CN102977575A - Sulfonate fire retardation agents and preparation methods thereof - Google Patents
Sulfonate fire retardation agents and preparation methods thereof Download PDFInfo
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- CN102977575A CN102977575A CN2012103795603A CN201210379560A CN102977575A CN 102977575 A CN102977575 A CN 102977575A CN 2012103795603 A CN2012103795603 A CN 2012103795603A CN 201210379560 A CN201210379560 A CN 201210379560A CN 102977575 A CN102977575 A CN 102977575A
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Abstract
The present invention discloses a class of sulfonate fire retardation agents and preparation methods thereof, and relates to the technical field of synthesis of a class of sulfonate-containing fire retardation agents. A purposes of the present invention is to solve defects in the prior art, and provide a class of sulfonate fire retardation agents and preparation methods thereof. The sulfonate fire retardation agents have characteristics of no toxicity, droplet resistance, smoke suppression, high fire retardation efficiency, good thermal stability, low cost and simple process route, do not affect use performances, color and the like of products after being added to materials, and further form synergetic fire retardation effects with nitrogen. The sulfonate-containing fire retardation agents have the following structural formula, wherein R can be sulfonic group-containing fatty amine, an alcohol, sulfonic group-containing aromatic amine or phenol, and other substances. In addition, according to the present invention, the sulfonate-containing fire retardation agents can be prepared through a one step nucleophilic substitution reaction so as to simplify the process and avoid occurrence of multiple step post-treatments.
Description
Technical field
The present invention relates to the synthesis technical field that a class contains the sulfonate fire retardant.Contain triazine ring structure in the fire retardant that contains sulfonate of the present invention.The invention still further relates to the preparation method that such contains the sulfonate fire retardant.
Background technology
Fire retardant is to add in the more various materials, to improve the material fire protection flame retarding as a class chemosynthesis material of purpose.Reported at present with commercial fire retardant and be applied in the middle of the various materials, although all obtained flame-retarded efficiency in various degree, but permitted many-sided defective with existing in process, for example halogenated flame retardant the time can produce a large amount of cigarettes and corrosive gases in burning, and is indivedual even can produce the carcinogenic substance dioxin; The P-N flame retardant addition is large, causes the mechanical property of material and mechanical property to descend and perishable mould; The advantages such as cigarette environment-friendly high-efficiency although organic silicon fibre retardant has nontoxic, the present ubiquitous problem of this based flame retardant is expensive, and technology is ripe not enough, and the stability of product awaits further to improve.
Contain the sulfonate fire retardant and have efficient, nontoxic, anti-molten drop, press down the characteristics such as cigarette and be applied in the various materials, it can not only Effective Raise materials processing, resistance toheat, improves the mechanical mechanics property of material and flame retarding efficiency is high, few, the anti-molten drop drippage of addition.The business-like several sulfonate fire retardants that are reported in media at present are (such as 2; 4; 5 trichlorobenzene sodium sulfonates, perfluoro butyl potassium sulfonate, potassium phenylsulphonyl benzene sulfonate); its flame retardant effect is very good; as in polycarbonate (PC), add massfraction be 0.1% perfluoro butyl potassium sulfonate can make material LOI value by 37% of 24% raising, flame retardant properties reaches the V-0 level (3.2mm) of UL-94 and does not change the transparency and the mechanical property of PC.The problems such as that but above-mentioned several sulfonate fire retardant ubiquity is expensive, synthesis route and aftertreatment complexity.
Summary of the invention
Purpose of the present invention is exactly in order to solve above-mentioned weak point of the prior art, provides a class to contain sulfonate fire retardant and preparation method thereof.This based flame retardant is nontoxic, anti-molten drop, press down cigarette, and flame retarding efficiency is high, Heat stability is good and with low cost, operational path is simple, adds the use properties that do not affect goods in the material, color and luster etc. to, can also form with nitrogen the effect of cooperative flame retardant simultaneously.
