CN103665020A - Preparation method of silane coupling agent with imide cycle structural unit - Google Patents
Preparation method of silane coupling agent with imide cycle structural unit Download PDFInfo
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Abstract
The invention discloses a preparation method of a silane coupling agent with an imide cycle structural unit. The preparation method comprises the following steps: (1) dissolving cyclic anhydride into glacial acetic acid, adding allylamine according to the mole ratio (1:1 or 2:1) of cyclic anhydride to allylamine, refluxing for 2-36h while stirring, adding water, filtering and drying to obtain an imidization product; (2) dissolving the imidization product into benzene or methylbenzene, adding trialkoxysilane with the molar concentration of 0.01-0.05mol/l, reacting at the temperature of 50-90 DEG C for 2-10h, and removing fractions with low boiling points through reduced pressure distillation to obtain the silane coupling agent with the imide cycle structural unit, wherein the trialkoxysilane contains a platinum catalyst, and the mole ratio of trialkoxysilane to the imidization product is 1:1 or 2:1. According to the invention, the silane coupling agent with the imide cycle structural unit is synthesized by taking cyclic anhydride, allylamine and trialkoxysilane as reactants through a two-step method, and an expensive chemical drying agent is not needed to be added in the process, so that the cost is low; moreover, the preparation method is simple in synthesis process and high in yield, and the silane coupling agent with the imide cycle structural unit is easy to purify.
Description
Technical field
The invention belongs to silane coupling agent and preparation field.
Background technology
Silane coupling agent, as the Si great branch of organosilicon industry, is mainly used as the tackifier of surface treatment, Inorganic Fillers Filled plastics, sealing agent, caking agent and coating.General silane coupling agent is at lesser temps (200
oc) under, have good application performance, at high temperature silane coupling agent can decompose, and loses using value, and silane coupling agent is as very important material auxiliary agent, and its resistance toheat affects the thermal characteristics of whole material to a great extent.
Imide ring has plane symmetry ring texture, and bond distance and bond angle are all in standard state, and this makes it have very high thermostability; Simultaneously, imide ring has very strong polarity, the interaction that can produce some strength with treated material surface, therefore, in molecular structure, introduce imide ring, can effectively improve the thermal characteristics of silane coupling agent and application performance (Lu Fengcai, Yang Guisheng. high-temperature resistance adhesive. Beijing: Science Press, 1993; Ding Mengxian, He Tianbai. Polyimide Materials. Beijing: Science Press, 1998).
Prepare the above-mentioned silane coupling agent containing imide ring structure, generally adopt a step imidization method.Detailed says, cyclic anhydride and aminosilane are joined in organic solvent, stirring and dissolving, add diacetyl oxide and triethylamine, after reacting completely, low boiling component is removed in decompression, obtain product, for preventing silane hydrolyzate, the water producing in reaction must be removed, generally to add chemical drier, as: hexamethyldisilazane, trimethyl silyl nitride, but these siccative are very expensive, should use too high (the Ben Patel of cost, Niskayuna. Process for preparing unsaturated imidoalkoxysilanes. US 2007101-23728, 2007-05-30).
Summary of the invention
The preparation method who the object of this invention is to provide a kind of silane coupling agent containing imide ring structural unit.
The molecular structural formula of the silane coupling agent containing imide ring structural unit of the present invention is.
In formula, a is the single silane coupling agent molecular structural formula containing imide ring structural unit, and b is the two silane coupling agent molecular structural formulas containing imide ring structural unit, R
1for methyl or ethyl; R
2for benzene, hexahydrobenzene, norbornylene or ethene; R
3for benzene, biphenyl, benzophenone or phenyl ether.
Preparation method of the present invention adopts two step synthesis methods.
(1) cyclic anhydride being dissolved in Glacial acetic acid, is that 1:1 or 2:1 add allyl amine by the mol ratio of cyclic anhydride and allyl amine, and stirring and refluxing 2 ~ 36h, adds water, filters, dry, obtains imidization product.
(2) imidization product is dissolved in benzene or toluene, add volumetric molar concentration be 0.01mol/l ~ 0.05mol/l catalyst made from platonic, with imidization product mol ratio be the trialkoxy silane of 1:1 or 2:1, in temperature 50 ~ 90
ounder C condition, react 2 ~ 10h, low boiler cut is removed in underpressure distillation, obtains product.
