CN1569925A - Novel configuration phenyl methyl silicon oil - Google Patents
Novel configuration phenyl methyl silicon oil Download PDFInfo
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- CN1569925A CN1569925A CN 200410018067 CN200410018067A CN1569925A CN 1569925 A CN1569925 A CN 1569925A CN 200410018067 CN200410018067 CN 200410018067 CN 200410018067 A CN200410018067 A CN 200410018067A CN 1569925 A CN1569925 A CN 1569925A
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- silicone oil
- phenyl methyl
- methyl silicone
- polymerization degree
- siloxanes
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Abstract
The invention relates to a novel configuration phenyl methyl silicon oil which is synthesized from the following four raw materials, low polymerization degree oxosilane 28-35%, methylsiloxane 2-14%, low polymerization degree dimethyl diphenyl siloxane 50-70%, and tetramethyl 0.01-0.1% of the total weight of the three other constituents.
Description
[technical field]
The present invention relates to chemical technology field, a kind of specifically novel texture phenyl methyl silicone oil.
[technical background]
Phenyl methyl silicone oil is one of silicone oil principal item, its application surface is very extensive, it can be used in the thermal treatment of metal products and bathe, heat oil, aliphatic hydrocarbon, aromatic hydrocarbon, lipid acid, amine, alcohol, the separation of ester and alkene class, analyze and use chromosorb, the lubricating oil of electronic electric equipment, add carbon black lithium soap or molybdenumdisulphide as high temperature grease, can be used for the high temperature fan shaft bearing, spot contact bearing, the spot contact bearing cock of H level motor, delivery chain, the fire door wearing-proof bearing, wattmeter, motor car engine, the weaving drying machine, the bomb controller, steam turbines, the low speed wearing-proof bearing, high temperature resistant textile manufacturing machine lubricated etc. also can be used for chemical fibre spray silk release treatment etc.
Traditional polymethylphenyl siloxane fluid synthetic technology is to carry out cohydrolysis by trimethylchlorosilane and dimethyldichlorosilane(DMCS), phenmethyl dichlorosilane, and polyreaction (also can adopt hexamethyldisiloxane, methyl cyclosiloxane, phenylbenzene cyclosiloxane) is carried out polyreaction in the presence of catalyst acid or mineral alkali.The resulting phenyl methyl silicone oil of above-mentioned synthetic method is because the acid-basicity of remaining trace, can only there be dimethyl, phenmethyl or two kinds of siloxanes chain links of dimethyl diphenyl unit in the chain link simultaneously, thereby its flash-point (℃) generally can only be about 280～300 ℃, specific refractory power (25 ℃) is generally 1.460～1.495, (25 ℃/mm of viscosity
2S
-1) be generally 100～200, greater than 200, the remaining acid-basicity of silicone oil increases as if viscosity, and flash-point descends.Electronegativity and resistance to elevated temperatures are all not ideal enough, can't satisfy (25 ℃/mm of the demanding occasions 300 of some viscosity
2S
-1) more than, flash-point is greater than 300 ℃ with to the demanding occasion of fugitive constituent.
[summary of the invention]
Purpose of the present invention will overcome the deficiencies in the prior art exactly, and a kind of high viscosity (＞300/mm that has is provided
2S
-1), high flash point (〉=350 ℃), high refractive index (〉=1.4950/25 ℃), acid-basicity remaining in the silicone oil low (acid number≤0.01%), negative electricity effect and resistance to elevated temperatures are good and have a physiology inertia, being applicable to as life-time service under the hot conditions or nursing usefulness, is the synthetic method that has dimethyl, dimethyl diphenyl, three kinds of unitary novel phenyl methyl silicone oils of siloxanes chain link of aminomethyl phenyl on chain terminator (end-capping reagent) the Si-O-Si molecule long-chain simultaneously with the diphenylmethyl radical siloxane.
