CN106832404B - Surface migration sex flame retardant of Nitrogen-and Phosphorus-containing and preparation method thereof - Google Patents
Surface migration sex flame retardant of Nitrogen-and Phosphorus-containing and preparation method thereof Download PDFInfo
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- CN106832404B CN106832404B CN201710066383.6A CN201710066383A CN106832404B CN 106832404 B CN106832404 B CN 106832404B CN 201710066383 A CN201710066383 A CN 201710066383A CN 106832404 B CN106832404 B CN 106832404B
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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
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5313—Phosphinic compounds, e.g. R2=P(:O)OR'
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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
- C07F9/657163—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 the ring phosphorus atom being bound to at least one carbon atom
- C07F9/657172—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 the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and one oxygen atom being part of a (thio)phosphinic acid ester: (X = O, S)
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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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- Chemical Kinetics & Catalysis (AREA)
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Abstract
The invention discloses surface migration sex flame retardants of a kind of Nitrogen-and Phosphorus-containing and preparation method thereof, preparation method includes the following steps: (1) by 2, bis- (3- aminophenyl) hexafluoropropane of 2- and pentafluorobenzaldehyde heat in a solvent, after reaction, the reaction system containing intermediate product I is obtained;(2) DOPO is added in the reaction system containing intermediate product I that step (1) obtains and is heated, after reaction, washing, drying obtain the surface migration sex flame retardant of Nitrogen-and Phosphorus-containing.A kind of surface migration sex flame retardant of Nitrogen-and Phosphorus-containing and preparation method thereof, with the increase of phosphorus content in solidfied material, the anti-flammability of solidfied material increases;When flame retardant agent content reaches 5-10%, solidfied material can achieve UL-94, and V-0 grades, good flame retardation effect.The preparation method can quickly produce the surface migration sex flame retardant product of Nitrogen-and Phosphorus-containing, and processing step is succinct, it is easy to accomplish, productivity is high.
Description
Technical field
The present invention relates to technical field of flame retardant, and in particular to a kind of surface migration sex flame retardant of Nitrogen-and Phosphorus-containing and its preparation
Method.
Background technique
Halogenated flame retardant is containing halogens and with a based flame retardant of halogens fire retardation.Four kinds of halogen system
Halogen system element fluorine (F), chlorine (Cl), bromine (Br), iodine (I) all have anti-flammability, and flame retardant effect is successively increased by the sequence of F, Cl, Br, I
By force.It is most strong with iodine flame retardant.In production, only chlorine class and brominated flame retardant are widely used and fluorine class and iodine based flame retardant
Rare application, this is because C-F key is too strong and cannot effectively capture the C-I key of free radical and the fire retardant containing I in fluorine-containing fire retardant
Too weak easily being destroyed affects polymer performance (such as photostability), has lost flame retardant property just below degradation temperature.
9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, abbreviation DOPO contain P-H key in structure, to alkene
Hydrocarbon, epoxide and the great activity of carbonyls can react and generate many derivatives.DOPO and its derivative are due to molecule
Contain cyclohexyl biphenyl, phenanthrene ring, O=P-O key in structure, so there is stronger flame retardant property than common organophosphorus ester.By
Saito reported its synthetic route in 1972 for the first time.DOPO and its derivative can be used as response type and additive flame retardant, close
At fire retardant Halogen, smokeless, nontoxic, do not migrate, flame retardant property is lasting.While improving the flame retardant property of material, not shadow
Ring the mechanical performances such as the mechanical strength of material.It can be used for the multiple materials such as polyamide, linear polyester, polyurethane, epoxy resin
Flame retardant treatment, foreign countries are widely used in the fire-retardant of materials such as pressurized layer, circuit board in plastics for electronics, brass.Although having
Good flame retardant property, but with the increase of additional amount, some detrimental effects can be brought to the performance of material itself.
Summary of the invention
In view of the above deficiencies, it is an object of the present invention to provide a kind of formula is reasonable, it is easy to accomplish, flame retardant effect
The surface migration sex flame retardant of good Nitrogen-and Phosphorus-containing.
The second object of the present invention is, provide it is a kind of can quick Fabrication go out the surface migration sex flame retardant of above-mentioned Nitrogen-and Phosphorus-containing
Preparation method, with the increase of phosphorus content in solidfied material, the anti-flammability of solidfied material increases;When flame retardant agent content reaches 5~
When 10%, solidfied material can achieve UL94, and V-0 grades.
