CN103265575A - Triazinyl triphenyl isopropyl phosphinate compound and preparation method thereof - Google Patents
Triazinyl triphenyl isopropyl phosphinate compound and preparation method thereof Download PDFInfo
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- CN103265575A CN103265575A CN2013102191136A CN201310219113A CN103265575A CN 103265575 A CN103265575 A CN 103265575A CN 2013102191136 A CN2013102191136 A CN 2013102191136A CN 201310219113 A CN201310219113 A CN 201310219113A CN 103265575 A CN103265575 A CN 103265575A
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Abstract
The invention relates to a triazinyl triphenyl isopropyl phosphinate compound and a preparation method thereof. The structure of the compound is shown in the specification. The preparation method comprises the steps of controlling the molar ratio of cyanuric chloride to phenyl diisopropyl phosphinate to be (1:3)-(1:4), and dropping phenyl diisopropyl phosphinate in a certain concentration of solution of an organic solvent of cyanuric chloride in three times; and controlling the temperature to be 35-45 DEG C and stirring to react for one hour for the first time, reacting for one hour at 60-70 DEG C for the second time, reacting for 3-5 hours at 85-90 DEG C for the last time, distilling out the organic solvent, distilling out a few low-boiling-point substances under reduced pressure, and purifying the substances, thus obtaining 2,4,6-tri(O-isopropyl-phenylphosphinyl)-1,3,5-triazinyl. The product belongs to halogen-free phosphorus-nitrogen synergistic flame retardants, has high flame retardance and is suitable to serve as the flame retardant of polyester PBT (polybutylene terephthalate), polyester PET (polyethylene terephthalate), polyvinyl chloride, polyurethane, epoxy resins, unsaturated resins and the like. The preparation method is simple in process, low in equipment investment and easy to achieve industrial production.
Description
Technical field
The present invention relates to a kind of phosphorus, nitrogen synergistic fire retardant triazine triphenyl phospho acid isopropyl ester compound and preparation method thereof; be specifically related to a kind of 2; 4; 6-three (O-sec.-propyl-phenyl time phosphono)-1; 3; 5-triaizine compounds and preparation method thereof, this compound is suitable for the fire retardant of polyester PBT, polyester PET, polyvinyl chloride, urethane, Resins, epoxy and unsaturated polyester etc.
Background technology
Along with the fast development of macromolecular material, synthesized polymer material being used in the middle of the every field more and more widely.Because the inflammableness of these materials, normal presence of fire brings harm can for people's life and property, has therefore promoted developing rapidly of flame-retarded technology.At present the direction of development is, perfect along with fire-retardant rules is more and more higher to the influence of environment when requiring fire retardant usefulness high, so flame-retarded technology is also towards nontoxic, low cigarette, aspect development such as efficient.Many ignition-proof elements are collaborative or composite to be the effective way that improves flame-retarded efficiency, and its phosphorus, nitrogen synergistic fire retardant are the research directions that realizes the nontoxic or low toxicity of fire retardant.
The invention discloses a kind of is the method for feedstock production phosphorus, nitrogen synergistic fire retardant triazine triphenyl phospho acid isopropyl ester compound with cyanuric chloride and phenyl phosphinic acid diisopropyl ester, this product structure has good symmetry, planar conjugate stability, also contain stable C-P key, decomposition temperature is higher, polyester structure and macromolecular material have good consistency, the high temperature process of energy adaptation material has vast market and uses and DEVELOPMENT PROSPECT.
Summary of the invention
One of purpose of the present invention be to propose a kind of phosphorus, nitrogen collaborative 2,4,6-three (O-sec.-propyl-phenyl time phosphono)-1,3,5-triazines compound, its flame-retarded efficiency height can overcome deficiency of the prior art.