Described cyclic anhydride is phthalic anhydride, HHPA, norbornylene list acid anhydride, MALEIC ANHYDRIDE, pyromellitic acid dianhydride, BPDA, benzophenone tetracarboxylic dianhydride or phenyl ether tetracarboxylic dianhydride.
Described trialkoxy silane is Trimethoxy silane or triethoxyl silane.
Advantage of the present invention is: take cyclic anhydride, allyl amine and trialkoxy silane as reactant, by two step synthesis a kind of silane coupling agent that contains imide ring structural unit, in process, needn't add expensive chemical drier, cost is low, and synthesis technique is simple, productive rate is high, and product is easily purified.
Embodiment
Below in conjunction with concrete enforcement, further illustrate the present invention.
Embodiment 1.
Take phthalic anhydride, allyl amine and triethoxyl silane prepares the method for silane coupling agent as raw material:
1) preparation of catalyst made from platonic
Get 1g Platinic chloride and be dissolved in anhydrous isopropyl alcohol, constant volume in 50ml volumetric flask, volumetric molar concentration is 0.0386mol/l.
2) preparation of imidization product
In dry 500ml three-necked bottle, add 14.8g (0.1mol) Tetra hydro Phthalic anhydride and 180ml Glacial acetic acid, after stirring and dissolving, add 5.7g (0.1mol) allyl amine, room temperature reaction 1h, reflux 4h, adds 170ml water after being cooled to room temperature, be heated to boil, be cooled to room temperature, adularescent solid is separated out, suction filtration, washing, solid Gossypol recrystallized from chloroform, obtains 17.2g product, productive rate 92%, m.p.:69 ~ 71
oc.
3) preparation of final product
In dry 250ml three-necked bottle, add 7.4g (0.05mol) imidization product and 100ml benzene, after stirring and dissolving, add 0.06ml catalyst made from platonic, after argon gas is fully replaced, 50
oc activates 30min, adds 8.21g (0.05mol) triethoxyl silane, after adding, is warming up to 70
oc, reaction 3h, is cooled to room temperature, revolves desolventizing, obtains weak yellow liquid, and methyl alcohol/chloroform is crossed post (1:9, v/v), obtains 9.8g product, productive rate 56%.
Embodiment 2.
Take norbornylene list acid anhydride, allyl amine and triethoxyl silane prepares the method for silane coupling agent as raw material:
1) preparation of catalyst made from platonic.
Get 1g Platinic chloride and be dissolved in anhydrous isopropyl alcohol, constant volume in 50ml volumetric flask, volumetric molar concentration is 0.0386mol/l.
2) preparation of imidization product.
In dry 500ml three-necked bottle, add 16.4g (0.1mol) norbornylene list acid anhydride and 180ml Glacial acetic acid, after stirring and dissolving, add 5.7g (0.1mol) allyl amine, room temperature reaction 1h, reflux 24h, adds 170ml water after being cooled to room temperature, be heated to boil, be cooled to room temperature, have faint yellow solid to separate out, suction filtration, washing, solid sherwood oil recrystallization, obtains 8.1g product, productive rate 40%.
3) preparation of final product.
In dry 250ml three-necked bottle, add 10.2g (0.05mol) imidization product and 100ml benzene, after stirring and dissolving, add 0.06ml catalyst made from platonic, after argon gas is fully replaced, 50
oc activates 30min, adds 8.21g (0.05mol) triethoxyl silane, after adding, is warming up to 70
oc, reaction 3h, is cooled to room temperature, revolves desolventizing, obtains weak yellow liquid, and petrol ether/ethyl acetate is crossed post (1:5, v/v), obtains 7.9g product, productive rate 43%.
Embodiment 3.
1) preparation of catalyst made from platonic.
Get 1g Platinic chloride and be dissolved in anhydrous isopropyl alcohol, constant volume in 50ml volumetric flask, volumetric molar concentration is 0.0386mol/l.
2) preparation of imidization product.
