CN109111571A - Containing triazine-phosphorus schiff bases fire retardant and its synthetic method - Google Patents
Containing triazine-phosphorus schiff bases fire retardant and its synthetic method Download PDFInfo
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- CN109111571A CN109111571A CN201810793295.0A CN201810793295A CN109111571A CN 109111571 A CN109111571 A CN 109111571A CN 201810793295 A CN201810793295 A CN 201810793295A CN 109111571 A CN109111571 A CN 109111571A
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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
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/527—Cyclic esters
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- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
- C08G73/0644—Poly(1,3,5)triazines
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- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
- C08G73/065—Preparatory processes
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Abstract
The present invention relates to a kind of containing triazine-phosphorus schiff bases fire retardant and its synthetic method, and the schiff bases flame retardant mechanism formula containing triazine-phosphorus is
Description
Technical field
The invention belongs to the technical fields of expansion type flame-retarding product, specifically, the present invention relates to a kind of containing triazine-phosphorus
Schiff bases fire retardant and its synthetic method.
Background technique
Polyethylene (PE), polypropylene (PP) and its composite material are widely applied in daily life.But they are all easy
Therefore burning is restricted in the high field application of flame-retardancy requirements, becomes inevitable to the flame-retardant modified of them.It is the most commonly used
Method be additive flame retardant in the substrate, easy to operate, significant effect.
Most common additive flame retardant is inorganic hydroxide (such as magnesium hydroxide, aluminium hydroxide), phosphonium flame retardant, contains
Nitrogen combustion inhibitor, Silicone-containing Flame Retardant, halogen containing flame-retardant and expansion type flame retardant etc..
Inorganic fire retardants has environmental protection characteristic such as magnesium hydroxide, aluminium hydroxide, but flame retarding efficiency is low, and additive amount is big,
The performance of science of composite material is influenced big.
Halogen containing flame-retardant, especially bromide fire retardant, the fire-retardant application field with very high flame retarding efficiency and wide spectrum, but
It is that this based flame retardant can be released in burning and processing with the big dioxin of corrosive hydrogen halides and toxicity and a large amount of
Smog causes the secondary pollution of environment, therefore, is highly desirable exploitation Halogen efficient flame-retarding agent.
Expansion type flame retardant (IFR) is to develop swift and violent environment-friendly type non-bittern combustion inhibitor now, it can form cause in burning
Close and expansion layer of charcoal, reduces the release of flue gas, prevents the generation of molten drop phenomenon, and it is poly- to be widely used in polyethylene, polypropylene etc.
Close the flame-retardant modified of object.Expansion type flame retardant is usually made of acid source, carbon source and gas source.Common carbon forming agent be pentaerythrite,
The polyols such as dipentaerythritol, starch, such carbon forming agent is water-soluble big, and thermal stability is not high, is easy in process
The problems such as with polyphosphoric acids reactant salt.1- oxygroup phospha -4- methylol -2,6,7- trioxa-l-phosphabicyclo [2.2.2] octane (PEPA)
It is the modified compound of pentaerythrite, there is relatively small water-soluble, very high charring rate, and contain phosphorus, have good
Flame retardant effect.
Triazine derivative is a kind of compound for being rich in tertiary carbon structure, has excellent carbon-forming performance.Chinese patent text
It offers and discloses the carbon forming agent patent application document of three parts of triazines, in which: portion is Publication No. CN101586033A, invention name
Referred to as " triazine carbon forming agent of the chain structure containing aromatic series and preparation method thereof ", portion are that notification number is CN100500657C, invents
Entitled " triazine series oligomer and its synthetic method ", portion is Patent No. ZL200510010243.4, entitled " big
Molecule triazine series carbon forming foaming agent and its synthetic method " "；They all have preferably at charcoal effect, but its there are heat resistance and
At the not high problem of charcoal.
Schiff bases is a kind of compound containing C=N double bond, has simple, the higher thermostabilization of product for preparing reaction condition
Property, and can neutralization activity free radical in pyrolytic process.Chinese patent literature discloses the patent application document of two parts of schiff bases,
Portion is Publication No. CA103073727A, and portion is Publication No. CN 106008993A, and char yield and heat resistance are also not
It is very high.
