CN103147288B - Method for preparing halamine antibacterial material based on cyanuric chloride - Google Patents
Method for preparing halamine antibacterial material based on cyanuric chloride Download PDFInfo
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- CN103147288B CN103147288B CN201310056994.4A CN201310056994A CN103147288B CN 103147288 B CN103147288 B CN 103147288B CN 201310056994 A CN201310056994 A CN 201310056994A CN 103147288 B CN103147288 B CN 103147288B
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- cyanuric chloride
- dressing liquid
- mass percentage
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- antibacterial
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/35—Heterocyclic compounds
- D06M13/355—Heterocyclic compounds having six-membered heterocyclic rings
- D06M13/358—Triazines
- D06M13/364—Cyanuric acid; Isocyanuric acid; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2400/00—Specific information on the treatment or the process itself not provided in D06M23/00-D06M23/18
- D06M2400/01—Creating covalent bondings between the treating agent and the fibre
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- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Zoology (AREA)
- Dentistry (AREA)
- Environmental Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- Inorganic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
The invention discloses a method for preparing a halamine antibacterial material based on cyanuric chloride. The method comprises the following technological steps of: completely dissolving cyanuric chloride into an alkaline liquor to prepare a finishing liquor, soaking a material to be finished into the finishing liquor until the material is wet, then taking the material out and drying the material after the finishing, solidifying the material at 90-120 DEG C for 10-40 minutes, cleaning the material surface, and finally, halogenating, washing and drying to obtain the antibacterial material. The method is simple in technological operation, low in cost and moderate in reaction condition and has small influence on material mechanical property; and the finished material has excellent antibacterial performance and is safe and toxic-free.
Description
Technical field
The invention belongs to anti-biotic material technical field, be specifically related to a kind of preparation method of the halogen amine antimicrobial material based on Cyanuric Chloride.
Background technology
There is a large amount of causing a disease and cause mould harmful microorganism in human habitat, they can pass through the various materials such as fiber, plastics, rubber, paper and product surface is propagated, and threaten human health.Use long acting antibiotic material be effectively prevent that harmful microorganism from grow, breed, spread and propagating the most simply, safety and effective method.Traditional antiseptic for material antibiotic finish has heavy metal, quaternary ammonium salt, triclosan etc., but exist all in various degree expensive, antibacterial ability is weak, germicidal efficiency is low, the shortcoming such as harmful.The Halamine antibacterial agent that newly-developed gets up compensate for the deficiency of above-mentioned antiseptic, it has has a broad antifungal spectrum, sterilization is rapid, antibacterial activity is renewable, do not produce harmful by-products, to human body and the advantage such as environmentally friendly, have broad application prospects in material antibiotic finish field.
At present, the anti-biotic material preparation technology based on Halamine antibacterial agent still has the following disadvantages: relate to reactant more, expensive starting materials, severe reaction conditions, complex process, production cost is high; Raw material poorly water-soluble, utilization rate is low, need add a large amount of flammable organic solvent hydrotropy, add arrangement cost, and there is potential safety hazard; Finishing technique is comparatively large on material mechanical performance impact, and textiles strength loss is serious; The anti-microbial property of made anti-biotic material need to improve.
Summary of the invention
The above-mentioned defect that the applicant exists for existing halogen amine antimicrobial material preparation technology, provides a kind of preparation method of the halogen amine antimicrobial material based on Cyanuric Chloride.The inventive method technological operation is simple, with low cost, and reaction condition is gentle, and little on material mechanical performance impact, the material anti-microbial property after arrangement is excellent, safety non-toxic.
Object of the present invention is realized by following technical proposals:
A kind of preparation method of the halogen amine antimicrobial material based on Cyanuric Chloride, processing step is as follows: Cyanuric Chloride is dissolved in completely alkali lye and is prepared into dressing liquid, to treat that sorted material is soaked in this dressing liquid again, be as the criterion with drenched material, arrange complete, take out dry, in 90 ~ 120 DEG C of solidification 10 ~ 40min, clean this material surface, last halogenation, washing, oven dry, obtained anti-biotic material.
