CN109232978A - Fire retardant thiophosphoryl-(N, N ' ,-three young laying ducks in cage of N ") triamine compound and preparation method thereof - Google Patents
Fire retardant thiophosphoryl-(N, N ' ,-three young laying ducks in cage of N ") triamine compound and preparation method thereof Download PDFInfo
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- CN109232978A CN109232978A CN201811146069.XA CN201811146069A CN109232978A CN 109232978 A CN109232978 A CN 109232978A CN 201811146069 A CN201811146069 A CN 201811146069A CN 109232978 A CN109232978 A CN 109232978A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/5399—Phosphorus bound to nitrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65748—Esters of oxyacids of phosphorus the cyclic phosphorus atom belonging to more than one ring system
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
- C08K5/34928—Salts
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/02—Flame or fire retardant/resistant
Abstract
The present invention relates to a kind of fire retardant thiophosphoryl-(- three young laying ducks in cage of N, N ', N ") triamine compounds and preparation method thereof, and the structure of the compound is shown below:
Description
Technical field
The present invention relates to a kind of fire retardant thiophosphoryl-(- three young laying ducks in cage of N, N ', N ") triamine compound and its preparations
Method, and in particular to a kind of fire retardant thiophosphoryl three [N, N ', N "-three (1- oxygen -1- phospha -2,6,7- trioxa octyl < 4
>)] amine compounds and preparation method thereof, which is suitable as polyester, polyurethane, epoxy resin, unsaturated-resin, polychlorostyrene
The fire retardant of the materials such as ethylene.
Background technique
With the continuous development of global economy, inflammable high molecular material has obtained a large amount of application, while flame-retarded technology
Cracking development is obtained.Now widely used fire retardant has halogen system, phosphorus system, nitrogenated flame retardant etc..Halogenated flame retardant is from 20
It being just widely applied from the sixties in century, application technology is more mature, but possessed toxicity when due to burning, from
After European Union in 1986 promulgates RoHS instruction, the use of halogenated flame retardant is restricted in certain fields.Phosphorus nitrogen system especially has
Machine phosphorus-nitrogen containing flame retardant is gradually valued by people because it has many advantages, such as low cigarette, low toxicity, to organic phosphorus-nitrogen containing flame retardant
Research and development have become most promising one of direction.
The invention discloses it is a kind of containing phosphorus, nitrogen, sulphur ignition-proof element organic fire-retardant thiophosphoryl-(N, N ',
- three young laying ducks in cage of N ") triamine compound and preparation method thereof.The present invention is with stable young laying ducks in cage amine and phosphorus thiochloride
For raw material, one-step method prepares the compound, and simple process, equipment investment is few, easy to operate, at low cost, easy industrialized production；This
Invention fire retardant has many advantages, such as that the height of amount containing ignition-proof element, stable structure, flame-retarded efficiency are high, good with material compatibility, thus this
Invention fire retardant has extraordinary application and development prospect.
Summary of the invention
It is an object of the present invention to propose a kind of fire retardant thiophosphoryl-(- three young laying ducks in cage of N, N ', N ") triamine
Compound, physical and chemical performance is stablized, nontoxic, and flame-retarded efficiency is high, good with high molecular material compatibility, can overcome in the prior art
It is insufficient.
For achieving the above object, present invention employs following technical solutions:
A kind of fire retardant thiophosphoryl-(- three young laying ducks in cage of N, N ', N ") triamine compound, which is characterized in that the chemical combination
The structure of object is shown below:
Another object of the present invention is to propose that one kind has fire retardant thiophosphoryl-(- three young laying ducks in cage of N, N ', N ") three
The preparation method of amine compounds, this method are single step reaction, and simple process is easy to operate, and equipment investment is few, is easy to scale metaplasia
It produces.Its technical solution is as follows:
This method are as follows: with blender, thermometer, dropping funel, be connected to drying tube efficient backflow device reaction
In device, suitable organic solvent, young laying ducks in cage amine and triethylamine is added, catches up with the air in most bottle with nitrogen, under the conditions of 10 DEG C,
Phosphorus thiochloride is added dropwise in 1h, the certain molar ratio of control material limits dropping temperature at 10 DEG C~20 DEG C, after being added dropwise, rises
Temperature is to 80-110 DEG C of insulation reaction 3-5h, and cold filtration, vacuum drying obtain the target product and triethylamine hydrochloride of yellow later
Solid mixture, dissolve purpose product with suitable dimethyl sulfoxide, filtering, filtrate is evaporated, and obtains target product thiophosphoryl-
(- three young laying ducks in cage of N, N ', N ") triamine.
