CN102731545A - Isocyanurate chloropropyl chloroethyl silicate and preparation method thereof - Google Patents

Isocyanurate chloropropyl chloroethyl silicate and preparation method thereof Download PDF

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CN102731545A
CN102731545A CN2012102472563A CN201210247256A CN102731545A CN 102731545 A CN102731545 A CN 102731545A CN 2012102472563 A CN2012102472563 A CN 2012102472563A CN 201210247256 A CN201210247256 A CN 201210247256A CN 102731545 A CN102731545 A CN 102731545A
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silicon
chloroethoxy
chloro
propyl group
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CN102731545B (en
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王彦林
楼晓莉
李豫丹
吴娟
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Suzhou University of Science and Technology
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Abstract

The invention relates to a nitrogen, silicon and chlorine thee-element synergic flame retardant tri{2-chloro-3-[tri(chloroethoxy)silicon acyloxy]propyl}isocyanurate compound and a preparation method thereof. The structure of the compound is shown as a formula in the specification. The preparation method comprises the following steps: dripping organic solvent solution of triglycidyl Isocyanurate into silicon tetrachloride, and reacting for 4 to 6 hours at a temperature of between 50 and 70 DEG C; and cooling to 30 DEG C, introducing ethylene oxide under the liquid surface, reacting for 2 to 3 hours at a temperature of between 45 and 55 DEG C, and purifying to obtain the tri{2-chlor-3-[tri(chloroethoxy)silicon acyloxy]propyl}isocyanurate. The compound has good flame retardant plasticization, and is suitable for flame retardant plasticizer such as polyvinyl chloride, polyurethane, epoxy resin, unsaturated resin and the like; and the method has simple production process and low cost, and is easy for industrial production.

Description

Tricarbimide chlorine propoxy-tetra-(chloroethyl) silicate compound and preparation method thereof
Technical field
The present invention relates to a kind of nitrogen, silicon, chlorine element synergistic fire retardant tricarbimide chlorine propoxy-tetra-(chloroethyl) silicate compound and preparation method thereof; Be specifically related to a kind of three { 2-chloro-3-[three (chloroethoxy) silicon acyloxy] propyl group } tricarbimide ester cpds and preparation method thereof, this compound is suitable for the flame-retardant plasticizer of SE, urethane, epoxy resin, unsaturated polyester etc.
Background technology
Along with the raising of development and national economy and living standards of the people, macromolecular materials such as synthon, plastics, rubber more and more widely be applied to every field such as communications and transportation, material of construction, electronic apparatus, household furniture, interior decoration.But these macromolecular materials generally all have inflammableness, and easy initiation fire accident for the anti-combustion that solves synthetic materials, press down problem such as cigarette, is guaranteed the security that synthetic materials uses, and effective means is to add fire retardant.Because the halogenated flame retardant addition is few, cheap and good with the synthetic materials consistency, does not change fire retardant goods original mechanical processing characteristics, thereby be current production rate and the maximum organic fire-retardant of usage quantity.But, halogenated flame retardant is restricted because it can decompose problems such as producing hydrogen halide when burning.Along with strengthening day by day of fire-retardant awareness of the importance of fire prevention in the world wide and being gradually improved of fire-retardant rules, promoted the research and development of environment friendly flame retardant to use, especially novel, efficient, low toxicity type fire retardant faces more urgent demand.The addition of developing efficient halogenated flame retardant minimizing fire retardant simultaneously is the important directions of research with the influence that reaches the amount that reduces the hydrogen halide of being emitted when burning and reduce the material mechanical processing characteristics.The excellent properties that press down cigarette owing to the silicon-type flame-retardant plasticizer has, promotes into carbon obtains people's attention.But silicon-type product price general charged is expensive, use range is narrow, and use is restricted.
The silicon tetrachloride as by-product that the invention discloses with the polysilicon industry is main raw material synthetic nitrogen, silicon, chlorine element cooperative flame retardant immunomodulator compounds and preparation method thereof; The present invention has combined nitrogen flame retardant expandable flame retardant; Silicon-series five-retardant can generate fine and close silicon carbon layer; The meteorological fire-retardant mechanism of halogenated flame retardant; Developed nitrogen, silicon, the chlorine element synergistic fire retardant tricarbimide chlorine propoxy-tetra-(chloroethyl) silicate compound of Cheap highly effective, the research of this product has successfully been opened up an effective way to the comprehensive utilization of contaminated solution thing silicon tetrachloride, has increased a new and effective fire retardant kind again for market; To promoting the fast development of China's Fire Retardant Industry, ensure that the safety of people's lives and properties all has an important significance.
