CN101086136A - Flame-resistant agent and its preparing process and usage - Google Patents
Flame-resistant agent and its preparing process and usage Download PDFInfo
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- CN101086136A CN101086136A CN 200710058164 CN200710058164A CN101086136A CN 101086136 A CN101086136 A CN 101086136A CN 200710058164 CN200710058164 CN 200710058164 CN 200710058164 A CN200710058164 A CN 200710058164A CN 101086136 A CN101086136 A CN 101086136A
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Abstract
The invention involves a flame retardant, its molecular formula is C14H26O4P2S2N2, and it is named 1, 4-(0, 0-diethyl phosphorothioate phosphorus-imide) benzene. Its manufacturing method is: dissolving 0, 0-diethyl thio-phosphorus oxychloride and p-phenylene diamine which mole ratio are 2:1 into chloroform or acetonitrile, adding the accelerating agent 4-dimethylamino pyridine which mole amount is 0.1-0.5% of p-phenylene diamine and acid-bond agent triethylamine which mole amount is same with p-phenylene diamine, reacting 3-5 hours under the condition of 0-50 deg.C, then stopping the reaction, washing the product with water, then re-crystallining the product with acetone, drying 24 hours with air flow, then said flame retardant is produced. The flame retardant said in the invention is special for acrylic fiber production technology, the adding weight amount is 15-20% of polyacryl-nitrile component . The flame retardant in the invention does not contains halides, the flame-proof effect is good, the efficient is high and toxicity is low, it is a environment-friendly type flame retardant for acrylic fiber.
Description
Technical field
The present invention relates to a kind of fire retardant technology, be meant a kind of fire retardant and manufacture method and purposes that acrylic fibers contain highly effective flame-retardant composition phosphorus, sulphur and nitrogen monomer that be used for especially, international monopoly Main classification number plan is Int.Cl.C08L1/02 (2006.01).
Background technology
The premium properties that acrylic fiber has that proportion is little, bulkiness and warmth retention property etc. are similar to wool has the title of " artificial wool ", is one of important kind in the synthetic fiber.But it is inflammable that acrylic fiber exists major defect, and its limited oxygen index is 18 only, is the synthetic fiber that are easy to burn.Obviously, the textiles made from acrylic fibers is easy to ignition and initiation fire, cause casualties and the loss of property tremendous economic, and, can discharge the bigger gases of toxicity such as nitrile compound and ammonia during the acrylic fibers burning, jeopardize health of human body and contaminated environment.Therefore, the fire resistance of acrylic fiber is very important.Fire retardant of the present invention is exclusively used in acrylic fibers, can be described as the acrylic fibers fire retardant.
The Velicern that Italy Si Niya company developed in nineteen sixty-five is the mainstream product in the flame-retardant acrylic fibre.The anti-flammability of this fiber by acrylonitrile with halogen-containing monomers vinylidene chloride copolymerization and add the antimony pentoxide synergist and realize, its limited oxygen index (LOI) value can reach 26～29, suitable fabric has excellent flame-retardant performance (Wang Gang, Wei Likelun to be used for structure, FR and process technology thereof. the Guangdong chemical fibre, 1994,4:30～37); The Ka Naka synthetic fibre is a kind of acrylic fibers fire resistance fibre of Japanese Zhong Yuan company in the nineteen fifty-seven exploitation, its limited oxygen index is up to 27～28, also be output maximum, flame-retardant acrylic fibre fiber species (Hao Xinmin, Zhang Jianchun that specification is maximum in the world, the performance of polyacrylic and polyester fiber and application study, the Chinese Individual protective gear, 2001,4:12～15).After itself and conventional fibre blending, interweaving, can bring into play its superior fire resistance; Another kind of fire resistance fibre Loew synthetic fibre is that Japanese clock spins the fire resistance fibre of company in beginning suitability for industrialized production in 1977, the synthetic fiber that it adopts acrylonitrile to obtain with the vinylidene chloride copolymerization, have excellent flame-retardant performance, security and avirulence, and feel is good, drapability is good, and is high fluffy, easy dyeing, (justice waterborne wins, Wang Shuzhong for spinnability and excellent processability, flame-retardant acrylic fibre fiber " Loew synthetic fibre ". fabrics for industrial use, 1985,3:3～5).This fiber not only can purely be spun into various fabrics, can also make the fabric that reaches the regulation flame-retardant standard with various general fibre blending; Teklan is the acrylic fibers fire resistance fibre that Britain Courtaulds company went into operation in 1962, be mainly used in military Fake Furs, chemical protecting suit and military camouflage textile material, also can be used for (Wang Yanzhi, Zhang Wangxi such as the waterproof fabric of public place and upholstery, the flame-retardant acrylic fibre pre-test, chemical fibre and weaving, 1997, (4-5): 4～5,13).
