CN109734749A - Five phenoxy group cyclotrinitrile phosphide of reactive flame retardant allyloxy and preparation method thereof - Google Patents
Five phenoxy group cyclotrinitrile phosphide of reactive flame retardant allyloxy and preparation method thereof Download PDFInfo
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- CN109734749A CN109734749A CN201811569026.2A CN201811569026A CN109734749A CN 109734749 A CN109734749 A CN 109734749A CN 201811569026 A CN201811569026 A CN 201811569026A CN 109734749 A CN109734749 A CN 109734749A
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- allyloxy
- flame retardant
- hexachlorocyclotriph
- sphazene
- reactive flame
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Abstract
The present invention relates to a kind of five phenoxy group cyclotrinitrile phosphides of reactive flame retardant allyloxy and preparation method thereof, and the structure of the compound is shown below:
Description
Technical field
The present invention relates to a kind of five phenoxy group cyclotrinitrile phosphide of reactive flame retardant allyloxy and preparation method thereof,
It is fire-retardant that the compound contains phosphorus, nitrogen dual element, can be used as unsaturated-resin, styrene, acrylate, polyester, polyurethane, epoxy
The fire retardant of resin, polyvinyl alcohol and coating etc..
Background technique
Since halogenated flame retardant can generate noxious material and release toxic gas in use, all to human body and environment
Can generate certain harm, thus fire retardant it is non-halogen cry it is higher and higher, the substitute of halogen containing flame-retardant is mainly at present
Phosphorus-nitrogen containing flame retardant.Phosphorus-nitrogen containing flame retardant has many advantages, such as efficient, low toxicity, therefore has good market prospects.
Five phenoxy group cyclotrinitrile phosphide of reactive flame retardant allyloxy disclosed by the invention belongs to more phosphorus, more nitrogen knots
Structure, phosphorus, nitrogen dual element cooperative flame retardant efficiency are high.It has reactive allyl functional group, can be used as reactive flame retardant use,
It can be used as additive flame retardant use.The product structure aromatic is stablized, and decomposition temperature is high, and will not discharge in combustion process has poison gas
Body is environment friendly flame retardant.And raw material is easy to get, and has a wide range of application, and has market in urgent need, before having application well and exploitation
Scape.
Summary of the invention
It is an object of the present invention to propose a kind of five phenoxy cyclotriphosphazene chemical combination of reactive flame retardant allyloxy
Object, the compound have reactive allyl functional group, can be used as reactive flame retardant for unsaturated-resin, styrene, propylene
The polymerization of acid esters etc. obtains ingrain fireproofing resin, and fire retardant do not migrate, does not influence the mechanical property of material；Also it can be used as addition type
Fire retardant is fire-retardant for polyester, polyurethane, epoxy resin, polyvinyl alcohol and coating etc..Its physical and chemical performance is stablized, nontoxic, resistance
Fuel efficiency can be high, good with high molecular material compatibility, can overcome deficiency in the prior art.
For achieving the above object, present invention employs following technical solutions:
A kind of five phenoxy group cyclotrinitrile phosphide of reactive flame retardant allyloxy, which is characterized in that the compound
Structure is shown below:
Another object of the present invention is to propose a kind of five phenoxy cyclotriphosphazene chemical combination of reactive flame retardant allyloxy
The preparation method of object, simple process are easy to large-scale production, and raw material is cheap and easy to get, and equipment investment is few, low in cost, should
Method are as follows:
Hexachlorocyclotriph,sphazene is dissolved in organic solvent, acid binding agent is added, controls hexachlorocyclotriph,sphazene, allyl alcohol, phenol
And the molar ratio of acid binding agent is 1: 1: 5: 6 reactions, in the case where ice-water bath is cooling, allyl alcohol is added dropwise, control temperature is not higher than 30 DEG C, instead
Answer 1h；Phenol is added, is warming up to 60~110 DEG C, 4~7h of insulation reaction；It is cooled to 30 DEG C and removes tiing up for generation hereinafter, filtering
Sour agent hydrochloride is evaporated under reduced pressure out organic solvent (recycling), adds 2~3 times of volumes of relative product Theoretical Mass grams
Ml distilled water wash twice, separate lower layer's organic phase, 2~3 times of volume milliliters of relative product Theoretical Mass grams be added
Several ethyl acetate, is dried with anhydrous sodium sulfate, is filtered, and filtrate decompression is distilled off ethyl acetate, obtains light yellow clear
Five phenoxy cyclotriphosphazene of liquid allyloxy.