In dry 500ml three-necked bottle, add 14.7g (0.05mol) BPDA and 300ml Glacial acetic acid, after stirring and dissolving, add 5.7g (0.1mol) allyl amine, room temperature reaction 1h, reflux 4h, adds 300ml water after being cooled to room temperature, be heated to boil, be cooled to room temperature, adularescent solid is separated out, suction filtration, washing, solid chloroform/acetone recrystallization, obtains 16.7g product, productive rate 90%.
3) preparation of final product.
In dry 500ml three-necked bottle, add 1.86g (0.005mol) imidization product and 300ml benzene, stir and entirely to add 0.12ml catalyst made from platonic after molten, after argon gas is fully replaced, 50
oc activates 30min, adds 1.64g (0.01mol) triethoxyl silane, after adding, is warming up to 70
oc, reaction 3h, is cooled to room temperature, revolves desolventizing, obtains gray solid, and ethyl alcohol recrystallization, obtains 1.65g product, productive rate 47%.
Embodiment 4.
1) preparation of catalyst made from platonic.
Get 1g Platinic chloride and be dissolved in anhydrous isopropyl alcohol, constant volume in 50ml volumetric flask, volumetric molar concentration is 0.0386mol/l.
2) preparation of imidization product.
In dry 500ml three-necked bottle, add 15.42g (0.1mol) HHPA and 180ml Glacial acetic acid, after stirring and dissolving, add 5.7g (0.1mol) allyl amine, room temperature reaction 1h, reflux 4h, adds 170ml water after being cooled to room temperature, be heated to boil, be cooled to room temperature, have pale solid to separate out, suction filtration, washing, solid Gossypol recrystallized from chloroform, obtains 17.23g product, productive rate 89%.
3) preparation of final product.
In dry 250ml three-necked bottle, add 9.66g (0.05mol) imidization product and 100ml benzene, after stirring and dissolving, add 0.06ml catalyst made from platonic, after argon gas is fully replaced, 50
oc activates 30min, adds 8.21g (0.05mol) triethoxyl silane, after adding, is warming up to 70
oc, reaction 3h, is cooled to room temperature, revolves desolventizing, obtains weak yellow liquid, and methyl alcohol/chloroform is crossed post (1:9, v/v), obtains 15.19g product, productive rate 85%.
Embodiment 5.
1) preparation of catalyst made from platonic.
Get 1g Platinic chloride and be dissolved in anhydrous isopropyl alcohol, constant volume in 50ml volumetric flask, volumetric molar concentration is 0.0386mol/l.
2) preparation of imidization product.
In dry 500ml three-necked bottle, add 16.41g (0.1mol) norbornylene list acid anhydride and 300ml Glacial acetic acid, after stirring and dissolving, add 5.7g (0.1mol) allyl amine, room temperature reaction 1h, reflux 4h, adds 300ml water after being cooled to room temperature, be heated to boil, be cooled to room temperature, have faint yellow solid to separate out, suction filtration, washing, solid chloroform/acetone recrystallization, obtains 28.28g product, productive rate 90%.
3) preparation of final product.
In dry 250ml three-necked bottle, add 10.16g (0.05mol) imidization product and 100ml benzene, after stirring and dissolving, add 0.06ml catalyst made from platonic, after argon gas is fully replaced, 50
oc activates 30min, adds 8.21g (0.05mol) triethoxyl silane, after adding, is warming up to 70
oc, reaction 3h, is cooled to room temperature, revolves desolventizing, obtains weak yellow liquid, and methyl alcohol/chloroform is crossed post (1:9, v/v), obtains 15.62g product, productive rate 85%.
Embodiment 6.
1) preparation of catalyst made from platonic.
Get 1g Platinic chloride and be dissolved in anhydrous isopropyl alcohol, constant volume in 50ml volumetric flask, volumetric molar concentration is 0.0386mol/l.
2) preparation of imidization product.
In dry 500ml three-necked bottle, add 9.82g (0.1mol) MALEIC ANHYDRIDE and 300ml Glacial acetic acid, after stirring and dissolving, add 5.7g (0.1mol) allyl amine, room temperature reaction 1h, reflux 4h, adds 300ml water after being cooled to room temperature, be heated to boil, be cooled to room temperature, have faint yellow solid to separate out, suction filtration, washing, solid chloroform/acetone recrystallization, obtains 12.06g product, productive rate 88%.
3) preparation of final product.
