CN103087320A - Preparation method of hydroxyl-terminated polymethylphenyl silicone oil - Google Patents
Preparation method of hydroxyl-terminated polymethylphenyl silicone oil Download PDFInfo
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Abstract
The invention provides a preparation method of hydroxyl-terminated polymethylphenyl silicone oil. The preparation method comprises the following steps: firstly, preparing silane hydrolyzate containing phenyl link; acylating and subsequently hydrolyzing the silane hydrolyzate, acetic anhydride and an acid catalyst; taking the upper oil phase after the reaction is end; and purifying the oil phase to obtain the hydroxyl-terminated polymethylphenyl silicone oil. According to the preparation method of hydroxyl-terminated polymethylphenyl silicone oil, the problem of low content of the hydroxyl-terminated polymethylphenyl silicone oil in the prior art is solved; the hydroxyl-terminated polymethylphenyl silicone oil produced by the preparation method is low in viscosity, adjustable in hydroxyl and phenyl contents, wild in reaction conditions and not strict in requirements on devices and industrial production is easy to realize.
Description
Technical field
The present invention relates to chemical technology field, be specially a kind of preparation method of terminal hydroxy group polyphenylmethyl base silicone oil.
Background technology
As everyone knows, in the hot-vulcanized silicone rubber field, micromolecular hydroxyl silicone oil is the most frequently used silastic structure control agent.It can improve the dispersion of White Carbon black in rubber and the structurizing of inhibition sizing material in preparation glue stuff compounding process.But at some special dimensions, as the silica gel product that requires to produce need to have better high-low temperature resistant, and damping capacity and radiation resistance must add the silicone oil modification in addition that contains phenyl group in sizing material.Majority is the phenyl silicone oil of methyl blocking in the market, though it can improve the performances such as the high-low temperature resistant, radiation hardness of silica gel, due to the group of not being combined with rubber and White Carbon black, the silica gel product surface of therefore producing often has oil and analyses phenomenon and occur; Add Diphenylsilanediol also can reach effect preferably in rubber unvulcanizate, but because Diphenylsilanediol is solid, is difficult for being uniformly dispersed, thereby is prone to hickie in rubber unvulcanizate, be commonly called as and hang frost.If can introduce activity hydroxy on present phenyl silicone oil,, easy dispersion good due to its wetting property, with White Carbon black on silicon-hydroxy combining power strong, be conducive to prevent structurizing, that silica gel product oil of producing analyses problem, hang white phenomenon, structure problem all can be satisfactorily resolved.
The existing relevant report of at present hydroxy-end capped phenyl silicone oil.In the disclosed preparation method of Chinese patent CN102070785A take dichloromethyl phenylsilane hydrolyzate, Dimethyldichlorosilane hydrolysate and methyl phenyl ring siloxane as raw material, prepared hydroxy-end capped methylphenyl siloxane-dimethylsiloxane copolymer under base catalysis, this technique can only prepare the very low methyl phenyl silicone oil of hydroxy radical content.
Chinese patent CN101074283A discloses a kind of preparation method of hydroxyl-terminated polymethylphenyl sioxane, this method is take hydroxy-end capped polydimethylsiloxane, methyl phenyl ring siloxane as raw material, Tetramethylammonium hydroxide is catalyzer, prepares by polycondensation to get.This technique can only prepare the very low methyl phenyl silicone oil of hydroxy radical content equally.
Chinese patent CN102516546A discloses a kind of preparation method of low viscosity aminomethyl phenyl hydroxy silicon oil, and it drips dichloromethyl phenylsilane in weak base aqueous solution/organic solvent under-60 ~ 40 ℃ of conditions, reinforced be washed to neutral preparation again and get after complete.Silicon-hydroxyl that this technique generates when hydrolysis is very active, and hydroxyl value is subjected to the impact fluctuation of external condition very large, and is easy to cause the generation of cyclosiloxane.
