CN105669738A - Preparation method of modified silane coupling agent - Google Patents
Preparation method of modified silane coupling agent Download PDFInfo
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- CN105669738A CN105669738A CN201610033017.6A CN201610033017A CN105669738A CN 105669738 A CN105669738 A CN 105669738A CN 201610033017 A CN201610033017 A CN 201610033017A CN 105669738 A CN105669738 A CN 105669738A
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/1608—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes the ligands containing silicon
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
- B01J2231/4277—C-X Cross-coupling, e.g. nucleophilic aromatic amination, alkoxylation or analogues
Abstract
A preparation method of a modified silane coupling agent comprises: (1), dissolving mono-anhydride or tetracid dianhydride in glacial acetic acid, adding allylamine according to a molar ratio of the mono-anhydride or tetracid dianhydride to the allylamine being 1:1 or 1:2, stirring and reflowing for 3-24 h, adding water, filtering, washing, and drying to obtain an imide product; (2), dissolving the imide product in an aprotic solvent of medium polarity, adding 0.2 ml or 0.35 ml of a catalyst and trialkoxysilane according to a molar ratio to the imide product being 1:1 or 2:1, and reacting at 50-70 DEG C for 5-48 h, distilling at reduced pressure to remove a low-boiling-point fraction to obtain a product.Least catalyst is used at the premise of ensuring optimal catalytic efficiency so that lowest production cost is achieved.
Description
Technical field
The invention belongs to silane coupling agent and preparation field.
Background technology
Addition reaction of silicon with hydrogen is the important means of preparation carbon functional group's organosilane monomer and organosilicon polymer, and many organosilane monomers containing functional group and organosilicon polymer are all by this Reactive Synthesis. Compared with additive method (direct synthesis technique, organometallic compound method, pyrocondensation legal), the product kind that Si?H addition reaction can synthesize is the abundantest, and have reaction temperature and, it is easy to control, side reaction is few, the advantages such as product is pure, therefore addition reaction of silicon with hydrogen studies maximum, a most widely used class reaction in organosilicon chemistry. Six during the last ten years, and the addition reaction of silicon with hydrogen of carbon-carbon and carbon-heteroatom multiple bond is not only extensively studied in laboratory, has also been widely used in industrial production field.
The material that addition reaction of silicon with hydrogen has catalytic activity mostly is compound or the complex compound of VIII race's metal, some researchs afterwards show, addition reaction of silicon with hydrogen is also had good catalytic activity by VII race's metallic compound and some rare earth compounds, and conventional metal has platinum, palladium, rhodium, ruthenium, copper, iron, manganese, nickel, cobalt, tungsten, molybdenum, actinium series and lanthanide series metal.
Since nineteen forty-seven Sommer etc. finds addition reaction of silicon with hydrogen, transition metal-catalyzed addition reaction of silicon with hydrogen has particularly been carried out big quantifier elimination by this reaction by people, and has made great progress. But owing to reaction preference is not high, especially it is difficult to avoid the polyreaction of unsaturated compound to occur in some systems so that its application is subject to many restrictions, and around this reaction, this scientist is expanded a series of research.
At present, in the research of catalyst for addition reaction of hydrogen and silicon, the most comprehensive class catalyzer studied by platinum catalyst.
Mention in a lot of patent with catalyzer as Si?H addition reaction of the metals such as platinum and salt thereof, relating to what study in this respect the earliest is one section of French Patent, it claims to select element from IIIA, IVA, IB of the periodic table of elements and Group IIB, can as the effective catalyst of addition reaction of silicon with hydrogen with their compound and salt thereof, metal in VIII and salt thereof also can catalyzing addition reaction of silicon with hydrogen effectively, but the document does not provide concrete example. Nineteen fifty-three, platinum is studied in detail by Wagner and Strother as catalyzer, and reporting can the addition reaction of catalyzed alkene and trichlorosilane alkane effectively with platinum black, platinized asbestos and platinum silicon.Subsequently, Wagner report points out that platinum is adsorbed onto on charcoal unusual catalytic activity, the addition reaction of its energy catalysis trichlorosilane alkane and acetylene, ethene, divinyl, propenyl chloride and vinylidene, some reactions just can carry out at 130 DEG C, but great majority reaction only at high temperature just can carry out.
