CN102432635A - Method for preparing light stabilizer hexaethyl phosphoric triamide - Google Patents
Method for preparing light stabilizer hexaethyl phosphoric triamide Download PDFInfo
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- CN102432635A CN102432635A CN201110324664XA CN201110324664A CN102432635A CN 102432635 A CN102432635 A CN 102432635A CN 201110324664X A CN201110324664X A CN 201110324664XA CN 201110324664 A CN201110324664 A CN 201110324664A CN 102432635 A CN102432635 A CN 102432635A
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- CN
- China
- Prior art keywords
- hexaethyl
- diethylamine
- phosphoryl triamide
- alkali
- solvent
- 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.)
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- 238000000034 method Methods 0.000 title abstract description 10
- ROZPNEGZBIUWBX-UHFFFAOYSA-N n-[bis(diethylamino)phosphoryl]-n-ethylethanamine Chemical compound CCN(CC)P(=O)(N(CC)CC)N(CC)CC ROZPNEGZBIUWBX-UHFFFAOYSA-N 0.000 title abstract 4
- 239000004611 light stabiliser Substances 0.000 title abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims abstract description 26
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000003513 alkali Substances 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 16
- 230000035484 reaction time Effects 0.000 claims abstract description 11
- 239000002994 raw material Substances 0.000 claims abstract description 5
- DMSZORWOGDLWGN-UHFFFAOYSA-N ctk1a3526 Chemical compound NP(N)(N)=O DMSZORWOGDLWGN-UHFFFAOYSA-N 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 238000004821 distillation Methods 0.000 claims description 16
- 229910019213 POCl3 Inorganic materials 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 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 8
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 claims description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical group Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 8
- CBPYOHALYYGNOE-UHFFFAOYSA-M potassium;3,5-dinitrobenzoate Chemical compound [K+].[O-]C(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 CBPYOHALYYGNOE-UHFFFAOYSA-M 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- 238000006482 condensation reaction Methods 0.000 claims description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 229960001701 chloroform Drugs 0.000 claims description 4
- 235000017550 sodium carbonate Nutrition 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 3
- 235000015320 potassium carbonate Nutrition 0.000 claims description 3
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 3
- 239000011592 zinc chloride Substances 0.000 claims description 3
- 235000005074 zinc chloride Nutrition 0.000 claims description 3
- 238000005265 energy consumption Methods 0.000 abstract description 2
- 238000003912 environmental pollution Methods 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 238000000746 purification Methods 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 238000010992 reflux Methods 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- -1 methane amide Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Abstract
The invention discloses a method for preparing a light stabilizer hexaethyl phosphoric triamide. According to the method, phosphorus oxychloride, diethylamine and alkali are taken as raw materials and react in the presence of a catalyst and a solvent to prepare the hexaethyl phosphoric triamide. In the hexaethyl phosphoric triamide synthesized by using the method, the separation and purification process is simple, the reaction time is short, the yield of products reaches over 92 percent, the purity of the products is higher, and the method is low in energy consumption, low in environmental pollution and low in cost, and is a more ideal process to realize industrialized production.
Description
Technical field
The present invention relates to a kind of preparation method of photostabilizer Hexaethyl phosphoryl triamide.
Background technology
The Hexaethyl phosphoryl triamide is the remarkable high boiling point of a kind of performance, strong polar organic solvent, is again a kind of extremely valuable chemical reaction medium with catalytic performance, aspect high polymer synthesis industry, important application is arranged; Also can be used as the photostabilizer of SE, polyvinylidene dichloride, methane amide, urethane etc.; When being used for the SE plastic sheeting for farm use, normal and other photostabilizers are used, and the weathering resistance and the winter hardiness of its film improve greatly; The processing temperature that contains the film of Hexaethyl phosphoryl triamide can reduce processing temperature; Help material and in the course of processing, keep stable performance, be difficult for decomposing, its molecular formula is C
12H
10N
3PO, molecular weight are 263.25, molecular structural formula:
Its outward appearance is an oily liquids, and the prior synthesizing method of Hexaethyl phosphoryl triamide is Hexaethyl phosphamidon and exsiccant oxygen direct oxidation method, and this method technology is simple, but product yield is very low, should not adopt in the industry.This research is to be catalyzer with the acid halide, in the organic solvent system of alkalescence, is the synthetic Hexaethyl phosphoryl triamide of raw material by diethylamine and POCl3, and result of study shows that experiment condition is gentle, and the reaction times is short, and is easy and simple to handle, good product quality.
Summary of the invention
The objective of the invention is provides the preparation method of the high Hexaethyl phosphoryl triamide of a kind of product yield in order to overcome above deficiency.
