CN116023244B - Method for treating residue of photoinitiator 184 distillation still - Google Patents
Method for treating residue of photoinitiator 184 distillation still Download PDFInfo
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- CN116023244B CN116023244B CN202211555059.8A CN202211555059A CN116023244B CN 116023244 B CN116023244 B CN 116023244B CN 202211555059 A CN202211555059 A CN 202211555059A CN 116023244 B CN116023244 B CN 116023244B
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- solvent
- distillation
- photoinitiator
- residue
- clear liquid
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- 238000004821 distillation Methods 0.000 title claims abstract description 67
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 title claims abstract description 48
- 238000000034 method Methods 0.000 title claims abstract description 30
- 239000002904 solvent Substances 0.000 claims abstract description 45
- 239000007788 liquid Substances 0.000 claims abstract description 18
- 238000002156 mixing Methods 0.000 claims abstract description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 26
- 239000007787 solid Substances 0.000 claims description 12
- 239000003208 petroleum Substances 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 5
- 239000002244 precipitate Substances 0.000 claims description 4
- 239000012043 crude product Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 239000012141 concentrate Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 239000002198 insoluble material Substances 0.000 claims 1
- 239000012535 impurity Substances 0.000 abstract description 14
- 238000009835 boiling Methods 0.000 abstract description 11
- 239000002994 raw material Substances 0.000 abstract description 4
- 238000004064 recycling Methods 0.000 abstract description 2
- 238000012216 screening Methods 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 15
- 238000011084 recovery Methods 0.000 description 9
- 239000002699 waste material Substances 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for treating the residue of a photoinitiator 184 distillation kettle, which comprises the steps of screening a solvent, dissolving the residue of the distillation kettle by adopting a specific first solvent, adding a specific second solvent into the obtained clear liquid for mixing, separating out impurities to obtain the clear liquid, effectively separating the photoinitiator 184 from high-boiling impurities, and then desolventizing and distilling to obtain a photoinitiator 184 product; the purity of the photoinitiator 184 obtained by the treatment method can reach more than 90%, the mass of the photoinitiator 184 obtained by recycling is high in proportion to the residual mass of the raw material distillation kettle, and the photoinitiator 184 in the distillation kettle residue is effectively recycled.
Description
Technical Field
The invention belongs to the field of photoinitiators, and relates to a method for treating residues of a distillation kettle of a photoinitiator 184.
Background
1-Hydroxy cyclohexyl phenyl ketone, also known as photoinitiator 184, is a free radical type I photoinitiator and is mainly used for initiating the rapid curing of acrylate and methacrylate systems.
CN108911960a discloses a preparation method of photoinitiator 1-hydroxycyclohexyl phenyl ketone, which comprises acylation reaction, friedel-crafts reaction, chlorination reaction and alkaline hydrolysis reaction, to obtain crude photoinitiator, distillation residue is generated in the rectification and purification of the crude photoinitiator, the distillation residue contains photoinitiator 184 and high boiling point impurities, the photoinitiator 184 and the high boiling point impurities are difficult to separate through further distillation or extraction, the traditional process generally does not carry out recovery treatment, and the crude photoinitiator is directly used as dangerous waste disposal, so that the product is wasted.
Therefore, it is still significant to develop a still residue treatment process that can achieve recovery of photoinitiator 184 from the still residue.
Disclosure of Invention
The invention aims to provide a method for treating the residue of a photoinitiator 184 distillation kettle, which comprises the steps of screening a solvent, dissolving the residue of the distillation kettle by adopting a specific first solvent, adding a specific second solvent into the obtained clear liquid for mixing, separating out impurities to obtain the clear liquid, effectively separating the photoinitiator 184 from high-boiling impurities, and then desolventizing and distilling to obtain a photoinitiator 184 product; the purity of the photoinitiator 184 obtained by the treatment method can reach more than 90%, the mass of the photoinitiator 184 obtained by recycling is high in proportion to the residual mass of the raw material distillation kettle, and the photoinitiator 184 in the distillation kettle residue is effectively recycled.
