CN102898450B - Novel chlorine and bromine-containing bisilicate fire retardant compound and preparation method thereof - Google Patents
Novel chlorine and bromine-containing bisilicate fire retardant compound and preparation method thereof Download PDFInfo
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Abstract
The invention relates to a halogen-silicon synergistic flame retardant plasticizer tetrabromo bisphenol A bi(2-chloro-3-[tri(chloropropoxy)] silicon acyloxy propyl) ester compound and a preparation method thereof. The structural formula of the compound is shown in the description, wherein when n is equal to 1, m is equal to 0; when m is equal to 1, and n is equal to 0. The preparation method comprises the steps of performing reaction of tetrabromo bisphenol A biepoxypropyl ester and silicon tetrachloride in an organic solvent for 3-4 hours at 60-80 DEG C, reducing the temperature to 20 DEG C, adding chloroethanol drop by drop, heating the temperature to 45-55 DEG C, performing thermal insulation reaction for 3-4 hours, then purifying to obtain tetrabromo bisphenol A bi(2-chloro-3-[tri(chloro propoxy)] silicon acyloxy propyl) ester. The compound is the efficient flame retardant plasticizer and is suitable for flame retardant plasticizers of polyvinyl chloride, polyurethane, epoxy resin, unsaturated resin and the like.
Description
Technical field
The present invention relates to a kind of novel brominated pair of silicic ester flame-retardant immunomodulator compounds and preparation method thereof, be specifically related to two { the chloro-3-of 2-[three (chloroethoxy)] silicon acryloxypropylethoxysilane } ether compound of a kind of tetrabromo-bisphenol and preparation method thereof.This compound has bromine, chlorine, the synergistic flame-retardant plasticizer of silicon element, is applicable to the fire-retardant plasticizer additives such as polyvinyl chloride, urethane, epoxy resin, unsaturated polyester.
Background technology
Along with macromolecular material more and more answers land used popularity in fields such as building, chemical industry, military affairs and traffic, the flammable properties of its macromolecular material brings great threat often to the lives and properties of people, and thus flame-retarded technology receives global concern.The investigation and application of China's fire retardant after the eighties, particularly after entry to WTO with the integrating with of world economy, welcome the opportunity of high speed development, again due to the promulgation of European Union non-halogen (ROHS) instruction, while be also faced with stern challenge.China's fire retardant potential market is huge, and a few years from now on will with higher speed sustainable growth, and its development trend is then improving flame-retarded efficiency while, more focuses on the raising of environmental protection and ecological safety and comprehensive cost performance.
No matter there is larger gap with developed country in kind or on consumption in current China fire retardant, along with country is to the promulgation of flame retardant regulation and mandatory regulation, the development and application of China's fire retardant will occur wide prospect.The comprehensive cost performance wherein improving fire retardant by multielement synergy in the composite of fire retardant or molecular structure is one of emphasis direction of development research.
The novel brominated pair of silicic ester flame-retardant agent of the present invention is bromine, chlorine, the mutual synergy efficient flame-retarding agent of silicon element, due to molecular skeleton, there is linear ether-ether structure and material has good consistency, thus there is good plasticity, simultaneously, because the present invention selects the silicon tetrachloride as by-product of polysilicon industry to be raw material, again for a difficult problem for the comprehensive utilization solving silicon tetrachloride have found an effective way; The two silicon ester of this novel Halogen has that flame-retarded efficiency is high, plasticity good, applied range, technique simple, be easy to industrialization promotion produces, and will produce good economic benefit and environmental benefit.
Summary of the invention
An object of the present invention is two { the chloro-3-of 2-[three (chloroethoxy)] silicon acryloxypropylethoxysilane } ether of a kind of novel brominated pair of silicate ester flame-retardant plasticizer compound tetrabromo-bisphenol of silicon tetrachloride as by-product synthesis of proposition polysilicon industry, its fire-retardant plasticity is good, can overcome deficiency of the prior art.
For achieving the above object, present invention employs following technical scheme:
Two { the chloro-3-of 2-[three (the chloroethoxy)] silicon acryloxypropylethoxysilane } ether compound of a kind of tetrabromo-bisphenol, it is characterized in that, the structure of this compound is shown below:
Wherein during n=1, m=0; During m=1, n=0.