The present invention realizes through following technical scheme: a kind of preparation method of photostabilizer Hexaethyl phosphoryl triamide; Be to be raw material with POCl3, diethylamine, alkali, under the condition that catalyzer and solvent exist, carry out condensation reaction, the usage ratio of said POCl3, diethylamine, alkali, catalyzer and solvent is counted 1:1.53 ~ 3.82:1.04 ~ 1.81:0.12 ~ 1.32:1.96 ~ 4.57 by quality; The temperature of condensation reaction is 10-20 ℃; Reaction times is 5-10h, and stopped reaction is chilled to room temperature; Filter out sodium-chlor and diethylamine hydrochloride; Air distillation removes and desolvates and diethylamine, and then carries out the cut that underpressure distillation is collected, and is Hexaethyl phosphoryl triamide product.
Further improvement of the present invention is: said alkali is yellow soda ash or salt of wormwood or sodium hydroxide or Pottasium Hydroxide.
Further improvement of the present invention is: said catalyzer is aluminum chloride or iron trichloride or zinc dichloride.
Further improvement of the present invention is: said solvent is methylene dichloride or trichloromethane or benzene or toluene.
The present invention compared with prior art has the following advantages: the present invention synthesizes the Hexaethyl phosphoryl triamide, and it is simple to separate purification process, and the reaction times is short; Product yield reaches more than 92%, and product purity is higher, less energy consumption; Environmental pollution is little, and cost is low, is the comparatively ideal technology that realizes suitability for industrialized production.
Embodiment:
In order to deepen to understanding of the present invention, will combine embodiment that the present invention is made further detailed description below, following examples only are used to explain the present invention, do not constitute the qualification to protection domain of the present invention.
The present invention shows a kind of preparing method's of photostabilizer Hexaethyl phosphoryl triamide embodiment, is to be raw material with POCl3, diethylamine, alkali, under the condition that catalyzer and solvent exist, carries out condensation reaction; The usage ratio of said POCl3, diethylamine, alkali, catalyzer and solvent is counted 1:1.53 ~ 3.82:1.04 ~ 1.81:0.12 ~ 1.32:1.96 ~ 4.57 by quality, and the temperature of condensation reaction is 10-20 ℃, and the reaction times is 5-10h; Stopped reaction is chilled to room temperature, filters out sodium-chlor and diethylamine hydrochloride; Air distillation removes and desolvates and diethylamine, and then carries out the cut that underpressure distillation is collected, and is Hexaethyl phosphoryl triamide product; Alkali is yellow soda ash or salt of wormwood or sodium hydroxide or Pottasium Hydroxide; The preferred yellow soda ash of alkali of the present invention, catalyzer are aluminum chloride or iron trichloride or zinc dichloride, the preferred aluminum chloride of catalyzer of the present invention; Solvent is methylene dichloride or trichloromethane or benzene or toluene, the preferred trichloromethane of solvent of the present invention.
Embodiment 1:
In the four-hole reaction flask of electric mixer, reflux exchanger and TM is housed, add POCl3 15.3g successively, diethylamine 26.4g, alkali 16.4g, catalyzer 6g; Solvent 50g, agitator is in the time of controlled temperature 10-20 ℃; Controlling reaction time 5-10h, behind the stopped reaction, stopped reaction; Be chilled to room temperature, filter out sodium-chlor and diethylamine hydrochloride, air distillation removes and desolvates and diethylamine; And then carry out the cut that underpressure distillation is collected, and being Hexaethyl phosphoryl triamide product, Hexaethyl phosphoryl triamide product yield reaches 92.34%.
Embodiment 2:
In the four-hole reaction flask of electric mixer, reflux exchanger and TM is housed, add POCl3 15.3g successively, diethylamine 29.3g, alkali 16.4g, catalyzer 6g; Solvent 50g, agitator is in the time of controlled temperature 10-20 ℃; Controlling reaction time 5-10h, behind the stopped reaction, stopped reaction; Be chilled to room temperature, filter out sodium-chlor and diethylamine hydrochloride, air distillation removes and desolvates and diethylamine; And then carry out the cut that underpressure distillation is collected, and being Hexaethyl phosphoryl triamide product, Hexaethyl phosphoryl triamide product yield reaches 93.12%.
Embodiment 3:
In the four-hole reaction flask of electric mixer, reflux exchanger and TM is housed, add POCl3 15.3g successively, diethylamine 43.9g, alkali 16.4g, catalyzer 8g; Solvent 50g, agitator is in the time of controlled temperature 10-20 ℃; Controlling reaction time 5-10h, behind the stopped reaction, stopped reaction; Be chilled to room temperature, filter out sodium-chlor and diethylamine hydrochloride, air distillation removes and desolvates and diethylamine; And then carry out the cut that underpressure distillation is collected, and being Hexaethyl phosphoryl triamide product, Hexaethyl phosphoryl triamide product yield reaches 92.76%.