It is tetrachloroethanes, dioxane, acetonitrile, dichloroethanes diethylene glycol that suitable organic solvent is added as described above
Dimethyl ether or ethylene glycol diethyl ether, dosage volume ml are 10-20 times of young laying ducks in cage amine grams.
The certain molar ratio of control material as described above is phosphorus thiochloride: young laying ducks in cage amine: triethylamine=1: 3: 3-1
∶3.4∶3。
Suitable dimethyl sulfoxide as described above is that the volume ml of addition dimethyl sulfoxide is the 10- of product theory grams
20 times.
Young laying ducks in cage amine as described above is 1- oxygen -1- phospha -2,6,7- trioxa octyl<4>amine, structural formula
Are as follows:
Organic phosphine fire retardant thiophosphoryl-(- three young laying ducks in cage of N, N ', N ") triamine of the present invention is yellow solid, product
Yield is 87.3%-93.3%, decomposition temperature: 264 DEG C.It is suitable as polyester, polyurethane, epoxy resin, unsaturated-resin,
The preparation process of the fire retardant of the materials such as polyvinyl chloride, polyvinyl acetate, the double phosphinylidyne young laying ducks in cage of the organic phosphine fire retardant is former
Reason is shown below:
Compared with prior art, the beneficial effects of the present invention are:
(1) fire retardant thiophosphoryl-(- three young laying ducks in cage of N, N ', N ") triamine compound of the present invention contains phosphorus sulphur nitrogen three
Kind ignition-proof element, effective ignition-proof element content is high, and mutual cooperative flame retardant efficiency is high, and cage ring structural symmetry is good, stable structure,
Decomposition temperature is high, there is preferable processing performance.
(2) the raw material cage that fire retardant thiophosphoryl-(- three young laying ducks in cage of N, N ', N ") triamine compound of the present invention uses
Inherently a kind of excellent response type organic phosphine fire retardant of shape phosphoric acid ester amine, stable structure are reacted with phosphorus thiochloride, and are improved
The content of phosphorus, also introduces effective ignition-proof element sulphur, forms multiamide polyester structure, assign product and material have compared with
Good compatibility and fire retardation.
(3) fire retardant thiophosphoryl-(- three young laying ducks in cage of N, N ', N ") triamine compound of the present invention has with MCA and MPP
Compounding synergistic function well provides beneficial support to improving the performance for improving fire proofing and reducing cost.
(4) preparation of organic phosphine fire retardant thiophosphoryl-(- three young laying ducks in cage of N, N ', N ") triamine compound of the present invention
Method is single step reaction, and simple process, equipment investment is few, easy to operate, at low cost, is easy to scale conversion and production.
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 thiophosphoryl-(- three young laying ducks in cage of N, N ', N ") triamine；
Fig. 1 shows 1650cm-1Place is N-H stretching vibration peak, 1481.01cm-1Place is the P=O key on N-P=S key
Flexural vibrations peak, 1399.35cm-1Place is the flexural vibrations peak of the P=O key of key on O-P=O, 1079.06cm-1Place is P-O-
C stretching vibration peak, 976.02cm-1、624.59cm-1、516.16cm-1For the characteristic absorption peak of cyclic structure.
Fig. 2 is the nuclear magnetic spectrum figure of thiophosphoryl-(- three young laying ducks in cage of N, N ', N ") triamine；
Fig. 2 shows with deuterated water as solvent, is the peak H on-NH- at chemical shift δ 2.60；δ 4.36 is-CH2H
Peak.