Its further technical scheme is:
Described alkali lye comprises NaOH, potassium hydroxide, sodium carbonate, potash, sodium bicarbonate or potassium bicarbonate solution, and its mass percentage concentration is 1 ~ 30%, is preferably 2 ~ 5%.
In described arrangement bath, the mass percentage concentration of described Cyanuric Chloride is 0.5 ~ 30%, is preferably 1 ~ 5%.
Described halogenation is adopt the solution containing reactive halogen to carry out immersion treatment to described material, the described solution containing reactive halogen comprises clorox, sodium hypobromite or calcium hypochlorite solution, its mass percentage concentration is 0.01 ~ 5%, and be preferably 0.01 ~ 0.5%, pH value is 4.0 ~ 12.0.
Describedly treat that sorted material comprises natural fabric or synthetic textile, plastics, sponge, natural rubber, synthetic rubber, timber, paper, coating, shitosan or chitin.
Described solidification process can adopt the modes such as baking oven bakes, hot iron, roller process, hot air treatment; When until sorted material be natural fabric or synthetic textile time, need after being soaked in dressing liquid to adopt traditional two leaching two methods of rolling to process, pick-up is 100%.
Compared with existing halogen amine antimicrobial material preparation technology, tool of the present invention has the following advantages:
1. directly with Cyanuric Chloride cheap and easy to get for raw material, be dissolved in alkali lye dressing liquid, raw material availability is high, does not need to add flammable organic solvent hydrotropy, operates very easy, with low cost.
2. process conditions are gentle, solidification temperature low (90 ~ 120 DEG C), and the time is short, and very little on material mechanical performance impact, after testing, the made antibacterial fabric strength loss of the present invention is all less than 20%, is obviously better than antibacterial fabric prepared by common process.
3. the made anti-biotic material of the present invention has excellent anti-microbial property, antimicrobial efficiency is high, its available chlorine content is in 0.1 ~ 1.0% scope, after testing, after antibacterial cotton fabric through arranging and inoculated bacteria are inoculated, 100%, 5min can be reached to the antibiotic rate of staphylococcus aureus interior to Escherichia coli O 157: the antibiotic rate of H7 can reach 100% in 10min.
4. preparation process and the formaldehydeless release of finished product, safety non-toxic.
Accompanying drawing explanation
Fig. 1 is antibiotic finish chemical principle figure in the embodiment of the present invention 1.
Fig. 2 is the made anti-biotic material sterilization of the present invention and bactericidal activity regeneration schematic diagram.
Fig. 3 is COTTON FABRIC infrared spectrum analysis figure, and wherein, (A) is blank sample, and (B) is the COTTON FABRIC before chlorination in embodiment 1, and (C) is the COTTON FABRIC after chlorination in embodiment 1.
Detailed description of the invention
Below in conjunction with accompanying drawing, and by embodiment, the present invention is specifically described.
As shown in Figure 1, first Cyanuric Chloride reacts with NaOH and generates soluble sodium salt, nucleophilic substitution is there is in cured condition with the active group (Cellulose-OH) of fiber textile, hydroxyl oxygen on cellulose replaces triazine chlorine in ring, thus makes above-mentioned sodium salt be connected to material surface.
As shown in Figure 2, the Halamine antibacterial agent being connected to material surface plays bactericidal action by its oxidisability chlorine atom, after effective chlorine releases, recovers anti-microbial property (regeneration) by chlorine drift.
