~ 6100); By 31g silicon sol, (solid content is 47%; The particle diameter of silicon-dioxide is 280 ~ 330 nanometers), 27g filler, 9g Silane coupling agent KH550 be uniformly mixed 2 hours, obtains mixture; Successively 7g thioacetamide, 2g dispersant B YK110,16g Succinic anhydried, 100g polyimide resin powder (molecular weight 3900 ~ 4800) are added in mixture, stir 1 hour, then add 28g cyanate ester resin prepolymer, 27g epoxy prepolymer, stir 2 hours in 90 DEG C; Finally add 4g zinc nitrate hexahydrate, stir 3 hours in 60 DEG C, obtain organic-inorganic composite body; Insert in mould by organic-inorganic composite body again, room temperature mold pressing (molding pressure is 0.3MPa), namely obtains refractory solid composite gum.
Embodiment four
After 100g silicon carbide, 550g oyster shell whiting being mixed, at 750 DEG C of sintering 7h in retort furnace, obtain solid; Then cross 200 mesh sieves after being pulverized by described solid, extracting screen underflow is filler; By bisphenol A cyanate ester resin monomer in 95 DEG C of reactions 20 minutes, obtain cyanate ester resin prepolymer (molecular weight is 2400 ~ 3000); By epoxy resin AG-80 monomer in 150 DEG C of reactions 30 minutes, obtain epoxy prepolymer (molecular weight is 5800 ~ 6500); By 36g silicon sol, (solid content is 48%; The particle diameter of silicon-dioxide is 350 ~ 400 nanometers), 37g filler, 10g silane coupling agent KH560 mix 2 hours, obtains mixture; Successively 8g thioacetamide, 3g dispersant B YK110,20g Succinic anhydried, 100g polyimide resin powder (molecular weight 4500 ~ 5000) are added in mixture, stir 1 hour, then add 25g cyanate ester resin prepolymer, 32g epoxy prepolymer, stir 1.5 hours in 90 DEG C; Finally add 5g zinc nitrate hexahydrate, stir 3 hours in 50 DEG C, obtain organic-inorganic composite body; Insert in mould by organic-inorganic composite body again, room temperature mold pressing (molding pressure is 0.2MPa), namely obtains refractory solid composite gum.
Embodiment five
The filler of Example four; By bisphenol A cyanate ester resin monomer in 95 DEG C of reactions 16 minutes, obtain cyanate ester resin prepolymer (molecular weight is 1900 ~ 2200); By epoxy resin JD-919 monomer in 150 DEG C of reactions 28 minutes, obtain epoxy prepolymer (molecular weight is 5500 ~ 6100); By 25g silicon sol, (solid content is 46%; The particle diameter of silicon-dioxide is 310 ~ 370 nanometers), 35g filler, 8g Silane coupling agent KH550 mix 2 hours, obtains mixture; Successively 6g thioacetamide, 2g dispersant B YK161,14g Succinic anhydried, 100g polyimide resin powder (molecular weight 4500 ~ 5000) are added in mixture, stir 1 hour, then add 32g cyanate ester resin prepolymer, 21g epoxy prepolymer, stir 2 hours in 90 DEG C; Finally add 2g zinc nitrate hexahydrate, stir 3 hours in 50 DEG C, obtain organic-inorganic composite body; Insert in mould by organic-inorganic composite body again, room temperature mold pressing (molding pressure is 0.2MPa), namely obtains refractory solid composite gum.
Comparative example one
The filler of Example four; By bisphenol A cyanate ester resin monomer in 105 DEG C of reactions 40 minutes, obtain cyanate ester resin prepolymer (molecular weight is 4900 ~ 5200); By epoxy resin JD-919 monomer in 150 DEG C of reactions 50 minutes, obtain epoxy prepolymer (molecular weight is 9500 ~ 11100); 35g filler, 8g Silane coupling agent KH550 are mixed 2 hours, obtains mixture; Successively 6g thioacetamide, 2g dispersant B YK161,14g Succinic anhydried are added in mixture, stir 1 hour, then add 32g cyanate ester resin prepolymer, 21g epoxy prepolymer, stir 2 hours in 90 DEG C; Finally add 100g polyvinyl alcohol, 2g zinc nitrate hexahydrate, stir 3 hours in 50 DEG C, obtain organic-inorganic composite body; Insert in mould by organic-inorganic composite body again, room temperature mold pressing (molding pressure is 0.2MPa), namely obtains solid composite gum.
Comparative example two
The filler of Example one; By bisphenol A cyanate ester resin monomer in 95 DEG C of reactions 16 minutes, obtain cyanate ester resin prepolymer (molecular weight is 1900 ~ 2200); By epoxy resin JD-919 monomer in 150 DEG C of reactions 28 minutes, obtain epoxy prepolymer (molecular weight is 5500 ~ 6100); By 25g silicon sol, (solid content is 46%; The particle diameter of silicon-dioxide is 310 ~ 370 nanometers), 35g filler mixes 2 hours, obtains mixture; Successively 6g thioacetamide, 2g dispersant B YK161 are added in mixture, stir 1 hour, then add 32g cyanate ester resin prepolymer, 21g epoxy prepolymer, stir 2 hours in 90 DEG C; Finally add 100g polyvinylpyrrolidone, stir 3 hours in 50 DEG C, obtain organic-inorganic composite body; Insert in mould by organic-inorganic composite body again, room temperature mold pressing (molding pressure is 0.2MPa), namely obtains solid composite gum.
