CN106866683A - A kind of preparation method of the equal ipazine of bromo - Google Patents
A kind of preparation method of the equal ipazine of bromo Download PDFInfo
- Publication number
- CN106866683A CN106866683A CN201710011597.3A CN201710011597A CN106866683A CN 106866683 A CN106866683 A CN 106866683A CN 201710011597 A CN201710011597 A CN 201710011597A CN 106866683 A CN106866683 A CN 106866683A
- Authority
- CN
- China
- Prior art keywords
- equal
- ipazine
- bromo
- tri
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 125000001246 bromo group Chemical group Br* 0.000 title claims abstract description 25
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 150000007530 organic bases Chemical class 0.000 claims abstract description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- 238000001914 filtration Methods 0.000 claims abstract description 8
- 239000011259 mixed solution Substances 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 8
- 238000003756 stirring Methods 0.000 claims abstract description 8
- 238000000967 suction filtration Methods 0.000 claims abstract description 8
- 238000010792 warming Methods 0.000 claims abstract description 8
- -1 ipazine compound Chemical class 0.000 claims description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 claims 1
- BSWWXRFVMJHFBN-UHFFFAOYSA-N 2,4,6-tribromophenol Chemical compound OC1=C(Br)C=C(Br)C=C1Br BSWWXRFVMJHFBN-UHFFFAOYSA-N 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- LLZHDFDRBQXUEW-UHFFFAOYSA-N phenol 1,2,3-tribromobenzene Chemical compound C1(=CC=CC=C1)O.BrC=1C(=C(C=CC1)Br)Br LLZHDFDRBQXUEW-UHFFFAOYSA-N 0.000 claims 1
- 239000003063 flame retardant Substances 0.000 abstract description 13
- OUCSIUCEQVCDEL-UHFFFAOYSA-N 2,3,4-tribromophenol Chemical compound OC1=CC=C(Br)C(Br)=C1Br OUCSIUCEQVCDEL-UHFFFAOYSA-N 0.000 abstract description 5
- 230000007062 hydrolysis Effects 0.000 abstract description 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 2
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- 239000000463 material Substances 0.000 description 3
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical class N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
- 229910021502 aluminium hydroxide Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012757 flame retardant agent Substances 0.000 description 2
- 150000003918 triazines Chemical class 0.000 description 2
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 229910000410 antimony oxide Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001649 bromium compounds Chemical group 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- WHHGLZMJPXIBIX-UHFFFAOYSA-N decabromodiphenyl ether Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br WHHGLZMJPXIBIX-UHFFFAOYSA-N 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 239000000413 hydrolysate Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/16—Peri-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The present invention relates to fire-retardant FRW field, a kind of specific preparation method of the equal ipazine of bromo.It is characterized in that：By tribromphenol, 2, the equal ipazine of 5,8 trichlorines is added to super dry 1, in 4 dioxane solvents, stirring, to mixed solution and dripping organic base, is warming up to 100~110 DEG C and reacts 12~24 hours, it is cooled to room temperature, then organic basis of hydrochloride is separated by filtration, is washed, suction filtration, dry, obtain the equal ipazine product of bromo；The ratio between mole of tribromphenol, the equal ipazine of 2,5,8 trichlorines and organic base is 3.0~3.4：0.8~1.2：1.8~2.2.Strictly removed water in course of reaction, it is to avoid the equal ipazine hydrolysis of 2,5,8 trichlorines.
Description
Technical field
The present invention relates to technical field of flame retardant agent preparation, a kind of specific preparation method of the equal ipazine of bromo.
Background technology
In recent years, with the continuous enhancing of people's awareness of the importance of fire prevention, all fire safety as the weight for working in all trades and professions
Point.Used as fireproof conventional meanses, fire retardant is widely added in the middle of multiple material.The most popular fire retardant in the whole world
Aluminium hydroxide and antimony oxide in inorganic combustion inhibitor etc., organic fire-retardant includes halogenated flame retardant and phosphorous flame-retardant
Agent.Wherein, the maximum fire retardant of consumption makes aluminium hydroxide, accounts for the 33% of the total proportion in fire retardant market；Secondly it is bromide fire retardant,
Account for the 21% of total proportion.
