CN101591521A - A kind of fluorene-containing polyimide adhesive and preparation method thereof - Google Patents
A kind of fluorene-containing polyimide adhesive and preparation method thereof Download PDFInfo
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- CN101591521A CN101591521A CNA2009100881022A CN200910088102A CN101591521A CN 101591521 A CN101591521 A CN 101591521A CN A2009100881022 A CNA2009100881022 A CN A2009100881022A CN 200910088102 A CN200910088102 A CN 200910088102A CN 101591521 A CN101591521 A CN 101591521A
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Abstract
The invention provides a kind of fluorene-containing polyimide adhesive that has good adhesion with metal.It is characterized in that described tackiness agent comprises at least a kind ofly contains the fluorenediamine monomer, contains the fluorenes dianhydride monomer and/or contains the fluorenes end-capping reagent and at least a other diamine monomer, other dianhydride monomer and/or other end-capping reagent.The preparation method of above-mentioned fluorene-containing polyimide adhesive comprises following steps: A. is dissolved in certain amount of diamine, dianhydride or end-capping reagent in the organic solvent, at room temperature stirs, and obtains even polyamic acid; B. adopt chemical imidization method or hot imidization legal system to be equipped with the Kapton of polyimide powder or part imidization; C. certain thickness powder or film are placed between two tinsels, hot pressing certain hour on press obtains the firm single overlap joint bond that bonds.Fluorene-containing polyimide adhesive provided by the invention is applicable to high-tech areas such as Aeronautics and Astronautics and microelectronics.
Description
Technical field
The present invention relates to a kind of fluorene-containing polyimide adhesive and preparation method thereof.Tackiness agent comprises at least and a kind ofly contains the fluorenediamine monomer, contains the fluorenes dianhydride monomer and/or contain the fluorenes end-capping reagent and at least a other diamine monomer, other dianhydride monomer and/or other end-capping reagent.
Background technology
Tackiness agent is a kind of indispensable material in the national economy, and adhesive bonding technique is also full-fledged, becomes the present age three big interconnection technique one of arranged side by side with welding, mechanical connection.Along with the development of modern science technology, space launch vehicles such as launch vehicle, space shuttle all develop towards light weight, good reliability, long direction of life-span, and these new design philosophys are had higher requirement to the resistance to elevated temperatures of tackiness agent; Electronicss such as computer increase thermal value because the intensity of the raising of its signal velocity and electronic component is installed, and its printed wiring switchboard also requires the use temperature of tackiness agent to improve.Polyimide (PI) has higher thermostability, chemical stability and mechanical property, also has excellent especially anti-atomic radiation, can be used for preparing sqtructural adhesive, glued joint metal such as stainless steel, aluminium, copper and titanium alloy etc., meeting the bonding requirement of Aeronautics and Astronautics and microelectronics industry, is the preferred material of thermal structure tackiness agent.
In general, the cohesiveness of polyimide and substrate is good, need meet the following conditions: thermal expansivity (CTE) is lower, have higher melt fluidity under lower temperature.Polyimide is owing to its distinctive rigidity or semirigid skeleton structure and have extremely strong Intermolecular Forces, and is normally insoluble infusible, the machine-shaping difficulty.At present, generally adopt structurally-modified method to improve the solvability and the melt fluidity of polyimide, structurally-modified main method has: introduce flexible structure unit, distortion or asymmetric structure, big side group etc. or preparation copoly type polyimide in polymer backbone.
In recent years, the polyimide of fluorenyl replacement has been subjected to investigator's extensive concern gradually.Fluorenyl is incorporated in the polyimide, can improves thermotolerance, solvability, melt fluidity, the crystallization tendency that reduces of polyimide.General method of modifying can reduce the mechanical property of material when improving the materials processing performance, but the introducing of fluorenyl does not destroy the rigidity of polyimide main chain, has limited segmental and has moved freely, and has kept the mechanical property of material.Simultaneously, free volume that fluorenyl is huge and condensed ring structure help increasing molecule interchain distance, reduce its melt viscosity, improve melt fluidity, thus can fine infiltration bonding surface, the raising cohesive strength.In addition, compare with having crosslinked polyimide with the flexible molecule chain structure, fluorene-containing polyimide is owing to have CTE value linear and that the demonstration of stiff molecule chain structure is lower, and this is because linearity and inflexible molecular chain structure help the ordered arrangement of molecular chain.Therefore, fluorene-containing polyimide adhesive has higher use temperature and cohesive strength, is applicable to high-tech areas such as Aeronautics and Astronautics and microelectronics.
Though disclosing some in the prior art contains the fluorenediamine monomer, contains the fluorenes dianhydride monomer, contains the preparation method of fluorenes end-capping reagent and fluorene-containing polyimide, but fluorene-containing polyimide of the prior art is not open with the technical scheme of fluorene-containing polyimide as tackiness agent generally as advanced low-k materials, gas separation membrane, fuel battery proton exchange film and photoelectric device etc.
Adopt polyimide to make tackiness agent and mainly contain following three kinds of forms: Kapton, polyimide powder and polyamic acid solution.When the form of employing polyamic acid solution prepared bonded part, the volatilization meeting of solvent caused a large amount of hole defectives in matrix in the hot-imide process, reduced cohesive strength.This patent adopts Kapton and form of powder to prepare bonded part, and studies its cohesive strength.