This method may be used also are as follows:
Hexachlorocyclotriph,sphazene is dissolved in organic solvent, in the case where ice-water bath is cooling, equimolar allyl alcohol, control temperature is added dropwise
Degree is not higher than 30 DEG C, reacts 4h, until releasing without hydrogen chloride；The phenol for adding 5 times of moles of hexachlorocyclotriph,sphazene, is warming up to 60
~110 DEG C of 6~9h of reaction, until being released without hydrogen chloride；30 DEG C are cooled to hereinafter, be evaporated under reduced pressure out organic solvent (recycling),
The distilled water for adding relative product Theoretical Mass 2~3 times of volumes ml of grams washes twice, and separates lower layer's organic phase, adds
The ethyl acetate for entering relative product Theoretical Mass 2~3 times of volumes ml of grams, is dried with anhydrous sodium sulfate, is filtered, filter
Liquid vacuum distillation removes ethyl acetate, obtains five phenoxy cyclotriphosphazene of light yellow clear liquid allyloxy.
Acid binding agent as described above is triethylamine, n,N-Dimethylaniline or pyridine.
Organic solvent as described above is tetrahydrofuran, acetonitrile, dioxane or toluene, the volume milliliter of organic solvent
Several the ratio between quality grams with hexachlorocyclotriph,sphazene are 3: 1~5: 1.
Five phenoxy group cyclotrinitrile phosphide of reactive flame retardant allyloxy of the invention be light yellow clear liquid,
Its flash-point (open cup): 192 ± 5 DEG C, density: 1.441g/cm3(25 DEG C), index of refraction: nD 25=1.3998.Yield is
89.2%~95.6%, it can be used as unsaturated-resin, styrene, polyester, polyamide, epoxy resin, polyvinyl alcohol and coating etc.
Fire retardant.The preparation principle of the five phenoxy group cyclotrinitrile phosphide of reactive flame retardant allyloxy is shown below:
Compared with prior art, the invention has the beneficial effects that:
1. five phenoxy group cyclotrinitrile phosphide structure novel of reactive flame retardant allyloxy of the present invention, phosphorus content are
14.2%, nitrogen content 6.4%, ignition-proof element total content is 20.6%.Structure conjugation is stablized, and can be suitably used for various engineering plastics
High temperature process, nitrogen, phosphorus dual element cooperative flame retardant efficiency are high, have good plasticity；
2. five phenoxy group cyclotrinitrile phosphide of reactive flame retardant allyloxy of the present invention has reactive allyl function
Group, the polymerization that can be used as reactive flame retardant for unsaturated-resin, styrene etc. obtain ingrain fireproofing resin, and fire retardant does not move
Shifting, the mechanical property for not influencing material especially achieve the purpose that add response type, according to need for addition after unsaturated-resin
The amount for wanting arbitrarily to adjust fire retardant, reaches different flame retardant ratings, very convenient；Also it can be used as additive flame retardant to be used for
Polyester, polyamide, polyurethane, epoxy resin, polyvinyl alcohol and coating etc. it is fire-retardant.
3. five phenoxy cyclotriphosphazene of reactive flame retardant allyloxy of the present invention is halogen-free, it is good for the environment, belongs to swollen
The swollen environmental-friendly fire retardant of type；
4. the preparation method simple process of five phenoxy cyclotriphosphazene of reactive flame retardant allyloxy of the present invention, synthesized
Cheng Wuxu addition catalyst does not introduce impurity；Equipment is simple, low in cost, is suitable for large-scale production, there is good application and development
Prospect.
Detailed description of the invention
Following attached drawing is provided in order to further illustrate the structure and performance spy of product.
Fig. 1 is the infrared spectrogram of five phenoxy cyclotriphosphazene of reactive flame retardant allyloxy: Fig. 1 shows
1589.4cm-1, 1487.3cm-1For the framework deformation vibration absorption peak on phenyl ring；And 3112.6cm-1It is flexible for c h bond on phenyl ring
Vibration peak；1184.2cm-1For the absorption peak of P=N；1201.7cm-1For P-N absorption peak；954.8cm-1For the absorption peak of P-O-C；
1598.8cm-1For the absorption peak of C=C double bond on allyl； 1204.7cm-1For the absorption peak of C-O key on allyl.