Although determine transition metal can catalyzing addition reaction of silicon with hydrogen effectively, but owing to existing the defect such as catalyst levels is big, catalytic selectivity is not high, low conversion rate, this reaction is also not suitable for dropping into industrial production. Therefore, people seek a kind of desirable catalyzer, and its Neng Shi functional group adds to desired position, and process is gentle, the enough low generation to reduce side reaction of temperature of reaction.
Nineteen fifty-seven, Speier finds chloroplatinic acid hydrate (H2PtCl6·6H2O) aqueous isopropanol can catalyzing addition reaction of silicon with hydrogen, be a kind of very effective homogeneous phase catalyst for addition reaction of hydrogen and silicon (being named as Speier catalyzer afterwards). Before this, addition reaction of silicon with hydrogen adopts superoxide and precious metal to make catalyzer usually, it may also be useful to there is the problems such as receipts rate is low, poor compatibility during this kind of catalyzer, the discovery of Speier catalyzer drastically increases receipts rate and the speed of response of addition reaction of silicon with hydrogen.
But, it is big still to there is catalyst levels in Speier catalyzer, and the selectivity of target product is lower, and some reaction is not had the shortcomings such as catalytic activity. Research finds, adds speed and selectivity that some auxiliary agents can improve addition reaction of silicon with hydrogen. But, these auxiliary agent distinct that Si?H addition reaction is favourable, to such an extent as to reaction is served promoter action by the auxiliary agent that cannot determine which kind of structure or character. Even it is difficult to determine which is definitely specifically reacted by a kind of auxiliary agent work, because reaction is also relevant with the structures and characteristics containing hydrogen silica reagent, unsaturated reagent and catalyzer. As: weakly alkaline amine can promote the addition reaction of trichlorosilane alkane and propenyl chloride, but dichloromethylsilane and propenyl chloride reaction then need the amine (such as tributylamine) that a kind of alkalescence is stronger just reaction to be had promoter action, alkaline carbonate or having of supercarbonate are beneficial to allyl amine and organoalkoxysilane reaction. Other auxiliary agent also has: phosphuret-(t)ed hydrogen, oxygen, oxygen containing organism comprise aldehyde and beta-unsaturated ketone, the tin cobalt compound of organic or inorganic and other some organism such as alcohol, glycol, ether, ester etc. A lot of auxiliary agent can promote addition reaction of silicon with hydrogen, but the purposes of these auxiliary agents is but very narrow, and a kind of reaction that mostly can only a kind of silicon hydrogen reagent and a kind of unsaturated reagent be occurred is worked. The generation of side reaction also can reduce product rate and the selectivity of reaction in addition, such as polyreaction and isomerization. People want to improve reaction yield, speed and selectivity, will reduce the generation of these side reactions.
1973, Karstedt found zeroth order platinum complex catalyst, substantially increased the catalytic efficiency of platinum catalyst in addition reaction of silicon with hydrogen and range of application. Zeroth order platinum complex catalyst is commonly referred to Karstedt type catalyst, normally with the siloxanes or the polysiloxane reaction that are connected with vinyl on platinum halogenide and Si in alcohol, then with the platinum complex that sodium carbonate or sodium bicarbonate neutralize, benzene is obtained after washing. Speier catalyzer and Karstedt catalyzer are all homogeneous catalysts, but the latter is higher than the former catalytic efficiency, it may also be useful to scope is wide and consumption is few, so application at present is widely.The discovery of Karstedt catalyzer, makes a major progress again of catalyst for addition reaction of hydrogen and silicon research field.
Summary of the invention
It is an object of the invention to provide the preparation method of a kind of silane coupling agent using new catalyst synthesis to contain imide ring structural unit.
The typical molecular structural formula of modified silane coupler of the present invention is:
Or
Wherein, R1For methyl or ethyl; R2For single acid anhydride; R3It is four acid dianhydrides.