Specific embodiment
Below in conjunction with specific embodiment, technical scheme is described further.
Embodiment 1 with blender, thermometer, dropping funel, connect drying tube high performance reflux condenser 250ml tetra-
In mouthful bottle, 80ml acetonitrile, 4.95g young laying ducks in cage amine and 3.03g triethylamine is added, catches up with the air in most bottle with nitrogen, 10 DEG C
Under the conditions of, it being added drop-wise in reaction flask in 1.70g phosphorus thiochloride 1h, control dropping temperature is at 10 DEG C~20 DEG C, after being added dropwise,
80 DEG C of insulation reaction 3h are warming up to, are then cooled to 20 DEG C, are filtered, vacuum drying obtains the product and triethylamine hydrochloride of yellow
Solid mixture.Solid mixture with 60ml dimethyl sulfoxide dissolve, filtering, filtrate be evaporated the thio phosphorus phosphinylidyne-of product (N,
- three young laying ducks in cage of N ', N ") triamine.Yield is 87.3%, and decomposition temperature is 264 DEG C.
Embodiment 2 with blender, thermometer, dropping funel, connect drying tube high performance reflux condenser 250ml tetra-
In mouth bottle, 90ml dioxane, 4.95g young laying ducks in cage amine and 3.03g triethylamine is added, catches up with the air in most bottle with nitrogen,
It under the conditions of 10 DEG C, will be added drop-wise in reaction flask in 1.70g phosphorus thiochloride 1h, control dropping temperature at 10 DEG C~20 DEG C, drip
Bi Hou is warming up to 90 DEG C of insulation reaction 3h, is then cooled to 20 DEG C, filters, and vacuum drying obtains the product and triethylamine salt of yellow
The solid mixture of hydrochlorate.Solid mixture 70ml dimethyl sulfoxide dissolves, and filtering, filtrate is evaporated to obtain the thio phosphorus phosphinylidyne-of product
(- three young laying ducks in cage of N, N ', N ") triamine.Yield is 90.1%, and decomposition temperature is 264 DEG C.
Embodiment 3 with blender, thermometer, dropping funel, connect drying tube high performance reflux condenser 250ml tetra-
In mouth bottle, 90ml diethylene glycol dimethyl ether, 4.95g young laying ducks in cage amine and 3.03g triethylamine is added, is caught up in most bottle with nitrogen
Air under the conditions of 10 DEG C, will be added drop-wise in reaction flask in 1.70g phosphorus thiochloride 1h, control dropping temperature at 10 DEG C~20 DEG C, drop
After adding, 100 DEG C of insulation reaction 4h are warming up to, are then cooled to 20 DEG C, are filtered, vacuum drying obtains the product and three of yellow
The solid mixture of ethylamine hydrochloride.Solid mixture 80ml dimethyl sulfoxide dissolves, and filtering, filtrate is evaporated to obtain the thio phosphorus of product
Acyl-(- three young laying ducks in cage of N, N ', N ") triamine.Yield is 91.5%, and decomposition temperature is 264 DEG C.
Embodiment 4 with blender, thermometer, dropping funel, connect drying tube high performance reflux condenser 250ml tetra-
In mouth bottle, 100ml dichloroethanes, 4.95g young laying ducks in cage amine and 3.03g triethylamine is added, catches up with the air in most bottle with nitrogen,
It under the conditions of 10 DEG C, will be added drop-wise in reaction flask in 1.70g phosphorus thiochloride 1h, control dropping temperature at 10 DEG C~20 DEG C, drip
Bi Hou is warming up to 80 DEG C of insulation reaction 5h, is then cooled to 20 DEG C, filters, and vacuum drying obtains the product and triethylamine salt of yellow
The solid mixture of hydrochlorate.Solid mixture with 90ml dimethyl sulfoxide dissolve, filtering, filtrate be evaporated product thiophosphoryl-(N,
- three young laying ducks in cage of N ', N ") triamine.Yield is 91.0%, and decomposition temperature is 264 DEG C.