In order to achieve the aim of the invention, the invention adopts the following technical scheme:
the invention provides a method for treating residues of a photoinitiator 184 distillation kettle, which comprises the following steps:
(1) Mixing the residue of the distillation kettle with a first solvent, dissolving, and removing insoluble substances to obtain clear liquid;
(2) Adding a second solvent into the clear liquid obtained in the step (1), mixing, and removing precipitate to obtain clear liquid;
(3) Desolventizing the clear liquid obtained in the step (2) to obtain a concentrated solution;
(4) Distilling the concentrate of step (3) to obtain photoinitiator 184;
Wherein the first solvent is at least one selected from ethyl acetate, acetone, diethyl ether, isopropanol or toluene; the second solvent is selected from at least one of petroleum ether, cyclohexane or n-hexane.
The conventional preparation process of the photoinitiator 184 generally comprises the steps of acylation reaction, friedel-crafts reaction, chlorination reaction and alkaline hydrolysis reaction, wherein an obtained alkaline hydrolysis product is washed to obtain a crude product of the photoinitiator 184, and then distilled to obtain a product of the photoinitiator 184 and residues of a distillation kettle; the distillation still residue contains the photoinitiator 184 and high boiling point impurities, and recovery of the photoinitiator 184 in the distillation still residue is difficult to realize through further distillation; the photoinitiator 184 and high boiling point impurities in the residue of the distillation kettle have solubility in an organic solvent, so that the extraction and separation difficulties are high; the traditional process generally does not carry out recovery treatment, and is directly used as a dangerous waste scrapping treatment, so that the waste of the photoinitiator 184 is caused, and the dangerous waste treatment cost is high; based on solving the above problems, the present invention provides a treatment method of still residue capable of effectively recovering the photoinitiator 184.
The distillation still residue refers to a still residue obtained after distillation of the crude photoinitiator 184.
According to the method, the specific first solvent is adopted to dissolve the residue in the distillation kettle, insoluble impurities are removed through filtration to obtain clear liquid, then the second solvent is added, stirring and mixing are carried out uniformly, high-boiling impurities are separated out in the form of flocculent solids, so that the separation of the photoinitiator 184 and part of high-boiling impurities is realized, clear liquid is obtained through separation, the photoinitiator 184 product can be obtained through desolventizing and distillation, the purity of the obtained photoinitiator 184 product can reach more than 90%, the mass of the recovered photoinitiator 184 accounts for higher proportion of the mass of the residue in the distillation kettle of the raw material, and the effective recovery of the photoinitiator 184 in the distillation kettle residue is realized.
According to the invention, the specific first solvent and the specific second solvent are screened, the first solvent is adopted to dissolve the residue of the distillation kettle, and the second solvent is adopted to separate out part of high-boiling impurities, so that the photoinitiator 184 and the high-boiling impurities are effectively separated, the recovery ratio and the purity of the product are high, and the industrial application requirement is met.
Preferably, the first solvent is ethyl acetate, and the second solvent is petroleum ether.
The treatment method of the invention preferably uses the solvent, which is beneficial to realizing higher recovery ratio and product purity.
Preferably, the still residue is in the form of a black solid.
Preferably, the mass ratio of the still residue to the first solvent in step (1) is from 0.95 to 1.5, e.g. 1, 1.05, 1.1, 1.15, 1.2, 1.25, 1.3, 1.35, 1.4 or 1.45, etc.
Preferably, the insoluble matter of step (1) is a powdery solid.
Preferably, the mass ratio of the second solvent in step (2) to the residue of the distillation still in step (1) is 1.8 to 2.5, for example 1.9, 2.0, 2.1, 2.2, 2.3 or 2.4, etc.
Preferably, the precipitate in step (2) is a flocculent solid.
Preferably, the first solvent and the second solvent are removed by desolventizing in step (3).
Preferably, the mass sum of the first solvent and the second solvent removed in step (3) is 80% to 95%, such as 81%, 82%, 83%, 84%, 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93% or 94%, etc., of the mass sum of the first solvent and the second solvent added in step (1) and step (2).
Preferably, the method of desolventizing in step (3) is atmospheric distillation.
Preferably, the distillation in step (4) is carried out by distillation under reduced pressure.
