CN102199169A - Novel preparation method of organic amido silane - Google Patents
Novel preparation method of organic amido silane Download PDFInfo
- Publication number
- CN102199169A CN102199169A CN2011100896275A CN201110089627A CN102199169A CN 102199169 A CN102199169 A CN 102199169A CN 2011100896275 A CN2011100896275 A CN 2011100896275A CN 201110089627 A CN201110089627 A CN 201110089627A CN 102199169 A CN102199169 A CN 102199169A
- Authority
- CN
- China
- Prior art keywords
- organic
- base silane
- amide base
- new preparation
- organic amide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 229910000077 silane Inorganic materials 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- -1 amido silane Chemical compound 0.000 title abstract description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 30
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 19
- 150000003857 carboxamides Chemical class 0.000 claims abstract description 19
- 239000002994 raw material Substances 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 11
- 150000001408 amides Chemical class 0.000 claims abstract description 11
- 239000011230 binding agent Substances 0.000 claims abstract description 10
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000001257 hydrogen Substances 0.000 claims abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 239000012046 mixed solvent Substances 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 239000000706 filtrate Substances 0.000 claims description 3
- 238000004886 process control Methods 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 125000000962 organic group Chemical group 0.000 abstract 2
- 238000011112 process operation Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- NCCHARWOCKOHIH-UHFFFAOYSA-N n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC=C1 NCCHARWOCKOHIH-UHFFFAOYSA-N 0.000 description 3
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 3
- NRRCUGMIRCVFHG-UHFFFAOYSA-N C[SiH2]OCC.CNC(C1=CC=CC=C1)=O Chemical compound C[SiH2]OCC.CNC(C1=CC=CC=C1)=O NRRCUGMIRCVFHG-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- MROCJMGDEKINLD-UHFFFAOYSA-N dichlorosilane Chemical compound Cl[SiH2]Cl MROCJMGDEKINLD-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical group [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003368 amide group Chemical class 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- AXTPGQHJFRSSQJ-UHFFFAOYSA-N dichloro-ethoxy-methylsilane Chemical compound CCO[Si](C)(Cl)Cl AXTPGQHJFRSSQJ-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
Abstract
The invention relates to a novel preparation method of organic amido silane, which has the advantages of simple process, mild reaction conditions and high reaction yield. The general formula of the prepared organic amide silane is as follows:
Description
Technical field
The invention belongs to organosilyl preparation field, particularly a kind of new preparation method of organic amide base silane.
Background technology
Amino silicane coupling agent is proposed in nineteen fifty-five first by U.S. UCC company, then derives a series of modified amido silane coupling agents successively.Amino silicane coupling agent has catalytic, can make catalyzer in the polymerization of phenolic aldehyde, urea aldehyde, melamino-formaldehyde, also can be used as the solidifying agent of epoxy and urethane resin, belongs to universal.Aspect tackifier, textile auxiliary agent and the biochemistry of its surface treatment, Inorganic Fillers Filled plastics, sealing agent, tackiness agent and coating, the environmental protection important use is arranged all at glass fibre.
The method of the synthetic organic amide base silane of report mainly is that organic halosilanes and acid amides react by taking off HX at present, is example with synthetic two (N-methyl-benzamide) methyl ethoxy silane, and the reaction structure formula is expressed as follows:
For impelling reaction to carry out, often add basic cpd in the reaction to the right.Bibliographical information mainly contains 2 kinds of modes at present, a kind of employing alkali metallic sodium, and another kind then adopts sodium methylate.
United States Patent (USP) (US 3776933) elder generation added toluene and sodium Metal 99.5 in the reaction flask in 1973, and reflux is broken into sodium sand with sodium, adds AcNHMe again, and reaction generates AcNMeNa and reacts the product that generation needs with dichlorosilane again.The product of producing more is applicable to commercial applications, but reaction yield is lower, and must remove unreacted metal sodium fully before the halosilanes with the back reacts, in case do not remove fully, will bring serious safety problem.
1986 United States Patent (USP) (US 4739088) make earlier the AcNHMe-toluene solution in reaction flask with the reaction of the methanol solution of MeONa, steam except that behind the MeOH and obtain AcNMeNa, and then react with dichlorosilane, the product yield height that obtains, but the operation process is comparatively loaded down with trivial details, and wherein reaction process needs to remove methyl alcohol midway, in case the not enough methyl alcohol of distillation time does not steam fully, productive rate will significantly descend even cause the failure of entire reaction, and this has increased the cost of whole production technology virtually.