For achieving the above object, design a kind of novel texture phenyl methyl silicone oil, it is characterized in that: adopt following four kinds of raw materials to synthesize, its proportioning is:
With the diphenylmethyl radical siloxane is the low polymerization degree siloxanes 28～35% of end capping agent
Methyl cyclosiloxane silicone oil 2～14%
With hydroxy-end capped low polymerization degree dimethyl diphenyl siloxanes 50～70%
0.01～0.1% of the above-mentioned three kinds of component gross weights of Tetramethylammonium hydroxide
The present invention is that the polymerization degree of the low polymerization degree siloxanes of end capping agent is 0～8 with the diphenylmethyl radical siloxane; The methyl cyclosiloxane is a ring body, and its structure can be octamethylcyclotetrasiloxane D4, also can be the methyl mixed methylcyclosiloxane, as the mixture of D3, D4, D5, D6, be called for short DMC, but wherein the content of D4 must not be lower than 80%; Polymerization degree n=3～9 with hydroxy-end capped low polymerization degree dimethyl diphenyl siloxanes; Tetramethylammonium hydroxide can be the form adding with the aqueous solution or silicon alkoxide.
Synthesis technique of the present invention, it is characterized in that comprising following processing step: (1) is reinforced: taking by weighing respectively with the diphenyl-methyl siloxanes by prescription is the low polymerization degree siloxanes of end-capping reagent, feed composition I, the methyl cyclosiloxane, feed composition II, hydroxy-end capped low polymerization degree dimethyl diphenyl siloxanes, feed composition III, Tetramethylammonium hydroxide or Tetramethylammonium hydroxide silicon alkoxide, feed composition IV adds in the reactor of decompressions such as having stirring, thermometer, prolong susceptor; (2) heating, vacuum hydro-extraction: start stirring, nitrogen or air that feeding was handled through calcium chloride and silica dehydrator, start vacuum pump, regulate vacuum tightness, make its residual voltage be controlled at 40-10mmHg, start stirring, under agitation begin heating and carry out dehydration reaction, dehydration is 20-30 minute under 40-60 ℃/40-10mmHg; (3) heating and decompression: under agitation heat up, and reduce vacuum tightness; (4) base-catalysed rearrangement equilibration reaction: under 75-120 ℃/210-150mmHg condition, continue dehydration and alkali rearrangement reaction 1.5～3.0 hours, get rid of vacuum, recover normal pressure; (5) intensification, normal pressure destroy catalyzer: begin to heat up, destroy catalyzer in 170-200 ℃, kept 0.3～1.0 hour: (6) vacuum is taken off low boiling: vacuum pump reruns, under 300-350 ℃/10-5mmHg, take off low boiling 0.5～3.0 hour, unreacted low-boiling-point substance in the reaction of alkaline catalysts rearrangementization is removed; (7) activated carbon decolorizing filters: be cooled to 40 ℃ under vacuum condition, get rid of vacuum, obtain the transparent liquid phenyl methyl silicone oil of the little Huang of outward appearance after filtering with activated carbon decolorizing.
The present invention can exist dimethyl, dimethyl diphenyl, aminomethyl phenyl three kind siloxanes chain link unit simultaneously with the end-capping reagent of diphenylmethyl radical siloxane as chain in its Si-O-Si molecule long-chain, and the phenyl methyl silicone oil structural formula of this structure is as follows:
Wherein, m, n, o can regulate within the specific limits, and n also can be 0; Can obtain different viscosity by the materials that change and regulate four kinds of component raw material, different refractive index and the phenyl methyl silicone oil of being made up of different group dimethyl or phenylbenzene or phenmethyl can reach following fundamental property: outward appearance: little yellow transparent liquid
25 ℃ of viscosity: 〉=300/mm
2s
-1General 300-3000/mm
2s
-1
20 ℃ of refractive index: 1.4800～1.5100
Zero pour ℃ :≤-40 ℃
Flash-point ℃: 〉=350 ℃
Thermal losses 250 ℃/2 hours :≤0.8%
300 ℃/3 hours:＜1.5%
The present invention can anti-250～300 ℃ high temperature; Can be used for that high temperature occasion such as thermal barrier, textile manufacturing machine are lubricated, high temperature resistant silicone grease base oil, a chemical fibre spray silk release agent, also can be used for additive, the softening agent of 300 ℃ of long-time organic seal gums that use, and be used for the skin repair nursing of clinical burn, wound, scald and the nursing filling liquid of surgical patient prevention and treatment scar hyperplasia.
