CN102731544A - Triazine trichloropropoxy tris(chloroethyl) silicate compound and preparation method thereof - Google Patents
Triazine trichloropropoxy tris(chloroethyl) silicate compound and preparation method thereof Download PDFInfo
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- CN102731544A CN102731544A CN2012102470394A CN201210247039A CN102731544A CN 102731544 A CN102731544 A CN 102731544A CN 2012102470394 A CN2012102470394 A CN 2012102470394A CN 201210247039 A CN201210247039 A CN 201210247039A CN 102731544 A CN102731544 A CN 102731544A
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Abstract
The invention relates to a tris(2-chloro-3-[tris (chloroethoxy) silicon acyloxy] propyl) isocyanurate compound whic is a N-Si-Cl three-element synergistic fire retardant plasticizer, and a preparation method of the compound. The compound has a structure shown in the specification. The preparation method of the compound comprises the following steps: dropwise adding an organic solvent solution of triglycidyl isocyanurate to silicon tetrachloride and reacting for 4-6h at 50-70 DEG C; cooling to 30 DEG C; dropwise adding chlorohydrin and reacting for 3-4h at 45-55 DEG C; adding an acid-binding agent for adjusting pH to be 5-6; and purifying to finally obtain tris(2-chloro-3-[tris (chloroethoxy) silicon acyloxy] propyl) isocyanurate. The compound has good fire retardant plasticity and is applicable to fire retardant plasticizers for polyvinyl chloride, polyurethane, epoxy resin, unsaturated resin and the like; moreover, the production process of the compound is simple and low in cost and is applicable to industrial production.
Description
Technical field
The present invention relates to a kind of nitrogen, silicon, chlorine element synergistic fire retardant triazine trichlorine propoxy-silicic acid three (chloroethyl) ester cpds 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 progressive synthesized polymer material of science and technology more and more widely be applied to social every field; Again because synthesized polymer material generally all has inflammableness; Easy initiation fire accident; Normal people's the lives and properties of giving bring serious threat, solve the inflammableness problem of synthetic materials, 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 the maximum organic fire-retardant of present consumption.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, chlorine element synergistic fire retardant triazine trichlorine propoxy-silicic acid three (chloroethyl) ester cpds 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:
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 mol ratio of control raw material is added drop-wise to the organic solvent solution of certain density isocyanuric acid three-glycidyl ester in the silicon tetrachloride, then is warming up to 50 ℃～70 ℃ sustained reaction 4～6h; Cool to 30 ℃ again, drip the glycol chlorohydrin of certain mol proportion, drip process control temp and be not higher than 40 ℃; Then, add the acid binding agent of quality product 1%-3%, transfer to PH=5-6 at 45 ℃～55 ℃ reaction 3～4h; Stir 1h, filter, filtrating distills out organic solvent and excessive glycol chlorohydrin (reclaim and use); Decompression steams a small amount of low boilers again, gets 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 mol ratio of controlling raw material as stated is meant isocyanuric acid three-glycidyl ester: silicon tetrachloride: the glycol chlorohydrin mol ratio is 1: 3: 9-1: 3: 12.
Aforesaid organic solvent is dioxane, THF, acetonitrile or ethylene dichloride.
Aforesaid acid binding agent is triethylamine, N, accelerine, trimeric cyanamide or pyridine.
Triazine trichlorine propoxy-silicic acid of the present invention three (chloroethyl) ester is colourless or light yellow liquid, and the product yield is 92.6%～96.6%, 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 triazine trichlorine propoxy-silicic acid three (chloroethyl) ester is shown below:
Compared with prior art, beneficial effect of the present invention is:
1. because triazine trichlorine propoxy-silicic acid of the present invention three (chloroethyl) ester 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 synthesizes of triazine trichlorine propoxy-silicic acid 2. of the present invention three (chloroethyl) ester cpds is given off has been developed an effective way; Have good benefits in environment, have good economic benefits again.
