CN103408577A - Amido silane compound based on aromatic diamine and preparation method thereof - Google Patents
Amido silane compound based on aromatic diamine and preparation method thereof Download PDFInfo
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- CN103408577A CN103408577A CN2013103505906A CN201310350590A CN103408577A CN 103408577 A CN103408577 A CN 103408577A CN 2013103505906 A CN2013103505906 A CN 2013103505906A CN 201310350590 A CN201310350590 A CN 201310350590A CN 103408577 A CN103408577 A CN 103408577A
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- 0 C*C(C)c1ccccc1 Chemical compound C*C(C)c1ccccc1 0.000 description 1
- UQAUPOJEVXUTBN-UHFFFAOYSA-N CCNN(C)CC Chemical compound CCNN(C)CC UQAUPOJEVXUTBN-UHFFFAOYSA-N 0.000 description 1
- ZKWIUGDWYAKWOA-UHFFFAOYSA-N C[SiH+](C)NC(CC1)C=CC1Oc(cc1)ccc1N[SiH+](C)C Chemical compound C[SiH+](C)NC(CC1)C=CC1Oc(cc1)ccc1N[SiH+](C)C ZKWIUGDWYAKWOA-UHFFFAOYSA-N 0.000 description 1
- BMPKJPZRCSHNQM-UHFFFAOYSA-N C[Si](C)(C=C)Nc(cc1)ccc1Oc(cc1)ccc1N[Si+](C)(C)C=C Chemical compound C[Si](C)(C=C)Nc(cc1)ccc1Oc(cc1)ccc1N[Si+](C)(C)C=C BMPKJPZRCSHNQM-UHFFFAOYSA-N 0.000 description 1
Abstract
The invention discloses an amido silane compound based on aromatic diamine and a preparation method thereof. The amido silane compound is shown as a formula I; the phenyl ring is ortho-substitution, meta-substitution or para-substitution; R1 is selected from O atom, -CH2-, -C(CH3)2-, -C(CF3)2-, -SO-, -SO2- and -O-Ph-SO2-Ph-O-; and R2, R3 and R4 are selected from H atom, C1-C12 alkyl, C2-C12 alkenyl, C6-C12 aryl and trifluoropropyl. The invention provides the preparation method of the above amido silane compound. The method comprises the following steps: reacting aromatic diamine shown as a formula II with tri-organic radical chlorosilane shown as a formula III to obtain the amido silane compound. In the formula II, R1 is selected from O atom, -CH2-, -C(CH3)2-, -C(CF3)2-, -SO-, -SO2- and -O-Ph-SO2-Ph-O-; and in the formula III R2, R3 and R4 are selected from H atom, C1-C12 alkyl, C2-C12 alkenyl, C6-C12 aryl and trifluoropropyl.
Description
Technical field
The present invention relates to a kind of compound of amino containing silane based on aryl diamine and preparation method thereof.
Background technology
Along with scientific and technological progress, the performance of material is had higher requirement.Organic-inorganic hybrid material is as a kind of type material, not only have the advantages such as the high molecular easy machine-shaping of machine, snappiness is good, cheap, and, with advantages such as high temperature resistant, the high strength of inorganic materials, anti-solvents, show wide application prospect in aerospace, national defence, machinery, environmental protection and the field such as biological.This wherein, siliceous organic-inorganic hybrid material is the focus that people study always, in organic materials, introduce silicon, not only can strengthen or keep the resistance toheat of material, and its good interface performance had and pyroceramic voltinism can be waited, at aspects such as heat-stable material, optical material, coated material, electricity material and catalytic materials, all have great research and using value.
Research for siliceous organic-inorganic hybrid material at present mainly concentrates on monomer or the polymkeric substance that contains Si – O key, also few for the report of the hybrid material that contains Si – N key.The bond energy of Si – N key is higher than Si – O key, and polysilazane generally has higher thermostability, and the organic-inorganic hybrid material that therefore contains Si – N key is a kind of up-and-coming high temperature material.Arylamine reacts with chlorosilane and generates the amino containing silane small molecules, and it can be used as the monomeric compound that preparation contains Si – N key organic-inorganic hybrid material, however some compounds of the amino containing silane based on aryl diamine and preparation method thereof rarely seen report also.