Summary of the invention
The present invention seeks to improve the cohesive strength of existing polyimides adhesive and metal, is that index is carried out experimental formula with the cohesive strength, has now drawn complete technical scheme.
Described tackiness agent comprises at least and a kind ofly contains the fluorenediamine monomer, contains the fluorenes dianhydride monomer and/or contain the fluorenes end-capping reagent and at least a other diamine monomer, other dianhydride monomer and/or other end-capping reagent.
The described fluorenediamine monomer that contains has following general structure:
Wherein, R
1, R
2The divalent group of expression hydrogen atom or aliphatics, alicyclic, aromatic series, carbonyl, ether, sulfuryl.R
3, R
4The univalent perssad of expression hydrogen atom or aliphatics, alicyclic, aromatic series, sulfonic group, halogen formyl radical, carbalkoxy.Specifically, R
1, R
2The aliphatics of expression, alicyclic, aromatic series divalent group can be and replace or unsubstituted ring-type, straight or branched alkylidene group, replacement or unsubstituted ring-type, straight or branched alkylene oxide group, replace or unsubstituted arylidene the divalent group of replacement or unsubstituted inferior aryloxy etc.; R
3, R
4The aliphatics of expression, alicyclic, aromatic series univalent perssad can be and replace or unsubstituted ring-type, straight or branched alkyl, replacement or unsubstituted ring-type, straight or branched alkoxyl group, replace or unsubstituted aryl the univalent perssad of replacement or unsubstituted aryloxy etc.Particularly, described alkylidene group can be methylene radical, isobutylidene, hexafluoroisopropyli,ene, cyclohexylidene, inferior spiral shell decyl etc., and described arylidene can be phenylene, to methyl isopropyl phenylene, diphenylene, inferior carbazyl, naphthylidene etc.; Described alkyl can be methyl, isobutyl-, hexafluoro sec.-propyl, cyclohexyl, spiral shell decyl etc., described alkoxyl group can be methoxyl group, propoxy-, diethoxy etc., described aryl can be phenyl, p-Methylisopropylbenzene base, xenyl, carbazyl, naphthyl etc., and described aryloxy can be phenoxy group, hexichol ether, triphen two ethers etc.; Described substituted radical can be halogen atom, Siliciumatom, sulphur atom, cyano group etc.R
1～R
4Can be when being connected on the phenyl ring in any position of phenyl ring.
The described fluorenes dianhydride monomer that contains has following general structure:
Wherein, R
5, R
6The divalent group of expression hydrogen atom or aliphatics, alicyclic, aromatic series, carbonyl, ether, sulfuryl.R
7, R
8The univalent perssad of expression hydrogen atom or aliphatics, alicyclic, aromatic series, sulfonic group, halogen formyl radical, carbalkoxy.Specifically, R
5, R
6The aliphatics of expression, alicyclic, aromatic series divalent group can be and replace or unsubstituted ring-type, straight or branched alkylidene group, replacement or unsubstituted ring-type, straight or branched alkylene oxide group, replace or unsubstituted arylidene the divalent group of replacement or unsubstituted inferior aryloxy etc.; R
7, R
8The aliphatics of expression, alicyclic, aromatic series can be and replaces or unsubstituted ring-type, straight or branched alkyl, replace or unsubstituted ring-type, straight or branched alkoxyl group, replace or unsubstituted aryl, replace or the univalent perssad of unsubstituted aryloxy etc.Particularly, described alkylidene group can be methylene radical, isobutylidene, hexafluoroisopropyli,ene, cyclohexylidene, inferior spiral shell decyl etc., and described arylidene can be phenylene, to methyl isopropyl phenylene, diphenylene, inferior carbazyl, naphthylidene etc.; Described alkyl can be methyl, isobutyl-, hexafluoro sec.-propyl, cyclohexyl, spiral shell decyl etc., described alkoxyl group can be methoxyl group, propoxy-, diethoxy etc., described aryl can be phenyl, p-Methylisopropylbenzene base, xenyl, carbazyl, naphthyl etc., and described aryloxy can be phenoxy group, hexichol ether, triphen two ethers etc.; Described substituted radical can be halogen atom, Siliciumatom, sulphur atom, cyano group etc.R
5～R
8Can be when being connected on the phenyl ring in any position of phenyl ring.
