CN105294457B - A kind of method that use freezing and crystallizing, decolouring, high vacuum rectification technique refine low-purity amino-glycerol - Google Patents
A kind of method that use freezing and crystallizing, decolouring, high vacuum rectification technique refine low-purity amino-glycerol Download PDFInfo
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- CN105294457B CN105294457B CN201510667225.7A CN201510667225A CN105294457B CN 105294457 B CN105294457 B CN 105294457B CN 201510667225 A CN201510667225 A CN 201510667225A CN 105294457 B CN105294457 B CN 105294457B
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- MQDLKAADJTYKRH-UHFFFAOYSA-N 1-aminopropane-1,2,3-triol Chemical compound NC(O)C(O)CO MQDLKAADJTYKRH-UHFFFAOYSA-N 0.000 title claims abstract description 48
- 238000000034 method Methods 0.000 title claims abstract description 22
- 230000008014 freezing Effects 0.000 title claims abstract description 6
- 238000007710 freezing Methods 0.000 title claims abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 36
- 238000002425 crystallisation Methods 0.000 claims abstract description 20
- 230000008025 crystallization Effects 0.000 claims abstract description 20
- 239000012267 brine Substances 0.000 claims abstract description 19
- 230000008676 import Effects 0.000 claims abstract description 19
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims abstract description 19
- 239000000463 material Substances 0.000 claims abstract description 14
- 238000003756 stirring Methods 0.000 claims abstract description 12
- 238000010438 heat treatment Methods 0.000 claims abstract description 6
- 239000007788 liquid Substances 0.000 claims description 10
- 239000003039 volatile agent Substances 0.000 claims description 9
- 235000009508 confectionery Nutrition 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 238000010025 steaming Methods 0.000 claims 1
- 238000004821 distillation Methods 0.000 abstract description 10
- 239000012071 phase Substances 0.000 description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 230000002950 deficient Effects 0.000 description 6
- 238000007670 refining Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 3
- 230000006835 compression Effects 0.000 description 3
- 238000007906 compression Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 229960001025 iohexol Drugs 0.000 description 3
- NTHXOOBQLCIOLC-UHFFFAOYSA-N iohexol Chemical compound OCC(O)CN(C(=O)C)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I NTHXOOBQLCIOLC-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical class OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 206010067484 Adverse reaction Diseases 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- AMDBBAQNWSUWGN-UHFFFAOYSA-N Ioversol Chemical compound OCCN(C(=O)CO)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I AMDBBAQNWSUWGN-UHFFFAOYSA-N 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 230000006838 adverse reaction Effects 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000001741 anti-phlogistic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000002872 contrast media Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 229960004359 iodixanol Drugs 0.000 description 1
- NBQNWMBBSKPBAY-UHFFFAOYSA-N iodixanol Chemical compound IC=1C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C(I)C=1N(C(=O)C)CC(O)CN(C(C)=O)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I NBQNWMBBSKPBAY-UHFFFAOYSA-N 0.000 description 1
- 229960004537 ioversol Drugs 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003690 nonionic contrast media Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 238000004227 thermal cracking Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of method that use freezing and crystallizing, decolouring, high vacuum rectification technique refine low-purity amino-glycerol, comprise the following steps：A, by 120Kg amino-glycerols pass through unqualified amino-glycerol import add crystallization kettle in, the chilled brine that temperature is 5 10 DEG C is passed through by cool brine import, after 80 minutes, the compressed air that pressure is 0.25MPa is passed through into crystallization kettle, material is pressed into the first accurate filter；Enter back into decolouring kettle；B, to decolouring kettle add 180Kg ethanol, vapour heating is opened in stirring after 40 minutes, kettle temperature is risen to 55 DEG C after 30 minutes, 7.2Kg activated carbons, 4.8Kg atlapulgites are pressed into decolouring kettle by the compressed air for being 0.25MPa with pressure, then continue to stir 60 minutes at a temperature of 55 DEG C；Material in decolouring kettle is pressed into the second accurate filter and enters back into finished product distillation still by C, the compressed air for being 0.25MPa with pressure, first steams ethanol, ethanol is continuing with.
