CN104039927A - Method for preparing melamine phosphate-based flame retardant - Google Patents
Method for preparing melamine phosphate-based flame retardant Download PDFInfo
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Abstract
The present invention relates to a method for preparing a melamine phosphate-based flame retardant, and more specifically, to a method for preparing a melamine phosphate-based flame retardant with excellent dispersion, electric insulation and water fastness by using a metal compound and cyanuric acid in a reaction of a melamine-based compound and a phosphorus-based compound.
Description
Technical field
The present invention relates to the preparation method of a kind of melamine phosphate (melamine phosphate) flame retardant, relate more specifically to, by utilize metallic compound and cyanuric acid in the reacting of trimeric cyanamide based compound and phosphorus series compound, prepare the method for the outstanding melamine phosphate flame retardant of dispersiveness, electrical insulating property, water tolerance.
Background technology
Fire retardant by physics or chemical process, improve there is the incendive character of appearance, as materials such as timber, fiber, paper, urethanes, thereby there is the material that suppresses burning or alleviate combustion efficacy.
Fire retardant is by hindering the specific combustion step such as heating, decomposition, protective membrane, heat-absorbing action, heat release to show its function.Because polymkeric substance is wanting in resistance to burning, thereby to for giving when the material production of flame retardant resistance is concerned about, centered by fire-retardant regulation specification Ye Yi developed country, be strictly applicable to electric appliance and electronic equipment, automobile, structure material, boats and ships flyer, electric wire field etc.
Fire retardant is in the past mainly that halogen is organic fire-retardant, bromine system or chlorine system form principal and subordinate, although these are outstanding aspect effect, but due to serious along with producing the problem that the stability to environment and human body that causes as the obnoxious flavour of dioxin (dioxin) etc. is relevant, thereby need to, for the improvement scheme of fire retardant in the past, also need to develop substitute materials simultaneously.
Therefore, carry out just energetically recently the research to non-halogen flame retardant, as this non-halogen flame retardant have that phosphorus system, inorganics are oxide based, inorganics hydroxide system, nitrogenous compound system, silicon system etc.
But phosphorus flame retardant has been developed the derivative of numerous species and has been used, although flame retardant resistance is outstanding, has many shortcomings aspect physical properties.And, there is the shortcoming of poor fire in the oxide based or inorganics hydroxide system of inorganics, nitrogenous compound system or silicon system are also difficult to give separately flame retardant resistance, also fail so far to realize the exploitation of the fire retardant of the performance that can reach halogen flame retardant, thereby are starved of the research to this.
Summary of the invention
Problem to be solved
The object of the invention is to, solve problem as above, meet the necessity of the novel fire retardant of exploitation, more specifically, provide by reacting at trimeric cyanamide based compound and phosphorus series compound, utilize metallic compound and cyanuric acid, prepare the method for the outstanding melamine phosphate flame retardant of dispersiveness, electrical insulating property, water tolerance.
The scheme of dealing with problems
The preparation method of melamine phosphate flame retardant of the present invention, make trimeric cyanamide based compound and phosphorus series compound react to prepare melamine phosphate flame retardant, it is characterized in that, comprise the following steps: the step of adding metallic compound and cyanuric acid in the operation of above-mentioned reaction; And after adding metallic compound and cyanuric acid, heat up and make the step of metallic compound and cyanuric acid condensation.
Beneficial effect
The melamine phosphate flame retardant of being prepared by preparation method of the present invention is outstanding aspect dispersiveness, electrical insulating property, water tolerance, and has the effect that can replace halogen flame in the past.
Embodiment
Some embodiment that describe in detail with reference to the following drawings, just can clear and definite advantages and features of the invention and the method that realizes these advantages and feature.But, the present invention is not limited to more following public embodiment, and can realize by mutually different variety of way, the present embodiment is only used to make of the present invention open more complete, and accurately informing that to general technical staff of the technical field of the invention the category of invention provides, the present invention only defines according to the scope of claims.In specification sheets full text, identical Reference numeral represents identical structure unit.
