CN109438502A - A kind of α isocyanatomethyl silane and preparation method thereof - Google Patents
A kind of α isocyanatomethyl silane and preparation method thereof Download PDFInfo
- Publication number
- CN109438502A CN109438502A CN201811186576.6A CN201811186576A CN109438502A CN 109438502 A CN109438502 A CN 109438502A CN 201811186576 A CN201811186576 A CN 201811186576A CN 109438502 A CN109438502 A CN 109438502A
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- CN
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- Prior art keywords
- isocyanatomethyl
- silane
- preparation
- cyanate
- silane according
- 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.)
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- MBOOMFWIUMKSNA-UHFFFAOYSA-N isocyanatomethylsilane Chemical compound [SiH3]CN=C=O MBOOMFWIUMKSNA-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- 150000004756 silanes Chemical class 0.000 claims abstract description 10
- 239000007822 coupling agent Substances 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical group [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 21
- 229910052759 nickel Inorganic materials 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
- ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 claims description 6
- 238000005292 vacuum distillation Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- DXRFZHILMCWCNG-UHFFFAOYSA-N N,N-dimethyl-1,8-naphthyridin-2-amine Chemical compound C1=CC=NC2=NC(N(C)C)=CC=C21 DXRFZHILMCWCNG-UHFFFAOYSA-N 0.000 claims description 3
- QYTOONVFPBUIJG-UHFFFAOYSA-N azane;cyanic acid Chemical compound [NH4+].[O-]C#N QYTOONVFPBUIJG-UHFFFAOYSA-N 0.000 claims description 3
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 claims description 3
- 150000003222 pyridines Chemical class 0.000 claims description 3
- 150000004040 pyrrolidinones Chemical class 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 1
- CMEWLCATCRTSGF-UHFFFAOYSA-N N,N-dimethyl-4-nitrosoaniline Chemical compound CN(C)C1=CC=C(N=O)C=C1 CMEWLCATCRTSGF-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- UIUXUFNYAYAMOE-UHFFFAOYSA-N methylsilane Chemical compound [SiH3]C UIUXUFNYAYAMOE-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 15
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 abstract description 11
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract description 8
- 229910000077 silane Inorganic materials 0.000 abstract description 8
- 230000008569 process Effects 0.000 abstract description 3
- 238000013459 approach Methods 0.000 abstract description 2
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 abstract description 2
- 238000005457 optimization Methods 0.000 abstract 1
- -1 siloxanes Chemical class 0.000 description 6
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 5
- PKTOVQRKCNPVKY-UHFFFAOYSA-N dimethoxy(methyl)silicon Chemical compound CO[Si](C)OC PKTOVQRKCNPVKY-UHFFFAOYSA-N 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- GAURFLBIDLSLQU-UHFFFAOYSA-N diethoxy(methyl)silicon Chemical compound CCO[Si](C)OCC GAURFLBIDLSLQU-UHFFFAOYSA-N 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- QRFPECUQGPJPMV-UHFFFAOYSA-N isocyanatomethyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CN=C=O QRFPECUQGPJPMV-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- PHCFIFIBAXEQFZ-UHFFFAOYSA-N bromo(triethoxy)silane Chemical compound CCO[Si](Br)(OCC)OCC PHCFIFIBAXEQFZ-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- CBVJWBYNOWIOFJ-UHFFFAOYSA-N chloro(trimethoxy)silane Chemical compound CO[Si](Cl)(OC)OC CBVJWBYNOWIOFJ-UHFFFAOYSA-N 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- UIDUKLCLJMXFEO-UHFFFAOYSA-N propylsilane Chemical compound CCC[SiH3] UIDUKLCLJMXFEO-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- BOTMPGMIDPRZGP-UHFFFAOYSA-N triethoxy(isocyanatomethyl)silane Chemical compound CCO[Si](OCC)(OCC)CN=C=O BOTMPGMIDPRZGP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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 Table
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
Abstract
The invention discloses a kind of α isocyanatomethyl silane and preparation method thereof, the present invention prepares α isocynate silane using the reaction between halogenated silanes coupling agent and cyanate.Compared with traditional method, this method route is more simple, avoids halogenated silanes to the process of amino silane, is the optimization approach for preparing α isocyanatomethyl silane.
Description
Technical field
The present invention relates to silane coupling agent fields, and in particular to a kind of α isocyanatomethyl silane and preparation method thereof.
Background technique
Isocynate silane contains the isocyanate groups that can participate in reaction and the siloxanes that can carry out moisture-curable
Group.Therefore it is increasingly being applied to the field of polymers, to improve the products such as coating, adhesive to interfaces such as wall, automobiles
Cementability.