The described fluorenes end-capping reagent that contains has following general structure:
Wherein, R
9The divalent group of expression hydrogen atom or aliphatics, alicyclic, aromatic series, carbonyl, ether, sulfuryl.R
10, R
11The univalent perssad of expression hydrogen atom or aliphatics, alicyclic, aromatic series, sulfonic group, halogen formyl radical, carbalkoxy.Specifically, R
9The aliphatics of expression, alicyclic, aromatic series divalent group can be and replace or unsubstituted ring-type, straight or branched alkylidene group, replacement or unsubstituted ring-type, straight or branched alkylene oxide group, replace or unsubstituted arylidene the divalent group of replacement or unsubstituted inferior aryloxy etc.; R
10, R
11The aliphatics of expression, alicyclic, aromatic series can be and replaces or unsubstituted ring-type, straight or branched alkyl, replace or unsubstituted ring-type, straight or branched alkoxyl group, replace or unsubstituted aryl, replace or the univalent perssad of unsubstituted aryloxy etc.Particularly, described alkylidene group can be methylene radical, isobutylidene, hexafluoroisopropyli,ene, cyclohexylidene, inferior spiral shell decyl etc., and described arylidene can be phenylene, to methyl isopropyl phenylene, diphenylene, inferior carbazyl, naphthylidene etc.; Described alkyl can be methyl, isobutyl-, hexafluoro sec.-propyl, cyclohexyl, spiral shell decyl etc., described alkoxyl group can be methoxyl group, propoxy-, diethoxy etc., described aryl can be phenyl, p-Methylisopropylbenzene base, xenyl, carbazyl, naphthyl etc., and described aryloxy can be phenoxy group, hexichol ether, triphen two ethers etc.; Described substituted radical can be halogen atom, Siliciumatom, sulphur atom, cyano group etc.R
9～R
11Can be when being connected on the phenyl ring in any position of phenyl ring.
Described other diamine monomer is selected from quadrol, 1, the 4-butanediamine, 1, the 6-hexanediamine, 1, the 8-octamethylenediamine, 1, the 10-decamethylene diamine, mphenylenediamine, Ursol D, 1,3,5-trimethylammonium mphenylenediamine, 2,3,5, the 6-tetramethyl-para-phenylene diamine, 3,4 '-diaminodiphenyl oxide, 4,4 '-diaminodiphenyl oxide, 1,3-two (4-amino-benzene oxygen) benzene, 1,4-two (4 '-amino-benzene oxygen) benzene, 1,4-two (2-trifluoromethyl, 4 '-amino-benzene oxygen) benzene, 4,4 '-diaminodiphenylmethane, 3,3 '-dimethyl-4,4 '-diaminodiphenylmethane, 3,3 '-dimethoxy-4 ', 4 '-diaminodiphenylmethane, 2,2 '-dimethoxy-4 ', 4 '-diaminodiphenylmethane, 2,2 '-tolidine, 3,3 '-tolidine, 2,2 '-two (trifluoromethyl) p-diaminodiphenyl, 2,2 '-two (trifluoromethoxy) p-diaminodiphenyl, 3,3 '-diaminodiphenyl sulfide, 4,4 '-diaminodiphenyl sulfide, 3,3 '-diaminodiphenylsulfone(DDS), 4,4 '-diaminodiphenylsulfone(DDS), 3,3 '-diamino benzophenone, 4,4 '-diamino benzophenone, two (4-ammonia phenoxy groups)-1,4 '-benzene, 2,2 '-(4-aminophenyl) propane, 2,2 '-(4-aminophenyl) HFC-236fa, 2,2 '-(4-ammonia Phenoxyphenyl) HFC-236fa, in the polysiloxane diamine one or more.
Described other dianhydride monomer is selected from pyromellitic acid dianhydride, 2,3,3 ', 4 '-BPDA, 3,3 ', 4,4 '-BPDA, 2,3,3 ', 4 '-phenyl ether tetracarboxylic dianhydride, 3,3 ', 4,4 '-phenyl ether tetracarboxylic dianhydride, 3,3 ', 4,4 '-benzophenone tetracarboxylic dianhydride, triphen diether tetracarboxylic dianhydride, 1,2,3,4-tetracarboxylic butane dianhydride, the tetramethylene tetracarboxylic dianhydride, the pentamethylene tetracarboxylic dianhydride, 2,2 '-two [3,4-two carboxyphenyls] the propane dianhydride, 2,2 '-two [4-di carboxyl phenyloxy phenyl] propane dianhydride, 2,2 '-two [3,4-two carboxyphenyls] hexafluoropropane dianhydride, 2,2 '-two [3,4-two carboxyphenyls] ether dianhydride, 2,2 '-two [3,4-two carboxyphenyls] the thioether dianhydride, 2,2 '-two [3,4-two carboxyphenyls] sulfone dianhydride, 2,2 '-two [3,4-two carboxyphenyls] the methane dianhydride, 1, two [3, the 4 '-dicarboxyl phenoxy group] benzene dianhydrides of 4-, 1,3-two [3 ', 4-two carboxyphenyls] benzene dianhydride, 2,2 '-two [3,4-dicarboxyl phenoxy group-1,4 '-penylene] propane dianhydride, 4,4 '-two [3,4-dicarboxyl phenoxy group] biphenyl dianhydride, 2,3,6,7-naphthalene tetracarboxylic dianhydride, 1,4,5,8-naphthalene tetracarboxylic dianhydride, sulfobenzide-2,3,3 ', 4 '-tetracarboxylic dianhydride, sulfobenzide-2,2 ', 3,3 '-tetracarboxylic dianhydride, in the anthraquinone tetracarboxylic dianhydride one or more.
Described other end-capping reagent is selected from Tetra hydro Phthalic anhydride, aniline, vinyl aniline, acetylene, phenylacetylene, 3-phenylacetylene base aniline, phenylacetylene phthalic anhydride, 5-norbornylene-2,3-dicarboxylic anhydride, 5-norbornylene-2,3-diformate mono acid anhydride etc.
