CN104231312B - Triazine triphenyl phosphinicacid ethyl ester fire retardant combination and its application process - Google Patents
Triazine triphenyl phosphinicacid ethyl ester fire retardant combination and its application process Download PDFInfo
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- CN104231312B CN104231312B CN201410507953.7A CN201410507953A CN104231312B CN 104231312 B CN104231312 B CN 104231312B CN 201410507953 A CN201410507953 A CN 201410507953A CN 104231312 B CN104231312 B CN 104231312B
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- ttpe
- fire retardant
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- pems
- dopo
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- 239000003063 flame retardant Substances 0.000 title claims abstract description 55
- SLTXIOBRDOEBQM-UHFFFAOYSA-N C1(=CC=CC=C1)OP(=O)(C1=CC=CC=C1)C1=CC=CC=C1.N1=NN=CC=C1 Chemical compound C1(=CC=CC=C1)OP(=O)(C1=CC=CC=C1)C1=CC=CC=C1.N1=NN=CC=C1 SLTXIOBRDOEBQM-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title claims abstract description 10
- BUCXEFZXWKUCCY-UHFFFAOYSA-N 4-methyl-3-(2-phenylethyl)-1,2,4-oxadiazol-5-one Chemical compound O1C(=O)N(C)C(CCC=2C=CC=CC=2)=N1 BUCXEFZXWKUCCY-UHFFFAOYSA-N 0.000 claims abstract description 29
- 238000002229 photoelectron microspectroscopy Methods 0.000 claims abstract description 29
- DWSWCPPGLRSPIT-UHFFFAOYSA-N benzo[c][2,1]benzoxaphosphinin-6-ium 6-oxide Chemical compound C1=CC=C2[P+](=O)OC3=CC=CC=C3C2=C1 DWSWCPPGLRSPIT-UHFFFAOYSA-N 0.000 claims abstract description 28
- 229920000728 polyester Polymers 0.000 claims abstract description 24
- -1 phospho Chemical class 0.000 claims abstract description 9
- 229920000877 Melamine resin Polymers 0.000 claims abstract description 3
- 229920000388 Polyphosphate Polymers 0.000 claims abstract description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000001205 polyphosphate Substances 0.000 claims abstract description 3
- 235000011176 polyphosphates Nutrition 0.000 claims abstract description 3
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims 1
- 238000001125 extrusion Methods 0.000 claims 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims 1
- NCWQJOGVLLNWEO-UHFFFAOYSA-N methylsilicon Chemical compound [Si]C NCWQJOGVLLNWEO-UHFFFAOYSA-N 0.000 claims 1
- 238000005829 trimerization reaction Methods 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 13
- 239000004743 Polypropylene Substances 0.000 abstract description 4
- 239000003822 epoxy resin Substances 0.000 abstract description 4
- 229920000647 polyepoxide Polymers 0.000 abstract description 4
- 229920001155 polypropylene Polymers 0.000 abstract description 4
- 230000002195 synergetic effect Effects 0.000 abstract description 4
- 239000007977 PBT buffer Substances 0.000 abstract description 3
- 230000007613 environmental effect Effects 0.000 abstract description 3
- 229920001707 polybutylene terephthalate Polymers 0.000 abstract description 3
- 229920002635 polyurethane Polymers 0.000 abstract description 3
- 239000004814 polyurethane Substances 0.000 abstract description 3
- ZQKXQUJXLSSJCH-UHFFFAOYSA-N melamine cyanurate Chemical compound NC1=NC(N)=NC(N)=N1.O=C1NC(=O)NC(=O)N1 ZQKXQUJXLSSJCH-UHFFFAOYSA-N 0.000 abstract description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 abstract 2
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 abstract 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 28
- 229910052760 oxygen Inorganic materials 0.000 description 28
- 239000001301 oxygen Substances 0.000 description 28
- 238000003756 stirring Methods 0.000 description 14
- 235000013399 edible fruits Nutrition 0.000 description 8
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 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
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 238000000280 densification Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000003754 machining Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- BSYJHYLAMMJNRC-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-ol Chemical compound CC(C)(C)CC(C)(C)O BSYJHYLAMMJNRC-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- KUXDQQMEFBFTGX-UHFFFAOYSA-N [N].P Chemical compound [N].P KUXDQQMEFBFTGX-UHFFFAOYSA-N 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000002079 cooperative effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The present invention relates to a kind of triazine triphenyl phosphinicacid ethyl ester fire retardant combination and its application process.The fire retardant combination be by melamine cyanurate (abbreviation MCA), melamine polyphosphate (abbreviation MPP), 9, any two kinds, three kinds or four kinds in 10 dihydro, 9 oxa-, 10 phospho hetero phenanthrene, 10 oxide (abbreviation DOPO), pentaerythritol methylsilicate (abbreviation PEMS) are compounded, are uniformly mixed to prepare with arbitrary proportion with triazine triphenyl phosphinicacid ethyl ester (abbreviation TTPE), and the weight fraction of TTPE is more than zero.Fire retardant combination of the present invention, have the advantages that multielement synergistic function, fire resistance are good, and material compatibility is good, low cost, halogen-free environmental, can be used as the fire retardant of the materials such as polyester PET, polyester PBT, polyurethane, polypropylene, epoxy resin, have good application prospect.
