CN107501566A - A kind of DOPO bases dissaving structure phosphateng halogen-free flame retardant and preparation method thereof - Google Patents
A kind of DOPO bases dissaving structure phosphateng halogen-free flame retardant and preparation method thereof Download PDFInfo
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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
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/002—Dendritic macromolecules
- C08G83/005—Hyperbranched macromolecules
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- 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
- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
- C08G79/02—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing phosphorus
- C08G79/04—Phosphorus linked to oxygen or to oxygen and carbon
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/10—Homopolymers or copolymers of propene
- C08L23/12—Polypropene
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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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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08L2201/22—Halogen free composition
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Abstract
The present invention relates to a kind of DOPO bases dissaving structure phosphateng halogen-free flame retardant and preparation method thereof, belong to phosphonium flame retardant technical field.The method of the present invention as reaction member and then prepares high phosphorus content dissaving structure phosphate flame retardant using two kinds of phosphorous-containing monomers DOPO bases intermediates and POCl3, reaches the purpose that fire retardant phosphorus content is improved while obtaining macromolecular fire retardant.The present invention efficiently solves current small molecule phosphonium flame retardant poor compatibility and the routinely low deficiency of hyperbranched fire retardant phosphorus content, synthesized fire retardant has high phosphorus content, HMW, it is high, good with ignition resistant substrate compatibility with flame retarding efficiency, it is not easy to migrate the advantages that.
Description
Technical field
The present invention relates to a kind of DOPO bases dissaving structure phosphateng halogen-free flame retardant and preparation method thereof, belong to phosphorous resistance
Fire agent technical field.
Background technology
High polymer material has the advantages that density is small, specific strength is high, toughness is high and fatigue durability is good, packaging, building,
Mechanical industry etc. is widely used.But high polymer material is mostly made up of C, H, O element, causes high polymer material generally to be deposited
Inflammable the defects of.In recent years, the fire triggered by high polymer material takes place frequently, and the security of the lives and property to people causes seriously
Threaten, therefore it is most important to carry out flame retardant treatment to it.
Nearly ten years, the focus of flame-retardant modified always polymer composite research is carried out to inflammable high polymer material,
All kinds fire retardant is developed and is applied to flame retarded polymeric material, wherein halogen type fire retardant is fire-retardant compared to other types
Agent has higher flame retarding efficiency and good with the compatibility of polymer base material, but halogen flame-retardant system is in the mistake of decomposition combustion
With the release of the toxic gases such as hydrogen halides, dioxin and dibenzofurans in journey, infringement is brought to human body and environment,
Therefore limited and use by presently relevant regulation.Fire retardant it is non-halogen be the development of current fire retardant general trend, phosphorus flame retardant
As the important branch in fire retardant, it can play flame retardant effect in condensed phase and gas phase, and with low cigarette, low toxicity and
The advantages that environment-friendly high-efficiency, by the widely studied of lot of domestic and foreign scholar.At present, the flame retarding efficiency of phosphonium flame retardant how is improved
So as to reduce the addition of fire retardant to material performance impact itself；How the compatibility of fire retardant and ignition resistant substrate is improved so as to carry
High fire-retardance stability, it is two focuses of fire retardant research.
The content of P elements of the phosphonium flame retardant flame retarding efficiency with fire retardant in itself is directly related, in order to improve phosphor-containing flame-proof
Agent phosphorus element content, numerous researchers make extensive work.Miscellaneous -10- phospho hetero phenanthrenes -10- the oxides of 9,10- dihydro-9-oxies
Abbreviation DOPO, it is a kind of BACN intermediate.DOPO has higher phosphorus content in itself, and phosphorus group is with ring-type O=
The mode of P-O keys introduces, and than in general, cyclic organophosphorus ester heat endurance and chemical stability be not high, and fire resistance is more
It is good, DOPO groups are introduced into fire retardant to the phosphorus element content that can increase in fire retardant, reach the fire-retardant effect for improving fire retardant
The effect of rate.Chinese patent application publication number CN105254678A discloses one kind by the miscellaneous -10- phosphas of 9,10- dihydro-9-oxies
The method that phenanthrene -10- oxides (DOPO) base intermediate prepares high phosphorus content fire retardant with phosphorus oxychloride reaction.This method is by two kinds
Phosphorous unit is combined by chemically reacting, and prepares the small molecule fire retardant of high phosphorus content.Although the fire retardant has higher
Phosphorus content, but itself molecular weight is relatively low, causes it to be applied to poor compatibility after high polymer material, easily produces migration and analysis
Go out, fire-retardant stability Shortcomings are carried out to high polymer material.