The sixties in last century, the many units of China flame-retardant acrylic fibre production technology that also begins one's study, but the suitability for industrialized production that all is unrealized.The seventies, it is 27 flame-retardant acrylic fibre fiber (Wu Guoming, Mei Qianfang, Yang Zhili, the research of blending fire retardant acrylic fibers, Guangdong chemical fibre, 1989 (3): 1～14) that Shanghai Institute of Synthetic Fiber adopts flame-retardant system (Cl/Cl-Sb) to develop LOI; The eighties, South China Science ﹠ Engineering University is solvent with DMSO, adopts and directly add FR in spinning solution
8And Sb
2O
3The homogeneous phase blending method, the flame-retardant acrylic fibre fiber that spinned LOI 〉=26, can put out certainly (Zhu Qingsong, the domestic-developed present situation and the development trend of flame-retardant acrylic fibre, textile science research, 2002,4:1～3,23); The nineties, South China Science ﹠ Engineering University has reported that again with ammonium dihydrogen phosphate (ADP) and urea be composite flame-retardant agent, adopt NaSCN solvent route to carry out the method for homogeneous phase blend spinning flame-retardant acrylic fibre, LOI can reach 28 (Fang Jun, Wu Guoming, Mei Qianfang etc., the NaSCN solvent method spins the research that non-halogen is flame-retardant acrylic fibre, South China Science ﹠ Engineering University's journal (natural science edition), 1996,24 (7): 121～127), but regrettably these achievements in research are not seen so far and are applied to suitability for industrialized production.Entered since the new century fire retardant and the surface treated nanometer Sb of China Textile Academy to contain Br and N in the molecular structure simultaneously
2O
3Composite, adopt NaSCN solvent route, having developed LOI by the method for blend is 27.5, and the flame-retardant acrylic fibre that physical and mechanical properties is good, but also be at present the pilot scale stage (Zhu Qingsong. the domestic-developed present situation and the development trend of flame-retardant acrylic fibre. textile science research, 2002,4:1～3,23).Compared with developed countries, the flame-retardant acrylic fibre industry of China also is in the starting stage, and at present domestic have only the Fushun Acrylic Fibers Plant to produce the flame-retardant acrylic fibre fiber.
The performance and the quality of flame-retardant acrylic fibre fiber depend on fire retardant.In other words, good fire retardant is a key factor of making good flame-retardant acrylic fibre fiber.Existing flame-retardant acrylic fibre mostly obtains by halide-containing fire retardant and acrylonitrile compolymer.The halide-containing fire retardant has good flame-retardant effect for acrylic fibers.But, to put into practice verifiedly, halogen containing flame-retardant can produce toxic gas in the decomposes process, bring very serious environmental pollution problem, does not meet the requirement of green production.Therefore, exploitation low toxicity, Halogen, compliance with environmental protection requirements are the key points of the actual popularization of flame-retardant acrylic fibre fiber production application.The acrylic fibers fire retardant is a general orientation of present countries in the world research efficiently.
Summary of the invention
At the deficiency of existing acrylic fibers with fire retardant, the technical problem that quasi-solution of the present invention is determined is that a kind of fire retardant and manufacture method thereof and purposes are provided.Described fire retardant is exclusively used in acrylic fibers, and halide-containing does not have good flame retardation effect, and characteristics of high efficiency and low toxicity is a kind of environment-friendly type acrylic fibers fire retardant; Described fire retardant manufacture method, it is simple to have technology, with low cost, and the productive rate height is easy to characteristics such as suitability for industrialized production.Characteristics such as described fire retardant is exclusively used in the preparation production of flame-retardant acrylic fibre fiber, and it is strong to have adaptability, easy to use.
The technical scheme that the present invention solves described flame retardant products technical problem is: design a kind of fire retardant, its molecular formula is C
14H
26O
4P
2S
2N
2, chemical structural formula is:
Called after 1,4-(O, O-diethyl sulfo-phosphoryl imido grpup) benzene.
The technical scheme that the present invention solves described fire retardant manufacture method technical problem is: the manufacture method that designs a kind of fire retardant, it adopts following technology: the O that with mol ratio is 2: 1, O-diethyl sulfo-phosphoryl chloride and p-phenylenediamine (PPD) are dissolved in chloroform or the acetonitrile, add p-phenylenediamine (PPD) amount 0.1～0.5% catalyst 4-dimethylamino naphthyridine and with the equimolar acid binding agent triethylamine of p-phenylenediamine (PPD), under 0～50 ℃ of condition, reaction 3～5h, after stopping reaction, washing net income product, use acetone recrystallization again, behind the pneumatic conveying drying 24h, promptly can be made into described fire retardant: 1,4-(O, O-diethyl sulfo-phosphoryl imido grpup) benzene.
