CN107501545A - A kind of low regain Flameproof polyamide and preparation method thereof - Google Patents
A kind of low regain Flameproof polyamide and preparation method thereof Download PDFInfo
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- CN107501545A CN107501545A CN201710706205.5A CN201710706205A CN107501545A CN 107501545 A CN107501545 A CN 107501545A CN 201710706205 A CN201710706205 A CN 201710706205A CN 107501545 A CN107501545 A CN 107501545A
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- IFOHSHVURIKZEJ-FPLPWBNLSA-N CCCCCC/C=C\C[F](CCC(O)=O)(O)=O Chemical compound CCCCCC/C=C\C[F](CCC(O)=O)(O)=O IFOHSHVURIKZEJ-FPLPWBNLSA-N 0.000 description 1
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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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/42—Polyamides containing atoms other than carbon, hydrogen, oxygen, and nitrogen
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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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
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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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K2003/026—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
- 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
- C08L2203/00—Applications
- C08L2203/20—Applications use in electrical or conductive gadgets
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyamides (AREA)
Abstract
The invention discloses a kind of low regain Flameproof polyamide and preparation method thereof.The preparation method of the low regain Flameproof polyamide comprises the following steps：Phosphonium flame retardant, Long carbon chain diamine and dihydric alcohol obtain fire retardant performed polymer through prepolymerization reaction and polymerisation successively in water；Fire retardant performed polymer produces with polyamide 66 salt through copolyreaction.Long carbon chain diamine, dihydric alcohol and phosphonium flame retardant polymeric flame-retardant agent performed polymer of the present invention, polymerize to obtain low regain Flameproof polyamide copolymer with polyamide 66 performed polymer, obtain that mechanical property is good, regain is low and fire-retardant polyamide.Low regain Flameproof polyamide provided by the invention is applied in fields such as space flight and aviation, electronic apparatus.The low regain Flameproof polyamide of the present invention, its good flame resistance, regain are low, Halogen no red phosphorus is environment-friendly, mechanical performance is excellent.Preparation method provided by the invention, the polyamide material technique of preparation is simple, mechanical property is good, regain is low and fire-retardant, is adapted to large-scale promotion.
Description
Technical field
The present invention relates to a kind of low regain Flameproof polyamide and preparation method thereof, belong to Polymer Synthesizing field.
Background technology
Polyamide (popular name nylon) be in engineering plastics using at most, purposes is maximum, kind is most complete, cost performance is best, comprehensive
A kind of thermoplastic of function admirable is closed, it is very extensive in the application of the parts such as electronics, electrical equipment, high power transformation.The fire-retardant side of polyamide
Method typically uses blending method or copolymerization method, and blending method is big in the presence of flame retardant amount is added, and material mechanical performance is influenceed after addition big
The problems such as；And the problems such as complex process, reaction controlling are difficult, reactive flame retardant species is few be present in copolymerization method, while either
Blending method or copolymerization method all have polar group after fire retardant is added to be increased, so as to cause the water imbibition of Flameproof polyamide to carry
Height, high insulation applications are made a big impact.
Existing literature and patent retrieval are found, Chinese patent CN105086436A disclose by fire retardant red phosphorus and its
Fire-resistant polyamide is made in master batch or bromide fire retardant blending, and blending method is big in the presence of flame retardant amount is added, to material power after addition
The problems such as performance impact is big is learned, and it is bigger from fire retardant pollution, mutually speeded with present green chemical concept back of the body road；It is Chinese special
Sharp CN103387666A and 200510002204.6 prepares polyamide nano-composite using melamine, cyanuric acid as raw material,
It is big to remain addition flame retardant amount, material mechanical performance is influenceed after addition big；Chinese patent CN1266445A discloses " polymerization
The fire-retardant combination of thing bound non-halogen ", fire-retardant polyamides is obtained using reactive flame retardant CEPPA and polyamide 66 monomer copolymerization
The polymer of amine 66, the fire retardant CEPPA of response type are copolymerized in polyamide polymer strand so that original polyamide 66 gathers
Compound anti-flammability improves, but causes fire-retardant unit because temperature is too high with process without solving to polymerize in polyamide 66
Decomposition technique problem；Chinese patent CN104746168A, CN104762689A disclose polyamide 6 and polyamide 66 using fire-retardant
Chloromethyl phenyl phosphinic acids are made with thionyl chloride, ether reaction in agent hydroxymethyl phenyl phosphinic acids, and then resistance is made in aminating reaction again
Performed polymer aminomethyl phenyl phosphinic acid is fired, the problems such as whole technological process is complicated, reaction controlling difficulty, it is steady that Flameproof polyamide is made
It is qualitative not high enough.
