CN108503842A - One kind is poly-(Phenyl-phosphonic acid ester-acid amide)Fire retardant, preparation method and its application in the polyester - Google Patents
One kind is poly-(Phenyl-phosphonic acid ester-acid amide)Fire retardant, preparation method and its application in the polyester Download PDFInfo
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- CN108503842A CN108503842A CN201810314627.2A CN201810314627A CN108503842A CN 108503842 A CN108503842 A CN 108503842A CN 201810314627 A CN201810314627 A CN 201810314627A CN 108503842 A CN108503842 A CN 108503842A
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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
- 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
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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
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
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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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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/22—Halogen free composition
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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
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
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- Chemical Kinetics & Catalysis (AREA)
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Abstract
The invention discloses a kind of poly- (phenyl-phosphonic acid esteramides) fire retardant, preparation method and its applications in the polyester, wherein the fire retardant is phosphorous random copolymer, structural formula is as follows:
Description
Technical field
The present invention relates to a kind of poly- (phenyl-phosphonic acid ester-acid amide) fire retardant, preparation method and its application in the polyester,
Belong to halogen-free flame retardants preparation and application field.
Background technology
Polyester material is widely used, and common are aromatic polyester, aliphatic polyester etc..Aromatic polyester thermal stability
Height, mechanical property is good, multi-purpose to make engineering plastics, common are polyethylene terephthalate (PET) and poly terephthalic acid
Butanediol ester (PBT).Aliphatic polyester is biodegradable polymer, environmental-friendly, and development potentiality is huge, such as poly- breast
Acid, poly butylene succinate.However polyesters compound carbon and hydrogen content are high, easy firing, and while burning, is molten with band fire
Drop increases the danger that fire occurs and expands, personnel and property safety is caused with great threat.Thus, we are necessary
Flame retardant treatment is carried out to polyester material.
Common fire retardant is metal time phosphor/phosphine hydrochlorate in polyester material, it can be common that aluminum diethylphosphinate.Diethyl
Base phosphinic acids aluminium phosphorus content is high, good flame resistance, and thermal stability is good, will not all divide under the high processing temperature of PET and PBT
Solution.However, metal phosphinate and polyester matrix poor compatibility, can reduce the mechanical property of material.Phosphorous organic fire-retardant with
Polymer matrix compatability is good, but flame retardant effect is often all barely satisfactory, such as the general phosphorous organic resistance for adding 25-30wt%
Combustion agent could make the PBT battens of 3mm thickness reach UL-94V-0 grades.
Invention content
The present invention is intended to provide a kind of poly- (phenyl-phosphonic acid ester-acid amide) fire retardant, preparation method and its in the polyester
Using.The present invention reacts to form linear polymer with aliphatic dihydroxy alcohol and aromatic diamine using diphenylphosphoryl dichloro, will
When itself and polytetrafluoroethylene (PTFE) compounding are for polyester flame-retardant, there is excellent flame retardant effect, and it and polyester matrix compatibility are good,
It is small to Effect on Mechanical Properties.
Poly- (phenyl-phosphonic acid ester-acid amide) fire retardant of the present invention is a kind of phosphorous random copolymer, the following institute of structural formula
Show:
The degree of polymerization of poly- (phenyl-phosphonic acid ester-acid amide) fire retardant is 5-100.
Wherein, R1For any one of following group:-CH2CH2-、-CH2CH2CH2-、-CH(CH3)-CH2-、
-CH2CH2CH2CH2-、-CH2CH2CH2CH2CH2-、-CH2CH2CH2CH2CH2CH2-。
R2For any one of following group:
The preparation method of poly- (phenyl-phosphonic acid ester-acid amide) fire retardant of the present invention, includes the following steps:
Aliphatic dihydroxy alcohol, aromatic diamine, acid binding agent and solvent are added in reactor, it is small to stir 1-2 at room temperature
When, phenyl phosphonyl chloride then is added dropwise under conditions of ice-water bath, back flow reaction is heated to after dripping off 5-24 hours;Reaction is completed
Afterwards, solvent evaporated adds water to stir 1-2 hours, filters, and washes, dry, obtains poly- (phenyl-phosphonic acid ester-acid amide) fire retardant.