Purpose of the present invention realizes by subordinate's technical scheme:
The structural formula that a described class contains the sulfonate fire retardant is as follows:
In, R can be for containing sulfonic aliphatic amide, alcohol and containing the materials such as sulfonic aromatic amine or phenol.
Preferred R is taurine potassium;
Preferred R is Sulphanilic Acid potassium;
Preferred R is 2,5-disulfonic acid base Phenylsulfonic acid potassium;
A kind of preparation method who contains the sulfonate fire retardant of the present invention comprises the steps:
The cyanuric chloride solubilizing agent is dissolved, add again and contain sulfonic organic amine, alcohol or phenol, be warming up to gradually 80-100 ℃, use the pH value of KOH aqueous solution conditioned reaction system in the reaction process, make it maintain 7-14, reaction is down to room temperature after finishing, and adds anti-phase precipitation agent in system, produce a large amount of white precipitate materials, suction filtration with the filter cake freeze-day with constant temperature, namely obtains the described sulfonate fire retardant that contains;
The mol ratio of the materials such as described cyanuric chloride and organic amine, alcohol, phenol is 1: 3.0～3.6;
The solvent load of every mole of cyanuric chloride is 500～2000ml;
The consumption of anti-phase precipitation agent is 5～10 times of the reaction final volume.
PH value by monitoring system in the reaction process is come the monitoring reaction process.
In order to realize better the present invention, described solvent comprises any one in water, acetone, dimethyl formamide, the dimethyl sulfoxide (DMSO);
Described anti-phase precipitation agent comprises any one in ethanol, acetonitrile, ethyl acetate, the tetrahydrofuran (THF).
Reaction process of the present invention is:
The present invention compared with prior art has following advantage and beneficial effect:
A class of the present invention contains the sulfonate fire retardant can be finished by a step nucleophilic substitution reaction, has saved unnecessary pilot process, has both simplified technique, has avoided again the appearance of multistep aftertreatment situation; The raw material sources of such sulfonate fire retardant are abundant simultaneously, and are cheap and easy to get.
Of the present inventionly contain the sulfonate fire retardant structurally, contain simultaneously sulfonic group and nitrogen in the molecule, the two can play the effect of cooperative flame retardant;
Description of drawings:
The ESI (negative) of Fig. 1 fire retardant (I)-MS spectrogram
The infrared spectrum of Fig. 2 fire retardant (I)
The hydrogen nuclear magnetic resonance spectrogram of Fig. 3 fire retardant (I)
The hot weightless picture of Fig. 4 fire retardant (I)
The ESI (negative) of Fig. 5 fire retardant (II)-MS
The infared spectrum of Fig. 6 fire retardant (II)
The nucleus magnetic hydrogen spectrum of Fig. 7 fire retardant (II)
The hot weightless picture of Fig. 8 fire retardant (II)
The ESI (negative) of Fig. 9 fire retardant (III)-MS spectrogram
The infrared spectrum of Figure 10 fire retardant (III)
The hydrogen nuclear magnetic resonance spectrogram of Figure 11 fire retardant (III)
The hot weightless picture of Figure 12 fire retardant (III)
Embodiment
Below in conjunction with embodiment the present invention is explained in detail, but embodiments of the present invention are not limited to this.
What preparation had a following structure contains the sulfonate fire retardant.
At first the cyanuric chloride stirring and dissolving in four-hole bottle with 9.225g (0.05mol) adds the aqueous solution that contains the 18.75g taurine again in the acetone of 50ml, along with the carrying out that reacts is elevated to 90 ℃ with the temperature of system slowly.With the pH value of pH meter monitoring system, and with the pH value of KOH aqueous solution regulation system, it is remained on about 9 in the reaction process.