The influence of silicon atom of the isocyanate groups due to facing position in α isocyanatomethyl silane has stronger work
Property, therefore isocyanates and the hydroxyl reactivity in Polymer Systems are higher.European Union in 2010 puts into effect ban, public's contact
In article, the amount of organotin catalysts should be lower than 0.1%.Therefore the polyether resin Silante terminated by α isocyanatomethyl gathers
Urethane resin can not add organotin catalysts, be the environmental protection type resin of real meaning during synthesizing and matching glue.
Currently, the research direction of isocynate silane mainly for tend to research about γ-isocyanates propyl silane
Synthesis, the relation technological researching about α isocyanatomethyl silane is less, and isocynate silane mainly uses phosgenation
It is synthesized with carbonic acid derivative high-temperature cracking method, phosgene is more toxic in former approach, then needs to carry out height in latter method
Anneal crack solution, it is harsh to process units and manufacturing technique requirent.
The present invention is mainly reacted using halogenated silanes coupling agent and cyanate under the effect of the catalyst, is prepared into α
Isocynate silane.Compared with traditional method, this method preparation process is simple, avoid halogenated silanes to amino silane mistake
Journey is low relative to conventional method requirement to process units and manufacturing technique requirent；Environmental Safety pollutes small；Yield and purity is high.
Summary of the invention
To solve problems of the prior art, the present invention provides a kind of α isocyanatomethyl silane and its preparation side
Method.
The preparation method of α isocyanatomethyl silane of the invention includes the following steps: α halogenated silanes coupling agent, cyanogen
Hydrochlorate and catalyst are added in solvent, after mixing evenly, are made it completely dissolved, and are heated to 100~140 DEG C, react 1~3h,
After solution is filtered, α isocyanatomethyl silane is made in vacuum distillation；Wherein, α halogenated silanes coupling agent, cyanate and catalysis
Agent is 1:(1.5~2 by the ratio between amount of substance): (0.001~0.005).
Wherein, the chemical general formula of the α halogenated silanes coupling agent are as follows:
Wherein, R1, R2 and R3 are respectively CnH2n+1And OCmH2m+1One of, n >=1, m >=1；X is halogen.
In addition, the X is chlorine or bromine.
In addition, the cyanate is one of Zassol, potassium cyanate and ammonium cyanate.
In addition, the catalyst is nickel complex, nickel complex contains one or both of Cl and N element.
In addition, the solvent is to dimethylamino naphthyridine, 4- pyrroles's yl pyridines, quinoline, n,N-Dimethylaniline, N, N- bis-
One of methylformamide and pyrrolidones.
The invention also includes α isocyanates first made from a kind of preparation method such as above-mentioned α isocyanatomethyl silane
Base silane.
The present invention provides a kind of preparation method of α isocyanatomethyl silane.To prepare the isocyanates with high activity
Silane provides simpler method, improves safety, reduces the cost in this kind of silane preparation process.
Specific embodiment
Below in conjunction with each embodiment, preferred embodiment of the present invention will be described, it should be understood that described herein
Preferred embodiment is only for the purpose of illustrating and explaining the present invention and is not intended to limit the present invention.
Embodiment 1
By the chloro- trimethoxy silane of 180.7g (1mol) α, 130g (2mol) Zassol and 0.292g (0.001mol) nickel
Complex compound is (DME) NiCl2It is added in pyrrolidones, after mixing evenly, is heated to 140 DEG C, reacts 1h, solution is filtered
Afterwards, it is evaporated under reduced pressure, obtains α isocyanatomethyl trimethoxy silane fraction.
Embodiment 2
By the bromo- triethoxysilane of 267.7g (1mol) α, 162g (2mol) potassium cyanate and 1.56g (0.005mol) nickel network
Close object C20H20ClN3Ni is added in quinoline, after mixing evenly, is heated to 100 DEG C, is reacted 2h, and after solution is filtered, decompression is steamed
It evaporates, obtains α isocyanatomethyl triethoxysilane fraction.
Embodiment 3
By 164.7g (1mol) (the chloro- methyl of α) methyl dimethoxysilane (Cl-CH2-Si(CH3) (OCH3)2)、97.5g
(1.5mol) Zassol and 0.292g nickel complex (DME) NiCl2It is added in n,N-Dimethylformamide, after mixing evenly,
140 DEG C are heated to, 1h is reacted, after solution is filtered, vacuum distillation obtains (α isocyanatomethyl) methyl dimethoxysilane
Fraction.