The technical scheme that the present invention solves described fire retardant purposes technical problem is: the purposes that designs a kind of fire retardant, it is characterized in that fire retardant of the present invention is exclusively used in the acrylic fiber production process technology, the addition of fire retardant is 15～20% of a polyacrylonitrile composition weight.
Compared with prior art, the flame-retardant composition of fire retardant of the present invention is: phosphorus, sulphur and nitrogen, and halide-containing during thermal decomposition, does not seldom produce toxic gas, and contaminated environment is little, does not also harm health of human body relatively; The manufacture method of fire retardant of the present invention is simple, is swift in response productive rate height, synthesis technique environmental protection; Fire retardant of the present invention is exclusively used in acrylic fiber production process, and Technological adaptability is strong, and is easy to use, particularly can realize green production.
The specific embodiment
Further narrate the present invention below in conjunction with embodiment:
Fire retardant of the present invention, molecular formula are C
14H
26O
4N
2P
2S
2, chemical structural formula is:
But called after: 1,4-(O, O-diethyl sulfo-phosphoryl imido grpup) benzene, perhaps N, N '-two (O, O-diethyl sulfo-phosphoryl imido grpup)-1,4-p-phenylenediamine (PPD).
In the chemical structural formula of fire retardant of the present invention, can be clear that, highly effective flame-retardant element phosphor, sulphur and three kinds of materials of nitrogen, and phosphorus and sulphur, phosphorus and nitrogen are to be present in the fire retardant with the form of stablizing chemical bond.Stable existence and synergy each other in the time of highly effective flame-retardant element phosphor, sulphur and three kinds of materials of nitrogen can improve the anti-flaming function and the flame retardant effect of fire retardant of the present invention greatly.
Fire retardant of the present invention is the light brown acicular crystal, and fusing point is 185～186 ℃, and heat decomposition temperature is 240 ℃, is lower than 250～350 ℃ of the pyrolysis temperature range of acrylic fibers.The basic demand that this meets the fire retardant performance fully promptly requires fire retardant preferentially to be decomposed by fire proofing, so just can play necessary fire retardation.Contain three kinds of highly effective flame-retardant compositions in the fire retardant of the present invention simultaneously: phosphorus, sulphur and nitrogen, in thermal decomposition process, described three kinds of flame-retardant compositions can be brought into play cooperative effect, can strengthen the fire retardation of fire retardant for acrylic fibers greatly.Testing vertical flammability shows that when the content of fire retardant of the present invention in acrylic fibers was 20%, its limited oxygen index can have good flame-retardant effect up to 28.Fire retardant of the present invention is water insoluble, but is soluble in chloroform or acetonitrile, N, dinethylformamide and dimethyl sulfoxide (DMSO); Be slightly soluble in ethanol and acetone.Because the fire retardant that is synthesized is nonpolar, and water presents polarity, according to the similar compatibility principle, the fire retardant that is synthesized is water insoluble as can be known, therefore fire retardant of the present invention can water-fastly be washed, also promptly when being soaked in water, fire retardant of the present invention still can keep its anti-flaming function, thereby has strengthened its fire-retardant effect, reduced its service condition and prolonged its duration of fire resistance.
The present invention has designed the manufacture method of described fire retardant simultaneously.The process route of this method is: the O that at first with mol ratio is 2: 1, O-diethyl sulfo-phosphoryl chloride and p-phenylenediamine (PPD) are dissolved in chloroform or the acetonitrile, add the p-phenylenediamine (PPD) amount 0.1～0.5% catalyst 4-dimethylamino naphthyridine and with the equimolar acid binding agent triethylamine of p-phenylenediamine (PPD), under 0～50 ℃ of condition, but preferred reaction conditions is 0～5 ℃ of ice-water bath, reaction 3～5h, stop reaction, the washing products therefrom, washing times is as the criterion with the salt of cleaning in the system (triethylamine hydrochloride), general washing gets final product for three times, use acetone recrystallization again, about pneumatic conveying drying 24h after, can obtain fire retardant of the present invention: 1,4-(O, O-diethyl sulfo-phosphoryl imido grpup) benzene.The manufacture method productive rate of fire retardant of the present invention can reach 60～90%.