Below, preparation method of the present invention is described in detail.
The preparation method of melamine phosphate flame retardant of the present invention, is characterized in that, when trimeric cyanamide based compound and phosphorus series compound are reacted, comprises the following steps: the step of adding metallic compound and cyanuric acid in the operation of above-mentioned reaction; And after adding metallic compound and cyanuric acid, heat up and make the step of metallic compound and cyanuric acid condensation
At this, above-mentioned trimeric cyanamide based compound is preferably and is selected from trimeric cyanamide, melam, melem, mellon, alkalescence (Alkaline), melon, urea groups trimeric cyanamide, methylene radical two trimeric cyanamides (Methylenedimelamine), ethylene trimeric cyanamide (ethylenedimelamine), trimethylene two trimeric cyanamides (Trimethylene dimelamine), tetramethylene two trimeric cyanamides (Tetramethylene dimelamine), hexa-methylene two trimeric cyanamides (Hexamethylene dimelamine), decamethylene two trimeric cyanamides (Decamethylene dimelamine), ten dimethylene two trimeric cyanamides (Dodecamethylene dimelamine), to benzene two trimeric cyanamides (p-phenylene dimelamine), 1,3-cyclohexyl, two trimeric cyanamides (1,3-cyclohexylene dimelamine), p-Xylol two trimeric cyanamides (p-xylene dimelamine), diethylidene three trimeric cyanamides (diethylene trimelamine), triethylene four trimeric cyanamides (triethylene tetramelamine), four ethylidene five trimeric cyanamides (tetraethylene pentamelamine), six ethylidene seven trimeric cyanamides (hexaethylene heptamelamine), melamine cyanurate (Melamine cyanurate), more than one substituting group is by methyl, phenyl, carboxymethyl, 2-propyloic, cyanogen methyl, more than one in the melamine cyanurate that 2-cyanoethyl replaces.
At this, above-mentioned phosphorus series compound is preferably and is selected from phosphoric acid, ortho-phosphoric acid, tetra-sodium, triphosphoric acid, metaphosphoric acid, phosphorous acid, hydrogen phosphoric acid (hydro phosphorus Acid), phosphenic acid, phosphenous acid, phosphine oxide, phosphorus trihalide, phosphoryl halogen, phosphorus oxide, monometallic phosphoric acid hydrogen (mono metal hydrogen phosphate), primary ammonium phosphate (ammonia dihydrogen phosphate), bromic acid phosphoric acid salt (bromate phosphate), basic metal dihydrogen phosphate (alkali metal dihydrogen phosphate), halophosphate (halogenated phosphate), organo phosphorous compounds, alkylphosphines, alkyl phosphonium chloride (alkyl chlorophosphine), alkyl phosphite (alkyl phosphite), organic acid phosphoric acid salt, Acidic phosphates hydrogen ester (dialkyl hydrogen phosphate), aryl phosphoric acids hydrogen ester (aryl hydrogen phosphate), organic bisphosphate hydrogen ester (hydro organic diphosphonate ester), aryl phosphate, phosphate dialkyl ester, trialkylphosphate, more than one in halophosphines acid esters (halogenated phosphonate ester).
The above-mentioned metallic compound that is used in the reaction of trimeric cyanamide based compound-phosphorus series compound of the present invention is preferably and is selected from aluminum oxide, aluminium hydroxide, aluminium carbonate, magnesium oxide, magnesium hydroxide, magnesiumcarbonate, calcium oxide, calcium hydroxide, calcium carbonate, zinc oxide, zinc hydroxide, zinc carbonate, silicon oxide, silicon hydroxide, carbonic acid silicon, silicon-dioxide (silica), alkalimetal silicate, metal silicate, ANTIMONY TRIOXIDE SB 203 99.8 PCT, antimony pentaoxide, barium oxide, hydrated barta, barium carbonate, zinc borate compound (zinc borate), zinc borate (zinc boric acid), molybdenum oxide, molybdenum hydroxide, zeolite, hydrotalcite, talcum, graphite, graphite compound, more than one in titanium oxide.
