CN106977721A - A kind of method for hydrolysis of silicone oil monomer - Google Patents
A kind of method for hydrolysis of silicone oil monomer Download PDFInfo
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- CN106977721A CN106977721A CN201710283016.1A CN201710283016A CN106977721A CN 106977721 A CN106977721 A CN 106977721A CN 201710283016 A CN201710283016 A CN 201710283016A CN 106977721 A CN106977721 A CN 106977721A
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- Prior art keywords
- silicone oil
- hydrolysis
- oil monomer
- ring body
- branched chain
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- 229920002545 silicone oil Polymers 0.000 title claims abstract description 70
- 230000007062 hydrolysis Effects 0.000 title claims abstract description 57
- 238000006460 hydrolysis reaction Methods 0.000 title claims abstract description 57
- 239000000178 monomer Substances 0.000 title claims abstract description 50
- 238000000034 method Methods 0.000 title claims abstract description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000000413 hydrolysate Substances 0.000 claims abstract description 21
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 12
- 229940008099 dimethicone Drugs 0.000 claims abstract description 8
- 239000004205 dimethyl polysiloxane Substances 0.000 claims abstract description 8
- 235000013870 dimethyl polysiloxane Nutrition 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 8
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims abstract description 8
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 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 abstract description 7
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 claims abstract description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 239000000047 product Substances 0.000 claims description 5
- 239000002002 slurry Substances 0.000 claims description 2
- 230000008569 process Effects 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- -1 polysiloxane Polymers 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 239000002199 base oil Substances 0.000 description 3
- 239000004519 grease Substances 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 235000015110 jellies Nutrition 0.000 description 2
- 239000008274 jelly Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 108010009736 Protein Hydrolysates Proteins 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- ZXPDYFSTVHQQOI-UHFFFAOYSA-N diethoxysilane Chemical compound CCO[SiH2]OCC ZXPDYFSTVHQQOI-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 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
- C08G77/06—Preparatory processes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Silicon Polymers (AREA)
Abstract
The invention provides a kind of method for hydrolysis of silicone oil monomer, comprise the following steps：Catalyst, ring body and silicone oil monomer are sequentially added in water, is hydrolyzed, branched chain silicone hydrolysate is obtained；The ring body includes octamethylcy-clotetrasiloxane and/or dimethicone mixture；The silicone oil monomer includes the one or more in methltriethoxysilone, monomethyl trimethoxy silane, phenyltriethoxysilane and a phenyltrimethoxysila,e.Present invention employs specific charging sequence and the charging process slowly fed, coordinate specific raw material type so that branched chain type silicone oil monomer hydrolysis efficiency is improved.In an embodiment of the present invention, 91.0% can be reached using the hydrolysis yield of the method for hydrolysis in the present invention.
Description
Technical field
The invention belongs to technical field of organic synthesis, more particularly to a kind of method for hydrolysis of silicone oil monomer.
Background technology
Silicone oil is a kind of polysiloxane of different polymerization degree chain structure, belongs to organo-silicon compound, and it, which is researched and developed, begins
It is to obtain one of industrialized syntholube earliest in 18th century.Silicone oil has a variety of excellent performances：1) it is excellent viscous
Warm nature energy；2) excellent heat endurance；3) excellent thermo oxidative stability；4) excellent electrical insulating property；5) excellent shearing peace
It is qualitative；6) it is nontoxic.Therefore it is obtained for application in many fields.
Branched chain type silicone oil is one kind of silicone oil, because of the introducing of side chain, while a variety of premium properties of silicone oil are kept, is gone back
With following more excellent performance：1st, with more excellent cryogenic property, its condensation point is minimum can as little as about -90 DEG C；2nd, improve
To the compatibility of additive and other oil products.Therefore branched chain type silicone oil is mainly used in the lubricant grease base oil under extremely low temperature.
The production procedure of branched chain type silicone oil is as follows：
Branched chain type silicone oil monomer hydrolysis obtain silicone oil hydrolysate, then under acid or alkaline conditions carry out polymerisation and
Equilibration reaction, then distilled and filtered successively, you can obtain branched chain type silicone oil.Due to constitute silicone oil various chain links be by
What corresponding organic silicon monomer hydrolysis was obtained, therefore the hydrolysis of branched chain type silicone oil monomer is the important step for preparing branched chain type silicone oil.
Obtained hydrolysate is generally hydrolyzed as branched chain type silicone oil monomer using alkyl triethoxysilane or alkyltrichlorosilanes to prepare
Branched chain type silicone oil, but there is following technical barrier in hydrolytic process：1) branched chain type silicone oil monomer reactivity is strong, hydrolysis rate mistake
It hurry up, hydrolytic process is difficult to control；2) may then crosslink reaction when branched chain type silicone oil monomer dosage is excessive causes jelly
Generation.Therefore the hydrolysis difficulty of branched chain type silicone oil monomer is larger.
