CN109054097A - A kind of cyanurotriamide modified lignin Wrapped up Phosphorus Fire Retardant and its application in ABS resin - Google Patents
A kind of cyanurotriamide modified lignin Wrapped up Phosphorus Fire Retardant and its application in ABS resin Download PDFInfo
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- CN109054097A CN109054097A CN201810899984.XA CN201810899984A CN109054097A CN 109054097 A CN109054097 A CN 109054097A CN 201810899984 A CN201810899984 A CN 201810899984A CN 109054097 A CN109054097 A CN 109054097A
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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
- C08K9/00—Use of pretreated ingredients
- C08K9/10—Encapsulated ingredients
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
- C08H6/00—Macromolecular compounds derived from lignin, e.g. tannins, humic acids
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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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L55/00—Compositions of homopolymers or copolymers, obtained by polymerisation reactions only involving carbon-to-carbon unsaturated bonds, not provided for in groups C08L23/00 - C08L53/00
- C08L55/02—ABS [Acrylonitrile-Butadiene-Styrene] polymers
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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
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
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- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Fireproofing Substances (AREA)
Abstract
The invention discloses a kind of cyanurotriamide modified lignin Wrapped up Phosphorus Fire Retardant and its applications in ABS resin, belong to polymeric material field.The present invention is combined mainly with lignin, aldehyde, melamine, red phosphorus, dispersing agent etc. for raw material using Mannich reaction and chemical coprecipitation, and the cyanurotriamide modified lignin Wrapped up Phosphorus Fire Retardant is made.The cyanurotriamide modified lignin Wrapped up Phosphorus Fire Retardant of the present invention can significantly improve the surface nature and unstability of red phosphorus, improve its compatibility with high molecular material, there is good fire retardation when the fire retardant is applied in ABS resin, and lignin used is reproducible biological material, it is cheap and easy to get.
Description
Technical field
The invention belongs to polymeric material fields, and in particular to a kind of preparation method of organic coating red phosphorus combustion inhibitor and its
Application in ABS resin.
Background technique
As one of four large-engineering plastics, ABS(acrylonitrile-butadiene-styrene terpolymer) with good tough
The advantages that property, impact resistance, easy processing, it is widely used in every field.In recent years, electronics and the hair at full speed of automobile industry
Exhibition, it is growing to the demand of ABS resin.However, ABS resin easily burns, its limit oxygen index is only 18.4, horizontal
Burning velocity is very fast, and can generate a large amount of black smoke and toxic gas in burning, exists to human body or even environment serious
It threatens.Therefore, the flame retardant property for how improving ABS resin becomes the important topic of current ABS research.
Red phosphorus combustion inhibitor is a kind of halogen-free flame retardants, has excellent flame retardant effect, good thermal stability and is not easy to wave
Hair does not generate the advantages that corrosive gas, electrical insulating property are good, insoluble, fusing point is high and low malicious, additive amount is few in application process.
But works as red phosphorus to be easy explosion in the presence of dust form, and the phosphatization for generating and having hypertoxic character can be reacted under high temperature environment
Hydrogen, these all increase the delivery of red phosphorus and storage difficulty, significantly limit the application of red phosphorus.Therefore, only by red
It can be just set to play bigger fire-retardant application value after the cladding of phosphorus surface.
In recent years, the research of microencapsulated powder oil fire retardant is increasingly valued both at home and abroad.Microencapsulated powder oil is will be every
A tiny red phosphorus particle is coated on by various methods in macromolecule resin or inorganic material, thus keeping red phosphorus combustion inhibitor excellent
While point, the problems such as overcoming red phosphorus easy to moisture absorption when as fire retardant, easy kindling, dust explosive, and itself and tree can be improved
The compatibility of rouge improves the mechanical property of flame-proofed polymer material.
Summary of the invention
The purpose of the present invention is to provide a kind of cyanurotriamide modified lignin Wrapped up Phosphorus Fire Retardant and preparation method thereof,
Obtained flame-retardant agent have the characteristics that good thermal stability, good weatherability, with polymer-polymer miscibility is good, flame retarding efficiency is high, in ABS resin
In have broad application prospects.