Summary of the invention
The purpose of the present invention is the problems that the char yield for existing schiff bases carbon forming agent is not high, flame retardant property is bad to mention
And for a kind of containing triazine-phosphorus schiff bases fire retardant and its synthetic method, operation is easy, and products therefrom of the present invention has neat coal amout
Higher, better heat stability, flame retarding efficiency are higher.
In order to achieve the above object, the technical solution of the schiff bases fire retardant of the invention containing triazine-phosphorus is realized in
, which is characterized in that structural formula is as follows:
In formula: R is one of straight chained alkyl, phenyl or the phenyl with substituent group containing 2-18 carbon；
R1 be to phenyl, phenyl, adjacent phenyl or with hydroxyl, methyl to phenyl, phenyl, adjacent phenyl.
In order to achieve the above object, the synthetic method of the schiff bases fire retardant of the invention containing triazine-phosphorus is realized in
, which is characterized in that it comprises the following steps:
Step 1
Solvent is added in container, Cyanuric Chloride (CNC) and 1- oxygroup phospha -4- methylol -2,6,7- are added in a reservoir
Trioxa-l-phosphabicyclo [2.2.2] octane (PEPA), is cooled in 0-45 DEG C and is dispersed with stirring in water-bath or oil bath, is gradually added dropwise and ties up
Sour agent reacts 1-4 hours, obtains unitary substituent (CNC-PEPA)；Wherein Cyanuric Chloride (CNC), 1- oxygroup phospha -4- hydroxyl first
The molar ratio of base -2,6,7- trioxa-l-phosphabicyclo [2.2.2] octane (PEPA) and acid binding agent three are 1:1:1, three polychlorostyrene of 1mol
The solvent of cyanogen 50-500ml；
Step 2
Band diamine is added in another container to be uniformly mixed with solvent and acid binding agent, temperature is controlled to 45-60 DEG C, is slowly added dropwise
The unitary substituent solution (CNC-PEPA) that step 1 obtains reacts 3-6 hours；It then proceedes to be warming up to 100-130 DEG C, reaction
3-6 hours, obtain the diamines intermediate (CNC-PEPA-2A) containing triazine and phosphorus；Wherein unitary substituent (CNC-PEPA), binary
The molar ratio of amine and acid binding agent is 1:2:2；The solvent of unitary substituent (CNC-PEPA) 50-500ml of 1mol；
Step 3
In the container of step 2, it is directly added into the solution of dialdehyde, is heated to 100 ~ 150 DEG C, reacts 2-10 hours, is sunk
Shallow lake, by solvent washing, distillation water washing, vacuum drying to get to containing triazine-phosphorus schiff bases fire retardant.
In the technical scheme, Step 1: solvent used in step 2 is acetonitrile, acetone, tetrahydrofuran, two
The mixed liquor of one or both of six ring methylene chloride of oxygen, chloroform；
In the technical scheme, the solvent used in step 3 is acetonitrile, acetone, tetrahydrofuran, dioxane, diformazan
The mixed liquor of one or both of sulfoxide, N,N-dimethylformamide, methylene chloride, chloroform, ethyl alcohol, methanol；
In the technical scheme, the acid binding agent used in step 1 and step 2 is triethylamine, pyridine, triethylene two
One of amine or their mixture.
Synthetic route of the invention is as follows:
Compared with prior art, the present invention having the advantage that
1) it uses and contains triazine and PEPA structure, and combined with schiff bases, prepare line style contains triazine-phosphorus schiff bases fire retardant,
Give full play to triazine ring, PEPA, schiff bases thermal stability and at charcoal effect and phosphorus catalysis carbon-forming function, thus obtain more
High charring rate and flame retarding efficiency is conducive to improve thermal stability；
2) PEPA is introduced into fire retardant systems, while playing carbon forming agent, water resistance and flame retardant property can be improved, it is phosphorous
Compound can form PO free radical, capture the free radical of gas phase, to play fire retardation, can also be formed in combustion more
Polyphosphoric acid promotes into charcoal；Therefore, C=N double bond and PEPA are introduced into the same molecular structure, and it is good to obtain carbon-forming performance
Fire retardant, operation be easy；
3) product is white or buff powder, and yield has 90% or more compared with high heat resistance temperature and charring rate, weightlessness 5%
Temperature is more than 280 DEG C, and 600 DEG C of residual volume reaches 30% or more.
