CN104829838A - Preparation method of hydroxyl terminated polyfluorosiloxane - Google Patents
Preparation method of hydroxyl terminated polyfluorosiloxane Download PDFInfo
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- CN104829838A CN104829838A CN201510226525.1A CN201510226525A CN104829838A CN 104829838 A CN104829838 A CN 104829838A CN 201510226525 A CN201510226525 A CN 201510226525A CN 104829838 A CN104829838 A CN 104829838A
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- fluorosilicone
- hydroxy
- capped poly
- end capped
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- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- -1 polyfluorosiloxane Polymers 0.000 title abstract description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 title abstract 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- 239000003999 initiator Substances 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 10
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 10
- MDHDICCDAKVKIT-UHFFFAOYSA-N dihydroxy(diphenyl)silane;lithium Chemical compound [Li].C=1C=CC=CC=1[Si](O)(O)C1=CC=CC=C1 MDHDICCDAKVKIT-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000007142 ring opening reaction Methods 0.000 claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000000129 anionic group Chemical group 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims abstract description 4
- 238000009835 boiling Methods 0.000 claims abstract description 3
- 239000011261 inert gas Substances 0.000 claims abstract description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 10
- 238000012653 anionic ring-opening polymerization Methods 0.000 claims description 7
- BIFQHCGLXZWNLN-UHFFFAOYSA-N 2,2,6-trifluoro-4-methyl-4-propyl-1,3,5,2,4,6-trioxatrisilinane Chemical compound CCC[Si]1(C)O[SiH](F)O[Si](F)(F)O1 BIFQHCGLXZWNLN-UHFFFAOYSA-N 0.000 claims description 6
- 229920005560 fluorosilicone rubber Polymers 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 238000010792 warming Methods 0.000 claims description 4
- 238000004364 calculation method Methods 0.000 claims description 2
- 230000006837 decompression Effects 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- 238000013461 design Methods 0.000 claims description 2
- 230000000977 initiatory effect Effects 0.000 claims description 2
- 238000009826 distribution Methods 0.000 abstract description 15
- 238000007086 side reaction Methods 0.000 abstract description 3
- 229920001971 elastomer Polymers 0.000 abstract description 2
- 230000008901 benefit Effects 0.000 abstract 2
- FGZFESWHQXSPJU-UHFFFAOYSA-N 2-methyl-2-(3,3,3-trifluoropropyl)-1,3,5,2,4,6-trioxatrisilinane Chemical compound FC(F)(F)CC[Si]1(C)O[SiH2]O[SiH2]O1 FGZFESWHQXSPJU-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 239000003566 sealing material Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000002500 ions Chemical group 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 2
- WTQAKAPKTROVFY-UHFFFAOYSA-N C[SiH]1O[Si](O[Si](O1)(CCC)F)(F)F Chemical compound C[SiH]1O[Si](O[Si](O1)(CCC)F)(F)F WTQAKAPKTROVFY-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 229960000935 dehydrated alcohol Drugs 0.000 description 1
- 238000004807 desolvation Methods 0.000 description 1
- OLLFKUHHDPMQFR-UHFFFAOYSA-N dihydroxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](O)(O)C1=CC=CC=C1 OLLFKUHHDPMQFR-UHFFFAOYSA-N 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005987 sulfurization reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Silicon Polymers (AREA)
Abstract
The invention relates to a preparation method of hydroxyl terminated polyfluorosiloxane. In the provided preparation method, diphenyl silanediol lithium is taken as the non-balance initiator to trigger trifluoropropyl methyl cyclotrisiloxane to carry out anionic ring-opening and polymerization reactions under the protection of inert gas at a room temperature, when the viscosity is stable during the reaction process, a water solution of a terminating agent is added, and finally the pressure is reduced to remove the substances with low boiling points so as to obtain the hydroxyl terminated polyfluorosiloxane. The molecular weight of the product can be controlled by the using amount of the initiator; and solved is the problem that the molecular weight of product cannot be easily controlled in the prior art because the water and the reaction system are not compatible; and moreover, the reconnection and redistribution side reactions during the process of anionic ring-opening and polymerization reactions can be effectively inhibited by the macromolecular phenyl groups. The prepared hydroxyl terminated polyfluorosiloxane has the advantages of controllable molecular weight, narrow molecular weight distribution, and stable and uniform quality. The product can be used as raw rubber of alcohol-free room-temperature-vulcanized fluorosilicone, can be widely applied to the field of domestic/military oil-resistant sealing materials, and has a good economic benefit and promotion value.