To achieve the above object, the present invention adopts the following technical scheme:
A kind of cyanurotriamide modified lignin Wrapped up Phosphorus Fire Retardant, preparation method include the following steps:
(1) preparation of cyanurotriamide modified lignin: cyanurotriamide modified lignin is prepared using Mannich reaction principle,
It is specifically that alkali soluble is made into certain density aqueous slkali in deionized water, then dissolves lignin in aqueous slkali, then
By solution pour into equipped with electric mixer, thermometer, reflux condensing tube three-necked flask in, in 200-400 rpm stirring condition
Lower oil bath heating is then slowly added into a certain amount of aldehyde to 80-100 DEG C, reacts 1-3h, is slow added into a certain amount of trimerization
Cyanamide continues insulated and stirred and reacts 1-3h；
(2) preparation of Wrapped up Phosphorus Fire Retardant: cyanurotriamide modified lignin Wrapped up Phosphorus Fire Retardant uses chemical coprecipitation
Prepared, be specifically that the cyanurotriamide modified lignin obtained by the step (1) pours into beaker, be added a certain amount of red phosphorus and
Dispersing agent, mechanical stirring make red phosphorus fully dispersed, are slow added into a certain amount of acid and are neutralized, then 80-100 DEG C,
It is stirred to react 0.5-2h under the conditions of 200-400 rpm, is filtered by vacuum after product is aged 12-24h, filtration product is dried in an oven
It is crushed after dry, sieving, obtains khaki powder product, the as described cyanurotriamide modified lignin Wrapped up Phosphorus Fire Retardant is close
Envelope saves.
OH in aqueous slkali described in step (1)-Concentration be 2-10wt%, alkali used be sodium hydroxide, potassium hydroxide, hydrogen
One or more of barium monoxide；The dosage of the lignin is 20-100 g/mol OH-, lignin used is enzymatic hydrolysis wood
One or more of quality, alkali lignin, organosolv lignin, lignosulfonates.The dosage of the aldehyde is 0.05-0.5
Mol/10g lignin, aldehyde used are one or more of formaldehyde, acetaldehyde, butyraldehyde.The dosage of the melamine is 6.3-
25.2 g/10g lignin.
The dosage of red phosphorus is 0.4-1.2 g/g lignin in step (2)；The dosage of dispersing agent is that 0.005-0.01 g/g is red
Phosphorus, the dispersing agent include one of neopelex, calgon, lauryl sodium sulfate, OP-10 or
It is a variety of.
Acid described in step (2) is one or more of hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid.
For the present invention using cyanurotriamide modified lignin as capsule material, red phosphorus prepares a kind of novel organic packet as core material
Red phosphorus combustion inhibitor is covered, can both efficiently use this renewable resource of lignin to improve the unstability and superficiality of red phosphorus
Matter can also give full play to good flame retardant synergistic effect between red phosphorus and cyanurotriamide modified lignin, be expected in ABS resin
Middle application simultaneously obtains good flame retardant effect.
Remarkable advantage of the invention is:
(1) present invention can be adjusted reaction by the ratio of control reaction raw materials, reaction temperature, reaction time, mixing speed and be produced
Yield, pattern, particle size and the flame retardant property of object, yield is up to 90% or more, about 6 ~ 12 μm of product average grain diameter.
(2) synthesized by the present invention cyanurotriamide modified lignin Wrapped up Phosphorus Fire Retardant thermal stability is good, flame retarding efficiency
Height, good weatherability, good with high molecular material compatibility, in ABS resin when additive amount 25wt%, flame retardant rating is up to UL94
V-0 grades, ABS resin it is fire-retardant in have broad application prospects.