Summary of the invention
One of the object of the invention is to propose a kind of silicon tetrachloride as by-product synthetic nitrogen with the polysilicon industry, silicon, chlorine cooperative flame retardant softening agent three { 2-chloro-3-[three (chlorine propoxy-) silicon acyloxy] propyl group } tricarbimide ester cpds; Its flame-retarded efficiency is high, can overcome deficiency of the prior art.
For realizing the foregoing invention purpose, the present invention has adopted following technical scheme:
Three { 2-chloro-3-[three (chloroethoxy) silicon acyloxy] propyl group } tricarbimide ester cpds is characterized in that the structure of this compound is shown below:
Figure BSA00000750148300021
Another object of the present invention is to propose the compound method of a kind of three { 2-chloro-3-[three (chloroethoxy) silicon acyloxy] propyl group } tricarbimide ester cpds; Its technology is simple, be easy to large-scale production, and low in raw material cost is easy to get, and facility investment is few; With low cost, this method is:
Under 20 ℃ of conditions, the organic solvent solution of certain density isocyanuric acid three-glycidyl ester is added drop-wise in the silicon tetrachloride of 3 times of moles, then be warming up to 50 ℃～70 ℃ sustained reaction 4～6h; Cool to 30 ℃ again; Liquid level feeds the oxyethane of certain mol proportion down; Then be warming up to 45 ℃～55 ℃ sustained reaction 2～3h; When reaction solution PH=5-6, excessive oxyethane and organic solvent and a spot of low boilers are removed in distillation, get three { 2-chloro-3-[three (chloroethoxy) silicon acyloxy] propyl group } chlorinated isocyanurates.
Finite concentration is that the quality of isocyanuric acid three-glycidyl ester is 1 with the volume of organic solvent ratio as stated: 5-1: 15.
The oxyethane of certain mol proportion is isocyanuric acid three-glycidyl ester as stated: silicon tetrachloride: the oxyethane mol ratio is 1: 3: 9-1: 3: 12.
Aforesaid organic solvent is for being dioxane, THF, acetonitrile or ethylene dichloride.
Tricarbimide chlorine propoxy-silicic acid chloroethene ester of the present invention is colourless or light yellow liquid, and the product yield is 94.6%～97.3%, flash-point (open cup): 214 ± 5 ℃, and decomposition temperature: (278 ± 5) ℃, refractive index: n D 20=1.6648, density (25 ℃): 1.383g/cm 3, it is suitable as the fire-retardant usefulness of materials such as SE, urethane, epoxy resin, unsaturated polyester, and the synthesis technique principle of this tricarbimide chlorine propoxy-silicic acid chloroethene ester is shown below:
Figure BSA00000750148300031
Compared with prior art, beneficial effect of the present invention is:
1. because tricarbimide chlorine propoxy-silicic acid chloroethene ester of the present invention is nitrogen, silicon, the agent of chlorine element collaborative type flame-retardant, cooperative flame retardant usefulness is high, and structural symmetry is good; Product is stable; Decomposition temperature is high, and has the intermiscibility of polyester structure and macromolecular material good, and plasticity is good.
The silicon tetrachloride problem of complex utilization that the solution polysilicon industry that is developed as of tricarbimide chlorine propoxy-tetra-(chloroethyl) silicate compound 2. of the present invention is given off has searched out effective ways; And building-up process atom utilization 100%; More help environmental protection; Have good benefits in environment, have good economic benefits again.
The synthesis technique equipment of tricarbimide chlorine propoxy-silicic acid chloroethene ester 3. of the present invention is simple and easy to control, with low cost, is suitable for most chemical enterprise and carries out large-scale production.
Description of drawings
For structure and the performance spy who further specifies product provides following accompanying drawing.
