CN109722211A - A kind of BDADDM type silicon-containing adhesive and preparation method thereof - Google Patents
A kind of BDADDM type silicon-containing adhesive and preparation method thereof Download PDFInfo
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- CN109722211A CN109722211A CN201811569508.8A CN201811569508A CN109722211A CN 109722211 A CN109722211 A CN 109722211A CN 201811569508 A CN201811569508 A CN 201811569508A CN 109722211 A CN109722211 A CN 109722211A
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Abstract
The present invention relates to a kind of BDADDM type silicon-containing adhesives and preparation method thereof, by 4,4 '-bis- (2,4- diamino phenoxy) diphenyl-methane BDADDM, maleic anhydride, aromatic diamine, aromatic dicarboxylic acid anhydride and 3- aminopropyltrialkoxysilane reaction product and organic solvent composition.Raw material sources of the invention are convenient, and simple process is easy to operate, and product comprehensive performance is good, can be applied to the bonding of glass, ceramics, composite material, extraordinary polarity weaving prepreg and its composite material base, have good market application prospect.
Description
Technical field
The invention belongs to adhesive area, in particular to a kind of BDADDM type silicon-containing adhesive and preparation method thereof.
Background technique
Adhesive system is widely used in the every field of national economy: either high-technology field or general
Its trace can be seen in technical field, either defence and military or civilian industry or even daily life.
Related adhesive system or containing silicone resin system have had many research reports, also there is many patents of invention:
Chinese invention patent CN102786902A discloses a kind of organosilicon Organic fluoride epoxy adhesive and preparation method thereof.
Yan Rui, Yu Xinhai et al. [preparation of novel epoxy adhesive and performance study, insulating materials, 2012,45 (2):
12-14,18] a kind of neo-epoxy resin adhesive and preparation method thereof is disclosed, and systematic research has been carried out to its performance.
Chinese invention patent CN106220851A discloses a kind of siliceous epoxy acid imide matrix resin of YASI type and its system
Preparation Method.
Yu Xinhai et al. [preparation of organosilicon epoxy system adhesive and performance study, insulating materials, 2012,45 (2):
1-3,11] a kind of adhesive composition of organic siliconresin modified epoxy is disclosed, and its performance is studied, simultaneously
The superior adhesive of comprehensive performance is obtained.
Chinese invention patent CN102220102A discloses a kind of high-temperature-resistant adhesive and preparation method thereof.
Chinese invention patent CN106146841A discloses a kind of preparation of siliceous epoxy acid imide matrix resin of DAHTM type
Method includes the following steps:
(1) by bis- (3- amino-4-hydroxylphenyl) hexafluoropropane of 2,2-, o-cresol, bis- [4- (the 3,4- dicarboxyl benzene of 2,2-
Oxygroup) phenyl] propane dianhydride and maleic anhydride be put into reaction kettle, be passed through nitrogen, stir, be heated to 80 DEG C, be added dropwise different
Quinoline is heated to 100 DEG C -110 DEG C, after being stirred to react 5-12 hours, is cooled to 60 DEG C, reactant is poured into and fills precipitating agent
In precipitating kettle, solids is precipitated in high-speed stirred, and filtering, 80 DEG C are dried in vacuo 10 hours, obtain imide oligomer object；
(2) by 4,4 '-diamino -4 "-hydroxyl triphenylmenthane (DAHTM), epoxy resin is put into reaction kettle, in 80 DEG C -
After 100 DEG C are stirred reaction 0.5-1 hours, imide oligomer object is added and continues to be stirred to react 1-2 hours, 3- ammonia is then added
Propyl trialkoxy silane is stirred to react 5-15 minutes, is cooled to room temperature, is added curing agent, is uniformly mixed.
Chinese invention patent CN102181251A discloses a kind of epoxyn that unsaturated polyimides are modified
And preparation method thereof.
Chinese invention patent CN101649174A discloses a kind of high temperature resistant one-component solvent-free epoxy adhesive and its system
Preparation Method.
Wu Min et al. [development of novel high-strength one-component epoxy resin adhesive, bonding, 2009,30 (9): 54-57]
A kind of epoxy binder in monocomponent in is disclosed, excellent combination property especially has very high tensile shear strength.