When the pH of system value no longer changes, indicate that reaction finishes.Cooling, concentrating under reduced pressure adds the dehydrated alcohol of 6 times of volumes, has a large amount of white solids to separate out in the process, suction filtration use methyl alcohol: the mixing solutions washing leaching cake of chloroform=3: 2 (v/v), and with triketohydrindene hydrate detection filtrate until taurine be divided.Place 70 ℃ of freeze-day with constant temperature of vacuum drying oven to be a kind of sulfonate fire retardant that contains of the present invention white mass.Yield is 90.2%.The structural characterization data are as follows, and concrete spectrogram is seen Figure of description (Fig. 1～4):
FT-IR data (KBr, cm
-1): 3400 (vs N-H), 2856 (CH
2-), 1576 (C=N-), 1184and 1050 (SO
2-).
ESI-MS (negative) is spectral data (m/z): 524.93443 (M-K
+), 486.97991 (M-2K
++ H), 449.02273 (M-3K
++ 2H).
1H-NMR (500M, d
6-DMSO): 2.61ppm (unimodal), 3.447ppm (unimodal), 6.296～6.529ppm (triplet).
Flame retardant properties is used: get 0.3g and contain the sulfonate fire retardant and add in the 500g polycarbonate (bayer2805), make fire-retardant polycarbonate, extrude through twin screw extruder, after the granulation, be injection molded into standard batten (standard is GB/T17037.1-1997).Combustion test shows: in the time of 750 ℃, the charring rate of pure PC is 30.4%, and its charring rate 19.96% of the PC after the modification; The limiting oxygen index(LOI) of pure PC (LOI%) is that 24, UL-94 reaches the V-2 level, and its LOI of the PC after the modification is that 33.6, UL-94 reaches V-0.
At first the cyanuric chloride with 9.225g (0.05mol) places the four-hole bottle stirring and dissolving in the water of 50ml, adds the aqueous solution that contains the 18.75g taurine again, along with the carrying out that reacts is elevated to 90 ℃ with the temperature of system slowly.With the pH value of pH meter monitoring system, and with the pH value of KOH aqueous solution regulation system, it is remained on about 9 in the reaction process.
When the pH of system value no longer changes, indicate that reaction finishes.Cooling, concentrating under reduced pressure adds the dehydrated alcohol of 6 times of volumes, has a large amount of white solids to separate out in the process, suction filtration use methyl alcohol: the mixing solutions washing leaching cake of chloroform=3: 2 (v/v), and with triketohydrindene hydrate detection filtrate until taurine be divided.Place 70 ℃ of freeze-day with constant temperature of vacuum drying oven to be a kind of sulfonate fire retardant that contains of the present invention white mass.Yield is 93.8%.
Cyanuric chloride stirring and dissolving in four-hole bottle with 9.225g (0.05mol) adds the aqueous solution that contains the 18.75g taurine again in the water of 50ml first, along with the carrying out that reacts is elevated to 90 ℃ with the temperature of system slowly.With the pH value of pH meter monitoring system, and with the pH value of KOH aqueous solution regulation system, it is remained on about 9 in the reaction process.
When the pH of system value no longer changes, indicate that reaction finishes.Cooling, concentrating under reduced pressure transfers to 2 with concentrated hydrochloric acid with the pH of end reaction liquid, there are a large amount of white solids to separate out in the process, suction filtration, respectively water, methyl alcohol: the mixing solutions washing leaching cake of chloroform=3: 2 (v/v), and detect filtrate until taurine is divided with triketohydrindene hydrate.Place 70 ℃ of freeze-day with constant temperature of vacuum drying oven to be a kind of sulfonate fire retardant that contains of the present invention white mass.Yield is 95%.
Other use concentrated hydrochloric acid instead as precipitation agent with embodiment 1, productive rate 93.1%.
What preparation had a following structure contains the sulfonate fire retardant.
At first the cyanuric chloride stirring and dissolving in four-hole bottle with 9.225g (0.05mol) adds the aqueous solution that contains the 25.95g Sulphanilic Acid again in the water of 50ml, along with the carrying out that reacts is elevated to 90 ℃ with the temperature of system slowly.With the pH value of pH meter monitoring system, and with the pH value of KOH aqueous solution regulation system, it is remained on about 9 in the reaction process.