1, the infrared spectrogram of three { 2-chloro-3-[three (chloroethoxy) silicon acyloxy] propyl group } chlorinated isocyanurates sees Figure of description Fig. 1 for details;
Fig. 1 shows, at 2964cm -1-2884cm -1The place is c h bond stretching vibration peak, 2820-2780cm -1The place is the stretching vibration peak of C-N key, 1690-1700cm -1The place is the stretching vibration peak of ketonic linkage, 1464cm -1The place is-CH 2-the flexural vibration peak, 1264cm -1The place is the stretching vibration peak of C-O key, 1114cm -1The place is the stretching vibration peak of Si-O key, 762cm -1The place is the stretching vibration peak of C-Cl key.
2, the nuclear magnetic spectrum figure of three { 2-chloro-3-[three (chloroethoxy) silicon acyloxy] propyl group } chlorinated isocyanurates sees Figure of description Fig. 2 for details;
Fig. 2 shows that deuterochloroform is made solvent, and δ 3.58-3.65 place is-NCH 2CH (Cl) CH 2The last methylene radical 2H peak that links to each other with oxygen of O-; δ 3.66-3.70 is-OCH 2CH 2The last methylene radical 6H peak that links to each other with oxygen of Cl; δ 3.90-4.10 is-OCH 2CH 2The last methylene radical 6H peak that links to each other with chlorine of Cl; δ 4.15-4.32 place is-NCH 2CH (Cl) CH 2The last methylene radical 2H peak that links to each other with nitrogen of O-; δ 4.47-4.63 is-NCH 2CH (Cl) CH 2The last chlorine substituted methylene of O-1H peak; δ 7.29-7.30 place is the H peak of deuterochloroform solvent.
Specific embodiment
Below in conjunction with embodiment technical scheme of the present invention is further specified.
Embodiment 1 adds the 10ml acetonitrile in the 100ml there-necked flask that whisking appliance, TM and efficient reflux condensing tube are housed, catch up with the air in the most bottle with nitrogen, accurately draws 3.40ml (0.03mol) SiCl 4Place there-necked flask.Take by weighing 3.00g (0.01mol) isocyanuric acid three-glycidyl ester and be dissolved in the 40ml acetonitrile, with being added drop-wise in the there-necked flask in the about 0.5h of this solution, be warming up to 50 ℃ of insulation reaction 6h after dropwising under 20 ℃; Be cooled to 30 ℃ again, at the efficient reflux condensing tube expansion soft seal cover that extremely to stretch, feeding 3.96g (0.09mol) oxyethane under the liquid level adorned suitable for reading; Feed process control temp and be not higher than 40 ℃, then be warming up to 55 ℃ of insulation reaction 3h, check reaction solution pH is a terminal point at 5-6; After reaction finishes; Underpressure distillation goes out solvent and low boilers gets product three { 2-chloro-3-[three (chlorine propoxy-) silicon acyloxy] propyl group } chlorinated isocyanurates, and productive rate is 94.6%, flash-point (open cup): 214 ± 5 ℃; Decomposition temperature: 278 ± 5 ℃, refractive index: n D 20=1.6648, density (25 ℃): 1.383g/cm 3
Embodiment 2 adds the 10ml THF in the 100ml there-necked flask that whisking appliance, TM and efficient reflux condensing tube are housed, catch up with the air in the most bottle with nitrogen, accurately draws 3.40ml (0.03mol) SiCl 4Place there-necked flask.Take by weighing 3.00g (0.01mol) isocyanuric acid three-glycidyl ester and be dissolved in the 40ml THF, with being added drop-wise in the there-necked flask in the about 0.5h of this solution, be warming up to 50 ℃ of insulation reaction 4h after dropwising under 20 ℃; Be cooled to 30 ℃ again, at the efficient reflux condensing tube expansion soft seal cover that extremely to stretch, feeding 4.40g (0.10mol) oxyethane under the liquid level adorned suitable for reading; Feed process control temp and be not higher than 40 ℃, then be warming up to 50 ℃ of insulation reaction 3h, check reaction solution pH is a terminal point at 5-6; After reaction finishes; Underpressure distillation goes out solvent and low boilers gets product three { 2-chloro-3-[three (chlorine propoxy-) silicon acyloxy] propyl group } chlorinated isocyanurates, and productive rate is 95.5%, flash-point (open cup): 214 ± 5 ℃; Decomposition temperature: 278 ± 5 ℃, refractive index: n D 20=1.6648, density (25 ℃): 1.383g/cm 3