Chen Hongjiang et al. [the cure kinetics research of neo-epoxy resin adhesive system, bonding, 2009,30 (8): 43-
45] a kind of epoxyn system is disclosed, and its cure kinetics is studied.
Fei Fei et al. [preparation of high temperature resistant epoxy binder in monocomponent in, bonding, 2009,30 (12): 34-37] discloses one
Kind one-component thermostable epoxy adhesive.
Xu Meifang et al. [the cure kinetics research of polyimide-epoxy resin adhesive, chemistry and bonding, 2011,33
(2): 17-20 a kind of polyimide-epoxy resin adhesive] is disclosed, and cure kinetics research has been carried out to it.
Chinese invention patent CN104844801A discloses a kind of Silicone Containing Polyimides copper coated foil plate, it is characterised in that: by
Copper foil, alkali-free glass cloth and Silicone Containing Polyimides resin composition；Wherein, it is 1:1-5 that Silicone Containing Polyimides resin, which is by mass ratio,
A, B component polymerization reaction and obtain；And component A is reacted with aromatic dianhydride by the organosilicon diamines that molar ratio is 1:2 and is obtained；B
Component is by molar ratio are as follows: the aromatic diamine of 2:1.8-1.9:0.1-0.3 is reacted with aromatic dianhydride, maleic anhydride and obtained.
Chinese invention patent CN101397486A discloses a kind of preparation side of bi-component solvent-free epoxy resin adhesive
Method is primarily characterized in that: it includes component A and B component, and wherein component A contains novolac epoxy resin, alicyclic type epoxy resin
And nbr carboxyl terminal；B component is 4,4 '-bis- (2,4- diamino phenoxy) diphenyl ether aromatic polyvalent amine hardeners.Rouge
The additive amount of ring-like epoxy resin and nbr carboxyl terminal is respectively the 20-35% and 12% (quality hundred of novolac epoxy resin
Score).The additive amount of 4,4 '-bis- (2,4- diamino phenoxy) diphenyl ether aromatic polyvalent amine hardeners is epoxy novolac
Chinese patent CN101397486A discloses a kind of preparation method of bi-component solvent-free epoxy resin adhesive,
Be characterized mainly in that: it includes component A and B component, and wherein component A contains novolac epoxy resin, alicyclic type epoxy resin and end
Carboxy nitrile rubber；B component is bis- (2,4- diamino phenoxy) the benzene aromatic polyvalent amine hardeners of 1,4-.Alicyclic ring type asphalt mixtures modified by epoxy resin
The additive amount of rouge and nbr carboxyl terminal is respectively the 20-35% and 12% (mass percent) of novolac epoxy resin.1,4-
The additive amount of bis- (2,4- diamino phenoxy) benzene aromatic polyvalent amine hardeners is the 15-20% (quality of novolac epoxy resin
Percentage), gained adhesive system good manufacturability.But its heat resistance is ideal not enough.
Yu Xinhai et al. [development [J] of high-temperature resistant single-component epoxy adhesive is bonded, 2008,29 (12): 16-19] is public
The preparation method for having opened a kind of high-temperature resistant single-component epoxy adhesive, is primarily characterized in that: being sealing end with maleic anhydride (MA)
Agent, with bis- [4- (4- amino-benzene oxygen) phenyl] third of bis- (3- amino-4-hydroxylphenyl) hexafluoropropane (BAHPFP) of 2,2-, 2,2-
Bis- [4- (3,4- di carboxyl phenyloxy) phenyl] propane dianhydrides (BPADA) of alkane (BAPOPP), 2,2- are that main Material synthesis obtains
Phenolic hydroxy group polyetherimide resin (HPEI)；With synthesized obtained HPEI for resistant, toughened dose, with N, N, N', N'- tetra-
Glycidyl -4,4'- diaminodiphenylmethane (TGDDM), hydrogenated bisphenol A epoxy resin (HBPAE), latent curing agent
Deng, preparation obtained the high-temperature resistant single-component epoxy adhesive of excellent combination property.
This method, although containing the polyetherimide resin of active reactive group (hydroxyl, unsaturated double-bond) by synthesis
(HPEI), toughening modifying has been carried out to epoxy resin, and has achieved preferable technical effect.But there is also some disadvantages:
(1) reactable group is limited, and the content of especially unsaturated double-bond is relatively low.Because maleic anhydride is as sealing end
Agent come using, the dosage of maleic anhydride is seldom.