When the pH of system value no longer changes, indicate that reaction finishes.Cooling, concentrating under reduced pressure transfers to 2 with concentrated hydrochloric acid with the pH of end reaction liquid, there are a large amount of white solids to separate out in the process, suction filtration, respectively water, methyl alcohol: the mixing solutions washing leaching cake of chloroform=3: 2 (v/v), and detect filtrate until Sulphanilic Acid is divided with triketohydrindene hydrate.Place 70 ℃ of freeze-day with constant temperature of vacuum drying oven to be a kind of sulfonate fire retardant that contains of the present invention white mass.Yield is 95%.The structural characterization data are as follows, and concrete spectrogram is seen Figure of description (Fig. 5～8):
FT-IR data (KBr, cm
-1): 3400 (vsN-H), 1576 (C=N-), 1184and 1050 (SO
2-).
ESI-MS (negative) is spectral data (m/z): 668.932 (M-K
+), 630.978 (M-2K
++ H).
1H-NMR (500M, d
6-DMSO): 7.536ppm (unimodal, 6H), 7.759ppm (unimodal, 6H), 9.37～11.25ppm (the group peak, 3H).
Flame retardant properties is used: get 0.3g and contain the sulfonate fire retardant and add in the 500g polycarbonate (bayer2805), make fire-retardant polycarbonate, extrude through twin screw extruder, after the granulation, be injection molded into standard batten (standard is GB/T17037.1-1997).Combustion test shows: in the time of 750 ℃, the charring rate of pure PC is 30.4%, and its charring rate 38.96% of the PC after the modification; The limiting oxygen index(LOI) of pure PC (LOI%) is that 24, UL-94 reaches the V-2 level, and its LOI of the PC after the modification is that 34.3, UL-94 reaches V-0.
At first the cyanuric chloride stirring and dissolving in four-hole bottle with 9.225g (0.05mol) adds the aqueous solution that contains the 25.95g Sulphanilic Acid again in the acetone of 50ml, along with the carrying out that reacts is elevated to 90 ℃ with the temperature of system slowly.With the pH value of pH meter monitoring system, and with the pH value of KOH aqueous solution regulation system, it is remained on about 9 in the reaction process.
When the pH of system value no longer changes, indicate that reaction finishes.Cooling, concentrating under reduced pressure is done anti-phase precipitation agent with acetonitrile, there are a large amount of white solids to separate out in the process, suction filtration, respectively water, methyl alcohol: the mixing solutions washing leaching cake of chloroform=3: 2 (v/v), and detect filtrate until Sulphanilic Acid is divided with triketohydrindene hydrate.Place 70 ℃ of freeze-day with constant temperature of vacuum drying oven to be a kind of sulfonate fire retardant that contains of the present invention white mass.Yield is 95.3%.
Other are with embodiment 5, and using ethanol instead is anti-phase precipitation agent, and yield is 94.8%.
What preparation had a following structure contains the sulfonate fire retardant.
At first the cyanuric chloride stirring and dissolving in four-hole bottle with 9.225g (0.05mol) adds and contains 2 of 41.25g in the acetone of 50ml, and the aqueous solution of 5-disulfonic acid base Phenylsulfonic acid potassium is along with the carrying out that reacts is elevated to 90 ℃ with the temperature of system slowly.With the pH value of pH meter monitoring system, and with the pH value of KOH aqueous solution regulation system, it is remained on about 9 in the reaction process.
When the pH of system value no longer changes, indicate that reaction finishes.Cooling, concentrating under reduced pressure is done anti-phase precipitation agent with acetonitrile, there are a large amount of white solids to separate out in the process, suction filtration, respectively water, methyl alcohol: the mixing solutions washing leaching cake of chloroform=3: 2 (v/v), and detect filtrate until 2,5-disulfonic acid base Phenylsulfonic acid is divided with triketohydrindene hydrate.Place 70 ℃ of freeze-day with constant temperature of vacuum drying oven to be a kind of sulfonate fire retardant that contains of the present invention white mass.Yield is 95%.The structural characterization data are as follows, and concrete spectrogram is seen Figure of description (Fig. 5～8):
FT-IR data (KBr, cm
-1): 3400 (vs N-H), 1576 (C=N-), 1184and 1050 (SO
2-).