In dry 250ml three-necked bottle, add 6.86g (0.05mol) imidization product and 100ml benzene, after stirring and dissolving, add 0.06ml catalyst made from platonic, after argon gas is fully replaced, 50
oc activates 30min, adds 8.21g (0.05mol) triethoxyl silane, after adding, is warming up to 70
oc, reaction 3h, is cooled to room temperature, revolves desolventizing, obtains weak yellow liquid, and methyl alcohol/chloroform is crossed post (1:9, v/v), obtains 12.80g product, productive rate 85%.
Embodiment 7.
1) preparation of catalyst made from platonic.
Get 1g Platinic chloride and be dissolved in anhydrous isopropyl alcohol, constant volume in 50ml volumetric flask, volumetric molar concentration is 0.0386mol/l.
2) preparation of imidization product.
In dry 500ml three-necked bottle, add 16.12g (0.05mol) benzophenone tetracarboxylic dianhydride and 300ml Glacial acetic acid, after stirring and dissolving, add 5.7g (0.1mol) allyl amine, room temperature reaction 1h, reflux 4h, adds 300ml water after being cooled to room temperature, be heated to boil, be cooled to room temperature, adularescent solid is separated out, suction filtration, washing, solid chloroform/acetone recrystallization, obtains 28.01g product, productive rate 90%.
3) preparation of final product.
In dry 500ml three-necked bottle, add 2.00 g (0.005mol) imidization product and 300ml benzene, stir and entirely to add 0.12ml catalyst made from platonic after molten, after argon gas is fully replaced, 50
oc activates 30min, adds 1.64g (0.01mol) triethoxyl silane, after adding, is warming up to 70
oc, reaction 3h, is cooled to room temperature, revolves desolventizing, obtains gray solid, and ethyl alcohol recrystallization, obtains 3.06g product, productive rate 84%.
Embodiment 8.
1) preparation of catalyst made from platonic.
Get 1g Platinic chloride and be dissolved in anhydrous isopropyl alcohol, constant volume in 50ml volumetric flask, volumetric molar concentration is 0.0386mol/l.
2) preparation of imidization product.
In dry 500ml three-necked bottle, add 15.51g (0.05mol) phenyl ether tetracarboxylic dianhydride and 300ml Glacial acetic acid, after stirring and dissolving, add 5.7g (0.1mol) allyl amine, room temperature reaction 1h, reflux 4h, adds 300ml water after being cooled to room temperature, be heated to boil, be cooled to room temperature, adularescent solid is separated out, suction filtration, washing, solid chloroform/acetone recrystallization, obtains 17.28g product, productive rate 89%.
3) preparation of final product.
In dry 500ml three-necked bottle, add 1.94 g (0.005mol) imidization product and 300ml benzene, stir and entirely to add 0.12ml catalyst made from platonic after molten, after argon gas is fully replaced, 50
oc activates 30min, adds 1.64g (0.01mol) triethoxyl silane, after adding, is warming up to 70
oc, reaction 3h, is cooled to room temperature, revolves desolventizing, obtains gray solid, and ethyl alcohol recrystallization, obtains 3.07g product, productive rate 86%.
Embodiment 9.
1) preparation of catalyst made from platonic.
Get 1g Platinic chloride and be dissolved in anhydrous isopropyl alcohol, constant volume in 50ml volumetric flask, volumetric molar concentration is 0.0386mol/l.
2) preparation of imidization product.
In dry 500ml three-necked bottle, add 14.81g (0.1mol) phthalic anhydride and 180ml Glacial acetic acid, after stirring and dissolving, add 5.7g (0.1mol) allyl amine, room temperature reaction 1h, reflux 4h, adds 170ml water after being cooled to room temperature, be heated to boil, be cooled to room temperature, have solid to separate out, suction filtration, washing, solid Gossypol recrystallized from chloroform, obtains 16.09g product, productive rate 86%.
3) preparation of final product.
In dry 250ml three-necked bottle, add 9.36 g (0.05mol) imidization product and 100ml benzene, after stirring and dissolving, add 0.06ml catalyst made from platonic, after argon gas is fully replaced, 50
oc activates 30min, adds 6.11g (0.05mol) Trimethoxy silane, after adding, is warming up to 70
oc, reaction 3h, is cooled to room temperature, revolves desolventizing, obtains yellow liquid, and methyl alcohol/chloroform is crossed post (1:9, v/v), obtains 13,14g product, productive rate 85%.