Chinese patent CN100352862C and CN101787204B patent by co polystyrene resin and its derivative come
The water imbibition of polyamide is reduced, Chinese patent CN104250377A patents reduce polyamide by being copolymerized aromatic acid
Water imbibition.And above-mentioned is to cause the reduction of polyamide flexibility come modified polyamide by aromatic series and its derivative.Chinese patent
CN103073877B improves low water absorption Flameproof polyamide, but its fire retardant adds a large amount of using the method for blending, this method
Fire retardant makes material mechanical performance be deteriorated.
To sum up, although there is the relevant report of low water absorption polyamide and fire-retardant polyamide material, there is not yet with excellent
The low regain Flameproof polyamide of different combination property.
The content of the invention
It is an object of the invention to provide a kind of low regain Flameproof polyamide and preparation method thereof, to solve to overcome blending method
The middle a large amount of fire retardants of addition cause to reduce material mechanical performance problem.
The preparation method of low regain Flameproof polyamide provided by the present invention, comprises the following steps：
(1) phosphonium flame retardant, Long carbon chain diamine and dihydric alcohol obtain through prepolymerization reaction and polymerisation successively in water
Fire retardant performed polymer；
(2) the fire retardant performed polymer produces the low regain Flameproof polyamide with polyamide 66 salt through copolyreaction.
In above-mentioned preparation method, in step (1), the weight average molecular weight of the fire retardant performed polymer can be 3000~
5000。
In above-mentioned preparation method, in step (1), before the prepolymerization reaction, methods described also includes will be described phosphorous
Fire retardant, the Long carbon chain diamine, the dihydric alcohol and the water mix the step of 0.5~1h, so that it is well mixed；
The prepolymerization reaction and the polymerisation are carried out in an inert atmosphere, are carried out such as in nitrogen atmosphere.
In above-mentioned preparation method, in step (1), the temperature of the prepolymerization reaction can be 50~90 DEG C, concretely 50
~70 DEG C, 50 DEG C, 70 DEG C or 90 DEG C, the time can be 0.5~1.5h, concretely 0.5~1h；
The temperature of the polymerisation can be 180~190 DEG C, concretely 180 DEG C, 185 DEG C or 190 DEG C, and the time can be 1
~2h, concretely 1h, 1.5h or 1~1.5h；
The polymerisation can be carried out under 0.25~0.4MPa pressure, concretely 0.3MPa.
In above-mentioned preparation method, in step (1), the phosphonium flame retardant, the Long carbon chain diamine, the dihydric alcohol
Mol ratio with the water can be 1：1.1~1.2：1：50~100, concretely 1：1.1：1：50、1：1.1：1：100 or 1：
1.2：1：70.
In above-mentioned preparation method, in step (1), the phosphonium flame retardant can be CEPPA, DDP or their derivative；
The structural formula of the CEPPA is as shown in formula I：
The derivative of the CEPPA is the sodium salt or sylvite of the CEPPA, is reacted by the CEPPA and NaOH or KOH
Arrive；
The structural formula of the DDP is as shown in formula II：
The derivative of the DDP is the sodium salt or sylvite of the DDP, reacts to obtain by the DDP and NaOH or KOH.
In above-mentioned preparation method, in step (1), the Long carbon chain diamine can be 11 carbon diamines, 12 carbon diamines,
13 carbon diamines or 14 carbon diamines；
The dihydric alcohol can be the dihydric alcohol that carbon number is 5~10.
In above-mentioned preparation method, in step (2), the copolyreaction is carried out in accordance with the following steps：
The aqueous solution of polyamide 66 salt is carried out under conditions of temperature is 200~210 DEG C, pressure is 1.7~2.2MPa
Heat-insulation pressure keeping processing；After pressure release to normal pressure, the fire retardant performed polymer is added, the copolyreaction is carried out after heating.