For achieving the above object, the present invention has adopted following technical scheme:
2,4,6-three (O-sec.-propyl-phenyl time phosphono)-1,3,5-triazines compound is characterized in that the structure of this compound is shown below:
Another object of the present invention is to propose a kind of 2,4,6-three (O-sec.-propyl-phenyl time phosphono)-1,3; the preparation method of 5-triaizine compounds, its technology is simple, be easy to large-scale production, and raw material is cheap and easy to get; facility investment is few, and is with low cost, and this method is:
The mol ratio of control cyanuric chloride and phenyl phosphinic acid diisopropyl ester was divided the phenyl phosphinic acid diisopropyl ester in the solution of the organic solvent that splashes into certain density cyanuric chloride for three times at 1: 3～1: 4.At first, splash into the phenyl phosphinic acid diisopropyl ester of 1 times of mol ratio, control temperature at 35 ℃～45 ℃, stirring reaction 1h; Then be warming up to 60 ℃～70 ℃, splash into the phenyl phosphinic acid diisopropyl ester of 1 times of mol ratio again, stirring reaction 1h; And then be warming up to 85 ℃～90 ℃, and splashing into the phenyl phosphinic acid diisopropyl ester of 1～2 times of mol ratio again, insulation reaction 3～5h distills out organic solvent; decompression steams a small amount of low boilers again, and purified processing gets 2,4; 6-three (O-sec.-propyl-phenyl time phosphono)-1,3,5-triazines.
The solution of the organic solvent of aforesaid certain density cyanuric chloride is that the quality gram of cyanuric chloride is 1: 6～1: 15 with volume of organic solvent milliliter ratio.
Aforesaid organic solvent is dioxane, ethylene glycol diethyl ether or toluene.
The aforesaid purified ethyl acetate (grams per milliliter) that adds 2～2.5 times of quality producies that is treated to; stirring is fully dissolved it; dripping sherwood oil is 1～1.5 times (milliliter/milliliter) of ethyl acetate approximately, and the product crystallization is separated out fully, filters; vacuum-drying; get 2,4,6-three (O-sec.-propyl-phenyl time phosphono)-1; 3,5-triazine.
Of the present invention 2,4,6-three (O-sec.-propyl-phenyl time phosphono)-1; 3,5-triazine is white or faint yellow solid, and the product yield is 93.4%～96.7%; fusing point is 115 ℃; decomposition temperature: (225 ± 5) ℃, it is suitable for the fire retardant of polyester PBT, polyester PET, polyvinyl chloride, urethane, Resins, epoxy and unsaturated polyester etc., 2; 4; preparation technology's principle of 6-three (O-sec.-propyl-phenyl time phosphono)-1,3,5-triazines is shown below:
Compared with prior art, beneficial effect of the present invention is:
1. of the present invention 2,4,6-three (O-sec.-propyl-phenyl time phosphono)-1,3; the 5-triazine is phosphorus, the agent of nitrogen collaborative type flame-retardant, cooperative flame retardant usefulness height, and structural symmetry is good, and product is stable; decomposition temperature is higher, and has the consistency of polyester structure and macromolecular material good, has plasticity preferably concurrently.
2. of the present invention 2,4,6-three (O-sec.-propyl-phenyl time phosphono)-1,3,5-triazines compound belongs to the efficient halogen-free anti-inflaming agent and has good applied environment friendly.
3. of the present invention 2,4, the preparation technology of 6-three (O-sec.-propyl-phenyl time phosphono)-1,3,5-triazines is simple, easy to control, and facility investment is few, and cost is low, is easy to carry out large-scale production, has good economic benefits again.
Description of drawings
For structure and the performance spy who further specifies product provides following accompanying drawing.
1,2,4, the infrared spectrogram of 6-three (O-sec.-propyl-phenyl time phosphono)-1,3,5-triazines sees Figure of description Fig. 1 for details.
Fig. 1 shows, at 2980cm
-1, 2935cm
-1The place is the stretching vibration peak of c h bond, 1124cm
-1The place is the stretching vibration peak of C-O key, 989cm
-1The place is the stretching vibration peak of P-O key, 1236cm
-1The place is the stretching vibration peak of P=O key, 751cm
-1The stretching vibration peak of the P-C of place key, 1667cm
-1The stretching vibration peak of the C=N of place key, 3058cm
-1The place is the stretching vibration peak of the c h bond on the phenyl ring.
2,2,4, the nuclear magnetic spectrum figure of 6-three (O-sec.-propyl-phenyl time phosphono)-1,3,5-triazines sees Figure of description Fig. 2 for details.
Fig. 2 shows, makes solvent with deuterochloroform, and chemical shift δ 1.21～1.57 places are-CH
3Go up the methyl 3H peak that links to each other with carbon; δ 4.57～5.14 is-methyne H peak that CH-links to each other with oxygen, and δ 7.39～8.17 is P-C
6H
5Last phenyl ring 5H peak.
