CN102731553B - Tris(dichloropropyl) tribromophenoxy chloropropyl silicate compound and preparation method thereof - Google Patents
Tris(dichloropropyl) tribromophenoxy chloropropyl silicate compound and preparation method thereof Download PDFInfo
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- CN102731553B CN102731553B CN201210247257.8A CN201210247257A CN102731553B CN 102731553 B CN102731553 B CN 102731553B CN 201210247257 A CN201210247257 A CN 201210247257A CN 102731553 B CN102731553 B CN 102731553B
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Abstract
The invention relates to a tris(dichloropropyl) tribromophenoxy chloropropyl silicate compound which is a silicon-halogen synergistic fire retardant, and a preparation method of the compound. The compound has a structure shown in a formula described in the specification; and in the formula, OC3H5Cl2 is OCH2CHClCH2Cl or OCH (CH2Cl) 2. The preparation method of the compound comprises the following steps: reacting tribromophenyl glycidyl ether and silicon tetrachloride according to the same molar ratio in an organic solvent for 4-6h at 60-80 DEG C; then dropwise adding dichloropropanol according to a certain molar ratio, reacting for 4-8h at 50-100 DEG C; and finally purifying to obtain faint yellow liquid which is the tris(dichloropropyl) tribromophenoxy chloropropyl silicate. The compound is applicable to fire retardants for polyvinyl chloride, polyurethane, epoxy resin, unsaturated resin and other materials; and the production process is simple, low in equipment investment and cost, and suitable for industrial production.
Description
Technical field
The present invention relates to a kind of silicic acid three (two chloropropyls) tribromophenoxy chloropropyl ester cpds and preparation method thereof.Silicic acid three (two chloropropyls) tribromophenoxy chloropropyl ester belongs to silicon halogen synergistic fire retardant, is suitable for fire retardant or the softening agent of the materials such as polyvinyl chloride, urethane, epoxy resin, unsaturated polyester.
Background technology
The application of macromolecular material is more and more extensive, but often causes fire due to its inflammable characteristic, thus facilitates the fast development of fire-retardant science and technology.Flame-retardant plasticizer is the processing of high molecular material auxiliary agent simultaneously with anti-flaming function and plastification, and it can overcome and adds due to softening agent the problem making macromolecular material more inflammable.Flame-retardant plasticizer excellent is at present of less types, and people always expect to develop new and effective, low toxicity and cheap flame-retardant plasticizer.To achieve these goals, hot research problem is become to the exploitation of multielement cooperative flame retardant softening agent.Press down cigarette because silicon-type flame-retardant plasticizer has, promote into the excellent properties of carbon and obtain the attention of people.But silicon-type product exist expensive, use range is narrow, be restricted.Inventor has researched and developed with the silicon tetrachloride as by-product of polysilicon industry as novel silicon halogen cooperative flame retardant softening agent silicic acid three (two chloropropyls) tribromophenoxy chloropropyl ester prepared by raw material.The present invention can solve a difficult problem for silicon tetrachloride comprehensive utilization, opens again cheap excellent flame-retardant plasticizer new variety, and has good economic implications.
Summary of the invention
An object of the present invention is to synthesize a kind of silicon halogen cooperative flame retardant plasticized compound silicic acid three (two chloropropyls) tribromophenoxy chloropropyl ester with the silicon tetrachloride as by-product of polysilicon industry, its fire-retardant plasticity is good, can effectively overcome deficiency of the prior art.
For achieving the above object, present invention employs following technical scheme:
A kind of silicic acid three (two chloropropyls) tribromophenoxy chloropropyl ester cpds, it is characterized in that, the structure of this compound is shown below:
OC in its formula
3h
5cl
2for OCH
2cHClCH
2cl or OCH (CH
2cl)
2.
Another object of the present invention is to the preparation method proposing a kind of silicic acid three (two chloropropyls) tribromophenoxy chloropropyl ester as mentioned above; 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:
Under stirring, to be added drop-wise in the silicon tetrachloride of equimolar ratio at the organic solvent solution 20 DEG C of tribromo phenyl glycidyl ether, drip process temperature and be no more than 35 DEG C, 60-80 DEG C is warmed up to after dripping off, insulation reaction 4-6h, cool to 40 DEG C again, the dichlorohydrine of certain mol proportion is added drop-wise in above-mentioned reaction soln, after dripping off, be warmed up to 50-100 DEG C, insulation reaction 4-8h, add the acid binding agent of quality product 1%-3%, be adjusted to pH=5-6, stir 1h, filter, filtrate distills out organic solvent (reclaim and use), decompression steams excessive dichlorohydrine (reclaim and use) and a small amount of low boilers again, obtain weak yellow liquid silicic acid three (two chloropropyls) tribromophenoxy chloropropyl ester.