Fig. 2 is the nuclear magnetic spectrum figure of five phenoxy cyclotriphosphazene of reactive flame retardant allyloxy: Fig. 2 shows with deuterated
DMSO is CH at δ 4.12-4.19 as solvent2=CH-CH2The upper methylene hydrogen peak being connected with oxygen-O；It is at δ 5.04-5.23
CH2=CH-CH2The upper double bond methylene hydrogen peak-O；It is CH at δ 5.79-6.102=CH-CH2The hydrogen peak of the upper-CH- of-O；δ6.47-
It is the hydrogen peak on phenyl ring at 7.08.
Fig. 3 is the heat analysis map of five phenoxy cyclotriphosphazene of reactive flame retardant allyloxy: Fig. 3 shows to work as temperature
When being increased to 281 DEG C, sample starts weightlessness, weight-loss ratio 5%；When temperature is 399 DEG C, the weight-loss ratio of sample reaches 50%；
Still there is 22% residue remaining at 800 DEG C, illustrates that product has preferable thermal stability.
Specific embodiment
Below in conjunction with specific embodiment, technical scheme is described further.
Embodiment 1 is being equipped with blender, thermometer and condenser pipe, and in the condenser pipe 250mL suitable for reading equipped with drying tube
In there-necked flask, with the air in nitrogen displacement bottle falling, 6.95g (0.02mol) hexachlorocyclotriph,sphazene, 120mL tetrahydrofuran is added
With 12.12g (0.12mol) triethylamine, after stirring dissolves hexachlorocyclotriph,sphazene, the cooling lower dropwise addition 1.16g of ice-water bath
(0.02mol) allyl alcohol, control temperature are no more than 30 DEG C, react 1h；9.40g (0.10mol) phenol is added, is warming up to 60 DEG C,
React 7h；30 DEG C are cooled to hereinafter, filtering the triethylamine hydrochloride for removing and generating, filtrate decompression is distilled off tetrahydrofuran and (returns
Receive and utilize), it is separately added into 25mL water washing twice, separates lower layer's organic phase, 20mL ethyl acetate is added, with 1g anhydrous magnesium sulfate
It is dried, filters, filtrate decompression is distilled off ethyl acetate, obtains five phenoxy group ring of light yellow clear liquid allyloxy, three phosphorus
Nitrile.Yield is 90.1%, flash-point (open cup): 192 ± 5 DEG C, density: 1.441g/cm3(25 DEG C), index of refraction: nD 25=
1.3998。
Embodiment 2 is being equipped with blender, thermometer and condenser pipe, and in the condenser pipe 250mL suitable for reading equipped with drying tube
In there-necked flask, with the air in nitrogen displacement bottle falling, be added 6.95g (0.02mol) hexachlorocyclotriph,sphazene, 120mL acetonitrile and
12.12g (0.12mol) triethylamine, after stirring dissolves hexachlorocyclotriph,sphazene, cooling lower dropwise addition 1.16g (0.02mol) of ice-water bath
Allyl alcohol, control temperature are no more than 30 DEG C, react 1h；9.40g (0.10mol) phenol is added, is warming up to 80 DEG C, reacts 6h；Drop
For temperature to 30 DEG C hereinafter, filtering the triethylamine hydrochloride for removing and generating, acetonitrile (recycling) is distilled off in filtrate decompression, respectively plus
Enter 25mL water washing twice, separate lower layer's organic phase, 20mL ethyl acetate is added, is dried with 1g anhydrous magnesium sulfate, takes out
Filter, filtrate decompression are distilled off ethyl acetate, obtain five phenoxy cyclotriphosphazene of light yellow clear liquid allyloxy.Yield is
92.7%, flash-point (open cup): 192 ± 5 DEG C, density: 1.441g/cm3(25 DEG C), index of refraction: nD 25=1.3998.