Specific embodiment
Below in conjunction with embodiment technical scheme of the present invention is described further.
Embodiment 1 is in the 100ml there-necked flask that agitator, thermometer and efficient reflux condensing tube are housed, catch up with the interior air of most bottle with nitrogen, add 3.7g (0.020mol) cyanuric chloride and 40ml dioxane, stirring and dissolving, at first, 5.1g (0.020mol) phenyl phosphinic acid diisopropyl ester is added drop-wise in the solution of cyanuric chloride, controls temperature at 35 ℃, stirring reaction 1h; Then be warming up to 60 ℃, splash into 5.1g (0.020mol) phenyl phosphinic acid diisopropyl ester again, insulation reaction 1h; And then be warming up to 85 ℃, and splashing into the phenyl phosphinic acid diisopropyl ester of 5.1g (0.020mol) again, insulation reaction 5h distills out dioxane (reclaim and use); decompression steams a small amount of low boilers again, then is cooled to 50 ℃, adds ethyl acetate 30ml; stirring is fully dissolved it, drips the about 32ml of sherwood oil, and the product crystallization is separated out fully; filter, vacuum-drying gets 2; 4,6-three (O-sec.-propyl-phenyl time phosphono)-1,3; 5-triazine, productive rate are 93.4%, and decomposition temperature is 225 ℃.
Embodiment 2 is in the 100ml there-necked flask that agitator, thermometer and efficient reflux condensing tube are housed, catch up with the interior air of most bottle with nitrogen, add 3.7g (0.020mol) cyanuric chloride and 40ml dioxane, stirring and dissolving, at first, 5.1g (0.020mol) phenyl phosphinic acid diisopropyl ester is added drop-wise in the solution of cyanuric chloride, controls temperature at 40 ℃, stirring reaction 1h; Then be warming up to 60 ℃, splash into 5.1g (0.020mol) phenyl phosphinic acid diisopropyl ester again, insulation reaction 1h; And then be warming up to 85 ℃; splash into the phenyl phosphinic acid diisopropyl ester of 6.1g (0.024mol) again; insulation reaction 4h distills out dioxane (reclaim and use), and decompression steams excessive phenyl phosphinic acid diisopropyl ester (reclaim and use) again; then be cooled to 50 ℃; add ethyl acetate 30ml, stirring is fully dissolved it, drips the about 30ml of sherwood oil; the product crystallization is separated out fully; filter, vacuum-drying gets 2; 4; 6-three (O-sec.-propyl-phenyl time phosphono)-1,3,5-triazines; productive rate is 96.7%, and decomposition temperature is 225 ℃.
Embodiment 3 is in the 100ml there-necked flask that agitator, thermometer and efficient reflux condensing tube are housed, catch up with the interior air of most bottle with nitrogen, add 3.7g (0.020mol) cyanuric chloride and 40ml ethylene glycol diethyl ether, stirring and dissolving, at first, 5.1g (0.020mol) phenyl phosphinic acid diisopropyl ester is added drop-wise in the solution of cyanuric chloride, controls temperature at 40 ℃, stirring reaction 1h; Then be warming up to 65 ℃, splash into 5.1g (0.020mol) phenyl phosphinic acid diisopropyl ester again, insulation reaction 1h; And then be warming up to 85 ℃; splash into the phenyl phosphinic acid diisopropyl ester of 7.1g (0.028mol) again; insulation reaction 4h distills out ethylene glycol diethyl ether (reclaim and use), and decompression steams excessive phenyl phosphinic acid diisopropyl ester (reclaim and use) again; then be cooled to 50 ℃; add ethyl acetate 35ml, stirring is fully dissolved it, drips the about 40ml of sherwood oil; the product crystallization is separated out fully; filter, vacuum-drying gets 2; 4; 6-three (O-sec.-propyl-phenyl time phosphono)-1,3,5-triazines; productive rate is 96.1%, and decomposition temperature is 225 ℃.