Description
It is 2014101118636 the present invention be directed to number of patent application, patent name is a kind of refined dress of amino-glycerol
Put and its purifying technique divisional application.
Technical field is the present invention relates to a kind of process for refining of amino-glycerol, and specifically, being related to one kind can be by purity
Low, outward appearance improves that a kind of impurity content of the purity up to more than 99.7% be high, band color with the high amino-glycerol of color, impurity content
Amino-glycerol purify high-purity certified products production method, belong to chemical technology field.
Background technology
Amino-glycerol（3- amino -1,2-PD）It is the structure list for producing non-ionic contrast medium iodinated X-ray contrast agent
Member, for synthesizing Iohexol, Ioversol and Iodixanol etc., also serves as antiphlogistic, anodyne, cosmetics, some synthetic materials
Deng important intermediate.To reduce the side effect produced to patient to greatest extent, adverse reaction is reduced, it is desirable to amino-glycerol purity
It cannot be below 99.5%（GC）, control inorganic salt content.
At present, the initiation material of amino-glycerol be substantially glycerin chlorohydrin or glycidol directly with ammonia reaction etc., due to
The many-side reason such as technology, raw material, operation, the most purity of domestic industry product is 99% or so, and product is not with
Same color, color is divided into yellow, brown, red, brown color, causes product to cannot be used for Iohexol synthesis at all.It is existing
Amino-glycerol purification technique mainly has：
1st, amino-glycerol defective work through overregulate pH, dehydration, solvent dissolving, decolourize, filtering, remove solvent, decompression steam
The step such as evaporate and obtain purity close to 99.5% product；
2nd, it is column chromatography eluting.Dissolved with low polar elution agent and chromatogram top end is added after amino-glycerol defective work,
Exit detects, to certain index after highly polar eluant, eluent added chromatogram top end and detected, distillation contains amino-glycerol
Eluent obtains finished product.
Method 2 has that cumbersome, product cost is high, the low problem of product purity；Method 2 has laboratory operation value,
There is big Industrialized processing technique difficulty, adsorbent cost height and be difficult the problems such as reuse.Except from amino-glycerol
Product band color, finished product purity are solved on synthesis technique low outer, product is adapted to Iohexol substandard product progress processing and close
Equally there are important economic implications and realistic meaning into this research.
The content of the invention
The invention solves the problems that local problems be in order to overcome the product of amino-glycerol industry generally existing in yellow, brown,
Red, brown color, yellowish-brown or it is faint yellow etc. color, amount of impurities are more, impurity content is high, the low defect of product purity there is provided
A kind of method that use freezing and crystallizing, decolouring, high vacuum rectification technique refine low-purity amino-glycerol.
In order to solve the above problems, the present invention uses following technical scheme：
A kind of method that use freezing and crystallizing, decolouring, high vacuum rectification technique refine low-purity amino-glycerol, including it is following
Step：A, by 120Kg amino-glycerols by unqualified amino-glycerol import add crystallization kettle in, temperature is passed through by cool brine import
The chilled brine for -5--10 DEG C is spent, after 80 minutes, the compressed air that pressure is 0.25MPa is passed through into crystallization kettle, by material
It is pressed into the first accurate filter；Enter back into decolouring kettle；
B, to decolouring kettle add 180Kg ethanol, stirring 40 minutes after open vapour heating, kettle temperature is risen to 55 DEG C after 30 minutes,
7.2Kg activated carbons, 4.8Kg atlapulgites are pressed into decolouring kettle by the compressed air for being 0.25MPa with pressure, then in 55 DEG C of temperature
It is lower to continue to stir 60 minutes；
Material in decolouring kettle is pressed into the second accurate filter and entered back into by C, the compressed air for being 0.25MPa with pressure
Product distillation still, first steams ethanol, and ethanol is continuing with；
D, when gas phase temperature is more than 80 DEG C, open Roots vacuum system, treat finished pot vacuum up to 0.0998MPa and steady
When fixed, gas phase temperature is less than 124 DEG C, condensate liquid is front-end volatiles；The condensate liquid of 124-135 DEG C of gas phase temperature is finished product, finished product ammonia
The purity of base glycerol reaches 99.80%, GC.
The following is the further improvement to above-mentioned technical proposal：
The unqualified amino-glycerol content 94.33%, GC.