Specific implementation method
Below with reference to embodiment, the invention will be further described.It should be noted that saying for these embodiments
It is bright to be used to help understand the present invention, but and do not constitute a limitation of the invention.In addition, each implementation of invention described below
Involved technical characteristic can be combined with each other as long as they do not conflict with each other in mode.
Embodiment one
It is a kind of synthetic method of schiff bases fire retardant containing triazine-phosphorus, and synthesis step is as follows:
Step 1
The acetonitrile of 50mL is added in the there-necked flask of 500mL, 18.45 g(0.1mol are added) Cyanuric Chloride (CNC), it is cooling
To in 10 DEG C and being dispersed with stirring, by 1- oxygroup phospha -4- methylol -2,6 of 18.0 g(0.1 mol), 7- trioxa-l-phosphabicyclo
[2.2.2] octane (PEPA) is dissolved in the acetonitrile of 100mL and is slowly dropped in there-necked flask, meanwhile, 10.11 g are added dropwise
The triethylamine of (0.1mol) reacts 3 hours, obtains unitary substituent (CNC-PEPA)；
Step 2
12.02 g(0.2 mol are added in another container) ethylenediamine mixed with the triethylamine of 20.22 g(0.2 mol)
Even, temperature controls the unitary substituent solution (CNC-PEPA) that step 1 acquisition is slowly added dropwise to 50 DEG C, reacts 4 hours；Then
Continue to be warming up to 110 DEG C, reacts 6 hours, obtain the diamines intermediate (CNC-PEPA-2A) containing triazine and phosphorus；
Step 3
In the container of step 2, be directly added into 13.41 g(0.1 mol) terephthalaldehyde solution, be heated to 120 DEG C,
Reaction 5 hours, obtains light-yellow precipitate, contains three by acetonitrile washing, distillation water washing, vacuum drying to get to of the invention
Piperazine-phosphorus schiff bases fire retardant (CAP1), 43.75 g, yield are 92.5 %.Product structure formula is as follows:
Structural formula 1:CAP1 structural formula
In the present embodiment, Step 1: acetonitrile used in step 2 can use acetone, tetrahydrofuran, dioxane, dichloromethane
The mixed liquor of one or both of alkane, chloroform replaces；Acetonitrile used in step 3 can use acetone, tetrahydro furan
It mutters, the mixed liquor of one or both of dioxane, methylene chloride, chloroform replaces.
In the present embodiment, triethylamine used in step 1 and step 2 can use pyridine, triethylene
One of diamines or their mixture replace.
TGA analysis the result shows that: CAP1 in nitrogen temperature of initial decomposition (by weightlessness 5% calculate) be 314 DEG C, 600 DEG C
When participation rate be 35.2%, illustrate CAP1 has good thermal stability and preferably at charcoal.
Elemental analysis result: each element mass fraction is C(51.0%), N(20.1%), H(5.1%) and, O(17.1%), with reason
It is consistent by calculated result.
ICP test result are as follows: P content 6.8%, it is consistent with the calculated results (6.6%).
Embodiment two
It is a kind of synthetic method of schiff bases fire retardant containing triazine-phosphorus, and synthesis step is as follows:
Step 1
The acetone of 50mL is added in the there-necked flask of 500mL, 18.45 g(0.1mol are added) Cyanuric Chloride (CNC), it is cooling
To in 30 DEG C and being dispersed with stirring, by 1- oxygroup phospha -4- methylol -2,6 of 18.0 g(0.1 mol), 7- trioxa-l-phosphabicyclo
[2.2.2] octane (PEPA) is dissolved in the acetone of 100mL and is slowly dropped in there-necked flask, meanwhile, 11.22 g are added dropwise
The triethylenediamine of (0.1mol) reacts 1 hour, obtains unitary substituent (CNC-PEPA)；
Step 2
176.3 g(0.2 mol are added in another container) butanediamine and 22.44 g(0.2 mol) triethylenediamine
It is uniformly mixed, temperature controls the unitary substituent solution (CNC-PEPA) that step 1 acquisition is slowly added dropwise to 60 DEG C, and reaction 3 is small
When；It then proceedes to be warming up to 130 DEG C, reacts 3 hours, obtain the diamines intermediate (CNC-PEPA-2A) containing triazine and phosphorus；
Step 3
In the container of step 2, be directly added into 13.41 g(0.1 mol) m-terephthal aldehyde solution, be heated to 150 DEG C,
Reaction 3 hours, obtains yellow mercury oxide, by acetone washing, distillation water washing, vacuum drying to get to containing triazine-phosphorus Schiff
Alkali fire retardant (CAP2), 48.55 g, yield are 93.2 %.Product structure formula is as follows:
Structural formula 2:CAP2 structural formula
In the present embodiment, Step 1: acetone used in step 2 can use acetonitrile, tetrahydrofuran, dioxane, dichloro
The mixed liquor of one or both of methane, chloroform replaces；Acetone used in step 3 can use acetonitrile, tetrahydro furan
It mutters, one of dioxane, dimethyl sulfoxide, N,N-dimethylformamide, methylene chloride, chloroform, ethyl alcohol, methanol or two
The mixed liquor of person replaces.