Embodiment 3 adds the 10ml dioxane in the 100ml there-necked flask that whisking appliance, TM and efficient reflux condensing tube are housed, catch up with the air in the most bottle with nitrogen, accurately draws 3.40ml (0.03mol) SiCl 4Place there-necked flask.Take by weighing 3.00g (0.01mol) isocyanuric acid three-glycidyl ester and be dissolved in the 40ml dioxane, with being added drop-wise in the there-necked flask in the about 0.5h of this solution, be warming up to 60 ℃ of insulation reaction 5h after dropwising under 20 ℃; Be cooled to 30 ℃ again, at the efficient reflux condensing tube expansion soft seal cover that extremely to stretch, feeding 4.84g (0.11mol) oxyethane under the liquid level adorned suitable for reading; Feed process control temp and be not higher than 40 ℃, then be warming up to 45 ℃ of insulation reaction 2h, check reaction solution pH is a terminal point at 5-6; After reaction finishes; Underpressure distillation goes out solvent and low boilers gets product three { 2-chloro-3-[three (chlorine propoxy-) silicon acyloxy] propyl group } chlorinated isocyanurates, and productive rate is 96.3%, flash-point (open cup): 214 ± 5 ℃; Decomposition temperature: 278 ± 5 ℃, refractive index: n D 20=1.6648, density (25 ℃): 1.383g/cm 3
Embodiment 4 adds the 10ml ethylene dichloride in the 100ml there-necked flask that whisking appliance, TM and efficient reflux condensing tube are housed, catch up with the air in the most bottle with nitrogen, accurately draws 3.40ml (0.03mol) SiCl 4Place there-necked flask.Take by weighing 3.00g (0.01mol) isocyanuric acid three-glycidyl ester and be dissolved in the 40ml ethylene dichloride, with being added drop-wise in the there-necked flask in the about 0.5h of this solution, be warming up to 70 ℃ of insulation reaction 5h after dropwising under 20 ℃; Be cooled to 30 ℃ again, at the efficient reflux condensing tube expansion soft seal cover that extremely to stretch, feeding 5.28g (0.12mol) oxyethane under the liquid level adorned suitable for reading; Feed process control temp and be not higher than 40 ℃, then be warming up to 45 ℃ of insulation reaction 2h, check reaction solution pH is a terminal point at 5-6; After reaction finishes; Underpressure distillation goes out solvent and low boilers gets product three { 2-chloro-3-[three (chlorine propoxy-) silicon acyloxy] propyl group } chlorinated isocyanurates, and productive rate is 97.3%, flash-point (open cup): 214 ± 5 ℃; Decomposition temperature: 278 ± 5 ℃, refractive index: n D 20=1.6648, density (25 ℃): 1.383g/cm 3
The routine main technologic parameters of table 1 preparation
Figure BSA00000750148300061
This case contriver also is applied to above-mentioned synthetic cyanuric acid chlorine propoxy-silicic acid chloroethene ester in the SE.The limiting oxygen index(LOI) of reference: GB/T2406-2008 " plastics combustibility test method-oxygen index method " test sample article.After getting product three { 2-chloro-3-[three (chlorine propoxy-) silicon acyloxy] propyl group } chlorinated isocyanurates, plasticizer phthalic acid dioctyl ester, synergistic flame retardant Antimony Trioxide: 99.5Min and SE and mixing in varing proportions; Extrude with forcing machine; Process the batten that diameter is 3mm; And its flame retardant properties tested, it is as shown in the table to have listed the part test result:
The flame retardant properties data of table 2 three { 2-chloro-3-[three (chlorine propoxy-) silicon acyloxy] propyl group } chlorinated isocyanurates
Figure BSA00000750148300071

Claims (5)

1. a nitrogen, silicon, chlorine element synergistic fire retardant three { 2-chloro-3-[three (chloroethoxy) silicon acyloxy] propyl group } tricarbimide ester cpds is characterized in that the structure of this compound is shown below:
Figure FSA00000750148200011
2. according to the preparation method of claim 1 said three { 2-chloro-3-[three (chloroethoxy) silicon acyloxy] propyl group } chlorinated isocyanurates, it is characterized in that this method is:
Under 20 ℃ of conditions, the organic solvent solution of certain density isocyanuric acid three-glycidyl ester is added drop-wise in the silicon tetrachloride of 3 times of moles, then be warming up to 50 ℃～70 ℃ sustained reaction 4～6h; Cool to 30 ℃ again; Liquid level feeds the oxyethane of certain mol proportion down; Then be warming up to 45 ℃～55 ℃ sustained reaction 2～3h; When reaction solution PH=5-6, excessive oxyethane and organic solvent and a spot of low boilers are removed in distillation, get three { 2-chloro-3-[three (chloroethoxy) silicon acyloxy] propyl group } chlorinated isocyanurates.
