CN109553640A - Miscellaneous trimethylene phosphazene compound of fire retardant trimerization O, O-2- methylol phosphono and preparation method thereof - Google Patents
Miscellaneous trimethylene phosphazene compound of fire retardant trimerization O, O-2- methylol phosphono and preparation method thereof Download PDFInfo
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- CN109553640A CN109553640A CN201811566188.0A CN201811566188A CN109553640A CN 109553640 A CN109553640 A CN 109553640A CN 201811566188 A CN201811566188 A CN 201811566188A CN 109553640 A CN109553640 A CN 109553640A
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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
- C07F9/6581—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 nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/659—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 nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having three phosphorus atoms as ring hetero atoms in the same ring
Abstract
The present invention relates to a kind of miscellaneous trimethylene phosphazene compounds of fire retardant trimerization O, O-2- methylol phosphono and preparation method thereof, and the structure of the compound is shown below:
Description
Technical field
The present invention relates to a kind of miscellaneous trimethylene phosphazene compound of fire retardant trimerization O, O-2- methylol phosphono and preparation method thereof,
The compound contains the double ignition-proof elements of phosphorus, nitrogen, can be used as polyester, polyamide, polyurethane, epoxy resin, unsaturated-resin, poly- second
The fire retardant of enol and coating etc..
Background technique
The progress and the improvement of people's living standards of science and technology promote the fast-developing and wide of Macromolecular materials industry
General application, simultaneously the inflammability of high molecular material also often causes fire, can bring to the security of the lives and property of people
Harm, to promote the development of flame-retarded technology.With the continuous enhancing of health of people and environmental consciousness, halogenated flame retardant is being permitted
Various aspects are restricted.With phosphorus, nitrogen expansion type flame retardant as main component, have the advantages that oxygen barrier, insulation, suppression cigarette, and
It can be effectively prevented the generation for melting drop, thus the phosphor-nitrogen expansion type combustion inhibitor of Halogen, low cigarette, low toxicity has catered to the urgency in market
Need property requires.
The miscellaneous trimethylene phosphonitrile of fire retardant trimerization O, O-2- methylol phosphono of the present invention belongs to the more N structures of more phosphorus, and phosphorus content is high, also
There is cooperative flame retardant elemental nitrogen.The product structure symmetry is good, and aromatic is stablized, and decomposition temperature is high, good with high molecular material compatibility,
Adapt to the high temperature process of material；It is made by hexachlorocyclotriph,sphazene and trihydroxy methyl phosphorous oxide for raw material single step reaction, and former
Expect cheap and easy to get, has a wide range of application, very big demand is contained in market.
Summary of the invention
It is an object of the present invention to propose a kind of miscellaneous trimethylene phosphonitrile chemical combination of fire retardant trimerization O, O-2- methylol phosphono
Object, physical and chemical performance is stablized, nontoxic, and flame-retarded efficiency is high, good with high molecular material compatibility, can overcome it is in the prior art not
Foot.
For achieving the above object, present invention employs following technical solutions:
A kind of miscellaneous trimethylene phosphazene compound of fire retardant trimerization O, O-2- methylol phosphono, which is characterized in that the compound
Structure is shown below:
Another object of the present invention is to propose a kind of miscellaneous trimethylene phosphonitrile chemical combination of fire retardant trimerization O, O-2- methylol phosphono
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 into organic solvent, acid binding agent is added, controls hexachlorocyclotriph,sphazene and trihydroxy methyl
Phosphorous oxide and the molar ratio of acid binding agent are 1: 3: 6 reaction, trihydroxy methyl phosphorous oxide are added drop-wise in above-mentioned solution, cooling condition
Under, 40 DEG C are not higher than with rate of addition control reaction temperature, 100 DEG C~130 DEG C are warming up to after dripping off, insulation reaction 5-8h；Drop
Temperature is to 30 DEG C hereinafter, the acid binding agent hydrochloride that suction filtration removing generates, is evaporated under reduced pressure out organic solvent (recycling), is separately added into
The water washing of relative product Theoretical Mass 2~3 times of volumes ml of grams twice, separates lower layer's organic phase, adds opposite production
The ethyl acetate of object Theoretical Mass 2~3 times of volumes ml of grams, is dried with anhydrous sodium sulfate, is filtered, and filtrate decompression is steamed
Ethyl acetate is removed in distillation, obtains the colorless and transparent miscellaneous trimethylene phosphonitrile of viscous liquid trimerization O, O-2- methylol phosphono.