Bromide fire retardant is a series of general name of bromine-containing compounds, including tetrabromobisphenol A, deca-BDE, ten bromines
Diphenylethane etc..Brominated flame retardant is heated can produce HBr, can participate directly in the middle of the chemical reaction of burning, in capture reaction
The free radical of generation, terminates chain reaction, and this mode of action the most direct can play height in the case of little addition
The fire retardation of effect.In addition, the density of HBr gases is larger, can play a part of to completely cut off air.Nowadays, in building heat preservation material
Bromide fire retardant is all widely used in material, electronic equipment, household articles.In numerous bromide fire retardants, brominated triazine with
Its superior flame retardant property, to process equipment and environment negative effect it is smaller the features such as be widely studied [CN103275025A,
US5965731、US4039538、CN1888014、US5696302、US5907040].Similar with brominated triazine, bromo grass is afraid of
Tianjin is also a kind of efficient bromide fire retardant, however, not reporting correlative study both at home and abroad so far.
The content of the invention
The technical problems to be solved by the invention are to provide a kind of equal ipazine compound of bromo.
It is another object of the present invention to provide the preparation method of the equal ipazine compound of above-mentioned bromo.
The technical problems to be solved by the invention are achieved by the following technical programs：A kind of equal ipazine chemical combination of bromo
Thing, molecular formula is C24H6Br9N7O2, structural formula is as follows：
The fire retardant is white powder；Molecular weight：1159.49；Proportion：2.51g/cm3(20℃)；Fusing point：233.7
℃；323 DEG C of decomposition temperature.
A kind of preparation method of the equal ipazine compound of bromo：By tribromphenol, the chloro- equal ipazines of 2,5,8- tri- add to
In super dry Isosorbide-5-Nitrae-dioxane solvent, stirring, to mixed solution and dripping organic base, is warming up to back flow reaction for a period of time, cold
But to room temperature, organic basis of hydrochloride is then separated by filtration, is washed, suction filtration, dried, obtain the equal ipazine product of bromo.
Reaction equation is：
Further, the ratio between the tribromphenol, mole of 2,5,8- tri- chloro- equal ipazines and organic base for 3.0~
3.4：0.8~1.2：1.8~2.2.
It is further preferred that the tribromphenol, 2,5,8- tri- chloro- equal ipazines are preferably with the mol ratio of organic base
3.2：1.0：2.0.
Further, the heating-up temperature is 100~120 DEG C.
The reaction time is 12~24 hours.
The organic base is at least one in triethylamine, tripropyl amine (TPA) and tri-n-butylamine.
The present invention has the advantages that：
Reacted using anhydrous system, it is to avoid the hydrolysis of 2,5,8- tri- chloro- equal ipazines, the product for obtaining is pure
Degree is high, without hydrolysate.The HCl for reacting generation is neutralized with organic base, it is ensured that reaction is smoothed out.One kind of the invention
The equal ipazine compounds process for production thereof of bromo is simple, and pollution-free, without side reaction, product purity is high, and heat endurance is good.
Brief description of the drawings
Fig. 1 is a kind of equal ipazine compound of bromo of the invention1H nuclear magnetic resonance maps.
Fig. 2 is a kind of infared spectrum of the equal ipazine compound of bromo of the invention.
Specific embodiment
The present invention is described in further detail with embodiment below in conjunction with accompanying drawing, it should be pointed out that its purpose only exists
In being best understood from the protection domain that present disclosure is not intended to limit the present invention.
Embodiment 1
0.16mol tribromphenols, the chloro- equal ipazines of 0.05mol 2,5,8- tri- are added to the super dry 1,4- dioxane of 200ml
In solvent, stirring, to mixed solution and dripping 0.1mol triethylamines, is warming up to 120 degrees Celsius and reacts 24 hours, is cooled to room
Temperature, is then separated by filtration organic basis of hydrochloride, washing, and suction filtration is dried, and obtains the equal ipazine products C of bromo24H6Br9N7O2, produce
Rate 87.1% (is based on the chloro- equal ipazines of 2,5,8- tri-).
The equal ipazine compound of bromo prepared by Example 1 is carried out1H nuclear magnetic resonance test, its collection of illustrative plates as shown in figure 1,
Main absworption peak is located at 7.57ppm.