To achieve the above object, the technical solution provided by the present invention is: a kind of surface migration sex flame retardant of Nitrogen-and Phosphorus-containing,
Its structural formula is as follows:
A kind of preparation method of the surface migration sex flame retardant of above-mentioned Nitrogen-and Phosphorus-containing comprising following steps:
(1) bis- (4- aminophenyl) hexafluoropropane of 2,2- and pentafluorobenzaldehyde are heated in a solvent, after reaction, is obtained
Reaction system containing intermediate product I;
(2) DOPO is added in the reaction system containing intermediate product I that step (1) obtains and is heated, after reaction,
Washing, drying, obtain the surface migration sex flame retardant of Nitrogen-and Phosphorus-containing.
Its reaction process are as follows:
As an improvement of the present invention, bis- (4- aminophenyl) hexafluoropropane of 2,2- and phenyl-pentafluoride in the step (1)
The molar ratio of formaldehyde is 1:2.
As an improvement of the present invention, the reaction time is 8~10h in the step (1).
As an improvement of the present invention, heating temperature is 62~68 DEG C in the step (1), preferably, heating temperature
Preferably 65 DEG C.
As an improvement of the present invention, solvent is ethyl alcohol, DMF or DMSO in the step (1).
As an improvement of the present invention, the additional amount of solvent is bis- (the 4- aminophenyls) six of 2,2- in the step (1)
6~12 times of fluoro-propane and pentafluorobenzaldehyde quality sum.
As an improvement of the present invention, mole of the DOPO in the step (2) and the pentafluorobenzaldehyde in step (1)
Than for 1:1.
As an improvement of the present invention, the reaction temperature in the step (2) is 62~68 DEG C, preferably, heating temperature
Preferably 65 DEG C of degree.
As an improvement of the present invention, the reaction time in the step (2) is 4~6h.
The invention has the benefit that the formula of the surface migration sex flame retardant of Nitrogen-and Phosphorus-containing provided by the invention is reasonable, draw
A large amount of fluorine element is entered, can make fire retardant that there is certain surface migration in solidfied material, make fire retardant in solidfied material
Content gradually increase from inside to outside, make solidfied material surface highest containing flame retardant amount, keep its additive amount low, flame retardant effect is excellent;
Although introducing fluorine element on fire retardant simultaneously, free radical cannot be effectively captured since C-F key is too strong, makes fire retardant
With excellent thermal stability;With the increase of phosphorus content in solidfied material, the anti-flammability of solidfied material increases;When flame retardant agent content reaches
To 5~10% when (phosphorus content is 0.25wt%~0.5wt%), solidfied material can achieve UL-94, and V-0 grades, good flame retardation effect.
Preparation method provided by the invention can quickly produce the surface migration sex flame retardant product of Nitrogen-and Phosphorus-containing, and processing step is succinct, easily
In realization, productivity is high.
With reference to the accompanying drawings and examples, the present invention is further described.
Detailed description of the invention
Fig. 1 is nuclear magnetic spectrogram of the invention.
Specific embodiment
A kind of embodiment 1: synthesis step of the surface migration sex flame retardant of Nitrogen-and Phosphorus-containing are as follows:
(1) 145g by the pentafluorobenzaldehyde of bis- (4- aminophenyl) hexafluoropropane of the 2,2- of 11.1g and 13.1g at 65 DEG C
8h is heated in ethyl alcohol, after reaction, obtains the reaction system containing intermediate product I;
(2) DOPO of 14.4g is added in the reaction system containing intermediate product I that step (1) obtains in 65 DEG C of items
4h is heated under part, and after reaction, washing, drying obtain the surface migration sex flame retardant of Nitrogen-and Phosphorus-containing, yield 83.4%.
Its infrared test result is as follows:
FTIR (KBr): N-H stretching vibration peak 3410cm-1, C-N characteristic peak 1288cm-1, P-O-C characteristic peak 1032cm-1,
P-O-Ph characteristic peak 1231cm-1, P-Ph characteristic peak 1595cm-1, P=O characteristic peak 1212cm-1。
Nuclear magnetic spectrogram as shown in Figure 1, nuclear-magnetism test result is as follows:
1H-NMR (400MHz, DMSO-d6) δ 7.50 (k, 2H), 7.30-7.31 (j, 6H), 7.20 (i, 2H), 7.05 (g,
2H), 6.91 (f, 4H), 6.88 (e, 2H), 6.79 (d, 2H), 6.35 (c, 4H), 4.00 (b, 2H), 3.90 (a, 2H).