The aliphatic dihydroxy alcohol is selected from ethylene glycol, 1,3- propylene glycol, 1,2- propylene glycol, 1,4- butanediols, 1,5- penta 2
Alcohol or 1,6-HD.
The aromatic diamine is selected from p-phenylenediamine, m-phenylene diamine (MPD), 4,4 '-benzidines, 4,4 '-diamino hexichol
Methane, 4,4 '-diaminodiphenyl ethers or 4,4 '-diaminodiphenylsulfones.
The molar ratio of the aliphatic dihydroxy alcohol and aromatic diamine is 0:1-1:0.
The acid binding agent is selected from pyridine, triethylamine, N, accelerine, sodium hydroxide, potassium hydroxide, sodium carbonate, carbon
Sour potassium, sodium bicarbonate or saleratus.
The molar ratio of the acid binding agent and phenyl phosphonyl chloride is 2:1-3:1.
The solvent is selected from dichloromethane, chloroform, tetrahydrofuran, acetonitrile, ether or acetone, the addition quality of solvent
It is 5-40 times of aliphatic dihydroxy alcohol and aromatic diamine gross mass.
The mole of the phenyl phosphonyl chloride and the ratio between the integral molar quantity of aliphatic dihydroxy alcohol and aromatic diamine are
0.8:1-1:1.2。
The addition quality of water is aliphatic dihydroxy alcohol and aromatic diamine gross mass after the completion of reaction plus when water stirring
2-20 times.
The reaction process of poly- (phenyl-phosphonic acid ester-acid amide) fire retardant of the present invention is as follows:
The application of poly- (phenyl-phosphonic acid ester-acid amide) fire retardant of the present invention, be by it with polytetrafluoroethylene (PTFE) compounding be added to it is poly-
Fire retardant is used as in ester, to improve the flame retardant property and mechanical property of polyester.
The additive amount of poly- (phenyl-phosphonic acid ester-acid amide) fire retardant is the 10-40wt% of polyester quality;Polytetrafluoroethylene (PTFE) adds
Dosage is the 0.1-5wt%, preferably 0.5-1wt% of polyester quality.
The polyester is universal polyester, including PET, PBT, PLA, PBS etc..
Compared with prior art, beneficial effects of the present invention are embodied in:
1, polymeric phosphorus-containing flame retardant preparation method of the invention is simple, easy to implement.
2, when polymeric phosphorus-containing flame retardant and polytetrafluoroethylene (PTFE) of the present invention compounding are for polyester flame-retardant, have excellent fire-retardant
Effect, and it and polyester matrix compatibility are good, it is small to Effect on Mechanical Properties.
Specific implementation mode
Technical scheme of the present invention is further analyzed and described below by specific embodiment.The raw materials used in the present invention
It is all acquisition purchased in market.
Embodiment 1:
By 18.6g (0.3mol) ethylene glycol, 75.7g (0.7mol) p-phenylenediamine, 242.9g (2.4mol) triethylamines and 1L
Chloroform is added in three-necked flask, and stirring is put into after 1 hour in ice-water bath, and 195g (1mol) phenyl phosphonic two is then slowly added dropwise
Chlorine is heated to back flow reaction 12 hours after dripping off;Solvent evaporated after the completion of reaction is added 500mL water and stirs 1 hour, filters, water
It washes for several times, as poly- (phenyl-phosphonic acid ester-acid amide) fire retardant of solid product is obtained after dry.
The structural formula of target product is:
Poly- (phenyl-phosphonic acid ester-acid amide) fire retardant manufactured in the present embodiment and polytetrafluoroethylene (PTFE) are added in PBT, are formulated
For:Poly- (phenyl-phosphonic acid ester-acid amide) fire retardant 15wt%, polytetrafluoroethylene (PTFE) 0.5wt%, PBT84.5wt%.It is vertical through UL-94
The batten of combustion testing, 3.0mm thickness can be tested by V-0 grades, and without melting drippage in combustion process.
Embodiment 2:
108.1g (1mol) p-phenylenediamine, 242.9g (2.4mol) triethylamines and 1L acetonitriles are added in three-necked flask,
Stirring is put into after 1 hour in ice-water bath, and 195g (1mol) phenyl phosphonyl chloride is then slowly added dropwise, and it is anti-that reflux is heated to after dripping off
It answers 12 hours;Solvent evaporated after the completion of reaction is added 500mL water and stirs 1 hour, filter, washed several times with water, solid is obtained after dry
As poly- (phenyl-phosphonic acid ester-acid amide) fire retardant of product.