The monomers such as bis- (3- amino-4-hydroxylphenyl) hexafluoropropane (BAHPFP) of (2) 2,2- are expensive, lead to polyethers acyl
The cost of imide resin (HPEI) and adhesive is very high, is unfavorable for large-scale promotion application, can only be confined to certain special dimensions.
Summary of the invention
Technical problem to be solved by the invention is to provide a kind of BDADDM type silicon-containing adhesives and preparation method thereof, this contains
Silicon adhesive comprehensive performance is good, can be applied to glass, ceramics, composite material, extraordinary polarity weaving prepreg and its composite wood
Expect the bonding of substrate, there is good market application prospect.
The present invention provides a kind of BDADDM type silicon-containing adhesive, the adhesive is 1:2:5-10:6.5- by molar ratio
Bis- (2,4- diamino phenoxy) the diphenyl-methane BDADDM in the 4,4 ' of 12:1-2-, maleic anhydride, aromatic diamine, aromatic series
The reaction product and organic solvent of dibasic anhydride and 3- aminopropyltrialkoxysilane composition.
The aromatic diamine is selected from m-phenylene diamine (MPD), p-phenylenediamine, 2- methylresorcinol diamines, 2,4,6- trimethyl isophthalic
Diamines, 3,4 '-diaminodiphenyl ethers, 4,4 '-diaminodiphenyl ethers, 3,3 '-diaminodiphenyl ethers, 3,5- diaminobenzoic acid,
4,4 '-benzidines, 3,3 '-dimethyl -4,4 '-benzidine, 4,4 '-diaminodiphenylmethane, 4,4 '-diamino two
Benzene sulfone, 3,3 '-diaminodiphenylsulfones, 3,3 '-dimethyl -4,4 '-diaminodiphenylmethane, 3,3 '-two chloro- 4,4 '-diamino
Diphenyl-methane, 3,3 ', 5,5 '-tetramethyls -4,4 '-diaminodiphenylmethane, 2,6- bis- (4- amino-benzene oxygen) benzonitriles, 2,6-
Bis- (4- amino-benzene oxygen) benzoic acid of bis- (3- amino-benzene oxygen) benzonitriles, 3,5-, 4,4 '-diamino -4 "-hydroxyl triphen first
Alkane, 2- (4- aminophenyl) -5- aminobenzimidazole, 3,3 '-diamino -4,4 '-dihydroxybiphenyl, the bis- (3- amino -4- of 2,2-
Hydroxy phenyl) propane, bis- (3- amino-4-hydroxylphenyl) hexafluoropropane of 2,2-, bis- (3- amino-benzene oxygen) benzene of 1,3-, 1,3- be bis-
Bis- (4- amino-benzene oxygen) benzene of (4- amino-benzene oxygen) benzene, 1,4-, 1,3- bis- (2- trifluoromethyl-4-aminophenoxyl) benzene, 1,
Bis- (2- trifluoromethyl-4-aminophenoxyl) benzene of 4-, bis- (4- amino-benzene oxygen) toluene of 2,6-, 2,5- bis- (4- amino-benzene oxygens)
Bis- (2- trifluoromethyl-4-aminophenoxyl) benzoic acid of toluene, 3,5-, bis- (2- trifluoromethyl-4-aminophenoxyl) first of 2,6-
Bis- (2- trifluoromethyl-4-aminophenoxyl) toluene of benzene, 2,5-, 2,2- bis- [4- (4- amino-benzene oxygen) phenyl] propane, 2,2-
Bis- [4- (2- trifluoromethyl-4-aminophenoxyl) phenyl] propane, 2,2- bis- [4- (3- amino-benzene oxygen) phenyl] propane, 4,
4 '-bis- (4- amino-benzene oxygen) diphenyl-methanes, 4,4 '-bis- (3- amino-benzene oxygen) diphenyl-methanes, 4,4 '-bis- (2- trifluoromethyls-
4- amino-benzene oxygen) diphenyl-methane, bis- [4- (4- amino-benzene oxygen) phenyl] hexafluoropropane of 2,2-, bis- [4- (the 2- fluoroforms of 2,2-
Base -4- amino-benzene oxygen) phenyl] hexafluoropropane, 2,2- bis- [4- (3- amino-benzene oxygen) phenyl] hexafluoropropane, 4,4 '-bis- (4-