Embodiment 3 is being equipped with blender, thermometer and condenser pipe, and in the condenser pipe 250mL suitable for reading equipped with drying tube
In there-necked flask, with the air in nitrogen displacement bottle falling, 6.95g (0.02mol) hexachlorocyclotriph,sphazene, 120mL dioxane is added
With 14.52g (0.12mol) n,N-Dimethylaniline, after stirring dissolves hexachlorocyclotriph,sphazene, the cooling lower dropwise addition of ice-water bath
1.16g (0.02mol) allyl alcohol, control temperature are no more than 30 DEG C, react 1h；9.40g (0.10mol) phenol is added, is warming up to
100 DEG C, react 5h；30 DEG C are cooled to hereinafter, filtering the n,N-Dimethylaniline hydrochloride for removing and generating, filtrate decompression distillation removes
Dioxane (recycling) is gone, is separately added into 25mL water washing twice, separates lower layer's organic phase, 20mL ethyl acetate is added,
It is dried, is filtered with 1g anhydrous magnesium sulfate, filtrate decompression is distilled off ethyl acetate, obtains light yellow clear liquid allyloxy
Five phenoxy cyclotriphosphazenes.Yield is 95.6%, flash-point (open cup): 192 ± 5 DEG C, density: 1.441g/cm3(25 DEG C), folding
Light rate: nD 25=1.3998.
Embodiment 4 is being equipped with blender, thermometer and condenser pipe, and in the condenser pipe 250mL tri- suitable for reading equipped with drying tube
In mouth bottle, with the air in nitrogen displacement bottle falling, 6.95g (0.02mol) hexachlorocyclotriph,sphazene, 120mL toluene and 9.48g is added
1.16g (0.02mol) allyl alcohol is at the uniform velocity added dropwise after stirring dissolves hexachlorocyclotriph,sphazene in (0.12mol) pyridine under ice-water bath,
React 1h；9.40g (0.10mol) phenol is added, is warming up to 110 DEG C, reacts 4h；It is cooled to 30 DEG C and is generated hereinafter, filtering and removing
Pyridine hydrochloride, filtrate decompression is distilled off toluene (recycling), is separately added into 25mL water washing twice, and separating lower layer has
Machine phase is added 20mL ethyl acetate, is dried with 1g anhydrous magnesium sulfate, filters, and filtrate decompression is distilled off ethyl acetate, obtains
Five phenoxy cyclotriphosphazene of light yellow clear liquid allyloxy.Yield is 93.0%, flash-point (open cup): 192 ± 5 DEG C, close
Degree: 1.441g/cm3(25 DEG C), index of refraction: nD 25=1.3998.
Embodiment 5 is being equipped with blender, thermometer, high performance reflux condenser and is inhaling in the condenser pipe hydrogen chloride suitable for reading that is connected to
In the 250mL four-hole boiling flask of receiving apparatus, the air in most bottle is caught up with nitrogen, takes the hexachlorocyclotriph,sphazene of 6.95g (0.02mol)
It is dissolved in the tetrahydrofuran solution of 120mL, under ice-water bath is cooling, 1.16g (0.02mol) allyl alcohol is added dropwise, control temperature is no more than
30 DEG C, 4h is reacted, until hydrogen chloride is all released；9.40g (0.10mol) phenol is added, is warming up to 60 DEG C, 9h is reacted, until without chlorine
Change hydrogen to release；30 DEG C are cooled to hereinafter, vacuum distillation removing tetrahydrofuran (recycling), is separately added into 25mL water washing two
It is secondary, lower layer's organic phase is separated, 20mL ethyl acetate is added, is dried with 1g anhydrous magnesium sulfate, is filtered, filtrate decompression distillation removes
Ethyl acetate is removed, five phenoxy cyclotriphosphazene of light yellow clear liquid allyloxy is obtained.Yield is 89.2%, flash-point (opening
Cup): 192 ± 5 DEG C, density: 1.441g/cm3 (25 DEG C), index of refraction: nD 25=1.3998.
Embodiment 6 is being equipped with blender, thermometer, high performance reflux condenser and is inhaling in the condenser pipe hydrogen chloride suitable for reading that is connected to
In the 250mL four-hole boiling flask of receiving apparatus, the air in most bottle is caught up with nitrogen, takes 6.95g (0.02mol) hexachlorocyclotriph,sphazene molten
In the acetonitrile solution of 120mL, under ice-water bath is cooling, 1.16g (0.02mol) allyl alcohol is added dropwise, control temperature is no more than 30 DEG C,
4h is reacted, until hydrogen chloride is all released；9.40g (0.10mol) phenol is added, is warming up to 80 DEG C, 8h is reacted, until without hydrogen chloride
It releases；30 DEG C are cooled to hereinafter, vacuum distillation removing acetonitrile (recycling), is separately added into 25mL water washing twice, separates down
Layer organic phase, is added 20mL ethyl acetate, is dried with 1g anhydrous magnesium sulfate, filters, and acetic acid second is distilled off in filtrate decompression
Ester obtains five phenoxy cyclotriphosphazene of light yellow clear liquid allyloxy.Yield is 91.6%, flash-point (open cup): 192 ± 5
DEG C, density: 1.441g/cm3(25 DEG C), index of refraction: nD 25=1.3998.
