CN102260480A - High-temperature-resistant modified epoxy resin adhesive and preparation method thereof - Google Patents
High-temperature-resistant modified epoxy resin adhesive and preparation method thereof Download PDFInfo
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- CN102260480A CN102260480A CN2011101955124A CN201110195512A CN102260480A CN 102260480 A CN102260480 A CN 102260480A CN 2011101955124 A CN2011101955124 A CN 2011101955124A CN 201110195512 A CN201110195512 A CN 201110195512A CN 102260480 A CN102260480 A CN 102260480A
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Abstract
The invention relates to a high-temperature-resistant modified epoxy resin adhesive and a preparation method thereof. The high-temperature-resistant modified epoxy resin adhesive comprises the following formula components by weight percent: 55%-58% of epoxy resin, 1%-6% of carboxyl-containing polyimide powder, 3.8%-4% of curing agent, 28.7%-30.5% of diluent and 6.3%-6.8% of terminal carboxyl nitrile rubber. The formula components are mixed evenly to obtain the adhesive. According to the preparation method, carboxyl-containing polyimide is added in an epoxy resin substrate, thereby effectively improving the strength of the adhesive and reducing the brittleness of the cured material of the adhesive; the preparation method has the advantages of simple process and low cost, and is convenient for operation; and the preparation method has a high practicable value for the development of the adhesive industry and has a wide application prospect in multiple fields, such as electronics, microelectronics and the like.
Description
Technical field
The invention belongs to the epoxyn technical field, particularly relate to a kind of high temperature resistant modified epoxy resin tackiness agent and preparation method thereof.
Background technology
Resins, epoxy is a kind of good adhesiveproperties that has, the bonding strength height, bonding wide tackiness agent, it can be with many metals (as iron, steel, copper, aluminium, metal alloy etc.) or non-metallic material (as glass, pottery, timber, plastics etc.) bonding, and bonding strength is very high, even can surpass by the intensity of sticking material itself.In addition, it also has good processing properties and satisfactory stability performance.Yet because the unit elongation of itself is low, fragility is big, bond antifatigue not, should not use at structure position, the fragility of epoxy resin cured product has limited its application greatly.Therefore, every performance of raising epoxyn becomes one of scientific research focus.
At present, to the study on the modification of epoxyn mainly by following three kinds of modes: 1, the Resins, epoxy of development of new; 2, adopt the mode of copolymerization or blend that existing epoxyn is carried out modification.3, utilize the adding solidifying agent in epoxyn, to introduce new structure, thereby improve the performance of epoxyn.The scientific worker of this area has done number of research projects, and has obtained certain technique effect.
Polyimides adhesive is a kind of polyimide that adds in tackiness agent, to improve a class tackiness agent of its performance, because its excellent high thermal resistance and adhesiveproperties have been subjected to people in recent years and have more and more paid close attention to.Polyimides adhesive generally can be divided into following a few class: 1, condensed type polyimides adhesive, this is a quasi-polyimide tackiness agent of researching and developing the earliest, but generate because polyamic acid has water molecules in solidify reaction process, easily bring defective, it is bonding to be unsuitable for big area; 2, thermoplastic polyimide tackiness agent, this is that a class can heating and melting, to the tackiness agent of material adhesive, but its Tg is lower, generally is no more than 250 ℃, so the high temperature bonding performance is not ideal enough; 3, addition polyimide tackiness agent, typical addition polyimide tackiness agent mainly comprises norbornene and the end capped polyimides adhesive of phenylacetylene base.But the former solidification process need pressurize, and thermo-oxidative stability is undesirable, and the toughness of cured article is on the low side.And latter's curing need not pressurization, but solidification value is higher.
Summary of the invention
Technical problem to be solved by this invention provides a kind of high temperature resistant modified epoxy resin tackiness agent and preparation method thereof, in epoxy resin-base, add and contain the carboxyl polyimide, effectively improve the intensity of tackiness agent, and reduce the fragility of its cured article, and technology is simple, cost is low, easy to operate, development to adhesive industry has very high practical value, in various fields such as electronics, microelectronics, has broad application prospects.