This method may be used also are as follows:
Hexachlorocyclotriph,sphazene is dissolved into organic solvent, 3 times moles of hexachlorocyclotriph,sphazene of trihydroxy methyl oxidation is added dropwise
Phosphorus under cooling condition, is not higher than 40 DEG C with rate of addition control reaction temperature, 100 DEG C~130 DEG C is warming up to after dripping off, heat preservation
8~11h is reacted, until releasing without hydrogen chloride；30 DEG C are cooled to hereinafter, be evaporated under reduced pressure out organic solvent (recycling), respectively plus
The water washing for entering relative product Theoretical Mass 2~3 times of volumes ml of grams twice, separates lower layer's organic phase, and opposite produce is added
The ethyl acetate of object Theoretical Mass 2~3 times of volumes ml of grams, is dried with anhydrous sodium sulfate, is filtered, and filtrate decompression is steamed
Ethyl acetate is removed in distillation, obtains the colorless and transparent miscellaneous trimethylene phosphonitrile of viscous liquid trimerization O, O-2- methylol phosphono.
Acid-binding agent as described above is triethylamine, n,N-Dimethylaniline or pyridine.
Organic solvent as described above is dioxane, toluene, ethylene glycol diethyl ether and chlorobenzene, the volume of organic solvent
It ml is 3: 1~5: 1 with the ratio between the quality grams of hexachlorocyclotriph,sphazene.
The miscellaneous trimethylene phosphazene compound of trimerization O, O-2- methylol phosphono of the invention is colorless and transparent viscous liquid, and density is
1.347 (25 DEG C), index of refraction nD 25=1.2934, yield is 89.9%~96.1%, can be used as polyester, polyamide, poly- ammonia
The fire retardant of ester, epoxy resin, unsaturated-resin, polyvinyl alcohol and coating etc..Fire retardant trimerization O, O-2- methylol phosphono
The preparation principle of miscellaneous trimethylene phosphazene compound is shown below:
Compared with prior art, the invention has the beneficial effects that:
1. the miscellaneous trimethylene phosphazene compound structure novel of fire retardant trimerization O, O-2- methylol phosphono of the present invention, phosphorus content are up to
33.9%, nitrogen content is up to 7.7%, and ignition-proof element total content is up to 41.6%.Symmetrical configuration is good, and stability is high, can be suitably used for
The high temperature process of various engineering plastics, nitrogen phosphorus cooperative flame retardant efficiency is high, has good plasticity；
2. the miscellaneous trimethylene phosphonitrile of fire retardant trimerization O, O-2- methylol phosphono of the present invention is halogen-free, it is good for the environment, belongs to swollen
The swollen environmental-friendly fire retardant of type；
3. the preparation method of the miscellaneous trimethylene phosphonitrile of fire retardant trimerization O, O-2- methylol phosphono of the present invention is single step reaction, technique
Simply, synthesis process does not introduce impurity without adding catalyst；Equipment is simple, low in cost, is suitable for large-scale production, has very well
Application and development prospect.
Following spectrum data is provided in order to further illustrate the structure and performance spy of product.
1, the infared spectrum data of the miscellaneous trimethylene phosphonitrile of fire retardant trimerization O, O-2- methylol phosphono: 3400.5cm-1Place is hydroxyl
The stretching vibration peak of base O-H key, 2925.6cm-1And 1490.8cm-1Place is methylene c h bond absorption peak, 1123.3cm-1With
1148.5cm-1The absorption peak of C-O, 1255.2cm-1For the stretching vibration absworption peak of phosphazene backbone P=N, 1050.3cm-1For phosphonitrile
The stretching vibration absworption peak of P-N, 1264.5cm on skeleton-1For the absorption peak of P=O, 1142.2cm-1For the absorption peak of P-O,
800.4cm-1Place is the stretching vibration peak of C-P key.
2, the nuclear magnetic spectrum data of the miscellaneous trimethylene phosphonitrile of fire retardant trimerization O, O-2- methylol phosphono: δ 3.60-3.75 is-N
=P-O-CH2On the peak H；δ 3.80-3.95 is HO-CH2On the peak methylene H；δ 4.21-4.34 is the peak H of hydroxyl.