Embodiment 5 with blender, thermometer, dropping funel, connect drying tube high performance reflux condenser 250ml tetra-
In mouth bottle, 90ml ethylene glycol diethyl ether, 4.95g young laying ducks in cage amine and 3.03g triethylamine is added, catches up with the sky in most bottle with nitrogen
Gas under the conditions of 10 DEG C, will be added drop-wise in reaction flask in 1.70g phosphorus thiochloride 1h, is controlled dropping temperature at 10 DEG C~20 DEG C, is added dropwise
After, 90 DEG C of insulation reaction 5h are warming up to, are then cooled to 20 DEG C, are filtered, vacuum drying obtains the product and triethylamine of yellow
The solid mixture of hydrochloride.Solid mixture 100ml dimethyl sulfoxide dissolves, and filtering, filtrate is evaporated to obtain product thiophosphoryl-
(- three young laying ducks in cage of N, N ', N ") triamine.Yield is 92.2%, and decomposition temperature is 264 DEG C.
Embodiment 6 with blender, thermometer, dropping funel, connect drying tube high performance reflux condenser 250ml tetra-
In mouth bottle, 110ml tetrachloroethanes, 4.95g young laying ducks in cage amine and 3.03g triethylamine is added, catches up with the air in most bottle with nitrogen,
It under the conditions of 10 DEG C, will be added drop-wise in reaction flask in 1.70g phosphorus thiochloride 1h, control dropping temperature at 10 DEG C~20 DEG C, drip
Bi Hou is warming up to 110 DEG C of insulation reaction 4h, is then cooled to 20 DEG C, filters, and vacuum drying obtains the product and triethylamine of yellow
The solid mixture of hydrochloride.Solid mixture 60ml dimethyl sulfoxide dissolves, and filtering, filtrate is evaporated to obtain the thio phosphorus phosphorus of product
Acyl-(- three young laying ducks in cage of N, N ', N ") triamine.Yield is 89.3%, and decomposition temperature is 264 DEG C.
Embodiment 7 with blender, thermometer, dropping funel, connect drying tube high performance reflux condenser 250ml tetra-
In mouthful bottle, 80ml acetonitrile, 5.12g young laying ducks in cage amine and 3.03g triethylamine is added, catches up with the air in most bottle with nitrogen, 10 DEG C
Under the conditions of, it being added drop-wise in reaction flask in 1.70g phosphorus thiochloride 1h, control dropping temperature is at 10 DEG C~20 DEG C, after being added dropwise,
80 DEG C of insulation reaction 4h are warming up to, are then cooled to 20 DEG C, are filtered, vacuum drying obtains the product and triethylamine hydrochloride of yellow
Solid mixture.Solid mixture with 70ml dimethyl sulfoxide dissolve, filtering, filtrate be evaporated product thiophosphoryl-(N, N ',
- three young laying ducks in cage of N ") triamine.Yield is 90.4%, and decomposition temperature is 264 DEG C.
Embodiment 8 with blender, thermometer, dropping funel, connect drying tube high performance reflux condenser 250ml tetra-
In mouth bottle, 90ml diethylene glycol dimethyl ether, 5.33g young laying ducks in cage amine and 3.03g triethylamine is added, is caught up in most bottle with nitrogen
Air under the conditions of 10 DEG C, will be added drop-wise in reaction flask in 1.70g phosphorus thiochloride 1h, control dropping temperature at 10 DEG C~20 DEG C, drop
After adding, 100 DEG C of insulation reaction 4h are warming up to, are then cooled to 20 DEG C, are filtered, vacuum drying obtains the product and three of yellow
The solid mixture of ethylamine hydrochloride.Solid mixture 80ml dimethyl sulfoxide dissolves, and filtering, filtrate is evaporated to obtain the thio phosphorus of product
Acyl-(- three young laying ducks in cage of N, N ', N ") triamine.Yield is 91.9%, and decomposition temperature is 264 DEG C.