Summary of the invention
The purpose of this invention is to provide a kind of compound of amino containing silane based on aryl diamine and preparation method thereof.
Amino containing silane based on aryl diamine compound provided by the invention, its general structure is suc as formula shown in I:
Formula I
In described formula I, the substituting group on phenyl ring is that ortho position replaces, a position replaces or para-orientation;
R
1For O Yuan, – CH
2–, – C (CH
3)
2–, – C (CF
3)
2–, – SO –, – SO
2– Huo – O – Ph – SO
2– Ph – O –;
R
2, R
3And R
4Identical or different, all be selected from alkenyl, the C6-C12 of alkyl, the C2-C12 of H atom, C1-C12 aryl, contain the aryl of substituent C6-C12 and any one in trifluoro propyl;
Describedly contain substituent C
6 – 12In aryl, substituting group is selected from C
1 – 6Any one in alkyl.
Concrete, in described formula I, R
2, R
3And R
4In at least one substituting group be the alkenyl of C1-C12;
Described R
2, R
3And R
4In, the total number of carbon atoms of alkyl is 1-6; Described alkyl is specially methyl, ethyl or hexyl;
The total number of carbon atoms of alkenyl is 2-6; Described alkenyl is specially vinyl or allyl group;
In the described aryl that contains substituent C6-C12, substituting group is selected from any one in the alkyl of C1-C6;
The described aryl that contains substituent C6-C12 is specially p-methylphenyl or an aminomethyl phenyl.
More specifically, compound shown in described formula I is any one in compound shown in formula IV – formula VIII:
Formula IV
Formula V
Formula VI
Formula VII
Formula VIII
Described R
2, R
3And R
4In at least one substituting group be alkenyl, the R of C1-C12
1The definition formula I compound identical with formula I be specially compound shown in formula V, formula VI or formula VIII.
The invention provides the preparation method of above-mentioned amino containing silane compound, comprise the steps: three organic radical chlorosilanes shown in aryl diamine shown in formula II and formula III are carried out to aminolysis reaction in solvent, obtain compound shown in described formula I;
Formula II formula III
In described formula II, phenyl ring is that ortho position replaces, a position replaces or para-orientation; R
1Definition identical with aforementioned formula I;
In described formula III, R
2, R
3And R
4Definition identical with aforementioned formula I.
In above-mentioned preparation method, shown in described formula II, the molar ratio of three organic radical chlorosilanes shown in aryl diamine and formula III is (1～20): (2～80), preferably (1～13): (2～55) specifically can be 1:2,2:5,4:9,5:14,7:22,9:34,13:55,2-9:5-34,4-5:9-14 or 2-7:5-22.
Described solvent is comprised of component a and components b;
Described component a is acetone, tetrahydrofuran (THF) or acetonitrile;
Described components b is diisopropyl ethyl amine, pyridine or triethylamine.
The volume ratio of described component a and components b is (1～60): (1～40), preferably (1～40): (1～25) specifically can be 20:20,30:20,30:22,30:14 or 40:15.
In described aminolysis reaction step, temperature is 0 ℃～100 ℃, preferably 20 ℃～90 ℃, specifically can be 20 ℃, 40 ℃, 50 ℃ or 70 ℃.
In described aminolysis reaction step, the time is 0.5 hour～72 hours, preferably 0.5 hour～48 hours, specifically can be 0.5 hour, 2 hours, 6 hours, 18 hours, 24 hours or 48 hours.
In above-mentioned preparation method, described reaction is carried out under inert atmosphere, as argon gas or nitrogen.
In addition, the application of compound shown in the formula I that the invention described above provides in the organic inorganic heat thermosetting resin of preparation, also belong to protection scope of the present invention.