A kind of high temperature resistant (general high temperature refers to that initial heat decomposition temperature is more than 350 ℃) of the present invention modified epoxide resin adhesive prescription, its component comprises: Resins, epoxy, contain carboxyl polyimide powder, solidifying agent, thinner and nbr carboxyl terminal, its weight percent is 55%-58%: 1%-6%: 3.8%-4%: 28.7%-30.5%: 6.3%-6.8%.
Described Resins, epoxy is selected from ES216 Resins, epoxy or TGDDM Resins, epoxy; Nbr carboxyl terminal is the CTBN nbr carboxyl terminal.
The described molecular structural formula that contains the carboxyl polyimide is as follows:
Wherein, n is greater than 1, and less than 50 natural number;
Be selected from
The described preparation method who contains the carboxyl polyimide powder comprises:
With 3 of mol ratio 1: 1, two (4-amino-benzene oxygen) phenylformic acid of 5-contain carboxyl aromatic diamine and aromatic series dianhydride in polar non-proton organic solvent by force, in 0 ℃-10 ℃ temperature range internal reactions 5-10 hour, obtain having the transparent homogeneous phase PAA solution of certain viscosity, heat azeotropic dehydration then, complete until the system azeotropic dehydration, subsequently, system is added thermal distillation be concentrated into 1/4-1/3, in acetone, make and contain the carboxyl polyimide powder.
Described aromatic series dianhydride is selected from pyromellitic acid anhydride, 3,3 ', 4,4 '-tetracarboxylic acid benzophenone dianhydride, 3,3 ', 4,4 '-tetracarboxylic acid phenyl ether dianhydride, 2,3,3 ', 4 '-tetracarboxylic acid phenyl ether dianhydride, 3,3 ', 4,4 '-tetracarboxylic acid biphenyl dianhydride, 3,3 ', 4,4 '-tetracarboxylic acid diphenyl sulfone dianhydride, 3,3 ', 4,4 '-tetracarboxylic acid diphenyl sulfide dianhydride, 2, two (3, the 4-dicarboxyl phenyl) hexafluoropropane dianhydrides of 2-, 1, two (3, the 4-di carboxyl phenyloxy) benzene dianhydrides of 4-, 1,3-two (3, the 4-di carboxyl phenyloxy) benzene dianhydride, 1, two (3, the 4-di carboxyl phenyloxy) benzene dianhydrides of 2-, 2, two [4-(3, the 4-di carboxyl phenyloxy) phenyl] the propane dianhydrides of 2-, 2,2-is two, and [4-(3, the 4-di carboxyl phenyloxy) phenyl] hexafluoropropane dianhydride, 1,4,5, one or more in the 8-tetracarboxylic acid naphthalene dianhydride.
Described strong polar non-proton organic solvent is N, one or more in dinethylformamide, N,N-dimethylacetamide, N-N-methyl-2-2-pyrrolidone N-, the dimethyl sulfoxide (DMSO).
The dewatering agent that described azeotropic dehydration uses is in benzene,toluene,xylene, mono chloro benzene, the orthodichlorobenzene one or more.
Described solidifying agent is selected from 3,3 '-diaminodiphenylsulfone(DDS), 4, one or more in 4 '-diaminodiphenylsulfone(DDS), 2-ethyl-4-methylimidazole, Dyhard RU 100, glyoxal ethyline, tetrahydrophthalic anhydride, the methyl tetrahydro phthalic anhydride.
Described thinner is selected from 1,3-2-glycidyl oxygen base benzene, 2, two (the 4-glycidoxypropyl cyclohexyl) propane of 2-, vinyl cyclohexene dioxide, 3,4-epoxy group(ing) heptanaphthenic acid-3 ', 4 '-epoxy group(ing) hexamethylene methyl esters, 3,4-epoxy group(ing)-6-methyl cyclohexane formic acid-3 ', 4 '-epoxy group(ing)-6 '-in the methyl cyclohexane methyl esters one or more.