The present invention compare with prior art have high temperature resistant, low volatility, high flash point, characteristics such as low acid-basicity (neutrality), electronegative property and physiology inertia, cost is low, is worthy of promotion and application.
[description of drawings]
Fig. 1 is a process flow sheet of the present invention.
Referring to accompanying drawing 1,1 for getting material; 2 are heating, vacuum hydro-extraction; 3 are heating and decompression; 4 are base-catalysed rearrangement (equilibration); 5 are intensification, normal pressure destruction catalyzer; 6 take off low boiling for vacuum; 7 activated carbon decolorizings filter.
[specific embodiment]
Below in conjunction with accompanying drawing the present invention is done the detailed example explanation, the manufacturing technology of this Chemicals is still more clearly concerning this professional people.
Embodiment 1:
Taking by weighing respectively with the phenyl methyl is low polymerization degree siloxanes (component I) 192g (32%) of end-capping reagent, methyl cyclosiloxane (component I I) 81.6g (13.6%), with hydroxy-end capped low polymerization degree dimethyl diphenyl siloxanes 326.4g (54.4%), tetramethylammonium hydroxide aqueous solution 0.97g (weight of above-mentioned three kinds of components and 0.1%).The raw material of four kinds of components is added reaction flask, begin to stir, open vacuum pump, regulating vacuum pump maintains remaining pressure to begin under (40-10) mmHg to heat up, when temperature rises to 40 ℃, after dewatering 20 minutes under the 45 ℃/20mmHg condition, reduce vacuum tightness to residual voltage, about 200mmHg, begin to heat up, when temperature reaches 85 ℃, under 85 ℃/200mmHg condition, continue dehydration and begin to carry out the base-catalysed rearrangement reaction, 0.5 after hour, be warming up to 115 ℃, under 115 ℃/250mmHg, kept 2.0 hours, get rid of vacuum then, begin to heat up and destroy catalyzer, when temperature is elevated to 170 ℃, pick up counting, begin decompression after 0.5 hour and heat up, and after taking off low boiling 0.5 hour under the 330 ℃/10mmHg condition, begin cooling, cool to 40 ℃, get rid of vacuum, add activated carbon filtration, can obtain little yellow transparent liquid, viscosity (25 ℃): 330/mm
2s
-1,
Refractive index (20 ℃): 1.4930, flash-point (℃): 〉=350 ℃, phenyl methyl silicone oil 469g deviates to hang down the 84g that boils, productive rate about 80%.
Take by weighing respectively with the diphenylmethyl radical siloxane is low polymerization degree siloxanes (component I) 105g (35%) of end-capping reagent, methyl cyclosiloxane (component I I) 17.7g (5.9%), with hydroxy-end capped low polymerization degree dimethyl diphenyl siloxanes (component III) 177.3g (59.1%), the raw material of four kinds of components such as tetramethylammonium hydroxide aqueous solution 0.67g (above-mentioned three kinds of composition weight and 0.08%) adds, by carrying out synthetic operation, obtain viscosity (25 ℃): 720/mm with embodiment 1 identical processing condition
2s
-1, refractive index (20 ℃): 1.5185, flash-point (℃): 〉=350 ℃, outward appearance is the phenyl methyl silicone oil 229g of little yellow transparent liquid, removes the low 37g that boils, productive rate about 77%.
