CN109734748A - Reactive flame retardant allyl amido pentaphene oxygroup cyclotrinitrile phosphide and preparation method thereof - Google Patents
Reactive flame retardant allyl amido pentaphene oxygroup cyclotrinitrile phosphide and preparation method thereof Download PDFInfo
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- CN109734748A CN109734748A CN201811568933.5A CN201811568933A CN109734748A CN 109734748 A CN109734748 A CN 109734748A CN 201811568933 A CN201811568933 A CN 201811568933A CN 109734748 A CN109734748 A CN 109734748A
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Abstract
The present invention relates to a kind of reactive flame retardant allyl amido pentaphene oxygroup cyclotrinitrile phosphides and preparation method thereof, and the structure of the compound is shown below:
Description
Technical field
The present invention relates to a kind of reactive flame retardant allyl amido pentaphene oxygroup cyclotrinitrile phosphide and preparation method thereof,
It is fire-retardant that the compound contains phosphorus, nitrogen dual element, can be used as unsaturated-resin, styrene, polyester, polyurethane, epoxy resin, poly- second
The fire retardant of enol and coating etc..
Background technique
Due to most high molecular materials be all it is inflammable, because its application caused by fire problem become very prominent
Out, so increasingly causing the common concern of people to the flame retardant treatment of material.Since the 1960s, to fire retardant
It researches and develops increasingly extensive.Various fire retardants and fire-retardant product emerge in large numbers rapidly.Since phosphorus, nitrogenated flame retardant have P-
The synergistic effect of N, flame-retarded efficiency are high.It not only has good flame retardant effect, and nontoxic, non-environmental-pollution, raw material sources are abundant,
It is that one kind has charcoal source, acid source, gas source three elements in the expansion type flame retardant of one, and a kind of environment friendly flame retardant.
Reactive flame retardant allyl amido pentaphene oxygroup cyclotrinitrile phosphide 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 environmental type fire retardant.And raw material is cheap and easy to get, has a wide range of application, application and development prospect in market is good.
Summary of the invention
It is an object of the present invention to propose a kind of three phosphonitrile chemical combination of reactive flame retardant allyl amido pentaphene oxygroup ring
Object, the compound have reactive allyl functional group, can be used as reactive flame retardant for the poly- of unsaturated-resin, styrene etc.
Conjunction obtains ingrain fireproofing resin, and fire retardant do not migrate, does not influence the mechanical property of material；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.Its physical and chemical performance is stablized, nontoxic, fire-retardant effect
Can be high, it is good with high molecular material compatibility, deficiency in the prior art can be overcome.
For achieving the above object, present invention employs following technical solutions:
A kind of reactive flame retardant allyl amido pentaphene oxygroup cyclotrinitrile phosphide, which is characterized in that the compound
Structure is shown below:
Another object of the present invention is to propose a kind of three phosphonitrile chemical combination of reactive flame retardant allyl amido pentaphene oxygroup ring
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, allylamine, phenol
And the molar ratio of acid binding agent is 1: 1: 5: 6 reactions, in the case where ice-water bath is cooling, allylamine 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 colorless and transparent
Three phosphonitrile of liquid allyl amido pentaphene oxygroup ring.
This method may be used also are as follows:
Hexachlorocyclotriph,sphazene is dissolved in organic solvent, equimolar acid binding agent is added, cooling lower dropwise addition of ice-water bath etc. rubs
Your allylamine reacts 1h；The phenol for adding 5 times moles of hexachlorocyclotriph,sphazene is warming up to 60~110 DEG C of 6~9h of reaction, until
No hydrogen chloride is released；30 DEG C are cooled to hereinafter, be evaporated under reduced pressure out organic solvent (recycling), adds relative product theory matter
The distilled water of amount 2~3 times of volumes ml of grams washes twice, and separates lower layer's organic phase, and relative product Theoretical Mass gram is added
The ethyl acetate of 2~3 times of volumes ml of number, is dried with anhydrous sodium sulfate, is filtered, and acetic acid second is distilled off in filtrate decompression
Ester obtains three phosphonitrile of colourless transparent liquid allyl amido pentaphene oxygroup ring.
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.
Reactive flame retardant allyl amido pentaphene oxygroup cyclotrinitrile phosphide of the invention is colourless transparent liquid, flash-point
(open cup): 189 ± 5 DEG C, density: 1.401g/cm3(25 DEG C), index of refraction: nD 25=1.3948.Yield be 89.2%~
95.6%, it can be used as unsaturated-resin, styrene, polyester, polyamide, polyurethane, epoxy resin, polyvinyl alcohol and coating etc.