Description
Technical field
The invention belongs to technical field of chemistry, relate to a kind of preparation method of hydroxy-end capped poly-fluorosilicone.
Background technology
Hydroxy-end capped poly-fluorosilicone, structural formula
as the rubber of dealcoholizing-type liquid fluorosilicone rubber, trifluoropropyl group in molecular structure gives resistance to fuel oil, the high and low temperature resistance of trifluoropropyl siloxane excellence, and dealcoholizing-type liquid fluorosilicone rubber gets final product sulfuration at ambient temperature, so more convenient compared to high temperature vulcanized solid trifluoropropyl siloxane processing, range of application is wider, better can be applied to the oil resistant field of sealing technology of China's national defense, aviation etc.
The preparation of hydroxy-end capped poly-fluorosilicone generally adopts methyl trifluoro propyl cyclotrisiloxane (D
3f) under the catalysis of the silicon alkoxide of balance initiator sodium hydroxide, potassium hydroxide or Tetramethylammonium hydroxide, anionic ring-opening polymerization is carried out, as patent CN 101376709A.On the one hand, the strong electrophilic inductive effect of trifluoro propyl causes D
3the anionic ring-opening polymerization speed of F is fast, and there is strong " inventing a charge against " and " distributing again " side reaction in polymerization process, fully reaching equilibrium stage, its linear polysiloxane proportion is only 10 ~ 20%, causes polymerisate heterogeneity, molecular weight distribution wide; On the other hand, polymerization reaction late stage system viscosity is large, end-capping reagent H
2the uncompatibility of O and polymerization system causes end-blocking poor effect, molecular weight poor controllability, unstable product quality.
Summary of the invention
For solving the problem, the invention provides a kind of preparation method of hydroxy-end capped poly-fluorosilicone, this preparation technology is simple, molecular weight product is controlled, narrow molecular weight distribution, being suitable for industrialization promotion.
The technical solution used in the present invention is as follows:
A preparation method for hydroxy-end capped poly-fluorosilicone, comprises the steps:
(1) polymerization process: under protection of inert gas, under the initiation of non-equilibrium property negatively charged ion ring opening initiator, anionic ring-opening polymerization is carried out after trifluoro propyl methyl cyclotrisiloxane decompression dehydration, controlling temperature of reaction is 25 ~ 80 DEG C, until reaction system viscosity is constant;
(2) capping process: after reaction system viscosity is constant, adds end-capping reagent H
2o, continues reaction 2 ~ 8h;
(3) de-low process of boiling: reaction system is under reduced pressure warming up to 120 DEG C ~ 180 DEG C, removes low-boiling-point substance, and the time is 1 ~ 3h, obtains water white hydroxy-end capped poly-fluorosilicone.
Preferably, in step (1), described non-equilibrium property negatively charged ion ring opening initiator is Diphenylsilanediol lithium, and structural formula is
Preferably, in step (1), the described design molecular weight according to hydroxy-end capped poly-fluorosilicone calculates, calculation formula is: the consumption=228 × m/M of unbalanced type anionic initiator, wherein, m is the quality of trifluoro propyl methyl cyclotrisiloxane, and M is the molecular weight of hydroxy-end capped poly-fluorosilicone.
Preferably, in step (2), described end-capping reagent H
2the consumption of O is 0.1% ~ 1% of trifluoro propyl methyl cyclotrisiloxane quality.