Increase flame retardant molecule amount is to improve fire retardant and the effective method of polymer base material compatibility, and increases resistance
Combustion agent molecule amount can be realized by the method for synthesis of super branched type aggretion type fire retardant.Chinese patent application publication number
CN101880393A and CN103881076A discloses several hyperbranched non-halogen phosphoric acid ester combustion inhibitor preparation method, synthesized
Fire retardant there is the advantages of degree of branching is high and molecular weight amount is big, it is compatible with institute ignition resistant substrate that fire retardant can be effectively improved
Property, but the A that two patents are announcedxByIt is phosphorous unit there was only one kind in the construction unit A and B of type branched polymer, causes this
The phosphorus content of a little hyperbranched poly mould assembly fire retardants is relatively low, and flame retarding efficiency is relatively low.
The content of the invention
It is poor and hyperbranched with substrate compatibility the invention aims to solve the high phosphonium flame retardant of current small molecule
The problem of type phosphonium flame retardant phosphorus content is low, there is provided a kind of DOPO bases dissaving structure phosphateng halogen-free flame retardant and its preparation side
Method.The synthetic method as reaction member and then is prepared height and contained using two kinds of phosphorous-containing monomers DOPO bases intermediates and POCl3
Phosphorus amount dissaving structure phosphate flame retardant, reach the purpose that fire retardant phosphorus content is improved while obtaining macromolecular fire retardant.
The purpose of the present invention is achieved through the following technical solutions.
A kind of DOPO bases dissaving structure phosphateng halogen-free flame retardant, its general structure are as follows：
Wherein R structures are any one in following structure：
A kind of preparation method of DOPO bases dissaving structure phosphateng halogen-free flame retardant, is comprised the following steps that：
Step 1: under the protection of inert gas, 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO)
It is 70-110 in temperature with 4,4'-Dihydroxybenzophenone (DHBP) or to benzaldehyde (TPA) or parahydroxyben-zaldehyde (PHBA)
DEG C atent solvent in occur electrophilic addition reaction, filter out reaction product after reacting 3-6h and washed repeatedly with anhydrous inert solvent
Wash for several times, be then dried under reduced pressure 2-4h in 60-100 DEG C of vacuum drying oven, obtain DOPO base intermediates.Specific reaction equation
It is as follows：
Miscellaneous -10- phospho hetero phenanthrenes -10- the oxides (DOPO) of 9,10- dihydro-9-oxies and 4,4 '-dihydroxy benaophenonel
(DHBP) it is or to benzaldehyde (TPA) reaction mol ratio 1:0.4~0.5；
Miscellaneous -10- phospho hetero phenanthrenes -10- the oxides (DOPO) of 9,10- dihydro-9-oxies are anti-with parahydroxyben-zaldehyde (PHBA)
It is 1 to answer mol ratio:0.9~1；
The atent solvent is toluene or benzene, using preceding by removing water pre-treatment；
The inert gas is nitrogen or argon gas.
Step 2: under inert gas shielding, the DOPO bases intermediate obtained by step 1 is with POCl3 in acid binding agent
Reacted in existing solvent, product is filtered out after reacting 4-10h and washed repeatedly with solvent, then in 100-120 DEG C
Vacuum drying oven in be dried under reduced pressure 2-6h, DOPO base dissaving structure phosphateng halogen-free flame retardants, specific reaction equation is made
It is as follows：
Wherein R structures are one kind in following structure：
The mol ratio of the DOPO bases intermediate and POCl3 is 3:2；
The acid binding agent is triethylamine or pyridine, and acid binding agent addition is not less than the 20% of POCl3 molal quantity；
The solvent is acetonitrile or dioxane, using preceding by except water process；
The inert gas is nitrogen or argon gas；
The DOPO bases dissaving structure phosphateng halogen-free flame retardant number-average molecular weight is 9000~30000.