Amino-benzene oxygen) diphenyl sulphone (DPS), 4,4 '-bis- (3- amino-benzene oxygen) diphenyl sulphone (DPS)s, 4,4 '-bis- (2- trifluoromethyl -4- aminobenzene oxygen
Base) it is diphenyl sulphone (DPS), 4,4 '-bis- (4- amino-benzene oxygen) diphenyl sulfides, 4,4 '-bis- (3- amino-benzene oxygen) diphenyl sulfides, 4,4 '-bis-
(2- trifluoromethyl-4-aminophenoxyl) diphenyl sulfide, 4,4 '-bis- (4- amino-benzene oxygen) diphenyl ether, 4,4 '-bis- (3- amino
Phenoxy group) diphenyl ether, 4,4 '-bis- (2- trifluoromethyl-4-aminophenoxyl) diphenyl ether, 4,4 '-bis- (4- amino-benzene oxygens) two
Benzophenone, 4,4 '-bis- (3- amino-benzene oxygen) benzophenone, 4,4 '-bis- (2- trifluoromethyl-4-aminophenoxyl) hexichol first
Ketone, 4,4 '-bis- (4- amino-benzene oxygen) biphenyl, 4,4 '-bis- (3- amino-benzene oxygen) biphenyl, 4,4 '-bis- (2- trifluoromethyl -4-
One or more of amino-benzene oxygen) biphenyl.
The aromatic dicarboxylic acid anhydride be selected from pyromellitic acid anhydride, 3,3 ', 4,4 '-tetracarboxylic diphenyl ether dianhydrides, 3,3 ', 4,
Bis- (3,4- dicarboxyphenyi) hexafluoros third of 4 '-tetracarboxylic diphenyl sulfone dianhydrides, 3,3 ', 4,4 '-tetracarboxylic benzophenone dianhydrides, 2,2-
Bis- [4- (3,4- di carboxyl phenyloxy) phenyl] hexafluoropropane dianhydrides of alkane dianhydride, 3,3 ', 4,4 '-tetracarboxylic biphenyl dianhydrides, 2,2-,
Bis- [4- (3,4- di carboxyl phenyloxy) phenyl] propane dianhydrides of 2,2-, 1,4- bis- (3,4- di carboxyl phenyloxy) benzene dianhydrides, 1,3-
Double-(3,4- di carboxyl phenyloxy) benzene dianhydride, 4,4 '-bis- (3,4- di carboxyl phenyloxy) biphenyl dianhydrides, 4,4 '-bis- (3,4- bis-
Carboxyphenoxy) diphenyl sulfone dianhydride, 4,4 '-bis- (3,4- di carboxyl phenyloxy) diphenyl ether dianhydrides, 4,4 '-bis- (3,4- dicarboxyls
Phenoxy group) diphenyl ether dianhydride, one or more of 4,4 '-bis- (3,4- di carboxyl phenyloxy) benzophenone dianhydrides.
The 3- aminopropyltrialkoxysilane is selected from 3- aminopropyl trimethoxysilane, 3- aminopropyl triethoxysilane
One or both of.
The organic solvent is selected from N, N-dimethylformamide, N, N dimethyl acetamide, tetrahydrofuran, methyl tetrahydro furan
It mutters, one or more of n-methyl-2-pyrrolidone, N- ethyl-2-pyrrolidone, dimethyl sulfoxide.
The mass ratio of the organic solvent and reactant is 2.5-9.5:1；Wherein, reactant refers to 4,4 '-bis- (2,4- bis-
Amino-benzene oxygen) diphenyl-methane BDADDM, maleic anhydride, three alcoxyl of aromatic diamine, aromatic dicarboxylic acid anhydride and 3- aminopropyl
Base silane.
The present invention also provides a kind of preparation methods of BDADDM type silicon-containing adhesive, include the following steps:
According to the ratio, 4,4 '-bis- (2,4- diamino phenoxy) diphenyl-methane BDADDM and organic solvent are put into reaction kettle
In, at room temperature after stirring and dissolving, maleic anhydride is added, after being stirred to react 15min-30min at room temperature, aromatic dicarboxylic is added
After stirring and dissolving, aromatic dicarboxylic acid anhydride is added in amine, and after being stirred to react -4.0 hours 1.0 hours at room temperature, 3- aminopropyl three is added
Alkoxy silane is stirred to react -2 hours 0.5 hour at room temperature to get BDADDM type silicon-containing adhesive.