Preferably, in step (3), after described reduced pressure treatment, the pressure condition of reaction system is 133 ~ 1330Pa.
Preferably, in step (3), described temperature rise rate is 1 ~ 10 DEG C/min.
Preferably, the molecular weight of hydroxy-end capped poly-fluorosilicone that prepared by aforesaid method is 10
3~ 10
5.
Adopt hydroxy-end capped poly-fluorosilicone prepared by the preparation method of hydroxy-end capped poly-fluorosilicone of the present invention.
Hydroxy-end capped poly-fluorosilicone prepared by the method for the invention is preparing the application in dealcoholizing-type liquid fluorosilicone rubber.
The preparation method of hydroxy-end capped poly-fluorosilicone of the present invention, adopts D
3f is monomer, under the catalysis of Diphenylsilanediol lithium, carry out ring-opening polymerization, is controlled the molecular weight of hydroxy-end capped poly-fluorosilicone, can obtain molecular weight 10 by the consumption of initiator
3~ 10
5the product of narrow molecular weight distribution adjustable in scope, quality product stable homogeneous, and preparation technology is simple, is applicable to industrialization promotion.
Beneficial effect of the present invention:
1. non-equilibrium property initiator inhibits D
3" inventing a charge against " and " distributing again " side reaction in F negatively charged ion ring opening process, makes molecular weight of product narrowly distributing, product stable homogeneous.
2. controlled the molecular weight of hydroxy-end capped poly-fluorosilicone by the consumption of non-equilibrium property initiator, solve end-capping reagent H
2the problem that molecular weight is uncontrollable, product batches is unstable that O and system uncompatibility cause.
3. use non-equilibrium property initiator to cause D
3f anionic ring-opening polymerization, eliminates in initiator and last handling process, simplifies production technique.
4. at room temperature, non-equilibrium property initiator causes D
3f anionic ring-opening polymerization, energy-saving and cost-reducing, be beneficial to industrialization promotion.
Accompanying drawing explanation
The hydroxy-end capped poly-fluorosilicone of Fig. 1
1h NMR
Concrete embodiment
Below in conjunction with embodiment, the present invention is described in further detail.In an embodiment, unless otherwise stated, all parts and percentage ratio are all benchmark with weight.
Experimental technique
The synthesis of Diphenylsilanediol lithium
Under nitrogen protection; 8.4g lithium hydroxide and 21.6g Diphenylsilanediol add with in water trap, condenser and churned mechanically four mouthfuls of reaction flasks; add the mixed solvent 500g (m/m=1/1) of dehydrated alcohol and hexanaphthene; be heated to 80 DEG C of system backflows, ensure in reaction process that the water generated is separated in time from system, isothermal reaction 24h; desolvation obtains faint yellow solid powder 28.1g; productive rate 93.7%, sealing is filled nitrogen and is preserved, as D
3f anionic ring-opening polymerization initiator.
The molecular weight of hydroxy-end capped poly-fluorosilicone adopt proton nmr spectra (
1h NMR) measure, result is as Fig. 1, and relative molecular weight and molecular weight distribution adopt gel permeation chromatography (GPC) to measure, solvent: tetrahydrofuran (THF).
Embodiment 1
By 1000g D
3f joins in polymeric kettle, be warming up to 40 DEG C, dewater 1h under 0.01MPa, drying nitrogen is taken a breath after 3 times and is down to room temperature, adds Diphenylsilanediol lithium 7.60g, stirs, controlling temperature of reaction is 25 ~ 80 DEG C, system viscosity slowly increases, and is polymerized to reaction system viscosity constant, adds 5.0g end-capping reagent H
2continue reaction 4h after O, then reduce pressure 400Pa, and heat-up rate 5 DEG C/min is warming up to 150 DEG C, removes low-boiling-point substance 2h, obtained water white hydroxy-end capped poly-fluorosilicone, cooling, discharging, product
1as shown in Figure 1, molecular weight and the distribution results thereof of product list in table 1 to H NMR.