Beneficial effect
1st, the preparation method of DOPO bases dissaving structure phosphateng halogen-free flame retardant provided by the present invention, is efficiently solved
Small molecule phosphonium flame retardant poor compatibility and the conventional hyperbranched low deficiency of fire retardant phosphorus content at present, synthesized fire retardant
With high phosphorus content, HMW, there is the advantages that flame retarding efficiency is high, good with ignition resistant substrate compatibility, not easy to migrate.
2nd, preparation method is simple, and fire retardant yield is high, and cost is low, and reaction condition is easily controllable.
3rd, highly effective flame-retardant polypropylene.Fire retardant PDPH is applied to polypropylene flame redardant, it is polyacrylic when addition is 8%
Vertical combustion grade brings up to UL-94V-0 ranks from the off grade of virgin pp；Limited oxygen index from virgin pp 17.3%
It is promoted to 31.7%.
Embodiment
Embodiment is provided so that the invention will be further described below in conjunction with experimental result of the present invention.
Embodiment 1：
A kind of DOPO bases dissaving structure phosphateng halogen-free flame retardant, its general structure are as follows：
Wherein R is following structure：
A kind of preparation method of DOPO bases dissaving structure phosphateng halogen-free flame retardant, is comprised the following steps that：
(1) intermediate DOPO-phOH synthesis
Measure 4,4 '-dihydroxy benaophenonel 21.40g (0.10mol), DOPO 47.52g (0.22mol) and without water beetle
Benzene solvent 350mL, it is added in the 500mL reaction vessels with thermometer, agitator, condenser pipe and protection gas inlet and outlet,
It is passed through under conditions of nitrogen, after reacting 2h at 80 DEG C, 110 DEG C of reaction 2h.Obtained sediment is filtered while hot, and with without water beetle
Benzene is washed 2 times, and white powdery solid product 52.45g, yield 81.2% are obtained after 100 DEG C of dry 2h in vacuum drying oven.
(2) synthesis of DOPO bases dissaving structure phosphate PDPH fire retardants
According to POCl3 and DOPO-phOH intermediates 2：3 mol ratio, weigh DOPO-phOH intermediates 19.38g
(0.03mol), POCl3 3.06g (0.02mol), acid binding agent triethylamine 1.01g (0.01mol) and anhydrous dioxane are molten
Agent 200mL, it is added in the 250mL reaction vessels with condenser pipe, agitator, thermometer and protection gas inlet and outlet.In nitrogen
Under environment, after reacting 2h at 80 DEG C, 100 DEG C of reaction 8h.After reaction terminates, obtained sediment is filtered while hot, and with anhydrous
Dioxane washs for several times, the dry 2-4h of 90 DEG C of vacuum drying oven.Faint yellow PDPH fire retardants solid product is obtained after drying
12.53g。
Flame retardant molecule amount is measured using GC-1690 model gel osmoticing chromatogram analysis instrument (GPC), measured fire-retardant
Agent PDPH weight average molecular weight is 17500g/mol, number-average molecular weight 9670g/mol, polydispersity coefficient 1.81.
It is as fire retardant, 4,4' diaminodiphenyl sulfone (DDS) using the dissaving structure phosphate PDPH prepared in this implementation
Curing agent, prepare using polypropylene as matrix, fire retardant addition is respectively 0%, 2%, 4% and 8% polypropylene flame redardant sample.
After tested fire retardant in polypropylene addition be 4%, 8% when, polyacrylic vertical combustion grade i.e. can reach UL-94V-1
With V-0 ranks；Limited oxygen index is promoted to 28.6 and 31.7 from non-antiflaming polyacrylic 17.3.The specific flame retardant effect such as institute of table 1
Show.
The fire retardant PDPH polypropylene flame redardant effects of table 1
Embodiment 2：
A kind of DOPO bases dissaving structure phosphateng halogen-free flame retardant, its general structure are as follows：
Wherein R is following structure：
A kind of preparation method of DOPO bases dissaving structure phosphateng halogen-free flame retardant, is comprised the following steps that：
(1) intermediate DOPO-TPA synthesis
Measure terephthalaldehyde 13.13g (0.10mol), DOPO 45.36g (0.21mol) and anhydrous benzene solvent
300mL, it is added in the 500mL reaction vessels with thermometer, agitator, condenser pipe and protection gas inlet and outlet, is being passed through nitrogen
Under conditions of gas, after reacting 4h at 70 DEG C, 80 DEG C of reaction 1h.Obtained sediment is filtered while hot, and 1 is washed with anhydrous benzene
It is secondary, obtain white powdery solid product 50.05g, yield 88.9% after 70 DEG C of dry 3h in vacuum drying oven.