A kind of embodiment 2: synthesis step of the surface migration sex flame retardant of Nitrogen-and Phosphorus-containing are as follows:
(1) by the pentafluorobenzaldehyde of bis- (4- aminophenyl) hexafluoropropane of the 2,2- of 13.36g and 15.68g at 65 DEG C
10h is heated in 232gDMF, after reaction, obtains the reaction system containing intermediate product I;
(2) DOPO of 17.28g is added in the reaction system containing intermediate product I that step (1) obtains in 65 DEG C of items
6h is heated under part, and after reaction, washing, drying obtain the surface migration sex flame retardant of Nitrogen-and Phosphorus-containing, yield 89.6%.
Its infrared test result is as follows:
FTIR (KBr): N-H stretching vibration peak 3390cm-1, C-N characteristic peak 1268cm-1, P-O-C characteristic peak 1031cm-1,
P-O-Ph characteristic peak 1231cm-1, P-Ph characteristic peak 1595cm-1, P=O characteristic peak 1208cm-1。
A kind of embodiment 3: synthesis step of the surface migration sex flame retardant of Nitrogen-and Phosphorus-containing are as follows:
(1) by the pentafluorobenzaldehyde of bis- (4- aminophenyl) hexafluoropropane of the 2,2- of 8.35g and 9.8g at 65 DEG C
9h is heated in 217.8gDMSO, after reaction, obtains the reaction system containing intermediate product I;
(2) DOPO of 10.8g is added in the reaction system containing intermediate product I that step (1) obtains in 65 DEG C of items
5h is heated under part, and after reaction, washing, drying obtain the surface migration sex flame retardant of Nitrogen-and Phosphorus-containing, yield 87.2%.
Its infrared test result is as follows:
FTIR (KBr): N-H stretching vibration peak 3370cm-1, C-N characteristic peak 1292cm-1, P-O-C characteristic peak 1032cm-1,
P-O-Ph characteristic peak 1231cm-1, P-Ph characteristic peak 1595cm-1, P=O characteristic peak 1215cm-1。
Application Example:
Material is weighed according to table 1:
Table 1
The surface migration sex flame retardant and polystyrene of Nitrogen-and Phosphorus-containing are uniformly mixed;It adds twin-screw extrude, in machine
Under conditions of organizing 200-220 DEG C of temperature, 210 DEG C of die head temperature, screw speed 200rpm, extruding pelletization, then through drying, cool down,
Obtain fire retardant polystyrene sample.UL94 testing vertical flammability is carried out to the sample, as a result shown in table 2:
Table 2
Above-described embodiment is only the preferable embodiment of the present invention, and the present invention cannot enumerate out whole embodiment party
Formula, all technical solutions using one of above-described embodiment, or the equivalent variations done according to above-described embodiment are protected in the present invention
It protects in range.
Specifically, the surface migration sex flame retardant of Nitrogen-and Phosphorus-containing provided by the invention has the advantage that
(1) the surface migration sex flame retardant of a kind of Nitrogen-and Phosphorus-containing of the invention, with the increase of phosphorus content in solidfied material, solidification
The anti-flammability of object increases;When flame retardant agent content reaches 5~10% (phosphorus content 0.25wt%-0.5wt%), solidfied material can be with
Reach UL-94, V-0 grades.
(2) the surface migration sex flame retardant of a kind of Nitrogen-and Phosphorus-containing of the invention, introduces a large amount of fluorine element, can make fire-retardant
Agent has certain surface migration in solidfied material, gradually increases the content of fire retardant in solidfied material from inside to outside, makes solid
Compound surface highest containing flame retardant amount, keeps its additive amount low, flame retardant effect is excellent.
(3) the surface migration sex flame retardant of a kind of Nitrogen-and Phosphorus-containing of the invention, although introducing fluorine element on fire retardant,
It is that cannot effectively capture free radical since C-F key is too strong, makes fire retardant that there is excellent thermal stability.
According to the disclosure and teachings of the above specification, those skilled in the art in the invention can also be to above-mentioned embodiment party
Formula is changed and is modified.Therefore, the invention is not limited to the specific embodiments disclosed and described above, to of the invention
Some modifications and changes should also be as falling into the scope of the claims of the present invention.In addition, although being used in this specification
Some specific terms, these terms are merely for convenience of description, does not limit the present invention in any way.Such as the present invention
Described in above-described embodiment, existed using other fire retardants obtained from same or similar method and component and preparation method thereof
In the scope of the present invention.