The method of the organic inorganic heat thermosetting resin of preparation provided by the invention, comprise the steps: aforementioned R provided by the invention
2, R
3And R
4In at least one substituting group be C
2 – 12Silane compound shown in compound, formula IX shown in the formula I of alkenyl and Ka Si Taide catalyzer (being also the Karstedt catalyzer) mix and carry out addition reaction of silicon with hydrogen, react the complete described organic-inorganic thermosetting resin that obtains;
Formula IX
In described formula IX, R
5Be selected from alkenyl, the C6-C12 of alkyl, the C2-C12 of H atom, C1-C12 aryl, contain the aryl of substituent C6-C12 and any one in trifluoro propyl;
Described containing in substituent C6-C12 aryl, substituting group is selected from any one in C1 – C6 alkyl;
X is O Yuan, – NH –, – CH
2– or singly-bound;
N is the integer of 3 – 1000.
In the described formula IX of aforesaid method, R
5Be selected from any one in the phenyl that H atom, C1-C6 alkyl, C2-C6 alkenyl, phenyl and C1-C3 alkyl replace;
Wherein, described C1-C6 alkyl is specially methyl, ethyl or hexyl;
Described C2-C6 alkenyl is specially vinyl or allyl group;
The phenyl that described C1-C3 alkyl replaces is specially p-methylphenyl or an aminomethyl phenyl;
N is the integer of 3-100, is specially the integer of 3-50, is more specifically the integer of 3-10, is specially 4 most;
The mole dosage ratio that feeds intake of silane compound shown in compound shown in formula I, formula IX and Karstedt catalyzer is (1～200): (1～100): (1 * 10
-6～5000 * 10
-6), be specially 2:1:(40 * 10
-6);
In described addition reaction of silicon with hydrogen step, temperature is 0 ℃～200 ℃, is specially 50 ℃;
Time is 1 hour～72 hours, is specially 12 hours.
Shown in through type II of the present invention, three organic radical chlorosilanes shown in aryl diamine and formula III carry out aminolysis reaction in solvent, have synthesized amino containing silane compound shown in formula I.This simple synthetic method is easily gone, mild condition, and the amino containing silane compound of synthesized has good solubility property, can be used as the synthetic monomeric compound that contains Si – N key organic-inorganic hybrid material, for the preparation of high temperature resistant thermosetting resin, ceramic forerunner etc.
Embodiment
The present invention is further elaborated below in conjunction with specific embodiment, but the present invention is not limited to following examples.Described method is ordinary method if no special instructions.Described starting material all can obtain from open commercial sources if no special instructions.In following embodiment, Karstedt catalyzer used No. CAS is 68478-92-2, and Chinese is platinum (0)-1,3-divinyl-1,1,3,3-tetramethyl disiloxane.
The thermal gravimetric analyzer model of thermal weight loss (TGA) test of doing in the following embodiment of the present invention is: SII6300.
Synthesizing of two (N, N ′ – is trimethyl silicon based) the amido sulfobenzides (shown in IV) of embodiment 1,4,4 ′ –
Under nitrogen atmosphere, add successively 4,4 ' –, bis-amido sulfobenzide (1.24g in bis-mouthfuls of bottles of 100mL, 5mmol), acetone (20mL) and pyridine (20mL), stirring and dissolving, be warming up to 40 ℃, trimethylchlorosilane (1.09g, 10mmol) is dropwise joined in above-mentioned solution, after dropwising, carried out aminolysis reaction 0.5 hour, cool to room temperature, filter, after removal of solvent under reduced pressure, 50 ℃ of vacuum-dryings, obtain faint yellow solid, productive rate 91%, 170 ℃ of fusing point 168 –.
The nuclear-magnetism of this product, ultimate analysis and high resolution mass spectrum characterization result are as follows:
1H–NMR(400MHz,CDCl
3):δ=7.65(d,4H),6.62(d,4H),3.81(s,2H),0.27(s,18H).
13C–NMR(400MHz,acetone-d
6):δ=153.62,131.71,129.65,116.58,–0.20.