Summary of the invention
The technical problem to be solved in the present invention is: overcome the low deficiency of the hydroxy radical content of methyl phenyl silicone oil in prior art, a kind of preparation method of terminal hydroxy group polyphenylmethyl base silicone oil is provided.
For solving the problems of the technologies described above the technical solution used in the present invention be:
A kind of preparation method of terminal hydroxy group polyphenylmethyl base silicone oil is: first preparation contains the silicane hydrolysate of phenyl chain link; being washed till neutrality with buck with aceticanhydride and an acidic catalyst after acidylate again is hydrolyzed again; get upper oil phase after having reacted, namely get small molecules terminal hydroxy group polyphenylmethyl base silicone oil after oil phase is purified.Its reaction equation is:
The described preparation method who contains the silicane hydrolysate of phenyl chain link is:
First drop into the mixing solutions of organic solvent/water in the reactor, under agitation drip dichloromethyl phenylsilane (or diphenyl dichlorosilane) and dimethyldichlorosilane(DMCS), after dropwising, oil reservoir is washed to neutrality with buck, standing demix after minute anhydrating mutually, removes organic solvent with organic phase under vacuum condition, obtain containing the silicane hydrolysate of phenyl chain link, this hydrolyzate is to contain the linearization of phenyl chain link and the mixture of ring body.Its reaction equation is:
In the preparation method of above-mentioned terminal hydroxy group polyphenylmethyl base silicone oil, described dichloromethyl phenylsilane or diphenyl dichlorosilane a kind of or both mixtures wherein, with the volume ratio of dimethyldichlorosilane(DMCS) be 1:4 ~ 4:1; Described organic solvent is one or more the mixture in toluene, dimethylbenzene, benzene, ethyl acetate, and organic solvent and dichlorosilane and water three's volume ratio is (1 ~ 2): 1:1; Described washing buck used is one or more the mixed aqueous solution in ammoniacal liquor, potassium hydroxide, sodium hydroxide, sodium carbonate, sodium bicarbonate; Washing temperature is 20 ~ 40 ℃; Removing the organic solvent temperature is 70 ~ 120 ℃.
In the preparation method of above-mentioned terminal hydroxy group polyphenylmethyl base silicone oil, each feed proportioning is counted by weight: contain 100 parts of the silicane hydrolysates of phenyl chain link, 20 ~ 40 parts of aceticanhydrides, 2 ~ 4 parts of an acidic catalysts.
In the preparation method of above-mentioned terminal hydroxy group polyphenylmethyl base silicone oil, selected an acidic catalyst is: the vitriol oil, acidic white earth, trifluoromethane sulfonic acid, a kind of in storng-acid cation exchange resin.
In the preparation method of above-mentioned terminal hydroxy group polyphenylmethyl base silicone oil, the acylation reaction temperature is 135 ~ 140 ℃, and the time is 5 ~ 6h; Hydrolysising reacting temperature is 65 ~ 70 ℃, and the time is 3 ~ 4h.
In the preparation method of above-mentioned terminal hydroxy group polyphenylmethyl base silicone oil, the oil reservoir purification process is that the calcium chloride drying dewaters, decolorizing with activated carbon.
The invention has the beneficial effects as follows: the terminal hydroxy group polyphenylmethyl base silicone oil that the present invention produces, have viscosity low, and hydroxy radical content and the adjustable advantage of phenyl content, and not harsh to equipment requirements, reaction conditions is gentle, easily realizes suitability for industrialized production.Existing technology is difficult to produce the terminal hydroxy group polyphenylmethyl base silicone oil of viscosity below 100cs, and hydroxyl value is generally below 2%.
Figure of description
Fig. 1 is the infrared spectrum of the terminal hydroxy group polyphenylmethyl base silicone oil of embodiment 1 preparation;
Fig. 2 is the infrared spectrum of the terminal hydroxy group polyphenylmethyl base silicone oil of embodiment 3 preparations.
Embodiment:
By following embodiment, the present invention is further described in detail.