Described single acid anhydride comprises phthalic anhydride, MALEIC ANHYDRIDE, 1, 2, 3, 6-Tetra Hydro Phthalic Anhydride, 3-methyl isophthalic acid, 2, 3, 6-Tetra Hydro Phthalic Anhydride, 3, 6-ring oxygen-1, 2, 3, 6-Tetra Hydro Phthalic Anhydride, two ring [2, 2, 1]-1-alkene-3, 4-dicarboxylic acid anhydride, 4-phenylacetylene base-1, 2-phthalate anhydride, 3-phenylacetylene base-1, 2-phthalate anhydride, itaconic anhydride, 1, 2, 5, 6-tetrahydrochysene-1, 1-phthalate anhydride, 4-methyl isophthalic acid, 2, 5, 6-tetrahydrochysene-1, 1-phthalate anhydride, 3, 6-ring oxygen-1, 2, 3, 6-tetrahydrochysene-1, 1-phthalate anhydride, two ring [2, 2, 1]-1-alkene-3, 3-dicarboxylic acid anhydride,
Four described acid dianhydrides comprise pyromellitic acid dianhydride, 3, 3 ', 4, 4 '-biphenyl tetracarboxylic dianhydride, 3, 3 ', 4, 4 '-benzophenone tetracarboxylic dianhydride, 3, 3 ', 4, 4 '-hexichol thioether tetracarboxylic dianhydride, 3, 3 ', 4, 4 '-phenyl ether tetracarboxylic dianhydride, 2, 2 ', 3, 3 '-benzophenone tetracarboxylic dianhydride, 2, 2 ', 3, 3 '-biphenyl tetracarboxylic dianhydride, 1, 3-two (3, 4-di carboxyl phenyloxy) benzene dianhydride, 1, 4-two (3, 4-di carboxyl phenyloxy) benzene dianhydride, 1, two [the 2-(3 of 3-, 4-di carboxyl phenyloxy)-2-propyl group] benzene dianhydride, 1, two [the 2-(3 of 4-, 4-di carboxyl phenyloxy)-2-propyl group] benzene dianhydride, sulphur-4, 4 '-bis-phthalic acid two acid anhydride, sulphur-3, 3 '-bis-phthalic acid two acid anhydride, two [3-(3, 4-di carboxyl phenyloxy) phenyl] methane two acid anhydride, the fluoro-pyromellitic dianhydride of 3-, 3, the fluoro-pyromellitic dianhydride of 6-bis-, 3, two (the trifluoromethyl)-pyromellitic dianhydride of 6-, two (3, 4-di carboxyl phenyloxy) dimethylsilane two acid anhydride, 1, 3-two (3, 4-di carboxyl phenyloxy)-1, 1, 3, 3-tetramethyl disiloxane two acid anhydride.
Preparation method of the present invention is two-step synthesis method: imidization reaction and addition reaction of silicon with hydrogen.
(1) being dissolved in glacial acetic acid by list acid anhydride or four acid dianhydrides, be that 1:1 or 1:2 adds allyl group ammonia by the mol ratio of single acid anhydride or four acid dianhydrides and allyl group ammonia, stirring and refluxing 3 ~ 24h, adds water, and filters, and washing is dry, obtains imidization product;
(2) imidization product is dissolved in the aprotic solvent of middle polarity, add 0.2ml or 0.35ml catalyzer and imidization product mol ratio is the trialkoxy silane of 1:1 or 2:1, reacting 5 ~ 48h under 50 ~ 70 DEG C of conditions, low boiler cut is gone out in underpressure distillation, obtains product.
The aprotic solvent of described middle polarity can be benzene, toluene, tetrahydrofuran (THF), pimelinketone, glycol dimethyl ether or dimethyl phthalate etc.
Described catalyzer to be massfraction be 0.520% Karstedt type platinum catalyst, its part is the mixture of allyl group triethoxyl silane and diallyl diethoxy silane 1:1 composition in molar ratio.
