CN109503662A - The preparation method of viscose rayon combustion inhibitor special - Google Patents
The preparation method of viscose rayon combustion inhibitor special Download PDFInfo
- Publication number
- CN109503662A CN109503662A CN201910031534.3A CN201910031534A CN109503662A CN 109503662 A CN109503662 A CN 109503662A CN 201910031534 A CN201910031534 A CN 201910031534A CN 109503662 A CN109503662 A CN 109503662A
- Authority
- CN
- China
- Prior art keywords
- reaction
- combustion inhibitor
- viscose rayon
- reaction solution
- preparation
- 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
- 238000002485 combustion reaction Methods 0.000 title claims abstract description 17
- 239000003112 inhibitor Substances 0.000 title claims abstract description 17
- 229920000297 Rayon Polymers 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 57
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 48
- WQYSXVGEZYESBR-UHFFFAOYSA-N thiophosphoryl chloride Chemical compound ClP(Cl)(Cl)=S WQYSXVGEZYESBR-UHFFFAOYSA-N 0.000 claims abstract description 20
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000000047 product Substances 0.000 claims abstract description 17
- 239000012065 filter cake Substances 0.000 claims abstract description 16
- 230000035484 reaction time Effects 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims abstract description 9
- 239000011230 binding agent Substances 0.000 claims abstract description 9
- 230000032050 esterification Effects 0.000 claims abstract description 6
- 238000005886 esterification reaction Methods 0.000 claims abstract description 6
- 238000005917 acylation reaction Methods 0.000 claims abstract description 5
- 239000003513 alkali Substances 0.000 claims abstract description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 32
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- 239000000835 fiber Substances 0.000 claims description 3
- 239000003292 glue Substances 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
- 238000003889 chemical engineering Methods 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 31
- 235000011121 sodium hydroxide Nutrition 0.000 description 12
- 238000010792 warming Methods 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 11
- 238000001816 cooling Methods 0.000 description 11
- 238000001514 detection method Methods 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 238000004321 preservation Methods 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 238000000967 suction filtration Methods 0.000 description 11
- 238000000034 method Methods 0.000 description 8
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 241000790917 Dioxys <bee> Species 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657109—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms esters of oxyacids of phosphorus in which one or more exocyclic oxygen atoms have been replaced by (a) sulfur atom(s)
- C07F9/657136—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms esters of oxyacids of phosphorus in which one or more exocyclic oxygen atoms have been replaced by (a) sulfur atom(s) the molecule containing more than one cyclic phosphorus atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Abstract
Chemical engineering of materials technical field of the present invention; more particularly to a kind of preparation method of viscose rayon combustion inhibitor special; the following steps are included: phosphorus thiochloride and neopentyl glycol are 1:(4-8 according to mass ratio by (1)) it is placed in progress acylation reaction in reaction kettle; reaction temperature is 60-80 DEG C; reaction time is 3-6h, obtains reaction solution A；(2) acid binding agent is added in reaction solution A in step (1) again and water carries out esterification, reaction temperature is 85-100 DEG C, reaction time 3-5h, and after reaction plus alkali is adjusted to pH=10, obtains reaction solution B；3) reaction solution B in step (2) is filtered, filtered filter cake is recrystallized through anhydrous methanol, and viscose rayon combustion inhibitor special finished product can be obtained；Reaction time of the invention is short, and production cost is low, and the three wastes are few；And reaction condition is mild, no high-temperature high-voltage reaction, it is highly-safe；Meanwhile finished product purity is high prepared by the present invention, overall yield of reaction are high.
Description
Technical field
The present invention relates to chemical engineering of materials technical fields, and in particular to a kind of preparation method of viscose rayon combustion inhibitor special.
Background technique
2,2'- dioxies [5.5- dimethyl -1,3,2- dioxy phosphorus heterocycle] 2,2'- disulphide, alias NLD-02 are a kind of
Viscose rayon combustion inhibitor special.Its molecular formula is C10H20O5P2S2, chemical structural formula is as follows:
Current synthetic method reported in the literature has: using neopentyl glycol and phosphorus thiochloride as raw material in WO2010049083,3-
Picoline is acid binding agent, and water is added after 50 DEG C of reaction 3h, is prepared into NLD-02, yield then at 60 DEG C of esterifications overnight
85%；For CN101948487 using neopentyl glycol and phosphorus thiochloride as raw material, triethylamine is acid binding agent, and hexamethylene is solvent, at 48 DEG C
Acylation reaction is carried out, then addition water is warming up to 68 DEG C of reaction 10h and obtains NLD-02, yield 82%.The above synthetic method exists
Reaction time of esterification is long, the lower problem of product yield.Therefore, develop that a reaction time is short, process route of high income is
It is necessary.