The equal ipazine compound of bromo prepared by Example 1 carries out infrared test, and its collection of illustrative plates is as shown in Fig. 2 main
Absworption peak is 1653cm-1,1618cm-1, 1587cm-1, 1493cm-1, 1435cm-1, 1391cm-1, 1341cm-1, 1260cm-1,
1105cm-1, 767cm-1, 660cm-1, 602cm-1, 541cm-1。
Embodiment 2
0.17mol tribromphenols, the chloro- equal ipazines of 0.06mol 2,5,8- tri- are added to the super dry 1,4- dioxane of 200ml
In solvent, stirring, to mixed solution and dripping 0.11mol triethylamines, is warming up to 100 degrees Celsius and reacts 12 hours, is cooled to room
Temperature, is then separated by filtration organic basis of hydrochloride, washing, and suction filtration is dried, and obtains the equal ipazine products C of bromo24H6Br9N7O2, produce
Rate 81.7% (is based on the chloro- equal ipazines of 2,5,8- tri-).
Embodiment 3
0.15mol tribromphenols, the chloro- equal ipazines of 0.04mol 2,5,8- tri- are added to the super dry 1,4- dioxane of 200ml
In solvent, stirring, to mixed solution and dripping 0.10mol tripropyl amine (TPA)s, is warming up to 110 degrees Celsius and reacts 18 hours, is cooled to room
Temperature, is then separated by filtration organic basis of hydrochloride, washing, and suction filtration is dried, and obtains the equal ipazine products C of bromo24H6Br9N7O2, produce
Rate 78.0% (is based on the chloro- equal ipazines of 2,5,8- tri-).
Embodiment 4
0.15mol tribromphenols, the chloro- equal ipazines of 0.05mol 2,5,8- tri- are added to the super dry 1,4- dioxane of 200ml
In solvent, stirring, to mixed solution and dripping 0.09mol triethylamines, is warming up to 120 degrees Celsius and reacts 12 hours, is cooled to room
Temperature, is then separated by filtration organic basis of hydrochloride, washing, and suction filtration is dried, and obtains the equal ipazine products C of bromo24H6Br9N7O2, produce
Rate 72.2% (is based on the chloro- equal ipazines of 2,5,8- tri-).
Embodiment 5
0.16mol tribromphenols, the chloro- equal ipazines of 0.04mol 2,5,8- tri- are added to the super dry 1,4- dioxane of 200ml
In solvent, stirring, to mixed solution and dripping 0.10mol tri-n-butylamines, is warming up to 100 degrees Celsius and reacts 24 hours, is cooled to room
Temperature, is then separated by filtration organic basis of hydrochloride, washing, and suction filtration is dried, and obtains the equal ipazine products C of bromo24H6Br9N7O2, produce
Rate 67.3% (is based on the chloro- equal ipazines of 2,5,8- tri-).
Above content is to combine specific preferred embodiment further description made for the present invention, it is impossible to assert
Specific implementation of the invention is confined to these explanations.For the person of ordinary skill of the art, can be according to the present invention
Technical scheme and inventive concept, make it is corresponding change and substitute, and performance or purposes are identical, should all be considered as of the invention
Protection domain.
Claims (8)
1. the equal ipazine compound of a kind of bromo, it is characterised in that：Molecular formula is C24H6Br9N7O2；Molecular weight is 1159.49；Than
Weight is 2.51g/cm3(20℃)；Fusing point is 233.7 DEG C；Decomposition temperature is 323 DEG C.
2. the equal ipazine compound of a kind of bromo according to claim 1, it is characterised in that：1H nuclear magnetic resonance spectroscopies are main
Absworption peak be located at 7.57ppm.
3. the preparation method of the equal ipazine compound of a kind of bromo according to claim 1, it is characterised in that：By tribromo-benzene
Phenol, 2,5,8- tri- chloro- equal ipazines are added into super dry Isosorbide-5-Nitrae-dioxane solvent, stirring, organic to mixed solution and dripping
Alkali, is warming up to back flow reaction for a period of time, is cooled to room temperature, is then separated by filtration organic basis of hydrochloride, washing, and suction filtration is dried,
Obtain the equal ipazine product of bromo.
4. the preparation method of the equal ipazine compound of a kind of bromo according to claim 3, it is characterised in that：The tribromo
The ratio between mole of phenol, 2,5,8- tri- chloro- equal ipazines and organic base is 3.0~3.4：0.8~1.2：1.8~2.2.