Embodiment 4 is in the 100ml there-necked flask that agitator, thermometer and efficient reflux condensing tube are housed, catch up with the interior air of most bottle with nitrogen, add 3.7g (0.020mol) cyanuric chloride and 40ml toluene, stirring and dissolving, at first, 5.1g (0.020mol) phenyl phosphinic acid diisopropyl ester is added drop-wise in the solution of cyanuric chloride, controls temperature at 45 ℃, stirring reaction 1h; Then be warming up to 65 ℃, splash into 5.1g (0.020mol) phenyl phosphinic acid diisopropyl ester again, insulation reaction 1h; And then be warming up to 85 ℃; splash into the phenyl phosphinic acid diisopropyl ester of 8.1g (0.032mol) again; insulation reaction 5h distills out toluene (reclaim and use), and decompression steams excessive phenyl phosphinic acid diisopropyl ester (reclaim and use) again; then be cooled to 50 ℃; add ethyl acetate 35ml, stirring is fully dissolved it, drips the about 37ml of sherwood oil; the product crystallization is separated out fully; filter, vacuum-drying gets 2; 4; 6-three (O-sec.-propyl-phenyl time phosphono)-1,3,5-triazines; productive rate is 95.7%, and decomposition temperature is 225 ℃.
Embodiment 5 is in the 100ml there-necked flask that agitator, thermometer and efficient reflux condensing tube are housed, catch up with the interior air of most bottle with nitrogen, add 3.7g (0.020mol) cyanuric chloride and 40ml ethylene glycol diethyl ether, stirring and dissolving, at first, 5.1g (0.020mol) phenyl phosphinic acid diisopropyl ester is added drop-wise in the solution of cyanuric chloride, controls temperature at 40 ℃, stirring reaction 1h; Then be warming up to 65 ℃, splash into 5.1g (0.020mol) phenyl phosphinic acid diisopropyl ester again, insulation reaction 1h; And then be warming up to 90 ℃; splash into the phenyl phosphinic acid diisopropyl ester of 9.1g (0.036mol) again; insulation reaction 4h distills out ethylene glycol diethyl ether (reclaim and use), and decompression steams excessive phenyl phosphinic acid diisopropyl ester (reclaim and use) again; then be cooled to 50 ℃; add ethyl acetate 38ml, stirring is fully dissolved it, drips the about 40ml of sherwood oil; the product crystallization is separated out fully; filter, vacuum-drying gets 2; 4; 6-three (O-sec.-propyl-phenyl time phosphono)-1,3,5-triazines; productive rate is 95.9%, and decomposition temperature is 225 ℃.
Embodiment 6 is in the 100ml there-necked flask that agitator, thermometer and efficient reflux condensing tube are housed, catch up with the interior air of most bottle with nitrogen, add 3.7g (0.020mol) cyanuric chloride and 40ml toluene, stirring and dissolving, at first, 5.1g (0.020mol) phenyl phosphinic acid diisopropyl ester is added drop-wise in the solution of cyanuric chloride, controls temperature at 40 ℃, stirring reaction 1h; Then be warming up to 70 ℃, splash into 5.1g (0.020mol) phenyl phosphinic acid diisopropyl ester again, insulation reaction 1h; And then be warming up to 90 ℃; splash into the phenyl phosphinic acid diisopropyl ester of 10.2g (0.040mol) again; insulation reaction 3h distills out toluene (reclaim and use), and decompression steams excessive phenyl phosphinic acid diisopropyl ester (reclaim and use) again; then be cooled to 50 ℃; add ethyl acetate 30ml, stirring is fully dissolved it, drips the about 36ml of sherwood oil; the product crystallization is separated out fully; filter, vacuum-drying gets 2; 4; 6-three (O-sec.-propyl-phenyl time phosphono)-1,3,5-triazines; productive rate is 94.5%, and decomposition temperature is 225 ℃.
Table 1 preparation example main technologic parameters
Also with above-mentioned synthetic 2,4,6-three (O-sec.-propyl-phenyl time phosphono)-1,3,5-triazines is applied among the PBT this case contriver.The limiting oxygen index(LOI) of reference: GB/T2406-2008 " plastics combustibility test method-oxygen index method " test sample product.After simultaneously product is composite with MCA, MPP respectively, join among the PBT according to certain proportioning, extrude batten with XJ-01 type single screw extrusion machine under 220 ℃ at last, batten is of a size of length 15mm, diameter 3mm, the molten drop of test bars and carbon-forming performance.The LOI test result of surveying sees Table 2 to table 4.