Summary of the invention
(1) the technical issues of solving
In view of the deficiencies of the prior art, the present invention provides a kind of preparation methods of viscose rayon combustion inhibitor special.
(2) technical solution
In order to achieve the above object, the present invention is achieved by the following technical programs:
A kind of preparation method of viscose rayon combustion inhibitor special, comprising the following steps:
(1) it is 1:(4-8 according to mass ratio by phosphorus thiochloride and neopentyl glycol) it is placed in progress acylation reaction in reaction kettle, instead
Answering temperature is 60-80 DEG C, and reaction time 3-6h obtains reaction solution A；
(2) acid binding agent being added in reaction solution A in step (1) again and water carries out esterification, reaction temperature is 85-100 DEG C,
Reaction time is 3-5h, and after reaction plus alkali is adjusted to pH=10, obtains reaction solution B；
(3) reaction solution B in step (2) is filtered, filtered filter cake is recrystallized through anhydrous methanol, can be obtained viscous
Glue fiber combustion inhibitor special finished product.
Preferential, phosphorus thiochloride and neopentyl glycol are 1:4.5, reaction temperature 70 according to mass ratio in the step (1)
DEG C, reaction time 4h.
Preferential, the molar ratio of the acid binding agent and water and phosphorus thiochloride that are added in the step (2) is followed successively by (1.5-3):
(1.1-1.3): 1.
Preferential, the acid binding agent is any one in triethylamine, sodium carbonate, sodium hydroxide, pyridine and diethylamine.
Preferential, the alkali being added in the step (2) is sodium hydroxide or potassium hydroxide.
Preferential, the mass ratio of anhydrous methanol and filter cake is (8-15) in the step (3): 1.
Wherein, the reaction equation of acylation reaction is as follows in the step (1):
The reaction equation of esterification is as follows in the step (2):
(3) beneficial effect
1, the reaction time of the invention is short, and production cost is low, and the three wastes are few.
2, reaction condition of the invention is mild, no high-temperature high-voltage reaction, highly-safe.
3, glue fiber combustion inhibitor special finished product purity is high of the invention, overall yield of reaction are high.
Specific embodiment
In order to make the object, technical scheme and advantages of the embodiment of the invention clearer, below in conjunction with the embodiment of the present invention,
Technical scheme in the embodiment of the invention is clearly and completely described, it is clear that described embodiment is the present invention one
Divide embodiment, instead of all the embodiments.Based on the embodiments of the present invention, those of ordinary skill in the art are not making
Every other embodiment obtained, shall fall within the protection scope of the present invention under the premise of creative work.
Embodiment 1:
Phosphorus thiochloride 170g is added in the three-necked flask equipped with thermometer, stirring, neopentyl glycol 680g is to slowly warm up to
60 DEG C, 6h is stirred to react under conditions of heat preservation；After time reaches, reaction solution is warming up to 85 DEG C, pyridine 118.5g, water is added
20g after insulated and stirred reacts 5h, adds 30% sodium hydrate aqueous solution to adjust pH=10；Cooling, suction filtration reaction solution, filter cake are added
Anhydrous methanol 1300g recrystallizes to obtain product 155.7g, yield 90%, and liquid chromatographic detection purity is 99%.
Embodiment 2:
Phosphorus thiochloride 170g is added in the three-necked flask equipped with thermometer, stirring, neopentyl glycol 680g is to slowly warm up to
80 DEG C, 3h is stirred to react under conditions of heat preservation；After time reaches, reaction solution is warming up to 85 DEG C, pyridine 118.5g, water is added
20g after insulated and stirred reacts 5h, adds 30% sodium hydrate aqueous solution to adjust pH=10；Cooling, suction filtration reaction solution, filter cake are added
Anhydrous methanol 1300g recrystallizes to obtain product 155.8g, yield 90%, and liquid chromatographic detection purity is 99%.
Embodiment 3:
Phosphorus thiochloride 170g is added in the three-necked flask equipped with thermometer, stirring, neopentyl glycol 680g is to slowly warm up to
80 DEG C, 3h is stirred to react under conditions of heat preservation；After time reaches, reaction solution is warming up to 100 DEG C, pyridine 118.5g, water is added
20g after insulated and stirred reacts 3h, adds 30% sodium hydrate aqueous solution to adjust pH=10；Cooling, suction filtration reaction solution, filter cake are added
Anhydrous methanol 1300g recrystallizes to obtain product 155.9g, yield 90.1%, and liquid chromatographic detection purity is 99%.
