CN1712429A - Preparation of methylhydropolysiloxane containing trimethylsilyl end group - Google Patents
Preparation of methylhydropolysiloxane containing trimethylsilyl end group Download PDFInfo
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- CN1712429A CN1712429A CN 200410048981 CN200410048981A CN1712429A CN 1712429 A CN1712429 A CN 1712429A CN 200410048981 CN200410048981 CN 200410048981 CN 200410048981 A CN200410048981 A CN 200410048981A CN 1712429 A CN1712429 A CN 1712429A
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- water
- methyl
- oxane
- methylhydrogenpolysi
- hydrochloric acid
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 42
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims abstract description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000005051 trimethylchlorosilane Substances 0.000 claims abstract description 11
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 10
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000003960 organic solvent Substances 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 20
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 claims description 20
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 17
- 239000000413 hydrolysate Substances 0.000 claims description 12
- 229920001843 polymethylhydrosiloxane Polymers 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 2
- -1 removing SiCl group Substances 0.000 abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- KTQYJQFGNYHXMB-UHFFFAOYSA-N dichloro(methyl)silicon Chemical compound C[Si](Cl)Cl KTQYJQFGNYHXMB-UHFFFAOYSA-N 0.000 abstract 1
- 235000011167 hydrochloric acid Nutrition 0.000 abstract 1
- 239000005048 methyldichlorosilane Substances 0.000 abstract 1
- 238000004821 distillation Methods 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000010409 thin film Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 3
- 241000282326 Felis catus Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 230000006353 environmental stress Effects 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 229940050176 methyl chloride Drugs 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical group 0.000 description 1
- YGZSVWMBUCGDCV-UHFFFAOYSA-N chloro(methyl)silane Chemical compound C[SiH2]Cl YGZSVWMBUCGDCV-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000032696 parturition Effects 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
Landscapes
- Silicon Polymers (AREA)
Abstract
Production of methyl hydropolysilicone containing trimethyl-silyl-terminal group is carried out by reacting methyl dichlorosilane with trimethyl-chlorosilane and 5 mol water at most in insoluble organic solvent below density 0.9kg/l, generating partial hydrolytic product and gasified hydrogen chloride, removing SiCl group, water treating hydrolytic product, forming chlorhydric acid, separating volatile circular methyl hydrosilicone, full or partially banlacning to generate low-volatile and straight-chain methyl hydropolysilicone.
Description
Technical field
The present invention relates to a kind of method that contains the methylhydrogenpolysi,oxane of trimethylsilyl end groups by dimethyl dichlorosilane (DMCS), trimethylchlorosilane and water preparation.
Background technology
Some open in order to the method for preparing methylhydrogenpolysi,oxane.For example, in this respect can be with reference to US-A-2,758,124.Wherein, dimethyl dichlorosilane (DMCS) and trimethylchlorosilane and super large water gaging reaction.Yet, this method be difficult for being controlled and cause the polysiloxane chain branching or even product coagulate gelation.Formed HCl then becomes hydrochloric acid.
DE-A-1 125 180 has described a kind of method, wherein in the first step, and dimethyl dichlorosilane (DMCS) and trimethylchlorosilane, every mole of hydrolyzable chlorine is used from 1 mole of water of concentrated hydrochloric acid and is come hydrolysis.This concentrated hydrochloric acid contains tetrahydrofuran (THF).In second step, this crude hydrolysates is mixed with big water gaging.The oily matter that so makes has resistant function to gelation.Yet in this method, the concentrated hydrochloric acid and the dilute hydrochloric acid that contain tetrahydrofuran (THF) in a large number of giving birth to can not be made with extra care cost-effectively.
EP-A 0967236 discloses then and has a kind ofly contained the method for the methylhydrogenpolysi,oxane of trimethylsilyl end groups in order to preparation, and the hydrogenchloride overwhelming majority that is wherein produced is recyclable.