Embodiment 2
Repeat the step described in embodiment 1, just add Diphenylsilanediol lithium 22.8g.Molecular weight and the distribution results thereof of product list in table 1.
Embodiment 3
Repeat the step described in embodiment 1, just add Diphenylsilanediol lithium 4.56g.Molecular weight and the distribution results thereof of product list in table 1.
Embodiment 4
Repeat the step described in embodiment 1, just add Diphenylsilanediol lithium 45.6g.Molecular weight and the distribution results thereof of product list in table 1.
Embodiment 5
Repeat the step described in embodiment 1, just add H
2o 2.0g.Molecular weight and the distribution results thereof of product list in table 1.
Embodiment 6
Repeat the step described in embodiment 1, just add H
2o 10.0g.Molecular weight and the distribution results thereof of product list in table 1.
Comparative example 1
Repeat the step described in embodiment 1, just molecular weight of product end-capping reagent H in polymerization process
2o controls, H
2the consumption of O is 0.6g, and catalyzer uses sodium hydroxide silicon alkoxide.Molecular weight and the distribution results thereof of product list in table 1.
Comparative example 2
Repeat the step described in embodiment 1, just molecular weight of product end-capping reagent H in polymerization process
2o controls, H
2the consumption of O is 0.6g, and catalyzer uses Tetramethylammonium hydroxide silicon alkoxide.Molecular weight and the distribution results thereof of product list in table 1.
Comparative example 3
Repeat the step described in embodiment 1, just molecular weight of product end-capping reagent H in polymerization process
2o controls, H
2the consumption of O is 0.6g, and catalyzer uses potassium hydroxide silicon alkoxide.Molecular weight and the distribution results thereof of product list in table 1.
The measurement result of the hydroxy-end capped poly-fluorosilicone molecular weight of table 1 and molecular weight distribution
By reference to the accompanying drawings the specific embodiment of the present invention is described although above-mentioned; but not limiting the scope of the invention; one of ordinary skill in the art should be understood that; on the basis of technical scheme of the present invention, those skilled in the art do not need to pay various amendment or distortion that creative work can make still within protection scope of the present invention.
Claims (9)
1. a preparation method for hydroxy-end capped poly-fluorosilicone, is characterized in that, comprise the steps:
(1) polymerization process: under protection of inert gas, under the initiation of non-equilibrium property negatively charged ion ring opening initiator, anionic ring-opening polymerization is carried out after trifluoro propyl methyl cyclotrisiloxane decompression dehydration, controlling temperature of reaction is 25 ~ 80 DEG C, until reaction system viscosity is constant;
(2) capping process: after reaction system viscosity is constant, adds end-capping reagent H
2o, continues reaction 2 ~ 8h;
(3) de-low process of boiling: reaction system is under reduced pressure warming up to 120 DEG C ~ 180 DEG C, removes low-boiling-point substance, and the time is 1 ~ 3h, obtains water white hydroxy-end capped poly-fluorosilicone.
2., in the preparation method of hydroxy-end capped poly-fluorosilicone according to claim 1, it is characterized in that: in step (1), described non-equilibrium property negatively charged ion ring opening initiator is Diphenylsilanediol lithium, and structural formula is
3. in the preparation method of hydroxy-end capped poly-fluorosilicone according to claim 1, it is characterized in that: in step (1), the described design molecular weight according to hydroxy-end capped poly-fluorosilicone calculates, calculation formula is: the consumption=228 × m/M of unbalanced type anionic initiator, wherein, m is the quality of trifluoro propyl methyl cyclotrisiloxane, and M is the molecular weight of hydroxy-end capped poly-fluorosilicone.
4., in the preparation method of hydroxy-end capped poly-fluorosilicone according to claim 1, it is characterized in that: in step (2), described end-capping reagent H
2the consumption of O is 0.1% ~ 1% of trifluoro propyl methyl cyclotrisiloxane quality.