Embodiment 9 with blender, thermometer, dropping funel, connect drying tube high performance reflux condenser 250ml tetra-
In mouth bottle, 100ml dichloroethanes, 5.45g young laying ducks in cage amine and 3.03g triethylamine is added, catches up with the air in most bottle with nitrogen,
It under the conditions of 10 DEG C, will be added drop-wise in reaction flask in 1.70g phosphorus thiochloride 1h, control dropping temperature at 10 DEG C~20 DEG C, drip
Bi Hou is warming up to 80 DEG C of insulation reaction 4h, is then cooled to 20 DEG C, filters, and vacuum drying obtains the product and triethylamine salt of yellow
The solid mixture of hydrochlorate.Solid mixture with 90ml dimethyl sulfoxide dissolve, filtering, filtrate be evaporated product thiophosphoryl-(N,
- three young laying ducks in cage of N ', N ") triamine.Yield is 92.0%, and decomposition temperature is 264 DEG C.
Embodiment 10 with blender, thermometer, dropping funel, connect drying tube high performance reflux condenser 250ml
In four-hole bottle, 90ml dioxane, 5.61g young laying ducks in cage amine and 3.03g triethylamine is added, catches up with the sky in most bottle with nitrogen
Gas under the conditions of 10 DEG C, will be added drop-wise in reaction flask in 1.70g phosphorus thiochloride 1h, is controlled dropping temperature at 10 DEG C~20 DEG C, is added dropwise
After, 90 DEG C of insulation reaction 4h are warming up to, are then cooled to 20 DEG C, are filtered, vacuum drying obtains the product and triethylamine of yellow
The solid mixture of hydrochloride.Solid mixture 100ml dimethyl sulfoxide dissolves, and filtering, filtrate is evaporated to obtain product thiophosphoryl-
(- three young laying ducks in cage of N, N ', N ") triamine.Yield is 93.3%, and decomposition temperature is 264 DEG C.
Table 1 prepares embodiment main technologic parameters
The product thiophosphoryl-of above-mentioned preparation (- three young laying ducks in cage of N, N ', N ") triamine is also applied to by inventor
In polyester PBT.Reference: the limit oxygen of GB/T2406-2008 " Plastics Combustion method for testing performance-oxygen index method " sample refers to
Number.The product of different proportion is added in PBT, or after product is compounded in different proportions with MCA, MPP, then with different ratios
Example is added in PBT, at 230 DEG C, is squeezed out with extruder, and a length of 15cm is made, and diameter is the batten of 3mm, and fire-retardant to its
Performance is tested, and the LOI result measured is as shown in Table 2-4:
2 thiophosphoryl of table-(- three young laying ducks in cage of N, N ', N ") triamine is for the fire-retardant data in PBT
| Additive amount % | LOI% | Drip situation | At charcoal |
| 0 | 20 | Fast drippage | Not at charcoal |
| 10 | 22 | Fast drippage | Not at charcoal |
| 20 | 28 | Slow drippage | At charcoal |
| 25 | 30 | Slow drippage | At charcoal |
As shown in Table 2, when phenyl time two (bis- cage phosphate of N, N-) additive amount of the amine in PBT of phosphinylidyne is 20%, pole
Limiting oxygen index value is 28%, has had reached fire retardant rank, though there is slight drippage, carbon-forming performance is fine.
3 product thiophosphoryl of table-(- three young laying ducks in cage of N, N ', N ") triamine and MCA compounding are for the fire-retardant number in PBT
According to
As shown in Table 3, product thiophosphoryl-(- three young laying ducks in cage of N, N ', N ") triamine has compounded preferable association with MCA
Same-action, there are also good dilatancy, optimal additive amount proportion is 3: 2, and when total addition level is 25%, limit oxygen index can
Up to 31%, illustrate that system has become nonflammable material at this time after compounding, and does not drip, and fine at charcoal, and the price of MCA is very
It is cheap, the production cost of fire proofing can be greatly lowered.Thus it can be seen that product thiophosphoryl-(- three caged of N, N ', N "
Phosphate) no matter triamine is single use, or compounds with MCA, there is preferable flame retardant effect to PBT material.