The preparation method of a kind of high temperature resistant modified epoxy resin tackiness agent of the present invention comprises:
With Resins, epoxy, to contain carboxyl polyimide powder, solidifying agent, thinner and nbr carboxyl terminal be 55%-58%: 1%-6%: 3.8%-4%: 28.7%-30.5% with the weight percent: 6.3%-6.8% mixes, promptly.
High temperature resistant modified epoxy resin tackiness agent of the present invention has broad application prospects in fields such as electronics microelectronics, flexible copper clad foil plate (FCCL), flexible printed circuit board (FPC), rigid copper coated foil plate (PCB), motor, aerospace.
Beneficial effect
(1) modest viscosity of high temperature resistant modified epoxy resin tackiness agent provided by the invention, good manufacturability, and to metal base (comprising iron, copper, aluminium alloy, glass, pottery etc.) adhesiveproperties excellence;
(2) adhesive composition reactive group controllability of the present invention is good, toughness and excellent heat resistance, and hydrophobicity is strong, anti-atomic oxygen, excellent combination property;
(3) the tensile shear strength height of high temperature resistant modified epoxy resin tackiness agent of the present invention, thermotolerance is higher, and the fragility of cured article is low, and the development of adhesive industry is had very high practical value;
(4) preparation technology of high temperature resistant modified epoxy resin tackiness agent of the present invention is simple, easy to operate, and the reaction raw materials convenient sources can be finished preparation process in general-purpose equipment, help realizing suitability for industrialized production.
Embodiment
Below in conjunction with specific embodiment, further set forth the present invention.Should be understood that these embodiment only to be used to the present invention is described and be not used in and limit the scope of the invention.Should be understood that in addition those skilled in the art can make various changes or modifications the present invention after the content of having read the present invention's instruction, these equivalent form of values fall within the application's appended claims institute restricted portion equally.
Embodiment 1
With 0.1 mole (33.6 gram) 3, the N of two (4-amino-benzene oxygen) phenylformic acid of 5-and 300 milliliters, the strong polar non-proton organic solvent of N-N,N-DIMETHYLACETAMIDE adds in the polymerization bottle, stirring and dissolving, add 0.1 mole (31.0 gram) 3,3 ', 4,4 '-tetracarboxylic acid phenyl ether dianhydride powder, after reacting 5-10 hour under 0 ℃-10 ℃, the transparent PAA solution that obtains having certain viscosity, add 300 milliliters of methylbenzene azeotropic dewatering agents, heat azeotropic dehydration subsequently, complete until azeotropic dehydration, about 6 hours, then reaction system being added thermal distillation concentrates approximately to 1/3, stir precipitating in the acetone high speed and make and contain carboxyl polyimide CPI-1 powder, limiting viscosity is 0.62dL/g (25 ℃, the vitriol oil).
Adopt 3,3 ', 4,4 '-tetracarboxylic acid benzophenone dianhydride, 1, two (3, the 4-di carboxyl phenyloxy) benzene dianhydrides, 2 of 4-, 2-is two, and [4-(3, the 4-di carboxyl phenyloxy) phenyl] the aromatic series dianhydride of propane dianhydride waits mole to replace 3,3 ', 4 respectively, 4 '-tetracarboxylic acid phenyl ether dianhydride, other material, proportioning are constant, repeat above-mentioned technology, obtain containing the carboxyl polyimide powder respectively, note is done successively: CPI-2, CPI-3, CPI-4, limiting viscosity is 0.59,0.67,0.54dL/g (25 ℃, the vitriol oil), and its structural formula is as follows successively:
Wherein, n is greater than 1, and less than 50 natural number.
Embodiment 2
TGDDM Resins, epoxy: 58.0 grams
CTBN nbr carboxyl terminal: 6.75 grams
CPI-4 powder: 1.0 grams
Dicy-curing agent: 4.0 grams
1,3-2-glycidyl oxygen master dilution agent: 30.25 grams
Mentioned component at room temperature stirred promptly to get contain the polyimide modified epoxy adhesive of carboxyl.Its result of use can reach the purpose of invention.
