CN109320551A - A kind of synthetic method of fire retardant pair-(p- carboxyl phenylamino) phenyl phosphine oxide - Google Patents
A kind of synthetic method of fire retardant pair-(p- carboxyl phenylamino) phenyl phosphine oxide Download PDFInfo
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- CN109320551A CN109320551A CN201811355648.5A CN201811355648A CN109320551A CN 109320551 A CN109320551 A CN 109320551A CN 201811355648 A CN201811355648 A CN 201811355648A CN 109320551 A CN109320551 A CN 109320551A
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- phosphine oxide
- fire retardant
- phenyl phosphine
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- 239000003063 flame retardant Substances 0.000 title claims abstract description 15
- 238000010189 synthetic method Methods 0.000 title claims abstract description 13
- WKGDNXBDNLZSKC-UHFFFAOYSA-N oxido(phenyl)phosphanium Chemical compound O=[PH2]c1ccccc1 WKGDNXBDNLZSKC-UHFFFAOYSA-N 0.000 title claims abstract description 12
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims abstract description 48
- 229960004050 aminobenzoic acid Drugs 0.000 claims abstract description 23
- 239000002904 solvent Substances 0.000 claims abstract description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000003756 stirring Methods 0.000 claims abstract description 11
- 238000001914 filtration Methods 0.000 claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000007787 solid Substances 0.000 claims abstract description 6
- 238000010792 warming Methods 0.000 claims abstract description 6
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 claims abstract description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 11
- 239000011230 binding agent Substances 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 6
- 239000000047 product Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 238000005406 washing Methods 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 238000004140 cleaning Methods 0.000 description 6
- 239000004952 Polyamide Substances 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 229920002647 polyamide Polymers 0.000 description 5
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000007086 side reaction Methods 0.000 description 4
- 241000207961 Sesamum Species 0.000 description 3
- 235000003434 Sesamum indicum Nutrition 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000004079 fireproofing Methods 0.000 description 3
- -1 glycol compound Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- QCXJEYYXVJIFCE-UHFFFAOYSA-N para-acetamidobenzoic acid Natural products CC(=O)NC1=CC=C(C(O)=O)C=C1 QCXJEYYXVJIFCE-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- 206010054949 Metaplasia Diseases 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 230000015689 metaplastic ossification Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
Classifications
-
- 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 Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/44—Amides thereof
- C07F9/4403—Amides thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4419—Amides of aromatic acids (P-C aromatic linkage)
-
- 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 Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/44—Amides thereof
- C07F9/4434—Amides thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4449—Esters with hydroxyaryl compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/42—Polyamides containing atoms other than carbon, hydrogen, oxygen, and nitrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
Abstract
The present invention relates to a kind of fire retardant pair-(p- carboxyl phenylamino) phenyl phosphine oxide improvement synthetic methods.This method includes the following steps: p-aminobenzoic acid being dissolved in 1, in 4- dioxane solvent, stirring, Isosorbide-5-Nitrae-dioxane solution of diphenylphosphoryl dichloro is slowly added dropwise, 40 ~ 60 DEG C are warming up to after dripping and is reacted 6 ~ 16 hours, cold filtration, solid successively uses dilute hydrochloric acid solution and pure water agitator treating, filtering, is dried in vacuo up to target product, yield is 76 ~ 82%.
Description
Technical field
The invention belongs to the chemical synthesising technologies of organophosphorous fire retardant, and in particular to one kind can industrialized production fire retardant
The preparation method of double-(p- carboxyl phenylamino) phenyl phosphine oxide.