Described trialkoxy silane is Trimethoxy silane or triethoxyl silane.
Described single acid anhydride structural unit is preferably as follows structure: phthalic anhydride, MALEIC ANHYDRIDE, 1,2,3,6-Tetra Hydro Phthalic Anhydride.
Four described acid dianhydride structural units are preferably as follows structure: pyromellitic acid dianhydride, 3,3 ', 4,4 '-biphenyl tetracarboxylic dianhydride, 3,3 ', 4,4 '-hexichol thioether tetracarboxylic dianhydride, 3,3 ', 4,4 '-phenyl ether tetracarboxylic dianhydride.
The present invention discloses the novel process that a kind of new catalyst is selected in the use of addition reaction of silicon with hydrogen and usage quantity optimal conditions, this technique is based on a class novel catalytic reaction system, when ensureing catalytic efficiency optimum, it may also be useful to minimum catalyzer, thus reach the object that production cost is minimum.
Embodiment
Below in conjunction with concrete enforcement, the present invention is described further.
Embodiment 1.
Under nitrogen atmosphere, in the three-necked bottle of 250ml, add 14.8g(0.1mol) phthalic anhydride and 150ml glacial acetic acid, dropwise add 5.7g(0.1mol until completely dissolved under whipped state) allyl amine, react 1h under room temperature, then it is warming up to 110 DEG C of reaction backflow 3h. Stopped reaction, to be cooled after room temperature, pour in 300ml water, adularescent precipitation precipitates out immediately, takes out filter, washes filter cake with water three times, obtains white powder product (A1) 15.8g after oven dry, and receipts rate is 85%.
Under nitrogen atmosphere, 250ml three-necked bottle adds 9.35g(0.05mol) A1 and 150ml benzene, the novel Karstedt catalyzer that 0.2ml massfraction is 0.520% is added after stirring and dissolving, 50 DEG C of activation 30min, then 8.2g(0.05mol is added) triethoxyl silane, it is warming up to 70 DEG C, boils off solvent after reaction 10h and obtain canescence oily liquids, use methylene dichloride: methyl alcohol=1:3(V/V) cross post obtain product (A2) 16.2g, receipts rate is 92.5%.
Embodiment 2.
Under nitrogen atmosphere, the three-necked bottle of 250ml adds 10g(0.102mol) norbornylene list acid anhydride and 150ml glacial acetic acid, 5.82g(0.102mol is dropwise added until completely dissolved under whipped state) allyl amine, reacts 1h under room temperature, is then warming up to 110 DEG C of reaction backflow 5h. Stopped reaction, to be cooled after room temperature, pour in 300ml water, adularescent precipitation precipitates out immediately, takes out filter, washes filter cake with water three times, obtains white powder product (B1) 12.45g after oven dry, and receipts rate is 89%.
Under nitrogen atmosphere, 250ml three-necked bottle adds 15g(0.11mol) B1 and 150ml toluene, the novel Karstedt catalyzer that 0.2ml massfraction is 0.520% is added after stirring and dissolving, 50 DEG C of activation 30min, then 13.37g(0.11mol is added) Trimethoxy silane, it is warming up to 70 DEG C, boils off solvent after reaction 18h and obtain pale yellow oily liquid body, use ethyl acetate: sherwood oil=5:1(V/V) cross post obtain product (B2) 23.2g, receipts rate is 81.8%.
Embodiment 3.
Under nitrogen atmosphere, the three-necked bottle of 250ml adds 15g(0.099mol) 1,2,3,6-Tetra Hydro Phthalic Anhydride and 150ml glacial acetic acid, 5.63g(0.099mol is dropwise added until completely dissolved under whipped state) allyl amine, reacts 1h under room temperature, is then warming up to 110 DEG C of reaction backflow 6h. Stopped reaction, to be cooled after room temperature, pour in 300ml water, adularescent precipitation precipitates out immediately, takes out filter, washes filter cake with water three times, obtains white powder product 14.85gC1 after oven dry, and receipts rate is 78.8%.