Beneficial effect
(1) present invention has a good hot mechanical performance, and excellent combination property, can be applied to glass, ceramics, compound
The bonding of material, extraordinary polarity weaving prepreg and its composite material base, has good market application prospect；
(2) preparation process of the invention is simple, at low cost, easy to operate, reaction raw materials convenient sources, can set general
Standby middle completion preparation process, is advantageously implemented industrialized production；
(3) 3- aminopropyltrialkoxysilane is introduced in adhesive molecular structure of the invention, provides not only adhesive
The cured crosslinking reactivity group of system, and good anchor cooperation can be generated with substrate and used, to the interface characteristics of improvement bonding plane
It can be of great benefit to adhesive strength.
Specific embodiment
Present invention will be further explained below with reference to specific examples.It should be understood that these embodiments are merely to illustrate the present invention
Rather than it limits the scope of the invention.In addition, it should also be understood that, after reading the content taught by the present invention, those skilled in the art
Member can make various changes or modifications the present invention, and such equivalent forms equally fall within the application the appended claims and limited
Range.
Embodiment 1
By the 4,4 '-of 41.2 grams (0.1 mole) bis- (2,4- diamino phenoxy) diphenyl-methanes (BDADDM) and 1500 grams
N, N dimethyl acetamide are put into reaction kettle, and at room temperature after stirring and dissolving, 19.6 grams of (0.2 mole) maleic anhydrides, stirring is added
After dissolution, after being stirred to react 15min at room temperature, 80.0 grams of (0.4 mole) 3,4 '-diaminodiphenyl ethers and 43.2 gram (0.1 is added
Mole) 4,4 '-bis- (4- amino-benzene oxygen) diphenyl sulphone (DPS)s, after stirring and dissolving, 288.6 grams of (0.65 mole) 2,2- bis- (3,4- are added
Dicarboxyphenyi) hexafluoropropane dianhydride, stirring and dissolving, after being stirred to react 1.0 hours, is added 22.1 grams (0.1 mole) at room temperature
3- aminopropyl triethoxysilane is stirred to react 2 hours at room temperature to get the BDADDM type homogeneous to 1993.7 grams of clear viscous
Silicon-containing adhesive is denoted as SA-1.
Embodiment 2
By the 4,4 '-of 41.2 grams (0.1 mole) bis- (2,4- diamino phenoxy) diphenyl-methanes (BDADDM), 1600 grams of N,
N dimethyl acetamide and 1600 grams of N- ethyl-2-pyrrolidones are put into reaction kettle, at room temperature after stirring and dissolving, are added 19.6
After stirring and dissolving, after being stirred to react 30min at room temperature, 72.5 grams of (0.25 moles) 4 are added in gram (0.2 mole) maleic anhydride,
4 '-diamino -4 "-hydroxyl triphenylmenthane, 110.0 grams of (0.55 mole) 3,4 '-diaminodiphenyl ethers, 31.7 grams (0.1 mole)
Bis- (4- amino-benzene oxygen) benzonitriles of 2,6- and bis- [4- (3- amino-benzene oxygen) phenyl] hexafluoros third of 51.8 grams of (0.1 mole) 2,2-
After stirring and dissolving, 93.0 grams of (0.3 mole) 3,3 ', 4,4 '-tetracarboxylic diphenyl ether dianhydrides, 104.0 grams (0.2 mole) are added in alkane
Bis- [4- (3,4- di carboxyl phenyloxy) phenyl] propane dianhydrides of 2,2- and 225.4 grams of (0.7 mole) 3,3 ', 4,4 '-tetracarboxylics two
Benzophenone dianhydride, stirring and dissolving, after being stirred to react 4.0 hours, is added 44.2 grams of three ethoxies of (0.2 mole) 3- aminopropyl at room temperature
Base silane, is stirred to react 0.5 hour at room temperature to get the BDADDM type silicon-containing adhesive homogeneous to 3992.4 grams of clear viscous,
It is denoted as SA-2.