Summary of the invention
The invention solves the problems and shortcomings that exist in the above-mentioned technology, a kind of new preparation method of organic amide base silane is provided, adopt triethylamine as acid binding agent.This method technological operation is simple, safety, and product yield and purity height are applicable to that laboratory and factory produce in batches.
The present invention is achieved by the following technical solutions:
The present invention is a kind of new preparation method of organic amide base silane; comprise the steps: with the acid amides to be raw material; be dissolved in the organic solvent inert; it is acid binding agent that the back adds triethylamine; slowly drip halosilanes then; drip process control temp at 5 ℃～20 ℃; be controlled at this temperature stirring reaction 30 minutes～3 hours; back elevated temperature to 80 ℃～110 ℃ reaction 2～8 hours; after heating finishes, cooling reaction mixture to 10～20 ℃, solids removed by filtration salt under the nitrogen protection; filtrate is heated to 65～70 ℃ except that desolvating under 10～20mmHg, promptly obtain organic amide base base silane.
Described reaction system adopts exsiccant nitrogen to protect, and makes whole process be reflected under the anhydrous condition and carries out.
Described raw material acid amides needs the dry residual moisture content of possibility of removing.
Described inert organic solvents is selected from toluene, benzene, one or more mixed solvents of dimethylbenzene, and must all will remove moisture content residual in the solvent through super-dry.
Described acid binding agent triethylamine need be removed residual moisture content through super-dry.
The organic halosilanes of described raw material need be purified through distillation, collects cut at the boiling point place.
Mol ratio between described raw material acid amides and the inert solvent is 1: 4～20.
The mol ratio of described raw material acid amides and organic halosilanes is 1: 0.7～2.5.
The mol ratio of described organic halosilanes and acid binding agent triethylamine is 1: 1～5.
Beneficial effect of the present invention:
(1) technology is simple, and is easy to operate
(2) reaction safety, no potentially dangerous
(3) product yield and purity height
(4) be applicable to that laboratory and factory produce in batches
Embodiment
Below in conjunction with specific embodiment, further set forth the present invention.Should understand, these embodiment only are used for the present invention and are not used in limiting the scope of the invention, should understand in addition, after the content of having read the present invention's instruction, those skilled in the art can make various changes or modifications the present invention, and these equivalent form of values fall within the application's appended claims institute restricted portion equally.
Embodiment 1
In the reaction flask of exsiccant nitrogen protection, add dried toluene 25ml (0.24mol); after add exsiccant N-methyl-benzamide 6.45g (0.048mol) again; after treating to dissolve fully; reduce the temperature to back below 10 ℃ and drip 15ml (0.1mol) exsiccant triethylamine; after slowly drip methyl ethoxy dichlorosilane 4.5ml (0.03mol) through constant pressure funnel; drip process control temp below 20 ℃; be added dropwise to complete afterreaction liquid stirring reaction 30 minutes; be warmed up to 100 ℃ of stirring reactions 4 hours then; cool to below 20 ℃; after-filtration is gone out hydrochloride precipitation; filtrate is at 20mmHg; 70 ℃ of following underpressure distillation steam up to no longer including cut, and the surplus materials cold filtration obtains flaxen oily liquids two (N-methyl-benzamide) methyl ethoxy silane 8.44 grams (content 80%).
1H-NMR analyzes, interior mark (TMS), solvent is deuterated dimethyl sulfoxide (DMSO-D6), chemical shift is represented with δ, unit is ppm, and being respectively a=0.3～0.4 (m), b=1.11～1.19 (m), c=3.79～3.87 (m), d=2.75～2.81 (m), H-Ar is 7.27～7.86.
Embodiment 2
Change the solvent in the example 1 mixed solvent of the normal heptane of the toluene of 15mL and 15mL into, other step is fully identical with example 1.Because the raw material N-methyl-benzamide can not be dissolved in this mixed solvent, thus in the reaction system not the raw material N-methyl-benzamide of complete reaction can remove by this solvent, reach the purpose of refined product.Obtain flaxen oily liquids at last, content 85%, productive rate reaches 74%.
Embodiment 3
Change the acid binding agent triethylamine in the example 1 into pyridine, other step is fully identical with example 1, do not see have the product peak to occur by gas chromatographic detection in the reaction process, the alkalescence that pyridine is described also is not enough to the HCl that produces in the absorption reaction system, is not suitable for doing the acid binding agent of this reaction.