Another object of the present invention is to the preparation method proposing two { the chloro-3-of 2-[three (the chloroethoxy)] silicon acryloxypropylethoxysilane } ether of a kind of tetrabromo-bisphenol; its technique is simple, be easy to large-scale production, and cheaper starting materials is easy to get, and facility investment is few; with low cost, the method is:
At 20 DEG C, under agitation, control the mol ratio that raw material is suitable, the organic solvent solution of the tetrabromo-bisphenol diepoxypropyl ether of proper concn is added dropwise in silicon tetrachloride, drip process control temp not higher than 50 DEG C, after dropwising, be warmed up to 60-80 DEG C, insulation reaction 3-4h, cool to 20 DEG C, drip chloroethanol, drip process control and be no more than 35 DEG C, then intensification 45-55 DEG C, insulation reaction 2-3h, after hydrogen to be chlorinated discharges, reaction terminates, add the acid binding agent of quality product 1-3%, regulate pH=5-6, cross the trace solid salt filtering generation, filtrate goes out organic solvent and excessive chloroethanol (reclaim and use) and low boilers through underpressure distillation, obtain two { the chloro-3-of 2-[three (the chloroethoxy)] silicon acryloxypropylethoxysilane } ether of product tetrabromo-bisphenol.
The mol ratio controlling raw material suitable as above is tetrabromo-bisphenol diepoxypropyl ether: silicon tetrachloride: chloroethanol is 1: 2: 6-1: 2: 7.
The organic solvent solution of the tetrabromo-bisphenol diepoxypropyl ether of proper concn as above is the quality of tetrabromo-bisphenol diepoxypropyl ether and the volume ratio of organic solvent is 1: 2.5 ~ 1: 4.
Organic solvent as above is diethylene glycol dimethyl ether, toluene, ethylene dichloride, dioxane or acetonitrile.
Acid binding agent as above is triethylamine, DMA, pyridine or trimeric cyanamide.
Two { the chloro-3-of 2-[three (the chloroethoxy)] silicon acryloxypropylethoxysilane } ether of tetrabromo-bisphenol of the present invention is colourless or weak yellow liquid, productive rate is 96% ~ 99%, its flash-point (open cup): 210 ± 5 DEG C, decomposition temperature: 265 ± 5 DEG C, density: 1.573g/cm
3(25 DEG C), refractive index: n
d 25=1.4568.It is suitable as the use of the flame-retardant plasticizer of the materials such as polyvinyl chloride, polyvinyl alcohol, epoxy resin, unsaturated polyester, urethane.The synthesis technique principle of two { the chloro-3-of 2-[three (the chloroethoxy)] silicon acryloxypropylethoxysilane } ether of tetrabromo-bisphenol is shown below:
Wherein during n=1, m=0; During m=1, n=0.
Compared with prior art, beneficial effect of the present invention is:
1. because the structure of two { the chloro-3-of 2-[three (the chloroethoxy)] silicon acryloxypropylethoxysilane } ether of organosilicon halogen cooperative flame retardant softening agent tetrabromo-bisphenol of the present invention has good symmetric characteristics, its physical and chemical performance is stablized, good with macromolecular material intermiscibility, good processability, element cooperative flame retardant usefulness is high, and silicate structure plasticity is good.
2. the present invention with the silicon tetrachloride as by-product of polysilicon industry for two { the chloro-3-of 2-[three (the chloroethoxy)] silicon acryloxypropylethoxysilane } ether of Material synthesis silicon halogen cooperative flame retardant softening agent tetrabromo-bisphenol, a difficult problem for silicon tetrachloride comprehensive utilization can be solved, open again cheap excellent flame-retardant plasticizer new variety.
3. preparation method of the present invention is simple, and cheaper starting materials is easy to get, and cost is low, is easy to large-scale production.
Accompanying drawing explanation
In order to the stuctures and properties spy further illustrating product provides following accompanying drawing.
1, the infrared spectrogram of two { the chloro-3-of 2-[three (the chloroethoxy)] silicon acryloxypropylethoxysilane } ether of tetrabromo-bisphenol, refers to Figure of description Fig. 1;
Fig. 1 shows, 2964cm
-1, 2879cm
-1place is c h bond stretching vibration peak, 1653cm
-1place is phenyl ring skeleton stretching vibration peak, 1389cm
-1place is-CH
3flexural vibration peak, 1271cm
-1place is the stretching vibration peak of C-O key, 1117cm
-1place is the stretching vibration peak of Si-O key, 782cm
-1place is the stretching vibration peak of C-Cl key.