Performance test
Utilize dimension card thermal distortion instrument test heat-drawn wire (CTE/ DEG C); Electronic universal tester is utilized to test flexural strength (Rt/MPa); Liquid crystal type balance weight impact testing machine is utilized to test shock strength (α/KJ/m
2); Adopt dynamic mechanical test instrument test storage modulus (E/MPa(35 DEG C)); Utilize 3M 600 adhesive tape, drawing coating test sticking power; In 200 heating 2 minutes, test sticking power R; Hot weightless instrument is utilized to test temperature of initial decomposition (T
0/ DEG C).
The performance test results of above-mentioned composite solid gum is in table 1.
The performance of table 1 solid gums
| CTE | α | Rt | Sticking power | Sticking power R | E | T 0 | |
| Embodiment one | 205 | 4.1 | 73 | >5B | 5B | 980 | 401 |
| Embodiment two | 201 | 3.9 | 70 | >5B | 5B | 970 | 394 |
| Embodiment three | 199 | 3.8 | 74 | >5B | 5B | 960 | 397 |
| Embodiment four | 200 | 3.9 | 76 | >5B | 5B | 984 | 390 |
| Embodiment five | 203 | 4 | 69 | >5B | 5B | 972 | 396 |
| Comparative example one | 160 | 2.7 | 39 | 4B | - | 741 | 317 |
| Comparative example two | 128 | 1.8 | 30 | 4B | - | 694 | 221 |
To sum up, rationally, between each component, consistency is good for refractory solid glue composition disclosed by the invention, prepare refractory solid composite gum thus, there is good oxidation-resistance, flame retardant properties, there is excellent mechanical property, resistance toheat especially, meet the development and application of refractory solid composite gum.
Claims (7)
1. a refractory solid composite gum, is characterized in that: make by after organic-inorganic composite body mold pressing; Described organic-inorganic composite body is 100 by mass ratio: (20 ~ 37): (8 ~ 10): (25 ~ 32): (21 ~ 32): (25 ~ 36): (6 ~ 8): (2 ~ 3): (13 ~ 21): the polyimide resin powder of (2 ~ 5), filler, silane coupling agent, cyanate ester resin prepolymer, epoxy prepolymer, silicon sol, thioacetamide, dispersion agent, Succinic anhydried, zinc nitrate hexahydrate are that raw material obtains;
Described filler is prepared by with under type: be 10: after (50 ~ 55) mix in mass ratio by silicon carbide, oyster shell whiting, at 700 ~ 800 DEG C of sintering 6 ~ 8h in retort furnace, obtains solid; Then cross 750 ~ 800 mesh sieves after being pulverized by described solid, extracting screen underflow is filler;
The molecular weight of described polyimide resin powder is 3000 ~ 5000;
Described cyanate ester resin prepolymer molecular weight is 1800 ~ 3000;
Described epoxy prepolymer molecular weight is 4800 ~ 6500;
Described dispersion agent is sulfuric acid ester dispersion agent.
2. refractory solid composite gum according to claim 1, is characterized in that: described cyanate ester resin is bisphenol A cyanate ester resin; Epoxy resin is four-functional group epoxy resin.
3. refractory solid composite gum according to claim 1, is characterized in that: described silane coupling agent is KH550 or KH560.
4. refractory solid composite gum according to claim 1, is characterized in that: in described silicon sol, solid content is 45 ~ 50%; The particle diameter of silicon-dioxide is 150 ~ 430 nanometers.
5. refractory solid composite gum according to claim 1, is characterized in that: described organic-inorganic composite body is 100 by mass ratio: (25 ~ 30): (8 ~ 9): (28 ~ 30): (25 ~ 28): (30 ~ 32): 7: 2: (15 ~ 16): the polyimide resin powder of (3 ~ 4), filler, silane coupling agent, cyanate ester resin prepolymer, epoxy prepolymer, silicon sol, thioacetamide, dispersion agent, Succinic anhydried, zinc nitrate hexahydrate are that raw material obtains.
6. refractory solid composite gum according to claim 1, is characterized in that: described cyanate ester resin prepolymer is obtained in 95 DEG C of reactions by cyanate resin alicyclic monomer for 15 ~ 20 minutes; Described epoxy prepolymer is obtained in 150 DEG C of reactions by epoxy monomer for 25 ~ 40 minutes.
7. refractory solid composite gum according to claim 1, is characterized in that: the particle diameter of described silicon carbide is 0.5 ~ 1.5 micron; The particle diameter of described oyster shell whiting is 0.8 ~ 1.6 micron.
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| CN106190006A (en) * | 2016-08-23 | 2016-12-07 | 苏州盛达胶粘制品有限公司 | A kind of reinforced polyimides adhesive |
| WO2017153576A1 (en) * | 2016-03-11 | 2017-09-14 | Epg (Engineered Nanoproducts Germany) Ag | Materials for use as adhesive and for surface sealing |
| US20220049056A1 (en) * | 2020-08-17 | 2022-02-17 | Baker Hughes Oilfield Operations Llc | Manufacture of degradable polycyanurate bulk molding compositions |
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| US11767400B2 (en) * | 2020-08-17 | 2023-09-26 | Baker Hughes Oilfield Operations Llc | Manufacture of degradable polycyanurate bulk molding compositions |
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