CN115010928A - Method for preparing linear polysiloxane by ring opening of cyclic siloxane - Google Patents
Method for preparing linear polysiloxane by ring opening of cyclic siloxane Download PDFInfo
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- CN115010928A CN115010928A CN202210917966.6A CN202210917966A CN115010928A CN 115010928 A CN115010928 A CN 115010928A CN 202210917966 A CN202210917966 A CN 202210917966A CN 115010928 A CN115010928 A CN 115010928A
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- -1 polysiloxane Polymers 0.000 title claims abstract description 36
- 238000007142 ring opening reaction Methods 0.000 title claims abstract description 28
- 238000000034 method Methods 0.000 title claims abstract description 26
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 239000002904 solvent Substances 0.000 claims abstract description 12
- QABCGOSYZHCPGN-UHFFFAOYSA-N chloro(dimethyl)silicon Chemical compound C[Si](C)Cl QABCGOSYZHCPGN-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000011261 inert gas Substances 0.000 claims abstract description 6
- 125000005233 alkylalcohol group Chemical group 0.000 claims abstract description 5
- 238000002156 mixing Methods 0.000 claims abstract description 3
- 239000000376 reactant Substances 0.000 claims description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 8
- 238000005292 vacuum distillation Methods 0.000 claims description 4
- HTDJPCNNEPUOOQ-UHFFFAOYSA-N hexamethylcyclotrisiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O1 HTDJPCNNEPUOOQ-UHFFFAOYSA-N 0.000 claims description 3
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 125000004398 2-methyl-2-butyl group Chemical group CC(C)(CC)* 0.000 claims description 2
- XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 claims description 2
- IUMSDRXLFWAGNT-UHFFFAOYSA-N Dodecamethylcyclohexasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 IUMSDRXLFWAGNT-UHFFFAOYSA-N 0.000 claims description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N butyl alcohol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 125000005375 organosiloxane group Chemical group 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 description 9
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 238000003760 magnetic stirring Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- VFZRCLLDPCNXPS-UHFFFAOYSA-N 2,2,4,4,6,6,8,8,10,10-decamethyl-1,3,5,7,9,11-hexaoxa-2,4,6,8,10,12-hexasilacyclododecane Chemical compound C[Si]1(C)O[SiH2]O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 VFZRCLLDPCNXPS-UHFFFAOYSA-N 0.000 description 2
- JFEVGJZAJAHAPU-UHFFFAOYSA-N C(CCCCCCCCCCCCCCC)[SiH2]O[SiH2]O[SiH2]O[SiH2]O[SiH2]O[SiH2]O[SiH2]O[SiH3] Chemical compound C(CCCCCCCCCCCCCCC)[SiH2]O[SiH2]O[SiH2]O[SiH2]O[SiH2]O[SiH2]O[SiH2]O[SiH3] JFEVGJZAJAHAPU-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 1
- KWBVOMGZISVLGA-UHFFFAOYSA-N [[[(dimethyl-$l^{3}-silanyl)oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)C KWBVOMGZISVLGA-UHFFFAOYSA-N 0.000 description 1
- MEJKNMVFSMYBHE-UHFFFAOYSA-N [[[[(dimethyl-$l^{3}-silanyl)oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)C MEJKNMVFSMYBHE-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- JZZIHCLFHIXETF-UHFFFAOYSA-N dimethylsilicon Chemical compound C[Si]C JZZIHCLFHIXETF-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/045—Polysiloxanes containing less than 25 silicon atoms
-
- 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
- C07F7/0896—Compounds with a Si-H linkage
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
Abstract
The invention relates to a method for preparing linear polysiloxane by ring opening of cyclic siloxane, which comprises the following steps: under an inert gas atmosphere, mixing organic cyclosiloxane and dimethylchlorosilane according to a molar mass ratio of 1: 1-1: 3, then adding a solvent alkyl alcohol, adding a catalyst N, N-dimethylformamide to carry out ring-opening reaction under the condition of controlling the reaction temperature to be 20-60 ℃, and collecting fractions at the temperature of 60-150 ℃ after the ring-opening reaction is finished by a vacuum rectifying column to obtain a ring-opening organosiloxane product. The method for preparing the linear polysiloxane by the cyclic siloxane is carried out at low temperature, the mixture ratio of raw materials is properly adjusted, a solvent and a catalyst are specifically selected, and the linear polysiloxane with a single structure is prepared and has higher purity.
Description
Technical Field
The invention belongs to the field of fine chemicals preparation, and particularly relates to a method for preparing linear polysiloxane by ring-opening of cyclic siloxane.