Technical background
Double-(p- carboxyl phenylamino) phenyl phosphine oxide and its derivative belong to halogen-free environment-friendly type phosphonium flame retardant, as anti-
The type fire retardant of answering can be applied in polyester or polyamide material, and material flame retardant test is made to can achieve preferable flame retardant effect,
Nineteen fifty-nine United States Patent (USP) US2882294 (1959) report diphenylphosphoryl dichloro react to obtain with P aminobenzoates it is double-
(p- carboxyl phenylamino) phenyl phosphine oxide ester, and then carry out transesterification with glycol compound and prepare glycol compound, it is used for
The synthesis of flame-retardant polyester material；Document Designed Monomers and Polymers in 2016,2016,19 (5): 420-
428 report double-(the p- carboxyl phenylamino) application of phenyl phosphine oxide in polyamide material.Currently, related with p-aminophenyl first
Acid is directly synthesized for raw material there are mainly two types of the methods of double-(p- carboxyl phenylamino) phenyl phosphine oxide, Literature Designed
Monomers and Polymers, 2016,19 (5): the synthetic method of 420-428 report is diphenylphosphoryl dichloro and 2 times moles
The p-aminobenzoic acid reaction of ratio directly obtains, and the synthetic method of patent CN 104945658 (2015) report is to be with acetic acid
Solvent diphenylphosphoryl dichloro reacts to obtain with the p-aminobenzoic acid of 2 times of molar ratios, however both synthetic methods have obvious disadvantage
End, synthesis side reaction is more, is difficult largely to obtain target product, thus developing one kind has reaction yield higher, and product is pure
It spends, simple for process, the new preparation process for the advantages that production equipment is of less demanding is meaningful.
Summary of the invention
Resistance that is higher with yield, simple for process, being suitble to industrialized production that the purpose of the present invention is to provide a kind of
Agent pair-(p- carboxyl phenylamino) phenyl phosphine oxide synthetic method is fired, side reaction is more, and target produces to solve to react in existing synthetic method
Product are impure or principal product structure problem not pair.
To solve the above problems, present invention provide the technical scheme that the p-aminobenzoic acid of 4 times of moles is dissolved in
In Isosorbide-5-Nitrae-dioxane solvent, stirring is slowly added dropwise Isosorbide-5-Nitrae-dioxane solution of diphenylphosphoryl dichloro, is warming up to after dripping
40~60 DEG C are reacted 6~16 hours, cold filtration, and solid successively uses dilute hydrochloric acid solution and pure water agitator treating, filtering, and vacuum is dry
Dry target product to obtain the final product.Above-mentioned reaction is illustrated below:
It is as follows that the present invention reacts synthetic route:
Its reaction raw materials is consistent with literature method, i.e., the use of diphenylphosphoryl dichloro is that one step of raw material is anti-with p-aminobenzoic acid
Object fire retardant should be prepared, key of the present invention is a difference in that on synthesis technology and improves, and uses Isosorbide-5-Nitrae-dioxy instead first
It is solvent that six rings, which replace acetic acid, and diphenylphosphoryl dichloro and acetic acidreaction is avoided to generate chloroacetic chloride side reaction, chloroacetic chloride can with to ammonia
Yl benzoic acid reaction can generate a large amount of 4- acetaminobenzoic acid；Secondly, this patent has used acid binding agent, it is endless to solve reaction
Full situation.
The present invention uses Isosorbide-5-Nitrae-dioxane for solvent, and usage amount is to ensure that raw material p-aminobenzoic acid can be completely dissolved
Amount, use can directly be recycled or steam and use after purification again by reacting the solvent filtered out.
The hydrogen chloride gas that the present invention uses acid binding agent absorbing reaction to generate, acid binding agent are p-aminobenzoic acid itself or three
Ethamine uses 2 times that mole is raw material diphenylphosphoryl dichloro molal quantity.It can be ensured instead using conventional acid binding agent triethylamine
Should go on smoothly, diphenylphosphoryl dichloro: triethylamine: the molar ratio of p-aminobenzoic acid be 1:2:2~2.20, reaction yield 53~
65%；When acid binding agent is changed to p-aminobenzoic acid, diphenylphosphoryl dichloro: the molar ratio of p-aminobenzoic acid is 1:4~4.20,
Yield obviously increases, and for reaction yield up to 76~82%, reason may be that triethylamine can activate diphenylphosphoryl dichloro, improves
Its reactivity, and then increase the generation of various side reactions.
The reaction temperature that the present invention uses is 40~60 DEG C, 6~16h of reaction time, wherein preferable reaction temperature 45~50
DEG C, 8~12h of reaction time.
The Main By product of synthetic reaction is para-aminobenzoate when the present invention using p-aminobenzoic acid is acid binding agent
Hydrochlorate, it returns Precipitation together with product, and the para-aminobenzoate hydrochlorate in product can be by adding appropriate dilute hydrochloric acid such as to beat
It starches agitator treating to remove, concentration of hydrochloric acid is 0.1~1.0mol/L, guarantees that cleaning solution pH value is 1~2, product makes after washing
With pure water 2 times, cleaning solution pH value shows that washing is complete when being 3~4.