Embodiment 10.
1) preparation of catalyst made from platonic.
Get 1g Platinic chloride and be dissolved in anhydrous isopropyl alcohol, constant volume in 50ml volumetric flask, volumetric molar concentration is 0.0386mol/l.
2) preparation of imidization product.
In dry 500ml three-necked bottle, add 15.42g (0.1mol) HHPA and 180ml Glacial acetic acid, after stirring and dissolving, add 5.7g (0.1mol) allyl amine, room temperature reaction 1h, reflux 4h, adds 170ml water after being cooled to room temperature, be heated to boil, be cooled to room temperature, have solid to separate out, suction filtration, washing, solid Gossypol recrystallized from chloroform, obtains 17.20g product, productive rate 89%.
3) preparation of final product.
In dry 250ml three-necked bottle, add 9.66 g (0.05mol) imidization product and 100ml benzene, after stirring and dissolving, add 0.06ml catalyst made from platonic, after argon gas is fully replaced, 50
oc activates 30min, adds 6.11g (0.05mol) Trimethoxy silane, after adding, is warming up to 70
oc, reaction 3h, is cooled to room temperature, revolves desolventizing, obtains weak yellow liquid, and methyl alcohol/chloroform is crossed post (1:9, v/v), obtains 13.08g product, productive rate 83%.
Embodiment 11.
1) preparation of catalyst made from platonic.
Get 1g Platinic chloride and be dissolved in anhydrous isopropyl alcohol, constant volume in 50ml volumetric flask, volumetric molar concentration is 0.0386mol/l.
2) preparation of imidization product.
In dry 500ml three-necked bottle, add 16.42g (0.1mol) norbornylene list acid anhydride and 180ml Glacial acetic acid, after stirring and dissolving, add 5.7g (0.1mol) allyl amine, room temperature reaction 1h, reflux 4h, adds 170ml water after being cooled to room temperature, be heated to boil, be cooled to room temperature, have solid to separate out, suction filtration, washing, solid Gossypol recrystallized from chloroform, obtains 17.47g product, productive rate 86%.
3) preparation of final product.
In dry 250ml three-necked bottle, add 10.16 g (0.05mol) imidization product and 100ml benzene, after stirring and dissolving, add 0.06ml catalyst made from platonic, after argon gas is fully replaced, 50
oc activates 30min, adds 6.11g (0.05mol) Trimethoxy silane, after adding, is warming up to 70
oc, reaction 3h, is cooled to room temperature, revolves desolventizing, obtains yellow liquid, and methyl alcohol/chloroform is crossed post (1:9, v/v), obtains 13.17g product, productive rate 81%.
Embodiment 12.
1) preparation of catalyst made from platonic.
Get 1g Platinic chloride and be dissolved in anhydrous isopropyl alcohol, constant volume in 50ml volumetric flask, volumetric molar concentration is 0.0386mol/l.
2) preparation of imidization product.
In dry 500ml three-necked bottle, add 9.81 g (0.1mol) MALEIC ANHYDRIDE and 180ml Glacial acetic acid, after stirring and dissolving, add 5.7g (0.1mol) allyl amine, room temperature reaction 1h, reflux 4h, adds 170ml water after being cooled to room temperature, be heated to boil, be cooled to room temperature, adularescent solid is separated out, suction filtration, washing, solid Gossypol recrystallized from chloroform, obtains 11.85g product, productive rate 90%.
3) preparation of final product.
In dry 250ml three-necked bottle, add 6.86 g (0.05mol) imidization product and 100ml benzene, after stirring and dissolving, add 0.06ml catalyst made from platonic, after argon gas is fully replaced, 50
oc activates 30min, adds 6.11g (0.05mol) Trimethoxy silane, after adding, is warming up to 70
oc, reaction 3h, is cooled to room temperature, revolves desolventizing, obtains weak yellow liquid, and methyl alcohol/chloroform is crossed post (1:9, v/v), obtains 11.42g product, productive rate 88%.
Embodiment 13.
1) preparation of catalyst made from platonic.