Summary of the invention
The present invention relates to the method that a kind of preparation contains the methylhydrogenpolysi,oxane of trimethylsilyl end groups, wherein
In first step, be lower than in the presence of 0.9kg/l, the water-insoluble organic solvent in density, with respect to every mole of hydrolyzable chlorine, dimethyl dichlorosilane (DMCS) and trimethylchlorosilane and 0.5 mole of water reaction and produce partial hydrolysate and gaseous hydrogen chloride at the most,
In second step, for removing the SiCl group of still retaining,, form hydrochloric acid with the described partial hydrolysate of water treatment, and
In third step, the ring-like methyl hydrogen siloxane of the made easy evaporable of first and/or second step is separated, and all or part of balance in addition and generate low-volatile, as to be mainly straight chain type methylhydrogenpolysi,oxane.
With regard to viewpoint of the present invention, the temperature that density data relates to is that 20 ℃ and pressure are environmental stresss, i.e. 900 to 1,100 hundred pascals.
Hydrolyzable chlorine is that the form that is the SiCl base exists.In first step, every mole of hydrolyzable chlorine, preferred at least 0.3 mole of water of using.
With regard to viewpoint of the present invention, water-insoluble organic solvents is meant that the solubleness of solvent is lower than 1g solvent/100g water under 25 ℃ of temperature and the environmental stress (promptly between 900 to 1,100 hundred pascals).
Used in the methods of the invention water-insoluble examples of solvents is: toluene, dimethylbenzene, tetracol phenixin and octane, solvent is preferably toluene.
The partial hydrolysate that forms in first step reaches the optional end capped methylhydrogenpolysi,oxane of OH-by Cl-end-blocking and trimethyl silyl-end-blocking and ring-like methyl hydrogen siloxane is formed.
The content that still is present in the SiCl base in the partial hydrolysate is preferably 0.5 to 5 weight %, more preferably 1.0 to 2 weight %.
Implement first step of the present invention, temperature is preferably 0 to 80 ℃ for good, and more preferably 10% to 30 ℃, pressure is under environment atmospheric pressure, i.e. 900 to 110,000 pascals.
The hydrogen chloride gas that is produced in the first step can be directly used in other processing, for example: prepare methyl chloride with methyl alcohol, and then it is synthetic to be used for methyl chlorosilane.Therefore chlorine can recycle and not be released in the surrounding environment.
In second step, partial hydrolysate institute is chloride all reacts with water.The hydrochloric acid that forms like this, its hydrogen chloride content is preferably 3 to 20 weight %, more preferably 5 to 10 weight %.
In a specific embodiments of the inventive method, formed hydrogenchloride is as the water source in the first step in second step.Formed hydrochloric acid in second step, preferably at least 90% is used in the first step, and more preferably at least 95%.
In a preferred embodiment of the inventive method, institute's water consumption is enough at the most in second step, and the water that forms hydrochloric acid with toilet transforms in first step fully.
The chain length of the methylhydrogenpolysi,oxane that the present invention is prepared and viscosity are controlled via the weight ratio of used dimethyl dichlorosilane (DMCS) and trimethylchlorosilane.The weight ratio of dimethyl dichlorosilane (DMCS) and trimethylammonium nitrogen silane is preferably 100: 1 to 2: 1, more preferably 50: 1 to 5: 1.
Implement second step of the inventive method, temperature is preferably 0 to 100 ℃, and more preferably 10 to 60 ℃, pressure is under environment atmospheric pressure, i.e. 900 to 1,100 hundred pascals.
In the third step of the inventive method, evaporable composition branch is to separate after second step easily.The enforcement of this mask work more preferably divides and does two stages enforcements preferably by distillation.The density that this easy evaporable composition branch is ring-like methyl chloride siloxanes and water-insoluble organic solvents is lower than 0.9kg/l.In the first distillation stage, water-insoluble organic solvents is preferentially to remove and capable of circulation to first reactions steps.In stage, preferably ring-like methyl hydrogen siloxane is separated its balance in addition in third step at after-fractionating.