The structural formula of target product is:
Poly- (phenyl-phosphonic acid ester-acid amide) fire retardant manufactured in the present embodiment and polytetrafluoroethylene (PTFE) are added in PBT, are formulated
For:Poly- (phenyl-phosphonic acid ester-acid amide) fire retardant 15wt%, polytetrafluoroethylene (PTFE) 0.5wt%, PBT84.5wt%.It is vertical through UL-94
The batten of combustion testing, 3.0mm thickness can be tested by V-0 grades, and without melting drippage in combustion process.
Embodiment 3:
By 30.4g (0.4mol) 1,3- propylene glycol, 4,4 '-diaminodiphenylmethane of 119g (0.6mol), 242.9g
(2.4mol) triethylamine and 1L tetrahydrofurans are added in three-necked flask, and stirring is put into after 1 hour in ice-water bath, are then slowly dripped
Add 195g (1mol) phenyl phosphonyl chloride, back flow reaction is heated to after dripping off 12 hours;Solvent evaporated after the completion of reaction is added
500mL water stirs 1 hour, filters, washed several times with water, and it is fire-retardant to obtain solid product as poly- (phenyl-phosphonic acid ester-acid amide) after dry
Agent.
The structural formula of target product is:
Poly- (phenyl-phosphonic acid ester-acid amide) fire retardant manufactured in the present embodiment and polytetrafluoroethylene (PTFE) are added in PBT, are formulated
For:Poly- (phenyl-phosphonic acid ester-acid amide) fire retardant 20wt%, polytetrafluoroethylene (PTFE) 0.5wt%, PBT 79.5wt%.It is vertical through UL-94
The batten of combustion testing, 3.0mm thickness can be tested by V-0 grades, and without melting drippage in combustion process.
Embodiment 4:
By 15.2g (0.2mol) 1,2- propylene glycol, 86.5g (0.8mol) m-phenylene diamine (MPD), 242.9g (2.4mol) triethylamine
It is added in three-necked flask with 1L chloroforms, stirring is put into after 1 hour in ice-water bath, and 195g (1mol) Phenylphosphine is then slowly added dropwise
Acyl dichloro is heated to back flow reaction 12 hours after dripping off;Solvent evaporated after the completion of reaction is added 500mL water and stirs 1 hour, takes out
Filter, washed several times with water obtain as poly- (phenyl-phosphonic acid ester-acid amide) fire retardant of solid product after dry.
The structural formula of target product is:
Poly- (phenyl-phosphonic acid ester-acid amide) fire retardant manufactured in the present embodiment and polytetrafluoroethylene (PTFE) are added in PBT, are formulated
For:Poly- (phenyl-phosphonic acid ester-acid amide) fire retardant 15wt%, polytetrafluoroethylene (PTFE) 0.5wt%, PBT 84.5wt%.It is vertical through UL-94
The batten of combustion testing, 3.0mm thickness can be tested by V-0 grades, and without melting drippage in combustion process.
In order to investigate the mechanical property of obtained flame-retardant polymer of the present invention, now by the part flame-retardant PBT and two in embodiment
The mechanical property of ethylphosphinic acid aluminium flame-retardant PBT is listed as follows:
Note:1, PTFE is polytetrafluoroethylene (PTFE).
Claims (10)
1. a kind of poly- (phenyl-phosphonic acid ester-acid amide) fire retardant, it is characterised in that:The fire retardant is phosphorous random copolymer,
Structural formula is as follows:
Wherein, R1For any one of following group:-CH2CH2-、-CH2CH2CH2-、-CH(CH3)-CH2-、-
CH2CH2CH2CH2-、-CH2CH2CH2CH2CH2-、-CH2CH2CH2CH2CH2CH2-;
R2For any one of following group:
2. poly- (phenyl-phosphonic acid ester-acid amide) fire retardant according to claim 1, it is characterised in that:
The degree of polymerization of poly- (phenyl-phosphonic acid ester-acid amide) fire retardant is 5-100.