Embodiment 3
By the 4,4 '-of 41.2 grams (0.1 mole) bis- (2,4- diamino phenoxy) diphenyl-methanes (BDADDM), 1100 grams of N,
N-dimethylformamide and 5000 grams of N- ethyl-2-pyrrolidones are put into reaction kettle, at room temperature after stirring and dissolving, are added 19.6
After stirring and dissolving, after being stirred to react 25min at room temperature, 100.0 grams of (0.5 moles) 3 are added in gram (0.2 mole) maleic anhydride,
4 '-diaminodiphenyl ethers, bis- (4- amino-benzene oxygen) diphenyl sulphone (DPS)s of 43.2 grams of (0.1 moles) 4,4 '-and 41.0 grams of (0.1 moles) 2,
After stirring and dissolving, 62.0 grams of (0.2 mole) 3,3 ', 4,4 '-tetracarboxylics are added in 2- bis- [4- (4- amino-benzene oxygen) phenyl] propane
Diphenyl ether dianhydride and bis- [4- (3, the 4- di carboxyl phenyloxy) phenyl] propane dianhydrides of 338.0 grams of (0.65 mole) 2,2-, at room temperature
After being stirred to react 2.0 hours, 22.1 grams of (0.1 mole) 3- aminopropyl triethoxysilanes and 17.9 grams are added in stirring and dissolving
(0.1 mole) 3- aminopropyl trimethoxysilane is stirred to react 1.5 hours at room temperature to get homogeneous to 6784 grams of clear viscous
BDADDM type silicon-containing adhesive, be denoted as SA-3.
Embodiment 4
The BDADDM type silicon-containing adhesive of suitable 1~embodiment of embodiment 3, i.e. SA-1~SA-3, and difference are taken respectively
It is uniformly applied in standard stainless steel test piece, overlaps, clamp, be put into convection oven and solidified: being started to warm up from room temperature
To 80 DEG C, after being kept for 1 hour, 150 DEG C are continuously heating to, after being kept for 2 hours, is continuously heating to 200 DEG C, after being kept for 0.5 hour,
260 DEG C are continuously heating to, after being kept for 0.5 hour, cooled to room temperature.Using electronic tensile machine, room temperature is carried out to it respectively
Tensile shear strength test under the conditions of (25 DEG C) and high temperature (250 DEG C), the results are shown in Table 1.
The BDADDM type silicon-containing adhesive of suitable 1~embodiment of embodiment 3, i.e. SA-1~SA-3, and difference are taken respectively
It is equably impregnated on glass cloth, is overlapped and clamped with standard stainless steel test piece, be put into convection oven and solidified: being opened from room temperature
Beginning is warming up to 80 DEG C, after being kept for 1 hour, is continuously heating to 150 DEG C, after being kept for 2 hours, is continuously heating to 200 DEG C, keeps 0.5
After hour, 260 DEG C are continuously heating to, after being kept for 0.5 hour, cooled to room temperature.Using electronic tensile machine, respectively to its into
Tensile shear strength test under the conditions of row room temperature (25 DEG C) and high temperature (250 DEG C), the results are shown in Table 1.
Using Guilin Electro Scientific research institute produce megger test its solidfied material volume resistivity ρ v (1MHz, 25
DEG C), the results are shown in Table 1.
The dielectric loss (D) of its solidfied material is tested using the TH2828S tester of Changzhou Tong Hui Electron equipment Co., Ltd
(1MHz, 25 DEG C), the results are shown in Table 1.
Deionized water (25 DEG C) are soaked in after the square coupons weighing (W1) of above-mentioned drying using precision electronic balance
In, it after 72 hours, takes out, dries surface with filter paper, weigh (W2), water absorption rate is calculatedData it is as shown in table 1.
Climatic chamber (85 is placed in after the square coupons weighing (G1) of above-mentioned drying using precision electronic balance
DEG C, RH85%) in, it after 72 hours, takes out, dries surface with filter paper, weigh (G2), the data of hydroscopicity (ψ) are calculated such as
Shown in table 1.