Background
The linear polysiloxane is usually kept in a liquid state at room temperature, and has good chemical stability, insulating property and hydrophobic property. The conversion of cyclic siloxanes into linear polysiloxanes is referred to as the ring opening process, in which there are ring opening reactions, generally cationic ring opening, and end-capping polymerization reactions, mainly using catalysts such as strong protic acids or lewis acids, and also using catalysts such as ion exchange resins, acidic minerals, and acidic clays, which are also end-capping polymer catalysts during ring opening, whereas the preparation process produces siloxanes which are generally mixed.
The linear polysiloxane (or called linear polysiloxane) in the market at present is mainly prepared by a mixed type product, and the purity of the product is low. The preparation process of high-purity single linear polysiloxane is relatively rare, and in order to obtain high-purity single-structure linear polysiloxane, the invention develops a method for preparing linear polysiloxane by ring opening and then polymerization end capping of cyclic siloxane.
Disclosure of Invention
In order to solve the technical problems, the invention provides a method for synthesizing organosiloxane with controllable chain length, which can complete the ring-opening reaction of organic cyclosiloxane at a lower temperature to synthesize linear organosiloxane with controllable chain length, and is suitable for large-scale production.
Specifically, the invention provides a method for preparing linear polysiloxane by ring-opening of cyclic siloxane, which comprises the following steps:
under an inert gas atmosphere, mixing organic cyclosiloxane and dimethylchlorosilane according to a molar mass ratio of 1: 1-1: 3, then adding a solvent alkyl alcohol, adding a catalyst N, N-dimethylformamide under the condition of controlling the reaction temperature to be 20-60 ℃ to carry out ring-opening reaction, and collecting fractions within the temperature of 60-150 ℃ from reactants through a vacuum rectifying column after the ring-opening reaction is finished to obtain a linear polysiloxane product.
The above preparation method can be briefly summarized by the following chemical reaction formula, and the linear polysiloxane produced is increased by two silicon atoms based on the number of silicon atoms of the original cyclosiloxane. The linear polysiloxane is (CH) 3 ) 2 Si-0 is chain polymer of unit, one side of the end capping group is dimethyl silicon base, and the other side is hydrogen base end capping.
Preferably, in the method, the catalyst N, N-dimethylformamide accounts for 0.1-5.0% of the total mass fraction of the organic cyclosiloxane, the dimethylchlorosilane and the solvent; preferably, the catalyst N, N-dimethylformamide accounts for 0.5-3.0% of the total mass fraction of the organic cyclosiloxane, the dimethylchlorosilane and the solvent.
Preferably, in the above method, the organic cyclosiloxane is one of hexamethylcyclotrisiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, and dodecamethylcyclohexasiloxane.
Preferably, in the above method, the alkyl alcohol is one or more of isopropyl alcohol, tert-butyl alcohol and 2-methyl-2-butyl alcohol.
Preferably, in the above method, the ring-opening reaction time is 12 to 48 hours, and preferably, the ring-opening reaction time is 24 hours.
Preferably, in the above method, the organic cyclosiloxane and the dimethylchlorosilane are mixed in a molar mass ratio of 1: 1-1: 2.
preferably, in the above process, the reaction temperature is 25 to 50 ℃.
Preferably, in the above method, after the ring-opening reaction is finished, the reactant is collected by a vacuum distillation column at the temperature of 85-100 ℃, 123-148 ℃ or 60-78 ℃.
The invention has the advantages of
The method for preparing the linear polysiloxane is to carry out reaction at low temperature, properly adjust the proportion of raw materials, specifically select a solvent and a catalyst, and obtain the linear polysiloxane with a single structure with higher purity. The preparation process has easily controlled conditions, can be used for reaction preparation at room temperature, and can prepare high-purity linear polysiloxane with a single structure without the highest ring-opening reaction temperature exceeding 60 ℃.
Detailed Description
The raw materials used in the following examples are commercially available and are referred to as follows:
hexamethylcyclotrisiloxane D3 for short
Octamethylcyclotetrasiloxane D4 for short
Decamethylcyclohexasiloxane (DDS) D6
Example 1: preparation of linear dodecamethylhexasiloxane by ring opening of D4
296.6g of D4 and 94.6g of dimethylchlorosiloxane are introduced under an inert gas atmosphere into a four-necked flask equipped with magnetic stirring and temperature measuring means. Subsequently, 75mL of isopropanol was added as a reaction solvent to the four-necked flask. D4, dimethyl chlorosiloxane and catalyst N, N-dimethylformamide accounting for 1% of the total mass of the solvent are added after the temperature of a reaction material body in the flask is stabilized at 50 +/-2 ℃, all reactants are stirred for 24 hours at 50 +/-2 ℃, the reaction is finished, the reactants are subjected to vacuum distillation column to collect fractions within the temperature range of 85-100 ℃, 231g of product 1,1,3,3,5,5,7,7,9,9,11, 11-dodecamethylhexasiloxane is obtained, and the purity of the product is 96.3%.