Embodiment 4
By 166g (1mol) (α fluoro-2-methyl) methyldiethoxysilane (F-CH2-Si(CH3)(OC2H5) 2)、102g
(1.7mol) ammonium cyanate and 0.292g nickel complex (DME) NiCl2It is added to N, in N- dimethylaniline, after mixing evenly, adds
Heat reacts 1h to 130 DEG C, and after solution is filtered, vacuum distillation obtains (α isocyanatomethyl) methyldiethoxysilane and evaporates
Point.
Embodiment 5
By 329.2g (1mol) (α astatine-methyl) methyl dimethoxysilane (At-CH2-Si(CH3) (OCH3)2)、105g
(1.6mol) Zassol and 0.28g nickel complex (DME) NiCl2It is added in 4- pyrroles's yl pyridines, after mixing evenly, is heated to
130 DEG C, 1h is reacted, after solution is filtered, vacuum distillation obtains (α isocyanatomethyl) methyl dimethoxysilane fraction.
Embodiment 6
By the iodo- methyltrimethoxysilane (I-CH of 262g (1mol) α2-Si(OCH3)3), 97.5g (1.5mol) Zassol
With 0.27g nickel complex (DME) NiCl2It is added to in dimethylamino naphthyridine, after mixing evenly, is heated to 140 DEG C, reaction
1h, after solution is filtered, vacuum distillation obtains α isocyanatomethyl trimethoxy silane fraction.
The yield of three kinds of isocyanatomethyl silane and purity are as follows:
Yield=product actual mass/product theory quality
Purity: CG-MS makees solvent with heptane, and temperature is 120 DEG C
It can be seen that the preparation side using α isocyanatomethyl silane of the invention from embodiment yield and purity result
The yield of α isocyanatomethyl silane made from method is up to 95%, and purity is up to 97%.
Finally, it should be noted that the foregoing is only a preferred embodiment of the present invention, it is not intended to restrict the invention,
Although the present invention is described in detail referring to the foregoing embodiments, for those skilled in the art, still may be used
To modify the technical solutions described in the foregoing embodiments or equivalent replacement of some of the technical features.
All within the spirits and principles of the present invention, any modification, equivalent replacement, improvement and so on should be included in of the invention
Within protection scope.
Claims (7)
1. a kind of preparation method of α isocyanatomethyl silane, which is characterized in that include the following steps: for α halogenated silanes to be coupled
Agent, cyanate and catalyst are added in solvent, after mixing evenly, are made it completely dissolved, and are heated to 100~140 DEG C, reaction 1
~3h, after solution is filtered, α isocyanatomethyl silane is made in vacuum distillation；Wherein, α halogenated silanes coupling agent, cyanate
It is 1:(1.5~2 that the ratio between amount of substance is pressed with catalyst): (0.001~0.005).
2. the preparation method of α isocyanatomethyl silane according to claim 1, which is characterized in that the α halogenated silanes
The chemical general formula of coupling agent are as follows:
Wherein, R1, R2 and R3 are respectively CnH2n+1And OCmH2m+1One of, n >=1, m >=1；X is halogen.
3. the preparation method of α isocyanatomethyl silane according to claim 2, which is characterized in that the X be chlorine or
Bromine.
4. the preparation method of α isocyanatomethyl silane according to claim 1, which is characterized in that the cyanate is
One of Zassol, potassium cyanate and ammonium cyanate.
5. the preparation method of α isocyanatomethyl silane according to claim 1, which is characterized in that the catalyst is
Nickel complex, nickel complex contain one or both of Cl and N element.
6. the preparation method of α isocyanatomethyl silane according to claim 1, which is characterized in that the solvent is pair
Dimethylamino naphthyridine, 4- pyrroles's yl pyridines, quinoline, N, in accelerine, N,N-dimethylformamide and pyrrolidones
It is a kind of.
7. α isocyanide made from a kind of preparation method of α isocyanatomethyl silane according to claim 1 to 6
Acid esters methyl-monosilane.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811186576.6A CN109438502B (en) | 2018-10-11 | 2018-10-11 | Alpha isocyanate methyl silane and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811186576.6A CN109438502B (en) | 2018-10-11 | 2018-10-11 | Alpha isocyanate methyl silane and preparation method thereof |
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| Publication Number | Publication Date |
|---|---|
| CN109438502A true CN109438502A (en) | 2019-03-08 |
| CN109438502B CN109438502B (en) | 2021-05-07 |
Family
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| Publication number | Publication date |
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| CN109438502B (en) | 2021-05-07 |
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