2, the nuclear magnetic spectrum figure of two { the chloro-3-of 2-[three (the chloroethoxy)] silicon acryloxypropylethoxysilane } ether of tetrabromo-bisphenol, refers to Figure of description Fig. 2;
Fig. 2 shows, deuterochloroform makes solvent, and δ 1.55-1.60 is-CH
3upper H peak; δ 3.38-3.41 is Ar-OCH
2cH (Cl) CH
2o-Si-upper chlorine substituted methylene H peak; δ 3.50-3.72 is-OCH
2cH
2cl upper chlorine substituted methylene H peak; δ 3.80-3.87 is Ar-OCH
2cH (CH
2cl) the upper methylene radical H peak be connected with chlorine of O-Si-; δ 3.90-3.96 is Ar-OCH
2cH (Cl) CH
2the methylene radical H peak that the upper and fragrant oxygen of O-Si-is connected; δ 4.04-4.21 is-OCH
2cH
2the upper methylene radical H peak be connected with oxygen of Cl; δ 4.23-4.32 is Ar-OCH
2cH (CH
2cl) the methylene radical H peak that is connected of the upper and fragrant oxygen of O-Si-; δ 4.58-4.72 is Ar-OCH
2cH (Cl) CH
2the upper methylene radical H peak be connected with silica of O-Si-; δ 4.90-5.01 is Ar-OCH
2cH (CH
2cl) the upper methyne H peak be connected with silica of O-Si-; δ 7.30-7.31 is the H peak on phenyl ring; δ 7.26-7.29 is the H peak of deuterochloroform solvent.
Embodiment
Below in conjunction with specific embodiment, technical scheme of the present invention is described further.
Embodiment 1 is under 20 DEG C of conditions, in the 100ml four-hole boiling flask that agitator, thermometer, high performance reflux condenser are housed, add 10ml toluene, add silicon tetrachloride 6.8g (4.54ml again, 0.04mol), the solution of 13.12g (0.02mol) tetrabromo-bisphenol diepoxypropyl ether will be dissolved with in 40ml toluene, be added dropwise in 40min in silicon tetrachloride, dropping process with ice-water bath control temperature not higher than 50 DEG C, after dropwising, 60 DEG C are warmed up to, insulation 3h in 30min; And then cool to 20 DEG C, drip chloroethanol 11.2g (0.12mol), with cooling bath with pass into speed control temperature of reaction not higher than 40 DEG C, after having led to, 55 DEG C are warming up in 1h, reaction 4h, after hydrogen to be chlorinated discharges, reaction terminates, cool to 35 DEG C and drip about 1ml triethylamine acid binding agent, regulate pH=5-6, cross the trace solid salt filtering generation, filtrate goes out organic solvent and low boilers through underpressure distillation, obtains two { the chloro-3-of 2-[three (the chloroethoxy)] silicon acryloxypropylethoxysilane } ether of product tetrabromo-bisphenol.Productive rate is 96%, its flash-point (open cup): 210 ± 5 DEG C, decomposition temperature: 265 ± 5 DEG C, density: 1.573g/cm
3(25 DEG C), refractive index: n
d 25=1.4568.
Embodiment 2 is under 20 DEG C of conditions, in the 100ml four-hole boiling flask that agitator, thermometer, high performance reflux condenser are housed, add 10ml ethylene dichloride, add silicon tetrachloride 6.8g (4.54ml again, 0.04mol), the solution of 13.12g (0.02mol) tetrabromo-bisphenol diepoxypropyl ether will be dissolved with in 40ml ethylene dichloride, be added dropwise in 40min in silicon tetrachloride, dropping process with ice-water bath control temperature not higher than 50 DEG C, after dropwising, 70 DEG C are warmed up to, insulation 4h in 30min; Cool to 20 DEG C, drip chloroethanol 12.1g (0.13mol), with cooling bath with pass into speed control temperature of reaction not higher than 40 DEG C, after having led to, 45 DEG C are warming up in 1h, reaction 3h, after hydrogen to be chlorinated discharges, reaction terminates, cool to 35 DEG C and drip about 1ml triethylamine acid binding agent, regulate pH=5-6, cross the trace solid salt filtering generation, filtrate goes out organic solvent and excessive ring chloroethanol (reclaim and use) and low boilers through underpressure distillation, obtains two { the chloro-3-of 2-[three (the chloroethoxy)] silicon acryloxypropylethoxysilane } ether of product tetrabromo-bisphenol.Productive rate is 98%, its flash-point (open cup): 210 ± 5 DEG C, decomposition temperature: 265 ± 5 DEG C, density: 1.573g/cm
3(25 DEG C), refractive index: n
d 25=1.4568.