Take by weighing respectively with the diphenylmethyl radical siloxane is low polymerization degree siloxanes (component worker) 180g (29.3%) of end-capping reagent, methyl cyclosiloxane (component I I) 15g (2.4%), with hydroxy-end capped low polymerization degree dimethyl diphenyl siloxanes (component I I) 420g (68.3%), the raw material of four kinds of components such as tetramethylammonium hydroxide aqueous solution 0.97g (above-mentioned three kinds of composition weight and 0.06%) adds, by carrying out synthetic operation, obtain viscosity (25 ℃): 1300/mm with embodiment 1 identical processing condition
2s
-1, refractive index (20 ℃): 1.5270, flash-point (℃): 〉=360 ℃, zero pour＜-40 ℃, outward appearance is the phenyl methyl silicone oil 460g of little yellow transparent liquid, removes the low 84g that boils, productive rate about 77%.
Claims (11)
1, a kind of novel texture phenyl methyl silicone oil is characterized in that: adopt following four kinds of raw materials to synthesize, its proportioning is:
With the diphenylmethyl radical siloxane is the low polymerization degree siloxanes 28～35% of end capping agent
Methyl cyclosiloxane silicone oil 2～14%
With hydroxy-end capped low polymerization degree dimethyl diphenyl siloxanes 50～70%
0.01～0.1% of the above-mentioned three kinds of component gross weights of Tetramethylammonium hydroxide
2, according to claims 1 described a kind of novel texture phenyl methyl silicone oil, it is characterized in that: with the diphenylmethyl radical siloxane is that the polymerization degree of the low polymerization degree siloxanes of end capping agent is 0～8.
3, according to claims 1 described a kind of novel texture phenyl methyl silicone oil, it is characterized in that: the methyl cyclosiloxane is a ring body, its structure can be octamethylcyclotetrasiloxane D4, it also can be the methyl mixed methylcyclosiloxane, mixture as D3, D4, D5, D6, be called for short DMC, but wherein the content of D4 must not be lower than 80%.
4, according to claims 1 described a kind of novel texture phenyl methyl silicone oil, it is characterized in that: with polymerization degree n=3～9 of hydroxy-end capped low polymerization degree dimethyl diphenyl siloxanes.
5, according to claims 1 described a kind of novel texture phenyl methyl silicone oil, it is characterized in that: Tetramethylammonium hydroxide can be the form adding with the aqueous solution or silicon alkoxide.
6, according to the synthesis technique of claims 1 described a kind of novel texture phenyl methyl silicone oil, it is characterized in that comprising following processing step: (1) is reinforced: taking by weighing respectively with the diphenyl-methyl siloxanes by prescription is the low polymerization degree siloxanes of end-capping reagent, feed composition I, the methyl cyclosiloxane, feed composition II, hydroxy-end capped low polymerization degree dimethyl diphenyl siloxanes, feed composition III, Tetramethylammonium hydroxide or Tetramethylammonium hydroxide silicon alkoxide, feed composition IV adds in the reactor of decompressions such as having stirring, thermometer, prolong susceptor; (2) heating, vacuum hydro-extraction: start stirring, nitrogen or air that feeding was handled through calcium chloride and silica dehydrator, start vacuum pump, regulate vacuum tightness, make its residual voltage be controlled at 40-10mmHg, start stirring, under agitation begin heating and carry out dehydration reaction, dehydration is 20-30 minute under 40-60 ℃/40-10mmHg; (3) heating and decompression: under agitation heat up, and reduce vacuum tightness; (4) base-catalysed rearrangement equilibration reaction: under 75-120 ℃/210-150mmHg condition, continue dehydration and alkali rearrangement reaction 1.5～3.0 hours, get rid of vacuum, recover normal pressure; (5) intensification, normal pressure destroy catalyzer: begin to heat up, in 170-200 ℃ of destruction catalyzer, kept 0.3～1.0 hour; (6) vacuum is taken off low boiling: the vacuum pump that reruns, under 300-350 ℃/10-5mmHg, take off low boiling 0.5～3.0 hour, and unreacted low-boiling-point substance in the reaction of alkaline catalysts rearrangementization is removed; (7) activated carbon decolorizing filters: be cooled to 40 ℃ under vacuum condition, get rid of vacuum, obtain the transparent liquid phenyl methyl silicone oil of the little Huang of outward appearance after filtering with activated carbon decolorizing.