Now, with respect to the trimeric cyanamide based compound of 100 weight parts, preferably add the above-mentioned metallic compound of 0.1 weight part～10 weight part.When the addition of metallic compound is less than 0.1 weight part, the electrical insulating property existing problems of the fire retardant of synthesized, when being greater than 10 weight part, although electrical insulating property improves, but the problem reducing due to the phosphorus content of the compound of synthesized, thereby can cause that flame retardant resistance reduces.
And, be used in preparation method's of the present invention above-mentioned cyanuric acid, with respect to the trimeric cyanamide based compound of 100 weight parts, preferably add 0.1 weight part～10 weight part.When the addition of cyanuric acid is less than 0.1 weight part, can not show the effect of improving of the water tolerance of fire retardant of synthesized and electrical insulating property, when being greater than 10 weight part, there is a large amount of untoward reactions that generate melamine cyanurates such problem that is activated.
For the present invention, in the reaction process of above-mentioned trimeric cyanamide based compound and phosphorus series compound, add metallic compound and cyanuric acid and heat up afterwards, first, be warming up to once 150 ℃, thereby moisture or solvent are carried out to complete drying.After this, be gradually heated to 150 ℃～450 ℃, and according to decomposition temperature characteristic separately, make the abundant condensation of metallic compound and cyanuric acid 30 minutes～10 hours, and finish reaction.
At this, by decompression, remove deammoniation or other materials producing, after finishing reaction, utilize various pulverizers to pulverize and for high molecular fire retardant.
Now, the size of particle is more fine better, but has the distribution between 0.2 μ m～50 μ m, and average particle size is preferably below 20 μ m.
On the other hand, the present invention comprises melamine phosphate flame retardant, and the melamine phosphate flame retardant of this melamine phosphate flame retardant for preparing by method as above comprises metallic compound and cyanurate in structure.
The fire retardant of being prepared by the present invention can together be used according to various uses and other organic phosphorus flame retardants, and the above-mentioned phosphorus flame retardant that can together use has triphenylphosphate, trialkyl phenyl phosphate ester (trialkyl phenyl phosphate), Tritolyl Phosphate, propylated triphenylphosphate (propylated triphenyl phosphate), butylated triphenyl phosphates (butylated triphenyl phosphate), triethyl phosphate, tributyl phosphate, resorcinol diphosphate (resorcinol diphosphate), bis-phenol bisphosphate (bisphenol diphosphate), methyl-phosphoric acid dimethyl ester (dimethylmethyl phosphonate), poly phosphate (polyphosphate ester), oligomeric organophosphate (oligomeric organo phosphate), pyrocatechol etherophosphoric acid (ethyl pyrocatechol phosphate), two pyrocatechol bisphosphates (dipyrocatechol biphosphate), polyethylene phosphorus oxygen (polyethylene oxyphosphate), methyl neopentyl phosphate (methyl neopentyl phosphate), tetramethylolmethane diethyl phosphoric acid ester (pentaerythritol diethylphosphate), tetramethylolmethane diphenyl phosphoester (pentaerythritol diphenylphosphate), methyl neopentyl phosphate (methyl neo pentylphosphonate), dicyclo neo-pentyl bisphosphate (dicyclo neo pentyl diphosphate), di neo-pentyl bisphosphate (dineo pentyl biphosphate) etc.
The polymer that can be suitable for melamine phosphate flame retardant of the present invention is polyvinyl chloride, polyester, benzene phenol resin, amine is resin, polyvinyl resin homopolymer and segmented copolymer or its multipolymer, acrylic resin homopolymer and segmented copolymer or its multipolymer, polyphenylene oxide (polyphenylene ether), polyphenylene oxide (polyphenylene oxide), urethane resin, heterocycle vinyl compound (hetero cycle vinyl compound), polyethylene terephthalate, acrylonitrile resin, vinyl-acetic ester, styrol copolymer, polycarbonate, polystyrene, acrylonitrile butadient styrene, styrene acrylonitrile copolymer, polyethers, high-impact polystyrene (highimpact polystyrene), polyhutadiene, aromatic ethenyl compound, polysulfones, polyoxymethylene, vinyl-acetic ester styrol copolymer, polyimide, nylon resin, phenoplast, aminoplastics (aminoplast), furans, polymeric amide, tetrafluoroethylene, methacrylonitrile resin, silicon is resin, ring-type unsaturated polyester, carbamate silicate (urethane silicate), cellulose ester, chlorinated rubber, ether of cellulose, cyanoethyl cellulose, rhodia etc.And, can also be for papermaking, rubber, timber, coating etc. except polymer.