5. the preparation method of the equal ipazine compound of a kind of bromo according to claim 4, it is characterised in that：The tribromo
Phenol, 2,5,8- tri- chloro- equal ipazines are preferably 3.2 with the mol ratio of organic base：1.0：2.0.
6. the equal ipazine compounds process for production thereof of a kind of bromo according to claim 3, it is characterised in that：The heating temperature
Spend is 100~120 DEG C.
7. the equal ipazine compounds process for production thereof of a kind of bromo according to claim 3, it is characterised in that：During the reaction
Between be 12~24 hours.
8. the equal ipazine compounds process for production thereof of a kind of bromo according to claim 3, it is characterised in that：The organic base
It is at least one in triethylamine, tripropyl amine (TPA) and tri-n-butylamine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710011597.3A CN106866683A (en) | 2017-01-07 | 2017-01-07 | A kind of preparation method of the equal ipazine of bromo |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710011597.3A CN106866683A (en) | 2017-01-07 | 2017-01-07 | A kind of preparation method of the equal ipazine of bromo |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN106866683A true CN106866683A (en) | 2017-06-20 |
Family
ID=59164740
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710011597.3A Pending CN106866683A (en) | 2017-01-07 | 2017-01-07 | A kind of preparation method of the equal ipazine of bromo |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106866683A (en) |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0286478A1 (en) * | 1987-03-31 | 1988-10-12 | Elf Atochem S.A. | Phosphorous-acid salts, their commpositions and their use as fire-proofing agents |
| WO2006034784A1 (en) * | 2004-09-29 | 2006-04-06 | Universität Konstanz | Heptazine derivatives containing phosphorus, method for the production thereof and use thereof as flame retardants |
| CN101223174A (en) * | 2005-07-13 | 2008-07-16 | 医姿挺有限公司 | New derivatives of heptaazaphenalene, methods for obtaining them, and their use as protecting agents against UV radiation |
| CN101228211A (en) * | 2005-06-13 | 2008-07-23 | Zylum投资有限公司专利Ⅱ两合公司 | Silicon - and polysilyl cyamelurates as well as - cyanurates, methods for the production thereof and their use |
| WO2010128166A1 (en) * | 2009-05-08 | 2010-11-11 | Zylum Beteiligungsgesellschaft Mbh & Co. Patente Ii Kg | Halogen-free derivatives of triazine and heptazine |
| WO2014090936A1 (en) * | 2012-12-12 | 2014-06-19 | Zylum Beteiligungsgesellschaft Mbh & Co. Patente Ii Kg | Synergistic composition and use thereof as a flame retardant |
| WO2014173908A1 (en) * | 2013-04-23 | 2014-10-30 | Zylum Beteiligungsgesellschaft Mbh & Co. Patente Ii Kg | Improved composition and use thereof as a flameproofing agent |
| DE102012007529B4 (en) * | 2012-04-17 | 2016-03-31 | Technische Universität Bergakademie Freiberg | Imido-s-heptazine derivatives - Process for their preparation and their uses |
-
2017
- 2017-01-07 CN CN201710011597.3A patent/CN106866683A/en active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0286478A1 (en) * | 1987-03-31 | 1988-10-12 | Elf Atochem S.A. | Phosphorous-acid salts, their commpositions and their use as fire-proofing agents |
| WO2006034784A1 (en) * | 2004-09-29 | 2006-04-06 | Universität Konstanz | Heptazine derivatives containing phosphorus, method for the production thereof and use thereof as flame retardants |
| CN101228211A (en) * | 2005-06-13 | 2008-07-23 | Zylum投资有限公司专利Ⅱ两合公司 | Silicon - and polysilyl cyamelurates as well as - cyanurates, methods for the production thereof and their use |
| CN101223174A (en) * | 2005-07-13 | 2008-07-16 | 医姿挺有限公司 | New derivatives of heptaazaphenalene, methods for obtaining them, and their use as protecting agents against UV radiation |
| WO2010128166A1 (en) * | 2009-05-08 | 2010-11-11 | Zylum Beteiligungsgesellschaft Mbh & Co. Patente Ii Kg | Halogen-free derivatives of triazine and heptazine |
| DE102012007529B4 (en) * | 2012-04-17 | 2016-03-31 | Technische Universität Bergakademie Freiberg | Imido-s-heptazine derivatives - Process for their preparation and their uses |