The content of the invention
It is an object of the invention to provide a kind of method for hydrolysis of silicone oil monomer, the method for hydrolysis in the present invention can be hydrolyzed
Branched chain type silicone oil monomer, and it is higher to hydrolyze yield.
The present invention provides a kind of method for hydrolysis of silicone oil monomer, comprises the following steps：
Catalyst, ring body and silicone oil monomer are sequentially added in water, is hydrolyzed, branched chain silicone hydrolysate is obtained；
The ring body includes octamethylcy-clotetrasiloxane and/or dimethicone mixture；
The silicone oil monomer includes methltriethoxysilone, monomethyl trimethoxy silane, a phenyl triethoxy
One or more in silane and a phenyltrimethoxysila,e.
It is preferred that, the mass ratio of the silicone oil monomer and ring body is (3~10)：(90~97).
It is preferred that, the mass ratio of the silicone oil monomer and ring body is (6~8)：(92~94).
It is preferred that, the gross mass of the silicone oil monomer and ring body is 1 with the mass ratio of the water：(1~1.5).
It is preferred that, the catalyst includes hydrochloric acid and/or sulfuric acid.
It is preferred that, the gross mass of the silicone oil monomer and ring body is 1 with the mass ratio of the catalyst：(0.04~
0.12)。
It is preferred that, the temperature of the hydrolysis is 30~50 DEG C；
The time of the hydrolysis is 3~5 hours.
It is preferred that, the feed time of the silicone oil monomer is 1~2 hour.
It is preferred that, it is further comprising the steps of after the hydrolysis：
The product that the hydrolysis is obtained, which stands to divide, removes sour water, is washed with water to pH value 6~8, obtains branched chain silicone hydrolysis
Thing.
It is preferred that, the temperature of the slurry is 50~70 DEG C.
The invention provides a kind of method for hydrolysis of silicone oil monomer, comprise the following steps：Sequentially added in water catalyst,
Ring body and silicone oil monomer, are hydrolyzed, and obtain branched chain silicone hydrolysate；The ring body include octamethylcy-clotetrasiloxane and/or
Dimethicone mixture；The silicone oil monomer includes methltriethoxysilone, monomethyl trimethoxy silane, one
One or more in phenyl triethoxysilane and a phenyltrimethoxysila,e.Present invention employs specific charging sequence
The charging process slowly fed, coordinates specific raw material type so that branched chain type silicone oil monomer hydrolysis efficiency is improved.In this hair
In bright embodiment, 91.0% can be reached using the hydrolysis yield of the method for hydrolysis in the present invention.
Further, the branched chain type silicone oil of the branched chain silicone hydrolysate synthesis obtained according to present invention hydrolysis has excellent
Cryogenic property and additive compatibility, are mainly used in the lubricant grease base oil under extremely low temperature.
Embodiment
The invention provides a kind of method for hydrolysis of silicone oil monomer, comprise the following steps：
Catalyst, ring body and silicone oil monomer are sequentially added in water, is hydrolyzed, branched chain silicone hydrolysate is obtained；
The ring body includes octamethylcy-clotetrasiloxane and/or dimethicone mixture；
The silicone oil monomer includes methltriethoxysilone, monomethyl trimethoxy silane, a phenyl triethoxy
One or more in silane and a phenyltrimethoxysila,e.
Method for hydrolysis in the present invention can be the hydrolysis of branched chain type silicone oil monomer, and obtained hydrolysate is used to synthesize side chain
Type silicone oil.
In the present invention, the catalyst preferably includes hydrochloric acid and/or sulfuric acid, and the ring body includes the silica of prestox ring four
Alkane and/or dimethicone mixture, the dimethicone mixture (DMC) mainly include the silicon of pregnancy basic ring three
Oxygen alkane (D3), octamethylcy-clotetrasiloxane (D4), decamethylcyclopentaandoxane (D5) and the siloxanes of ten diformazan basic ring six (D6)；Institute
The chain length of hydrolysate can be increased by stating ring body；The silicone oil monomer includes methltriethoxysilone, monomethyl trimethoxy
One or more in silane, phenyltriethoxysilane and a phenyltrimethoxysila,e.
In the present invention, the silicone oil monomer and the mass ratio of ring body are preferably (3~10)：(90~97), more preferably
(6~8)：(92~94), specifically, can be 8 in an embodiment of the present invention:92,6:94 or 10:90；The silicone oil monomer
It is preferably 1 with the gross mass of ring body and the mass ratio of the water：(1~1.5), more preferably 1：(1.1~1.4), specifically,
Can be 1 in embodiments of the invention:1.15 or 1：1.5；The gross mass of the silicone oil monomer and ring body and the catalyst
Mass ratio is preferably 1：(0.04~0.12), more preferably 1：(0.05~0.1), specifically, in an embodiment of the present invention, can
To be 1：0.08、1:0.1 or 1：0.12.