Compared with the prior art, the invention has the following beneficial effects:
According to the method for treating the distillation still residue of the photoinitiator 184, disclosed by the invention, the distillation still residue is dissolved by adopting a specific first solvent, and a specific second solvent is added in a combined way, so that high-boiling impurities are separated out in the form of flocculent solids, and the photoinitiator 184 is obtained through desolventizing and distillation, the purity of the obtained photoinitiator 184 and the mass of the recovered photoinitiator 184 account for the mass of the raw material distillation still residue, and the effective recovery of the photoinitiator 184 in the distillation still residue is realized.
Detailed Description
The technical scheme of the invention is further described by the following specific embodiments. It will be apparent to those skilled in the art that the examples are merely to aid in understanding the invention and are not to be construed as a specific limitation thereof.
Example 1
The embodiment provides a method for treating residues of a distillation kettle of a photoinitiator 184, which specifically comprises the following steps:
(1) Dissolving: 127.5g of black solid 184 distillation still residue and 122g of ethyl acetate are added into a four-mouth bottle, uniformly stirred, stood still, a small amount of powdery solid exists at the bottom, and supernatant liquid is poured out;
(2) Precipitation of residues: adding 275g of petroleum ether slowly into the clear liquid in the step (1) under stirring, and pouring out the supernatant after uniformly stirring the flocculent solid in the clear liquid along with the addition of the petroleum ether;
(3) Concentrating: distilling the clear liquid obtained in the step (2) under normal pressure to distill out 350.3g of mixed solution of ethyl acetate and petroleum ether, and obtaining 97g of concentrated solution at the moment;
(4) And (3) distilling: and (3) carrying out reduced pressure distillation on the concentrated solution obtained in the step (3), and collecting fractions with the temperature range of 150-160 ℃ to obtain 54.3g of distilled product (the content of 184 detected by GC: 91.8 percent) and 33.9g of distillation residue.
The black solid 184 stills residue in this example resulted from the following procedure including: 300g of the crude product of the alkaline hydrolysis of the photoinitiator 184 is added into a four-mouth bottle, reduced pressure distillation is carried out, fractions with the temperature ranging from 150 ℃ to 160 ℃ are collected under the condition of 2mmHg of vacuum degree, the distillation is finished, 15.2g of distillation still residues are remained in the distillation bottle, and the operation is repeated, so that the required distillation still residues in the above examples are obtained.
Example 2
The present example differs from example 1 only in that the mass of ethyl acetate etc. in step (1) is replaced by acetone; other parameters and conditions were exactly the same as in example 1;
the distillation under reduced pressure in step (4) of the present example gave 50.1g of a distilled product (GC-detected 184 content: 90.6%) and 41.2g of a distillation residue.
Example 3
The present example differs from example 1 only in that the mass of ethyl acetate and the like in step (1) is replaced with isopropyl alcohol; other parameters and conditions were exactly the same as in example 1;
The distillation under reduced pressure in step (4) of the present example gave 53.4g of a distilled product (content: 91.3% by GC analysis 184), and 32.2g of a distillation residue.
Example 4
This example differs from example 1 only in that the mass of ethyl acetate and the like in step (1) is replaced with toluene; other parameters and conditions were exactly the same as in example 1;
The distillation under reduced pressure in the step (4) of the present example gave 49.2g of a distilled product (GC-detected 184 content: 90.5%), and 30.2g of a distillation residue.
Example 5
The present example differs from example 1 only in that the petroleum ether and other mass in step (2) is replaced with cyclohexane; other parameters and conditions were exactly the same as in example 1;
The distillation under reduced pressure in step (4) of the present example gave 53.7g of a distilled product (content: 91.2% by GC analysis 184), and 35.1g of a distillation residue.
Example 6
The present example differs from example 1 only in that the petroleum ether and other mass in step (2) is replaced with n-hexane; other parameters and conditions were exactly the same as in example 1;
The distillation under reduced pressure in step (4) of the present example gave 55.2g of a distilled product (content: 91.3% by GC analysis 184), and 32.8g of a distillation residue.
As can be seen from the above examples, the photoinitiator 184 in the still residue can be effectively recovered by the method of the present invention, and the treatment pressure of the still residue can be reduced; meanwhile, as can be seen from the effects of comparative examples 1 to 6, when the solvent in the step (1) is ethyl acetate and the solvent in the step (2) is petroleum ether, the recovery effect of the photoinitiator 184 is better, and the purity of the obtained product is higher.