Embodiment 7 is being equipped with blender, thermometer, high performance reflux condenser and is inhaling in the condenser pipe hydrogen chloride suitable for reading that is connected to
In the 250mL four-hole boiling flask of receiving apparatus, the air in most bottle is caught up with nitrogen, takes the hexachlorocyclotriph,sphazene of 6.95g (0.02mol)
It is dissolved in the dioxane solution of 120mL, under ice-water bath is cooling, 1.16g (0.02mol) allyl alcohol is added dropwise, control temperature is no more than
30 DEG C, 4h is reacted, until hydrogen chloride is all released；9.40g (0.10mol) phenol is added, is warming up to 100 DEG C, 7h is reacted, until nothing
Hydrogen chloride is released；30 DEG C are cooled to hereinafter, vacuum distillation removing dioxane (recycling), is separately added into 25mL water washing two
It is secondary, lower layer's organic phase is separated, 20mL ethyl acetate is added, is dried with 1g anhydrous magnesium sulfate, is filtered, filtrate decompression distillation removes
Ethyl acetate is removed, five phenoxy cyclotriphosphazene of light yellow clear liquid allyloxy is obtained.Yield is 94.3%, flash-point (opening
Cup): 192 ± 5 DEG C, density: 1.441g/cm3(25 DEG C), index of refraction: nD 25=1.3998.
Embodiment 8 equipped with blender, thermometer, high performance reflux condenser and is being connected to hydrogen chloride absorption condenser pipe is suitable for reading
In the 250mL four-hole boiling flask of device, the air in most bottle is caught up with nitrogen, takes the hexachlorocyclotriph,sphazene of 6.95g (0.02mol) molten
In the toluene solution of 120mL, under ice-water bath is cooling, 1.16g (0.02mol) allyl alcohol is added dropwise, control temperature is no more than 30 DEG C,
4h is reacted, until hydrogen chloride is all released；9.40g (0.10mol) phenol is added, is warming up to 110 DEG C, 6h is reacted, until without hydrogen chloride
It releases；30 DEG C are cooled to hereinafter, vacuum distillation removing toluene (recycling), is separately added into 25mL water washing twice, separates down
Layer organic phase, is added 20mL ethyl acetate, is dried with 1g anhydrous magnesium sulfate, filters, and acetic acid second is distilled off in filtrate decompression
Ester obtains five phenoxy cyclotriphosphazene of light yellow clear liquid allyloxy.Yield is 92.8%, flash-point (open cup): 192 ± 5
DEG C, density: 1.441g/cm3(25 DEG C), index of refraction: nD 25=1.3998.
1 preparation example main technologic parameters of table
Five phenoxy cyclotriphosphazene of reactive flame retardant allyloxy of above-mentioned synthesis is also applied to 191 by inventor
In unsaturated-resin, by five phenoxy cyclotriphosphazene of allyloxy and 191 unsaturated-resins, cyclohexanone peroxide and cobalt naphthenate
After mixing according to the proportion in following table, it pours into and is covered in the mold of glass wool cloth, long 15cm, width 0.7cm, thickness is made
The modified resin batten of 0.3cm.Then flame retardant property measurement is carried out to it, reference: GB/T2406-2008 " Plastics Combustion performance
Test method-oxygen index method " test sample item limit oxygen index.Test result is as shown in table 2:
2 reactive flame retardant allyloxy of table, five phenoxy cyclotriphosphazene flame retardant property in unsaturated-resin
It is generally acknowledged that the limit oxygen index of fire proofing, which reaches 27 or more, preferable flame retardant property.Work as known to table 2
When mass fraction of five phenoxy cyclotriphosphazene of allyloxy in 191 unsaturated-resins is 20%, LOI 29；It thus can be with
Find out that five phenoxy cyclotriphosphazene of reactive flame retardant allyloxy has preferable flame-retarded efficiency to 191 unsaturated-resins.