Detailed description of the invention
Fig. 1 is the process flow chart that the present invention is implemented；
Fig. 2 is the SEM figure of red phosphorus used in embodiment 1 and prepared fire retardant, wherein (a) figure is red phosphorus, (b) figure is fire retardant；
Fig. 3 is the FTIR figure of fire retardant prepared by embodiment 1；
Fig. 4 is the SEM figure of layer of charcoal after the burning of batten prepared by Application Example 1；
Fig. 5 is the SEM figure of layer of charcoal after the burning of batten prepared by Application Example 2；
Fig. 6 is the SEM figure of layer of charcoal after the burning of batten prepared by Application Example 3.
Specific embodiment
In order to make content of the present invention easily facilitate understanding, With reference to embodiment to of the present invention
Technical solution is described further, but the present invention is not limited only to this.
Embodiment 1
Weighing 5.6g(0.1mol) potassium hydroxide is in beaker, and addition deionized water is made into the potassium hydroxide solution of 2wt%, then
10g organosolv lignin is added in gained potassium hydroxide solution, after heating stirring dissolution, is poured into equipped with electric mixer, temperature
Degree is counted, in the three-necked flask of reflux condensing tube, and 0.2mol formaldehyde is added to 80 DEG C in oil bath heating under 200 rpm stirring conditions,
React 3h, add 12.6g(0.1mol) melamine, continue insulated and stirred reaction 3h after, reaction product is poured into beaker,
6g red phosphorus and 0.03g neopelex is added, is sufficiently stirred after being completely dispersed red phosphorus, is slow added into hydrochloric acid neutralization
It is in neutrality to solution, is then stirred to react 2h under the conditions of 80 DEG C, 200 rpm, after reaction gained suspension ageing 12h, very
Empty pump filter, filtration product after drying for 24 hours, pulverize and sieve in 80 DEG C of baking ovens, obtain cyanurotriamide modified lignin encapsulated red phosphorus
The khaki powder product of fire retardant, is sealed.
Fig. 2 is the SEM figure of red phosphorus used in the present embodiment and prepared fire retardant, wherein (a) figure is red phosphorus, (b) figure is resistance
Fire agent.It can be clearly seen that red phosphorus is the smooth elongated irregular block in surface by the comparison of two figures, be wrapped by rear size and become
Greatly, and rough surface, it can be seen that apparent organic coating layer shows that red phosphorus is tightly wrapped up, average grain diameter about 6-12 μ
m。
Fig. 3 is the FTIR figure of fire retardant prepared by the present embodiment.As seen from the figure, prepared fire retardant is in 3150 cm-1It is attached
Closely there is wide and strong absorption peak, belongs to the N-H stretching vibration of melamine.In conjunction with Fig. 2, show red phosphorus surface quilt really
Cyanurotriamide modified lignin cladding.
Embodiment 2
Weighing 8g(0.2mol) for sodium hydroxide in beaker, addition deionized water is made into the sodium hydroxide solution of 4wt%, then will
10g enzymolysis xylogen is added in gained sodium hydroxide solution, after heating stirring dissolution, is poured into equipped with electric mixer, temperature
It counts, in the three-necked flask of reflux condensing tube, 0.3mol formaldehyde is added to 90 DEG C in oil bath heating under 400 rpm stirring conditions,
React 2h, add 12.6g(0.1mol) melamine, continue insulated and stirred reaction 2h after, reaction product is poured into beaker,
8g red phosphorus and 0.04g neopelex is added, is sufficiently stirred after being completely dispersed red phosphorus, is slow added into sulfuric acid neutralization
It is in neutrality to solution, is then stirred to react 1h under the conditions of 90 DEG C, 400 rpm, after reaction gained suspension ageing 18h, very
Empty pump filter, filtration product after dry 18h, pulverize and sieve in 90 DEG C of baking ovens, obtain cyanurotriamide modified lignin encapsulated red phosphorus
The khaki powder product of fire retardant, is sealed.