29Si–NMR(300MHz,acetone-d
6):δ=2.80.Anal.Calcd.for?C
18H
28N
2O
2SSi
2:C,55.05;H,7.20;N,7.14%.Found:C,54.75;H,6.86;N,7.08%.HRMS(EI):Calcd.:392.1410;Found:392.1414.
As can be known by above-mentioned characterization data, the structural formula of this product is suc as formula shown in IV:
Formula IV
Synthesizing of two (N, N ′ – dimethyl vinyl is silica-based) the amido sulfobenzides (shown in V) of embodiment 2,4,4 ′ – and organic-inorganic thermosetting resin
Under nitrogen atmosphere, add successively 4,4 ' –, bis-amido sulfobenzide (1.74g in bis-mouthfuls of bottles of 100mL, 7mmol), tetrahydrofuran (THF) (30mL) and diisopropyl ethyl amine (20mL), stirring and dissolving, under 20 ℃, by dimethyl vinyl chlorosilane (2.11g, 17.5mmol) dropwise join in above-mentioned solution, dropwise rear aminolysis reaction 2 hours, filter, 50 ℃ of vacuum-dryings after removal of solvent under reduced pressure, obtain faint yellow solid, productive rate 92%, 128 ℃ of fusing point 127 –.
The nuclear-magnetism of this product, ultimate analysis and high resolution mass spectrum characterization result are as follows:
1H–NMR(400MHz,CDCl
3):δ=7.63(d,4H),6.65(d,4H),6.18(dd,2H),6.08(dd,2H),5.86(dd,2H),3.83(s,2H),0.32(s,12H).
13C–NMR(400MHz,acetone-d
6):δ=153.36,138.09,134.28,131.92,129.52,116.82,–1.96.
29Si–NMR(300MHz,acetone-d
6):δ=–7.68.Anal.Calcd.for?C
20H
28N
2O
2SSi
2:C,57.65;H,6.79;N,6.72%.Found:C,57.43;H,6.89;N,6.40%.HRMS(EI):Calcd.:416.1410;Found:416.1415.
As can be known by above-mentioned characterization data, the structural formula of this product is suc as formula shown in V:
Formula V
By the amino containing silane compound (2.08g, 5mmol) shown in formula V and 1,3,5 of ownership formula IX, 7-tetramethyl-ring tetrasiloxane (D
4H, 0.60g, 2.5mmol, n=4) mix, add Karstedt catalyzer (100 * 10
-6Mmol), 50 ℃ are carried out addition reaction of silicon with hydrogen 12h, can obtain the organic inorganic hybridization thermosetting resin.
Resin is carried out to the TGA test.Test condition is as follows: high pure nitrogen or air atmosphere, temperature rise rate are 10 ℃/min.
Test result is: under nitrogen, the temperature of thermal weight loss 10% is 428 ℃, under 800 ℃ residual heavy be 62.1%; Under air, the temperature of thermal weight loss 10% is 404 ℃, under 800 ℃ residual heavy be 54.5%.
Visible, gained organic inorganic hybridization thermosetting resin has higher heat decomposition temperature and high temperature is residual heavy, shows good thermostability and thermo-oxidative stability.
Synthesizing of two (N, N ′ – dimethyl vinyl is silica-based) the amido phenyl ether (shown in VI) of embodiment 3,4,4 ′ – and organic-inorganic thermosetting resin
Under nitrogen atmosphere, add successively 4,4 ′ – diaminodiphenyl ether (2.00g in bis-mouthfuls of bottles of 250mL, 10mmol), acetonitrile (30mL) and triethylamine (22mL), stirring and dissolving, be warming up to 50 ℃, by dimethyl vinyl chlorosilane (2.71g, 22.5mmol) dropwise join in above-mentioned solution, dropwise rear aminolysis reaction 18 hours, filter 50 ℃ of vacuum-dryings after removal of solvent under reduced pressure, obtain tawny liquid, productive rate 96%.