7, according to claims 1 described a kind of novel texture phenyl methyl silicone oil, it is characterized in that: with the end-capping reagent of diphenylmethyl radical siloxane as chain, simultaneously can have dimethyl, dimethyl diphenyl, three kinds of siloxanes chain links of aminomethyl phenyl unit in its Si-O-Si molecule long-chain, the phenyl methyl silicone oil structural formula of this structure is as follows:
Wherein, m, n, o can regulate within the specific limits, and n also can be 0.
8, according to claims 1 described a kind of novel texture phenyl methyl silicone oil, it is characterized in that: can obtain different viscosity by the materials that change and regulate four kinds of component raw material, different refractive index and the phenyl methyl silicone oil of being made up of different group dimethyl or phenylbenzene or phenmethyl can reach following fundamental property:
Outward appearance: little yellow transparent liquid
25 ℃ of viscosity: 〉=300/mm
2s
-1General 300-3000/mm
2s
-1
20 ℃ of refractive index: 1.4800～1.5100
Zero pour ℃ :≤-40 ℃
Flash-point ℃: 〉=350 ℃
Thermal losses 250 ℃/2 hours :≤0.8%
300 ℃/3 hours:＜1.5%
9, according to claims 1 described a kind of novel texture phenyl methyl silicone oil, its feature is stored in: it can anti-250～300 ℃ high temperature.
10, according to claims 1 described a kind of novel texture phenyl methyl silicone oil, it is characterized in that: can be used for that high temperature occasion such as thermal barrier, textile manufacturing machine are lubricated, high temperature resistant silicone grease base oil, a chemical fibre spray silk release agent, also can be used for additive, the softening agent of 300 ℃ of long-time organic seal gums that use, and be used for the skin repair nursing of clinical burn, wound, scald and the nursing filling liquid of surgical patient prevention and treatment scar hyperplasia.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410018067 CN1569925A (en) | 2004-04-29 | 2004-04-29 | Novel configuration phenyl methyl silicon oil |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410018067 CN1569925A (en) | 2004-04-29 | 2004-04-29 | Novel configuration phenyl methyl silicon oil |
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| Publication Number | Publication Date |
|---|---|
| CN1569925A true CN1569925A (en) | 2005-01-26 |
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ID=34479334
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|---|---|---|---|
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Cited By (13)
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|---|---|---|---|---|
| CN100334133C (en) * | 2005-03-07 | 2007-08-29 | 华明扬 | Process for preparing cation composite modified organic silicon emulsion with softening, slipping and elastic function |
| CN100334137C (en) * | 2005-03-07 | 2007-08-29 | 华明扬 | Process for preparing anion composite modified organic silicon emulsion with softening and anti-shrinking function |
| CN100334132C (en) * | 2005-03-07 | 2007-08-29 | 华明扬 | Process for preparing anion composite modified organic silicon emulsion with relaxing and anti-shrinking function |
| CN100334136C (en) * | 2005-03-07 | 2007-08-29 | 华明扬 | Process for preparing anion composite modified organic silicon emulsion with softening, slipping and elastic function |
| CN100389144C (en) * | 2005-03-07 | 2008-05-21 | 华明扬 | Process for preparing cation composite modified organic silicon emulsion with softening and anti-shrinking function |
| CN100389143C (en) * | 2005-03-07 | 2008-05-21 | 华明扬 | Process for preparing anion composite modified organic silicon emulsion with softening, anti-shrinking and elastic function |
| CN100396715C (en) * | 2006-04-17 | 2008-06-25 | 广州天赐有机硅科技有限公司 | Branched benzene siliconic oil |