Organic solvent described above is tetrahydrofuran (THF), acetonitrile, ethylene dichloride or dioxane.
The dichlorohydrine of certain mol proportion described above is silicon tetrachloride: tribromo phenyl glycidyl ether: dichlorohydrine=1: 1: 3-1: 1: 4;
Dichlorohydrine as above is the mixture of 2,3-dichlorohydrine, 1,3-bis-chloro-2-propyl alcohol or 2,3-dichlorohydrine and the chloro-2-propyl alcohol of 1,3-bis-.
Acid binding agent as above is triethylamine, DMA, trimeric cyanamide or pyridine.
Silicic acid three (2,3-bis-chloropropyl) tribromophenoxy chloropropyl ester of the present invention is light yellow viscous liquid, its flash-point (open cup): 228 ± 5 DEG C, decomposition temperature: 302 ± 5 DEG C, density (25 DEG C): 1.858g/cm
3, refractive index: n
d 25=1.6625; Silicic acid three (1,3-bis-chloropropyl) tribromophenoxy chloropropyl ester is light yellow viscous liquid, its flash-point (open cup): 228 ± 5 DEG C, decomposition temperature: 302 ± 5 DEG C, density (25 DEG C): 1.856g/cm
3, refractive index: n
d 25=1.6629; Productive rate is 94.3% ~ 98.0%, and 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 silicic acid three (two chloropropyls) tribromophenoxy chloropropyl ester is shown below:
OC in its formula
3h
5cl
2for OCH
2cHClCH
2cl or OCH (CH
2cl)
2.
Compared with prior art, innovation of the present invention is:
1. because the structure of silicon halogen cooperative flame retardant softening agent silicic acid three (two chloropropyls) tribromophenoxy chloropropyl ester 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 polysilicon industry silicon tetrachloride as by-product for Material synthesis silicon halogen cooperative flame retardant softening agent silicic acid three (two chloropropyls) tribromophenoxy chloropropyl ester, 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.
Contriver thinks that industrial dichlorohydrine mostly is alcohol mixture, and it has application value most, special the product that dichlorohydrine synthesizes that mixes obtained with epoxy chloropropane and hydrochloric acid addition open loop has been beaten following spectrogram.
1, the infrared spectrogram of silicic acid three (two chloropropyls) tribromophenoxy chloropropyl ester, refers to Figure of description Fig. 1:
Fig. 1 shows, 2959.5cm
-1place is the stretching vibration peak of methylene radical c h bond; 1630cm
-1place is the skeleton stretching vibration peak of phenyl ring; 3080cm
-1place is the C-H stretching vibration peak of phenyl ring; 1104cm
-1place is the stretching vibration peak of Si-O-C key; 1046cm
-1place is the stretching vibration peak of C-Br key; 492cm
-1place is the stretching vibration peak of C-Cl key; 1248cm
-1place is the stretching vibration peak of Ar-O key.
2, the nuclear magnetic spectrum figure of silicic acid three (two chloropropyls) tribromophenoxy chloropropyl ester, refers to Figure of description Fig. 2:
Fig. 2 shows, deuterochloroform is solvent, and δ 3.61 ~ 3.77 is Si-OCH (CH
2cl)
2on the methyl hydrogen peak that is connected with chlorine and Si-OCH
2cHClCH
2the upper methyl hydrogen peak be connected with chlorine of Cl; δ 3.78 ~ 3.88 is Si-OCH
2cHClCH
2the upper methylene radical hydrogen peak be connected with chlorine of Cl; δ 3.88 ~ 3.98 is Ar-OCH
2cHClCH
2the upper methylene radical hydrogen peak be connected with chlorine of O-Si; δ 4.02 ~ 4.23 is Ar-OCH
2cHClCH
2the methylene radical hydrogen peak that O-Si is upper to be connected with silica and Si-OCH
2cHClCH
2the upper methylene radical hydrogen peak be connected with silica of Cl; δ 4.40 ~ 4.57 is Si-OCH (CH
2cl)
2on the methyne hydrogen peak that is connected with oxygen; δ 4.67 ~ 4.78 is Ar-OCH
2cHClCH
2the methylene radical hydrogen peak that the upper and fragrant oxygen of O-Si is connected; δ 7.55 ~ 7.70 is hydrogen peak on phenyl ring; The proton peak that δ 7.26 exchanges for solvent carbon deuterium chloride.
Embodiment
Below in conjunction with specific embodiment, technical scheme of the present invention is described further.