The invention discloses a kind of preparation method of fluorene-containing polyimide adhesive, carry out according to the following steps: contain the fluorenediamine monomer, contain the fluorenes dianhydride monomer and/or contain the fluorenes end-capping reagent a kind of, be dissolved in the organic solvent with at least a other diamine monomer, other dianhydride monomer and/or other end-capping reagent, at room temperature stir, obtain even polyamic acid; Polyamic acid solution is coated on the sheet glass, in the far infrared baking oven, carries out the stage intensification, the Kapton of preparation part imidization; Or in polyamic acid solution, add dewatering agent and catalyzer, adopt the chemical imidization legal system to get polyimide powder.
With the sand paper metallic surface of fully polishing, use acetone rinsing again, dry for standby in electric drying oven with forced convection; Certain thickness film is placed between two tinsels or soak into polyimide powder and the sticky shape of furnishing, it be applied in the tinsel surface uniformly with ethanol, afterwards with another sheet metallic bone on its surface; According to the single overlap joint of GB7124-86 standard fabrication bond, hot pressing on press obtains the firm exemplar that bonds.
Described organic solvent is selected from N-Methyl pyrrolidone, N, N '-dimethyl formamide, N, one or more in N '-N,N-DIMETHYLACETAMIDE, the meta-cresol.
Tackiness agent good heat resistance of the present invention, cohesive strength is higher.Tackiness agent is as follows to its shearing resistance of stainless bonding: 25 ℃ of 30MPa, 100 ℃ of 28.7MPa, 150 ℃ of 26.4MPa, 200 ℃ of 25MPa, 250 ℃ of 23.2MPa; Its shearing resistance of bonding to titanium alloy is as follows: 25 ℃ of 29.5MPa, 100 ℃ of 28MPa, 150 ℃ of 25.9MPa, 200 ℃ of 24.1MPa, 250 ℃ of 22.5MPa.
Embodiment
The present invention illustrates it especially exemplified by example for better implement, but is not limitation of the present invention.
Embodiment 1
With 4 of 0.98mol, 4 '-diaminodiphenyl oxide fully is dissolved in the solvent N-Methyl pyrrolidone, adds 3,3 ', 4,4 '-two methyl-phenoxide tetracarboxylic acid anhydrides of 1mol behind the 15min, at room temperature stirs; Add 0.05mol end-capping reagent alpha-amino group fluorenes behind the 12h, continue to stir 12h and obtain even polyamic acid; Polyamic acid solution is coated on the sheet glass, carries out the stage to heat up in the far infrared baking oven, the Kapton of preparation part imidization, heating schedule are 80 ℃/2h, 120 ℃/1h, 150 ℃/1h, 200 ℃/1h.
With the sand paper metallic surface of fully polishing, use acetone rinsing again, in electric drying oven with forced convection, dry; The double-layer films that 0.04mm is thick places between two tinsels, adopts the hot pressing on press of GB7124-86 standard, and pressure is 1-2MPa, put into when temperature is 200 ℃, be warmed up to 370 ℃, constant voltage 2h under this temperature, the cooling of pressurize afterwards obtains the firm single overlap joint bond that bonds.
Tackiness agent is as follows to its shearing resistance of stainless bonding: 25 ℃ of 28.5MPa, 100 ℃ of 26.9MPa, 150 ℃ of 24.5MPa, 200 ℃ of 23.2MPa, 250 ℃ of 22.1MPa; Its shearing resistance of bonding to titanium alloy is as follows: 25 ℃ of 28MPa, 100 ℃ of 26.5MPa, 150 ℃ of 24MPa, 200 ℃ of 22.9MPa, 250 ℃ of 21.7MPa.
Embodiment 2
With 3 of 0.25mol, 9,9 '-two (2-trifluoromethyl, 4-amino-benzene oxygen phenyl) fluorenes of 3 '-diaminodiphenylsulfone(DDS) and 0.25mol fully is dissolved in the solvent N-Methyl pyrrolidone, add the triphen diether tetracarboxylic dianhydride of 0.5mol behind the 15min, at room temperature stir; Obtain even polyamic acid after stirring 24h.
The processing mode of metallic surface is the same with embodiment 1 operation.With glass stick polyamic acid solution evenly is coated on by the abutting edge, behind 120 ℃ of oven dry 30min, continue the polyamide coating acid solution, afterwards oven dry, reach about 0.04mm until bondline thickness, adopt the hot pressing on press of GB7124-86 standard, pressure is 1-2MPa, puts into when temperature is 200 ℃, be warmed up to 350 ℃, constant voltage 2h under this temperature, the cooling of pressurize afterwards obtains the firm single overlap joint bond that bonds.
Tackiness agent is as follows to its shearing resistance of stainless bonding: 25 ℃ of 27.4MPa, 100 ℃ of 25MPa, 150 ℃ of 23.2MPa, 200 ℃ of 22MPa, 250 ℃ of 20.9MPa; Its shearing resistance of bonding to titanium alloy is as follows: 25 ℃ of 27MPa, 100 ℃ of 24.8MPa, 150 ℃ of 22.9MPa, 200 ℃ of 21MPa, 250 ℃ of 20MPa.