Below, by the preferred embodiments of the present invention, come that the present invention will be described.
Embodiment 1
By the trimeric cyanamide of 126.12g (aldrich (Aldrich), molecular weight is 126.12, fusing point is 354 ℃), the magnesium oxide of 6.30g is, the cyanuric acid (aldrich of 6.30g, molecular weight is 129.08, and fusing point is 360 ℃) put into stainless steel reactor (3L) and stir and to mix for 10 minutes～20 minutes.After this, the phosphoric acid (assay75%) that gradually adds the aqueous solution state of 130.6g reacts, and opens stainless steel reactor, so that can fully evaporate by putting thermogenetic moisture.If thermopositive reaction completes to a certain degree, temperature is increased to 150 ℃ gradually, moisture is evaporated completely.With pulverulence, proceed to stir, temperature is continued to be promoted to simultaneously 300 ℃～450 ℃ react 1 hour above after, temperature is down to normal temperature gradually, pulverize and obtain the fire retardant of embodiment 1.
Embodiment 2
Use the trimeric cyanamide of 126.12g, the cyanuric acid of the aluminium hydroxide of 6.3g, 6.3g, the phosphoric acid of the aqueous solution state of 130.6g, obtains the fire retardant of embodiment 2 with the method identical with EXAMPLE l.
Embodiment 3
Use the trimeric cyanamide of 126.12g, the cyanuric acid of the hydrotalcite of 6.3g, 6.3g, the phosphoric acid of the aqueous solution state of 130.6g, obtains the fire retardant of embodiment 3 with the method identical with embodiment 1.
Embodiment 4
Use the trimeric cyanamide of 126.12g, the cyanuric acid of the silicon carbide of 6.3g, 6.3g, the phosphoric acid of the aqueous solution state of 130.6g, obtains the fire retardant of embodiment 4 with the method identical with embodiment 1.
Embodiment 5
Use the trimeric cyanamide of 126.12g, the cyanuric acid of the zinc borate compound of 6.3g, 6.3g, the phosphoric acid of the aqueous solution state of 130.6g, obtains the fire retardant of embodiment 5 with the method identical with embodiment 1.
Comparative example 1
Except not adding magnesium oxide, with the method identical with embodiment 1, obtain the fire retardant of comparative example 1.
Comparative example 2
Except not adding cyanuric acid, with the method identical with embodiment 1, obtain the fire retardant of comparative example 2.
Comparative example 3
Except not adding magnesium oxide, cyanuric acid, with the method identical with embodiment 1, obtain the fire retardant of comparative example 3.
Comparative example 4
Except not adding hydrotalcite, with the method identical with embodiment 3, obtain the fire retardant of comparative example 4.
Comparative example 5
Except not adding cyanuric acid, with the method identical with embodiment 3, obtain the fire retardant of comparative example 5.
Comparative example 6
Except not adding hydrotalcite, cyanuric acid, with the method identical with embodiment 3, obtain the fire retardant of comparative example 6.
Flame retardant resistance is evaluated
1. evaluation method
At polypropylene (Korea S Hunan petroleum chemistry company product; homopolymer, a secondary antioxidant songnox1010:500ppm; secondary antioxidant songnox168:1000ppm) in; mediate the embodiment of (kneading) above-mentioned preparation and the fire retardant of comparative example at 200 ℃ after, carry out having prepared flame retardant resistance working sample after granulation (pelleting).