Under stirring, at 20 DEG C, the organic solvent solution of tribromo phenyl glycidyl ether is added drop-wise in the silicon tetrachloride of equimolar ratio, dropping process is no more than 35 DEG C, 60-80 DEG C is warmed up to after dripping off, insulation reaction 4-6h, cool to 40 DEG C again, the dichlorohydrine of certain mol proportion is added drop-wise in above-mentioned reaction soln, after dripping off, be warmed up to 50-100 DEG C, insulation reaction 4-8h, add the acid binding agent of quality product 1%-3%, be adjusted to pH=5-6, stir 1h, filter, filtrate distills out organic solvent (reclaim and use), decompression steams excessive dichlorohydrine (reclaim and use) and a small amount of low boilers again, obtain weak yellow liquid silicic acid three (two chloropropyls) tribromophenoxy chloropropyl ester.
Embodiment 1 is being equipped with agitator, thermometer, in the 100ml four-hole boiling flask of high performance reflux condenser, add tetrahydrofuran (THF) 10ml, 5.1g (0.03mol, 3.4ml) silicon tetrachloride, at 20 DEG C, the solution of 11.6g (0.03mol) the tribromo phenyl glycidyl ether dissolved with 50ml tetrahydrofuran (THF) is dripped in 60min, drip process control temp and be no more than 35 DEG C, after dripping off, 60 DEG C are warmed up in 1h, insulation 6h, then in the cooling condition, 2 are dripped in 1h, 3-dichlorohydrine 11.61g (0.09mol), after dripping off, 50 DEG C of insulation reaction 8h, reaction terminates, cool to 40 DEG C, add about 0.5 gram of triethylamine acid binding agent, be adjusted to pH=5-6, stir 1h, filter, filtrate distills out organic solvent (reclaim and use), decompression steams a small amount of low boilers again, obtain weak yellow liquid silicic acid three (2, 3-bis-chloropropyl) tribromophenoxy chloropropyl ester, product yield 94.3%, its flash-point (open cup): 228 ± 5 DEG C, decomposition temperature: 302 ± 5 DEG C, density (25 DEG C): 1.858g/cm
3, refractive index: n
d 25=1.6625.
Embodiment 2 is being equipped with agitator, thermometer, in the 100ml four-hole boiling flask of high performance reflux condenser, add acetonitrile 10ml, 5.1g (0.03mol, 3.4ml) silicon tetrachloride, at 20 DEG C, the solution of 11.6g (0.03mol) the tribromo phenyl glycidyl ether dissolved with 50ml acetonitrile is dripped in 60min, drip process control temp and be no more than 35 DEG C, after dripping off, 60 DEG C are warmed up in 1h, insulation 5h, then in the cooling condition, 2 are dripped in 1h, 3-dichlorohydrine 12.77g (0.099mol), after dripping off, 70 DEG C of insulation reaction 7h, reaction terminates, cool to 40 DEG C, add about 0.5g N, accelerine acid binding agent, be adjusted to pH=5-6, stir 1h, filter, filtrate distills out organic solvent (reclaim and use), decompression steams excessive dichlorohydrine (reclaim and use) and a small amount of low boilers again, obtain weak yellow liquid silicic acid three (2, 3-bis-chloropropyl) tribromophenoxy chloropropyl ester, product yield 95.1%, its flash-point (open cup): 228 ± 5 DEG C, decomposition temperature: 302 ± 5 DEG C, density (25 DEG C): 1.858g/cm
3, refractive index: n
d 25=1.6625.
Embodiment 3 is being equipped with agitator, thermometer, in the 100ml four-hole boiling flask of high performance reflux condenser, add ethylene dichloride 10ml, 5.1g (0.03mol, 3.4ml) silicon tetrachloride, at 20 DEG C, the solution of 11.6g (0.03mol) the tribromo phenyl glycidyl ether dissolved with 50ml ethylene dichloride is dripped in 60min, drip process control temp and be no more than 35 DEG C, after dripping off, 70 DEG C are warmed up in 1h, insulation 4h, then in the cooling condition, 1 is dripped in 1h, 3-dichlorohydrine 13.93g (0.108mol), after dripping off, 80 DEG C of insulation reaction 6h, reaction terminates, cool to 40 DEG C, add about 0.5g pyridine acid binding agent, be adjusted to pH=5-6, stir 1h, filter, filtrate distills out organic solvent (reclaim and use), decompression steams excessive dichlorohydrine (reclaim and use) and a small amount of low boilers again, obtain weak yellow liquid silicic acid three (1, 3-bis-chloropropyl) tribromophenoxy chloropropyl ester, product yield 97.0%, its flash-point (open cup): 228 ± 5 DEG C, decomposition temperature: 302 ± 5 DEG C, density (25 DEG C): 1.856g/cm
3, refractive index: n
d 25=1.6629.