Embodiment 3 is under 20 DEG C of conditions, in the 100ml four-hole boiling flask that agitator, thermometer, high performance reflux condenser are housed, add 10ml dioxane, add silicon tetrachloride 6.8g (4.54ml again, 0.04mol), the solution of 13.12g (0.02mol) tetrabromo-bisphenol diepoxypropyl ether will be dissolved with in 40ml dioxane, be added dropwise in 40min in silicon tetrachloride, dropping process with ice-water bath control temperature not higher than 50 DEG C, after dropwising, 80 DEG C are warmed up to, insulation 3h in 30min; Cool to 20 DEG C, drip chloroethanol 11.2g (0.12mol), temperature of reaction is controlled not higher than 40 DEG C with cooling bath and rate of addition, after having led to, 50 DEG C are warming up in 1h, reaction 3h, after hydrogen to be chlorinated discharges, reaction terminates, cool to 35 DEG C and drip about 1ml triethylamine acid binding agent, regulate pH=5-6, cross the trace solid salt filtering generation, filtrate goes out organic solvent and low boilers through underpressure distillation, obtains two { the chloro-3-of 2-[three (the chloroethoxy)] silicon acryloxypropylethoxysilane } ether of product tetrabromo-bisphenol.Productive rate is 97%, its flash-point (open cup): 210 ± 5 DEG C, decomposition temperature: 265 ± 5 DEG C, density: 1.573g/cm
3(25 DEG C), refractive index: n
d 25=1.4568.
Embodiment 4 is under 20 DEG C of conditions, in the 100ml four-hole boiling flask that agitator, thermometer, high performance reflux condenser are housed, add 10ml ethylene dichloride, add silicon tetrachloride 6.8g (4.54ml again, 0.04mol), the solution of 13.12g (0.02mol) tetrabromo-bisphenol diepoxypropyl ether will be dissolved with in 40ml ethylene dichloride, be added dropwise in 40min in silicon tetrachloride, dropping process with ice-water bath control temperature not higher than 50 DEG C, after dropwising, 70 DEG C are warmed up to, insulation 4h in 30min; Cool to 20 DEG C, drip chloroethanol 12.1g (0.13mol), temperature of reaction is controlled not higher than 40 DEG C with cooling bath and rate of addition, after having led to, 50 DEG C are warming up in 1h, reaction 3h, after hydrogen to be chlorinated discharges, reaction terminates, cool to 35 DEG C and drip about 1ml triethylamine acid binding agent, regulate pH=5-6, cross the trace solid salt filtering generation, filtrate goes out organic solvent and excessive ring chloroethanol (reclaim and use) and low boilers through underpressure distillation, obtains two { the chloro-3-of 2-[three (the chloroethoxy)] silicon acryloxypropylethoxysilane } ether of product tetrabromo-bisphenol.Productive rate is 99%, its flash-point (open cup): 210 ± 5 DEG C, decomposition temperature: 265 ± 5 DEG C, density: 1.573g/cm
3(25 DEG C), refractive index: n
d 25=1.4568.
Embodiment 5 is under 25 DEG C of conditions, in the 100ml four-hole boiling flask that agitator, thermometer, high performance reflux condenser are housed, add 10ml acetonitrile, add silicon tetrachloride 6.8g (4.54ml again, 0.04mol), the solution of 13.12g (0.02mol) tetrabromo-bisphenol diepoxypropyl ether will be dissolved with in 40ml acetonitrile, be added dropwise in 40min in silicon tetrachloride, dropping process with ice-water bath control temperature not higher than 50 DEG C, after dropwising, 80 DEG C are warmed up to, insulation 3h in 30min, cool to 20 DEG C, drip chloroethanol alkane 12.95g (0.14mol) 0.14mol, temperature of reaction is controlled not higher than 40 DEG C with cooling bath and rate of addition, after having led to, 45 DEG C are warming up in 1h, reaction 4h, after hydrogen to be chlorinated discharges, reaction terminates, cool to 35 DEG C and drip about 1ml triethylamine acid binding agent, regulate pH=5-6, cross the trace solid salt filtering generation, filtrate goes out organic solvent and excessive ring chloroethanol (reclaim and use) and low boilers through underpressure distillation, obtain two { the chloro-3-of 2-[three (the chloroethoxy)] silicon acryloxypropylethoxysilane } ether of product four tetrabromo-bisphenol.Productive rate is 97%, its flash-point (open cup): 210 ± 5 DEG C, decomposition temperature: 265 ± 5 DEG C, density: 1.573g/cm
3(25 DEG C), refractive index: n
d 25=1.4568.