Implemented for the first distillation stage, temperature is preferably 50 to 150 ℃, and more preferably 60 to 120 ℃, absolute pressure is 50 to 50,000 pascals.
Implement the after-fractionating stage, temperature is preferably 80 to 200 ℃, and more preferably 120 to 160 ℃, absolute pressure is 1 to 3,000 pascal.
Balance according to the inventive method third step is preferably implemented in the presence of equilibrium catalyst.Equilibrium catalyst is preferably the strongly-acid ion-exchanger, more preferably uses with the polystyrene to be contact and to contain functionalized sulfonic group person.This catalyzer can any expection mode contact with the mixture of ready to balance.Preferably, this equilibrium catalyst is preferably packed in the tubular reactor in the mode of expanded bed, but or can be packing layer in case of necessity.
In the third step of the inventive method, this thin-film evaporator phlegma of gained is to contact with catalyzer in reactor.At period of contact, be lower than the distillate overwhelming majority that the water-insoluble organic solvents of 0.9kg/l forms through balance by volatility methyl hydrogen siloxane and density, mass fraction with contained volatility methyl hydrogen siloxane in the distillate is a benchmark, preferred 80 to 95 weight % are through balance, form volatility lower, mainly be the methylhydrogenpolysi,oxane of straight chain type.
Counter-balanced cyclenes mixture preferably includes the toluene up to 60 weight % in the third step of the inventive method, especially when the distillate that uses from first and second distillation stage, however the toluene of special preferred 15 to the 25 weight % in north.
Balance according to the inventive method third step can be implemented in the reactor of any hope, for example: and steel basin and tube-type reactor, preferably use tube-type reactor.
In the third step of the inventive method, equilibrated mixture to be performed can apply to catalyst bed from cat head, or at the bottom of tower to overhead streams via compensation tower, preferably by pump from tower bottom flow to cat head.
The critical factor that influences balanced degree is: catalyzer usage quantity, the residence time and temperature.
In balance of the present invention, be preferably 1 minute to 120 minutes duration of contact, more preferably 2 to 30 minutes better.
The temperature that is adopted when implementing balance of the present invention is preferably-30 ℃ to+200 ℃, and more preferably 0 to 30 ℃, pressure is ambient atmosphere pressure, promptly about 900 to 110,000 pascals.
Implement method of the present invention and can adopt batch-type, semi continuous or fully continuous type, the preferred fully continuous type program of using three steps in interconnective equipment.
Description of drawings
Shown in Figure 1 is the synoptic diagram of a preferred embodiment of the inventive method.
Embodiment
Shown in Figure 1 is a preferred embodiment of the inventive method
In first step, dimethyl dichlorosilane (DMCS) and trimethylchlorosilane are to add in the annular-pipe reactor (1) via pipeline (5), and hydrochloric acid is to add via pipeline (10), and are to add via pipeline (12) from the distillate of thin-film evaporator (4).Gaseous hydrogen chloride is to remove via pipeline (6), and prepared partial hydrolysate is to remove via pipeline (7).
Described partial hydrolysate is to be metered into annular-pipe reactor (2) via pipeline (7), and water is to be metered into annular-pipe reactor (2) via pipeline (8).
Afterwards, all reaction mixtures are to be added in the separator (3) via pipeline (9).In this place, hydrochloric acid is separated out as the bottom, and via pipeline (10) it is circulated to annular-pipe reactor (1).Top then is added to the distillation stage (4) via pipeline (11) mutually.Evaporable composition branch then is circulated to annular-pipe reactor (1) via pipeline (12) easily.The distillate fluid (14) that is produced in the distillation stage (4) then is added in the balanced reaction device (15) fully.Via pipeline (16) in the future the product fluid of self-equilibrating reactor (15) be circulated to the distillation stage (4) and made with extra care.This effluent liquid (13) comprises the methylhydrogenpolysi,oxane that contains trimethylsilyl end groups.