In the present embodiment, triethylenediamine used in step 1 and step 2 can use three second
One of amine, pyridine or their mixture replace.
TGA analysis the result shows that: CAP2 in nitrogen temperature of initial decomposition (by weightlessness 5% calculate) be 301 DEG C, 600 DEG C
When participation rate be 31.5%, illustrate CAP2 has good thermal stability and preferably at charcoal.
Elemental analysis result: each element mass fraction is C(54.5%), N(19.1%), H(5.0%) and, O(14.9%), with reason
It is consistent by calculated result.
ICP test result are as follows: P content 6.5%, it is consistent with the calculated results (6.0%).
Embodiment three
It is a kind of synthetic method of schiff bases fire retardant containing triazine-phosphorus, and synthesis step is as follows:
Step 1
The dioxane of 100mL is added in the there-necked flask of 500mL, be added 18.45 g(0.1mol) Cyanuric Chloride
(CNC), it is cooled in 20 DEG C and is dispersed with stirring, by 1- oxygroup phospha -4- methylol -2,6 of 18.0 g(0.1 mol), 7- tri-
Oxabicyclo [2.2.2] octane (PEPA) is dissolved in the dioxane of 100mL and is slowly dropped in there-necked flask, meanwhile, drop
Add 7.91 g(0.1mol) pyridine, react 4 hours, obtain unitary substituent (CNC-PEPA)；
Step 2
12.02 g(0.2 mol are added in another container) ethylenediamine be uniformly mixed with the pyridine of 15.82 g(0.2 mol),
Temperature controls the unitary substituent solution (CNC-PEPA) that step 1 acquisition is slowly added dropwise to 45 DEG C, reacts 6 hours；Then after
It is continuous to be warming up to 100 DEG C, it reacts 6 hours, obtains the diamines intermediate (CNC-PEPA-2A) containing triazine and phosphorus；
Step 3
In the container of step 2, be directly added into 15.01 g(0.1 mol) 2- hydroxyl-terephthalaldehyde solution, be heated to
It 100 DEG C, reacts 10 hours, obtains light-yellow precipitate, by dioxane washing, distillation water washing, vacuum drying to get to containing
Triazine-phosphorus schiff bases fire retardant (CAP3), 45.12 g, yield are 92.1 %.Product structure formula is as follows:
Structural formula 3:CAP3 structural formula
In the present embodiment, Step 1: dioxane used in step 2 can use acetonitrile, acetone, tetrahydrofuran, dichloro
The mixed liquor of one or both of methane, chloroform replaces；Dioxane used in step 3 can use acetonitrile, third
One of ketone, tetrahydrofuran, dimethyl sulfoxide, N,N-dimethylformamide, methylene chloride, chloroform, ethyl alcohol, methanol or two
The mixed liquor of person replaces.
In the present embodiment, pyridine used in step 1 and step 2 can use triethylamine, Sanya second
One of base diamines or their mixture replace.
TGA analysis the result shows that: CAP3 in nitrogen temperature of initial decomposition (by weightlessness 5% calculate) be 305 DEG C, 600 DEG C
When participation rate be 32.7%, illustrate CAP3 has good thermal stability and preferably at charcoal.
Elemental analysis result: each element mass fraction is C(47.8%), N(20.5%), H(5.4%) and, O(19.8%), with reason
It is consistent by calculated result.