Claims (5)
1. a kind of five phenoxy group cyclotrinitrile phosphide of reactive flame retardant allyloxy, which is characterized in that the knot of the compound
Structure is shown below:
2. the preparation side of five phenoxy group cyclotrinitrile phosphide of reactive flame retardant allyloxy according to claim 1
Method, which is characterized in that this method are as follows:
Hexachlorocyclotriph,sphazene is dissolved in organic solvent, acid binding agent is added, control hexachlorocyclotriph,sphazene, allyl alcohol, phenol and is tied up
The molar ratio of sour agent is 1: 1: 5: 6 reactions, in the case where ice-water bath is cooling, allyl alcohol is added dropwise, control temperature is not higher than 30 DEG C, reaction
1h；Phenol is added, is warming up to 60~110 DEG C, 4~7h of insulation reaction；30 DEG C are cooled to hereinafter, acid is tied up in suction filtration removing generation
Agent hydrochloride, is evaporated under reduced pressure out organic solvent, adds the distillation of relative product Theoretical Mass 2~3 times of volumes ml of grams
Water washing twice, separates lower layer's organic phase, and the ethyl acetate of 2~3 times of volumes ml of relative product Theoretical Mass grams is added,
It is dried, is filtered with anhydrous sodium sulfate, filtrate decompression is distilled off ethyl acetate, obtains light yellow clear liquid allyloxy five
Phenoxy cyclotriphosphazene.
3. the preparation side of five phenoxy group cyclotrinitrile phosphide of reactive flame retardant allyloxy according to claim 1
Method, which is characterized in that this method are as follows:
Hexachlorocyclotriph,sphazene is dissolved in organic solvent, in the case where ice-water bath is cooling, equimolar allyl alcohol is added dropwise, control temperature is not
Higher than 30 DEG C, 4h is reacted, until releasing without hydrogen chloride；The phenol for adding 5 times of moles of hexachlorocyclotriph,sphazene, it is warming up to 60~
110 DEG C of 6~9h of reaction, until being released without hydrogen chloride；30 DEG C are cooled to hereinafter, be evaporated under reduced pressure out organic solvent, adds opposite production
The distilled water of object Theoretical Mass 2~3 times of volumes ml of grams washes twice, and separates lower layer's organic phase, and relative product reason is added
It by the ethyl acetate of 2~3 times of volumes ml of quality grams, is dried, is filtered with anhydrous sodium sulfate, filtrate decompression distillation removes
Ethyl acetate is removed, five phenoxy cyclotriphosphazene of light yellow clear liquid allyloxy is obtained.
4. the preparation side of five phenoxy group cyclotrinitrile phosphide of reactive flame retardant allyloxy according to claim 2
Method, it is characterised in that: the acid binding agent is triethylamine, n,N-Dimethylaniline or pyridine.
5. according to the preparation of five phenoxy group cyclotrinitrile phosphide of reactive flame retardant allyloxy described in claim 2 and 3
Method, it is characterised in that: the organic solvent is tetrahydrofuran, acetonitrile, dioxane or toluene, the volume of organic solvent
It ml is 3: 1~5: 1 with the ratio between the quality grams of hexachlorocyclotriph,sphazene.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101597308A (en) * | 2009-06-30 | 2009-12-09 | 广东榕泰实业股份有限公司 | The preparation method of hexaaniline cyclotriphosphazene and halogen-free flame retardant epoxy resin composition |
| CN102719206A (en) * | 2012-05-31 | 2012-10-10 | 四川东材科技集团股份有限公司 | Preparation method of halogen-free environment-friendly flame-retardant acrylate pressure-sensitive adhesive |
| CN105461751A (en) * | 2014-08-27 | 2016-04-06 | 青岛鑫润土苗木专业合作社 | Preparation method of high efficiency environment-friendly flame retardant |
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- 2018-12-10 CN CN201811569026.2A patent/CN109734749A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101597308A (en) * | 2009-06-30 | 2009-12-09 | 广东榕泰实业股份有限公司 | The preparation method of hexaaniline cyclotriphosphazene and halogen-free flame retardant epoxy resin composition |
| CN102719206A (en) * | 2012-05-31 | 2012-10-10 | 四川东材科技集团股份有限公司 | Preparation method of halogen-free environment-friendly flame-retardant acrylate pressure-sensitive adhesive |
| CN105461751A (en) * | 2014-08-27 | 2016-04-06 | 青岛鑫润土苗木专业合作社 | Preparation method of high efficiency environment-friendly flame retardant |
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| 王锐: ""环磷腈衍生物的制备及其在环氧树脂中的阻燃研究"", 《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》 * |
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