Description
Technical field
The present invention relates to a kind of triazine triphenyl phosphinicacid ethyl ester fire retardant combination and its application process, the fire retardant group
Compound can be used as the fire retardant of the materials such as polyester PET, polyester PBT, polyurethane, polypropylene, epoxy resin.
Background technology
The organophosphorous fire retardant of broad sense mostly is liquid, have that little molecular weight, poor heat resistance, volatility are big, smoke amount is big, and
The poor compatibility of material, animal migration are strong, narrow application range, low phosphorus content, poor flame retardant properties the shortcomings of.Therefore it is badly in need of opening on market
Send out the organic phosphine fire retardant of high comprehensive performance.And multielement synergetic organic phosphine fire retardant can give material it is preferably fire-retardant and
Machining property, so design intramolecular multielement is cooperateed with or realizes that multielement collaboration has become current fire-retardant skill by compounding
The hot subject of art research.Research finds that the nitrogenous organic phosphine compound based on triazine ring derivatives has Halogen, low toxicity, divides
The features such as solution temperature is high, machining property is good, fire retardant is not separated out and fire resistance is good, its fire retardant combination can have been given play to
Significant cooperative effect, therefore, the based flame retardant is increasingly subject to people's attention.
The invention discloses a kind of triazine triphenyl phosphinicacid ethyl ester fire retardant combination and its application process, the fire retardant
Triazine triphenyl phosphinicacid ethyl ester in composition contains C-P keys and stable fragrant phosphine key, and decomposition temperature is high, structure is more stable,
More preferably, also containing symmetrical virtue-big conjugated system of phosphine-nitrogen and many ester structures, which has preferable compatibility with material to flame retardant effect.
Synergistic function is produced by the different structure in complex composition, various ignition-proof elements.In burning, fire-retardant unit therein
Plain phosphorus is readily formed densification and uniform polyphosphoric acid diaphragm, and element silicon promotes the silicon-charcoal protective layer to form densification, nitrogen
The multiple fire retardations such as expansion, heat-insulated anoxybiotic, cooling can be played, excellent flame-retarded efficiency is shown.The fire retardant combination is assisted
Same good flame retardation effect, has good compatibility with macromolecular material, and stability is high, is adapted to the high temperature process of material, does not drop
The mechanical strength of low material.And the fire retardant combination preparation method is simple, can be with reduces cost, with well using front
Scape.
The content of the invention
An object of the present invention is to propose a kind of triazine triphenyl phosphinicacid ethyl ester fire retardant combination.The fire retardant
Composition cooperative flame retardant efficiency is high, and Halogen meets environmental requirement, can overcome the deficiencies in the prior art, is widely used as polyester, gathers
The fire retardant of the materials such as urethane, polypropylene, epoxy resin, has good application and development prospect.