Fire retardant of the present invention can be used as fire-retardant interpolation component and is exclusively used in the production technology of acrylic fiber, the addition of fire retardant is 15～20% of a polyacrylonitrile composition weight, has the traditional handicraft of being applicable to, characteristics such as easy to use, special in it has the feature of high-efficiency low-toxicity, therefore can realize green production.The production technology that is used for acrylic fiber with conventional flame retardant is compared, to reach identical LOI value is benchmark, fire retardant of the present invention has lower use amount in the acrylic fiber production technology, help reducing production costs, also help green production and consumption, the acrylic fiber of gained also has higher physical and mechanical properties simultaneously, is convenient to further processing and uses.
The present invention does not address is applicable to prior art.
Provide specific embodiments of the invention below, but protection domain of the present invention is not subjected to the restriction of embodiment:
Embodiment 1:
Magnetic stirring apparatus is being housed, reflux condensing tube, thermometer, in the four neck round-bottomed flasks of the 100mL of constant pressure funnel, add 5.407g (0.05mol) p-phenylenediamine (PPD) and 30mL chloroform, under ice-water bath (5 ℃) condition, the triethylamine that adds 0.0054～0.027g 4-dimethylamino naphthyridine and 14.46mL (0.1mol), then 15.72mL (0.1mol) diethyl sulfo-phosphoryl chloride is packed in the constant pressure funnel, and be controlled in 2 hours and drip off, continue reaction 1 hour, obtain pale solid, filter, wash three times, do recrystallization with acetone again, behind the pneumatic conveying drying 24h, can get the light brown acicular crystal, fire retardant 1 promptly of the present invention, 4-(O, O-diethyl sulfo-phosphoryl imido grpup.This technological design fire retardant productive rate is 78%.Through test, the fusing point of this fire retardant is 185 ℃, and heat decomposition temperature is 240 ℃.
Embodiment 2:
Electric mixer is being housed, reflux condensing tube, thermometer, add 108.14g (1mol) p-phenylenediamine (PPD) and 200mL acetonitrile in the 1000mL round-bottomed flask of constant pressure funnel, the triethylamine that under ice-water bath (4 ℃) condition, adds 0.3g 4-dimethylamino naphthyridine and 290mL (2mol), add 314.35mL (2mol) diethyl sulfo-phosphoryl chloride in the constant pressure funnel at twice, slowly splash in the reaction bulb, react after 3 hours, stop reaction, obtain pale solid, filter, washing, recrystallization is done with acetone in dry back, pneumatic conveying drying 24h can get the light brown acicular crystal, fire retardant 1 promptly of the present invention, 4-(O, O-diethyl sulfo-phosphoryl imido grpup benzene.This technological design fire retardant productive rate is 75%.Through test, the fusing point of this fire retardant is 186 ℃, and heat decomposition temperature is 240 ℃.
Embodiment 3:
Electric mixer is being housed, reflux condensing tube, thermometer, add 0.5g (0.005mol) p-phenylenediamine (PPD) and 5mL acetonitrile in the round-bottomed flask of the 50mL of constant pressure funnel, the triethylamine that under ice-water bath (1 ℃) condition, adds 0.002g 4-dimethylamino naphthyridine and 2.16mL (0.015mol), 1.57mL (0.01mol) diethyl sulfo-phosphoryl chloride was dripped off in 2 hours, and then after reacting 1 hour, finish reaction, obtain pale solid, filter, washing, recrystallization is done with acetone in dry back, pneumatic conveying drying 24h, can get the light brown acicular crystal, be fire retardant 1 of the present invention, 4-(O, O-diethyl sulfo-phosphoryl imido grpup) benzene.This technological design fire retardant productive rate is 81%.Through test, the fusing point of this fire retardant is 186 ℃, and heat decomposition temperature is 240 ℃.
Embodiment 4:
Electric mixer is being housed, reflux condensing tube, thermometer, add 2g (0.018mol) p-phenylenediamine (PPD) and 20mL chloroform in the round-bottomed flask of the 50mL of constant pressure funnel, the triethylamine that under ice-water bath (0 ℃) condition, adds 0.01g 4-dimethylamino naphthyridine and 2.61mL (0.04mol), 5.65mL (0.036mol) diethyl sulfo-phosphoryl chloride was dripped off in 2.5 hours, and then after reacting 1 hour, finish reaction, obtain pale solid, filter, washing, recrystallization is done with acetone in dry back, pneumatic conveying drying 24h, can get the light brown acicular crystal, be fire retardant 1 of the present invention, 4-(O, O-diethyl sulfo-phosphoryl imido grpup) benzene.This technological design fire retardant productive rate is 89%.Through test, the fusing point of this fire retardant is 186 ℃, and heat decomposition temperature is 240 ℃.