The present invention uses such scheme, with advantages below：
1st, using crystallization kettle refrigerating process, by homologue 2- amino-1,3-propanediols, polyglycerine（Generally glycerine
Dimer is to hexamer）Separated out from product, greatly reduce the content of 2- amino-1,3-propanediols in finished product；
2nd, acted synergistically using activated carbon, atlapulgite, pass through the pigment of the unqualified amino-glycerol product of adsorbing and removing, effect
Fruit is substantially, especially particularly evident in removal effects such as buff, yellowish-brown, reddish yellow to defective work；
3rd, distilled using the multi-stage roots vacuum pump set of high vacuum, distillation time is short, and liquidus temperature is low, liquid phase material
Thermal cracking, polymerisation are reduced, while gas phase temperature is low, evaporation rate fast, finished product amino-glycerol yield brings up to more than 60%,
Purity is more than 99.7%；It is glycerin chlorohydrin in product, double（2,3- dihydroxypropyls）Amine, uncle（2,3- dihydroxypropyls）Amine content shows
Write and reduce.
The invention will be further described with reference to the accompanying drawings and examples.
Brief description of the drawings
Accompanying drawing 1 be the embodiment of the present invention in amino-glycerol refining plant figure.
In figure：1- crystallization kettles；The accurate filters of 2- first；3- decolouring kettles；The accurate filters of 4- second；5- finished products distill
Kettle；6- condensers；7- front-end volatiles tanks；8- finished pots；9- Roots vacuum systems；10- cool brines are exported；11- cool brine imports；
The unqualified amino-glycerol imports of 12-.
6th, embodiment：
Embodiment 1, the defective work of processing, amino-glycerol content 95.23% (GC), outward appearance is faint yellow.
As shown in figure 1, a kind of refining plant of amino-glycerol, including pass sequentially through the essence of crystallization kettle 1, first of pipeline connection
Close filter 2, decolouring kettle 3, the second accurate filter 4, finished product distillation still 5, condenser 6, front-end volatiles tank 7 and finished pot 8 and
Roots vacuum system 9；The crystallization kettle 1 is provided with cool brine outlet 10, cool brine import 11 and unqualified amino-glycerol import
12。
The purifying technique of above-mentioned amino-glycerol comprises the following steps：
A, 100Kg amino-glycerols are added in crystallization kettle 1 by unqualified amino-glycerol import 12, pass through cool brine import
11 are passed through the chilled brine that temperature is -5--10 DEG C, after 60 minutes, the compression that pressure is 0.2MPa are passed through into crystallization kettle 1 empty
Gas, the first accurate filter 2 is pressed into by material；Enter back into decolouring kettle 3；
B, to decolouring kettle 3 add 150Kg ethanol, stirring 30 minutes after open vapour heating, kettle temperature is risen to 50 DEG C after 25 minutes,
3Kg activated carbons, 2.5Kg atlapulgites are pressed into decolouring kettle 3 by the compressed air for being 0.25MPa with pressure, then in 55 DEG C of temperature
It is lower to continue to stir 45 minutes；
Material in decolouring kettle 3 is pressed into the second accurate filter 4 and entered back into by C, the compressed air for being 0.25MPa with pressure
Finished product distillation still 5, first steams ethanol, and ethanol is continuing with；
D, when gas phase temperature is more than 80 DEG C, open Roots vacuum system 9, treat the vacuum of finished pot 8 up to 0.0996MPa and
When stable, gas phase temperature is less than 124 DEG C, condensate liquid is front-end volatiles；The condensate liquid of 124-135 DEG C of gas phase temperature is finished product.
The product quality indicator of preparation is shown in Table 1.
The product quality analysis result of table 1
Embodiment 2, the defective work of processing, amino-glycerol content 96.69% (GC), outward appearance is yellowish-brown.