In above-mentioned preparation method, the mass fraction of the aqueous solution of the polyamide 66 salt is 70~85%, such as by quality
It is 80% that the aqueous solution for the polyamide 66 salt that fraction is 52% is concentrated into mass fraction at 150 DEG C；
The addition of the fire retardant performed polymer can be the gross weight of the fire retardant performed polymer and the polyamide 66 salt
4~15%, concretely 4~10%, 10~15%, 4%, 10% or 15%；
The time of the heat-insulation pressure keeping processing can be 1.5h~2h；
The temperature of the copolyreaction can be 240~250 DEG C, and the time can be 0.5~1h.
In above-mentioned preparation method, after the copolyreaction terminates, methods described also includes heating up and the step of vacuumize,
Then discharging pelletizing obtains product of cutting into slices；
Temperature after the heating can be 260~275 DEG C, and it can be 30~50min to extract the time, and the vacuum after extraction can
For 0.01~50KPa.
The low regain Flameproof polyamide that the above method of the present invention obtains falls within protection scope of the present invention.
The Limiting Oxygen Value number for the low regain Flameproof polyamide of section product that the present invention obtains is 28~32, is had fire-retardant
Property；Regain is less than 2%；It can be seen that the low regain Flameproof polyamide of the present invention both ensure that fire resistance, solves sucking nylon again
The problems such as water rate is high, while using the flame-proof environmental protection system of Halogen no red phosphorus, meet high-end Flameproof polyamide engineering plastics requirement.
The present invention has the advantages that：
The present invention is pre- with polyamide 66 by Long carbon chain diamine, dihydric alcohol and phosphonium flame retardant polymeric flame-retardant agent performed polymer
Aggressiveness polymerize to obtain low regain Flameproof polyamide copolymer, obtains that mechanical property is good, regain is low and fire-retardant polyamide.
Low regain Flameproof polyamide provided by the invention is applied in fields such as space flight and aviation, electronic apparatus.
The low regain Flameproof polyamide of the present invention, its good flame resistance, regain are low, Halogen no red phosphorus is environment-friendly, mechanical
Excellent performance.
Preparation method provided by the invention, the polyamide material technique of preparation is simple, mechanical property is good, regain is low and
It is fire-retardant, it is adapted to large-scale promotion.
Embodiment
Experimental method used in following embodiments is conventional method unless otherwise specified.
Material used, reagent etc., unless otherwise specified, are commercially obtained in following embodiments.
Regain is tested according to standard GB/T/T 6503-2008 in following embodiments.
Embodiment 1, prepare low regain Flameproof polyamide
1st, the polymerization of fire retardant performed polymer
CEPPA, 11 carbon diamines, penta binary alcohol and water mixing 0.5h, its molar ratio are 1：1.1：1：50 inputs are extremely
In reactor, 0.5h is mixed, is warming up under 50 DEG C of nitrogen protective conditions, stir lower progress prepolymerization reaction 0.5h.In prepolymerization reaction
Afterwards, 0.3MPa is pressurized to, further heats up polymerisation under nitrogen protection, 1h is reacted under the conditions of being 180 DEG C in temperature, obtains
Fire retardant performed polymer, weight average molecular weight 3000.
2nd, low regain Flameproof polyamide polymerization
In 52wt% polyamide 66 saline solution input reactor, by 52wt% polyamide 66 water under the conditions of 150 DEG C
Solution salt is concentrated to 80wt%, is warming up to 200 DEG C, boosting pressurize to 1.7MPa, after dwell time 1.5h, pressure release to normal pressure；It is high
Speed stirring, addition account for the 4wt% fire retardant performed polymers of percentage by weight, and then heating carries out copolyreaction, and temperature rises to 240
DEG C, reaction time 1h；Reaction temperature rises to 260 DEG C and starts to vacuumize, and reaction vacuum is 0.01KPa, extract the time be
30min.Obtain low moisture regain Flameproof polyamide copolymer, discharging, section, packaging；It is 28 to finally obtain fire-retardant slice oxygen value number, is returned
Damp rate is 2% low regain Flameproof polyamide.