4 product thiophosphoryl of table-(- three young laying ducks in cage of N, N ', N ") triamine and MPP compounding are for the fire-retardant number in PBT
According to
As shown in Table 4, optimal additive amount proportion is 1: 1 after the compounding of the nitrogen phosphorus expansion type flame retardant product and MPP, pole
Limiting oxygen index value illustrates that system has formd nonflammable material at this time after compounding, but has the appearance of slight molten drop up to 28%.
It thus it can be seen that no matter product is single use, or is compounded with MPP, MCA, good anti-flammability is all had to PBT resin
Energy.
Claims (5)
1. a kind of fire retardant thiophosphoryl-(- three young laying ducks in cage of N, N ', N ") triamine compound, which is characterized in that the compound
Structure be shown below:
2. a kind of fire retardant thiophosphoryl-(- three young laying ducks in cage of N, N ', N ") triamine compound according to claim 1
Preparation method, which is characterized in that this method are as follows:
With blender, dropping funel, thermometer, be connected to drying tube the reactor of efficient backflow device in, be added appropriate
Organic solvent, young laying ducks in cage amine and triethylamine, catch up with the air in most bottle with nitrogen, under the conditions of 10 DEG C, trichlorine be added dropwise in 1h
Sulphur phosphorus, the certain molar ratio of control material limit dropping temperature at 10 DEG C~20 DEG C, after being added dropwise, are warming up to 80-110 DEG C
Insulation reaction 3-5h, cold filtration, vacuum drying, the target product for obtaining yellow are mixed with the solid of triethylamine hydrochloride later
Object dissolves purpose product, filtering with suitable dimethyl sulfoxide, and filtrate is evaporated, and obtains target product thiophosphoryl-(N, N ', N "-three
Young laying ducks in cage) triamine；Young laying ducks in cage amine as described above is 1- oxygen -1- phospha -2,6,7- trioxa octyl<4>amine,
Its structural formula are as follows:
3. a kind of fire retardant thiophosphoryl-(- three young laying ducks in cage of N, N ', N ") triamine compound according to claim 2
Preparation method, which is characterized in that the suitable organic solvent of the addition be tetrachloroethanes, dioxane, acetonitrile, two chloroethenes
Alkane diethylene glycol dimethyl ether or ethylene glycol diethyl ether, dosage volume ml are 10-20 times of young laying ducks in cage amine grams.
4. a kind of fire retardant thiophosphoryl-(- three young laying ducks in cage of N, N ', N ") triamine compound according to claim 2
Preparation method, which is characterized in that the certain molar ratio of control material as described above is phosphorus thiochloride: young laying ducks in cage amine:
Triethylamine=1: 3: 3-1: 3.4: 3.
5. a kind of fire retardant thiophosphoryl-(- three young laying ducks in cage of N, N ', N ") triamine compound according to claim 2
Preparation method, which is characterized in that as described above with suitable dimethyl sulfoxide be added dimethyl sulfoxide volume ml be
10-20 times of product theory grams.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111978351A (en) * | 2020-08-06 | 2020-11-24 | 苏州科技大学 | Fire retardant cage-shaped organic silicon phosphoramide compound and preparation method thereof |
| CN114315896A (en) * | 2021-12-09 | 2022-04-12 | 湖北大学 | 2- (diphenyl thiophosphoryl) succinate and synthesis method and application thereof |
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| 孙志松: "环状磷酸酯无卤阻燃剂的合成与表征", 《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》 * |
| 彭华乔: "不同结构的双环笼状含磷阻燃剂的合成及其在聚丙烯阻燃改性中的应用", 《中国博士学位论文全文数据库 工程科技Ⅰ辑》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111978351A (en) * | 2020-08-06 | 2020-11-24 | 苏州科技大学 | Fire retardant cage-shaped organic silicon phosphoramide compound and preparation method thereof |
| CN111978351B (en) * | 2020-08-06 | 2022-04-26 | 苏州科技大学 | Fire retardant cage-shaped organic silicon phosphoramide compound and preparation method thereof |
| CN114315896A (en) * | 2021-12-09 | 2022-04-12 | 湖北大学 | 2- (diphenyl thiophosphoryl) succinate and synthesis method and application thereof |
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Application publication date: 20190118 |