The nuclear-magnetism of this product and high resolution mass spectrum characterization result are as follows:
1H–NMR(400MHz,CDCl
3):δ=6.77(d,4H),6.60(d,4H),6.22(dd,2H),6.06(dd,2H),5.86(dd,2H),3.33(s,2H),0.31(s,12H).
13C–NMR(400MHz,DMSO-d
6):δ=148.85,143.18,138.55,132.93,118.91,116.63,–1.86.
29Si–NMR(300MHz,acetone-d
6):δ=–7.58.HRMS(EI):Calcd.for?C
20H
28N
2OSi
2:368.1740;Found:368.1747.
As can be known by above-mentioned characterization data, the structural formula of this product is suc as formula shown in VI:
Formula VI
By the amino containing silane compound (1.84g, 5mmol) shown in formula VI and 1,3,5 of ownership formula IX, 7-tetramethyl-ring tetrasiloxane (D
4H, 0.60g, 2.5mmol, n=4) mix, add Karstedt catalyzer (100 * 10
-6Mmol), 50 ℃ are carried out addition reaction of silicon with hydrogen 12h, obtain the organic inorganic hybridization thermosetting resin.
Resin is carried out to the TGA test.Test condition is as follows: high pure nitrogen or air atmosphere, temperature rise rate are 10 ℃/min.
Test result is: under nitrogen, the temperature of thermal weight loss 10% is 563 ℃, under 800 ℃ residual heavy be 80.3%; Under air, the temperature of thermal weight loss 10% is 528 ℃, under 800 ℃ residual heavy be 60.1%.
Visible, gained organic inorganic hybridization thermosetting resin have very high heat decomposition temperature and higher high temperature residual heavy, show good thermostability and thermo-oxidative stability.
Synthesizing of two (N, N ' – dimethyl is silica-based) the amido phenyl ether (shown in VII) of embodiment 4,4,4 ' –
Under nitrogen atmosphere, add successively 4,4 ′ – diaminodiphenyl ether (0.90g in bis-mouthfuls of bottles of 100mL, 4.5mmol), tetrahydrofuran (THF) (30mL) and triethylamine (14mL), stirring and dissolving, under 20 ℃, by dimethylchlorosilane (1.61g, 17mmol) dropwise join in above-mentioned solution, dropwise rear aminolysis reaction 48 hours, filter 50 ℃ of vacuum-dryings after removal of solvent under reduced pressure, obtain weak yellow liquid, productive rate 95%.
The nuclear-magnetism of this product and high resolution mass spectrum characterization result are as follows:
1H–NMR(400MHz,CDCl
3):δ=6.81(d,4H),6.62(d,4H),4.75–4.70(m,2H),3.30(s,2H),0.30(d,12H).
13C–NMR(400MHz,acetone-d
6):δ=150.54,143.83,119.97,117.17,–2.08.
29Si–NMR(300MHz,acetone-d
6):δ=–14.14.HRMS(EI):Calcd.for?C
16H
24N
2OSi
2:316.1427;Found:316.1432.
As can be known by above-mentioned characterization data, the structural formula of this product is suc as formula shown in VII:
Formula VII
Synthesizing of two [3 – (N – dimethyl vinyl the is silica-based) amido phenoxy group] sulfobenzides (shown in VIII) of embodiment 5,4,4 ′ – and organic-inorganic thermosetting resin
Under nitrogen atmosphere, add successively two (the 3 – amido phenoxy group) sulfobenzide (5.62g of 4,4 ′ – in bis-mouthfuls of bottles of 250mL, 13mmol), acetonitrile (40mL) and pyridine (15mL), stirring and dissolving, be warming up to 70 ℃, by dimethyl vinyl chlorosilane (6.64g, 55mmol) dropwise join in above-mentioned solution, dropwise rear aminolysis reaction 24 hours, filter, 50 ℃ of vacuum-dryings after removal of solvent under reduced pressure, obtain yellow solid, productive rate 93%, 47 ℃ of fusing point 44 –.