3. a kind of preparation method of poly- (phenyl-phosphonic acid ester-acid amide) fire retardant described in claim 1, it is characterised in that including such as
Lower step:
Aliphatic dihydroxy alcohol, aromatic diamine, acid binding agent and solvent are added in reactor, at room temperature stirring 1-2 hours, so
Phenyl phosphonyl chloride is added dropwise under conditions of ice-water bath afterwards, back flow reaction is heated to after dripping off 5-24 hours;After the completion of reaction, steam
Dry solvent adds water to stir 1-2 hours, filters, and washes, dry, obtains poly- (phenyl-phosphonic acid ester-acid amide) fire retardant.
4. preparation method according to claim 3, it is characterised in that:
The aliphatic dihydroxy alcohol be selected from ethylene glycol, 1,3- propylene glycol, 1,2- propylene glycol, 1,4- butanediols, 1,5- pentanediols or
1,6-HD;
The aromatic diamine is selected from p-phenylenediamine, m-phenylene diamine (MPD), 4,4 '-benzidines, 4,4 '-diamino hexichol first
Alkane, 4,4 '-diaminodiphenyl ethers or 4,4 '-diaminodiphenylsulfones.
5. preparation method according to claim 3 or 4, it is characterised in that:
The molar ratio of the aliphatic dihydroxy alcohol and aromatic diamine is 0:1-1:0.
6. preparation method according to claim 3, it is characterised in that:
The acid binding agent be selected from pyridine, triethylamine, N, accelerine, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate,
Sodium bicarbonate or saleratus.
7. preparation method according to claim 3, it is characterised in that:
The solvent is selected from dichloromethane, chloroform, tetrahydrofuran, acetonitrile, ether or acetone, and the addition quality of solvent is fat
5-40 times of fat race dihydric alcohol and aromatic diamine gross mass.
8. preparation method according to claim 3, it is characterised in that:
The molar ratio of the acid binding agent and phenyl phosphonyl chloride is 2:1-3:1;The mole of the phenyl phosphonyl chloride and fat
The ratio between integral molar quantity of race's dihydric alcohol and aromatic diamine is 0.8:1-1:1.2.
9. a kind of application of poly- (phenyl-phosphonic acid ester-acid amide) fire retardant described in claim 1, it is characterised in that:It is by poly- (benzene
Base phosphonic acids ester-acid amide) fire retardant and polytetrafluoroethylene (PTFE) compounding is added in polyester and is used as fire retardant, to improve the anti-flammability of polyester
Energy and mechanical property.
10. application according to claim 9, it is characterised in that:
The additive amount of poly- (phenyl-phosphonic acid ester-acid amide) fire retardant is the 10-40wt% of polyester quality;The additive amount of polytetrafluoroethylene (PTFE)
For the 0.1-5wt% of polyester quality.
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Cited By (5)
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CN109972221A (en) * | 2019-04-09 | 2019-07-05 | 新昌县高纤纺织有限公司 | The weaving preparation method of anti-electrostatic fire retardant non-woven fabrics |
CN110551322A (en) * | 2019-08-22 | 2019-12-10 | 浙江农林大学 | phosphorus-nitrogen oligomer flame retardant and preparation method thereof |
CN109575324B (en) * | 2018-11-28 | 2021-06-22 | 宁波力达得为高分子科技有限公司 | Chemically modified transparent flame-retardant PET master batch and manufacturing method and application thereof |
CN113372550A (en) * | 2021-06-03 | 2021-09-10 | 江南大学 | Flame-retardant plasticizer and flame-retardant polymer-based composite material |
CN113912852A (en) * | 2021-11-18 | 2022-01-11 | 山东艾科高分子材料有限公司 | Preparation method of novel nitrogen-phosphorus flame retardant |
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Cited By (6)
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CN109575324B (en) * | 2018-11-28 | 2021-06-22 | 宁波力达得为高分子科技有限公司 | Chemically modified transparent flame-retardant PET master batch and manufacturing method and application thereof |
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CN113372550A (en) * | 2021-06-03 | 2021-09-10 | 江南大学 | Flame-retardant plasticizer and flame-retardant polymer-based composite material |
CN113912852A (en) * | 2021-11-18 | 2022-01-11 | 山东艾科高分子材料有限公司 | Preparation method of novel nitrogen-phosphorus flame retardant |
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