When the present invention using p-aminobenzoic acid is acid binding agent, containing largely to amino in the waste water of dilute hydrochloric acid washed product
Benzoate hydrochlorate, using in sodium hydrate aqueous solution and waste water to pH value 4.5~5.0, a large amount of p-aminobenzoic acid can be cold
But it is precipitated, it is recyclable after this precipitating filtration drying, achieve the purpose that reduce production cost.
Compared with prior art, the device have the advantages that being mainly manifested in using p-aminobenzoic acid or triethylamine
For acid binding agent, reaction is promoted to go on smoothly, next uses the Isosorbide-5-Nitrae-dioxy six for having preferable solubility to raw material p-aminobenzoic acid instead
Ring is the by-product generation that solvent can avoid that acetic acid is solvent initiation, and synthesis technology of the present invention is simple and easy, is suitble to industry
Metaplasia produces.
Specific embodiment
Below by specific embodiment, technical solution of the present invention is further described in detail, but the present invention and unlimited
The preparation process under other conditions may be implemented referring to the method for following embodiments in these embodiments.
Embodiment one:
8.33g (0.061mol) p-aminobenzoic acid is weighed in three-necked flask, 65mL solvent Isosorbide-5-Nitrae-dioxane is added,
After the stirring and dissolving at 35~40 DEG C, 2.93g (0.015mol) diphenylphosphoryl dichloro and the mixing of 5.0mL1,4- dioxane solvent
It is added dropwise in reaction flask with constant pressure funnel uniform speed slow, 45~50 DEG C is warming up to after dripping, reacted 12 hours, be cooled to
Room temperature filters, and solid is transferred in beaker by washing, and appropriate 1mol/L dilute hydrochloric acid stirring to pulp is added to wash, and guarantees cleaning solution pH
Value filters, solid product, which transfers in sesame seed cake, to be added pure water 1~2 time, until cleaning solution pH value to 1~2 after stirring 30min
Until 3~4, it is dried in vacuo to obtain product 4.74g, yield is about 79.8%, and 297.2~302.8 DEG C of fusing point, phosphorus content
7.70%, product can be directly used in the synthesis of polyamide fire proofing.
Embodiment two:
4.17g (0.031mol) p-aminobenzoic acid and 3.04g (0.030mol) triethylamine are weighed in 150mL three-necked flask
In, be added 45mL solvent Isosorbide-5-Nitrae-dioxane, stirring and dissolving at room temperature, 2.93g (0.015mol) diphenylphosphoryl dichloro with
It is added dropwise in reaction flask after the mixing of 5.0mL1,4- dioxane solvent with constant pressure funnel uniform speed slow, about 20min is dripped
45~50 DEG C are warming up to after finishing, the reaction was continued 8 hours, is cooled to room temperature, and filters, and solid is transferred in beaker, adds by washing
The washing of 30mL1mol/L dilute hydrochloric acid stirring to pulp guarantees that cleaning solution pH value to 1~2, filters, solid product is again after stirring 30min
It is transferred in sesame seed cake and adds pure water 1~2 time, until cleaning solution pH value until 3~4, is dried in vacuo to obtain product 3.34g, yield
About 56.2%, product can be directly used in the synthesis of polyamide fire proofing.
Embodiment three:
170.1g (1.24mol) p-aminobenzoic acid is weighed in 3L three-necked flask, 1000mL solvent Isosorbide-5-Nitrae-dioxy is added
Six rings, mechanical stirring dissolves at 35 DEG C, and 58.5g (0.30mol) diphenylphosphoryl dichloro and 150mL1,4- dioxane solvent mix
It is added dropwise in reaction flask with constant pressure funnel uniform speed slow afterwards, 45~50 DEG C is warming up to after dripping, reacted 12 hours, it is cooling
It to room temperature, filters, solid is transferred in 5L beaker by washing, and 2.5L mol/L dilute hydrochloric acid stirring to pulp is added to wash, and guarantees washing
Liquid pH value filters, solid product, which transfers in sesame seed cake, to be added appropriate pure water 1~2 time, until washing to 1.0 after stirring 45min
Liquid pH value is dried in vacuo to obtain product 97.3g until 3~4, and yield is about 81.9%, and 295.4~302.6 DEG C of fusing point, product
Can be directly used for polyamide fire proofing synthesis in, dilute hydrochloric acid waste water using sodium hydroxide solution be neutralized to pH value be 4.5~5 when
Recyclable part p-aminobenzoic acid raw material.