Under nitrogen atmosphere, 250ml three-necked bottle adds 12g(0.063mol) C1 and 150ml tetrahydrofuran (THF), the novel Karstedt catalyzer that 0.2ml massfraction is 0.520% is added after stirring and dissolving, 50 DEG C of activation 30min, then 10.3g(0.063mol is added) Trimethoxy silane, it is warming up to 70 DEG C, boils off solvent after reaction 24h and obtain pale yellow oily liquid body, use ethyl acetate: sherwood oil=5:3(V/V) cross post obtain product (C2) 14.54g, receipts rate is 65.2%.
Embodiment 4.
Under nitrogen atmosphere, the three-necked bottle of 500ml adds 21.8g (0.1mol) pyromellitic acid anhydride and 300ml Glacial acetic acid, stirring adds 11.4g (0.2mol) allyl amine after making it dissolve, room temperature reaction 1h, reflux 8h, 200ml water is added after being cooled to room temperature, namely adularescent needle-like solid precipitates out, and takes out filter, washing, with obtaining 26.6g solid D1, product rate 90% after trichloromethane recrystallization.
The three-necked bottle of 250ml adds 14.8g (0.05mol) D1 and 100ml glycol dimethyl ether, after stirring makes it dissolve, add the novel Karstedt catalyzer that 0.35ml massfraction is 0.520%, lead to into argon gas, 50 DEG C of activation 30min, add 16.42g (0.1mol) triethoxyl silane, after adding, it is warming up to 70oC, steams solvent, ethyl alcohol recrystallization after reaction 15h, obtains product (D2) 22.47g, product rate 72%.
Embodiment 5.
Under nitrogen atmosphere, 250ml three-necked bottle adds 29.4g (0.1mol) 3,3 ', 4,4 '-biphenyl tetracarboxylic dianhydride, add 150ml Glacial acetic acid again, treat 3,3 ', 4,4 '-biphenyl tetracarboxylic dianhydride adds 11.41g (0.2mol) allyl amine, room temperature reaction 1h, reaction solution reflux 3h after dissolving wherein. Cooling, pours in cold water, collects solid and washes with water, and by recrystallizing methanol, 60 DEG C of vacuum-dryings, obtain 30.21g white crystal E1, and product rate is 81.2%.
250ml three-necked bottle adds 1.94g (0.005mol) E1, add 150ml toluene again, after its dissolving, add the novel Karstedt catalyzer that 0.35ml massfraction is 0.520% wherein, lead to into nitrogen, 50 DEG C of reaction 30min, 1.65g (0.01mol) triethoxyl silane is added again in reaction solution, being warming up to 70 DEG C, backflow 12h, filtrate is revolved after steaming with ethyl alcohol recrystallization, obtaining product (E2) 3.08g, product rate is 86%.
Embodiment 6.
Under nitrogen atmosphere, the three-necked bottle of 500ml adds 16.3g (0.05mol) 3,3 ', 4,4 '-hexichol thioether tetracarboxylic dianhydride and 200ml Glacial acetic acid, add 5.7g (0.1mol) allyl amine, room temperature reaction 1h after stirring and dissolving, reflux 8h, add 1000ml water adularescent solid after being cooled to room temperature to precipitate out, take out filter, washing, solid is with obtaining 19g product F1, product rate 92% after trichloromethane recrystallization.
The three-necked bottle of 500ml adds 20.2g (0.05mol) F1 and 300ml benzene, stir entirely molten after add the novel Karstedt catalyzer that 0.35ml massfraction is 0.520%, lead to into argon gas, 50 DEG C of activation 30min, being warming up to 70 DEG C after adding 16.5g (0.1mol) triethoxyl silane, reaction 18h, boils off solvent, with obtaining 17.4g product F2 after trichloromethane recrystallization, product rate 46%.
Embodiment 7.
Under nitrogen atmosphere, 500ml three-necked bottle adds 15.51g (0.05mol) 3,3 ', 4,4 '-phenyl ether tetracarboxylic dianhydride, then add 150ml Glacial acetic acid, add 5.709g (0.1mol) allyl amine until completely dissolved wherein, room temperature reaction 1h, reaction solution reflux 10h. Cooling, pours in cold water, collects solid and washes with water, and by recrystallizing methanol, 60 DEG C of vacuum-dryings, obtain 16.31g(84%) white crystal G1, product rate is 84%.