Embodiment 3
ES216 Resins, epoxy: 56.8 grams
CTBN nbr carboxyl terminal: 6.6 grams
CPI-3 powder: 3.0 grams
2-ethyl-4-methylimidazole solidifying agent: 1.8 grams
Dicy-curing agent: 2.15 grams
2, two (4-glycidoxypropyl cyclohexyl) propane thinners of 2-: 15.2 grams
Vinyl cyclohexene dioxide thinner: 14.46 grams
Mentioned component at room temperature stirred promptly to get contain the polyimide modified epoxy adhesive of carboxyl.Its result of use can reach the purpose of invention.
Embodiment 4
ES216 Resins, epoxy: 55.7 grams
CTBN nbr carboxyl terminal: 6.5 grams
CPI-1 powder: 5.0 grams
Methyl tetrahydro phthalic anhydride solidifying agent: 2.08 grams
2-ethyl-4-methylimidazole solidifying agent: 1.8 grams
3,4-epoxy group(ing) heptanaphthenic acid-3 ', 4 '-epoxy group(ing) hexamethylene methyl esters thinner: 29.0 grams
Mentioned component at room temperature stirred promptly to get contain the polyimide modified epoxy adhesive of carboxyl.Its result of use can reach the purpose of invention.
Embodiment 5
ES216 Resins, epoxy: 55.17 grams
CTBN nbr carboxyl terminal: 6.43 grams
CPI-2 powder: 6.0 grams
4,4 '-diaminodiphenylsulfone(DDS) solidifying agent: 2.64 grams
Dicy-curing agent: 1.2 grams
3,4-epoxy group(ing) heptanaphthenic acid-3 ', 4 '-epoxy group(ing) hexamethylene methyl esters thinner: 28.7 grams
Mentioned component at room temperature stirred promptly to get contain the polyimide modified epoxy adhesive of carboxyl.Its result of use can reach the purpose of invention.
" the tackiness agent tensile shear strength is measured (rigid material is to rigid material) (replacing GB/T7124-1986 " tackiness agent tensile shear strength measuring method (metal to metal) "); get epoxy binder modified in right amount; also evenly be coated on the polishing standard iron plate afterwards; superimposed; as to clamp; put into convection oven and be cured: begin to be warming up to 100 ℃ from room temperature, insulation reaction 1 hour continues to be warming up to 150 ℃ according to GB/T7124-2008, insulation reaction 1 hour, continue to be warming up to 175 ℃, insulation reaction 1.5 hours continues to be warming up to 200 ℃, be incubated 3 hours, naturally cool to room temperature, every kind of prescription is no less than 5, is used for test.
Measure the water-intake rate of adhesive solidification thing according to State Standard of the People's Republic of China (GB1034-70) " plastics water absorption test method ".Get and contain the polyimide modified epoxy adhesive of carboxyl in right amount, on poly-tinfoil, push away film, make the square sample that is of a size of 5mm * 5mm * 1mm, put into convection oven and be cured, curing process is: begin to be warming up to 100 ℃ from room temperature, insulation reaction 1 hour continues to be warming up to 150 ℃, insulation reaction 1 hour, continue to be warming up to 175 ℃, insulation reaction 1.5 hours continues to be warming up to 200 ℃, is incubated 3 hours.With the square sample of the above-mentioned exsiccant (W that weighs
1) after, be soaked in the deionized water (25 ℃), after 72 hours, take out, dry the surface with filter paper, (W weighs
2), be used to test water-intake rate.
Performance test is as follows:
The amount that contains the carboxyl polyimide in the tackiness agent of the present invention is between 1%-6%, and its effect is more satisfactory.As long as in formula range of the present invention, this tackiness agent viscosity is to the adhesiveproperties excellence of iron plate, room temperature (25 ℃) tensile shear strength height, and controllability is good, good manufacturability.