Usage quantity with methyl hydrogen siloxane before the enforcement balance is a benchmark, the inventive method third step inner equilibrium stop back gained reaction mixture comprise up to 60 weight %, preferred 15 to 25 weight %, density is lower than the water-insoluble organic solvents of 0.9kg/l and the more not volatile methyl hydrogen siloxane that is mainly straight chain type of 80 to 95 weight %.
The advantage of the inventive method is to implement simple and efficient height, because can avoid a large amount of relatively methylhydrogenpolysi,oxane described in EP-A967 236 to circulate via all procedure of processings, so productivity can significantly increase.
Another advantage of the inventive method that illustrates is: because of the ring-like compounds content height of volatility methylhydrogenpolysi,oxane product fluidic, the hydrochloric acid that is added to via pipeline (10) in the reactor had high reactivity, so in the straight chain type methylhydrogenpolysi,oxane, form cross-linking part easily, or formation microgel particle, thereby, can make the device parameter of program such as temperature of reactor and reactor pressure have the very large space that freely changes because this product fluidic omits.
The inventive method is particularly suitable for preparing the low volatility hydrogen methyl polysiloxane that contains trimethylsilyl end groups.
All the Reference numerals that adopt in Fig. 1 in following all embodiment.
Balance preferably analyzes by NMR and viscosity measurement is estimated.
Embodiment 1
Via pipeline (5) dimethyl dichlorosilane (DMCS) of 130kg/h and the trimethylchlorosilane of 7.0kg/h are added in the annular-pipe reactor (1), add via the distillate (comprising the lower molecular weight methyl hydrogen siloxane of 30 weight % and the toluene of 70 weight %) of pipeline (12), and add at 30 ℃ of hydrochloric acid via pipeline (10) self-separation device in future (3) with the thin-film evaporator (4) of 60l/h.Formed hydrogenchloride then reveals taking-up with the gaseous state autoreaction.From the partial hydrolysate of annular-pipe reactor (1), be that the 15g/kg homogeneous phase is sent into annular-pipe reactor (2) via pipeline (7) and mixed with the water of 21.5kg/h in this place as cl content.
To be added in the separator (3) from the reaction mixture of annular-pipe reactor (2) via pipeline (9).Implement centrifugation is divided into the bottom that organic hydrolysate on top reaches mutually corresponding to about 6 weight % concentration hydrochloric acid with this reaction mixture and contains water in this place.This bottom Xiang Shi is circulated to annular-pipe reactor (1) via pipeline (10).This organic hydrolysate in temperature up to 160 ℃ and under the situation of 1 millibar of absolute pressure, via interior two distillation stages of thin-film evaporator (4), logical heating and drying.The distillate fluid (14) that forms in the after-fractionating stage (4) is added in the balanced reaction device (15) fully, and the structure of this reactor is the bottom feed flowing bed reactor with sulphonated polystyrene resin catalyst bed.This balance is to implement under 20 ℃ of temperature and absolute pressure 1,100 hundred pascals' situation.
The viscosity of this distillate under 25 ℃ of temperature is 1.2 milli pascal seconds; Except that the toluene of 18 weight %, this distillate comprises the volatility methyl hydrogen siloxane of 82 weight %.
Total content with methyl hydrogen siloxane in the distillate is a benchmark, and under 20 ℃ of temperature of reaction, fixation pause stays the time and decides, and then forms the viscosity or the ratio of following DH chain or low volatility methylhydrogenpolysi,oxane.
Table 1:
| The residence time [minute] | ????D HChain [mole % silicon] | Viscosity (25 ℃, Hoeppler) [milli pascal second] |
| ????0 | ????- | ??1.2 |
| ????1.5 | ????87.8 | ??3.1 |
| ????2.5 | ????88.5 | ??3.5 |
| ????5 | ????90 | ??4.2 |
| ????10 | ????90.6 | ??4.8 |
Counter-balanced thin-film evaporator phlegma cycles back to the distillation fraction of factory (4).