Fire retardant.The preparation principle of the reactive flame retardant allyl amido pentaphene oxygroup cyclotrinitrile phosphide is shown below:
Compared with prior art, the invention has the beneficial effects that:
1. reactive flame retardant allyl amido pentaphene oxygroup cyclotrinitrile phosphide structure novel of the present invention, phosphorus content are
14.2%, nitrogen content 8.5%, ignition-proof element total content is 23.7%.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. reactive flame retardant allyl amido pentaphene oxygroup cyclotrinitrile phosphide 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. three phosphonitrile of reactive flame retardant allyl amido pentaphene oxygroup ring 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 three phosphonitrile of reactive flame retardant allyl amido pentaphene oxygroup ring 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 three phosphonitrile of reactive flame retardant allyl amido pentaphene oxygroup ring: Fig. 1 shows
3345cm-1For the stretching vibration peak of allyl amido N-H key；1589cm-1, 1487cm-1For the framework deformation absorption of vibrations on phenyl ring
Peak；And 3102cm-1For c h bond stretching vibration peak on phenyl ring；984cm-1For the absorption peak of P=N；1201cm-1For P-N absorption peak；
954cm-1For the absorption peak of P-O-C；1578cm-1For the stretching vibration peak of C=C double bond on allyl amido.
Fig. 2 is the nuclear magnetic spectrum figure of three phosphonitrile of reactive flame retardant allyl amido pentaphene oxygroup ring: Fig. 2 shows with deuterated
DMSO is CH at δ 1.25-1.40 as solvent2=CH-CH2The upper amido hydrogen peak-NH；It is CH at δ 3.25-3.322=CH-CH2-
The hydrogen peak of the upper methylene that is connected with amido of NH；It is CH at δ 4.94-5.132=CH-CH2The hydrogen peak of the upper double bond methylene of-NH；δ
It is CH at 5.88-6.012=CH-CH2The hydrogen peak of the upper-CH- of-NH；It is the hydrogen peak on phenyl ring at δ 6.42-6.97.
Fig. 3 is the thermal analysis curve figure of three phosphonitrile of reactive flame retardant allyl amido pentaphene oxygroup ring: Fig. 3 shows temperature
Start weightlessness for 293 DEG C of samples；Subsequent weight loss rate is accelerated, the weight-loss ratio 50% when temperature is 389 DEG C；Weightless speed after 600 DEG C
Rate flattens slow, illustrates that sample surface layer forms layer protecting film at this time, still there is 16% residue when to 800 DEG C of final temperature,
Illustrate 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 tri- suitable for reading equipped with drying tube
In mouthful bottle, with the air in nitrogen displacement bottle falling, addition 6.95g (0.02mol) hexachlorocyclotriph,sphazene, 120mL tetrahydrofuran,
12.12g (0.12mol) triethylamine, after stirring dissolves hexachlorocyclotriph,sphazene, cooling lower dropwise addition 1.14g (0.02mol) of ice-water bath
Allylamine controls temperature at 30 DEG C hereinafter, reaction 1h；9.40g (0.10mol) phenol is added, is warming up to 60 DEG C, reacts 7h；Drop
For temperature to 30 DEG C hereinafter, filtering the triethylamine hydrochloride for removing and generating, tetrahydrofuran (recycling) is distilled off in filtrate decompression, point
Not Jia Ru 25mL water washing twice, separate lower layer's organic phase, 20mL ethyl acetate be added, is dried with 1g anhydrous magnesium sulfate,
It filters, filtrate decompression is distilled off ethyl acetate, obtains three phosphonitrile of colourless transparent liquid allyl amido pentaphene oxygroup ring.Yield is
90.1%, flash-point (open cup): 189 ± 5 DEG C, density: 1.401g/cm3(25 DEG C), index of refraction: nD 25=1.3948.
Embodiment 2 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 acetonitrile, 12.12g is added
(0.12mol) triethylamine, after stirring dissolves hexachlorocyclotriph,sphazene, cooling lower dropwise addition 1.14g (0.02mol) allyl of ice-water bath
Amine controls temperature at 30 DEG C hereinafter, reaction 1h；9.40g (0.10mol) phenol is added, is warming up to 80 DEG C, reacts 6h；It is cooled to
30 DEG C hereinafter, the triethylamine hydrochloride that suction filtration removing generates, filtrate decompression are distilled off acetonitrile (recycling), are separately added into
25mL water washing twice, separates lower layer's organic phase, and 20mL ethyl acetate is added, is dried with 1g anhydrous magnesium sulfate, filters, filter
Liquid vacuum distillation removes ethyl acetate, obtains three phosphonitrile of colourless transparent liquid allyl amido pentaphene oxygroup ring.Yield is 92.7%, is dodged
Point (open cup): 189 ± 5 DEG C, density: 1.401g/cm3(25 DEG C), index of refraction: nD 25=1.3948.