The nuclear-magnetism of this product and high resolution mass spectrum characterization result are as follows:
1H–NMR(400MHz,CDCl
3):δ7.85(d,4H),7.10(t,2H),7.02(d,4H),6.50(d,2H),6.36(d,2H),6.32(s,2H),6.17(dd,2H),6.03(dd,2H),5.81(dd,2H),3.56(s,2H),0.29(s,12H).
13C–NMR(400MHz,acetone-d
6):δ=162.66,156.81,150.83,138.61,136.64,133.85,131.13,130.47,118.66,113.76,109.27,108.54,–1.86.
29Si–NMR(300MHz,acetone-d
6):δ=–7.64.HRMS(EI):Calcd.for?C
32H
36N
2O
4SSi
2:600.1934;Found:600.1941.
As can be known by above-mentioned characterization data, the structural formula of this product is suc as formula shown in VIII:
Formula VIII
By the amino containing silane compound (3.00g, 5mmol) shown in formula VIII and 1,3,5 of ownership formula IX, 7-tetramethyl-ring tetrasiloxane (D
4H, 0.60g, 2.5mmol, n=4) mix Karstedt catalyzer (100 * 10
-6Mmol), 50 ℃ are carried out addition reaction of silicon with hydrogen 12h, obtain the organic inorganic hybridization thermosetting resin.
Resin is carried out to the TGA test.Test condition is as follows: high pure nitrogen or air atmosphere, temperature rise rate are 10 ℃/min.
Test result is: under nitrogen, the temperature of thermal weight loss 10% is 474 ℃, under 800 ℃ residual heavy be 58.6%; Under air, the temperature of thermal weight loss 10% is 464 ℃, under 800 ℃ residual heavy be 50.1%.
Visible, gained organic inorganic hybridization thermosetting resin have very high heat decomposition temperature and higher high temperature residual heavy, show good thermostability and thermo-oxidative stability.
Claims (10)
1. compound shown in formula I,
Formula I
In described formula I, the substituting group on phenyl ring is that ortho position replaces, a position replaces or para-orientation;
R
1For O Yuan, – CH
2–, – C (CH
3)
2–, – C (CF
3)
2–, – SO –, – SO
2– Huo – O – Ph – SO
2– Ph – O –;
R
2, R
3And R
4Identical or different, all be selected from alkenyl, the C6-C12 of alkyl, the C2-C12 of H atom, C1-C12 aryl, contain the aryl of substituent C6-C12 and any one in trifluoro propyl;
In the described aryl that contains substituent C6-C12, substituting group is selected from any one in the alkyl of C1-C6.
2. compound according to claim 1 is characterized in that: in described formula I, and R
2, R
3And R
4In at least one substituting group be the alkenyl of C1-C12;
Described R
2, R
3And R
4In, the total number of carbon atoms of alkyl is 1-6; Described alkyl is specially methyl, ethyl or hexyl;
The total number of carbon atoms of alkenyl is 2-6; Described alkenyl is specially vinyl or allyl group;
In the described aryl that contains substituent C6-C12, substituting group is selected from any one in the alkyl of C1-C6;
The described aryl that contains substituent C6-C12 is specially p-methylphenyl or an aminomethyl phenyl.
3. compound according to claim 1 and 2 is characterized in that: compound shown in described formula I is formula IV to any one in compound shown in formula VIII:
Formula IV
Formula V
Formula VI
Formula VII
Formula VIII.
4. a method for preparing compound shown in the arbitrary described formula I of claim 1 – 3, comprise the steps:
Three organic radical chlorosilanes shown in aryl diamine shown in formula II and formula III are carried out to aminolysis reaction in solvent, obtain compound shown in described formula I;
Formula II formula III
In described formula II, phenyl ring is that ortho position replaces, a position replaces or para-orientation; R
1Definition identical with claim 1;
In described formula III, R
2, R
3And R
4Definition identical with claim 1.
5. method according to claim 4 is characterized in that: the molar ratio of three organic radical chlorosilanes shown in aryl diamine and formula III shown in described formula II is (1～20): (2～80).
