CN109180731A - Organic phosphine nitrogen combustion inhibitor diphenyl Asia phosphono-N- young laying ducks in cage amine compounds and preparation method thereof - Google Patents
Organic phosphine nitrogen combustion inhibitor diphenyl Asia phosphono-N- young laying ducks in cage amine compounds and preparation method thereof Download PDFInfo
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- CN109180731A CN109180731A CN201811145923.0A CN201811145923A CN109180731A CN 109180731 A CN109180731 A CN 109180731A CN 201811145923 A CN201811145923 A CN 201811145923A CN 109180731 A CN109180731 A CN 109180731A
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- 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
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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
- C08K5/16—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
- C08K5/34924—Triazines containing cyanurate groups; Tautomers thereof
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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
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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
- C08L2201/00—Properties
- C08L2201/02—Flame or fire retardant/resistant
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- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Fireproofing Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The present invention relates to a kind of organic phosphine nitrogen combustion inhibitor diphenyl Asia phosphono-N- young laying ducks in cage amine 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 organic phosphine nitrogen combustion inhibitor diphenyl Asia phosphono-N- young laying ducks in cage amine compounds and its preparations
A kind of method, and in particular to diphenyl Asia phosphono-N-1- oxygen -1- phospha -2,6,7- trioxa octyl<4>compound and its system
Preparation Method, the compound are suitable as the materials such as polyamide, polyester, polyurethane, epoxy resin, unsaturated-resin, polyolefin
Fire retardant.
Background technique
As being constantly progressive of social economy, the development of flame-retarded technology, fire retardant and flame retarded polymeric material subtract in prevention
Important role has been given full play in terms of few fire.With the continuous improvement of people's living standards, to high-performance flame-retardant material
Demand is also higher and higher.Currently, although flame-retarded technology has obtained quick development, fire retardant no matter kind and quantity it is all very rich
Richness, but be not met by the growing demand of people, while and developed countries there is also a certain distance.
The invention discloses a kind of organic phosphine nitrogen combustion inhibitor diphenyl Asia phosphono-N- young laying ducks in cage amine compounds and its systems
Preparation Method.The present invention is using stable young laying ducks in cage amine and diphenyl phosphorus chloride as raw material, and one-step method prepares the compound, work
Skill is simple, and equipment investment is few, easy to operate, at low cost, is easily converted into industrialized production；Fire retardant of the present invention has phosphorus content
High, the advantages that stability is good, flame-retarded efficiency is high, good with material compatibility, therefore, before fire retardant of the present invention has extraordinary application
Scape.
Summary of the invention
It is an object of the present invention to propose a kind of organic phosphine nitrogen combustion inhibitor diphenyl Asia phosphono-N- young laying ducks in cage amine
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 organic phosphine nitrogen combustion inhibitor diphenyl
Sub- phosphono-N- young laying ducks in cage amine compounds, which is characterized in that the structure of the compound is shown below:
Another object of the present invention is to propose a kind of organic phosphine nitrogen combustion inhibitor diphenyl Asia phosphono-N- young laying ducks in cage amine
The preparation method of compound, 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:
Equipped with blender, thermometer, dropping funel, be connected to drying tube efficient backflow condensing unit reactor, add
Enter appropriate organic solvent, young laying ducks in cage amine and triethylamine, catch up with the air in reactor with nitrogen, at 20 °C, starts
Diphenyl phosphine chloride is added dropwise, is not higher than 50 DEG C with rate of addition control drip reacting temperature, the molar ratio for controlling reaction mass is
Diphenyl phosphine chloride: young laying ducks in cage amine: triethylamine=1: 1: 1-1: 1.2: 1,80-110 DEG C of reflux is warming up to after being added dropwise
4-6h is reacted, cold filtration, is washed with water later, is dried in vacuo to obtain yellowish solid diphenyl Asia phosphono-N- young laying ducks in cage
Amine.