Embodiment 1
1g Cyanuric Chloride, 2g NaOH are dissolved in completely in 97g distilled water and are prepared into dressing liquid, to wait again to arrange Nature Fibre Textile product (pure cotton fabric, purchased from Zhejiang Guandong Dyeing and Garment Co., Ltd.) be soaked in this dressing liquid 15min, two leachings two are rolled, pick-up 100%; Arrange complete, take out and be placed in dryer in 80 DEG C of oven dry 5min, then put into baker and bake 10min in 120 DEG C; Take out fabric, be standard soap flakes solution and its surface of a large amount of washed with de-ionized water of 0.5% by mass concentration, dry in room temperature; The fabric dried is soaked in (by dilute sulfuric acid adjust ph to 7.0) in the calcium hypochlorite solution of mass percentage concentration 0.01%, takes out fabric after 1h and use a large amount of clean water, in dryer, drying 2h in 45 DEG C, obtained antibacterial cotton fabric.The available chlorine content recording this antibacterial cotton fabric by iodimetric titration is 0.68%.
Embodiment 2
8g Cyanuric Chloride, 7g potassium hydroxide are dissolved in completely in 87g distilled water and are prepared into dressing liquid, to wait again to arrange Nature Fibre Textile product (pure cotton fabric, purchased from Zhejiang Guandong Dyeing and Garment Co., Ltd.) be soaked in this dressing liquid 15min, two leachings two are rolled, pick-up 100%; Arrange complete, take out and be placed in dryer in 80 DEG C of oven dry 5min, then put into baker and bake 40min in 90 DEG C; Take out fabric, be standard soap flakes solution and its surface of a large amount of washed with de-ionized water of 0.5% by mass concentration, dry in room temperature; The fabric dried is soaked in (by dilute sulfuric acid adjust ph to 12.0) in the liquor natrii hypochloritis of mass percentage concentration 0.5%, takes out fabric after 1h and use a large amount of clean water, in dryer, drying 2h in 45 DEG C, obtained antibacterial cotton fabric.The available chlorine content recording this antibacterial cotton fabric by iodimetric titration is 0.86%.
Embodiment 3
5g Cyanuric Chloride, 11g potassium hydroxide are dissolved in completely in 84g distilled water and are prepared into dressing liquid, to wait again to arrange Nature Fibre Textile product (pure cotton fabric, purchased from Zhejiang Guandong Dyeing and Garment Co., Ltd.) be soaked in this dressing liquid 15min, two leachings two are rolled, pick-up 100%; Arrange complete, take out and be placed in dryer in 80 DEG C of oven dry 5min, then put into baker and bake 20min in 100 DEG C; Take out fabric, be standard soap flakes solution and its surface of a large amount of washed with de-ionized water of 0.5% by mass concentration, dry in room temperature; The fabric dried is soaked in (by dilute sulfuric acid adjust ph to 7.0) in the liquor natrii hypochloritis of mass percentage concentration 0.1%, takes out fabric after 1h and use a large amount of clean water, in dryer, drying 2h in 45 DEG C, obtained antibacterial cotton fabric.The available chlorine content recording this antibacterial cotton fabric by iodimetric titration is 0.99%.
Antibacterial cotton fabric strength test:
According to ASTM D5035 method (pulling limit sliver sample method), carry out strength test to the made antibacterial cotton fabric of embodiment 1 ~ embodiment 3, strength loss is followed successively by 16%, 10%, 15%, is all less than 20%, be better than conventional finishing technique, prove that method for sorting of the present invention is less on fabric mechanics impact.
The FT-IRATR infrared spectrum analysis of antibacterial cotton fabric:
Adopt Fourier's attenuate total reflection spectrum (FT-IRATR) method of testing to test, using untrimmed COTTON FABRIC (the same) as blank sample, carry out infrared spectrum analysis to the COTTON FABRIC before and after chlorination in embodiment 1, test result is see Fig. 3.
As shown in Figure 3, (B) curve is at 1713cm
-1place and 1610cm
-1occurred new absworption peak, (C) curve is at 1700cm
-1and 1605cm
-1having there is new absworption peak in place, is the absworption peak of the carbonyl on triazine ring and double bond, proves that triazine ring has been connected in COTTON FABRIC.
The anti-microbial property test of antibacterial cotton fabric:
According to correction AATCC100-1999 anti-microbial property testing standard, method is tested, COTTON FABRIC in embodiment 2 before chlorination is as blank sample, anti-microbial property test is carried out to the made antibacterial cotton fabric of embodiment 2 (available chlorine content 0.86%), inoculated bacteria is staphylococcus aureus and Escherichia coli O 157: H7, and test result is see table 1 and table 2.