The synthesis technique equipment of triazine trichlorine propoxy-silicic acid 3. of the present invention three (chloroethyl) ester is simple and easy to control, with low cost, is suitable for various dissimilar enterprises 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; Ground adds 7.25g (0.09mol) glycol chlorohydrin, drips process control temp and is not higher than 40 ℃, then is warming up to 55 ℃ of insulation reaction 4h; After treating that hydrogenchloride has been put, add about 1g triethylamine, transfer to reaction solution pH=5-6; Stir 1h, filter, filtrating distills out organic solvent (reclaim and use); Decompression steams a small amount of low boilers again, gets product three { 2-chloro-3-[three (chloroethoxy) silicon acyloxy] propyl group } chlorinated isocyanurates, and productive rate is 93.4%; 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; Splash into 8.1g (0.10mol) glycol chlorohydrin, drip process control temp and be not higher than 40 ℃, then be warming up to 50 ℃ of insulation reaction 4h, treat that hydrogenchloride has been put after; Add about 1g N, accelerine transfers to reaction solution pH=5-6; Stir 1h, filter, filtrating distills out organic solvent and excessive glycol chlorohydrin (reclaim and use); Decompression steams a small amount of low boilers again, gets product three { 2-chloro-3-[three (chloroethoxy) silicon acyloxy] propyl group } chlorinated isocyanurates, and productive rate is 94.3%; Flash-point (open cup): 214 ± 5 ℃, decomposition temperature: 278 ± 5 ℃, refractive index: n
D 20=1.6648, density (25 ℃): 1.383g/cm
3
Embodiment 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; Be added dropwise to 8.86g (0.11mol) glycol chlorohydrin, drip process control temp and be not higher than 40 ℃, then be warming up to 45 ℃ of insulation reaction 3h; After treating that hydrogenchloride has been put, add about 1g trimeric cyanamide, transfer to reaction solution pH=5-6; Stir 1h, filter, filtrating distills out organic solvent and excessive glycol chlorohydrin (reclaim and use); Decompression steams a small amount of low boilers again, gets product three { 2-chloro-3-[three (chloroethoxy) silicon acyloxy] propyl group } chlorinated isocyanurates, and productive rate is 96%; 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; Be added dropwise to 9.66g (0.12mol) glycol chlorohydrin, drip process control temp and be not higher than 40 ℃, then be warming up to 45 ℃ of insulation reaction 3h; After treating that hydrogenchloride has been put, add about 1g pyridine, transfer to reaction solution pH=5-6; Stir 1h, filter, filtrating distills out organic solvent and excessive glycol chlorohydrin (reclaim and use); Decompression steams a small amount of low boilers again, gets product three { 2-chloro-3-[three (chloroethoxy) silicon acyloxy] propyl group } chlorinated isocyanurates, and productive rate is 97.1%; 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
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 (chloroethoxy) 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 (chloroethoxy) silicon acyloxy] propyl group } chlorinated isocyanurates
Claims (7)
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:
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 mol ratio of control raw material is added drop-wise to the organic solvent solution of certain density isocyanuric acid three-glycidyl ester in the silicon tetrachloride, then is warming up to 50 ℃～70 ℃ sustained reaction 4～6h; Cool to 30 ℃ again, drip the glycol chlorohydrin of certain mol proportion, drip process control temp and be not higher than 40 ℃; Then at 45 ℃～55 ℃ reaction 3～4h; Add the acid binding agent of quality product 1%-3%, transfer to PH=5～6, stir 1h; Purified processing gets 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: 5～1: 15 with the volume of organic solvent ratio.
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 mol ratio of said control raw material is an isocyanuric acid three-glycidyl ester: silicon tetrachloride: the glycol chlorohydrin mol ratio is 1: 3: 9～1: 3: 12.
5. 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 organic solvent is dioxane, THF, acetonitrile or ethylene dichloride.
6. 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 acid binding agent is triethylamine, N, accelerine, trimeric cyanamide or pyridine.
7. 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 said purified filtration that is treated to; Filtrating distills out organic solvent and excessive glycol chlorohydrin, and decompression steams a small amount of low boilers again.
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| CN104693230A (en) * | 2015-03-06 | 2015-06-10 | 苏州阳桥化工科技有限公司 | Preparation method of plasticizer with collaborative flame retardancy of silicon, nitrogen and halogen |
| CN109183408A (en) * | 2018-08-15 | 2019-01-11 | 江南大学 | A kind of LBL self-assembly flame-proof cotton fabric and preparation method thereof |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN104693230A (en) * | 2015-03-06 | 2015-06-10 | 苏州阳桥化工科技有限公司 | Preparation method of plasticizer with collaborative flame retardancy of silicon, nitrogen and halogen |
| CN104672271B (en) * | 2015-03-06 | 2018-05-04 | 苏州阳桥化工科技有限公司 | Isocyanuric acid three (dimethyl halogen ethyoxyl silicon acyloxy halogen propyl group) ester compounds 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 |
| CN109183408A (en) * | 2018-08-15 | 2019-01-11 | 江南大学 | A kind of LBL self-assembly flame-proof cotton fabric and preparation method thereof |
| CN109183408B (en) * | 2018-08-15 | 2020-07-07 | 江南大学 | Layer-by-layer self-assembly flame-retardant cotton fabric and preparation method thereof |
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