Embodiment 4:
Phosphorus thiochloride 170g, neopentyl glycol 1020g are added in the three-necked flask equipped with thermometer, stirring, slowly heats up
To 80 DEG C, 3h is stirred to react under conditions of heat preservation；After time reaches, reaction solution is warming up to 100 DEG C, be added pyridine 118.5g,
Water 20g after insulated and stirred reacts 3h, adds 30% sodium hydrate aqueous solution to adjust pH=10；Cooling, suction filtration reaction solution, filter cake add
Enter anhydrous methanol 1300g and recrystallize to obtain product 155.7g, yield 90%, liquid chromatographic detection purity is 99%.
Embodiment 5:
Phosphorus thiochloride 170g is added in the three-necked flask equipped with thermometer, stirring, neopentyl glycol 680g is to slowly warm up to
80 DEG C, 3h is stirred to react under conditions of heat preservation；After time reaches, reaction solution is warming up to 100 DEG C, pyridine 237g, water is added
20g after insulated and stirred reacts 3h, adds 30% sodium hydrate aqueous solution to adjust pH=10；Cooling, suction filtration reaction solution, filter cake are added
Anhydrous methanol 1300g recrystallizes to obtain product 156g, yield 90.2%, and liquid chromatographic detection purity is 99%.
Embodiment 6:
Phosphorus thiochloride 170g is added in the three-necked flask equipped with thermometer, stirring, neopentyl glycol 680g is to slowly warm up to
80 DEG C, 3h is stirred to react under conditions of heat preservation；After time reaches, reaction solution is warming up to 100 DEG C, pyridine 237g, water is added
20g after insulated and stirred reacts 3h, adds 30% sodium hydrate aqueous solution to adjust pH=10；Cooling, suction filtration reaction solution, filter cake are added
Anhydrous methanol 1300g recrystallizes to obtain product 156g, yield 90.2%, and liquid chromatographic detection purity is 99%.
Embodiment 7:
Phosphorus thiochloride 170g is added in the three-necked flask equipped with thermometer, stirring, neopentyl glycol 680g is to slowly warm up to
80 DEG C, 3h is stirred to react under conditions of heat preservation；After time reaches, reaction solution is warming up to 100 DEG C, pyridine 237g, water is added
30g after insulated and stirred reacts 3h, adds 30% sodium hydrate aqueous solution to adjust pH=10；Cooling, suction filtration reaction solution, filter cake are added
Anhydrous methanol 1300g recrystallizes to obtain product 156g, yield 90.2%, and liquid chromatographic detection purity is 99%.
Embodiment 8:
Phosphorus thiochloride 170g is added in the three-necked flask equipped with thermometer, stirring, neopentyl glycol 680g is to slowly warm up to
80 DEG C, 3h is stirred to react under conditions of heat preservation；After time reaches, reaction solution is warming up to 100 DEG C, pyridine 237g, water is added
30g after insulated and stirred reacts 3h, adds 30% sodium hydrate aqueous solution to adjust pH=10；Cooling, suction filtration reaction solution, filter cake are added
Anhydrous methanol 1500g recrystallizes to obtain product 154g, yield 89%, and liquid chromatographic detection purity is 99.5%.
Embodiment 9:
Phosphorus thiochloride 170g is added in the three-necked flask equipped with thermometer, stirring, neopentyl glycol 680g is to slowly warm up to
80 DEG C, 3h is stirred to react under conditions of heat preservation；After time reaches, reaction solution is warming up to 100 DEG C, pyridine 237g, water is added
30g after insulated and stirred reacts 3h, adds 30% potassium hydroxide aqueous solution to adjust pH=10；Cooling, suction filtration reaction solution, filter cake are added
Anhydrous methanol 1500g recrystallizes to obtain product 154g, yield 89%, and liquid chromatographic detection purity is 99.5%.
Embodiment 10:
Phosphorus thiochloride 170g is added in the three-necked flask equipped with thermometer, stirring, neopentyl glycol 680g is to slowly warm up to
80 DEG C, 3h is stirred to react under conditions of heat preservation；After time reaches, reaction solution is warming up to 100 DEG C, be added triethylamine 151.5g,
Water 30g after insulated and stirred reacts 3h, adds 30% sodium hydrate aqueous solution to adjust pH=10；Cooling, suction filtration reaction solution, filter cake add
Enter anhydrous methanol 1500g and recrystallize to obtain product 154g, yield 89%, liquid chromatographic detection purity is 99.5%.