The mechanical property of low regain Flameproof polyamide section manufactured in the present embodiment is as shown in table 1.
Embodiment 2, prepare low regain Flameproof polyamide
1st, fire retardant performed polymer polymerize
DDP sodium salt, 12 carbon diamines, appoint dihydric alcohol and water mixing 0.5h, its molar ratio is 1：1.1：1：100 throw
Enter into reactor, under 70 DEG C of nitrogen protective conditions, stir lower progress prepolymerization reaction 1h.After prepolymerization reaction, it is pressurized to
0.3MPa, polymerization is further heated up under nitrogen protection, react 1h under the conditions of being 185 DEG C in temperature, obtain fire retardant performed polymer,
Weight average molecular weight is 4000.
2nd, low regain Flameproof polyamide polymerization
In 52wt% polyamide 66 saline solution input reactor, by 52wt% polyamide 66 water under the conditions of 150 DEG C
Solution salt is concentrated to 80wt%, is warming up to 205 DEG C, boosting pressurize to 2.0MPa, after dwell time 2h, pressure release to normal pressure；At a high speed
Stirring, addition account for 10% fire retardant performed polymer of percentage by weight, then temperature reaction, and temperature rises to 245 DEG C, the reaction time
For 1h；Reaction temperature rises to 270 DEG C and starts to vacuumize, and reaction vacuum is 20KPa, and the extraction time is 40min.Obtain low time
Tide-bound retardant polyamide copolymer, discharging, section, packaging, it is 30 to finally obtain fire-retardant slice oxygen value number, and regain is 1.8%
Low regain Flameproof polyamide.
The mechanical property of low regain Flameproof polyamide section manufactured in the present embodiment is as shown in table 1.
Embodiment 3, prepare low regain Flameproof polyamide
1st, fire retardant performed polymer polymerize
DDP, 14 carbon diamines, certain herbaceous plants with big flowers dihydric alcohol and water mixing 1h, its ratio are 1：1.2：1：70 put into reactor,
Under 90 DEG C of nitrogen protective conditions, lower progress prepolymerization reaction 1h is stirred.After stirring reaction, 0.3MPa is pressurized to, is protected in nitrogen
Polymerization is further heated up under shield, 1.5h is reacted under the conditions of being 190 DEG C in temperature, obtains fire retardant performed polymer, weight average molecular weight is
5000。
2nd, low regain Flameproof polyamide polymerization
In 52wt% polyamide 66 saline solution input reactor, by 52wt% polyamide 66 water under the conditions of 150 DEG C
Solution salt is concentrated to 80wt%, is warming up to 210 DEG C, boosting pressurize to 2.2MPa, after dwell time 2h, pressure release to normal pressure；At a high speed
Stirring, addition account for 15% fire retardant performed polymer of percentage by weight, then temperature reaction, and temperature rises to 250 DEG C, the reaction time
For 1h；Reaction temperature rises to 275 DEG C and starts to vacuumize, and reaction vacuum is 50KPa, and the extraction time is 50min.Obtain low time
Tide-bound retardant polyamide copolymer, discharging, section, packaging, it is 32 to finally obtain fire-retardant slice oxygen value number, and regain is 1.9%
Low regain Flameproof polyamide.
The mechanical property of low regain Flameproof polyamide section manufactured in the present embodiment is as shown in table 1.
The low moisture regain fire-retardant nylon section index of table 1
It can be seen from the data in table 1 present invention be prepared low regain Flameproof polyamide good flame resistance, return
Damp rate is low, and has excellent mechanical property, meets the needs of high-end electronic, film, fiber etc..
Above example is only to introduce the preferred case of the present invention, to those skilled in the art, without departing substantially from this
Any obvious changes and improvements carried out in the range of spirit, it is regarded as the part of the present invention.
Claims (10)
1. a kind of preparation method of low regain Flameproof polyamide, comprises the following steps：
(1) phosphonium flame retardant, Long carbon chain diamine and dihydric alcohol obtain through prepolymerization reaction and polymerisation fire-retardant successively in water
Agent performed polymer；
(2) the fire retardant performed polymer produces the low regain Flameproof polyamide with polyamide 66 salt through copolyreaction.