Table 1 preparation example main technologic parameters
Two { the chloro-3-of 2-[three (the chloroethoxy)] silicon acryloxypropylethoxysilane } ether of collaborative for the silicon halogen of above-mentioned synthesis two silicon ester tetrabromo-bisphenol is also applied in polyvinyl chloride by inventor.The limiting oxygen index(LOI) of reference: GB/T2406-2008 " Plastics Combustion method for testing performance-oxygen index method " test sample product.Get after two { the chloro-3-of 2-[three (chloroethoxy)] silicon acryloxypropylethoxysilane } ether, plasticizer phthalic acid dioctyl ester, synergistic flame retardant antimonous oxide and the polyvinyl chloride of product silicon halogen cooperative flame retardant softening agent tetrabromo-bisphenol mix in varing proportions, extrude with forcing machine, make the batten that diameter is 3mm, and its flame retardant properties is tested, list part test result as shown in table 2:
The flame retardant properties data of two silicon ester worked in coordination with by table 2 silicon halogen
Claims (3)
1. the preparation method of a brominated pair of silicate ester flame-retardant plasticizer compound, it is characterized in that, the method is: at 20 DEG C, under agitation, control tetrabromo-bisphenol diepoxypropyl ether: silicon tetrachloride: the mol ratio of chloroethanol is 1: 2: 6-1: 2: 7, the solution being 1: 2.5-1: 4 by the quality grams of tetrabromo-bisphenol diepoxypropyl ether and the volume milliliter number ratio of organic solvent is added dropwise in silicon tetrachloride, drip process control temp not higher than 50 DEG C, after dropwising, be warmed up to 60-80 DEG C, insulation reaction 3-4h, cool to 20 DEG C, drip chloroethanol, drip process control and be no more than 35 DEG C, then intensification 45-55 DEG C, insulation reaction 2-3h, after hydrogen to be chlorinated discharges, reaction terminates, add the acid binding agent of quality product 1-3%, regulate pH=5-6, filter, filtrate goes out organic solvent and excessive chloroethanol and low boilers through underpressure distillation, obtain product brominated pair of silicate ester flame-retardant plasticizer, the structure of this compound is shown below:
Wherein during n=1, m=0; During m=1, n=0.
2. the preparation method of brominated pair of silicate ester flame-retardant plasticizer compound according to claim 1, is characterized in that: described organic solvent is diethylene glycol dimethyl ether, toluene, ethylene dichloride, dioxane or acetonitrile.
3. the preparation method of brominated pair of silicate ester flame-retardant plasticizer compound according to claim 1, is characterized in that: described acid binding agent is triethylamine, DMA, pyridine or trimeric cyanamide.
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| CN103554161B (en) * | 2013-11-08 | 2016-01-20 | 苏州科技学院相城研究院 | Fire retardant two [three (2,3-compound) silicon acyloxy] ethane compounds and preparation method thereof |
| CN103554156B (en) * | 2013-11-08 | 2015-12-30 | 苏州科技学院相城研究院 | Two silicic acid bromine propyl ester compound of fire retardant second dioxy support and preparation method thereof |
| CN103539809B (en) * | 2013-11-08 | 2016-04-27 | 苏州科技学院相城研究院 | Two silicic acid dichloro propyl ester compound of fire retardant second dioxy support and preparation method thereof |
| CN103554159B (en) * | 2013-11-08 | 2016-04-27 | 苏州科技学院相城研究院 | Two silicic acid dibromo propyl ester compound of fire retardant second dioxy support and preparation method thereof |
| CN103554163B (en) * | 2013-11-08 | 2015-12-02 | 苏州科技学院相城研究院 | Fire retardant two [three (chlorine propoxy-) silicon acyloxy] ethane compounds and preparation method thereof |
| CN103665016B (en) * | 2013-11-08 | 2016-02-24 | 苏州科技学院相城研究院 | Fire retardant two [three (3-bromine propoxy-) silicon acyloxy] ethane compounds and preparation method thereof |
| CN103554162B (en) * | 2013-11-08 | 2015-11-25 | 苏州科技学院相城研究院 | Fire retardant two [three (3-chlorine propoxy-) silicon acyloxy] ethane compounds and preparation method thereof |
| CN103554157B (en) * | 2013-11-08 | 2015-12-30 | 苏州科技学院相城研究院 | Flame retardant ethylenedioxy bromoethyl bisilicate compound and preparation method thereof |
| CN103554164B (en) * | 2013-11-08 | 2016-06-29 | 苏州科技学院相城研究院 | The preparation method of fire retardant two [three (chloroethoxy) silicon acyloxy] ethane |
| CN103554160B (en) * | 2013-11-08 | 2016-04-27 | 苏州科技学院相城研究院 | Fire retardant two [three (the chloro-2-propoxy-of 1,3-bis-) silicon acyloxy] ethane compounds and preparation method thereof |
| CN109651103B (en) * | 2017-10-10 | 2022-04-19 | 中国石油化工集团有限公司 | Method for purifying lauryl alcohol alkyl ether |
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