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, 10.42g (0.03mol) hexachlorocyclotriph,sphazene, 80ml dioxane is added
With 18.18g (0.18mol) triethylamine, after stirring dissolves hexachlorocyclotriph,sphazene, 12.61g (0.09mol) trihydroxy methyl is added dropwise
Phosphorous oxide is not higher than 40 DEG C with rate of addition control reaction temperature, 100 DEG C is warming up to after dripping off, insulation reaction 8h；It is cooled to 30
DEG C hereinafter, filter remove generate triethylamine hydrochloride, vacuum distillation remove dioxane (recycling), be separately added into 35ml
Distilled water washes twice, and separates lower layer's organic phase, and 35ml ethyl acetate is added, is dried with 1g anhydrous magnesium sulfate, filters, filter
Liquid vacuum distillation removes ethyl acetate, obtains the colorless and transparent miscellaneous trimethylene phosphonitrile of viscous liquid trimerization O, O-2- methylol phosphono, yield:
90.3%, density is 1.347 (25 DEG C), index of refraction nD 25=1.2934.
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 10.42g (0.03mol) hexachlorocyclotriph,sphazene, 80ml toluene and
After stirring dissolves hexachlorocyclotriph,sphazene, 12.61g (0.09mol) three is added dropwise in 21.78g (0.18mol) n,N-Dimethylaniline
Methylol phosphorous oxide is not higher than 40 DEG C with rate of addition control reaction temperature, 110 DEG C is warming up to after dripping off, insulation reaction 7h；Drop
For temperature to 30 DEG C hereinafter, filtering the n,N-Dimethylaniline hydrochloride for removing and generating, vacuum distillation removes toluene (recycling), point
Not Jia Ru 35ml distilled water wash twice, separate lower layer's organic phase, 35ml ethyl acetate be added, is done with 1g anhydrous magnesium sulfate
It is dry, it filters, filtrate decompression is distilled off ethyl acetate, obtains the miscellaneous trimethylene of colorless and transparent viscous liquid trimerization O, O-2- methylol phosphono
Phosphonitrile, yield: 91.7%, density is 1.347 (25 DEG C), index of refraction nD 25=1.2934.
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, 10.42g (0.03mol) hexachlorocyclotriph,sphazene, 80ml ethylene glycol two is added
After stirring dissolves hexachlorocyclotriph,sphazene, 12.61g (0.09mol) three hydroxyl first is added dropwise in ether and 14.22g (0.18mol) pyridine
Base phosphorous oxide is not higher than 40 DEG C with rate of addition control reaction temperature, 120 DEG C is warming up to after dripping off, insulation reaction 6h；Cooling
To 30 DEG C hereinafter, filter remove generate pyridine hydrochloride, vacuum distillation remove ethylene glycol diethyl ether (recycling), respectively plus
Enter 35ml distilled water to wash twice, separate lower layer's organic phase, 35ml ethyl acetate is added, is dried with 1g anhydrous magnesium sulfate,
It filters, filtrate decompression is distilled off ethyl acetate, obtains the colorless and transparent miscellaneous trimethylene phosphorus of viscous liquid trimerization O, O-2- methylol phosphono
Nitrile, yield: 96.1%, density is 1.347 (25 DEG C), index of refraction nD 25=1.2934.
Embodiment 4 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 10.42g (0.03mol) hexachlorocyclotriph,sphazene, 80ml chlorobenzene and
After stirring dissolves hexachlorocyclotriph,sphazene, the oxidation of 12.61g (0.09mol) trihydroxy methyl is added dropwise in 14.22g (0.18mol) pyridine
Phosphorus is not higher than 40 DEG C with rate of addition control reaction temperature, 130 DEG C is warming up to after dripping off, insulation reaction 5h；Be cooled to 30 DEG C with
Under, the pyridine hydrochloride for removing and generating is filtered, vacuum distillation removes chlorobenzene (recycling), is separately added into 35ml distillation water washing
Twice, lower layer's organic phase is separated, 35ml ethyl acetate is added, is dried with 1g anhydrous magnesium sulfate, is filtered, filtrate decompression distillation
Ethyl acetate is removed, obtains the colorless and transparent miscellaneous trimethylene phosphonitrile of viscous liquid trimerization O, O-2- methylol phosphono, yield: 94.8%, it is close
Degree is 1.347 (25 DEG C), index of refraction nD 25=1.2934.
Embodiment 5 equipped with blender, thermometer, high performance reflux condenser and hydrogen chloride absorption device reactor in,
Under nitrogen protection, 10.42g (0.03mol) hexachlorocyclotriph,sphazene and 80ml dioxane is added, stirring keeps hexachlorocyclotriph,sphazene molten
12.61g (0.09mol) trihydroxy methyl phosphorous oxide is added dropwise in Xie Hou, is not higher than 40 DEG C with rate of addition control reaction temperature, drips off
After be warming up to 100 DEG C, insulation reaction 11h, until without hydrogen chloride release；30 DEG C are cooled to hereinafter, vacuum distillation removes dioxane
(recycling) is separately added into 35ml distilled water and washes twice, and separates lower layer's organic phase, and 35ml ethyl acetate is added, with 1g without
Water magnesium sulfate is dried, and filters, and filtrate decompression is distilled off ethyl acetate, obtains colorless and transparent viscous liquid trimerization O, O-2- hydroxyl
The miscellaneous trimethylene phosphonitrile of methyl phosphono, yield: 89.9%, density is 1.347 (25 DEG C), index of refraction nD 25=1.2934.