Embodiment 3
With 0.04mol 9,9 '-two (4-aminophenyl) fluorenes and 0.06mol 1, two amine mixt of 3-two (4-amino-benzene oxygen) benzene fully are dissolved in solvent N, in N '-N,N-DIMETHYLACETAMIDE, add 3,3 ' of 0.98mol behind the 15min, 4,4 '-benzophenone tetracarboxylic acid anhydride at room temperature stirs; Add 0.05mol end-capping reagent Tetra hydro Phthalic anhydride behind the 12h, continue to stir 12h and obtain even polyamic acid; The N that in polyamic acid solution, adds about equal volume, N '-N,N-DIMETHYLACETAMIDE is diluted, stir, adopt dropping funnel to the mixed solution that wherein slowly drips benzoyl oxide and aminopyridine, treat that powder begins to separate out the back and continues to stir 4h, treat that polyimide powder is separated out fully after, in its impouring ethanol, repeatedly washing, suction filtration at 80 ℃ of following vacuum-drying 12h, obtain the exsiccant polyimide powder afterwards.
The processing mode of metallic surface is the same with embodiment 1 operation.Soak into polyimide powder with ethanol, the sticky shape of furnishing is applied in the metallic surface uniformly with it, and compacting, thickness are about 0.05mm, afterwards with another sheet metallic bone on its surface; Adopt the hot pressing on press of GB7124-86 standard, pressure is 1-2MPa, when being 200 ℃, temperature puts into, and 325 ℃ of hot pressing 1h, 375 ℃ of hot pressing 1h, the cooling of pressurize afterwards obtains the firm single overlap joint bond that bonds.
Tackiness agent is as follows to its shearing resistance of stainless bonding: 25 ℃ of 28.7MPa, 100 ℃ of 27.2MPa, 150 ℃ of 25.9MPa, 200 ℃ of 24.3MPa, 250 ℃ of 23MPa; Its shearing resistance of bonding to titanium alloy is as follows: 25 ℃ of 28.1MPa, 100 ℃ of 26.7MPa, 150 ℃ of 25MPa, 200 ℃ of 23.9MPa, 250 ℃ of 22.3MPa.
Embodiment 4
9,9 '-two (4-amino-benzene oxygen phenyl) fluorenes of 1mol fully is dissolved in solvent N, in N '-N,N-DIMETHYLACETAMIDE, adds 2,2 '-two [3, the 4-two carboxyphenyls] ether dianhydride of 1mol behind the 15min, at room temperature stir; Obtain even polyamic acid after stirring 24h; The mixed solution that adds diacetyl oxide and pyridine in polyamic acid solution obtains the homogeneous polyimide solution after continuing to stir 12h; To obtain light yellow thread precipitation in the slow impouring anhydrous methanol of this solution; Should precipitate with methyl alcohol repeatedly wash, suction filtration; At 80 ℃ of following vacuum-drying 12h, obtain the exsiccant polyimide powder afterwards.
Other is the same with embodiment 3 operations.
Tackiness agent is as follows to its shearing resistance of stainless bonding: 25 ℃ of 28.1MPa, 100 ℃ of 27MPa, 150 ℃ of 26.2MPa, 200 ℃ of 25MPa, 250 ℃ of 23.9MPa; Its shearing resistance of bonding to titanium alloy is as follows: 25 ℃ of 27.9MPa, 100 ℃ of 26.7MPa, 150 ℃ of 25.6MPa, 200 ℃ of 23.9MPa, 250 ℃ of 22.3MPa.
Embodiment 5
With 2 of 0.1mol, 2 '-two (4-amino-benzene oxygens)-9,9 '-spiral shell, two fluorenes fully are dissolved in the solvent meta-cresol, add 0.02mol biphenyl tetracarboxylic acid anhydrides and 0.08mol 2 behind the 10min, 2 '-two [3,4-two carboxyphenyls] the dianhydride mixture of sulfone dianhydride, obtain even polyamic acid after at room temperature stirring 24h; Adopt dropping funnel to the mixed solution that wherein slowly drips diacetyl oxide and pyridine, continue to stir 12h; In solution impouring methyl alcohol, obtain thread precipitation, repeatedly washing, suction filtration at 80 ℃ of following vacuum-drying 12h, obtain the exsiccant polyimide powder afterwards.
Other is the same with embodiment 3 operations.During hot pressing, pressure is 2-3MPa on press, when being 200 ℃, temperature puts into, and 300 ℃ of hot pressing 1h, 350 ℃ of hot pressing 1h, the cooling of pressurize afterwards obtains the firm single overlap joint bond that bonds.
Tackiness agent is as follows to its shearing resistance of stainless bonding: 25 ℃ of 29MPa, 100 ℃ of 27.5MPa, 150 ℃ of 25MPa, 200 ℃ of 23.4MPa, 250 ℃ of 22.5MPa; Its shearing resistance of bonding to titanium alloy is as follows: 25 ℃ of 28.5MPa, 100 ℃ of 26.7MPa, 150 ℃ of 24.1MPa, 200 ℃ of 22.7MPa, 250 ℃ of 21.5MPa.