The performance data of table 1BDADDM type silicon-containing adhesive
Claims (7)
1. a kind of BDADDM type silicon-containing adhesive, it is characterised in that: the adhesive is 1:2:5-10:6.5-12 by molar ratio:
Bis- (2,4- diamino phenoxy) the diphenyl-methane BDADDM in the 4,4 ' of 1-2-, maleic anhydride, aromatic diamine, aromatic dicarboxylic
The reaction product and organic solvent of acid anhydride and 3- aminopropyltrialkoxysilane composition.
2. a kind of BDADDM type silicon-containing adhesive according to claim 1, it is characterised in that: the aromatic diamine choosing
From m-phenylene diamine (MPD), p-phenylenediamine, 2- methylresorcinol diamines, 2,4,6- trimethyl m-phenylene diamine (MPD), 3,4 '-diaminodiphenyl ethers, 4,
4 '-diaminodiphenyl ethers, 3,3 '-diaminodiphenyl ethers, 3,5- diaminobenzoic acid, 4,4 '-benzidines, 3,3 '-diformazans
Base -4,4 '-benzidine, 4,4 '-diaminodiphenylmethane, 4,4 '-diaminodiphenylsulfones, 3,3 '-diaminodiphenylsulfones, 3,
3 '-dimethyl -4,4 '-diaminodiphenylmethane, 3,3 '-two chloro- 4,4 '-diaminodiphenylmethane, 3,3 ', 5,5 '-tetramethyls -
Bis- (4- amino-benzene oxygen) benzonitriles of 4,4 '-diaminodiphenylmethane, 2,6-, 2,6- bis- (3- amino-benzene oxygen) benzonitriles, 3,
Bis- (4- amino-benzene oxygen) benzoic acid of 5-, 4,4 '-diamino -4 "-hydroxyl triphenylmenthane, 2- (4- aminophenyl) -5- aminobenzene
And bis- (3- amino-4-hydroxylphenyl) propane of imidazoles, 3,3 '-diamino -4,4 '-dihydroxybiphenyl, 2,2-, bis- (the 3- ammonia of 2,2-
Base -4- hydroxy phenyl) hexafluoropropane, bis- (3- amino-benzene oxygen) benzene of 1,3-, bis- (4- amino-benzene oxygen) benzene of 1,3-, 1,4- be bis-
Bis- (2- trifluoromethyl-4-aminophenoxyl) benzene of (4- amino-benzene oxygen) benzene, 1,3-, the bis- (2- trifluoromethyl -4- aminobenzenes of 1,4-
Oxygroup) benzene, bis- (4- amino-benzene oxygen) toluene of 2,6-, bis- (4- amino-benzene oxygen) toluene of 2,5-, bis- (the 2- trifluoromethyls-of 3,5-
4- amino-benzene oxygen) benzoic acid, bis- (2- trifluoromethyl-4-aminophenoxyl) toluene of 2,6-, the bis- (2- trifluoromethyl -4- of 2,5-
Amino-benzene oxygen) toluene, bis- [4- (4- amino-benzene oxygen) phenyl] propane of 2,2-, the bis- [4- (2- trifluoromethyl -4- amino of 2,2-
Phenoxy group) phenyl] propane, bis- [4- (3- amino-benzene oxygen) phenyl] propane of 2,2-, 4,4 '-bis- (4- amino-benzene oxygen) hexichol first
Alkane, 4,4 '-bis- (3- amino-benzene oxygen) diphenyl-methanes, 4,4 '-bis- (2- trifluoromethyl-4-aminophenoxyl) diphenyl-methanes, 2,
Bis- [4- (4- amino-benzene oxygen) phenyl] hexafluoropropane of 2-, bis- [4- (2- trifluoromethyl-4-aminophenoxyl) phenyl] six of 2,2-
Bis- [4- (3- amino-benzene oxygen) phenyl] hexafluoropropane of fluoro-propane, 2,2-, 4,4 '-bis- (4- amino-benzene oxygen) diphenyl sulphone (DPS)s, 4,4 '-
Bis- (3- amino-benzene oxygen) diphenyl sulphone (DPS)s, 4,4 '-bis- (2- trifluoromethyl-4-aminophenoxyl) diphenyl sulphone (DPS)s, 4,4 '-bis- (4- amino
Phenoxy group) diphenyl sulfide, 4,4 '-bis- (3- amino-benzene oxygen) diphenyl sulfides, 4,4 '-bis- (2- trifluoromethyl -4- aminobenzene oxygen
Base) it is diphenyl sulfide, 4,4 '-bis- (4- amino-benzene oxygen) diphenyl ether, 4,4 '-bis- (3- amino-benzene oxygen) diphenyl ether, 4,4 '-bis-
(2- trifluoromethyl-4-aminophenoxyl) diphenyl ether, 4,4 '-bis- (4- amino-benzene oxygen) benzophenone, 4,4 '-bis- (3- amino
Phenoxy group) benzophenone, 4,4 '-bis- (2- trifluoromethyl-4-aminophenoxyl) benzophenone, 4,4 '-bis- (4- aminobenzene oxygen
Base) biphenyl, 4,4 '-bis- (3- amino-benzene oxygen) biphenyl, one in 4,4 '-bis- (2- trifluoromethyl-4-aminophenoxyl) biphenyl
Kind is several.