ICP test result are as follows: P content 6.3%, it is consistent with the calculated results (6.5%).
It is explained in detail in conjunction with the embodiments above, but the present invention is not limited to described embodiment.For ability
For the those of ordinary skill in domain, these embodiments are carried out without departing from the principle and spirit of the present invention a variety of
Variation, modification, replacement and deformation are still fallen within the scope of the present invention.
Claims (3)
1. a kind of containing triazine-phosphorus schiff bases fire retardant, which is characterized in that structural formula is as follows:
In formula: R is one of straight chained alkyl, phenyl or the phenyl with substituent group containing 2-18 carbon；
R1 be to phenyl, phenyl, adjacent phenyl or with hydroxyl, methyl to phenyl, phenyl, adjacent phenyl.
2. the synthetic method of the schiff bases fire retardant according to claim 1 containing triazine-phosphorus, which is characterized in that including such as
Under several steps:
Step 1
Solvent is added in container, Cyanuric Chloride (CNC) and 1- oxygroup phospha -4- methylol -2,6,7- are added in a reservoir
Trioxa-l-phosphabicyclo [2.2.2] octane (PEPA), is cooled in 0-45 DEG C and is dispersed with stirring, and acid binding agent is gradually added dropwise, and reaction 1-4 is small
When, obtain unitary substituent (CNC-PEPA)；Wherein Cyanuric Chloride (CNC), three oxygen of 1- oxygroup phospha -4- methylol -2,6,7-
The molar ratio of miscellaneous bicyclic [2.2.2] octane (PEPA) and acid binding agent three are 1:1:1, and the Cyanuric Chloride of 1mol is with 50-500ml's
Solvent；
Step 2
Band diamine is added in another container to be uniformly mixed with solvent and acid binding agent, temperature is controlled to 45-60 DEG C, is slowly added dropwise
The unitary substituent solution (CNC-PEPA) that step 1 obtains reacts 3-6 hours；It then proceedes to be warming up to 100-130 DEG C, reaction
3-6 hours, obtain the diamines intermediate (CNC-PEPA-2A) containing triazine and phosphorus；Wherein unitary substituent (CNC-PEPA), binary
The molar ratio of amine and acid binding agent is 1:2:2；The solvent of unitary substituent (CNC-PEPA) 50-500ml of 1mol；
Step 3
In the container of step 2, it is directly added into dialdehyde solution, is heated to 100 ~ 150 DEG C, reacts 2-10 hours, is sunk
Shallow lake, by solvent washing, distillation water washing, vacuum drying to get to containing triazine-phosphorus schiff bases fire retardant.
3. the synthetic method of the schiff bases fire retardant according to claim 2 containing triazine-phosphorus, it is characterised in that in step
One, solvent used in step 2 be acetonitrile, acetone, tetrahydrofuran, dioxane, methylene chloride, in chloroform
The mixed liquor of one or both；
The synthetic method of the schiff bases fire retardant according to claim 2 containing triazine-phosphorus, it is characterised in that in step 3
Used solvent is acetonitrile, acetone, tetrahydrofuran, dioxane, dimethyl sulfoxide, N,N-dimethylformamide, dichloromethane
The mixed liquor of one or both of alkane, chloroform, ethyl alcohol, methanol；
The synthetic method of the schiff bases fire retardant according to claim 2 containing triazine-phosphorus, it is characterised in that in step 1 and
Acid binding agent used in step 2 is one of triethylamine, pyridine, triethylenediamine or their mixture.
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Cited By (3)
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| CN111205682A (en) * | 2020-02-24 | 2020-05-29 | 顺德职业技术学院 | UV flame-retardant coating containing ternary-in-one flame retardant and preparation method thereof |
| CN111205715A (en) * | 2020-02-24 | 2020-05-29 | 顺德职业技术学院 | Intumescent flame-retardant coating containing cage-shaped branched chain structure flame retardant and preparation method thereof |
| CN111205714A (en) * | 2020-02-24 | 2020-05-29 | 顺德职业技术学院 | Water-based flame-retardant coating containing three-in-one flame retardant and preparation method thereof |
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| CN111205714A (en) * | 2020-02-24 | 2020-05-29 | 顺德职业技术学院 | Water-based flame-retardant coating containing three-in-one flame retardant and preparation method thereof |
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