Embodiment 2
Embodiment 1 is come again, and wherein different is: what be added to annular-pipe reactor (1) is 12.0kg/h but not the trimethylchlorosilane of 7.0kg/h, and that be added to annular-pipe reactor (2) is 22.4kg/h but not 21.5kg/h.The cl content that obtains 76.5kg/h is that 2mg/kg and viscosity are 15 square millimeters/second methylhydrogenpolysi,oxane.
Under 28 ℃ of temperature of reaction, fixation pause stays the time and decides, and then forms following main D
HThe viscosity of chain and ratio.
Table 2
| The residence time [minute] | ????D HChain [mole % silicon] | Viscosity (25 ℃, Hoeppler) [milli pascal second] |
| ????0 | ????- | ?0.98 |
| ????25 | ????92.0 | ?5.4 |
Claims (7)
1. method for preparing the methylhydrogenpolysi,oxane that contains trimethylsilyl end groups, wherein,
In first step, be lower than in density in the presence of the water-insoluble organic solvents of 0.9kg/l, with respect to every mole of hydrolyzable chlorine, dimethyl dichlorosilane (DMCS) and trimethylchlorosilane and 0.5 mole of water reaction at the most produce partial hydrolysate and gaseous hydrogen chloride,
In second step, for removing the SiCl group that still exists,, form hydrochloric acid with the described partial hydrolysate of water treatment, and
In third step, the volatile ring-like methyl hydrogen siloxane that obtains in first and/or second step is separated, and all or part of balance in addition, generate low-volatile, as to be mainly straight chain type methylhydrogenpolysi,oxane.
2. method as claimed in claim 1, wherein the hydrochloric acid that forms in second step is as the water source in the first step.
3. as the method for claim 1 or 2, wherein the weight ratio of dimethyl dichlorosilane (DMCS) and trimethylchlorosilane is 100: 1 to 2: 1.
4. as the method for one of claim 1-3, wherein said three steps are to implement fully continuously.
5. as the method for one of claim 1-4, wherein the cyclenes mixture of ready to balance comprises the toluene up to 60 weight %.
6. as the method for one of claim 1-5, wherein in third step, use equilibrium catalyst.
7. method as claimed in claim 6 wherein uses the strongly-acid ion-exchanger as equilibrium catalyst.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100489813A CN1331918C (en) | 2004-06-14 | 2004-06-14 | Preparation of methylhydropolysiloxane containing trimethylsilyl end group |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100489813A CN1331918C (en) | 2004-06-14 | 2004-06-14 | Preparation of methylhydropolysiloxane containing trimethylsilyl end group |
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| Publication Number | Publication Date |
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| CN1712429A true CN1712429A (en) | 2005-12-28 |
| CN1331918C CN1331918C (en) | 2007-08-15 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101568573B (en) * | 2007-01-31 | 2011-12-07 | 瓦克化学有限公司 | Process for preparing organopolysiloxanes |
| CN112961351A (en) * | 2020-12-07 | 2021-06-15 | 兰州康鹏威耳化工有限公司 | Continuous production process of dimethyl silicone oil |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2758124A (en) * | 1952-04-11 | 1956-08-07 | Gen Electric | Continuous hydrolysis of organohalogenosilanes |
| DE4328657A1 (en) * | 1993-08-26 | 1995-03-02 | Bayer Ag | Organopolysiloxane mixture for the production of adhesive-repellent organopolysiloxane films |
| DE19828390A1 (en) * | 1998-06-25 | 1999-12-30 | Wacker Chemie Gmbh | Process for the preparation of hydrogen methylpolysiloxanes with trimethylsilyl end groups |
-
2004
- 2004-06-14 CN CNB2004100489813A patent/CN1331918C/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101568573B (en) * | 2007-01-31 | 2011-12-07 | 瓦克化学有限公司 | Process for preparing organopolysiloxanes |
| CN112961351A (en) * | 2020-12-07 | 2021-06-15 | 兰州康鹏威耳化工有限公司 | Continuous production process of dimethyl silicone oil |
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| CN1331918C (en) | 2007-08-15 |
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