Embodiment 4:
In the four-hole reaction flask of electric mixer, reflux exchanger and TM is housed, add POCl3 15.3g successively, diethylamine 29.3g, alkali 16.9g, catalyzer 10g; Solvent 50g, agitator is in the time of controlled temperature 10-20 ℃; Controlling reaction time 5-10h, behind the stopped reaction, stopped reaction; Be chilled to room temperature, filter out sodium-chlor and diethylamine hydrochloride, air distillation removes and desolvates and diethylamine; And then carry out the cut that underpressure distillation is collected, and being Hexaethyl phosphoryl triamide product, Hexaethyl phosphoryl triamide product yield reaches 93.51%.
Embodiment 5:
In the four-hole reaction flask of electric mixer, reflux exchanger and TM is housed, add POCl3 15.3g successively, diethylamine 32.9g, alkali 15.9g, catalyzer 15g; Solvent 70g, agitator is in the time of controlled temperature 10-20 ℃; Controlling reaction time 5-10h, behind the stopped reaction, stopped reaction; Be chilled to room temperature, filter out sodium-chlor and diethylamine hydrochloride, air distillation removes and desolvates and diethylamine; And then carry out the cut that underpressure distillation is collected, and being Hexaethyl phosphoryl triamide product, Hexaethyl phosphoryl triamide product yield reaches 93.97%.
Claims (4)
1. the preparation method of a photostabilizer Hexaethyl phosphoryl triamide is characterized in that: be to be raw material with POCl3, diethylamine, alkali, under the condition that catalyzer and solvent exist, carry out condensation reaction; The usage ratio of said POCl3, diethylamine, alkali, catalyzer and solvent is counted 1:1.53 ~ 3.82:1.04 ~ 1.81:0.12 ~ 1.32:1.96 ~ 4.57 by quality, and the temperature of condensation reaction is 10-20 ℃, and the reaction times is 5-10h; Stopped reaction; Be chilled to room temperature, filter out sodium-chlor and diethylamine hydrochloride, air distillation removes and desolvates and diethylamine; And then carry out the cut that underpressure distillation is collected, be Hexaethyl phosphoryl triamide product.
2. according to the preparation method of the said photostabilizer Hexaethyl of claim 1 phosphoryl triamide, it is characterized in that: said alkali is yellow soda ash or salt of wormwood or sodium hydroxide or Pottasium Hydroxide.
3. according to the preparation method of the said photostabilizer Hexaethyl of claim 1 phosphoryl triamide, it is characterized in that: said catalyzer is aluminum chloride or iron trichloride or zinc dichloride.
4. according to the preparation method of the said photostabilizer Hexaethyl of claim 1 phosphoryl triamide, it is characterized in that: said solvent is methylene dichloride or trichloromethane or benzene or toluene.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110324664.XA CN102432635B (en) | 2011-10-24 | 2011-10-24 | Method for preparing light stabilizer hexaethyl phosphoric triamide |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110324664.XA CN102432635B (en) | 2011-10-24 | 2011-10-24 | Method for preparing light stabilizer hexaethyl phosphoric triamide |
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| Publication Number | Publication Date |
|---|---|
| CN102432635A true CN102432635A (en) | 2012-05-02 |
| CN102432635B CN102432635B (en) | 2015-03-11 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN201110324664.XA Active CN102432635B (en) | 2011-10-24 | 2011-10-24 | Method for preparing light stabilizer hexaethyl phosphoric triamide |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104844804A (en) * | 2015-03-25 | 2015-08-19 | 沈阳化工大学 | Polymer type phosphorus-nitrogen intumescent flame retardant and preparation method therefor |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2752392A (en) * | 1952-04-11 | 1956-06-26 | Monsanto Chemicals | Manufacture of phosphorus amides |
| US3991110A (en) * | 1972-12-29 | 1976-11-09 | E. I. Du Pont De Nemours And Company | Preparation of hexamethylphosphoramide |
-
2011
- 2011-10-24 CN CN201110324664.XA patent/CN102432635B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2752392A (en) * | 1952-04-11 | 1956-06-26 | Monsanto Chemicals | Manufacture of phosphorus amides |
| US3991110A (en) * | 1972-12-29 | 1976-11-09 | E. I. Du Pont De Nemours And Company | Preparation of hexamethylphosphoramide |
Non-Patent Citations (2)
| Title |
|---|
| 《Russian Journal of General Chemistry》 20021231 L. K. Sal'keeva et al. Reactions of Phosphorodiamidous Acid Esters with alpha-Halocarbonyl Compounds 第1760-1763页 1-4 第72卷, 第11期 * |
| L. K. SAL’KEEVA ET AL.: "Reactions of Phosphorodiamidous Acid Esters with α-Halocarbonyl Compounds", 《RUSSIAN JOURNAL OF GENERAL CHEMISTRY》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104844804A (en) * | 2015-03-25 | 2015-08-19 | 沈阳化工大学 | Polymer type phosphorus-nitrogen intumescent flame retardant and preparation method therefor |
| CN104844804B (en) * | 2015-03-25 | 2017-05-24 | 沈阳化工大学 | Polymer type phosphorus-nitrogen intumescent flame retardant and preparation method therefor |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102432635B (en) | 2015-03-11 |
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