Embodiment 11:
Phosphorus thiochloride 170g is added in the three-necked flask equipped with thermometer, stirring, neopentyl glycol 680g is to slowly warm up to
80 DEG C, 3h is stirred to react under conditions of heat preservation；After time reaches, reaction solution is warming up to 100 DEG C, sodium carbonate 159g, water is added
30g after insulated and stirred reacts 3h, adds 30% sodium hydrate aqueous solution to adjust pH=10；Cooling, suction filtration reaction solution, filter cake are added
Anhydrous methanol 1500g recrystallizes to obtain product 154g, yield 89%, and liquid chromatographic detection purity is 99.5%.
It should be noted that, in this document, relational terms such as first and second and the like are used merely to a reality
Body or operation are distinguished with another entity or operation, are deposited without necessarily requiring or implying between these entities or operation
In any actual relationship or order or sequence.Moreover, the terms "include", "comprise" or its any other variant are intended to
Non-exclusive inclusion, so that the process, method, article or equipment including a series of elements is not only wanted including those
Element, but also including other elements that are not explicitly listed, or further include for this process, method, article or equipment
Intrinsic element.In the absence of more restrictions, the element limited by sentence "including a ...", it is not excluded that
There is also other identical elements in process, method, article or equipment including the element.
The above embodiments are merely illustrative of the technical solutions of the present invention, rather than its limitations；Although with reference to the foregoing embodiments
Invention is explained in detail, those skilled in the art should understand that: it still can be to aforementioned each implementation
Technical solution documented by example is modified or equivalent replacement of some of the technical features；And these modification or
Replacement, the spirit and scope for technical solution of various embodiments of the present invention that it does not separate the essence of the corresponding technical solution.
Claims (6)
1. a kind of preparation method of viscose rayon combustion inhibitor special, which comprises the following steps:
(1) it is 1:(4-8 according to mass ratio by phosphorus thiochloride and neopentyl glycol) it is placed in progress acylation reaction in reaction kettle, reaction temperature
Degree is 60-80 DEG C, and reaction time 3-6h obtains reaction solution A；
(2) acid binding agent is added in reaction solution A in step (1) again and water carries out esterification, reaction temperature is 85-100 DEG C, reaction
Time is 3-5h, and after reaction plus alkali is adjusted to pH=10, obtains reaction solution B；
(3) reaction solution B in step (2) is filtered, filtered filter cake is recrystallized through anhydrous methanol, and viscose glue fibre can be obtained
Tie up combustion inhibitor special finished product.
2. a kind of preparation method of viscose rayon combustion inhibitor special as described in claim 1, which is characterized in that its feature exists
In phosphorus thiochloride and neopentyl glycol are 1:4.5 according to mass ratio in the step (1), and reaction temperature is 70 DEG C, and the reaction time is
4h。
3. a kind of preparation method of viscose rayon combustion inhibitor special as described in claim 1, which is characterized in that its feature exists
In the molar ratio of the acid binding agent and water and phosphorus thiochloride that are added in the step (2) is followed successively by (1.5-3): (1.1-1.3): 1.
4. a kind of preparation method of viscose rayon combustion inhibitor special as claimed in claim 3, which is characterized in that its feature exists
In the acid binding agent is any one in triethylamine, sodium carbonate, sodium hydroxide, pyridine and diethylamine.
5. a kind of preparation method of viscose rayon combustion inhibitor special as described in claim 1, which is characterized in that the step
(2) alkali being added in is sodium hydroxide or potassium hydroxide.