A certain amount of organic solvent as described above be methyl phenyl ethers anisole, dioxane, diethylene glycol dimethyl ether, dichloroethanes or
Acetonitrile, dosage volume ml are 10-15 times of young laying ducks in cage amine quality grams.
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 of the present invention but fire retardant diphenyl Asia phosphono-N- young laying ducks in cage amine are yellowish solid, product yield
For 90.4%-90.4%, decomposition temperature: 292 ± 5 DEG C DEG C.It is suitable as polyamide, polyester, polyurethane, epoxy resin, no
The fire retardant of the materials such as saturated resin, polyolefin, the system of the organic phosphine nitrogen combustion inhibitor diphenyl Asia phosphono-N- young laying ducks in cage amine
Standby technological principle is shown below:
Compared with prior art, the beneficial effects of the present invention are:
(1) organic phosphine nitrogen combustion inhibitor diphenyl Asia phosphono-N- young laying ducks in cage amine compounds phosphorus content of the present invention is high, fire-retardant
Efficiency is high, and cage ring structural symmetry is good, and product is stablized, and decomposition temperature is high, there is preferable processing performance.
(2) the raw material cage that phosphono-N- young laying ducks in cage amine compounds in organic phosphine nitrogen combustion inhibitor diphenyl Asia of the present invention use
Inherently a kind of excellent response type organic phosphine fire retardant of shape phosphoric acid ester amine, stable structure are reacted with diphenyl phosphine chloride, again
The content for improving phosphorus also introduces the benzene ring structure with electronic structure to change, and assigning product and material has preferable phase
Capacitive.
(3) organic phosphine nitrogen combustion inhibitor diphenyl Asia phosphono-N- young laying ducks in cage amine compounds of the present invention and MCA and MPP are multiple
It is especially more significant with cheap MCA compounding effect with producing good synergistic function, to reducing fire proofing
The physical and chemical performance meaning of cost improvement material is bigger.
(4) preparation method one of phosphono-N- young laying ducks in cage amine compounds in organic phosphine nitrogen combustion inhibitor diphenyl Asia of the present invention
Step reaction, 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 diphenyl Asia phosphono-N- young laying ducks in cage amine；Fig. 1 shows in 3418.08cm-1Place is
N-H stretching vibration peak, 1472.25cm-1Place is the stretching vibration peak of P-Ph key, 1435.15cm-1Place is phenyl ring in plane vibration peak,
848.51cm-1Place is P-O-C stretching vibration peak, 804.01cm-1、616.53cm-1、504.72cm-1For the feature of cyclic structure
Absorption peak.
Fig. 2 is the nuclear magnetic spectrum figure of diphenyl Asia phosphono-N- young laying ducks in cage amine；Fig. 2 shows with deuterated water as solvent,
It is the peak H of-NH- at chemical shift δ 2.12；δ 4.20 is-CH2On the peak H, δ 7.26 be the peak phenyl H.
Body embodiment
Below in conjunction with specific embodiment, technical scheme is described further.
Embodiment 1 is equipped with blender, thermometer, dropping funel, the high performance reflux condenser for being connected to drying tube
In 250ml four-hole bottle, 100ml dichloroethanes, 6.60g young laying ducks in cage amine and 4.05g triethylamine is added, is caught up in most bottle with nitrogen
Air, start at 20 DEG C that 8.83g diphenyl phosphine chloride is added dropwise, make to control reaction temperature with rate of addition and be no more than 50 DEG C, drop
It is warming up to 80 DEG C of back flow reaction 4h after adding, is then cooled to 20 DEG C, filtering is washed with water, is dried in vacuo yellowish solid
Body hexichol Asia phosphono-N- young laying ducks in cage amine.Yield is 86.7%.Decomposition temperature is 292 ± 5 DEG C.