Embodiment 6 equipped with blender, thermometer, high performance reflux condenser and hydrogen chloride absorption device reactor in,
Under nitrogen protection, 10.42g (0.03mol) hexachlorocyclotriph,sphazene and 80ml toluene is added, stirring dissolves hexachlorocyclotriph,sphazene
Afterwards, 12.61g (0.09mol) trihydroxy methyl phosphorous oxide is added dropwise, is not higher than 40 DEG C, after dripping off with rate of addition control reaction temperature
110 DEG C, insulation reaction 10h are warming up to, until releasing without hydrogen chloride；30 DEG C are cooled to hereinafter, vacuum distillation removes toluene (recycling benefit
With), it is separately added into 35ml distilled water and washes twice, separate lower layer's organic phase, 35ml ethyl acetate is added, with 1g anhydrous magnesium sulfate
It is dried, filters, filtrate decompression is distilled off ethyl acetate, obtains colorless and transparent viscous liquid trimerization O, O-2- methylol phosphono
Miscellaneous trimethylene phosphonitrile, yield: 91.5%, density is 1.347 (25 DEG C), index of refraction nD 25=1.2934.
Embodiment 7 equipped with blender, thermometer, high performance reflux condenser and hydrogen chloride absorption device reactor in,
Under nitrogen protection, 10.42g (0.03mol) hexachlorocyclotriph,sphazene and 80ml ethylene glycol diethyl ether is added, stirring makes three phosphorus of chlordene ring
After nitrile dissolution, 12.61g (0.09mol) trihydroxy methyl phosphorous oxide is added dropwise, is not higher than 40 DEG C with rate of addition control reaction temperature,
120 DEG C, insulation reaction 9h are warming up to after dripping off, until releasing without hydrogen chloride；30 DEG C are cooled to hereinafter, vacuum distillation removes ethylene glycol
Diethyl ether (recycling) is separately added into 35ml distilled water and washes twice, and separates lower layer's organic phase, and 35ml ethyl acetate is added,
It is dried, is filtered with 1g anhydrous magnesium sulfate, filtrate decompression is distilled off ethyl acetate, obtains colorless and transparent viscous liquid trimerization
The miscellaneous trimethylene phosphonitrile of O, O-2- methylol phosphono, yield: 95.4%, density is 1.347 (25 DEG C), index of refraction nD 25=
1.2934。
Embodiment 8 equipped with blender, thermometer, high performance reflux condenser and hydrogen chloride absorption device reactor in,
Under nitrogen protection, 10.42g (0.03mol) hexachlorocyclotriph,sphazene and 80ml chlorobenzene is added, stirring dissolves hexachlorocyclotriph,sphazene
Afterwards, 12.61g (0.09mol) trihydroxy methyl phosphorous oxide is added dropwise, is not higher than 40 DEG C, after dripping off with rate of addition control reaction temperature
130 DEG C, insulation reaction 8h are warming up to, until releasing without hydrogen chloride；30 DEG C are cooled to hereinafter, vacuum distillation removes chlorobenzene (recycling benefit
With), it is separately added into 35ml distilled water and washes twice, separate lower layer's organic phase, 35ml ethyl acetate is added, with 1g anhydrous magnesium sulfate
It is dried, filters, filtrate decompression is distilled off ethyl acetate, obtains colorless and transparent viscous liquid trimerization O, O-2- methylol phosphono
Miscellaneous trimethylene phosphonitrile, yield: 93.7%, density is 1.347 (25 DEG C), index of refraction nD 25=1.2934.