As shown in figure 1, a kind of refining plant of amino-glycerol, including pass sequentially through the essence of crystallization kettle 1, first of pipeline connection
Close filter 2, decolouring kettle 3, the second accurate filter 4, finished product distillation still 5, condenser 6, front-end volatiles tank 7 and finished pot 8 and
Roots vacuum system；The crystallization kettle 1 is provided with cool brine outlet 10, cool brine import 11 and unqualified amino-glycerol import
12。
The purifying technique of above-mentioned amino-glycerol comprises the following steps：
A, 80Kg amino-glycerols are added in crystallization kettle 1 by unqualified amino-glycerol import 12, pass through cool brine import
11 are passed through the chilled brine that temperature is -5--10 DEG C, after 70 minutes, the compression that pressure is 0.2MPa are passed through into crystallization kettle 1 empty
Gas, the first accurate filter 2 is pressed into by material；Enter back into decolouring kettle 3；
B, to decolouring kettle 3 add 140Kg ethanol, stirring 40 minutes after open vapour heating, kettle temperature is risen to 50 DEG C after 30 minutes,
5.6Kg activated carbons, 3.8Kg atlapulgites are pressed into decolouring kettle 3 by the compressed air for being 0.25MPa with pressure, then in 50 DEG C of temperature
Degree is lower to be continued to stir 60 minutes；
Material in decolouring kettle 3 is pressed into the second accurate filter 4 and entered back into by C, the compressed air for being 0.25MPa with pressure
Finished product distillation still 5, first steams ethanol, and ethanol is continuing with；
D, when gas phase temperature is more than 80 DEG C, open Roots vacuum system 9, treat the vacuum of finished pot 8 up to 0.0998MPa and
When stable, gas phase temperature is less than 124 DEG C, condensate liquid is front-end volatiles；The condensate liquid of 124-135 DEG C of gas phase temperature is finished product.
The product quality indicator of preparation is shown in Table 2.
The product quality analysis result of table 2
Embodiment 3, the defective work of processing, amino-glycerol content 94.33% (GC), outward appearance is brown color.
As shown in figure 1, a kind of refining plant of amino-glycerol, including pass sequentially through the essence of crystallization kettle 1, first of pipeline connection
Close filter 2, decolouring kettle 3, the second accurate filter 4, finished product distillation still 5, condenser 6, front-end volatiles tank 7 and finished pot 8 and
Roots vacuum system；The crystallization kettle 1 is provided with cool brine outlet 10, cool brine import 11 and unqualified amino-glycerol import
12。
The purifying technique of above-mentioned amino-glycerol comprises the following steps：
A, 120Kg amino-glycerols are added in crystallization kettle 1 by unqualified amino-glycerol import 12, pass through cool brine import
11 are passed through the chilled brine that temperature is -5--10 DEG C, after 80 minutes, the compression that pressure is 0.25MPa are passed through into crystallization kettle 1 empty
Gas, the first accurate filter 2 is pressed into by material；Enter back into decolouring kettle 3；
B, to decolouring kettle 3 add 180Kg ethanol, stirring 40 minutes after open vapour heating, kettle temperature is risen to 55 DEG C after 30 minutes,
7.2Kg activated carbons, 4.8Kg atlapulgites are pressed into decolouring kettle 3 by the compressed air for being 0.25MPa with pressure, then in 55 DEG C of temperature
Degree is lower to be continued to stir 60 minutes；
Material in decolouring kettle 3 is pressed into the second accurate filter 4 and entered back into by C, the compressed air for being 0.25MPa with pressure
Finished product distillation still 5, first steams ethanol, and ethanol is continuing with；
D, when gas phase temperature is more than 80 DEG C, open Roots vacuum system 9, treat the vacuum of finished pot 8 up to 0.0998MPa and
When stable, gas phase temperature is less than 124 DEG C, condensate liquid is front-end volatiles；The condensate liquid of 124-135 DEG C of gas phase temperature is finished product.
The product quality indicator of preparation is shown in Table 3.