ESI-MS (negative) is spectral data (m/z): 990.88777 (M-Na
+), 952.92939 (M-Na
+-K
++ H), 914.979961 (M-Na
+-2K
++ 2H).
1H-NMR (500M, d
6-DMSO): 7.531～7.769ppm (the group peak, 9H), 9.375～9.538ppm (the group peak, 3H).
Flame retardant properties is used: get 0.3g and contain the sulfonate fire retardant and add in the 500g polycarbonate (bayer2805), make fire-retardant polycarbonate, extrude through twin screw extruder, after the granulation, be injection molded into standard batten (standard is GB/T17037.1-1997).Combustion test shows: in the time of 750 ℃, the charring rate of pure PC is 30.4%, and its charring rate 29.5% of the PC after the modification; The limiting oxygen index(LOI) of pure PC (LOI%) is that 24, UL-94 reaches the V-2 level, and its LOI of the PC after the modification is that 36.8, UL-94 reaches V-0.
At first the cyanuric chloride stirring and dissolving in four-hole bottle with 9.225g (0.05mol) adds and contains 2 of 41.25g in the water of 50ml, and the aqueous solution of 5-disulfonic acid base Phenylsulfonic acid potassium is along with the carrying out that reacts is elevated to 90 ℃ with the temperature of system slowly.With the pH value of pH meter monitoring system, and with the pH value of KOH aqueous solution regulation system, it is remained on about 9 in the reaction process.
When the pH of system value no longer changes, indicate that reaction finishes.Cooling, concentrating under reduced pressure is done anti-phase precipitation agent with ethanol, there are a large amount of white solids to separate out in the process, suction filtration, respectively water, methyl alcohol: the mixing solutions washing leaching cake of chloroform=3: 2 (v/v), and detect filtrate until 2,5-disulfonic acid base Phenylsulfonic acid is divided with triketohydrindene hydrate.Place 70 ℃ of freeze-day with constant temperature of vacuum drying oven to be a kind of sulfonate fire retardant that contains of the present invention white mass.Yield is 93.9%.
Other are with embodiment 8, and using acetone instead is solvent, and yield is 95.8%.
Other are with embodiment 8, and using concentrated hydrochloric acid instead is anti-phase precipitation agent, and yield is 93.4%.
As mentioned above, can realize preferably the present invention.
Claims (10)
1. a class sulfonate fire retardant, structural formula is as follows:
In, R can be for containing sulfonic aliphatic amide, alcohol and containing sulfonic aromatic amine or phenol.
2. a class hydrochlorate fire retardant according to claim 1 is characterized in that R is taurine potassium; R is Sulphanilic Acid potassium; R is 2,5-disulfonic acid base Phenylsulfonic acid potassium.
3. a class sulfonate fire retardant according to claim 1 is characterized in that sulfonate fire retardant structural formula is as follows:
4. a class sulfonate fire retardant according to claim 1 is characterized in that sulfonate fire retardant structural formula is as follows:
5. a class sulfonate fire retardant according to claim 1 is characterized in that sulfonate fire retardant structural formula is as follows:
6. a class contains the preparation method of sulfonate fire retardant, comprises the steps:
The cyanuric chloride solubilizing agent is dissolved, add again and contain sulfonic organic amine, alcohol or phenol, be warming up to gradually 80-100 ℃, use the pH value of KOH aqueous solution conditioned reaction system in the reaction process, make it maintain 7-14, reaction is down to room temperature after finishing, and adds anti-phase precipitation agent in system, produce a large amount of white precipitate materials, suction filtration with the filter cake freeze-day with constant temperature, namely obtains to contain the sulfonate fire retardant.