Claims (10)
1. high temperature resistant modified epoxy resin adhesive formulation, its component comprises: Resins, epoxy, contain carboxyl polyimide powder, solidifying agent, thinner and nbr carboxyl terminal, its weight percent is,
55％-58％∶1％-6％∶3.8％-4％∶28.7％-30.5％∶6.3％-6.8％。
2. a kind of high temperature resistant modified epoxy resin adhesive formulation according to claim 1 is characterized in that: described Resins, epoxy is selected from ES216 Resins, epoxy or TGDDM Resins, epoxy; Nbr carboxyl terminal is the CTBN nbr carboxyl terminal.
3. a kind of high temperature resistant modified epoxy resin adhesive formulation according to claim 1 and 2 is characterized in that: the described molecular structural formula that contains the carboxyl polyimide is as follows:
Wherein, n is greater than 1, and less than 50 natural number;
Be selected from
4. a kind of high temperature resistant modified epoxy resin adhesive formulation according to claim 3 is characterized in that: the described preparation method who contains the carboxyl polyimide powder comprises:
With 3 of mol ratio 1: 1, two (4-amino-benzene oxygen) phenylformic acid of 5-contain carboxyl aromatic diamine and aromatic series dianhydride in polar non-proton organic solvent by force, in 0 ℃-10 ℃ temperature range internal reactions 5-10 hour, obtain the transparent homogeneous phase PAA solution of viscosity, heat azeotropic dehydration then, complete until the system azeotropic dehydration, subsequently, system is added thermal distillation be concentrated into 1/4-1/3, in acetone, make and contain the carboxyl polyimide powder.
5. a kind of high temperature resistant modified epoxy resin adhesive formulation according to claim 4 is characterized in that: described aromatic series dianhydride is selected from pyromellitic acid anhydride, 3,3 ', 4,4 '-tetracarboxylic acid benzophenone dianhydride, 3,3 ', 4,4 '-tetracarboxylic acid phenyl ether dianhydride, 2,3,3 ', 4 '-tetracarboxylic acid phenyl ether dianhydride, 3,3 ', 4,4 '-tetracarboxylic acid biphenyl dianhydride, 3,3 ', 4,4 '-tetracarboxylic acid diphenyl sulfone dianhydride, 3,3 ', 4,4 '-tetracarboxylic acid diphenyl sulfide dianhydride, 2,2-two (3,4-dicarboxyl phenyl) hexafluoropropane dianhydride, 1, two (3, the 4-di carboxyl phenyloxy) benzene dianhydrides of 4-, 1,3-two (3, the 4-di carboxyl phenyloxy) benzene dianhydride, 1, two (3, the 4-di carboxyl phenyloxy) benzene dianhydrides of 2-, 2,2-is two, and [4-(3, the 4-di carboxyl phenyloxy) phenyl] the propane dianhydride, 2, two [4-(3, the 4-di carboxyl phenyloxy) phenyl] hexafluoropropane dianhydrides of 2-, 1,4,5, one or more in the 8-tetracarboxylic acid naphthalene dianhydride.
6. a kind of high temperature resistant modified epoxy resin adhesive formulation according to claim 4, it is characterized in that: described strong polar non-proton organic solvent is N, in dinethylformamide, N,N-dimethylacetamide, N-N-methyl-2-2-pyrrolidone N-, the dimethyl sulfoxide (DMSO) one or more.
7. a kind of high temperature resistant modified epoxy resin adhesive formulation according to claim 4 is characterized in that: the dewatering agent that described azeotropic dehydration uses is in benzene,toluene,xylene, mono chloro benzene, the orthodichlorobenzene one or more.
8. a kind of high temperature resistant modified epoxy resin adhesive formulation according to claim 1 and 2, it is characterized in that: described solidifying agent is selected from 3,3 '-diaminodiphenylsulfone(DDS), 4, one or more in 4 '-diaminodiphenylsulfone(DDS), 2-ethyl-4-methylimidazole, Dyhard RU 100, glyoxal ethyline, tetrahydrophthalic anhydride, the methyl tetrahydro phthalic anhydride.