Claims (4)
1. a kind of fire retardant pair-(p- carboxyl phenylamino) phenyl phosphine oxide synthetic method, which is characterized in that the synthetic method
Steps are as follows: p-aminobenzoic acid is dissolved in Isosorbide-5-Nitrae-dioxane solvent, stirs, the 1 of diphenylphosphoryl dichloro is slowly added dropwise,
4- dioxane solution is warming up to 40 ~ 60 DEG C and reacts 6 ~ 16 hours after dripping, cold filtration, solid successively uses dilute hydrochloric acid molten
Liquid and pure water agitator treating, filtering, are dried in vacuo up to target product.
2. fire retardant according to claim 1 pair-(p- carboxyl phenylamino) phenyl phosphine oxide synthetic method, feature
It is, the p-aminobenzoic acid is that reactant is also acid binding agent, and the molar ratio of dosage and diphenylphosphoryl dichloro dosage is
4.00~4.20:1。
3. fire retardant according to claim 2 pair-(p- carboxyl phenylamino) phenyl phosphine oxide synthetic method, feature
It is, uses triethylamine to substitute p-aminobenzoic acid as acid binding agent, then diphenylphosphoryl dichloro: triethylamine: p-aminobenzoic acid
Molar ratio be 1:2:2 ~ 2.20.
4. fire retardant according to claim 1 pair-(p- carboxyl phenylamino) phenyl phosphine oxide synthetic method, feature
It is, the reaction temperature is 45 ~ 50 DEG C, 8 ~ 12 h of reaction time.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811355648.5A CN109320551B (en) | 2018-11-14 | 2018-11-14 | Synthetic method of flame retardant bis- (p-carboxyphenylamino) phenylphosphine oxide |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811355648.5A CN109320551B (en) | 2018-11-14 | 2018-11-14 | Synthetic method of flame retardant bis- (p-carboxyphenylamino) phenylphosphine oxide |
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| Publication Number | Publication Date |
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| CN109320551A true CN109320551A (en) | 2019-02-12 |
| CN109320551B CN109320551B (en) | 2022-03-18 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112538091A (en) * | 2020-11-26 | 2021-03-23 | 湖北大学 | Synthesis method of high-purity bis- (p-carboxyphenylamino) phenylphosphine oxide flame retardant |
| CN113594605A (en) * | 2021-07-31 | 2021-11-02 | 浙江米皇新材股份有限公司 | Automobile battery aluminum-clad section |
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| CN104072759A (en) * | 2014-06-20 | 2014-10-01 | 南京航空航天大学 | P-N expanded reaction type flame retardant and preparation method thereof |
| CN104945658A (en) * | 2015-06-03 | 2015-09-30 | 南京立汉化学有限公司 | Reaction-type halogen-free flame retardant bis-(p-aminocarboxyphenyl)phenylphosphine oxide and synthetic method thereof |
| WO2017133517A1 (en) * | 2016-02-03 | 2017-08-10 | 四川海思科制药有限公司 | Phosphamide derivative, method for manufacturing the same, and uses thereof |
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| CN104072759A (en) * | 2014-06-20 | 2014-10-01 | 南京航空航天大学 | P-N expanded reaction type flame retardant and preparation method thereof |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112538091A (en) * | 2020-11-26 | 2021-03-23 | 湖北大学 | Synthesis method of high-purity bis- (p-carboxyphenylamino) phenylphosphine oxide flame retardant |
| CN112538091B (en) * | 2020-11-26 | 2022-09-09 | 湖北大学 | Synthesis method of bis- (p-carboxyphenylamino) phenylphosphine oxide flame retardant |
| CN113594605A (en) * | 2021-07-31 | 2021-11-02 | 浙江米皇新材股份有限公司 | Automobile battery aluminum-clad section |
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| CN109320551B (en) | 2022-03-18 |
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