Embodiment 1:
Under 20 ℃ of conditions, with dichloromethyl phenylsilane 60mL, dimethyldichlorosilane(DMCS) 140mL, be added drop-wise in 2h in the reactor of the mixing solutions that drops in advance 200mL toluene, 200mL water, after dropwising, oil reservoir is washed till neutrality with the 10%NaOH solution water, after standing branch vibration layer, oil reservoir is warming up to 90 ℃ of vacuum hydro-extraction desolventizings, and the molar content that obtains containing aminomethyl phenyl silica chain link is 24.3% hydrolyzate.Again by weight, with 100 parts of this hydrolyzates, 40 parts of aceticanhydrides, 2 parts of the vitriol oils, mix and be warming up to 140 ℃ of stirring 5h, lower the temperature standing, and 20% appropriate soda ash solution is washed to neutrality with it, then be warming up to 65 ℃ of stirring 4h, standing branch vibration layer, oil reservoir is dewatered with 2 parts of calcium chloride, then use 0.5 part of decolorizing with activated carbon, obtain water white small molecules terminal hydroxy group polyphenylmethyl base silicone oil.Its viscosity is 36cs, hydroxyl value 8.2%.
As seen from Figure 1,3417cm
-1The place is the absorption peak of silicon-hydroxyl, 2966cm
-1The place is the absorption peak of CH-CH in the silicon phenyl, 1617cm
-1Place and 1411cm
-1The place is the absorption peak of CH=CH in the silicon phenyl, 1255cm
-1Place and 801cm
-1The place is the absorption peak of silicon methyl, 1106cm
-1Place and 1019cm
-1The place is the absorption peak of silica silicon key, proves that prepared product is terminal hydroxy group polyphenylmethyl base silicone oil.
Embodiment 2:
Under 35 ℃ of conditions, with dichloromethyl phenylsilane 160mL, dimethyldichlorosilane(DMCS) 40mL, be added drop-wise in 2h in the reactor that drops in advance 400mL ethyl acetate, 200mL water mixed solution, after dropwising, oil reservoir is washed till neutrality with the 10%KOH solution water, after standing branch vibration layer, oil reservoir is warming up to 70 ℃ of vacuum hydro-extraction desolventizings, and the molar content that obtains containing aminomethyl phenyl silica chain link is 75.0% hydrolyzate.Again by weight, with 100 parts of this hydrolyzates, 35 parts of aceticanhydrides, 4 parts of acidic white earths, mix and be warming up to 135 ℃ of stirring 6h, lower the temperature standing, and 20% appropriate soda ash solution is washed to neutrality with it, then be warming up to 70 ℃ of stirring 3h, standing branch vibration layer, oil reservoir is dewatered with 2 parts of calcium chloride, then use 0.5 part of decolorizing with activated carbon, obtain water white small molecules terminal hydroxy group polyphenylmethyl base silicone oil.Its viscosity is 48cs, hydroxyl value 7.3%.
Embodiment 3:
Under 30 ℃ of conditions, with diphenyl dichlorosilane 40mL, dimethyldichlorosilane(DMCS) 160mL, be added drop-wise in 2h in the reactor of the mixing solutions that drops in advance 200mL benzene, 200mL water, after dropwising, oil reservoir is washed to neutrality with 10% ammonia soln, after standing branch vibration layer, oil reservoir is warming up to 80 ℃ of vacuum hydro-extraction desolventizings, the molar content that obtains containing phenylbenzene silica chain link is 12.7% hydrolyzate again.Again by weight, with 100 parts of this hydrolyzates, 30 parts of aceticanhydrides, 3 parts of storng-acid cation exchange resins, mix and be warming up to 135 ℃ of stirring 6h, lower the temperature standing, and 20% appropriate soda ash solution is washed to neutrality with it, then be warming up to 70 ℃ of stirring 3h, after standing branch vibration layer, oil reservoir is dewatered with 2 parts of calcium chloride, then use 0.5 part of decolorizing with activated carbon, obtain water white small molecules terminal hydroxy group polyphenylmethyl base silicone oil.Its viscosity is 53cs, hydroxyl value 6.5%.