Another object of the present invention is to propose a kind of triazine triphenyl phosphinicacid ethyl ester fire retardant combination in polyester
Application process in the materials such as PET, polyester PBT, polyurethane, polypropylene, epoxy resin.
The purpose of the present invention is achieved through the following technical solutions：
A kind of triazine triphenyl phosphinicacid ethyl ester fire retardant combination, it be by melamine cyanurate (abbreviation MCA),
Melamine polyphosphate (abbreviation MPP), 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (abbreviation DOPO), methyl
Any two kinds, three kinds or four kinds in silicic acid pentaerythritol ester (abbreviation PEMS) are with triazine triphenyl phosphinicacid ethyl ester (referred to as
TTPE) compound, be uniformly mixed to prepare with arbitrary proportion, and the weight fraction of TTPE is more than zero.But consider the reduction and resistance of price
Combustion performance, the compound proportion stated by recommendation tables 1.Table 1 accounts for the percentage of fire retardant combination gross weight for each component.
The each formulation ratio table of 1 fire retardant combination of table
The wherein structure of TTPE is shown below：
The structure of MCA is shown below：
The structure of MPP is shown below：
The structure of DOPO is shown below：
The structure of PEMS is shown below：
The application process of fire retardant combination of the present invention as described above, as a example by applying in polyester PET or PBT, which is special
Levy and be, the method is：
Formula 1, formula 2, formula 3, formula 4, formula 5, formula 6 or formula 7 are separately added in polyester PET or PBT
Fire retardant combination, is well mixed, and is molded or extrudes under melt temperature.
Compared with prior art, the beneficial effects of the present invention is：
1. the TTPE in fire retardant combination of the present invention is many phosphorus of many aromatic ring macromoleculars, many nitrogen, many ester compounds, with high score
Sub- material has good compatibility, it is easy to disperse, and does not separate out, and does not reduce the mechanical strength of material.
2. fire retardant of the invention does not contain halogen, meets environmental requirement, has good application and development prospect.
3. the fire retardant combination that the present invention is provided, containing phosphorus, nitrogen or element silicon, can produce synergistic fire retardation, to poly-
Ester PET, PBT have good flame-retarded efficiency.
4. the preparation method of the fire retardant combination that the present invention is provided is simple, and equipment investment is few, low production cost, using side
Just.
Specific embodiment
Embodiment is given below so that the present invention is further illustrated, but it need to be pointed out that following examples are not understood that
For limiting the scope of the invention, person skilled in the art's the above of the invention of this area is made to the present invention
Some nonessential modifications and adaptations still fall within protection scope of the present invention.
Embodiment 1 adds TTPE, MCA and DOPO of different proportion in polyester PET, stirs, and is squeezed with XJ-01 types
Go out the batten that machine extrudes diameter about 3mm under melt temperature, its limited oxygen index is surveyed with HC900-2 type oxygen index measurers, tie
Fruit is shown in Table 2.
2 TTPE of table and MCA and DOPO is compounded to the fire-retardant data of PET
Embodiment 2 adds TTPE, MCA and PEMS of different proportion in polyester PET, stirs, and is squeezed with XJ-01 types
Go out the batten that machine extrudes diameter about 3mm under melt temperature, its limited oxygen index is surveyed with HC900-2 type oxygen index measurers, tie
Fruit is shown in Table 3.
3 TTPE of table and MCA and PEMS is compounded to the fire-retardant data of PET
Embodiment 3 adds TTPE, MPP and DOPO of different proportion in polyester PET, stirs, and is squeezed with XJ-01 types
Go out the batten that machine extrudes diameter about 3mm under melt temperature, its limited oxygen index is surveyed with HC900-2 type oxygen index measurers, tie
Fruit is shown in Table 4.
4 TTPE of table and MPP and DOPO is compounded to the fire-retardant data of PET
Embodiment 4 adds TTPE, MPP and PEMS of different proportion in polyester PET, stirs, and is squeezed with XJ-01 types
Go out the batten that machine extrudes diameter about 3mm under melt temperature, its limited oxygen index is surveyed with HC900-2 type oxygen index measurers, tie
Fruit is shown in Table 5.