5., in the preparation method of hydroxy-end capped poly-fluorosilicone according to claim 1, it is characterized in that: in step (3), after described reduced pressure treatment, the pressure condition of reaction system is 133 ~ 1330Pa.
6., in the preparation method of hydroxy-end capped poly-fluorosilicone according to claim 1, it is characterized in that: in step (3), described temperature rise rate is 1 ~ 10 DEG C/min.
7., in the preparation method of hydroxy-end capped poly-fluorosilicone according to claim 1, it is characterized in that: the molecular weight of described hydroxy-end capped poly-fluorosilicone is 10
3~ 10
5.
8. the hydroxy-end capped poly-fluorosilicone prepared of the preparation method of the arbitrary described hydroxy-end capped poly-fluorosilicone of claim 1-7.
9. hydroxy-end capped poly-fluorosilicone according to claim 8 is preparing the application in dealcoholizing-type liquid fluorosilicone rubber.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105348537A (en) * | 2015-10-27 | 2016-02-24 | 浙江理工大学 | Fluorosilicone functional macromonomer with alkene double bond on single end and preparation method thereof |
| CN106349277A (en) * | 2016-08-24 | 2017-01-25 | 山东大学 | Method for preparing alkoxy-terminated polymethyltrifluoropropyl siloxane oligomers |
| CN109851787A (en) * | 2017-11-30 | 2019-06-07 | 深圳市冠恒新材料科技有限公司 | A kind of fluorine silicon rubber base glue and preparation method thereof |
| CN109851786A (en) * | 2017-11-30 | 2019-06-07 | 深圳市冠恒新材料科技有限公司 | A kind of fluorine silicon rubber base glue and preparation method thereof |
| CN111635503A (en) * | 2020-06-29 | 2020-09-08 | 浙江福斯特新材料研究院有限公司 | Fluorosilicone modified epoxy resin, preparation method and application thereof |
| CN113881029A (en) * | 2021-10-09 | 2022-01-04 | 万华化学集团股份有限公司 | Polysiloxane end-capped modified copolycarbonate and preparation method thereof |
| CN115819773A (en) * | 2022-05-27 | 2023-03-21 | 浙江开化合成材料有限公司 | Preparation method of high-temperature-resistant benzyl silicone oil with narrow molecular weight distribution |
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| CN106349277A (en) * | 2016-08-24 | 2017-01-25 | 山东大学 | Method for preparing alkoxy-terminated polymethyltrifluoropropyl siloxane oligomers |
| CN106349277B (en) * | 2016-08-24 | 2019-03-26 | 山东大学 | A method of preparing alkoxy end-capped poly- methyl trifluoro propyl siloxane oligomer |
| CN109851787A (en) * | 2017-11-30 | 2019-06-07 | 深圳市冠恒新材料科技有限公司 | A kind of fluorine silicon rubber base glue and preparation method thereof |
| CN109851786A (en) * | 2017-11-30 | 2019-06-07 | 深圳市冠恒新材料科技有限公司 | A kind of fluorine silicon rubber base glue and preparation method thereof |
| CN111635503A (en) * | 2020-06-29 | 2020-09-08 | 浙江福斯特新材料研究院有限公司 | Fluorosilicone modified epoxy resin, preparation method and application thereof |
| CN113881029A (en) * | 2021-10-09 | 2022-01-04 | 万华化学集团股份有限公司 | Polysiloxane end-capped modified copolycarbonate and preparation method thereof |
| CN115819773A (en) * | 2022-05-27 | 2023-03-21 | 浙江开化合成材料有限公司 | Preparation method of high-temperature-resistant benzyl silicone oil with narrow molecular weight distribution |
| CN115819773B (en) * | 2022-05-27 | 2023-10-03 | 浙江开化合成材料有限公司 | Preparation method of high-temperature-resistant benzyl silicone oil with narrow molecular weight distribution |
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| CN104829838B (en) | 2017-04-05 |
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