Get 1g Platinic chloride and be dissolved in anhydrous isopropyl alcohol, constant volume in 50ml volumetric flask, volumetric molar concentration is 0.0386mol/l.
2) preparation of imidization product.
In dry 500ml three-necked bottle, add 10.81g (0.05mol) pyromellitic acid dianhydride and 300ml Glacial acetic acid, after stirring and dissolving, add 5.7g (0.1mol) allyl amine, room temperature reaction 1h, reflux 4h, adds 300ml water after being cooled to room temperature, be heated to boil, be cooled to room temperature, adularescent solid is separated out, suction filtration, washing, solid chloroform/acetone recrystallization, obtains 13.03g product, productive rate 88%.
3) preparation of final product.
In dry 500ml three-necked bottle, add 1.48g (0.005mol) imidization product and 300ml benzene, stir and entirely to add 0.12ml catalyst made from platonic after molten, after argon gas is fully replaced, 50
oc activates 30min, adds 6.11g (0.05mol) Trimethoxy silane, after adding, is warming up to 70
oc, reaction 3h, is cooled to room temperature, revolves desolventizing, obtains gray solid, and ethyl alcohol recrystallization, obtains 2.32g product, productive rate 86%.
Embodiment 14.
1) preparation of catalyst made from platonic.
Get 1g Platinic chloride and be dissolved in anhydrous isopropyl alcohol, constant volume in 50ml volumetric flask, volumetric molar concentration is 0.0386mol/l.
2) preparation of imidization product.
In dry 500ml three-necked bottle, add 14.71g (0.05mol) BPDA and 300ml Glacial acetic acid, after stirring and dissolving, add 5.7g (0.1mol) allyl amine, room temperature reaction 1h, reflux 4h, adds 300ml water after being cooled to room temperature, be heated to boil, be cooled to room temperature, adularescent solid is separated out, suction filtration, washing, solid chloroform/acetone recrystallization, obtains 16.91g product, productive rate 91%.
3) preparation of final product.
In dry 500ml three-necked bottle, add 1.86g (0.005mol) imidization product and 300ml benzene, stir and entirely to add 0.12ml catalyst made from platonic after molten, after argon gas is fully replaced, 50
oc activates 30min, adds 6.11g (0.05mol) Trimethoxy silane, after adding, is warming up to 70
oc, reaction 3h, is cooled to room temperature, revolves desolventizing, obtains gray solid, and ethyl alcohol recrystallization, obtains 2.58g product, productive rate 84%.
Embodiment 15.
1) preparation of catalyst made from platonic.
Get 1g Platinic chloride and be dissolved in anhydrous isopropyl alcohol, constant volume in 50ml volumetric flask, volumetric molar concentration is 0.0386mol/l.
2) preparation of imidization product.
In dry 500ml three-necked bottle, add 16.11g (0.05mol) benzophenone tetracarboxylic dianhydride and 300ml Glacial acetic acid, after stirring and dissolving, add 5.7g (0.1mol) allyl amine, room temperature reaction 1h, reflux 4h, adds 300ml water after being cooled to room temperature, be heated to boil, be cooled to room temperature, adularescent solid is separated out, suction filtration, washing, solid chloroform/acetone recrystallization, obtains 17.81g product, productive rate 89%.
3) preparation of final product.
In dry 500ml three-necked bottle, add 2.00 g (0.005mol) imidization product and 300ml benzene, stir and entirely to add 0.12ml catalyst made from platonic after molten, after argon gas is fully replaced, 50
oc activates 30min, adds 6.11g (0.05mol) Trimethoxy silane, after adding, is warming up to 70
oc, reaction 3h, is cooled to room temperature, revolves desolventizing, obtains gray solid, and ethyl alcohol recrystallization, obtains 2.71g product, productive rate 84%.
Embodiment 16.
1) preparation of catalyst made from platonic.
Get 1g Platinic chloride and be dissolved in anhydrous isopropyl alcohol, constant volume in 50ml volumetric flask, volumetric molar concentration is 0.0386mol/l.
2) preparation of imidization product.
In dry 500ml three-necked bottle, add 15.51g (0.05mol) phenyl ether tetracarboxylic dianhydride and 300ml Glacial acetic acid, after stirring and dissolving, add 5.7g (0.1mol) allyl amine, room temperature reaction 1h, reflux 4h, adds 300ml water after being cooled to room temperature, be heated to boil, be cooled to room temperature, adularescent solid is separated out, suction filtration, washing, solid chloroform/acetone recrystallization, obtains 17.67g product, productive rate 91%.