Embodiment 2 is equipped with blender, thermometer, dropping funel, the high performance reflux condenser for being connected to drying tube
In 250ml four-hole bottle, 80ml dioxane, 6.60g young laying ducks in cage amine and 4.05g triethylamine is added, is caught up in most bottle with nitrogen
Air, start at 20 DEG C that 8.83g diphenyl phosphine chloride is added dropwise, make to control reaction temperature with rate of addition and be no more than 50 DEG C, drop
It is warming up to 100 DEG C of back flow reaction 4h after adding, is then cooled to 20 DEG C, filtering is washed with water, is dried in vacuo yellowish solid
Body diphenyl Asia phosphono-N- young laying ducks in cage amine.Yield is 88.5%.Decomposition temperature is 292 ± 5 DEG C.
Embodiment 3 is equipped with blender, thermometer, dropping funel, the high performance reflux condenser for being connected to drying tube
In 250ml four-hole bottle, 90ml diethylene glycol dimethyl ether, 6.60g young laying ducks in cage amine and 4.05g triethylamine is added, is caught up with nitrogen
The air in bottle is use up, starts that 8.83g diphenyl phosphine chloride is added dropwise at 20 DEG C, makes to control reaction temperature no more than 50 with rate of addition
DEG C, it is warming up to 100 DEG C of back flow reaction 5h after being added dropwise, is then cooled to 20 DEG C, filtering is washed with water, is dried in vacuo micro-
Yellow solid diphenyl Asia phosphono-N- young laying ducks in cage amine.Yield is 89.5%.Decomposition temperature is 292 ± 5 DEG C.
Embodiment 4 is equipped with blender, thermometer, dropping funel, the high performance reflux condenser for being connected to drying tube
In 250ml four-hole bottle, 70ml methyl phenyl ethers anisole, 6.60g young laying ducks in cage amine and 4.05g triethylamine is added, is caught up in most bottle with nitrogen
Air starts at 20 DEG C that 8.83g diphenyl phosphine chloride is added dropwise, and makes to control reaction temperature with rate of addition and is no more than 50 DEG C, is added dropwise
After be warming up to 90 DEG C of back flow reaction 6h, be then cooled to 20 DEG C, filtering is washed with water, is dried in vacuo to obtain yellowish solid
Diphenyl Asia phosphono-N- young laying ducks in cage amine.Yield is 88.6%.Decomposition temperature is 292 ± 5 DEG C.
Embodiment 5 is equipped with blender, thermometer, dropping funel, the high performance reflux condenser for being connected to drying tube
In 250ml four-hole bottle, 100ml dioxane, 6.60g young laying ducks in cage amine and 4.05g triethylamine is added, is caught up in most bottle with nitrogen
Air, start at 20 DEG C that 8.83g diphenyl phosphine chloride is added dropwise, make to control reaction temperature with rate of addition and be no more than 50 DEG C, drop
It is warming up to 100 DEG C of back flow reaction 6h after adding, is then cooled to 20 DEG C, filtering is washed with water, is dried in vacuo yellowish solid
Body diphenyl Asia phosphono-N- young laying ducks in cage amine.Yield is 90.0%.Decomposition temperature is 292 ± 5 DEG C.
Embodiment 6 is equipped with blender, thermometer, dropping funel, the high performance reflux condenser for being connected to drying tube
In 250ml four-hole bottle, 100ml acetonitrile, 6.60g young laying ducks in cage amine and 4.05g triethylamine is added, catches up with the sky in most bottle with nitrogen
Gas starts at 20 DEG C that 8.83g diphenyl phosphine chloride is added dropwise, and makes to control reaction temperature with rate of addition and is no more than 50 DEG C, drips
80 DEG C of back flow reaction 5h are warming up to after finishing, are then cooled to 20 DEG C, filtering is washed with water, is dried in vacuo to obtain yellowish solid two
Phenyl Asia phosphono-N- young laying ducks in cage amine.Yield is 87.9%.Decomposition temperature is 292 ± 5 DEG C.