6. according to the described method of claim 4 or 5, it is characterized in that: described solvent is comprised of component a and components b;
Described component a is acetone, tetrahydrofuran (THF) or acetonitrile;
Described components b is diisopropyl ethyl amine, pyridine or triethylamine;
The volume ratio of described component a and components b is (1～60): (1～40);
In described aminolysis reaction step, temperature is 0 ℃～100 ℃;
Time is 0.5 hour～72 hours;
Described aminolysis reaction carries out under inert atmosphere;
Described inert atmosphere is specially nitrogen atmosphere or argon gas atmosphere.
7. the application of compound shown in the arbitrary described formula I of claim 1 – 3 in the organic inorganic heat thermosetting resin of preparation.
8. a method for preparing organic inorganic heat thermosetting resin, comprise the steps: arbitrary described R by claim 1 – 3
2, R
3And R
4In at least one substituting group be C
2 – 12Silane compound shown in compound, formula IX shown in the formula I of alkenyl and Ka Si Taide catalyzer mix and carry out addition reaction of silicon with hydrogen, react the complete described organic-inorganic thermosetting resin that obtains;
Formula IX
In described formula IX, R
5Be selected from alkenyl, the C6-C12 of alkyl, the C2-C12 of H atom, C1-C12 aryl, contain the aryl of substituent C6-C12 and any one in trifluoro propyl;
Describedly contain substituent C
6 – 12In aryl, substituting group is selected from any one in C1 – C6 alkyl;
X is O Yuan, – NH –, – CH
2– or singly-bound;
N is the integer of 3 – 1000.
9. method according to claim 8 is characterized in that: in described formula IX, and R
5Be selected from any one in the phenyl that H atom, C1-C6 alkyl, C2-C6 alkenyl, phenyl and C1-C3 alkyl replace;
Wherein, described C1-C6 alkyl is specially methyl, ethyl or hexyl;
Described C2-C6 alkenyl is specially vinyl or allyl group;
The phenyl that described C1-C3 alkyl replaces is specially p-methylphenyl or an aminomethyl phenyl;
N is the integer of 3-100, is specially the integer of 3-50, is more specifically the integer of 3-10, is specially 4 most;
The mole dosage ratio that feeds intake of silane compound shown in compound, formula IX shown in described formula I and Ka Si Taide catalyzer is (1～200): (1～100): (1 * 10
-6～5000 * 10
-6), be specially 2:1:(40 * 10
-6);
In described addition reaction of silicon with hydrogen step, temperature is 0 ℃～200 ℃, is specially 50 ℃;
Time is 1 hour～72 hours, is specially 12 hours.
10. the organic-inorganic thermosetting resin for preparing of the described method of claim 8 or 9.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107955157A (en) * | 2016-10-14 | 2018-04-24 | 徐州工程学院 | A kind of cross-linking siliceous main chain aryl oxide lonitrile copolymer and preparation method thereof |
| CN107955159A (en) * | 2016-10-14 | 2018-04-24 | 徐州工程学院 | A kind of siliceous main chain aryl oxide lonitrile copolymer and preparation method thereof |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107955157A (en) * | 2016-10-14 | 2018-04-24 | 徐州工程学院 | A kind of cross-linking siliceous main chain aryl oxide lonitrile copolymer and preparation method thereof |
| CN107955159A (en) * | 2016-10-14 | 2018-04-24 | 徐州工程学院 | A kind of siliceous main chain aryl oxide lonitrile copolymer and preparation method thereof |
| CN107955157B (en) * | 2016-10-14 | 2020-11-20 | 徐州工程学院 | Crosslinkable silicon-containing main chain arylethernitrile copolymer and preparation method thereof |
| CN107955159B (en) * | 2016-10-14 | 2020-11-20 | 徐州工程学院 | Silicon-containing main chain arylethernitrile copolymer and preparation method thereof |
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| CN103408577B (en) | 2016-02-24 |
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