Preferably silicone oil monomer is slowly added dropwise in the present invention, and the time for adding is preferably 1~2 hour, the temperature of the hydrolysis
Preferably 30~50 DEG C, more preferably 35~45 DEG C；The time of the hydrolysis is preferably 3~5 hours, more preferably 4 hours.
The present invention divides after preferably the product after the hydrolysis is stood removes sour water, is then washed with 50~70 DEG C of water
Wash, until product pH value is 6~8, obtain branched chain type silicone oil hydrolysate.
The invention provides a kind of method for hydrolysis of silicone oil monomer, comprise the following steps：Sequentially added in water catalyst,
Ring body and silicone oil monomer, are hydrolyzed, and obtain branched chain silicone hydrolysate；The ring body include octamethylcy-clotetrasiloxane and/or
Dimethicone mixture；The silicone oil monomer includes methltriethoxysilone, monomethyl trimethoxy silane, one
One or more in phenyl triethoxysilane and a phenyltrimethoxysila,e.Present invention employs specific charging sequence
The charging process slowly fed, coordinates specific raw material type so that branched chain type silicone oil monomer hydrolysis efficiency is improved.In this hair
In bright embodiment, 91.0% can be reached using the hydrolysis yield of the method for hydrolysis in the present invention.
Further, the branched chain type silicone oil of the branched chain silicone hydrolysate synthesis obtained according to present invention hydrolysis has excellent
Cryogenic property and additive compatibility, are mainly used in the lubricant grease base oil under extremely low temperature.
In order to further illustrate the present invention, a kind of hydrolysis side of the silicone oil monomer provided with reference to embodiments the present invention
Method is described in detail, but can not be understood as limiting the scope of the present invention.
Embodiment 1
600g water, the 40g concentrated sulfuric acids and 460g octamethylcy-clotetrasiloxanes are sequentially added in reaction vessel, is slowly added dropwise
40g methltriethoxysilones, the time is 1 hour, after adding, and is reacted 3 hours at 40 ± 5 DEG C, stands to divide and removes sour water, with 50
DEG C water washing three times, obtains branched chain silicone hydrolysate.It is computed, hydrolysis yield is 91.0%.
Embodiment 2
750g water, the 50g concentrated sulfuric acids and 470g octamethylcy-clotetrasiloxanes are sequentially added in reaction vessel, is slowly added dropwise
30g monomethyl trimethoxy silanes, the time is 1.5 hours, after adding, and is reacted 4 hours at 40 ± 5 DEG C, stands to divide and removes sour water, uses
60 DEG C of water washings three times, obtain branched chain silicone hydrolysate.It is computed, hydrolysis yield is 89.8%.
Embodiment 3
750g water, the 60g concentrated sulfuric acids and 450g octamethylcy-clotetrasiloxanes are added in reaction vessel, 50g mono- is slowly added dropwise
Phenyl triethoxysilane, the time is 2 hours, after adding, and is reacted 5 hours at 45 ± 5 DEG C, stands to divide and removes sour water, with 60 DEG C of water
Washing three times, obtains branched chain silicone hydrolysate.It is computed, hydrolysis yield is 90.5%.
Comparative example 1：
500g aminomethyl phenyls diethoxy silane and 30g hydrochloric acid are added in reaction vessel, 318g water, time is slowly added dropwise
For 1 hour, 1000g water is then added, is reacted 4 hours at 80 DEG C, stands and point removes sour water, with 60 DEG C of water washings three times, first is obtained
Phenyl silicone oil hydrolysate.It is computed, percent hydrolysis is 84.5%.
Comparative example 2：
600g water, the 40g concentrated sulfuric acids, 300g octamethylcy-clotetrasiloxanes and 200g monomethyls are sequentially added in reaction vessel
Triethoxysilane, the time is 2 hours, after adding, and is reacted 3 hours at 40 ± 5 DEG C, has obtained not flowable jelly.
The present invention is respectively adopted the hydrolysate in embodiment 1~3 and comparative example 1 to synthesize silicone oil, obtained silicone oil performance
As shown in table 1, table 1 is the performance of the silicone oil of hydrolysate synthesis in the embodiment of the present invention 1~3 and comparative example 1.
The performance for the silicone oil that hydrolysate is synthesized in the embodiment of the present invention 1~3 of table 1 and comparative example 1.
As can be seen from Table 1, the method for hydrolysis hydrolysis yield in the present invention is high, hydrolyzes the silicon of obtained hydrolysate synthesis
Oil has excellent high temperature performance, and its cryogenic property is especially protruded.