9. a kind of high temperature resistant modified epoxy resin adhesive formulation according to claim 1 and 2, it is characterized in that: described thinner is selected from 1,3-2-glycidyl oxygen base benzene, 2, two (the 4-glycidoxypropyl cyclohexyl) propane of 2-, vinyl cyclohexene dioxide, 3,4-epoxy group(ing) heptanaphthenic acid-3 ', 4 '-epoxy group(ing) hexamethylene methyl esters, 3,4-epoxy group(ing)-6-methyl cyclohexane formic acid-3 ', 4 '-epoxy group(ing)-6 '-in the methyl cyclohexane methyl esters one or more.
10. the preparation method of a high temperature resistant modified epoxy resin tackiness agent comprises:
With Resins, epoxy, to contain carboxyl polyimide powder, solidifying agent, thinner and nbr carboxyl terminal be 55%-58%: 1%-6%: 3.8%-4%: 28.7%-30.5% with the weight percent: 6.3%-6.8% mixes, promptly.
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| CN103131368A (en) * | 2013-03-11 | 2013-06-05 | 东华大学 | 4,4'-bis(2,4-diamidophenoxy)diphenyl ether high-temperature-resistant epoxy adhesive and preparation method thereof |
| CN103980705A (en) * | 2014-04-30 | 2014-08-13 | 中国科学院化学研究所 | High-performance polyimide molding powder material suitable for 3D printing and 3D printing molding method |
| CN104448243A (en) * | 2014-12-10 | 2015-03-25 | 东华大学 | Solvent-free high-temperature-resistant modified epoxy system pultruded resin and preparation method thereof |
| CN105131287A (en) * | 2015-09-30 | 2015-12-09 | 华东理工大学华昌聚合物有限公司 | Method for synthesizing end-amino epoxy resin toughening type curing agent |
| CN107011842A (en) * | 2016-12-16 | 2017-08-04 | 吴中区穹窿山福顺生物技术研究所 | A kind of modified polyimide adhesive |
| CN107266684A (en) * | 2016-04-07 | 2017-10-20 | 比亚迪股份有限公司 | A kind of polyamide-imide resin and resin adhesive and application thereof |
| CN107502259A (en) * | 2017-09-13 | 2017-12-22 | 陈贤尧 | LED encapsulation material that a kind of hardness is high and adhesion strength is excellent and preparation method thereof |
| CN111303815A (en) * | 2020-04-01 | 2020-06-19 | 苏州巨峰电气绝缘系统股份有限公司 | High-thermal-conductivity epoxy pouring sealant and preparation method thereof |
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| CN114686157A (en) * | 2022-03-09 | 2022-07-01 | 江苏环峰电工材料有限公司广州分公司 | Three-dimensional reticular polymer for adhesive and preparation method thereof |
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| CN103131370A (en) * | 2013-03-11 | 2013-06-05 | 东华大学 | 1,3-bis(2,4-diamidophenoxy)benzene high-temperature-resistant epoxy adhesive and preparation method thereof |
| CN103131368A (en) * | 2013-03-11 | 2013-06-05 | 东华大学 | 4,4'-bis(2,4-diamidophenoxy)diphenyl ether high-temperature-resistant epoxy adhesive and preparation method thereof |
| CN103131368B (en) * | 2013-03-11 | 2014-08-13 | 东华大学 | 4,4'-bis(2,4-diamidophenoxy)diphenyl ether high-temperature-resistant epoxy adhesive and preparation method thereof |
| CN103131370B (en) * | 2013-03-11 | 2014-10-15 | 东华大学 | 1,3-bis(2,4-diamidophenoxy)benzene high-temperature-resistant epoxy adhesive and preparation method thereof |
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| CN107502259A (en) * | 2017-09-13 | 2017-12-22 | 陈贤尧 | LED encapsulation material that a kind of hardness is high and adhesion strength is excellent and preparation method thereof |
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| CN102260480B (en) | 2013-05-08 |
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