Embodiment 3 is being equipped with blender, thermometer and condenser pipe, and in the condenser pipe 250mL tri- suitable for reading equipped with drying tube
In mouthful bottle, with the air in nitrogen displacement bottle falling, addition 6.95g (0.02mol) hexachlorocyclotriph,sphazene, 120mL dioxane,
14.52g (0.12mol) n,N-Dimethylaniline, after stirring dissolves hexachlorocyclotriph,sphazene, the cooling lower dropwise addition 1.14g of ice-water bath
(0.02mol) allylamine controls temperature at 30 DEG C hereinafter, reaction 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, dioxy is distilled off in filtrate decompression
Six rings (recycling), are separately added into 25mL water washing twice, separate lower layer's organic phase, and 20mL ethyl acetate is added, with 1g without
Water magnesium sulfate is dried, and filters, and filtrate decompression is distilled off ethyl acetate, obtains colourless transparent liquid allyl amido pentaphene oxygroup
Three phosphonitrile of ring.Yield is 95.6%, flash-point (open cup): 189 ± 5 DEG C, density: 1.401g/cm3(25 DEG C), index of refraction: nD 25
=1.3948.
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, 9.48g is added
(0.12mol) pyridine, after stirring dissolves hexachlorocyclotriph,sphazene, cooling lower dropwise addition 1.14g (0.02mol) allylamine of ice-water bath,
Temperature is controlled at 30 DEG C hereinafter, reaction 1h；9.40g (0.10mol) phenol is added, is warming up to 110 DEG C, reacts 4h；It is cooled to 30
DEG C hereinafter, filtering the pyridine hydrochloride for removing and generating, filtrate decompression is distilled off toluene (recycling), is separately added into 25mL water
It washes twice, separates lower layer's organic phase, 20mL ethyl acetate is added, is dried with 1g anhydrous magnesium sulfate, filter, filtrate decompression
Ethyl acetate is distilled off, obtains three phosphonitrile of colourless transparent liquid allyl amido pentaphene oxygroup ring.Yield is 93.0%, and flash-point (is opened
Cup): 189 ± 5 DEG C, density: 1.401g/cm3(25 DEG C), index of refraction: nD 25=1.3948.
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, catch up with the air in most bottle with nitrogen, be added 6.95g (0.02mol) hexachlorocyclotriph,sphazene,
120mL tetrahydrofuran and 2.02 (0.02mol) triethylamines, cooling lower dropwise addition 1.14g (0.02mol) allylamine of ice-water bath, control
Temperature is at 30 DEG C hereinafter, reaction 1h；9.40g (0.10mol) phenol is added, is warming up to 60 DEG C, 9h is reacted, until putting without hydrogen chloride
Out；30 DEG C are cooled to hereinafter, vacuum distillation removing tetrahydrofuran (recycling), is separately added into 25mL water washing twice, separates
Lower layer's organic phase is added 20mL ethyl acetate, is dried with 1g anhydrous magnesium sulfate, filters, and acetic acid is distilled off in filtrate decompression
Ethyl ester obtains three phosphonitrile of colourless transparent liquid allyl amido pentaphene oxygroup ring.Yield is 89.2%, flash-point (open cup): 189 ± 5
DEG C, density: 1.401g/cm3(25 DEG C), index of refraction: nD 25=1.3948.
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, catch up with the air in most bottle with nitrogen, be added 6.95g (0.02mol) hexachlorocyclotriph,sphazene,
120mL acetonitrile and 2.02 (0.02mol) triethylamines, cooling lower dropwise addition 1.14g (0.02mol) allylamine of ice-water bath, control temperature
At 30 DEG C hereinafter, reaction 1h；9.40g (0.10mol) phenol is added, is warming up to 80 DEG C, reacts 8h, until being released without hydrogen chloride；Drop
Temperature is to 30 DEG C hereinafter, vacuum distillation removing acetonitrile (recycling), is separately added into 25mL water washing twice, it is organic to separate lower layer
Phase is added 20mL ethyl acetate, is dried with 1g anhydrous magnesium sulfate, filters, and filtrate decompression is distilled off ethyl acetate, obtains nothing
Three phosphonitrile of color transparency liquid allyl amido pentaphene oxygroup ring.Yield is 91.6%, flash-point (open cup): 189 ± 5 DEG C, density:
1.401g/cm3(25 DEG C), index of refraction: nD 25=1.3948.