2. mensuration project
(1) water tolerance: the powdered sample of the 10g of metering embodiment and comparative example and put into the beaker of 500ml after, stir 1 hour after dropping into the distilled water of normal temperature of 300ml.After stirring, the slurry disperseing is carried out to the weight that strainer is dried to measure minimizing, thereby measure the weight percent reducing.
(2) flame retardant resistance: UL-94 (registration of An Derui laboratory, Underlighter Laboratories Incorporation)
(3) oxygen index (Oxygen index): ASTM D2863
3. result
Table 1
| ? | Water tolerance (%) | Homo-polypropylene | Piperazine phosphate | Addition | Oxygen index | UL-94 |
| Embodiment 1 | 0.07 | 70 | 15 | 15 | 38.8 | V-O |
| Embodiment 2 | 0.06 | 70 | 15 | 15 | 38.5 | V-O |
| Embodiment 3 | 0.08 | 70 | 15 | 15 | 39.7 | V-O |
| Embodiment 4 | 0.56 | 70 | 15 | 15 | 37.1 | V-O |
| Embodiment 5 | 0.75 | 70 | 15 | 15 | 36.6 | V-O |
| Embodiment 6 | 0.66 | 70 | 15 | 15 | 38.4 | V-O |
| Comparative example 1 | 1.55 | 70 | 15 | 15 | 32.6 | V-O |
| Comparative example 2 | 1.57 | 70 | 15 | 15 | 33.3 | V-O |
| Comparative example 3 | 1.69 | 70 | 15 | 15 | 32.9 | V-O |
| Comparative example 4 | 1.99 | 70 | 15 | 15 | 33.8 | V-O |
| Comparative example 5 | 1.37 | 70 | 15 | 15 | 37.1 | V-O |
| Comparative example 6 | 1.19 | 70 | 15 | 15 | 36.7 | V-O |
From the result of above-mentioned table 1, can understand, with regard to the melamine phosphate flame retardant of being prepared by preparation method of the present invention, flame retardant resistance is outstanding, and especially water tolerance is outstanding, and improve the part of the shortcoming that can think phosphorus flame retardant, thereby also can in electric appliance and electronic field, use.
Above, centered by embodiments of the invention, be illustrated, but this is only exemplary, general technical staff of the technical field of the invention, should be appreciated that and can carry out other implementation columns that various distortion and enforcement are equal to according to above-described embodiment.Thus, should judge the real claimed technical scope of the present invention according to appending claims.
Claims (8)
1. a preparation method for melamine phosphate flame retardant, this preparation method makes trimeric cyanamide based compound react to prepare melamine phosphate flame retardant with phosphorus series compound, it is characterized in that, comprises the following steps:
In the operation of above-mentioned reaction, add the step of metallic compound and cyanuric acid; And
After adding metallic compound and cyanuric acid, heat up and make the step of their condensations.
2. the preparation method of melamine phosphate flame retardant according to claim 1, is characterized in that,
Above-mentioned trimeric cyanamide based compound is for being selected from trimeric cyanamide, melam, melem, mellon, alkalescence, melon, urea groups trimeric cyanamide, methylene radical two trimeric cyanamides, ethylene trimeric cyanamide, trimethylene two trimeric cyanamides, tetramethylene two trimeric cyanamides, hexa-methylene two trimeric cyanamides, decamethylene two trimeric cyanamides, ten dimethylene two trimeric cyanamides, to benzene two trimeric cyanamides, 1, 3-cyclohexyl two trimeric cyanamides, p-Xylol two trimeric cyanamides, diethylidene three trimeric cyanamides, triethylene four trimeric cyanamides, four ethylidene five trimeric cyanamides, six ethylidene seven trimeric cyanamides, melamine cyanurate, more than one substituting group is by methyl, phenyl, carboxymethyl, 2-propyloic, cyanogen methyl, more than one in the melamine cyanurate that 2-cyanoethyl replaces.