Table 1 antibacterial cotton fabric is to the anti-microbial property of staphylococcus aureus
Note: the inoculum density of staphylococcus aureus: 1.80x10
7cfu/ sample, log reduction is 7.26 namely all to kill.
Table 2 antibacterial cotton fabric is to Escherichia coli O 157: the anti-microbial property of H7
The inoculum density of note: Escherichia coli O 157: H7: 2.67x10
7cfu/ sample, log reduction is 7.43 namely all to kill.
The test data of table 1 and table 2 shows, the COTTON FABRIC arranged by the inventive method has excellent anti-microbial property, after contacting with inoculated bacteria, 100%, 5min can be reached to the antibiotic rate of staphylococcus aureus interior to Escherichia coli O 157: the antibiotic rate of H7 can reach 100% in above-mentioned antibacterial cotton fabric 10min.
Above embodiment and Application Example relate to each raw material and reagent is commercially available prod, and institute's use production equipment is this area conventional equipment, wherein, and staphylococcus aureus and Escherichia coli O 157: H7 purchased from American Type culture collection warehousing (ATCC).
Above-described only for purpose of explanation, the invention is not restricted to above embodiment.Be appreciated that the oher improvements and changes that those skilled in the art directly derive without departing from the spirit and concept in the present invention or associate, all should think and be included within protection scope of the present invention.
Claims (3)
1. the preparation method based on the halogen amine antimicrobial material of Cyanuric Chloride, it is characterized in that processing step is as follows: Cyanuric Chloride is dissolved in completely alkali lye and is prepared into dressing liquid, to treat that sorted material is soaked in this dressing liquid again, be as the criterion with drenched material, arrange complete, take out dry, in 90 ~ 120 DEG C of solidification 10 ~ 40min, clean this material surface, last halogenation, washing, oven dry, obtained anti-biotic material; In described arrangement bath, the mass percentage concentration of described Cyanuric Chloride is 1 ~ 5%;
Described alkali lye comprises NaOH, potassium hydroxide, sodium carbonate, potash, sodium bicarbonate or potassium bicarbonate solution, and the mass percentage concentration of described alkali lye is 2 ~ 5%;
Described halogenation is adopt the solution containing reactive halogen to carry out immersion treatment to described material, and the described solution containing reactive halogen comprises clorox, sodium hypobromite or calcium hypochlorite solution, and its mass percentage concentration is 0.01 ~ 5%.
2. the preparation method of halogen amine antimicrobial material according to claim 1, is characterized in that: described in treat that sorted material comprises natural fabric or synthetic textile, plastics, sponge, natural rubber, synthetic rubber, timber, paper, coating, shitosan or chitin.