Embodiment 3
Weighing 12g(0.3mol) for sodium hydroxide in beaker, addition deionized water is made into the sodium hydroxide solution of 6wt%, then will
20g enzymolysis xylogen is added in gained sodium hydroxide solution, after heating stirring dissolution, is poured into equipped with electric mixer, temperature
It counts, in the three-necked flask of reflux condensing tube, 0.4mol butyraldehyde is added to 100 DEG C in oil bath heating under 300 rpm stirring conditions,
React 1h, add 25.2g(0.2mol) melamine, continue insulated and stirred reaction 1h after, reaction product is poured into beaker,
10g red phosphorus and 0.1g lauryl sodium sulfate is added, is sufficiently stirred after being completely dispersed red phosphorus, is slow added into hydrochloric acid and is neutralized to
Solution is in neutrality, and is then stirred to react 0.5h under the conditions of 100 DEG C, 300 rpm, after reaction gained suspension ageing for 24 hours, very
Empty pump filter, filtration product after dry 12h, pulverize and sieve in 100 DEG C of baking ovens, obtain cyanurotriamide modified lignin encapsulated red phosphorus
The khaki powder product of fire retardant, is sealed.
Application Example 1
It weighs 25 parts of fire retardant that embodiment 1 obtains, 75 parts of ABS resin, double-screw extruding pelletizing and is injected into after mixing
Type is made flame retardant property test bars (length × width x thickness=mm × 3.2 of 130 mm × 10 mm), vertical burn test grade
Up to UL94 V-0 grades, carbon yield is 19.7% after fire-retardant batten sufficiently carbonizes at 500 DEG C in Muffle furnace.Pellet is squeezed out 220
DEG C, the melt index under 5Kg load be that melt index of the pure ABS resin of 3.24g/10min(under 220 DEG C, 5Kg load is
2.06g/10min).
Application Example 2
It weighs 25 parts of fire retardant that embodiment 2 obtains, 75 parts of ABS resin, double-screw extruding pelletizing and is injected into after mixing
Type is made flame retardant property test bars (length × width x thickness=mm × 3.2 of 130 mm × 10 mm), vertical burn test grade
Up to UL94 V-0 grades, carbon yield is 20.9% after fire-retardant batten sufficiently carbonizes at 500 DEG C in Muffle furnace.Pellet is squeezed out 220
DEG C, the melt index under 5Kg load be 3.58g/10min.
Application Example 3
It weighs 25 parts of fire retardant that embodiment 3 obtains, 75 parts of ABS resin, double-screw extruding pelletizing and is injected into after mixing
Type is made flame retardant property test bars (length × width x thickness=mm × 3.2 of 130 mm × 10 mm), vertical burn test grade
Up to UL94 V-0 grades, carbon yield is 18.8% after fire-retardant batten sufficiently carbonizes at 500 DEG C in Muffle furnace.Pellet is squeezed out 220
DEG C, the melt index under 5Kg load be 3.15g/10min.
Comparative example
As a comparison with commercially available microencapsulated powder oil, 75 parts of ABS resin are weighed, 25 parts of commercially available microencapsulated powder oil fire retardant mixes
It closes uniformly rear double-screw extruding pelletizing and is injection moulded, flame retardant property test bars (length × width x thickness=130 mm × 10 is made
The mm of mm × 3.2), vertical burn test grade is UL94 V-1 grades, and fire-retardant batten sufficiently carbonizes at 500 DEG C in Muffle furnace
Carbon yield is 16.8% afterwards.Squeezing out melt index of the pellet under 220 DEG C, 5Kg load is 1.85g/10min.
Fig. 4-Fig. 6 is the SEM figure of layer of charcoal after the burning of batten prepared by Application Example 1-3 respectively.As seen from the figure, gained charcoal
Layer even compact shows that sample has good flame retardant property.
The foregoing is merely presently preferred embodiments of the present invention, all equivalent changes done according to scope of the present invention patent with
Modification, is all covered by the present invention.