Embodiment 6
With 1,3 of 1.18mol, 5-trimethylammonium mphenylenediamine fully is dissolved in the solvent N-Methyl pyrrolidone, adds 2,2 '-two [4-di carboxyl phenyloxy phenyl] the propane dianhydride of 1.2mol behind the 15min, at room temperature stirs; Add 0.06mol end-capping reagent beta-amino fluorenes behind the 12h, continue to stir 12h and obtain even polyamic acid; Polyamic acid solution is coated on the sheet glass, carries out the stage to heat up in the far infrared baking oven, the Kapton of preparation part imidization, heating schedule are 80 ℃/2h, 120 ℃/1h, 150 ℃/1h, 200 ℃/1h.
Other is the same with embodiment 2 operations.
Tackiness agent is as follows to its shearing resistance of stainless bonding: 25 ℃ of 28.8MPa, 100 ℃ of 27MPa, 150 ℃ of 25.1MPa, 200 ℃ of 24MPa, 250 ℃ of 22.9MPa; Its shearing resistance of bonding to titanium alloy is as follows: 25 ℃ of 28.1MPa, 100 ℃ of 26.7MPa, 150 ℃ of 24.5MPa, 200 ℃ of 23.4MPa, 250 ℃ of 22MPa.
Embodiment 7
With 0.68mol 3,4 '-diaminodiphenyl oxide and 0.29mol 1, two amine mixt of 4-two (2-trifluoromethyl, 4 '-amino-benzene oxygen) benzene fully are dissolved in solvent N, in N '-dimethyl formamide, add 2,3 of 1mol behind the 15min, 6,7-naphthalene tetracarboxylic dianhydride at room temperature stirs; Add 0.06mol end-capping reagent alpha-amino group fluorenes behind the 12h, continue to stir 12h and obtain even polyamic acid; Polyamic acid solution is coated on the sheet glass, carries out the stage to heat up in the far infrared baking oven, the Kapton of preparation part imidization, heating schedule are 80 ℃/1h, 120 ℃/1h, 150 ℃/1h, 200 ℃/1h, 230 ℃/1h.
The processing mode of metallic surface is the same with embodiment 1 operation.The three-layer thin-film that 0.06mm is thick places between two tinsels, adopts the hot pressing on press of GB7124-86 standard, and pressure is 2-4MPa, put into when temperature is 200 ℃, be warmed up to 325 ℃, constant voltage 2h under this temperature, the cooling of pressurize afterwards obtains the firm single overlap joint bond that bonds.
Tackiness agent is as follows to its shearing resistance of stainless bonding: 25 ℃ of 27.7MPa, 100 ℃ of 26.5MPa, 150 ℃ of 24.6MPa, 200 ℃ of 23.3MPa, 250 ℃ of 22.1MPa; Its shearing resistance of bonding to titanium alloy is as follows: 25 ℃ of 26.9MPa, 100 ℃ of 25.6MPa, 150 ℃ of 23.9MPa, 200 ℃ of 22.1MPa, 250 ℃ of 21.2MPa.
Embodiment 8
With 2 of 0.1mol, 7-two (diamino-2 ', 7 '-dibutyl-9,9 ' spiral shell, two fluorenes) fully be dissolved in the solvent meta-cresol, add 0.02mol tetramethylene tetracarboxylic dianhydride and 0.08mol 1 behind the 10min, the mixture of two [3 ', the 4-two carboxyphenyls] benzene dianhydrides of 3-obtains even polyamic acid after at room temperature stirring 24h.
Other is the same with example 2 operations.During hot pressing, pressure is 2-3MPa on press, when being 200 ℃, temperature puts into, and 300 ℃ of hot pressing 1h, 350 ℃ of hot pressing 1h, the cooling of pressurize afterwards obtains the firm single overlap joint bond that bonds.
Tackiness agent is as follows to its shearing resistance of stainless bonding: 25 ℃ of 27.6MPa, 100 ℃ of 26.5MPa, 150 ℃ of 25MPa, 200 ℃ of 23.6MPa, 250 ℃ of 22.4MPa; Its shearing resistance of bonding to titanium alloy is as follows: 25 ℃ of 27.1MPa, 100 ℃ of 25.9MPa, 150 ℃ of 24.3MPa, 200 ℃ of 22.5MPa, 250 ℃ of 21.2MPa.
Claims (9)
1 one kinds of fluorene-containing polyimide adhesives is characterized in that: described tackiness agent comprises at least and a kind ofly contains the fluorenediamine monomer, contains the fluorenes dianhydride monomer and/or contain the fluorenes end-capping reagent and at least a other diamine monomer, other dianhydride monomer and/or other end-capping reagent.