Nuclear magnetic characterization data of the product: 1 HNMR(400MHz,CDCl 3 ):δ4.70(m,2H,Si-H),0.19(d,J=4.0Hz,12H,HSi(CH 3 ) 2 ),0.08(d,J=4.0Hz,24H,OSi(CH 3 ) 2 ); 13 CNMR(100MHz,CDCl 3 ):δ1.05,0.89,0.73; 29 SiNMR(119MHz,CDCl 3 ):δ-6.95,-19.91,-21.80。
example 2: preparation of hexadecyl octasiloxane by ring opening of D6
223g of D6 and 94.6g of dimethylchlorosiloxane are introduced under an inert gas atmosphere into a four-necked flask equipped with magnetic stirring and temperature measuring means. Subsequently, 95mL of t-butanol was added as a reaction solvent to the four-necked flask. After the temperature of the reaction material in the flask is stabilized at 40 +/-2 ℃, adding D6, dimethyl chlorosiloxane and N, N-dimethylformamide which is a catalyst and accounts for 0.5% of the total mass of the solvent, stirring all reactants at 40 +/-2 ℃ for 24 hours, finishing the reaction, passing the reactants through a vacuum distillation column, collecting fractions within the temperature range of 123-148 ℃, and obtaining 309.6g of products 1,1,3,3,5,5,7,7,9,9,11,11,13,13,15, 15-hexadecyl octasiloxane, wherein the purity of the products is 92.7%.
Nuclear magnetic characterization data of the product: 1 HNMR(400MHz,CDCl 3 ):δ4.69(m,2H,Si-H),0.19(d,J=4.0Hz,12H,HSi(CH 3 ) 2 ),0.08(d,J=4.0Hz,36H,OSi(CH 3 ) 2 ); 13 CNMR(100MHz,CDCl 3 ):δ1.08,0.89,0.72; 29 SiNMR(119MHz,CDCl 3 ):δ-7.08,-20.05,-22.01,-22.35。
example 3: d3 ring opening preparation
222.4g of D3 and 141.9g of dimethyl chlorosiloxane are added into a four-neck flask equipped with a magnetic stirring and temperature measuring device under an inert gas atmosphere, 165ml of 2-methyl-2-butanol is added into the four-neck flask as a reaction solvent, D3, dimethyl chlorosiloxane and catalyst N, N-dimethylformamide accounting for 3.0% of the total mass of the solvent are added after the temperature of a reaction material body in the flask is stabilized at 25 +/-2 ℃, all reactants are stirred for 24 hours at 25 +/-2 ℃, the reaction is finished, the reactants are passed through a vacuum rectification column, fractions within the temperature range of 60-78 ℃ are collected, and 169.7g of product 1,1,3,3,5,5,7,7,9, 9-decamethyl pentasiloxane with the purity of 95.6% is obtained.
Nuclear magnetic characterization data of the product: 1 HNMR(400MHz,CDCl 3 ):δ4.72(br,2H,Si-H),0.19(d,J=4.0Hz,12H,HSi(CH 3 ) 2 ),0.08(d,J=4.0Hz,18H,OSi(CH 3 ) 2 ); 13 CNMR(100MHz,CDCl 3 ):δ1.09,0.90,0.73; 29 SiNMR(119MHz,CDCl 3 ):δ-7.00,-20.01,-22.05。
the above-described embodiments of the present invention are not to be construed as limiting the scope of the present invention, but merely as demonstrating the feasibility and excellent effects of the technical solution of the present invention.
Claims (9)
1. A method for preparing linear polysiloxane by ring-opening of cyclic siloxane, which comprises the following steps:
under an inert gas atmosphere, mixing organic cyclosiloxane and dimethylchlorosilane according to a molar mass ratio of 1: 1-1: 3, then adding a solvent alkyl alcohol, adding a catalyst N, N-dimethylformamide under the condition of controlling the reaction temperature to be 20-60 ℃ to carry out ring-opening reaction, and collecting fractions within the temperature of 60-150 ℃ from reactants through a vacuum rectifying column after the ring-opening reaction is finished to obtain a linear polysiloxane product.
2. The method according to claim 1, wherein the N, N-dimethylformamide catalyst is present in an amount of 0.1-5.0% by mass based on the total mass of the organocyclosiloxane, dimethylchlorosilane and solvent.