Claims (8)
1. a kind of preparation method of cyanurotriamide modified lignin Wrapped up Phosphorus Fire Retardant, characterized by the following steps:
(1) preparation of cyanurotriamide modified lignin: under 200-400 rpm stirring condition, the aqueous slkali of lignin is heated
To 80-100 DEG C, it is then slowly added into a certain amount of aldehyde, 1-3h is reacted, a certain amount of melamine is slow added into, after continuation of insurance
Temperature is stirred to react 1-3h；
(2) a certain amount of red phosphorus the preparation of Wrapped up Phosphorus Fire Retardant: is added in the cyanurotriamide modified lignin obtained by step (1)
And dispersing agent, mechanical stirring make red phosphorus fully dispersed, are slow added into a certain amount of acid and are neutralized, then in 80-100
DEG C, be stirred to react 0.5-2h under the conditions of 200-400 rpm, will product be aged 12-24h after be filtered by vacuum, filtration product drying,
It crushes, be sieved to get the cyanurotriamide modified lignin Wrapped up Phosphorus Fire Retardant.
2. preparation method according to claim 1, it is characterised in that: OH in aqueous slkali described in step (1)-Concentration be
2-10wt%, alkali used are one or more of sodium hydroxide, potassium hydroxide, barium hydroxide；
The dosage of the lignin is 20-100 g/mol OH-, lignin used is enzymolysis xylogen, alkali lignin, You Jimu
One or more of quality, lignosulfonates.
3. preparation method according to claim 1, it is characterised in that: the dosage of aldehyde described in step (1) is 0.05-0.5
Mol/10g lignin, aldehyde used are one or more of formaldehyde, acetaldehyde, butyraldehyde.
4. preparation method according to claim 1, it is characterised in that: the dosage of melamine described in step (1) is
6.3-25.2 g/10g lignin.
5. preparation method according to claim 1, it is characterised in that: the dosage of red phosphorus is 0.4-1.2 g/ in step (2)
G lignin；
The dosage of dispersing agent is 0.005-0.01 g/g red phosphorus, and the dispersing agent includes neopelex, hexa metaphosphoric acid
One or more of sodium, lauryl sodium sulfate, OP-10.
6. preparation method according to claim 1, it is characterised in that: acid described in step (2) be hydrochloric acid, sulfuric acid, nitric acid,
One or more of phosphoric acid.
7. a kind of as cyanurotriamide modified lignin encapsulated red phosphorus made from claim 1-6 any one preparation method is fire-retardant
Agent.
8. a kind of application of the cyanurotriamide modified lignin Wrapped up Phosphorus Fire Retardant in ABS resin as claimed in claim 7.
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| CN201810899984.XA CN109054097A (en) | 2018-08-09 | 2018-08-09 | A kind of cyanurotriamide modified lignin Wrapped up Phosphorus Fire Retardant and its application in ABS resin |
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Cited By (4)
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| CN110903491A (en) * | 2019-12-12 | 2020-03-24 | 湖南绿燊环保科技有限公司 | Flame retardant, modified polylactic acid and preparation method thereof |
| CN111548532A (en) * | 2020-06-19 | 2020-08-18 | 南京林业大学 | Biomass intumescent flame retardant, preparation method and special device thereof |
| CN114196075A (en) * | 2021-12-31 | 2022-03-18 | 福州大学 | Melamine hypophosphite modified lignin-coated aluminum hypophosphite flame retardant, preparation method thereof and application thereof in PA66 |
| CN114479192A (en) * | 2020-10-28 | 2022-05-13 | 中国石油化工股份有限公司 | Modified lignin-coated red phosphorus flame retardant and preparation method thereof |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110903491A (en) * | 2019-12-12 | 2020-03-24 | 湖南绿燊环保科技有限公司 | Flame retardant, modified polylactic acid and preparation method thereof |
| CN111548532A (en) * | 2020-06-19 | 2020-08-18 | 南京林业大学 | Biomass intumescent flame retardant, preparation method and special device thereof |
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| CN114196075A (en) * | 2021-12-31 | 2022-03-18 | 福州大学 | Melamine hypophosphite modified lignin-coated aluminum hypophosphite flame retardant, preparation method thereof and application thereof in PA66 |
| CN114196075B (en) * | 2021-12-31 | 2023-09-12 | 福州大学 | Melamine hypophosphite modified lignin coated aluminum hypophosphite flame retardant, preparation method thereof and application thereof in PA66 |
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Application publication date: 20181221 |