Embodiment 4
Prisoner among the embodiment 1 acid agent is changed into tributylamine, other step is fully identical with example 1, do not see the appearance that the product peak is arranged by gas chromatographic detection in the reaction process, reach a conclusion, though, the alkalescence of Tributylamine is enough, but may be because therefore butyl sterically hindered bigger hinder the absorption of Tributylamine to HCl.
Claims (10)
1. the new preparation method of an organic amide base silane; concrete steps are as follows: be raw material with the acid amides; be dissolved in the organic solvent inert; it is acid binding agent that the back adds triethylamine; slowly drip organic halosilanes then; drip process control temp at 5 ℃～20 ℃; be controlled at this temperature stirring reaction 0.5～3 hour; back elevated temperature to 80 ℃～110 ℃ reaction 2～8 hours; after heating finishes, cooling reaction mixture to 10～20 ℃, solids removed by filtration salt under the nitrogen protection; filtrate is heated to 65～70 ℃ except that desolvating under 10～20mmHg, promptly obtain needed organic amide base silane.
2. the new preparation method of a kind of organic amide base silane according to claim 1 is characterized in that: the general formula of the organic amide base silane of described preparation is:
The general formula of described raw material acid amides is:
The general formula of described organic halosilanes is:
R
1R
2OSiX
2
R1 in the described general formula of this patent, R2, R3 are hydrogen and identical or different monovalence alkyl, and R4 is monovalence alkyl or phenyl.
3. the new preparation method of a kind of organic amide base silane according to claim 1; it is characterized in that: omnidistance reaction needed is carried out under anhydrous condition; reaction system exist the water vapour of trace just can make the organic halosilanes hydrolysis of reactant because need only in the reaction system, so should adopt exsiccant nitrogen to protect.
4. the new preparation method of a kind of organic amide base silane according to claim 1 is characterized in that: described raw material acid amides needs recrystallization, dry moisture content that may be residual.
5. the new preparation method of a kind of organic amide base silane according to claim 1, it is characterized in that: described inert organic solvents is selected from one or more mixed solvents of toluene, benzene, dimethylbenzene, and must all will remove moisture content residual in the solvent through super-dry.
6. the new preparation method of a kind of organic amide base silane according to claim 1 is characterized in that: described acid binding agent triethylamine need be removed residual moisture content through super-dry.
7. the new preparation method of a kind of organic amide base silane according to claim 1 is characterized in that: the organic halosilanes of described raw material need be purified through distillation, collects cut at the boiling point place.
8. the new preparation method of a kind of organic amide base silane according to claim 1 is characterized in that: the mol ratio between described raw material acid amides and the inert solvent is 1: 4～20.
9. the new preparation method of a kind of organic amide base silane according to claim 1 is characterized in that: described acid binding agent triethylamine and mol ratio organic halosilanes are 1: 0.5～1.3.
10. the new preparation method of a kind of organic amide base silane according to claim 1 is characterized in that: the mol ratio of described raw material acid amides and organic halosilanes is 1: 0.7～1.5.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011100896275A CN102199169A (en) | 2011-04-11 | 2011-04-11 | Novel preparation method of organic amido silane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011100896275A CN102199169A (en) | 2011-04-11 | 2011-04-11 | Novel preparation method of organic amido silane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102199169A true CN102199169A (en) | 2011-09-28 |
Family
ID=44660186
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2011100896275A Pending CN102199169A (en) | 2011-04-11 | 2011-04-11 | Novel preparation method of organic amido silane |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102199169A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111285896A (en) * | 2020-01-14 | 2020-06-16 | 浙江衢州硅宝化工有限公司 | Preparation method of bis (N-methylbenzamide) ethoxymethylsilane |
| CN112375096A (en) * | 2020-11-24 | 2021-02-19 | 江西晨光新材料股份有限公司 | Synthesis method of amidosilane |