5 TTPE of table and MPP and PEMS is compounded to the fire-retardant data of PET
Embodiment 5 adds TTPE, MCA, DOPO and PEMS of different proportion in polyester PET, stirs, uses XJ-01
Type extruder extrudes the batten of diameter about 3mm under melt temperature, surveys its limit oxygen with HC900-2 type oxygen index measurers and refers to
Number, the results are shown in Table 6.
6 TTPE of table is compounded to the fire-retardant data of PET with MCA, DOPO and PEMS
Embodiment 6 adds TTPE, MPP, DOPO and PEMS of different proportion in polyester PET, stirs, uses XJ-01
Type extruder extrudes the batten of diameter about 3mm under melt temperature, surveys its limit oxygen with HC900-2 type oxygen index measurers and refers to
Number, the results are shown in Table 7.
7 TTPE of table is compounded to the fire-retardant data of PET with MPP, DOPO and PEMS
Embodiment 7 adds TTPE, MCA, MPP, DOPO and PEMS of different proportion in polyester PET, stirs, and uses
XJ-01 types extruder extrudes the batten of diameter about 3mm under melt temperature, surveys its limit with HC900-2 type oxygen index measurers
Oxygen index (OI), the results are shown in Table 8.
8 TTPE of table is compounded to the fire-retardant data of PET with MCA, MPP, DOPO and PEMS
Embodiment 8 adds TTPE, MCA and DOPO of different proportion in polyester PBT, stirs, and is squeezed with XJ-01 types
Go out the batten that machine extrudes diameter about 3mm under melt temperature, its limited oxygen index is surveyed with HC900-2 type oxygen index measurers, tie
Fruit is shown in Table 9.
9 TTPE of table and MCA and DOPO is compounded to the fire-retardant data of PBT
Embodiment 9 adds TTPE, MCA and PEMS of different proportion in polyester PBT, stirs, and is squeezed with XJ-01 types
Go out the batten that machine extrudes diameter about 3mm under melt temperature, its limited oxygen index is surveyed with HC900-2 type oxygen index measurers, tie
Fruit is shown in Table 10.
10 TTPE of table and MCA and PEMS is compounded to the fire-retardant data of PBT
Embodiment 10 adds TTPE, MPP and DOPO of different proportion in polyester PBT, stirs, and is squeezed with XJ-01 types
Go out the batten that machine extrudes diameter about 3mm under melt temperature, its limited oxygen index is surveyed with HC900-2 type oxygen index measurers, tie
Fruit is shown in Table 11.
11 TTPE of table and MPP and DOPO is compounded to the fire-retardant data of PBT
Embodiment 11 adds TTPE, MPP and PEMS of different proportion in polyester PBT, stirs, and is squeezed with XJ-01 types
Go out the batten that machine extrudes diameter about 3mm under melt temperature, its limited oxygen index is surveyed with HC900-2 type oxygen index measurers, tie
Fruit is shown in Table 12.
12 TTPE of table and MPP and PEMS is compounded to the fire-retardant data of PBT
Embodiment 12 adds TTPE, MCA, DOPO and PEMS of different proportion in polyester PBT, stirs, uses XJ-
01 type extruder extrudes the batten of diameter about 3mm under melt temperature, surveys its limit oxygen with HC900-2 type oxygen index measurers and refers to
Number, the results are shown in Table 13.
13 TTPE of table is compounded to the fire-retardant data of PBT with MCA, DOPO and PEMS
Embodiment 13 adds TTPE, MPP, DOPO and PEMS of different proportion in polyester PBT, stirs, uses XJ-
01 type extruder extrudes the batten of diameter about 3mm under melt temperature, surveys its limit oxygen with HC900-2 type oxygen index measurers and refers to
Number, the results are shown in Table 14.
14 TTPE of table is compounded to the fire-retardant data of PBT with MPP, DOPO and PEMS
Embodiment 14 adds TTPE, MCA, MPP, DOPO and PEMS of different proportion in polyester PBT, stirs, and uses
XJ-01 types extruder extrudes the batten of diameter about 3mm under melt temperature, surveys its limit with HC900-2 type oxygen index measurers
Oxygen index (OI), the results are shown in Table 15.