2 according to the described fluorene-containing polyimide adhesive of claim 1, and the wherein said fluorenediamine monomer that contains has following general structure:
Wherein, R
1, R
2The divalent group of expression hydrogen atom or aliphatics, alicyclic, aromatic series, carbonyl, ether, sulfuryl.R
3, R
4The univalent perssad of expression hydrogen atom or aliphatics, alicyclic, aromatic series, sulfonic group, halogen formyl radical, carbalkoxy.Specifically, R
1, R
2The aliphatics of expression, alicyclic, aromatic series divalent group can be and replace or unsubstituted ring-type, straight or branched alkylidene group, replacement or unsubstituted ring-type, straight or branched alkylene oxide group, replace or unsubstituted arylidene the divalent group of replacement or unsubstituted inferior aryloxy etc.; R
3, R
4The aliphatics of expression, alicyclic, aromatic series univalent perssad can be and replace or unsubstituted ring-type, straight or branched alkyl, replacement or unsubstituted ring-type, straight or branched alkoxyl group, replace or unsubstituted aryl the univalent perssad of replacement or unsubstituted aryloxy etc.Particularly, described alkylidene group can be methylene radical, isobutylidene, hexafluoroisopropyli,ene, cyclohexylidene, inferior spiral shell decyl etc., and described arylidene can be phenylene, to methyl isopropyl phenylene, diphenylene, inferior carbazyl, naphthylidene etc.; Described alkyl can be methyl, isobutyl-, hexafluoro sec.-propyl, cyclohexyl, spiral shell decyl etc., described alkoxyl group can be methoxyl group, propoxy-, diethoxy etc., described aryl can be phenyl, p-Methylisopropylbenzene base, xenyl, carbazyl, naphthyl etc., and described aryloxy can be phenoxy group, hexichol ether, triphen two ethers etc.; Described substituted radical can be halogen atom, Siliciumatom, sulphur atom, cyano group etc.R
1～R
4Can be when being connected on the phenyl ring in any position of phenyl ring.
3 according to the described fluorene-containing polyimide adhesive of claim 1, and the wherein said fluorenes dianhydride monomer that contains has following general structure:
Wherein, R
5, R
6The divalent group of expression hydrogen atom or aliphatics, alicyclic, aromatic series, carbonyl, ether, sulfuryl.R
7, R
8The univalent perssad of expression hydrogen atom or aliphatics, alicyclic, aromatic series, sulfonic group, halogen formyl radical, carbalkoxy.Specifically, R
5, R
6The aliphatics of expression, alicyclic, aromatic series divalent group can be and replace or unsubstituted ring-type, straight or branched alkylidene group, replacement or unsubstituted ring-type, straight or branched alkylene oxide group, replace or unsubstituted arylidene the divalent group of replacement or unsubstituted inferior aryloxy etc.; R
7, R
8The aliphatics of expression, alicyclic, aromatic series can be and replaces or unsubstituted ring-type, straight or branched alkyl, replace or unsubstituted ring-type, straight or branched alkoxyl group, replace or unsubstituted aryl, replace or the univalent perssad of unsubstituted aryloxy etc.Particularly, described alkylidene group can be methylene radical, isobutylidene, hexafluoroisopropyli,ene, cyclohexylidene, inferior spiral shell decyl etc., and described arylidene can be phenylene, to methyl isopropyl phenylene, diphenylene, inferior carbazyl, naphthylidene etc.; Described alkyl can be methyl, isobutyl-, hexafluoro sec.-propyl, cyclohexyl, spiral shell decyl etc., described alkoxyl group can be methoxyl group, propoxy-, diethoxy etc., described aryl can be phenyl, p-Methylisopropylbenzene base, xenyl, carbazyl, naphthyl etc., and described aryloxy can be phenoxy group, hexichol ether, triphen two ethers etc.; Described substituted radical can be halogen atom, Siliciumatom, sulphur atom, cyano group etc.R
5～R
8Can be when being connected on the phenyl ring in any position of phenyl ring.
4 according to the described fluorene-containing polyimide adhesive of claim 1, and the wherein said fluorenes end-capping reagent that contains has following general structure:
Wherein, R
9The divalent group of expression hydrogen atom or aliphatics, alicyclic, aromatic series, carbonyl, ether, sulfuryl.R
10, R
11The univalent perssad of expression hydrogen atom or aliphatics, alicyclic, aromatic series, sulfonic group, halogen formyl radical, carbalkoxy.Specifically, R
9The aliphatics of expression, alicyclic, aromatic series divalent group can be and replace or unsubstituted ring-type, straight or branched alkylidene group, replacement or unsubstituted ring-type, straight or branched alkylene oxide group, replace or unsubstituted arylidene the divalent group of replacement or unsubstituted inferior aryloxy etc.; R
10, R
11The aliphatics of expression, alicyclic, aromatic series can be and replaces or unsubstituted ring-type, straight or branched alkyl, replace or unsubstituted ring-type, straight or branched alkoxyl group, replace or unsubstituted aryl, replace or the univalent perssad of unsubstituted aryloxy etc.Particularly, described alkylidene group can be methylene radical, isobutylidene, hexafluoroisopropyli,ene, cyclohexylidene, inferior spiral shell decyl etc., and described arylidene can be phenylene, to methyl isopropyl phenylene, diphenylene, inferior carbazyl, naphthylidene etc.; Described alkyl can be methyl, isobutyl-, hexafluoro sec.-propyl, cyclohexyl, spiral shell decyl etc., described alkoxyl group can be methoxyl group, propoxy-, diethoxy etc., described aryl can be phenyl, p-Methylisopropylbenzene base, xenyl, carbazyl, naphthyl etc., and described aryloxy can be phenoxy group, hexichol ether, triphen two ethers etc.; Described substituted radical can be halogen atom, Siliciumatom, sulphur atom, cyano group etc.R
9～R
11Can be when being connected on the phenyl ring in any position of phenyl ring.