250ml three-necked bottle adds 1.94g (0.005mol) G1, add 300ml Glacial acetic acid again, after its dissolving, add the novel Karstedt catalyzer that 0.35ml massfraction is 0.520% wherein, lead to into nitrogen, 50 DEG C of reaction 30min, in reaction solution, add 1.65g (0.01mol) triethoxyl silane again, it is warming up to 70 DEG C, backflow 12h, filtrate obtains white solid after revolving steaming, ethyl alcohol recrystallization, obtains product (G2) 3.08g, and product rate is 86%.
The present invention discloses a kind of new synthetic process being prepared imide ring modified silane coupler about use new catalyst by addition reaction of silicon with hydrogen, this technique is based on a novel Karstedt catalyst system of class, when optimizing catalytic efficiency, use minimum catalyst levels, thus reach reduction production cost.
Claims (6)
1. a preparation method for modified silane coupler, the molecular structural formula of described modified silane coupler is:
Or
Wherein, R1For methyl or ethyl; R2For single acid anhydride; R3It is four acid dianhydrides;
It is characterized in that comprising the steps:
(1) being dissolved in glacial acetic acid by list acid anhydride or four acid dianhydrides, be that 1:1 or 1:2 adds allyl group ammonia by the mol ratio of single acid anhydride or four acid dianhydrides and allyl group ammonia, stirring and refluxing 3 ~ 24h, adds water, and filters, and washing is dry, obtains imidization product;
(2) imidization product is dissolved in the aprotic solvent of middle polarity, add 0.2ml or 0.35ml catalyzer and imidization product mol ratio is the trialkoxy silane of 1:1 or 2:1, reacting 5 ~ 48h under 50 ~ 70 DEG C of conditions, low boiler cut is gone out in underpressure distillation, obtains product.
2. preparation method according to claim 1, is characterized in that the aprotic solvent of described middle polarity is benzene, toluene, tetrahydrofuran (THF), pimelinketone, glycol dimethyl ether or dimethyl phthalate.
3. preparation method according to claim 1, it is characterized in that described catalyzer to be massfraction be the Karstedt type platinum catalyst of 0.520%, its part is the mixture of allyl group triethoxyl silane and diallyl diethoxy silane 1:1 composition in molar ratio.
4. preparation method according to claim 1, is characterized in that described trialkoxy silane is Trimethoxy silane or triethoxyl silane.
5. preparation method according to claim 1, is characterized in that described single acid anhydride is phthalic anhydride, MALEIC ANHYDRIDE or 1,2,3,6-Tetra Hydro Phthalic Anhydride.
6. preparation method according to claim 1, is characterized in that four described acid dianhydrides are pyromellitic acid dianhydride, 3,3 ', 4,4 '-biphenyl tetracarboxylic dianhydride, 3,3 ', 4,4 '-hexichol thioether tetracarboxylic dianhydride or 3,3 ', 4,4 '-phenyl ether tetracarboxylic dianhydride.
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| CN108299349A (en) * | 2018-02-11 | 2018-07-20 | 常熟联邦化工股份有限公司 | Pyromellitic acid anhydride oxidized waste water Resource comprehensive utilization device |
| CN110499026A (en) * | 2019-07-08 | 2019-11-26 | 苏州固泰新材股份有限公司 | Modified liquid crystal polymer film and its preparation method and application |
| CN111777890A (en) * | 2020-07-15 | 2020-10-16 | 武汉材料保护研究所有限公司 | High-temperature-resistant coating adhesion promoter for titanium alloy and preparation method thereof |
| CN115636847A (en) * | 2022-12-23 | 2023-01-24 | 明士(北京)新材料开发有限公司 | Modified silane coupling agent, preparation method thereof and application of modified silane coupling agent in positive photosensitive resin composition |
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