3) preparation of final product.
In dry 500ml three-necked bottle, add 1.94 g (0.005mol) imidization product and 300ml benzene, stir and entirely to add 0.12ml catalyst made from platonic after molten, after argon gas is fully replaced, 50
oc activates 30min, adds 6.11g (0.05mol) Trimethoxy silane, after adding, is warming up to 70
oc, reaction 3h, is cooled to room temperature, revolves desolventizing, obtains gray solid, and ethyl alcohol recrystallization, obtains 2.62g product, productive rate 83%.
The preparation method who the invention provides a kind of silane coupling agent containing imide ring structural unit, the method technique is simple, and cost is low, and productive rate is high, and product separation is easy.
Claims (1)
1. contain a preparation method for the silane coupling agent of imide ring structural unit, the described single silane coupling agent molecular structural formula containing imide ring structural unit is:
The described single silane coupling agent molecular structural formula containing imide ring structural unit is:
Wherein, R
1for methyl or ethyl; R
2for benzene, hexahydrobenzene, norbornylene or ethene; R
3for benzene, biphenyl, benzophenone or phenyl ether, it is characterized in that as follows:
(1) cyclic anhydride being dissolved in Glacial acetic acid, is that 1:1 or 2:1 add allyl amine by the mol ratio of cyclic anhydride and allyl amine, and stirring and refluxing 2 ~ 36h, adds water, filters, dry, obtains imidization product;
(2) imidization product is dissolved in benzene or toluene, add volumetric molar concentration be 0.01mol/l ~ 0.05mol/l catalyst made from platonic, with imidization product mol ratio be the trialkoxy silane of 1:1 or 2:1, in temperature 50 ~ 90
ounder C condition, react 2 ~ 10h, low boiler cut is removed in underpressure distillation, obtains product;
Described cyclic anhydride is phthalic anhydride, HHPA, norbornylene list acid anhydride, MALEIC ANHYDRIDE, pyromellitic acid dianhydride, BPDA, benzophenone tetracarboxylic dianhydride or phenyl ether tetracarboxylic dianhydride;
Described trialkoxy silane is Trimethoxy silane or triethoxyl silane.
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| CN105131027A (en) * | 2015-07-10 | 2015-12-09 | 南京工业大学 | Synthesis of maleimidotriethoxy silane-series compounds, and preparation method of self-assembled film |
| CN105669738A (en) * | 2016-01-19 | 2016-06-15 | 南昌大学 | Preparation method of modified silane coupling agent |
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| CN110951287A (en) * | 2019-10-28 | 2020-04-03 | 温州裕辉新材料科技有限公司 | High-temperature-resistant ceramic coating and preparation method thereof |
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| CN112028924A (en) * | 2020-08-21 | 2020-12-04 | 齐齐哈尔大学 | N-propylene-N-diethoxymethyl-silicon propyl-pyromellitimide and preparation method thereof |
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| CN112028923A (en) * | 2020-08-21 | 2020-12-04 | 齐齐哈尔大学 | Siloxane 3-phthalimidopropyltriethoxysilane and preparation method thereof |
| CN112028923B (en) * | 2020-08-21 | 2023-08-22 | 齐齐哈尔大学 | Siloxane 3-phthalimide propyl triethoxysilane and preparation method thereof |
| CN112778980A (en) * | 2021-01-26 | 2021-05-11 | 山西万家暖节能科技有限公司 | Energy storage new material for improving heat transfer and mass transfer efficiency |
| CN112812750A (en) * | 2021-01-26 | 2021-05-18 | 山西万家暖节能科技有限公司 | Application of silane coupling agent in new energy storage material and new solar energy heat supply system |
| CN112812750B (en) * | 2021-01-26 | 2021-12-14 | 山西万家暖节能科技有限公司 | Application of silane coupling agent in new energy storage material and new solar energy heat supply system |
| CN112778980B (en) * | 2021-01-26 | 2021-12-14 | 山西万家暖节能科技有限公司 | Energy storage new material for improving heat transfer and mass transfer efficiency |
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