5 according to the described fluorene-containing polyimide adhesive of claim 1, described other diamine monomer is selected from quadrol, 1, the 4-butanediamine, 1, the 6-hexanediamine, 1, the 8-octamethylenediamine, 1, the 10-decamethylene diamine, mphenylenediamine, Ursol D, 1,3,5-trimethylammonium mphenylenediamine, 2,3,5, the 6-tetramethyl-para-phenylene diamine, 3,4 '-diaminodiphenyl oxide, 4,4 '-diaminodiphenyl oxide, 1,3-two (4-amino-benzene oxygen) benzene, 1,4-two (4 '-amino-benzene oxygen) benzene, 1,4-two (2-trifluoromethyl, 4 '-amino-benzene oxygen) benzene, 4,4 '-diaminodiphenylmethane, 3,3 '-dimethyl-4,4 '-diaminodiphenylmethane, 3,3 '-dimethoxy-4 ', 4 '-diaminodiphenylmethane, 2,2 '-dimethoxy-4 ', 4 '-diaminodiphenylmethane, 2,2 '-tolidine, 3,3 '-tolidine, 2,2 '-two (trifluoromethyl) p-diaminodiphenyl, 2,2 '-two (trifluoromethoxy) p-diaminodiphenyl, 3,3 '-diaminodiphenyl sulfide, 4,4 '-diaminodiphenyl sulfide, 3,3 '-diaminodiphenylsulfone(DDS), 4,4 '-diaminodiphenylsulfone(DDS), 3,3 '-diamino benzophenone, 4,4 '-diamino benzophenone, two (4-ammonia phenoxy groups)-1,4 '-benzene, 2,2 '-(4-aminophenyl) propane, 2,2 '-(4-aminophenyl) HFC-236fa, 2,2 '-(4-ammonia Phenoxyphenyl) HFC-236fa, in the polysiloxane diamine one or more.
6 according to the described fluorene-containing polyimide adhesive of claim 1, and described other dianhydride monomer is selected from pyromellitic acid dianhydride, 2,3,3 ', 4 '-BPDA, 3,3 ', 4,4 '-BPDA, 2,3,3 ', 4 '-phenyl ether tetracarboxylic dianhydride, 3,3 ', 4,4 '-phenyl ether tetracarboxylic dianhydride, 3,3 ', 4,4 '-benzophenone tetracarboxylic dianhydride, triphen diether tetracarboxylic dianhydride, 1,2,3,4-tetracarboxylic butane dianhydride, the tetramethylene tetracarboxylic dianhydride, the pentamethylene tetracarboxylic dianhydride, 2,2 '-two [3,4-two carboxyphenyls] propane dianhydride, 2,2 '-two [4-di carboxyl phenyloxy phenyl] propane dianhydride, 2,2 '-two [3,4-two carboxyphenyls] hexafluoropropane dianhydride, 2,2 '-two [3,4-two carboxyphenyls] ether dianhydride, 2,2 '-two [3,4-two carboxyphenyls] thioether dianhydride, 2,2 '-two [3,4-two carboxyphenyls] the sulfone dianhydride, 2,2 '-two [3,4-two carboxyphenyls] methane dianhydride, 1,4-two [3,4 '-dicarboxyl phenoxy group] benzene dianhydride, 1, two [3 ', the 4-two carboxyphenyls] benzene dianhydrides of 3-, 2,2 '-two [3,4-dicarboxyl phenoxy group-1,4 '-penylene] the propane dianhydride, 4,4 '-two [3,4-dicarboxyl phenoxy group] biphenyl dianhydride, 2,3,6,7-naphthalene tetracarboxylic dianhydride, 1,4,5,8-naphthalene tetracarboxylic dianhydride, sulfobenzide-2,3,3 ', 4 '-tetracarboxylic dianhydride, sulfobenzide-2,2 ', 3,3 '-tetracarboxylic dianhydride, in the anthraquinone tetracarboxylic dianhydride one or more.
7 according to the described fluorene-containing polyimide adhesive of claim 1, described other end-capping reagent is selected from Tetra hydro Phthalic anhydride, aniline, vinyl aniline, acetylene, phenylacetylene, 3-phenylacetylene base aniline, phenylacetylene phthalic anhydride, 5-norbornylene-2,3-dicarboxylic anhydride, 5-norbornylene-2,3-diformate mono acid anhydride etc.
The preparation method of the described fluorene-containing polyimide adhesive of 8 claims 1, it is characterized in that: contain the fluorenediamine monomer, contain the fluorenes dianhydride monomer and/or contain the fluorenes end-capping reagent at least a, be dissolved in the organic solvent with at least a other diamine monomer, other dianhydride monomer and/or other end-capping reagent, at room temperature stir, obtain even polyamic acid; Polyamic acid solution is coated on the sheet glass Kapton of preparation part imidization under the condition of far infrared imidization; Or in polyamic acid solution, add dewatering agent and catalyzer, adopt the chemical imidization legal system to get polyimide powder.
9 a kind of preparation methods of fluorene-containing polyimide adhesive according to Claim 8, it is characterized in that: described organic solvent is selected from N-Methyl pyrrolidone, N, N '-dimethyl formamide, N, one or more in N '-N,N-DIMETHYLACETAMIDE, the meta-cresol.
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