(2) synthesis of DOPO bases dissaving structure phosphate PDTA fire retardants
According to POCl3 and DOPO-TPA intermediates 2：3 mol ratio, weigh above-mentioned intermediate 16.89g
(0.03mol), POCl3 3.06g (0.02mol), acid binding agent pyridine 1.60g (0.02mol) and anhydrous acetonitrile solvent
200mL, it is added in the 250mL reaction vessels with condenser pipe, agitator, thermometer and protection gas inlet and outlet.In nitrogen ring
Under border, after reacting 2h at 60 DEG C, 80 DEG C of reaction 10h.After reaction terminates, obtained sediment is filtered while hot, and with anhydrous second
Nitrile washs 2 times, the dry 1-3h of 70 DEG C of vacuum drying oven.Yellow PDTA fire retardant solid products 11.93g is obtained after drying.
Flame retardant molecule amount is measured using GC-1690 model gel osmoticing chromatogram analysis instrument (GPC), measured fire-retardant
Agent PDPH weight average molecular weight is 21080g/mol, number-average molecular weight 17600g/mol, polydispersity coefficient 1.19.
Embodiment 3：
A kind of DOPO bases dissaving structure phosphateng halogen-free flame retardant, its general structure are as follows：
Wherein R is following structure：
A kind of preparation method of DOPO bases dissaving structure phosphateng halogen-free flame retardant, is comprised the following steps that：
(1) intermediate DOPO-PHBA synthesis
Measure parahydroxyben-zaldehyde 12.21g (0.10mol), DOPO 45.36g (0.21mol) and dry toluene solvent
200mL, it is added in the 500mL reaction vessels with thermometer, agitator, condenser pipe and protection gas inlet and outlet, is being passed through nitrogen
Under conditions of gas, after reacting 1h at 100 DEG C, 110 DEG C of reaction 2h.Obtained sediment is filtered while hot, and washed with dry toluene
Wash 2 times, white granular solid product 44.04g, yield 79.5% are obtained after 100 DEG C of dry 4h in vacuum drying oven.
(2) synthesis of DOPO bases dissaving structure phosphate PDHA fire retardants
According to POCl3 and DOPO-PHBA intermediates 2：3 mol ratio, weigh above-mentioned intermediate 16.62g
(0.03mol), POCl3 3.06g (0.02mol), acid binding agent triethylamine 2.11g (0.021mol) and anhydrous acetonitrile solvent
200mL, it is added in the 250mL reaction vessels with condenser pipe, agitator, thermometer and protection gas inlet and outlet.In nitrogen ring
Under border, after reacting 2h at 60 DEG C, 80 DEG C of reaction 7h.After reaction terminates, obtained sediment is filtered while hot, and use anhydrous acetonitrile
Washing 2 times, the dry 2-4h of 70 DEG C of vacuum drying oven.White PDHA fire retardants solid product 10.82 is obtained after drying.
Flame retardant molecule amount is measured using GC-1690 model gel osmoticing chromatogram analysis instrument (GPC), measured fire-retardant
Agent PDPH weight average molecular weight is 42150g/mol, number-average molecular weight 26900g/mol, polydispersity coefficient 1.57.
Claims (6)
- A kind of 1. DOPO bases dissaving structure phosphateng halogen-free flame retardant, it is characterised in that：Its general structure is as follows：Wherein R structures are any one in following structure：
- A kind of 2. preparation method of DOPO bases dissaving structure phosphateng halogen-free flame retardant, it is characterised in that：Comprise the following steps that：Step 1: under the protection of inert gas, 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide and 4,4 '-dihydroxy Base benzophenone or to benzaldehyde or parahydroxyben-zaldehyde, it is anti-to occur electrophilic addition in the atent solvent that temperature is 70-110 DEG C Should, filter out reaction product after reacting 3-6h and washed repeatedly with anhydrous inert solvent for several times, then in 60-100 DEG C of vacuum 2-4h is dried under reduced pressure in baking oven, obtains DOPO base intermediates；Miscellaneous -10- phospho hetero phenanthrenes -10- the oxides of 9,10- dihydro-9-oxies It is 1 with 4,4 '-dihydroxy benaophenonel or to benzaldehyde reaction mol ratio:0.4~0.5；The 9,10- dihydro-9-oxies are miscellaneous- 10- phospho hetero phenanthrene -10- oxides are 1 with parahydroxyben-zaldehyde reaction mol ratio:0.9~1；Step 2: under inert gas shielding, the DOPO bases intermediate obtained by step 1 is deposited with POCl3 in acid binding agent Solvent in reacted, react 4-10h after product is filtered out, then washed repeatedly with solvent, then at 100-120 DEG C 2-6h is dried under reduced pressure in vacuum drying oven, DOPO base dissaving structure phosphateng halogen-free flame retardants are made；The DOPO bases intermediate Mol ratio with POCl3 is 3:2；The acid binding agent is triethylamine or pyridine, and acid binding agent addition rubs not less than POCl3 The 20% of that number.