Embodiment 4 is being equipped with agitator, thermometer, in the 100ml four-hole boiling flask of high performance reflux condenser, add dioxane 10ml, 5.1g (0.03mol, 3.4ml) silicon tetrachloride, at 20 DEG C, the solution of 11.6g (0.03mol) the tribromo phenyl glycidyl ether dissolved with 50ml dioxane is dripped in 60min, drip process control temp and be no more than 35 DEG C, after dripping off, 80 DEG C are warmed up in 1h, insulation 4h, then in the cooling condition, 1 is dripped in 1h, 3-dichlorohydrine 14.71g (0.114mol), after dripping off, 90 DEG C of insulation reaction 5h, reaction terminates, cool to 40 DEG C, add about 0.5g trimeric cyanamide acid binding agent, be adjusted to pH=5-6, stir 1h, filter, filtrate distills out organic solvent (reclaim and use), decompression steams excessive dichlorohydrine (reclaim and use) and a small amount of low boilers again, obtain weak yellow liquid silicic acid three (1, 3-bis-chloropropyl) tribromophenoxy chloropropyl ester, product yield 97.5%, its flash-point (open cup): 228 ± 5 DEG C, decomposition temperature: 302 ± 5 DEG C, density (25 DEG C): 1.856g/cm
3, refractive index: n
d 25=1.6629.
Embodiment 5 is being equipped with agitator, thermometer, in the 100ml four-hole boiling flask of high performance reflux condenser, add dioxane 10ml, 5.1g (0.03mol, 3.4ml) silicon tetrachloride, at 20 DEG C, the solution of 11.6g (0.03mol) the tribromo phenyl glycidyl ether dissolved with 50ml dioxane is dripped in 60min, drip process control temp and be no more than 35 DEG C, after dripping off, 80 DEG C are warmed up in 1h, insulation 4h, then in the cooling condition, homemade mixing dichlorohydrine 15.48g (0.120mol) described above is dripped in 1h, after dripping off, 100 DEG C of insulation reaction 5h, reaction terminates, cool to 40 DEG C, add about 0.5g trimeric cyanamide acid binding agent, be adjusted to pH=5-6, stir 1h, filter, filtrate distills out organic solvent (reclaim and use), decompression steams excessive dichlorohydrine (reclaim and use) and a small amount of low boilers again, obtain weak yellow liquid silicic acid three (two chloropropyls) tribromophenoxy chloropropyl ester, product yield 98.0%, its flash-point (open cup): 228 ± 5 DEG C, decomposition temperature: 302 ± 5 DEG C, density (25 DEG C): 1.857g/cm
3, refractive index: n
d 25=1.6628.
Table 1 preparation example main technologic parameters
Silicic acid three (two chloropropyls) the tribromophenoxy chloropropyl ester of above-mentioned synthesis 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 product silicon halogen cooperative flame retardant softening agent silicic acid three (two chloropropyls) tribromophenoxy chloropropyl ester, plasticizer phthalic acid dioctyl ester, synergistic flame retardant antimonous oxide and polyvinyl chloride mix in varing proportions, extrude with forcing machine, make the batten that diameter is 3mm, and its flame retardant properties is tested, experiment shows that different isomeric product flame retardant propertiess is identical, thus experimental result does not indicate concrete isomer structure, and part test result is as shown in table 2:
The flame retardant properties data of table 2 silicic acid three (two chloropropyls) tribromophenoxy chloropropyl ester
Claims (3)
1. a preparation method for silicon halogen cooperative flame retardant softening agent silicic acid three (two chloropropyls) tribromophenoxy chloropropyl ester, it is characterized in that, the method is:
Control silicon tetrachloride: tribromo phenyl glycidyl ether: the mol ratio of dichlorohydrine is 1: 1: 3-1: 1: 4, at 20 DEG C, the organic solvent solution of tribromo phenyl glycidyl ether is added drop-wise in silicon tetrachloride, dropping process is no more than 35 DEG C, 60-80 DEG C is warmed up to after dripping off, insulation reaction 4-6h, cool to 40 DEG C again, dichlorohydrine is added drop-wise in above-mentioned reaction soln, after dripping off, be warmed up to 50-100 DEG C, insulation reaction 4-8h, add the acid binding agent of quality product 1%-3%, be adjusted to pH=5-6, stir 1h, filter, filtrate distills out organic solvent, decompression steams excessive dichlorohydrine and a small amount of low boilers again, obtain weak yellow liquid silicic acid three (two chloropropyls) tribromophenoxy chloropropyl ester, this compound has the structure be shown below:
OC in its formula
3h
5cl
2for OCH
2cHClCH
2cl or OCH (CH
2cl)
2.
2. the preparation method of silicic acid three (two chloropropyls) tribromophenoxy chloropropyl ester as claimed in claim 1, is characterized in that: described organic solvent is tetrahydrofuran (THF), acetonitrile, ethylene dichloride or dioxane.
3. the preparation method of silicic acid three (two chloropropyls) tribromophenoxy chloropropyl ester as claimed in claim 1, is characterized in that: described acid binding agent is triethylamine, DMA, trimeric cyanamide or pyridine.
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