15 TTPE of table is compounded to the fire-retardant data of PBT with MCA, MPP, DOPO and PEMS
Claims (2)
1. a kind of triazine triphenyl phosphinicacid ethyl ester fire retardant combination, it is characterised in that the fire retardant combination is by trimerization
Cyanamide cyanurate (abbreviation MCA), melamine polyphosphate (abbreviation MPP) and the miscellaneous -10- phospho hetero phenanthrenes of 9,10- dihydro-9-oxy -
Any two in 10- oxides (abbreviation DOPO) or three kinds and triazine triphenyl phosphinicacid ethyl ester (abbreviation TTPE) and methyl silicon
Sour pentaerythritol ester (abbreviation PEMS) is compounded, is uniformly mixed to prepare with arbitrary proportion, and the weight fraction of TTPE and PEMS is more than
Zero,
The wherein structure of TTPE is shown below：
The structure of MCA is shown below：
The structure of MPP is shown below：
The structure of DOPO is shown below：
The structure of PEMS is shown below：
2. a kind of application process of triazine triphenyl phosphinicacid ethyl ester fire retardant combination according to claim 1, its feature
Be, in polyester PET or PBT add different proportion TTPE, MCA, DOPO and PEMS or add different proportion TTPE,
TTPE, MCA, MPP, DOPO and PEMS of MPP, DOPO and PEMS or addition different proportion, is well mixed, and is molded under melt temperature
Or extrusion.
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Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109517009A (en) * | 2018-10-23 | 2019-03-26 | 苏州科技大学 | Three silicon cage alcohol ester compounds of fire retardant phosphorous acid and preparation method thereof |
| CN109400652A (en) * | 2018-10-23 | 2019-03-01 | 苏州科技大学 | Organic silicon-phosphorus fire retardant tricresyl phosphate silicon cage alcohol ester compounds and preparation method thereof |
| CN109485677A (en) * | 2018-10-23 | 2019-03-19 | 苏州科技大学 | Organic silicon-phosphorus fire retardant diphenyl phosphonic acid silicon cage alcohol ester compounds and preparation method thereof |
| CN109575078A (en) * | 2018-10-23 | 2019-04-05 | 苏州科技大学 | Organic silicon-phosphorus sulphur fire retardant tri o cresyl thiophosphate silicon cage alcohol ester compounds and preparation method thereof |
| CN115073522B (en) * | 2022-07-20 | 2022-11-18 | 上海沪正纳米科技有限公司 | Compound containing silicon, phosphorus and nitrogen based on DOPO group and preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3410809A (en) * | 1965-05-28 | 1968-11-12 | Monsanto Res Corp | Cn compounds |
| WO2006130353A2 (en) * | 2005-05-31 | 2006-12-07 | Eastman Kodak Company | Light-emitting device containing bis-phosphineoxide compound |
| CN103254233A (en) * | 2013-06-05 | 2013-08-21 | 苏州科技学院 | Ethyl triazinyl triphenyl hypophosphite compound and preparation method thereof |
-
2014
- 2014-09-26 CN CN201410507953.7A patent/CN104231312B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3410809A (en) * | 1965-05-28 | 1968-11-12 | Monsanto Res Corp | Cn compounds |
| WO2006130353A2 (en) * | 2005-05-31 | 2006-12-07 | Eastman Kodak Company | Light-emitting device containing bis-phosphineoxide compound |
| CN103254233A (en) * | 2013-06-05 | 2013-08-21 | 苏州科技学院 | Ethyl triazinyl triphenyl hypophosphite compound and preparation method thereof |
Non-Patent Citations (2)
| Title |
|---|
| 1,3,5-Triazines. III. Arbuzov reactions of chlorotriazines;W. Hewertson et al.;《Journal of the Chemical Society》;19631231;1670-1675 * |
| 2,4,6-三(O,O-二甲基磷酰基)-1,3,5-三嗪的合成及表征;王彦林,等;《兰州理工大学学报》;20100630;第36卷(第3期);78-80 * |
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