3. according to the preparation method of claim 2 said three { 2-chloro-3-[three (chloroethoxy) silicon acyloxy] propyl group } chlorinated isocyanurates, it is characterized in that: said finite concentration is that the quality of isocyanuric acid three-glycidyl ester is 1 with the volume of organic solvent ratio: 5-1: 15.
4. according to the preparation method of claim 2 said three { 2-chloro-3-[three (chloroethoxy) silicon acyloxy] propyl group } chlorinated isocyanurates, it is characterized in that: the oxyethane of said certain mol proportion is isocyanuric acid three-glycidyl ester: silicon tetrachloride: the propylene oxide mol ratio is 1: 3: 9-1: 3: 12.
5. according to the preparation method of claim 2 and 3 said three { 2-chloro-3-[three (chloroethoxy) silicon acyloxy] propyl group } chlorinated isocyanurates, it is characterized in that: described organic solvent is for being dioxane, THF, acetonitrile or ethylene dichloride.
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CN103554148A (en) * 2013-11-08 2014-02-05 苏州科技学院相城研究院 Flame retardant cyclo-bromoethyl trisilicate compound and preparation method thereof
CN103554146A (en) * 2013-11-08 2014-02-05 苏州科技学院相城研究院 Flame retardant tris(hydroxyethyl) isocyanurate trisilicate propyl chloride-bromine compound and preparation method thereof
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CN104710468A (en) * 2015-03-06 2015-06-17 苏州阳桥化工科技有限公司 Isocyanuric acid triester (dimethyl dihalide propoxy silicon acyloxy halide propyl) compound and preparation method thereof
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CN104672267A (en) * 2015-03-06 2015-06-03 苏州阳桥化工科技有限公司 Preparation method of sencor dimethyl halogenate ethyoxyl silicate ester compound serving as flame retardant
CN104672270A (en) * 2015-03-06 2015-06-03 苏州阳桥化工科技有限公司 Isocyanuric acid tri (dimethyl halide propoxy silicon acyloxy halide propyl) ester compound and preparation method thereof
CN104672271A (en) * 2015-03-06 2015-06-03 苏州阳桥化工科技有限公司 Isocyanuric acid tri (dimethyl halide ethyoxyl silicon acyloxy halide propyl) ester compound and preparation method thereof
CN104744504B (en) * 2015-03-06 2017-10-17 湖州睿高新材料有限公司 A kind of silicon, nitrogen, the preparation method of halogen multielement cooperative flame retardant immunomodulator compounds
CN104672267B (en) * 2015-03-06 2019-04-16 苏州阳桥化工科技有限公司 The preparation method of fire retardant match gram dimethyl halo ethyoxyl silicate ester compound
CN104710468B (en) * 2015-03-06 2018-05-04 苏州阳桥化工科技有限公司 Isocyanuric acid three (dimethyl dihalo- propoxyl group silicon acyloxy halogen propyl group) ester compounds and preparation method thereof
CN104672270B (en) * 2015-03-06 2018-05-04 苏州阳桥化工科技有限公司 Isocyanuric acid three (dimethyl halogen propoxyl group silicon acyloxy halogen propyl group) ester compounds and preparation method thereof
CN104710468A (en) * 2015-03-06 2015-06-17 苏州阳桥化工科技有限公司 Isocyanuric acid triester (dimethyl dihalide propoxy silicon acyloxy halide propyl) compound and preparation method thereof
CN104693230B (en) * 2015-03-06 2018-08-21 湖州睿高新材料有限公司 A kind of preparation method of silicon, nitrogen, halogen cooperative flame retardant plasticizer
CN107474220A (en) * 2017-08-21 2017-12-15 什邡市太丰新型阻燃剂有限责任公司 A kind of nitrogenous, silicon, chlorine ingrain fireproofing epoxy resin and preparation method thereof
CN107474220B (en) * 2017-08-21 2019-05-10 成都纺织高等专科学校 A kind of nitrogenous, silicon, chlorine ingrain fireproofing epoxy resin and preparation method thereof

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