1 preparation example main technologic parameters of table
The miscellaneous trimethylene phosphonitrile of fire retardant trimerization O, O-2- methylol phosphono of above-mentioned synthesis is also applied to PVC by inventor
In, take polyvinyl chloride (PVC), dioctyl phthalate (DOP), antimony oxide (Sb2O3) and product trimerization O, O-2- hydroxyl
In varing proportions after mixing, then with XJ-01 type extruder extrusion diameter 3mm, length is made in the miscellaneous trimethylene phosphonitrile of methyl phosphono
The batten of 15cm.Reference: the limit oxygen of GB/T2406-2008 " Plastics Combustion method for testing performance-oxygen index method " test sample item refers to
Number.Test result is as shown in table 2:
The 2 miscellaneous trimethylene phosphonitrile flame retardant property in PVC of fire retardant trimerization O, O-2- methylol phosphono of table
It is generally acknowledged that the limit oxygen index of fire proofing, which reaches 27 or more, preferable flame retardant property.Polyvinyl chloride itself
Chlorinty is very high, is good fire proofing, but since the addition of inflammable plasticizer causes flame retardant property to reduce, and table 2 shows to add
Limit oxygen index only has 21 when entering 100 parts of plasticizer, easily burns in air, but with trimerization O, O-2- methylol phosphono is miscellaneous
The increase of trimethylene phosphonitrile, limit oxygen index increase quickly, and LOI reaches 29 when being added 10 parts, shows that the product has very high resistance
Fuel efficiency energy；Simultaneously it was found that, the fire retardant also has preferable plasticity, plasticizer can be reduced in polyvinyl chloride
Usage amount.
Claims (5)
1. a kind of miscellaneous trimethylene phosphazene compound of fire retardant trimerization O, O-2- methylol phosphono, which is characterized in that the knot of the compound
Structure is shown below:
2. the preparation side of the miscellaneous trimethylene phosphazene compound of fire retardant trimerization O, O-2- methylol phosphono according to claim 1
Method, which is characterized in that this method are as follows:
Hexachlorocyclotriph,sphazene is dissolved into organic solvent, acid binding agent is added, controls hexachlorocyclotriph,sphazene and trihydroxy methyl oxidation
The molar ratio of phosphorus and acid binding agent is 1: 3: 6 reaction, and trihydroxy methyl phosphorous oxide is added drop-wise in above-mentioned solution, under cooling condition, with
Rate of addition controls reaction temperature and is not higher than 40 DEG C, 100 DEG C~130 DEG C is warming up to after dripping off, insulation reaction 5-8h；It is cooled to 30
DEG C hereinafter, filter remove generate acid binding agent hydrochloride, be evaporated under reduced pressure out organic solvent, be separately added into relative product Theoretical Mass
The water washing of 2~3 times of volumes ml of grams twice, separates lower layer's organic phase, add relative product Theoretical Mass grams 2~
The ethyl acetate of 3 times of volumes ml, is dried with anhydrous sodium sulfate, is filtered, and filtrate decompression is distilled off ethyl acetate, obtains
The colorless and transparent miscellaneous trimethylene phosphonitrile of viscous liquid trimerization O, O-2- methylol phosphono.
3. the preparation side of the miscellaneous trimethylene phosphazene compound of fire retardant trimerization O, O-2- methylol phosphono according to claim 1
Method, which is characterized in that this method are as follows:
Hexachlorocyclotriph,sphazene is dissolved into organic solvent, 3 times moles of hexachlorocyclotriph,sphazene of trihydroxy methyl phosphorous oxide is added dropwise, it is cold
But under the conditions of, 40 DEG C is not higher than with rate of addition control reaction temperature, 100 DEG C~130 DEG C are warming up to after dripping off, insulation reaction 8
~11h, until being released without hydrogen chloride；30 DEG C are cooled to hereinafter, be evaporated under reduced pressure out organic solvent, is separately added into relative product theory matter
The water washing for measuring 2~3 times of volumes ml of grams twice, separates lower layer's organic phase, be added relative product Theoretical Mass grams 2~
The ethyl acetate of 3 times of volumes ml, is dried with anhydrous sodium sulfate, is filtered, and filtrate decompression is distilled off ethyl acetate, obtains
The colorless and transparent miscellaneous trimethylene phosphonitrile of viscous liquid trimerization O, O-2- methylol phosphono.
4. the preparation side of the miscellaneous trimethylene phosphazene compound of fire retardant trimerization O, O-2- methylol phosphono 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 the miscellaneous trimethylene phosphazene compound of fire retardant trimerization O, O-2- methylol phosphono described in claim 2 and 3
Method, it is characterised in that: the organic solvent be dioxane, toluene, ethylene glycol diethyl ether and chlorobenzene, organic solvent
The ratio between volume ml and the quality grams of hexachlorocyclotriph,sphazene are 3: 1~5: 1.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4405738A (en) * | 1982-03-05 | 1983-09-20 | Akzona Incorporated | Flame retardant additives and flame retardant polyester compositions |
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2018
- 2018-12-10 CN CN201811566188.0A patent/CN109553640A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4405738A (en) * | 1982-03-05 | 1983-09-20 | Akzona Incorporated | Flame retardant additives and flame retardant polyester compositions |
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