| CN101851334A (en) * | 2010-04-19 | 2010-10-06 | 上海爱世博有机硅材料有限公司 | Dimethyl diphenyl room-temperature vulcanized silicone rubber as well as production process and application thereof |
| CN101565506B (en) * | 2009-05-25 | 2012-08-29 | 威海华康生物芯片有限公司 | Method for preparing medical high-activity silicon oil |
| CN103435806A (en) * | 2013-07-17 | 2013-12-11 | 烟台德邦先进硅材料有限公司 | Branched chain type phenyl silicone oil and preparation methods thereof |
| CN103588972A (en) * | 2012-08-18 | 2014-02-19 | 邵成芬 | Phenyl vinyl silicone oil with high refractive index and high light transmittance and preparation method thereof |
| CN105199109A (en) * | 2015-09-29 | 2015-12-30 | 广州有色金属研究院 | Preparation method of MDT-type phenyl methyl silicone oil for cosmetics |
| CN112852163A (en) * | 2019-11-12 | 2021-05-28 | 中国科学院化学研究所 | Crystalline nanoparticle, photocurable organic silicon resin and nanoparticle composition, preparation method and application |
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2004
- 2004-04-29 CN CN 200410018067 patent/CN1569925A/en active Pending
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100334133C (en) * | 2005-03-07 | 2007-08-29 | 华明扬 | Process for preparing cation composite modified organic silicon emulsion with softening, slipping and elastic function |
| CN100334137C (en) * | 2005-03-07 | 2007-08-29 | 华明扬 | Process for preparing anion composite modified organic silicon emulsion with softening and anti-shrinking function |
| CN100334132C (en) * | 2005-03-07 | 2007-08-29 | 华明扬 | Process for preparing anion composite modified organic silicon emulsion with relaxing and anti-shrinking function |
| CN100334136C (en) * | 2005-03-07 | 2007-08-29 | 华明扬 | Process for preparing anion composite modified organic silicon emulsion with softening, slipping and elastic function |
| CN100389144C (en) * | 2005-03-07 | 2008-05-21 | 华明扬 | Process for preparing cation composite modified organic silicon emulsion with softening and anti-shrinking function |
| CN100389143C (en) * | 2005-03-07 | 2008-05-21 | 华明扬 | Process for preparing anion composite modified organic silicon emulsion with softening, anti-shrinking and elastic function |
| CN100396715C (en) * | 2006-04-17 | 2008-06-25 | 广州天赐有机硅科技有限公司 | Branched benzene siliconic oil |
| CN101565506B (en) * | 2009-05-25 | 2012-08-29 | 威海华康生物芯片有限公司 | Method for preparing medical high-activity silicon oil |
| CN101851334A (en) * | 2010-04-19 | 2010-10-06 | 上海爱世博有机硅材料有限公司 | Dimethyl diphenyl room-temperature vulcanized silicone rubber as well as production process and application thereof |
| CN103588972A (en) * | 2012-08-18 | 2014-02-19 | 邵成芬 | Phenyl vinyl silicone oil with high refractive index and high light transmittance and preparation method thereof |
| CN103435806A (en) * | 2013-07-17 | 2013-12-11 | 烟台德邦先进硅材料有限公司 | Branched chain type phenyl silicone oil and preparation methods thereof |
| CN103435806B (en) * | 2013-07-17 | 2015-09-02 | 烟台德邦先进硅材料有限公司 | A kind of branched chain type phenyl silicone oil and preparation method thereof |
| CN105199109A (en) * | 2015-09-29 | 2015-12-30 | 广州有色金属研究院 | Preparation method of MDT-type phenyl methyl silicone oil for cosmetics |
| CN105199109B (en) * | 2015-09-29 | 2017-10-10 | 广州有色金属研究院 | A kind of preparation method of MDT types polymethylphenyl siloxane fluid used for cosmetic |
| CN112852163A (en) * | 2019-11-12 | 2021-05-28 | 中国科学院化学研究所 | Crystalline nanoparticle, photocurable organic silicon resin and nanoparticle composition, preparation method and application |
| CN112852163B (en) * | 2019-11-12 | 2022-05-03 | 中国科学院化学研究所 | Crystalline nanoparticle, photocurable organic silicon resin and nanoparticle composition, preparation method and application |
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