Embodiment 7 is equipped with blender, thermometer, dropping funel, the high performance reflux condenser for being connected to drying tube
In 250ml four-hole bottle, 90ml methyl phenyl ethers anisole, 6.60g young laying ducks in cage amine and 4.05g triethylamine is added, is caught up in most bottle with nitrogen
Air starts at 20 DEG C that 8.83g diphenyl phosphine chloride is added dropwise, and makes to control reaction temperature with rate of addition and is no more than 50 DEG C, is added dropwise
After be warming up to 110 DEG C of back flow reaction 5h, be then cooled to 20 DEG C, filtering is washed with water, is dried in vacuo to obtain yellowish solid
Diphenyl Asia phosphono-N- young laying ducks in cage amine.Yield is 89.3%.Decomposition temperature is 292 ± 5 DEG C.
Embodiment 8 is equipped with blender, thermometer, dropping funel, the high performance reflux condenser for being connected to drying tube
In 250ml four-hole bottle, 100ml diethylene glycol dimethyl ether, 6.60g young laying ducks in cage amine and 4.05g triethylamine is added, is caught up with nitrogen
The air in bottle is use up, starts that 8.83g diphenyl phosphine chloride is added dropwise at 20 DEG C, makes to control reaction temperature no more than 50 with rate of addition
DEG C, it is warming up to 110 DEG C of back flow reaction 5h after being added dropwise, is then cooled to 20 DEG C, filtering is washed with water, is dried in vacuo micro-
Yellow solid diphenyl Asia phosphono-N- young laying ducks in cage amine.Yield is 91.0%.Decomposition temperature is 292 ± 5 DEG C.
Embodiment 9 is equipped with blender, thermometer, dropping funel, the high performance reflux condenser for being connected to drying tube
In 250ml four-hole bottle, 900ml acetonitrile, 6.60g young laying ducks in cage amine and 4.05g triethylamine is added, catches up with the sky in most bottle with nitrogen
Gas starts at 20 DEG C that 8.83g diphenyl phosphine chloride is added dropwise, and makes to control reaction temperature with rate of addition and is no more than 50 DEG C, drips
80 DEG C of back flow reaction 5h are warming up to after finishing, are then cooled to 20 DEG C, filtering is washed with water, is dried in vacuo to obtain yellowish solid two
Phenyl Asia phosphono-N- young laying ducks in cage amine.Yield is 90.1%.Decomposition temperature is 292 ± 5 DEG C.
Embodiment 10 is equipped with blender, thermometer, dropping funel, the high performance reflux condenser for being connected to drying tube
In 250ml four-hole bottle, 90ml dioxane, 6.60g young laying ducks in cage amine and 4.05g triethylamine is added, is caught up in most bottle with nitrogen
Air, start at 20 DEG C that 8.83g diphenyl phosphine chloride is added dropwise, make to control reaction temperature with rate of addition and be no more than 50 DEG C, drop
It is warming up to 100 DEG C of back flow reaction 5h after adding, is then cooled to 20 DEG C, filtering is washed with water, is dried in vacuo yellowish solid
Body diphenyl Asia phosphono-N- young laying ducks in cage amine.Yield is 92.0%.Decomposition temperature is 292 ± 5 DEG C.
Table 1 prepares embodiment main technologic parameters
The product diphenyl Asia phosphono-N- young laying ducks in cage amine of above-mentioned preparation is also applied to polyester PBT by inventor
In.Reference: the limit oxygen index of GB/T2406-2008 " Plastics Combustion method for testing performance-oxygen index method " sample.In PBT
The middle product that different proportion is added, or after product is compounded in different proportions with MCA, MPP, then be added in different proportions
It in PBT, at 230 DEG C, is squeezed out with extruder, a length of 15cm is made, diameter is the batten of 3mm, and carries out to its flame retardant property
Test, the LOI result that measures are as shown in Table 2-4:
2 diphenyl Asia phosphono-N- young laying ducks in cage amine of table is for the fire-retardant data in PBT
| Additive amount % | LOI% | Drip situation | At charcoal |
| 0 | 21 | Fast drippage | Not at charcoal |
| 10 | 23 | Fast drippage | Not at charcoal |
| 20 | 28 | Slow drippage | At charcoal |
| 25 | 29 | Slow drippage | At charcoal |
As shown in Table 2, when the additive amount when diphenyl Asia phosphono-N- young laying ducks in cage amine in PBT is 20%, limit oxygen
Index value is 28%, has had reached fire retardant rank, though there is slight drippage, carbon-forming performance is fine.