As seen from Figure 2,3414cm
-1The place is the absorption peak of silicon-hydroxyl, 2963cm
-1The place is the absorption peak of CH-CH in the silicon phenyl, 1620cm
-1Place and 1408cm
-1The place is the absorption peak of CH=CH in the silicon phenyl, 1259cm
-1Place and 801cm
-1The place is the absorption peak of silicon methyl, 1084cm
-1Place and 1022cm
-1The place is the absorption peak of silica silicon key, proves that prepared product is terminal hydroxy group polyphenylmethyl base silicone oil.
Embodiment 4:
Under 25 ℃ of conditions, with diphenyl dichlorosilane 80mL, dimethyldichlorosilane(DMCS) 120mL, be added drop-wise in 2h in the reactor that drops in advance 300mL dimethylbenzene, 200mL water mixed solution, after dropwising, oil reservoir is washed to neutrality with 10% sodium carbonate solution, after standing branch vibration layer, oil reservoir is warming up to 120 ℃ of vacuum hydro-extraction desolventizings, and the molar content that obtains containing phenylbenzene silica chain link is 27.9% hydrolyzate.Again by weight, with 100 parts of this hydrolyzates, 25 parts of aceticanhydrides, 4 parts of acidic white earths, after mixing is warming up to 140 ℃ of stirring 5h, cooling is standing, and 20% appropriate soda ash solution is washed to neutrality with it, be warming up to 65 ℃ again and stir 4h, standing branch vibration layer dewaters oil reservoir with 2 parts of calcium chloride, use again 0.5 part of decolorizing with activated carbon, obtain water white small molecules terminal hydroxy group polyphenylmethyl base silicone oil.Its viscosity is 58cs, hydroxyl value 5.6%.
Embodiment 5:
Under 40 ℃ of conditions, with dichloromethyl phenylsilane 50mL, diphenyl dichlorosilane 50mL, dimethyldichlorosilane(DMCS) 100mL, be added drop-wise in 2h in the reactor that drops in advance 400mL toluene, 200mL water mixed solution, after dropwising, oil reservoir is washed to neutrality with 10% sodium hydrogen carbonate solution, after standing branch vibration layer, oil reservoir is warming up to 90 ℃ of vacuum hydro-extraction desolventizings, the molar content that obtains containing aminomethyl phenyl silica chain link is 22.5%, and the molar content of phenylbenzene silica chain link is 17.4% hydrolyzate.Again by weight, with 100 parts of this hydrolyzates, 20 parts of aceticanhydrides, 2 parts of trifluoromethane sulfonic acids, mix and be warming up to 135 ℃ of stirring 6h, lower the temperature standing, and 20% appropriate soda ash solution is washed to neutrality with it, then be warming up to 65 ℃ of stirring 4h, after standing branch vibration layer, oil reservoir is dewatered with 2 parts of calcium chloride, then use 0.5 part of decolorizing with activated carbon, obtain water white small molecules terminal hydroxy group polyphenylmethyl base silicone oil.Its viscosity is 61cs, hydroxyl value 4.5%.
The detection method of terminal hydroxy group polyphenylmethyl base silicone oil hydroxyl value content
(with reference to the Liyang hydroxy silicon oil company standard Q/320481JSK001-2011 of the scientific and technological Materials Co., Ltd of huge god)
Principle:
Hydroxyl and lithium aluminium hydride reaction releasing hydrogen gas, the volume by releasing hydrogen gas in the assaying reaction process can calculate hydroxy radical content.
Device:
Producer gas generator and gauge line;
Reagent:
Lithium aluminium hydride: analytical pure; Diethylene glycol dimethyl ether: analytical pure.