| CN113754687A (en) * | 2021-09-23 | 2021-12-07 | 浙江衢州硅宝化工有限公司 | Preparation method of bis (N-methylbenzamide) ethoxymethylsilane |
| CN114573628A (en) * | 2022-04-13 | 2022-06-03 | 洛阳中硅高科技有限公司 | System and method for preparing amino silane |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2876234A (en) * | 1955-06-01 | 1959-03-03 | Rohm & Haas | Organic silicon compounds and methods for making them |
| US2876209A (en) * | 1955-06-01 | 1959-03-03 | Rohm & Haas | Organic silicon compounds and methods for making them |
| US3776933A (en) * | 1972-09-29 | 1973-12-04 | Dow Corning | Method of preparing amidosilanes |
| US4739088A (en) * | 1985-02-12 | 1988-04-19 | Bayer Aktiengesellschaft | Process for the preparation of amidosilanes |
-
2011
- 2011-04-11 CN CN2011100896275A patent/CN102199169A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2876234A (en) * | 1955-06-01 | 1959-03-03 | Rohm & Haas | Organic silicon compounds and methods for making them |
| US2876209A (en) * | 1955-06-01 | 1959-03-03 | Rohm & Haas | Organic silicon compounds and methods for making them |
| US3776933A (en) * | 1972-09-29 | 1973-12-04 | Dow Corning | Method of preparing amidosilanes |
| US4739088A (en) * | 1985-02-12 | 1988-04-19 | Bayer Aktiengesellschaft | Process for the preparation of amidosilanes |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111285896A (en) * | 2020-01-14 | 2020-06-16 | 浙江衢州硅宝化工有限公司 | Preparation method of bis (N-methylbenzamide) ethoxymethylsilane |
| CN111285896B (en) * | 2020-01-14 | 2023-06-23 | 浙江衢州硅宝化工有限公司 | Preparation method of bis (N-methylbenzamide) ethoxymethylsilane |
| CN112375096A (en) * | 2020-11-24 | 2021-02-19 | 江西晨光新材料股份有限公司 | Synthesis method of amidosilane |
| CN112375096B (en) * | 2020-11-24 | 2023-05-02 | 江西晨光新材料股份有限公司 | Synthesis method of amido silane |
| CN113754687A (en) * | 2021-09-23 | 2021-12-07 | 浙江衢州硅宝化工有限公司 | Preparation method of bis (N-methylbenzamide) ethoxymethylsilane |
| CN113754687B (en) * | 2021-09-23 | 2024-03-01 | 浙江衢州硅宝化工有限公司 | Preparation method of bis (N-methylbenzamide) ethoxymethylsilane |
| CN114573628A (en) * | 2022-04-13 | 2022-06-03 | 洛阳中硅高科技有限公司 | System and method for preparing amino silane |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101659748B (en) | Hyper-branched silicone resin containing active functional group and preparation method thereof | |
| CN104059228A (en) | Bisphenol A type poly sulfuric acid (ammonia) ester compound and synthetic method thereof | |
| CN101268089B (en) | Method for producing ketimine structure-containing alkoxysilane | |
| CN111793210B (en) | Preparation method of RTV (room temperature vulcanized) silicone rubber tackifier | |
| CN102199169A (en) | Novel preparation method of organic amido silane | |
| CN103145994A (en) | Trapezoidal polysiloxane and preparation method thereof | |
| CN1935783B (en) | A synthetic method of 3,3'-dimethyl-4, 4'-biphenyl diisocyanate | |
| CN102532186B (en) | Method for preparing hydroxyimino organosilicon compounds | |
| CN101857674B (en) | Method for synthesizing high-temperature resistant organic silicon resin | |
| CN104262382A (en) | Preparation method of ureido silane coupling agent | |
| CN101880392A (en) | Method for preparing hydroxyl silicone oil by taking sodium acetate as acylating agent | |
| CN103804403A (en) | Method for preparing 2-hydroxybenzeneboronic acid | |
| CN106349277B (en) | A method of preparing alkoxy end-capped poly- methyl trifluoro propyl siloxane oligomer | |
| CN103342715B (en) | Preparation method of aminopropyl-containing organic oximido-silicon compound | |
| CN100465179C (en) | Prepn of isocyanate-containing alkyl silane or alkyl siloxane | |
| CN105315232A (en) | Method for preparing acryloyl morpholine | |
| CN100386335C (en) | Preparation method of substituted diaryl phosphate | |
| CN103601890B (en) | A kind of synthetic method of pectination polysiloxane flax soft finishing agent | |
| CN110204459A (en) | A kind of aromatic series diether dioctyl phthalate and preparation method thereof | |
| CN102604101B (en) | Synthesis method for phenyl organosilicon copolymer with uniformly distributed phenyl units | |
| CN102504269A (en) | Preparation method of polyborosilazane precursor | |
| CN100357299C (en) | Methylphenyldichlor disilane synthesis method | |
| CN107445856B (en) | Synthesis process of N-isopropyl acrylamide | |
| CN101585850A (en) | Aromatic cyanate ester monomer containing silicon and preparation method thereof | |
| CN105399763A (en) | Synthetic method for glycidyl ether oxysilane |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20110928 |
|
| WD01 | Invention patent application deemed withdrawn after publication |