Embodiment 5:
Electric mixer is being housed, reflux condensing tube, thermometer, add 2g (0.018mol) p-phenylenediamine (PPD) and 20mL chloroform in the round-bottomed flask of the 50mL of constant pressure funnel, the triethylamine that under 50 ℃ of conditions, adds 0.01g 4-dimethylamino naphthyridine and 2.61mL (0.04mol), 5.65mL (0.036mol) diethyl sulfo-phosphoryl chloride was dripped off in 2.5 hours, and then after reacting 1 hour, finish reaction, obtain pale solid, filter, washing, do recrystallization with acetone, pneumatic conveying drying 24h, can get the light brown acicular crystal, be fire retardant 1 of the present invention, 4-(O, O-diethyl sulfo-phosphoryl imido grpup) benzene.This technological design fire retardant productive rate is 60%.Through test, the fusing point of this fire retardant is 185 ℃, and heat decomposition temperature is 240 ℃.
Embodiment 6
It is 15% that fire retardant of the present invention adds component, with traditional acrylic fiber production process technology (referring to Zhu Qingsong etc., fire-retardant polyacrylonitrile fiber and manufacture method thereof, CN1566421A), production flame-retardant acrylic fibre fiber of the present invention smoothly.After measured, the LOI value of this flame-retardant acrylic fibre fiber can reach 26.5, has good physical and mechanical properties, and low toxic and environment-friendly.
Embodiment 7
It is 20% that fire retardant of the present invention adds component, and with traditional acrylic fiber production process, technology is with embodiment 6, smoothly production flame-retardant acrylic fibre fiber of the present invention.After measured, the LOI value of this flame-retardant acrylic fibre fiber has good physical and mechanical properties up to 28, and low toxic and environment-friendly.
Claims (4)
1. fire retardant, its molecular formula is C
14H
26O
4P
2S
2N
2, chemical structural formula is:
Called after 1,4-(O, O-diethyl sulfo-phosphoryl imido grpup) benzene.
2. the manufacture method of the described fire retardant of claim 1, it adopts following technology: the O that with mol ratio is 2: 1, O-diethyl sulfo-phosphoryl chloride and p-phenylenediamine (PPD) are dissolved in chloroform or the acetonitrile, the catalyst 4-dimethylamino naphthyridine that adds p-phenylenediamine (PPD) amount 0.1～0.5%, and with the equimolar acid binding agent triethylamine of p-phenylenediamine (PPD), under 0～50 ℃ of condition, reaction 3～5h, after stopping reaction, washing net income product is used acetone recrystallization again, behind the pneumatic conveying drying 24h, promptly can be made into described fire retardant: 1,4-(O, O-diethyl sulfo-phosphoryl imido grpup) benzene.
3. according to the manufacture method of the described fire retardant of claim 2, it is characterized in that described reaction condition is 0～5 ℃ of ice-water bath.
4. the purposes of the described fire retardant of claim 1 is characterized in that described fire retardant is exclusively used in the acrylic fiber production technology, and the addition of fire retardant is 15～20% of a polyacrylonitrile composition weight.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101701423B (en) * | 2009-10-28 | 2011-06-08 | 长春工业大学 | Phosphorus flame retardant for viscose fibers and production method and application thereof |
| CN109438509A (en) * | 2018-12-10 | 2019-03-08 | 天津工业大学 | Phosphorus containing diazanyl-nitrogen-sulfur type antibacterial flame-retardant agent and its preparation method and application |
| CN114315896A (en) * | 2021-12-09 | 2022-04-12 | 湖北大学 | 2- (diphenyl thiophosphoryl) succinate and synthesis method and application thereof |
-
2007
- 2007-07-17 CN CN 200710058164 patent/CN101086136A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101701423B (en) * | 2009-10-28 | 2011-06-08 | 长春工业大学 | Phosphorus flame retardant for viscose fibers and production method and application thereof |
| CN109438509A (en) * | 2018-12-10 | 2019-03-08 | 天津工业大学 | Phosphorus containing diazanyl-nitrogen-sulfur type antibacterial flame-retardant agent and its preparation method and application |
| CN109438509B (en) * | 2018-12-10 | 2021-09-14 | 天津工业大学 | Phosphorus-nitrogen-sulfur type antibacterial flame retardant containing hydrazino group and preparation method and application thereof |
| CN114315896A (en) * | 2021-12-09 | 2022-04-12 | 湖北大学 | 2- (diphenyl thiophosphoryl) succinate and synthesis method and application thereof |
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