3. the preparation method of halogen amine antimicrobial material according to claim 1, is characterized in that: also comprise and carry out to the natural fabric or synthetic textile that are soaked in described dressing liquid the step that two leachings two roll.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310056994.4A CN103147288B (en) | 2013-02-22 | 2013-02-22 | Method for preparing halamine antibacterial material based on cyanuric chloride |
| US14/768,450 US20160076194A1 (en) | 2013-02-22 | 2014-02-17 | The preparation of N-halamine antibacterial materials based on cyanuric chloride |
| PCT/CN2014/072161 WO2014127713A1 (en) | 2013-02-22 | 2014-02-17 | Method for preparing cyanuric chloride-based halogenoamine antibacterial material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310056994.4A CN103147288B (en) | 2013-02-22 | 2013-02-22 | Method for preparing halamine antibacterial material based on cyanuric chloride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103147288A CN103147288A (en) | 2013-06-12 |
| CN103147288B true CN103147288B (en) | 2015-03-11 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN201310056994.4A Active CN103147288B (en) | 2013-02-22 | 2013-02-22 | Method for preparing halamine antibacterial material based on cyanuric chloride |
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| Country | Link |
|---|---|
| US (1) | US20160076194A1 (en) |
| CN (1) | CN103147288B (en) |
| WO (1) | WO2014127713A1 (en) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103147288B (en) * | 2013-02-22 | 2015-03-11 | 江南大学 | Method for preparing halamine antibacterial material based on cyanuric chloride |
| CN104140475B (en) * | 2014-08-06 | 2017-01-18 | 上海工程技术大学 | Method for preparing quaternization chitosan |
| US10897905B2 (en) | 2016-01-26 | 2021-01-26 | Metrex Research, LLC | Hypochlorite based hard surface disinfectants |
| US10986841B2 (en) | 2018-11-06 | 2021-04-27 | The Clorox Company | Bleach compositions |
| CN111041829B (en) * | 2019-12-30 | 2023-08-25 | 华侨大学 | Preparation method of reactive chitosan-based fabric antibacterial agent |
| CN111686696B (en) * | 2020-04-22 | 2023-04-07 | 杭州嘉澍环境监测有限公司 | Aminobenzene sulfonic acid modified glutaraldehyde cross-linked chitin gel material, preparation thereof and application thereof as noble metal gold adsorption material |
| US11845916B2 (en) | 2020-06-24 | 2023-12-19 | The Clorox Company | Burstable sporicidal cleaning wipe system containing stabilized hypochlorite |
| CN114381073B (en) * | 2021-12-15 | 2023-09-29 | 珠海市睿住建筑科技有限公司 | Ultraviolet aging resistant chitosan-polyvinyl chloride wood-plastic board and preparation method thereof |
| CN114672998B (en) * | 2022-04-12 | 2022-12-20 | 福州大学 | Preparation method of antibacterial and mildewproof polypropylene |
| CN114775264B (en) * | 2022-04-22 | 2023-06-23 | 安徽大学 | Method for preparing nitrogen halamine type antibacterial cotton fabric by ATRP method |
| CN115322267B (en) * | 2022-07-14 | 2023-10-24 | 四川大学 | Preparation method of biomass-based amphoteric synthetic tanning agent |
| CN115888834B (en) * | 2022-10-31 | 2024-07-19 | 南京邮电大学 | Metal organic framework photocatalytic bactericide grafted with N-halamine and preparation method and application thereof |
| CN116356563B (en) * | 2023-02-21 | 2023-11-14 | 江苏箭鹿毛纺股份有限公司 | Antibacterial fabric and preparation method thereof |
| CN117385490B (en) * | 2023-11-02 | 2024-08-16 | 中拓特纺(常州)纺织科技有限公司 | Antibacterial fabric based on modified polyester fiber |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPH06341073A (en) * | 1994-01-10 | 1994-12-13 | Kunio Mori | Adherent composite material of steel wire and rubber |
| JPH1096169A (en) * | 1996-09-20 | 1998-04-14 | Toyobo Co Ltd | Skin care fiber product and its production |
| CN101215267B (en) * | 2007-12-26 | 2011-04-27 | 东华大学 | Ultraviolet ray absorbent with double reaction active groups used for cotton, preparation and application thereof |
| CN101250815A (en) * | 2008-03-24 | 2008-08-27 | 王加旺 | Method for manufacturing halogen amine antimicrobial material |
| CN102797150B (en) * | 2012-08-17 | 2014-04-30 | 江南大学 | Halamine antibacterial agent, its preparation method and application |
| CN103147288B (en) * | 2013-02-22 | 2015-03-11 | 江南大学 | Method for preparing halamine antibacterial material based on cyanuric chloride |
-
2013
- 2013-02-22 CN CN201310056994.4A patent/CN103147288B/en active Active
-
2014
- 2014-02-17 WO PCT/CN2014/072161 patent/WO2014127713A1/en active Application Filing
- 2014-02-17 US US14/768,450 patent/US20160076194A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20160076194A1 (en) | 2016-03-17 |
| CN103147288A (en) | 2013-06-12 |
| WO2014127713A1 (en) | 2014-08-28 |
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