The product quality analysis result of table 3
Claims (1)
1. a kind of method that use freezing and crystallizing, decolouring, high vacuum rectification technique refine low-purity amino-glycerol, its feature exists
In：Comprise the following steps：A, by 120Kg amino-glycerols, amino-glycerol content 94.33%, GC are entered by unqualified amino-glycerol
Mouth is added in crystallization kettle, the chilled brine that temperature is -5--10 DEG C is passed through by cool brine import, after 80 minutes, into crystallization kettle
The compressed air that pressure is 0.25MPa is passed through, material is pressed into the first accurate filter；Enter back into decolouring kettle；
B, to decolouring kettle add 180Kg ethanol, stirring 40 minutes after open vapour heating, kettle temperature is risen to 55 DEG C after 30 minutes, with pressure
Power for 0.25MPa compressed air by 7.2Kg activated carbons, 4.8Kg atlapulgites be pressed into decolouring kettle, then at a temperature of 55 DEG C after
Continuous stirring 60 minutes；
Material in decolouring kettle is pressed into the second accurate filter and enters back into finished product steaming by C, the compressed air for being 0.25MPa with pressure
Kettle is evaporated, ethanol is first steamed, ethanol is continuing with；
D, when gas phase temperature is more than 80 DEG C, open Roots vacuum system, treat finished pot vacuum up to 0.0998MPa and stably,
When gas phase temperature is less than 124 DEG C, condensate liquid is front-end volatiles；The condensate liquid of 124-135 DEG C of gas phase temperature is finished product, and finished product amino is sweet
The purity of oil reaches 99.80%, GC.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510667225.7A CN105294457B (en) | 2014-03-25 | 2014-03-25 | A kind of method that use freezing and crystallizing, decolouring, high vacuum rectification technique refine low-purity amino-glycerol |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410111863.6A CN104109098B (en) | 2014-03-25 | 2014-03-25 | A kind of refining plant of amino-glycerol and purifying technique thereof |
| CN201510667225.7A CN105294457B (en) | 2014-03-25 | 2014-03-25 | A kind of method that use freezing and crystallizing, decolouring, high vacuum rectification technique refine low-purity amino-glycerol |
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| CN201410111863.6A Division CN104109098B (en) | 2014-03-25 | 2014-03-25 | A kind of refining plant of amino-glycerol and purifying technique thereof |
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| CN105294457B true CN105294457B (en) | 2017-09-19 |
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| CN201510667225.7A Active CN105294457B (en) | 2014-03-25 | 2014-03-25 | A kind of method that use freezing and crystallizing, decolouring, high vacuum rectification technique refine low-purity amino-glycerol |
| CN201510553882.9A Expired - Fee Related CN105198759B (en) | 2014-03-25 | 2014-03-25 | Method for producing high-purity qualified product through purification of colored 3-amino-1,2-propanediol with high impurity content |
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| CN109559589A (en) * | 2019-01-24 | 2019-04-02 | 河南莱帕克物联装备技术股份有限公司 | A kind of modularization teaching of aspirin production line practices device |
| CN110282901B (en) * | 2019-07-02 | 2021-07-13 | 安徽海螺新材料科技有限公司 | Cement grinding aid and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPH0812628A (en) * | 1994-06-27 | 1996-01-16 | Daicel Chem Ind Ltd | Production of 1-amino-2,3-propanediol |
| IT1290456B1 (en) * | 1997-04-04 | 1998-12-03 | Dibra Spa | PROCESS FOR THE PREPARATION OF AN AMINO ALCOHOL |
| WO2010148191A2 (en) * | 2009-06-17 | 2010-12-23 | Board Of Regents, The University Of Texas System | Compositions and methods for cyclofructans as separation agents |
| CN102603541A (en) * | 2012-02-20 | 2012-07-25 | 西安近代化学研究所 | Purification method of 3-amino-1,2-propanediol |
| CN103319355B (en) * | 2013-05-14 | 2015-03-25 | 西安近代化学研究所 | Separation and purification method of amino glycerol |
| CN103396325B (en) * | 2013-07-30 | 2014-12-24 | 潍坊沃尔特化学有限公司 | Amino-1,2-propanediol purification device and production method thereof |
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2014
- 2014-03-25 CN CN201410111863.6A patent/CN104109098B/en not_active Expired - Fee Related
- 2014-03-25 CN CN201510667225.7A patent/CN105294457B/en active Active
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| Publication number | Publication date |
|---|---|
| CN104109098B (en) | 2015-12-09 |
| CN105198759A (en) | 2015-12-30 |
| CN105198759B (en) | 2017-02-01 |
| CN104109098A (en) | 2014-10-22 |
| CN105294457A (en) | 2016-02-03 |
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