Operation steps:
1, add the 20mL diethylene glycol dimethyl ether in producer gas generator, then add 1.0～1.5g lithium aluminium hydride, start induction stirring, make it to react completely, adjust gauge line to zero-bit;
2, add the 0.1mL hydroxy silicon oil to producer gas generator, accurately weigh up example weight (claiming accurate to 0.0001g);
3, reaction is 2 minutes, reads the gauge line reading;
4, calculation formula is pressed following formula
In formula:
Barometric point (pa) when P--------measures
Gauge line reading (ml) after the V--------sample introduction
Gauge line reading (ml) before the V0-------sample introduction
V1-------sampling volume (ml)
Temperature during the T--------reaction (℃)
M--------sample heavy (g).
The method of calculation of terminal hydroxy group polyphenylmethyl base silicone oil phenyl content theoretical value
Volume according to input (phenyl methyl, phenylbenzene, dimethyl) dichlorosilane, in conjunction with proportion and molecular weight separately, can calculate molar content separately, the molar content of (phenyl methyl, phenylbenzene, dimethyl) the silica chain link after its hydrolysis is identical with it, and (phenyl methyl, phenylbenzene) silica chain link molar content separately is exactly the theoretical value of terminal hydroxy group polyphenylmethyl base silicone oil phenyl content divided by the per-cent of three's molar content summation of (phenyl methyl, phenylbenzene, dimethyl) silica chain link.
What more than enumerate is only specific examples of the present invention, and obviously the present invention does not limit above-mentioned example, also has many operative combination.Those skilled in the art can all should be considered as protection scope of the present invention from the situation that content disclosed by the invention directly derives or associates.
Claims (7)
1. the preparation method of a terminal hydroxy group polyphenylmethyl base silicone oil; it is characterized in that: first preparation contains the silicane hydrolysate of phenyl chain link; being washed till neutrality with buck with aceticanhydride and an acidic catalyst after acidylate again is hydrolyzed again; get upper oil phase after having reacted, namely get small molecules terminal hydroxy group polyphenylmethyl base silicone oil after oil phase is purified.
2. the preparation method of terminal hydroxy group polyphenylmethyl base silicone oil according to claim 1, it is characterized in that: the described preparation method who contains the silicane hydrolysate of phenyl chain link is:
First drop into the mixing solutions of organic solvent/water in the reactor, under agitation drip dichloromethyl phenylsilane or diphenyl dichlorosilane a kind of or both mixtures wherein, and dimethyldichlorosilane(DMCS), after dropwising, oil reservoir is washed to neutrality with buck, standing demix, after minute anhydrating mutually, organic phase is removed organic solvent under vacuum condition, obtain containing the silicane hydrolysate of phenyl chain link, this hydrolyzate is to contain the linearization of phenyl chain link and the mixture of ring body.
3. the preparation method of terminal hydroxy group polyphenylmethyl base silicone oil according to claim 2 is characterized in that: described dichloromethyl phenylsilane (or diphenyl dichlorosilane) is 1:4 ~ 4:1 with the volume ratio of dimethyldichlorosilane(DMCS); Described organic solvent is one or more the mixture in toluene, dimethylbenzene, benzene, ethyl acetate, and organic solvent and dichlorosilane and water three's volume ratio is (1 ~ 2): 1:1; Described washing buck used is one or more the mixed aqueous solution in ammoniacal liquor, potassium hydroxide, sodium hydroxide, sodium carbonate, sodium bicarbonate, and washing temperature is 20 ~ 40 ℃; Removing the organic solvent temperature is 70 ~ 120 ℃.
4. the preparation method of terminal hydroxy group polyphenylmethyl base silicone oil according to claim 1 is characterized in that: batching is counted by weight: contain 100 parts of the silicane hydrolysates of phenyl chain link, 20 ~ 40 parts of aceticanhydrides, 2 ~ 4 parts of an acidic catalysts.
5. the preparation method of terminal hydroxy group polyphenylmethyl base silicone oil according to claim 1, it is characterized in that: selected an acidic catalyst is: the vitriol oil, acidic white earth, trifluoromethane sulfonic acid, a kind of in storng-acid cation exchange resin.
6. the preparation method of terminal hydroxy group polyphenylmethyl base silicone oil according to claim 1, it is characterized in that: the acylation reaction temperature is 135 ~ 140 ℃, the time is 5 ~ 6h; Hydrolysising reacting temperature is 65 ~ 70 ℃, and the time is 3 ~ 4h.