6. a kind of preparation method of viscose rayon combustion inhibitor special as described in claim 1, which is characterized in that the step
(3) mass ratio of anhydrous methanol and filter cake is (8-15) in: 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910031534.3A CN109503662A (en) | 2019-01-14 | 2019-01-14 | The preparation method of viscose rayon combustion inhibitor special |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910031534.3A CN109503662A (en) | 2019-01-14 | 2019-01-14 | The preparation method of viscose rayon combustion inhibitor special |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN109503662A true CN109503662A (en) | 2019-03-22 |
Family
ID=65757814
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910031534.3A Pending CN109503662A (en) | 2019-01-14 | 2019-01-14 | The preparation method of viscose rayon combustion inhibitor special |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109503662A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114957334A (en) * | 2021-07-31 | 2022-08-30 | 南通江山农药化工股份有限公司 | Post-treatment process and application of flame retardant product |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101948487A (en) * | 2010-09-09 | 2011-01-19 | 吉林市吉溧化工有限责任公司 | Method for synthesizing dithio dineopentyl phosphate fire retardant |
| CN102186870A (en) * | 2008-10-29 | 2011-09-14 | 隆萨有限公司 | Process for the production of organic dithiopyrophosphates |
| CN108823667A (en) * | 2018-07-16 | 2018-11-16 | 北京赛欧兰阻燃纤维有限公司 | Multielement synergistic flame retardant and the manufacturing process for regenerating flame retardant cellulose fiber |
-
2019
- 2019-01-14 CN CN201910031534.3A patent/CN109503662A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102186870A (en) * | 2008-10-29 | 2011-09-14 | 隆萨有限公司 | Process for the production of organic dithiopyrophosphates |
| CN101948487A (en) * | 2010-09-09 | 2011-01-19 | 吉林市吉溧化工有限责任公司 | Method for synthesizing dithio dineopentyl phosphate fire retardant |
| CN108823667A (en) * | 2018-07-16 | 2018-11-16 | 北京赛欧兰阻燃纤维有限公司 | Multielement synergistic flame retardant and the manufacturing process for regenerating flame retardant cellulose fiber |
Non-Patent Citations (3)
| Title |
|---|
| 任元林: "磷系阻燃剂的合成及阻燃Lyocell纤维的研制", 《中国优秀博硕士学位论文全文数据工程科技Ⅰ辑》 * |
| 张海滨等: "阻燃剂2,2’-二氧[5.5-二甲基-1,3,2-二氧磷杂环]2,2’-二硫化物的合成", 《精细化工中间体》 * |
| 王洋: "有机磷系阻燃剂的合成与应用研究", 《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114957334A (en) * | 2021-07-31 | 2022-08-30 | 南通江山农药化工股份有限公司 | Post-treatment process and application of flame retardant product |
| CN114957334B (en) * | 2021-07-31 | 2024-03-05 | 南通江山农药化工股份有限公司 | Post-treatment process and application of flame retardant product |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101219997A (en) | Synthesis of 2-chlorine-5- amido pyrimidine | |
| CN106349245A (en) | Sitagliptin phosphate impurities, method for preparing same and application of sitagliptin phosphate impurities | |
| CN103626699A (en) | Industrial preparation method of 4,7-dichloroquinoline | |
| CN109503662A (en) | The preparation method of viscose rayon combustion inhibitor special | |
| CN105254575A (en) | Synthetic method for sulfadiazine | |
| CN104529766A (en) | Preparation method of pentaerythritol tristearate | |
| CN103058936B (en) | The preparation method of 4-[(the chloro-2-pyrimidyl of 4-) is amino] cyanophenyl | |
| CN102167667B (en) | Method for synthesizing pentaerythritol tetrabenzoate | |
| CN109678686A (en) | A kind of preparation method of anti-hepatitis drug Lei Dipawei key intermediate | |
| CN105461691B (en) | A kind of preparation method of Azelnidipine | |
| CN104447758A (en) | Synthesis process of pyrazolo[3,4-d]pyrimidine compounds | |
| CN104557752A (en) | Synthetic method of 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione compound | |
| CN103360433B (en) | A kind of method of one kettle way synthesizing trichloro-6-acetic acid esters | |
| CN102408348A (en) | New preparation method of gadobenate dimeglumine | |
| CN103922959A (en) | Method for preparing intermediate diethyl acetamidomalonate through organic synthesis | |
| CN110372709A (en) | A kind of preparation method of Allopurinol crystal | |
| CN103804221A (en) | Preparation method of 4-(4-amino phenyl)-3-morpholone and intermediate of 4-(4-amino phenyl)-3-morpholone | |
| CN110698381A (en) | Method for synthesizing N- (benzyloxycarbonyl) succinimide by one-pot two-phase method | |
| CN106283638B (en) | A kind of weaving bleeding agent and preparation method thereof | |
| CN104402737A (en) | New method for preparing bromhexine hydrochloride | |
| CN100537554C (en) | Docetaxel crystal system and preparation method thereof | |
| CN110172038B (en) | Process for preparing analgin magnesium by one-pot method | |
| JPS58120514A (en) | Manufacture of high purity magnesium hydroxide | |
| CN102336755B (en) | Chemical synthesis method of 6-chloropurine | |
| WO2016034150A1 (en) | Method for preparing bosutinib and crystal 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 | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20190322 |
|
| RJ01 | Rejection of invention patent application after publication |