3. a kind of BDADDM type silicon-containing adhesive according to claim 1, it is characterised in that: the aromatic dicarboxylic acid anhydride choosing
From pyromellitic acid anhydride, 3,3 ', 4,4 '-tetracarboxylic diphenyl ether dianhydrides, 3,3 ', 4,4 '-tetracarboxylic diphenyl sulfone dianhydrides, 3,3 ',
4,4 '-tetracarboxylic benzophenone dianhydrides, 2,2- bis- (3,4- dicarboxyphenyi) hexafluoropropane dianhydrides, 3,3 ', 4,4 '-tetracarboxylics connection
Bis- [4- (3,4- di carboxyl phenyloxy) phenyl] hexafluoropropane dianhydrides of benzene dianhydride, 2,2-, bis- [4- (the 3,4- dicarboxyl benzene oxygen of 2,2-
Base) phenyl] propane dianhydride, bis- (3,4- di carboxyl phenyloxy) benzene dianhydrides of 1,4-, 1,3- be bis--(3,4- di carboxyl phenyloxy) benzene two
Acid anhydride, 4,4 '-bis- (3,4- di carboxyl phenyloxy) biphenyl dianhydrides, 4,4 '-bis- (3,4- di carboxyl phenyloxy) diphenyl sulfone dianhydrides, 4,
4 '-bis- (3,4- di carboxyl phenyloxy) diphenyl ether dianhydrides, 4,4 '-bis- (3,4- di carboxyl phenyloxy) diphenyl ether dianhydrides, 4,4 '-
One or more of bis- (3,4- di carboxyl phenyloxy) benzophenone dianhydrides.
4. a kind of BDADDM type silicon-containing adhesive according to claim 1, it is characterised in that: three alcoxyl of 3- aminopropyl
Base silane is selected from one or both of 3- aminopropyl trimethoxysilane, 3- aminopropyl triethoxysilane.
5. a kind of BDADDM type silicon-containing adhesive according to claim 1, it is characterised in that: the organic solvent is selected from N,
N-dimethylformamide, N, N dimethyl acetamide, tetrahydrofuran, methyltetrahydrofuran, n-methyl-2-pyrrolidone, N- ethyl-
One or more of 2-Pyrrolidone, dimethyl sulfoxide.
6. a kind of BDADDM type silicon-containing adhesive according to claim 1, it is characterised in that: the organic solvent with react
The mass ratio of object is 2.5-9.5:1；Wherein, reactant refer to 4,4 '-bis- (2,4- diamino phenoxy) diphenyl-methane BDADDM,
Maleic anhydride, aromatic diamine, aromatic dicarboxylic acid anhydride and 3- aminopropyltrialkoxysilane.
7. a kind of preparation method of BDADDM type silicon-containing adhesive as described in claim 1, includes the following steps:
According to the ratio, 4,4 '-bis- (2,4- diamino phenoxy) diphenyl-methane BDADDM and organic solvent are put into reaction kettle, room
After the lower stirring and dissolving of temperature, maleic anhydride is added, after being stirred to react 15min-30min at room temperature, aromatic diamine, stirring is added
After dissolution, aromatic dicarboxylic acid anhydride is added, after being stirred to react -4.0 hours 1.0 hours at room temperature, 3- aminopropyl tri-alkoxy is added
Silane is stirred to react -2 hours 0.5 hour at room temperature to get BDADDM type silicon-containing adhesive.
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Application publication date: 20190507 |