3 product hexichol Asia phosphono-N- young laying ducks in cage amine of table and MCA compounding are for the fire-retardant data in PBT
As shown in Table 3, phosphono-N- young laying ducks in cage amine in product diphenyl Asia has compounded preferable synergistic effect with MCA, also
There is good dilatancy, optimal additive amount proportion is 3: 2, and when total addition level is 25%, limit oxygen index is said up to 32%
System has become nonflammable material at this time after bright compounding, does not drip, and fine at charcoal, and the price of MCA is very cheap, can be big
The production cost of amplitude reduction fire proofing.Thus it can be seen that product diphenyl Asia phosphono-N- young laying ducks in cage amine either
It is used alone, or is compounded with MCA, have preferable flame retardant effect to PBT material.
4 product diphenyl Asia phosphono-N- young laying ducks in cage amine of table and MPP compounding are for the fire-retardant data in PBT
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 29%.
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 (3)
1. a kind of organic phosphine nitrogen combustion inhibitor diphenyl Asia phosphono-N- young laying ducks in cage amine compounds, which is characterized in that the compound
Structure be shown below:
2. a kind of organic phosphine nitrogen combustion inhibitor diphenyl Asia phosphono-N- young laying ducks in cage amine compounds according to claim 1
Preparation method, which is characterized in that this method are as follows:
Equipped with blender, thermometer, dropping funel, be connected to drying tube efficient backflow condensing unit reactor, be added suitable
Organic solvent, young laying ducks in cage amine and triethylamine are measured, the air in reactor is caught up with nitrogen, at 20 °C, starts to be added dropwise
Diphenyl phosphine chloride is not higher than 50 DEG C with rate of addition control drip reacting temperature, and the molar ratio for controlling reaction mass is hexichol
Base phosphonium chloride: young laying ducks in cage amine: triethylamine=1: 1: 1-1: 1.2: 1,80-110 DEG C of back flow reaction is warming up to after being added dropwise
4-6h, cold filtration, is washed with water later, is dried in vacuo to obtain yellowish solid diphenyl Asia phosphono-N- young laying ducks in cage amine；
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:
3. a kind of organic phosphine nitrogen combustion inhibitor diphenyl Asia phosphono-N- young laying ducks in cage amine compounds according to claim 2
Preparation method, which is characterized in that a certain amount of organic solvent be methyl phenyl ethers anisole, dioxane, diethylene glycol dimethyl ether,
Dichloroethanes or acetonitrile, dosage volume ml are 10-15 times of young laying ducks in cage amine quality grams.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811145923.0A CN109180731A (en) | 2018-09-18 | 2018-09-18 | Organic phosphine nitrogen combustion inhibitor diphenyl Asia phosphono-N- young laying ducks in cage amine compounds and preparation method thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811145923.0A CN109180731A (en) | 2018-09-18 | 2018-09-18 | Organic phosphine nitrogen combustion inhibitor diphenyl Asia phosphono-N- young laying ducks in cage amine compounds and preparation method thereof |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112011088A (en) * | 2020-08-06 | 2020-12-01 | 苏州科技大学 | Flame retardant diphenyl phosphinidene organosilicon cage-like ester amine compound and preparation method thereof |
-
2018
- 2018-09-18 CN CN201811145923.0A patent/CN109180731A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112011088A (en) * | 2020-08-06 | 2020-12-01 | 苏州科技大学 | Flame retardant diphenyl phosphinidene organosilicon cage-like ester amine compound and preparation method thereof |
| CN112011088B (en) * | 2020-08-06 | 2022-09-16 | 苏州科技大学 | Flame retardant diphenyl phosphinidene organosilicon cage-like ester amine compound and preparation method thereof |
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Application publication date: 20190111 |