The applicant declares that the above is only a specific embodiment of the present invention, but the scope of the present invention is not limited thereto, and it should be apparent to those skilled in the art that any changes or substitutions that are easily conceivable within the technical scope of the present invention disclosed by the present invention fall within the scope of the present invention and the disclosure.
Claims (11)
1. A method for treating a residue of a distillation still of a photoinitiator 184, comprising the steps of:
(1) Mixing the residue of the distillation kettle with a first solvent, dissolving, and removing insoluble substances to obtain clear liquid;
(2) Adding a second solvent into the clear liquid obtained in the step (1), mixing, and removing precipitate to obtain clear liquid;
(3) Desolventizing the clear liquid obtained in the step (2) to obtain a concentrated solution;
(4) Distilling the concentrate of step (3) to obtain photoinitiator 184;
Wherein the first solvent is at least one selected from ethyl acetate, acetone, diethyl ether, isopropanol or toluene; the second solvent is selected from at least one of petroleum ether, cyclohexane or n-hexane;
The distillation still residue is obtained by a preparation method comprising the following steps:
and (3) performing reduced pressure distillation on the crude product of the alkaline hydrolysis of the photoinitiator 184, and collecting fractions with the temperature of 150-160 ℃ under the vacuum condition, wherein the distillation is finished, so as to obtain the residue of the distillation kettle.
2. The process of claim 1, wherein the first solvent is ethyl acetate and the second solvent is petroleum ether.
3. The process of claim 1 wherein the still residue is in the form of a black solid.
4. The process according to claim 1, wherein the mass ratio of the residue of the distillation still to the first solvent in the step (1) is 0.95 to 1.5.
5. The process of claim 1 wherein the insoluble material of step (1) is a powdered solid.
6. The process according to claim 1, wherein the mass ratio of the second solvent in the step (2) to the residue of the distillation still in the step (1) is 1.8 to 2.5.
7. The process of claim 1, wherein the precipitate in step (2) is a flocculent solid.
8. The process of claim 1, wherein the first solvent and the second solvent are removed by desolventizing in step (3).
9. The process of claim 8, wherein the total mass of the first solvent and the second solvent removed in step (3) is 80% to 95% of the total mass of the first solvent and the second solvent added in step (1) and step (2).
10. The process of claim 1, wherein the desolventizing in step (3) is performed by atmospheric distillation.
11. The process according to claim 1, wherein the distillation in step (4) is a reduced pressure distillation.
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Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN109467250A (en) * | 2018-12-28 | 2019-03-15 | 湖南久日新材料有限公司 | A kind of 1173 and 184 technique waste water administering method of photoinitiator |
CN109503343A (en) * | 2018-12-28 | 2019-03-22 | 常州久日化学有限公司 | A kind of preparation method of photoinitiator 184 |
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JP4099950B2 (en) * | 2001-02-05 | 2008-06-11 | 東亞合成株式会社 | Method for producing cyclohexyl (meth) acrylate |
KR101282799B1 (en) * | 2012-06-08 | 2013-07-04 | 주식회사 코원이노텍 | Refining method of organic solvent to recycle pma |
CN112876357A (en) * | 2021-01-20 | 2021-06-01 | 江苏福昌环保科技集团有限公司 | Production process for producing plasticizer from PTA oxidation residues |
CN114835569B (en) * | 2022-04-20 | 2023-12-29 | 宁夏沃凯珑新材料有限公司 | Method for producing photoinitiator UV-184 by condensation method |
CN115141162B (en) * | 2022-09-05 | 2022-12-20 | 天津久日新材料股份有限公司 | Preparation method of photoinitiator and product thereof |
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CN109467250A (en) * | 2018-12-28 | 2019-03-15 | 湖南久日新材料有限公司 | A kind of 1173 and 184 technique waste water administering method of photoinitiator |
CN109503343A (en) * | 2018-12-28 | 2019-03-22 | 常州久日化学有限公司 | A kind of preparation method of photoinitiator 184 |
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