7. a described class contains the preparation method of sulfonate fire retardant according to claim 6, and the mol ratio that it is characterized in that described cyanuric chloride and organic amine, alcohol or phenol is 1: 3.0～3.6.
8. a described class contains the preparation method of sulfonate fire retardant according to claim 6, the solvent load that it is characterized in that described every mole of cyanuric chloride is 500～2000ml, and described solvent comprises any one in water, acetone, dimethyl formamide, the dimethyl sulfoxide (DMSO).
9. a described class contains the preparation method of sulfonate fire retardant according to claim 6, and the consumption that it is characterized in that described anti-phase precipitation agent is 5～10 times of the reaction final volume; Described anti-phase precipitation agent comprises any one in ethanol, acetonitrile, ethyl acetate, the tetrahydrofuran (THF).
10. a class contains the application of sulfonate fire retardant aspect fire-retardant.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103618109A (en) * | 2013-12-09 | 2014-03-05 | 山东海容电源材料有限公司 | Flame-retardant additive for electrolyte and flame-retardant lithium ion battery electrolyte |
| CN104262679A (en) * | 2014-10-08 | 2015-01-07 | 常熟三爱富中昊化工新材料有限公司 | Sulfonate fire retardant and preparation method thereof |
| CN109796629A (en) * | 2017-11-17 | 2019-05-24 | 南开大学 | Novel N-P-S expansion type phosphor flame retardant and preparation method thereof |
| CN115403607A (en) * | 2022-09-02 | 2022-11-29 | 铨盛聚碳科技股份有限公司 | Novel organosilicone sulfonate flame retardant and preparation method thereof |
| CN117736460A (en) * | 2024-02-07 | 2024-03-22 | 四川兴晶铧科技有限公司 | Melamine benzenesulfonate flame retardant, and preparation method and application thereof |
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| CN1966496A (en) * | 2005-11-14 | 2007-05-23 | 中国科学院福建物质结构研究所 | Symmetrical triazine compound |
| JP4434466B2 (en) * | 2000-10-25 | 2010-03-17 | 日産化学工業株式会社 | Thermal decomposition inhibitor for triazine ring-containing compounds |
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| JP4434466B2 (en) * | 2000-10-25 | 2010-03-17 | 日産化学工業株式会社 | Thermal decomposition inhibitor for triazine ring-containing compounds |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103618109A (en) * | 2013-12-09 | 2014-03-05 | 山东海容电源材料有限公司 | Flame-retardant additive for electrolyte and flame-retardant lithium ion battery electrolyte |
| CN103618109B (en) * | 2013-12-09 | 2016-08-24 | 山东海容电源材料有限公司 | Electrolyte flame-retardant additive and flame-retardant lithium ion battery electrolyte |
| CN104262679A (en) * | 2014-10-08 | 2015-01-07 | 常熟三爱富中昊化工新材料有限公司 | Sulfonate fire retardant and preparation method thereof |
| CN104262679B (en) * | 2014-10-08 | 2017-05-24 | 常熟三爱富中昊化工新材料有限公司 | Sulfonate fire retardant and preparation method thereof |
| CN109796629A (en) * | 2017-11-17 | 2019-05-24 | 南开大学 | Novel N-P-S expansion type phosphor flame retardant and preparation method thereof |
| CN115403607A (en) * | 2022-09-02 | 2022-11-29 | 铨盛聚碳科技股份有限公司 | Novel organosilicone sulfonate flame retardant and preparation method thereof |
| CN117736460A (en) * | 2024-02-07 | 2024-03-22 | 四川兴晶铧科技有限公司 | Melamine benzenesulfonate flame retardant, and preparation method and application thereof |
| CN117736460B (en) * | 2024-02-07 | 2024-04-30 | 四川兴晶铧科技有限公司 | Melamine benzenesulfonate flame retardant, and preparation method and application thereof |
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Application publication date: 20130320 |