| WO2014090936A1 (en) * | 2012-12-12 | 2014-06-19 | Zylum Beteiligungsgesellschaft Mbh & Co. Patente Ii Kg | Synergistic composition and use thereof as a flame retardant |
| WO2014173908A1 (en) * | 2013-04-23 | 2014-10-30 | Zylum Beteiligungsgesellschaft Mbh & Co. Patente Ii Kg | Improved composition and use thereof as a flameproofing agent |
Non-Patent Citations (4)
| Title |
|---|
| DINGXUAN MA ET AL.: "Multifunctional Luminescent Porous Organic Polymer for Selectively Detecting Iron Ions and 1,4-Dioxane via Luminescent Turn-off and Turn-on Sensing", 《APPLIED MATERIALS & INTERFACES》 * |
| HANSJUERGEN SCHROEDER ET AL.: "Some Reactions of Cyameluric Chloride", 《JOURNAL OF ORGANIC CHEMISTRY》 * |
| SCHWARZ, MARCUS R.ET AL.: "Crystal structure of triphenyl cyamelurate (2,5,8-triphenoxy-1,3,4,6,7,9,9b-heptaazaphenalene)", 《HETEROCYCLES》 * |
| 钱立军等: "氯化氢脱除法合成三-（三溴苯氧基）-三嗪", 《塑料》 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104072759B (en) | A kind of P-N system expansion reaction type fire retardant and preparation method thereof | |
| CN104945658A (en) | Reaction-type halogen-free flame retardant bis-(p-aminocarboxyphenyl)phenylphosphine oxide and synthetic method thereof | |
| CN102731830A (en) | Nitrogen-containing chloro-polysilicate compound and preparation method thereof | |
| CN102731825B (en) | Chloro- and bromo-containing silicate flame retardant compound and preparation method thereof | |
| CN107501493A (en) | Phosphorus nitrogen expansion type combustion inhibitor and its production and use | |
| CN104725667A (en) | Novel phosphorus and silicon flame retardant with double caged phosphate structure as well as preparation method and application of novel flame retardant | |
| CN110862574A (en) | Efficient smoke-inhibiting magnesium hydroxide/tin compound microcapsule flame retardant and preparation method thereof | |
| CN104961917A (en) | Preparation method of POSS (polyhedral oligomeric silsesquioxane) material and calcium carbonate composite flame retardant material | |
| CN106866683A (en) | A kind of preparation method of the equal ipazine of bromo | |
| CN102731552B (en) | Flame retardant tribromophenoxychloropropoxytri(chloropropyl) silicate compound and preparation method thereof | |
| CN103172666B (en) | The preparation method of the dialkylphosphinic salts that a kind of thermostability is high | |
| CN104497051A (en) | Method for preparing reactive type halogen-free flame retardant for coating | |
| CN104478935A (en) | Preparation method of nitrophenoxy cyclotriphosphazene flame retardant | |
| CN103172665B (en) | Preparation method and application of dialkyl phosphinate with high density and large particle size | |
| CN102140111B (en) | Methyl tri(2-chloropropyl)silane compound and preparation method thereof | |
| CN103754900B (en) | A kind of single dispersing magnesium hydroxide nano-particle preparation method based on carbon nanotube carrier and application | |
| CN108751791A (en) | A kind of fireproof and heat-insulating material and preparation method thereof | |
| CN103524545A (en) | Fire retardant1,3,5-tris(2-hydroxyethyl)isocyanurate 3-silicate-chloride propyl ester compound and preparation method thereof | |
| CN105175775A (en) | Preparation method of POSS material and alumina composite flame retardation material | |
| CN104926882A (en) | Naphthylamido cyclotriphosphazene based flame retardant and preparation method therefor | |
| CN104987349A (en) | Preparation method of POSS material and alkaline metal oxide composite flame retardation material | |
| CN104109246B (en) | A kind of P-N expanding fire retardant and preparation method thereof | |
| CN101319459B (en) | Preparation of magnesium oxide crystal orientation membrane on fire resistant organic fibre | |
| CN104558039A (en) | Phosphorus-nitrogen intumescent flame retardant and preparation method thereof | |
| CN102731555A (en) | Tribromophenoxychloropropoxytri(dichloropropyl)silicate compound and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20170620 |
|
| WD01 | Invention patent application deemed withdrawn after publication |