7. the preparation method of terminal hydroxy group polyphenylmethyl base silicone oil according to claim 1, it is characterized in that: the oil reservoir purification process is that the calcium chloride drying dewaters, decolorizing with activated carbon.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103408759A (en) * | 2013-08-13 | 2013-11-27 | 江苏大学 | Preparation method of methyl phenyl silicone oil with high refractive index |
| CN105131295A (en) * | 2015-08-26 | 2015-12-09 | 广州市白云化工实业有限公司 | Phenyl hydroxyl silicone oil and preparation method and application thereof |
| CN105175729A (en) * | 2015-09-23 | 2015-12-23 | 浙江中天氟硅材料有限公司 | Method for preparing short-chain hydroxyl silicone oil |
| CN108341952A (en) * | 2018-02-27 | 2018-07-31 | 江西品汉新材料有限公司 | A kind of low temperature resistant lubricating oil of organosilicon and preparation method thereof |
| CN109942820A (en) * | 2019-03-26 | 2019-06-28 | 浙江置正有机硅有限公司 | A kind of preparation method of aminomethyl phenyl hydroxy silicon oil and oil water separator for the preparation of aminomethyl phenyl hydroxy silicon oil |
| CN110358089A (en) * | 2018-04-11 | 2019-10-22 | 苏州润特新材料科技有限公司 | A kind of preparation method of alkylaryl modified silicon oil |
| CN113087912A (en) * | 2021-03-01 | 2021-07-09 | 陈亚荣 | Processing technology of heat-resistant high-viscosity benzyl silicone oil |
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2013
- 2013-01-06 CN CN201310003581.XA patent/CN103087320B/en active Active
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| 李美江等: ""低粘度羟基封端聚甲基苯基硅氧烷的合成研究"", 《化工生产与技术》 * |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103408759A (en) * | 2013-08-13 | 2013-11-27 | 江苏大学 | Preparation method of methyl phenyl silicone oil with high refractive index |
| CN103408759B (en) * | 2013-08-13 | 2015-11-18 | 江苏大学 | A kind of preparation method of methyl phenyl silicone oil with high refractive index |
| CN105131295A (en) * | 2015-08-26 | 2015-12-09 | 广州市白云化工实业有限公司 | Phenyl hydroxyl silicone oil and preparation method and application thereof |
| CN105131295B (en) * | 2015-08-26 | 2018-02-13 | 广州市白云化工实业有限公司 | Phenyl hydroxy silicon oil and its preparation method and application |
| CN105175729A (en) * | 2015-09-23 | 2015-12-23 | 浙江中天氟硅材料有限公司 | Method for preparing short-chain hydroxyl silicone oil |
| CN105175729B (en) * | 2015-09-23 | 2018-01-12 | 浙江中天氟硅材料有限公司 | A kind of preparation method of short-chain hydroxyl silicone oil |
| CN108341952A (en) * | 2018-02-27 | 2018-07-31 | 江西品汉新材料有限公司 | A kind of low temperature resistant lubricating oil of organosilicon and preparation method thereof |
| CN108341952B (en) * | 2018-02-27 | 2021-03-02 | 江西品汉新材料有限公司 | Organic silicon low-temperature-resistant lubricating oil and preparation method thereof |
| CN110358089A (en) * | 2018-04-11 | 2019-10-22 | 苏州润特新材料科技有限公司 | A kind of preparation method of alkylaryl modified silicon oil |
| CN109942820A (en) * | 2019-03-26 | 2019-06-28 | 浙江置正有机硅有限公司 | A kind of preparation method of aminomethyl phenyl hydroxy silicon oil and oil water separator for the preparation of aminomethyl phenyl hydroxy silicon oil |
| CN113087912A (en) * | 2021-03-01 | 2021-07-09 | 陈亚荣 | Processing technology of heat-resistant high-viscosity benzyl silicone oil |
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