3. The method according to claim 2, wherein the N, N-dimethylformamide catalyst is present in an amount of 0.5 to 3.0% by mass based on the total mass fraction of the organocyclosiloxane, dimethylchlorosilane and solvent.
4. The method of claim 1, wherein the organo cyclosiloxane is one of hexamethylcyclotrisiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, and dodecamethylcyclohexasiloxane.
5. The method of claim 1, wherein the alkyl alcohol is one or more of isopropyl alcohol, tert-butyl alcohol, and 2-methyl-2-butyl alcohol.
6. The process according to claim 1, wherein the ring-opening reaction time is 12 to 48 hours.
7. The process according to claim 1, characterized in that the organocyclosiloxane and the dimethylchlorosilane are present in a molar mass ratio of 1: 1-1: 2.
8. the process according to claim 1, wherein the reaction temperature is from 25 to 50 ℃.
9. The method as claimed in claim 1, wherein the reaction mixture is passed through a vacuum distillation column to collect the fractions at 85-100 ℃, 123-148 ℃ or 60-78 ℃ after the ring-opening reaction.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202210917966.6A CN115010928A (en) | 2022-08-01 | 2022-08-01 | Method for preparing linear polysiloxane by ring opening of cyclic siloxane |
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| CN202210917966.6A CN115010928A (en) | 2022-08-01 | 2022-08-01 | Method for preparing linear polysiloxane by ring opening of cyclic siloxane |
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Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02306980A (en) * | 1989-05-19 | 1990-12-20 | Kao Corp | Production of alpha,omega-dihydrogen organopolysiloxane |
| JPH0395190A (en) * | 1989-09-08 | 1991-04-19 | Kao Corp | Production of alpha,omega-dichloroorganopolysiloxane |
| JPH0395191A (en) * | 1989-09-08 | 1991-04-19 | Kao Corp | Alpha-chloro-omega-hydrogen organopolysiloxane and its production |
| US5686641A (en) * | 1996-01-31 | 1997-11-11 | Dow Corning Toray Silicone Co., Ltd. | Method for the preparation of organopentasiloxanes |
| JPH11158188A (en) * | 1997-11-28 | 1999-06-15 | Dow Corning Toray Silicone Co Ltd | Production of alpha, omega-dihydrogenorganopentasiloxane |
| JP2007023021A (en) * | 2005-05-19 | 2007-02-01 | Shin Etsu Chem Co Ltd | New cyclic siloxane compound and method for producing the same |
| CN1907988A (en) * | 2006-07-26 | 2007-02-07 | 浙江大学 | Line-type polymethylvinylsiloxane with chlorine-terminated and synthesis method thereof |
| CN101298498A (en) * | 2008-06-20 | 2008-11-05 | 华南理工大学 | Alkoxy end-capped linear polysiloxane resin acceptor and synthetic method thereof |
| JP2015074751A (en) * | 2013-10-10 | 2015-04-20 | 信越化学工業株式会社 | Silicone resin composition, laminate using the composition, and led device having the laminate |
| CN105384934A (en) * | 2015-09-21 | 2016-03-09 | 江西蓝星星火有机硅有限公司 | Preparation method of terminal hydrogen-containing silicone oil |
| CN113912849A (en) * | 2020-07-07 | 2022-01-11 | 北京化工大学 | Method for preparing hydrogen-terminated silicone oil and hydrogen-terminated silicone oil obtained by method |
-
2022
- 2022-08-01 CN CN202210917966.6A patent/CN115010928A/en active Pending
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|---|---|---|---|---|
| JPH02306980A (en) * | 1989-05-19 | 1990-12-20 | Kao Corp | Production of alpha,omega-dihydrogen organopolysiloxane |
| JPH0395190A (en) * | 1989-09-08 | 1991-04-19 | Kao Corp | Production of alpha,omega-dichloroorganopolysiloxane |
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| US5686641A (en) * | 1996-01-31 | 1997-11-11 | Dow Corning Toray Silicone Co., Ltd. | Method for the preparation of organopentasiloxanes |
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| JP2015074751A (en) * | 2013-10-10 | 2015-04-20 | 信越化学工業株式会社 | Silicone resin composition, laminate using the composition, and led device having the laminate |
| CN105384934A (en) * | 2015-09-21 | 2016-03-09 | 江西蓝星星火有机硅有限公司 | Preparation method of terminal hydrogen-containing silicone oil |
| CN113912849A (en) * | 2020-07-07 | 2022-01-11 | 北京化工大学 | Method for preparing hydrogen-terminated silicone oil and hydrogen-terminated silicone oil obtained by method |
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| Title |
|---|
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