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, catch up with the air in most bottle with nitrogen, be added 6.95g (0.02mol) hexachlorocyclotriph,sphazene,
120mL dioxane and 2.42g (0.02mol) n,N-Dimethylaniline, cooling lower dropwise addition 1.14g (0.02mol) alkene of ice-water bath
Propylamine controls temperature at 30 DEG C hereinafter, reaction 1h；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, three phosphonitrile of colourless transparent liquid allyl amido pentaphene oxygroup ring is obtained.Yield is 94.3%, flash-point (open cup):
189 ± 5 DEG C, density: 1.401g/cm3(25 DEG C), index of refraction: nD 25=1.3948.
Embodiment 8 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, catch up with the air in most bottle with nitrogen, take 6.95g (0.02mol) hexachlorocyclotriph,sphazene,
120mL toluene and 1.58g (0.02mol) pyridine, cooling lower dropwise addition 1.14g (0.02mol) allylamine of ice-water bath, control temperature exist
30 DEG C hereinafter, reaction 1h；9.40g (0.10mol) phenol is added, is warming up to 110 DEG C, reacts 6h, until being released without hydrogen chloride；Cooling
To 30 DEG C hereinafter, vacuum distillation removes toluene (recycling), it is separately added into 25mL water washing twice, separates lower layer's organic phase,
20mL ethyl acetate is added, is dried with 1g anhydrous magnesium sulfate, filters, filtrate decompression is distilled off ethyl acetate, obtains colourless
Three phosphonitrile of transparency liquid allyl amido pentaphene oxygroup ring.Yield is 92.8%, flash-point (open cup): 189 ± 5 DEG C, density:
1.401g/cm3(25 DEG C), index of refraction: nD 25=1.3948.
1 preparation example main technologic parameters of table
Three phosphonitrile of reactive flame retardant allyl amido pentaphene oxygroup ring of above-mentioned synthesis is also applied to 191 by inventor
In unsaturated-resin, by three phosphonitrile of allyl amido pentaphene oxygroup ring 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 allyl amido pentaphene oxygroup ring of table, three phosphonitrile 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.As shown in Table 2 when
When mass fraction of three phosphonitrile of allyl amido pentaphene oxygroup ring in 191 unsaturated-resins is 20%, LOI 29；It thus can be with
Find out that three phosphonitrile of reactive flame retardant allyl amido pentaphene oxygroup ring has preferable flame-retarded efficiency to 191 unsaturated-resins.
Claims (5)
1. a kind of reactive flame retardant allyl amido pentaphene oxygroup cyclotrinitrile phosphide, which is characterized in that the knot of the compound
Structure is shown below:
2. the preparation side of reactive flame retardant allyl amido pentaphene oxygroup cyclotrinitrile phosphide 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, allylamine, 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, allylamine 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 colourless transparent liquid allyl amido five
Phenoxy cyclotriphosphazene.
3. the preparation side of reactive flame retardant allyl amido pentaphene oxygroup cyclotrinitrile phosphide according to claim 1
Method, which is characterized in that this method are as follows:
Hexachlorocyclotriph,sphazene is dissolved in organic solvent, equimolar acid binding agent is added, equimolar allyl is added dropwise under ice-water bath
Amine reacts 1h；The phenol for adding 5 times moles of hexachlorocyclotriph,sphazene is warming up to 60~110 DEG C of 6~9h of reaction, until without hydrogen chloride
It releases；30 DEG C are cooled to hereinafter, be evaporated under reduced pressure out organic solvent, adds 2~3 times of volumes millis of relative product Theoretical Mass grams
The distilled water for rising number washes twice, and separates lower layer's organic phase, and 2~3 times of volumes ml of relative product Theoretical Mass grams are added
Ethyl acetate, be dried, filtered, filtrate decompression is distilled off ethyl acetate, obtains colorless and transparent liquid with anhydrous sodium sulfate
Three phosphonitrile of body allyl amido pentaphene oxygroup ring.
4. according to the preparation of reactive flame retardant allyl amido pentaphene oxygroup cyclotrinitrile phosphide described in claim 2 and 3
Method, it is characterised in that: the acid binding agent is triethylamine, n,N-Dimethylaniline or pyridine.
5. according to the preparation of reactive flame retardant allyl amido pentaphene oxygroup cyclotrinitrile phosphide 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)
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| 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 CN201811568933.5A patent/CN109734748A/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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| Title |
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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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