- 3. a kind of preparation method of DOPO bases dissaving structure phosphateng halogen-free flame retardant as claimed in claim 2, its feature It is：Atent solvent described in step 1 is toluene or benzene, using preceding by removing water pre-treatment.
- 4. a kind of preparation method of DOPO bases dissaving structure phosphateng halogen-free flame retardant as claimed in claim 2, its feature It is：The inert gas is nitrogen or argon gas.
- 5. a kind of preparation method of DOPO bases dissaving structure phosphateng halogen-free flame retardant as claimed in claim 2, its feature It is：Solvent described in step 2 is acetonitrile or dioxane, using preceding by except water process.
- 6. a kind of preparation method of DOPO bases dissaving structure phosphateng halogen-free flame retardant as claimed in claim 2, its feature It is：The DOPO bases dissaving structure phosphateng halogen-free flame retardant number-average molecular weight is 9000~30000.
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Cited By (8)
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| CN109942829A (en) * | 2019-03-13 | 2019-06-28 | 江南大学 | A kind of preparation method and application of three-source integrated hyperbranched expandable type fire retardant |
| CN110105395A (en) * | 2019-04-16 | 2019-08-09 | 皖西学院 | A kind of pyridine fire retardant and its preparation method and application |
| CN112175310A (en) * | 2020-10-16 | 2021-01-05 | 张雪飞 | Phosphorus-containing flame-retardant rigid polypropylene material and preparation method thereof |
| CN112442077A (en) * | 2019-08-28 | 2021-03-05 | 广东广山新材料股份有限公司 | Phosphorus-containing flame retardant with reactive groups and preparation method and application thereof |
| CN114656702A (en) * | 2022-05-10 | 2022-06-24 | 安徽永正密封件有限公司 | Flame-retardant rubber for building safety net and preparation method thereof |
| CN115286926A (en) * | 2022-10-09 | 2022-11-04 | 赢胜节能集团股份有限公司 | Retractable high-elastic damping rubber-plastic plate |
| CN116180296A (en) * | 2023-01-04 | 2023-05-30 | 江苏瑞洋安泰新材料科技有限公司 | Antibacterial fabric and preparation method thereof |
| CN117586472A (en) * | 2024-01-19 | 2024-02-23 | 广东荣昌纺织实业有限公司 | Terylene double-sided coating type flame-retardant waterproof tarpaulin, coating composition and preparation method thereof |
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109942829A (en) * | 2019-03-13 | 2019-06-28 | 江南大学 | A kind of preparation method and application of three-source integrated hyperbranched expandable type fire retardant |
| CN109942829B (en) * | 2019-03-13 | 2020-03-06 | 江南大学 | Preparation method and application of three-source integrated hyperbranched intumescent flame retardant |
| CN110105395A (en) * | 2019-04-16 | 2019-08-09 | 皖西学院 | A kind of pyridine fire retardant and its preparation method and application |
| CN112442077A (en) * | 2019-08-28 | 2021-03-05 | 广东广山新材料股份有限公司 | Phosphorus-containing flame retardant with reactive groups and preparation method and application thereof |
| CN112175310A (en) * | 2020-10-16 | 2021-01-05 | 张雪飞 | Phosphorus-containing flame-retardant rigid polypropylene material and preparation method thereof |
| CN114656702A (en) * | 2022-05-10 | 2022-06-24 | 安徽永正密封件有限公司 | Flame-retardant rubber for building safety net and preparation method thereof |
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Application publication date: 20171222 |