Described above is only the preferred embodiment of the present invention, it is noted that for the ordinary skill people of the art
For member, under the premise without departing from the principles of the invention, some improvements and modifications can also be made, these improvements and modifications also should
It is considered as protection scope of the present invention.
Claims (10)
1. a kind of method for hydrolysis of silicone oil monomer, comprises the following steps：
Catalyst, ring body and silicone oil monomer are sequentially added in water, is hydrolyzed, branched chain silicone hydrolysate is obtained；
The ring body includes octamethylcy-clotetrasiloxane and/or dimethicone mixture；
The silicone oil monomer includes methltriethoxysilone, monomethyl trimethoxy silane, phenyltriethoxysilane
With the one or more in a phenyltrimethoxysila,e.
2. method for hydrolysis according to claim 1, it is characterised in that the silicone oil monomer and the mass ratio of ring body for (3~
10)：(90~97).
3. method for hydrolysis according to claim 2, it is characterised in that the silicone oil monomer and the mass ratio of ring body for (6~
8)：(92~94).
4. method for hydrolysis according to claim 1, it is characterised in that the gross mass of the silicone oil monomer and ring body with it is described
The mass ratio of water is 1：(1~1.5).
5. method for hydrolysis according to claim 1, it is characterised in that the catalyst includes hydrochloric acid and/or sulfuric acid.
6. method for hydrolysis according to claim 5, it is characterised in that the gross mass of the silicone oil monomer and ring body with it is described
The mass ratio of catalyst is 1：(0.04~0.12).
7. method for hydrolysis according to claim 1, it is characterised in that the temperature of the hydrolysis is 30~50 DEG C；
The time of the hydrolysis is 3~5 hours.
8. method for hydrolysis according to claim 1, it is characterised in that the feed time of the silicone oil monomer is 1~2 small
When.
9. the method for hydrolysis according to claim 1~8 any one, it is characterised in that also include after the hydrolysis following
Step：
The product that the hydrolysis is obtained, which stands to divide, removes sour water, is washed with water to pH value 6~8, obtains branched chain silicone hydrolysate.
10. method for hydrolysis according to claim 9, it is characterised in that the temperature of the slurry is 50~70 DEG C.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710283016.1A CN106977721B (en) | 2017-04-26 | 2017-04-26 | Hydrolysis method of silicone oil monomer |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710283016.1A CN106977721B (en) | 2017-04-26 | 2017-04-26 | Hydrolysis method of silicone oil monomer |
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| CN106977721A true CN106977721A (en) | 2017-07-25 |
| CN106977721B CN106977721B (en) | 2020-11-06 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110003473A (en) * | 2019-04-24 | 2019-07-12 | 中国石油化工股份有限公司 | A kind of preparation method of branched chain silicone oligomer |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6180712B1 (en) * | 1998-08-28 | 2001-01-30 | Dow Corning Silicone Co., Ltd. | Silicone water-based emulsion composition |
| CN1834133A (en) * | 2006-04-17 | 2006-09-20 | 广州天赐有机硅科技有限公司 | Branched benzene siliconic oil |
| US20070213474A1 (en) * | 2004-05-06 | 2007-09-13 | Wacker Chemie Ag | Polysiloxane graft polymer |
| CN103936997A (en) * | 2014-04-29 | 2014-07-23 | 东莞兆舜有机硅新材料科技有限公司 | Organopolysiloxane, and preparation method and application thereof |
| CN103952079A (en) * | 2014-05-15 | 2014-07-30 | 桂林电器科学研究院有限公司 | Photo-cured fluorine-containing organosilicone optical fiber coating and preparation method thereof |
-
2017
- 2017-04-26 CN CN201710283016.1A patent/CN106977721B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6180712B1 (en) * | 1998-08-28 | 2001-01-30 | Dow Corning Silicone Co., Ltd. | Silicone water-based emulsion composition |
| US20070213474A1 (en) * | 2004-05-06 | 2007-09-13 | Wacker Chemie Ag | Polysiloxane graft polymer |
| CN1834133A (en) * | 2006-04-17 | 2006-09-20 | 广州天赐有机硅科技有限公司 | Branched benzene siliconic oil |
| CN103936997A (en) * | 2014-04-29 | 2014-07-23 | 东莞兆舜有机硅新材料科技有限公司 | Organopolysiloxane, and preparation method and application thereof |
| CN103952079A (en) * | 2014-05-15 | 2014-07-30 | 桂林电器科学研究院有限公司 | Photo-cured fluorine-containing organosilicone optical fiber coating and preparation method thereof |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110003473A (en) * | 2019-04-24 | 2019-07-12 | 中国石油化工股份有限公司 | A kind of preparation method of branched chain silicone oligomer |
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