2. preparation method according to claim 1, it is characterised in that：It is described before the prepolymerization reaction in step (1)
Method also includes the step that the phosphonium flame retardant, the Long carbon chain diamine, the dihydric alcohol and the water are mixed to 0.5~1h
Suddenly；
The prepolymerization reaction and the polymerisation are carried out in an inert atmosphere.
3. preparation method according to claim 1 or 2, it is characterised in that：In step (1), the temperature of the prepolymerization reaction
For 50~90 DEG C, the time is 0.5~1.5h；
The temperature of the polymerisation is 180~190 DEG C, and the time is 1~2h；
The polymerisation is carried out under 0.25~0.4MPa pressure.
4. according to the preparation method any one of claim 1-3, it is characterised in that：In step (1), the phosphor-containing flame-proof
Agent, the Long carbon chain diamine, the mol ratio of the dihydric alcohol and the water are 1：1.1~1.2：1：50~100.
5. according to the preparation method any one of claim 1-4, it is characterised in that：In step (1), the phosphor-containing flame-proof
Agent is CEPPA, DDP or their derivative；
The structural formula of the CEPPA is as shown in formula I：
The derivative of the CEPPA is the sodium salt or sylvite of the CEPPA；
The structural formula of the DDP is as shown in formula II：
The derivative of the DDP is the sodium salt or sylvite of the DDP.
6. according to the preparation method any one of claim 1-5, it is characterised in that：In step (1), the Long carbon chain two
First amine is 11 carbon diamines, 12 carbon diamines, 13 carbon diamines or 14 carbon diamines；
The dihydric alcohol is the dihydric alcohol that carbon number is 5~10.
7. according to the preparation method any one of claim 1-6, it is characterised in that：In step (2), the copolyreaction
Carry out in accordance with the following steps：
The aqueous solution of polyamide 66 salt is incubated under conditions of temperature is 200~210 DEG C, pressure is 1.7~2.2MPa
Pressurize is handled；After pressure release to normal pressure, the fire retardant performed polymer is added, the copolyreaction is carried out after heating.
8. preparation method according to claim 7, it is characterised in that：The mass fraction of the aqueous solution of the polyamide 66 salt
For 70~85%；
The addition of the fire retardant performed polymer be the gross weight of the fire retardant performed polymer and the polyamide 66 salt 4~
15%；
The time of the heat-insulation pressure keeping processing is 1.5h~2h；
The temperature of the copolyreaction is 240~250 DEG C, and the time is 0.5~1h.
9. the preparation method according to claim 7 or 8, it is characterised in that：After the copolyreaction terminates, methods described is also
The step of including heating up and vacuumizing；
Temperature after the heating is 260~275 DEG C, and the extractions time is 30~50min, the vacuum after extraction for 0.01~
50KPa。
10. low regain Flameproof polyamide prepared by method any one of claim 1-9.
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| WO2020224378A1 (en) * | 2019-05-09 | 2020-11-12 | 金发科技股份有限公司 | Flame-retardant semi-aromatic polyamide and preparation method therefor |
| CN112144141A (en) * | 2020-09-15 | 2020-12-29 | 东华大学 | Copolymerized flame-retardant polyamide fiber and preparation method thereof |
| CN116120544A (en) * | 2023-02-01 | 2023-05-16 | 中化学科学技术研究有限公司 | Melamine flame-retardant composition and preparation method thereof |
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Cited By (5)
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| WO2020224378A1 (en) * | 2019-05-09 | 2020-11-12 | 金发科技股份有限公司 | Flame-retardant semi-aromatic polyamide and preparation method therefor |
| CN112144141A (en) * | 2020-09-15 | 2020-12-29 | 东华大学 | Copolymerized flame-retardant polyamide fiber and preparation method thereof |
| CN112144141B (en) * | 2020-09-15 | 2021-10-26 | 东华大学 | Copolymerized flame-retardant polyamide fiber and preparation method thereof |
| CN116120544A (en) * | 2023-02-01 | 2023-05-16 | 中化学科学技术研究有限公司 | Melamine flame-retardant composition and preparation method thereof |
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Application publication date: 20171222 |