Claims (10)
1. a kind of surface migration sex flame retardant of Nitrogen-and Phosphorus-containing, which is characterized in that its structural formula is as follows:
2. a kind of preparation method of the surface migration sex flame retardant of Nitrogen-and Phosphorus-containing described in claim 1, it is characterised in that: it includes
Following steps:
(1) bis- (4- aminophenyl) hexafluoropropane of 2,2- and pentafluorobenzaldehyde are heated in a solvent, after reaction, must be contained
The reaction system of intermediate product I;
(2) DOPO is added in the reaction system containing intermediate product I that step (1) obtains and is heated, after reaction, washed
It washs, dry, obtain the surface migration sex flame retardant of Nitrogen-and Phosphorus-containing.
3. the preparation method of the surface migration sex flame retardant of Nitrogen-and Phosphorus-containing according to claim 2, it is characterised in that: the step
Suddenly bis- (4- aminophenyl) hexafluoropropane of 2,2- and the molar ratio of pentafluorobenzaldehyde are 1:2 in (1).
4. the preparation method of the surface migration sex flame retardant of Nitrogen-and Phosphorus-containing according to claim 2, it is characterised in that: the step
Suddenly the reaction time is 8~10h in (1).
5. the preparation method of the surface migration sex flame retardant of Nitrogen-and Phosphorus-containing according to claim 2, it is characterised in that: the step
Suddenly heating temperature is 62~68 DEG C in (1).
6. the preparation method of the surface migration sex flame retardant of Nitrogen-and Phosphorus-containing according to claim 2, it is characterised in that: the step
Suddenly solvent is ethyl alcohol, DMF or DMSO in (1).
7. the preparation method of the surface migration sex flame retardant of Nitrogen-and Phosphorus-containing according to claim 2, it is characterised in that: the step
Suddenly the additional amount of solvent is 6~12 times of bis- (4- aminophenyl) hexafluoropropane of 2,2- and pentafluorobenzaldehyde quality sum in (1).
8. the preparation method of the surface migration sex flame retardant of Nitrogen-and Phosphorus-containing according to claim 2 or 3, it is characterised in that: institute
The molar ratio for stating the DOPO in step (2) and the pentafluorobenzaldehyde in step (1) is 1:1.
9. the preparation method of the surface migration sex flame retardant of Nitrogen-and Phosphorus-containing according to claim 2, it is characterised in that: the step
Suddenly the reaction temperature in (2) is 62~68 DEG C.
10. the preparation method of the surface migration sex flame retardant of Nitrogen-and Phosphorus-containing according to claim 2, it is characterised in that: described
Reaction time in step (2) is 4~6h.
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CN109280218B (en) * | 2018-08-06 | 2020-03-06 | 厦门大学 | Phosphorus and fluorine-containing flame retardant, preparation method thereof and flame-retardant epoxy resin modified by phosphorus and fluorine-containing flame retardant |
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EP2468814A1 (en) * | 2010-12-22 | 2012-06-27 | Cheil Industries Inc. | Novel Phosphorus Compound, Method of Preparing the Same and Flame Retardant Thermoplastic Resin Composition Including the Same |
CN103044708A (en) * | 2012-12-27 | 2013-04-17 | 清华大学深圳研究生院 | High-efficiency N/P flame retardant, as well as preparation method and application thereof |
CN103865101A (en) * | 2014-02-17 | 2014-06-18 | 清华大学深圳研究生院 | Efficient phosphorus-nitrogen type fire retardant and preparation method thereof |
CN105541917A (en) * | 2016-01-27 | 2016-05-04 | 厦门大学 | Phosphorus and nitrogen cooperated polyester flame retardant and preparation method thereof |
CN105732715A (en) * | 2016-01-27 | 2016-07-06 | 厦门大学 | Phosphorus-containing fluorine-containing synergic flame-retardant compound and preparation method thereof |
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Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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EP2468814A1 (en) * | 2010-12-22 | 2012-06-27 | Cheil Industries Inc. | Novel Phosphorus Compound, Method of Preparing the Same and Flame Retardant Thermoplastic Resin Composition Including the Same |
CN103044708A (en) * | 2012-12-27 | 2013-04-17 | 清华大学深圳研究生院 | High-efficiency N/P flame retardant, as well as preparation method and application thereof |
CN103865101A (en) * | 2014-02-17 | 2014-06-18 | 清华大学深圳研究生院 | Efficient phosphorus-nitrogen type fire retardant and preparation method thereof |
CN105541917A (en) * | 2016-01-27 | 2016-05-04 | 厦门大学 | Phosphorus and nitrogen cooperated polyester flame retardant and preparation method thereof |
CN105732715A (en) * | 2016-01-27 | 2016-07-06 | 厦门大学 | Phosphorus-containing fluorine-containing synergic flame-retardant compound and preparation method thereof |
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