The flame retardant properties of table 2 product in PBT
Table 3 product and MCA composite in PBT flame retardant properties
The LOI test result of table 4 product and MPP flame-retardant PBT
Claims (5)
1. a phosphorus, nitrogen synergistic fire retardant triazine triphenyl phospho acid isopropyl ester 2,4,6-three (O-sec.-propyl-phenyl time phosphono)-1,3,5-triazines compound is characterized in that the structure of this compound is shown below:
2. described 2,4 according to claim 1, the preparation method of 6-three (O-sec.-propyl-phenyl time phosphono)-1,3,5-triazines compound is characterized in that this method is:
The mol ratio of control cyanuric chloride and phenyl phosphinic acid diisopropyl ester was divided the phenyl phosphinic acid diisopropyl ester in the solution of the organic solvent that splashes into certain density cyanuric chloride for three times at 1: 3～1: 4; At first, splash into the phenyl phosphinic acid diisopropyl ester of 1 times of mol ratio, control temperature at 35 ℃～45 ℃, stirring reaction 1h; Then be warming up to 60 ℃～70 ℃, splash into the phenyl phosphinic acid diisopropyl ester of 1 times of mol ratio again, sustained reaction 1h; And then be warming up to 85 ℃～90 ℃, and splashing into the phenyl phosphinic acid diisopropyl ester of 1～2 times of mol ratio again, insulation reaction 3～5h distills out organic solvent; decompression steams a small amount of low boilers again, and purified processing gets 2,4; 6-three (O-sec.-propyl-phenyl time phosphono)-1,3,5-triazines.
3. according to claim 2 described 2; 4; 6-three (O-sec.-propyl-phenyl time phosphono)-1; 3; the preparation method of 5-triaizine compounds is characterized in that: the solution of the organic solvent of aforesaid certain density cyanuric chloride is that the quality gram of cyanuric chloride is 1: 6～1: 15 with volume of organic solvent milliliter ratio.
4. described 2,4 according to claim 2, the preparation method of 6-three (O-sec.-propyl-phenyl time phosphono)-1,3,5-triazines compound, it is characterized in that: aforesaid organic solvent is dioxane, ethylene glycol diethyl ether or toluene.
5. described 2,4 according to claim 2,6-three (O-sec.-propyl-phenyl time phosphono)-1; the preparation method of 3,5-triaizine compounds is characterized in that: the aforesaid purified ethyl acetate (grams per milliliter) that adds 2～2.5 times of quality producies that is treated to; stirring is fully dissolved it, and dripping sherwood oil is 1～1.5 times (milliliter/milliliter) of ethyl acetate approximately, and the product crystallization is separated out fully; filter, vacuum-drying gets 2; 4; 6-three (O-sec.-propyl-phenyl time phosphono)-1,3,5-triazines.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111285990A (en) * | 2020-02-07 | 2020-06-16 | 山东理工大学 | Preparation of melamine ring-containing triphosphonic acid and derivative compounded high-performance reactive polyurethane flame retardant |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3410809A (en) * | 1965-05-28 | 1968-11-12 | Monsanto Res Corp | Cn compounds |
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- 2013-06-05 CN CN201310219113.6A patent/CN103265575B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3410809A (en) * | 1965-05-28 | 1968-11-12 | Monsanto Res Corp | Cn compounds |
Non-Patent Citations (2)
| Title |
|---|
| W. HEWERTSON ET AL.: "1,3,5-Triazines. III. Arbuzov reactions of chlorotriazines", 《JOURNAL OF THE CHEMICAL SOCIETY》, 1 January 1963 (1963-01-01), pages 1670 - 1675 * |
| 王彦林等: "2,4,6-三(O,O-二甲基磷酰基)-1,3,5-三嗪的合成及表征", 《兰州理工大学学报》, vol. 36, no. 3, 30 June 2010 (2010-06-30), pages 78 - 80 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111285990A (en) * | 2020-02-07 | 2020-06-16 | 山东理工大学 | Preparation of melamine ring-containing triphosphonic acid and derivative compounded high-performance reactive polyurethane flame retardant |
| CN111285990B (en) * | 2020-02-07 | 2021-11-05 | 山东理工大学 | Preparation of triazine ring-containing triphosphonic acid and derivative compound high-performance reactive polyurethane flame retardant |
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