3. the preparation method of melamine phosphate flame retardant according to claim 1, is characterized in that,
Above-mentioned phosphorus series compound is for being selected from phosphoric acid, ortho-phosphoric acid, tetra-sodium, triphosphoric acid, metaphosphoric acid, phosphorous acid, hydrogen phosphoric acid, phosphenic acid, phosphinous acid, phosphorus oxide, phosphorus trihalide, phosphoryl halogen, phosphorus oxide, monometallic phosphoric acid hydrogen, primary ammonium phosphate, bromic acid phosphoric acid salt, basic metal dihydrogen phosphate, halophosphate, organo phosphorous compounds, alkylphosphines, alkyl phosphonium chloride, alkyl phosphite, organic acid phosphoric acid salt, Acidic phosphates hydrogen ester, aryl phosphoric acids hydrogen ester, organic bisphosphate hydrogen ester, aryl phosphate, phosphate dialkyl ester, trialkylphosphate, more than one in halophosphines acid esters.
4. the preparation method of melamine phosphate flame retardant according to claim 1, it is characterized in that, above-mentioned metallic compound is for being selected from aluminum oxide, aluminium hydroxide, aluminium carbonate, magnesium oxide, magnesium hydroxide, magnesiumcarbonate, calcium oxide, calcium hydroxide, calcium carbonate, zinc oxide, zinc hydroxide, zinc carbonate, silicon oxide, silicon hydroxide, carbonic acid silicon, silicon-dioxide, alkalimetal silicate, metal silicate, ANTIMONY TRIOXIDE SB 203 99.8 PCT, antimony pentaoxide, barium oxide, hydrated barta, barium carbonate, zinc borate compound, zinc borate, molybdenum oxide, molybdenum hydroxide, zeolite, hydrotalcite, talcum, graphite, graphite compound, more than one in titanium oxide.
5. the preparation method of melamine phosphate flame retardant according to claim 1, is characterized in that,
With respect to the trimeric cyanamide based compound of 100 weight parts, add the above-mentioned metallic compound of 0.1 weight part～10 weight part.
6. the preparation method of melamine phosphate flame retardant according to claim 1, is characterized in that,
With respect to the trimeric cyanamide based compound of 100 weight parts, add the above-mentioned cyanuric acid of 0.1 weight part～10 weight part.
7. the preparation method of melamine phosphate flame retardant according to claim 1, is characterized in that,
Above-mentioned intensification temperature is 150 ℃～450 ℃, and the condensation time is 30 minutes～10 hours.
8. a melamine phosphate flame retardant, it is prepared by the method described in any one in claim 1 to 7, comprises metallic compound and cyanurate in structure.
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| KR1020120069239A KR101424596B1 (en) | 2012-06-27 | 2012-06-27 | Preparation method of flame retardant using melaminephosphate |
| KR10-2012-0069239 | 2012-06-27 | ||
| PCT/KR2013/000570 WO2014003279A1 (en) | 2012-06-27 | 2013-01-24 | Method for preparing melamine phosphate-based flame retardant |
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| KR20030091136A (en) * | 2002-05-24 | 2003-12-03 | 주식회사 두본 | Non-halogen fire retardant material and method thereof |
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| CN104965872B (en) * | 2015-06-11 | 2019-04-26 | 联想(北京)有限公司 | A kind of information processing method and electronic equipment |
| CN106113194A (en) * | 2016-06-28 | 2016-11-16 | 郭迎庆 | A kind of preparation method of antiseptic fire-retardation bamboo slab rubber |
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| CN107177361A (en) * | 2017-06-02 | 2017-09-19 | 冯新平 | A kind of environment-friendlyflame flame retardant and its preparation technology |
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| CN115785526A (en) * | 2022-12-28 | 2023-03-14 | 浙江佳华精化股份有限公司 | Low-precipitation efficient phosphorus-nitrogen intumescent flame retardant and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104039927B (en) | 2016-09-14 |
| KR101424596B1 (en) | 2014-07-31 |
| WO2014003279A1 (en) | 2014-01-03 |
| KR20140006202A (en) | 2014-01-16 |
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