CN110548491A - Efficient adsorption material for adsorbing toxic substances in cigarette smoke - Google Patents

Efficient adsorption material for adsorbing toxic substances in cigarette smoke Download PDF

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Publication number
CN110548491A
CN110548491A CN201910701173.9A CN201910701173A CN110548491A CN 110548491 A CN110548491 A CN 110548491A CN 201910701173 A CN201910701173 A CN 201910701173A CN 110548491 A CN110548491 A CN 110548491A
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phenol
ammonia
initiator
cigarette smoke
toxic substances
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CN201910701173.9A
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Chinese (zh)
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俞豪杰
法扎勒·哈克
王立
林腾飞
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Zhejiang University ZJU
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Zhejiang University ZJU
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    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01DSEPARATION
    • B01D53/00Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
    • B01D53/02Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by adsorption, e.g. preparative gas chromatography
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/22Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
    • B01J20/24Naturally occurring macromolecular compounds, e.g. humic acids or their derivatives
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30Processes for preparing, regenerating, or reactivating
    • B01J20/3085Chemical treatments not covered by groups B01J20/3007 - B01J20/3078
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F251/00Macromolecular compounds obtained by polymerising monomers on to polysaccharides or derivatives thereof
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01DSEPARATION
    • B01D2253/00Adsorbents used in seperation treatment of gases and vapours
    • B01D2253/20Organic adsorbents
    • B01D2253/202Polymeric adsorbents
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01DSEPARATION
    • B01D2257/00Components to be removed
    • B01D2257/40Nitrogen compounds
    • B01D2257/406Ammonia
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01DSEPARATION
    • B01D2257/00Components to be removed
    • B01D2257/70Organic compounds not provided for in groups B01D2257/00 - B01D2257/602
    • B01D2257/708Volatile organic compounds V.O.C.'s
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01DSEPARATION
    • B01D2258/00Sources of waste gases
    • B01D2258/02Other waste gases
    • B01D2258/0283Flue gases
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2220/00Aspects relating to sorbent materials
    • B01J2220/40Aspects relating to the composition of sorbent or filter aid materials
    • B01J2220/48Sorbents characterised by the starting material used for their preparation
    • B01J2220/4812Sorbents characterised by the starting material used for their preparation the starting material being of organic character
    • B01J2220/4825Polysaccharides or cellulose materials, e.g. starch, chitin, sawdust, wood, straw, cotton

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Analytical Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)

Abstract

The invention discloses a high-efficiency adsorption material for adsorbing toxic substances in cigarette smoke. Grafting methacrylic acid onto a carboxymethyl starch (CMS) main chain through free radical polymerization to obtain modified starch; adding an initiator into the modified starch in the grafting preparation process, wherein the initiator is a water-soluble initiator; the conditions of the free radical polymerization grafting reaction are that the polymerization is initiated by heating: the reaction temperature is 50-80 ℃, and the reaction time is 2-12 h. The preparation method is simple, and the obtained macromolecular adsorption material has excellent adsorption and removal performance on toxic substances, namely ammonia and phenol in cigarette smoke.

Description

Efficient adsorption material for adsorbing toxic substances in cigarette smoke
Technical Field
The invention belongs to an adsorption material in the technical field of high polymer materials, and particularly relates to a high-efficiency adsorption material for adsorbing toxic substances, namely ammonia and phenol in cigarette smoke.
Background
The cigarette smoke contains various toxic and harmful gases, which can cause different diseases and harm health. It is presumed that about 69 chemicals among 7000 chemicals present in cigarette smoke are carcinogenic [ productive Medicine,2018,106,31-37 ]. Ammonia and phenol are two typical toxic substances present in cigarette smoke. Ammonia gas can cause eye irritation, bronchitis, pulmonary alveolar edema and other diseases, and can also increase the addiction to cigarettes. Phenol increases the risk of cancer, muscle weakness, convulsions and coordination injuries. Therefore, it is very important to reduce or remove ammonia and phenol in cigarette smoke.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides a high-efficiency adsorption material for adsorbing toxic substances of ammonia and phenol in cigarette smoke and a preparation method thereof. The adsorbent has good adsorption and removal effects on gaseous ammonia and phenol in cigarette smoke. The adsorption mode is easy to operate, simple, efficient and low in cost, and can be widely applied to adsorption of harmful substances in cigarette smoke.
In order to achieve the purpose, the invention is realized by the following technical scheme:
The invention grafts methacrylic acid to a carboxymethyl starch (CMS) main chain through free radical polymerization to obtain modified starch.
The grafting monomer of the invention is methacrylic acid (MAA) and the starch is carboxymethyl starch (CMS).
the modified starch is added with an initiator in the grafting preparation process, and the initiator is a water-soluble initiator.
The initiator adopts ammonium persulfate or potassium persulfate.
in the reaction system, the carboxymethyl starch, the methacrylic acid, the initiator and the deionized water are mixed according to the mass part ratio and comprise the following components:
Preferably, the composition of the adsorption material comprises, by mass, 2.1 parts of carboxymethyl starch, 16.4 parts of methacrylic acid, 0.56 part of initiator and 100 parts of deionized water.
The conditions of the free radical polymerization grafting reaction are that the polymerization is initiated by heating: the reaction temperature is 50-80 ℃, and the reaction time is 2-12 h.
The specific preparation method of the high-efficiency adsorbing material comprises the following steps:
(1) Dissolving carboxymethyl starch in deionized water, and continuously stirring at 70 ℃ and a rotating speed of 450rpm in an argon atmosphere;
(2) Adding an initiator potassium persulfate solution dissolved in deionized water to generate reaction sites on the carboxymethyl starch to initiate continuous reaction to obtain a reaction mixture;
(3) Dripping monomer methacrylic acid into the reaction mixture, and continuing to react for 2 hours;
(4) Stopping the reaction after 2 hours, and cooling the reaction mixed solution at normal temperature for 40 min;
(5) After cooling, the mixture was washed with a mixture of methanol and water (methanol to water volume ratio 70:30) and centrifuged five times; washing the obtained product with deionized water for three times, and finally washing with ethanol for five times to completely remove homopolymer, monomer and other impurities;
(6) The obtained product was completely dried in a vacuum oven at 40 ℃ for 24 hours to obtain dry powder of CMS-g-PMAA3 as a high efficiency adsorbent.
The reaction formula is shown in figure 1.
The invention has the following beneficial effects:
The preparation method is simple, and the obtained macromolecular adsorption material has excellent adsorption and removal performance on toxic substances, namely ammonia and phenol in cigarette smoke.
The adsorption material provided by the invention is a novel high polymer material, has good adsorbability on gaseous ammonia and phenol, and can adsorb and fix ammonia and phenol in cigarette smoke, thereby achieving good adsorption and removal effects.
Drawings
FIG. 1 is a reaction scheme for synthesizing CMS-g-PMAAs in example 1, example 2, and example 3.
figure 2 is a schematic of the cigarette glass filter tube filling in example 4.
FIG. 3 is a diagram showing an apparatus for adsorbing ammonia and phenol in gaseous state in examples 5 and 6 and a comparison of adsorption efficiencies of 4 different adsorbents for ammonia and phenol.
FIG. 3(a) is a diagram of an apparatus for measuring the adsorption performance of ammonia in the example;
FIG. 3(b) is a diagram of an apparatus for testing the adsorption performance of phenol in the example;
FIG. 3(c) is a graph of pH of a hydrochloric acid solution in a device as a function of time;
FIG. 3(d) is a graph comparing the adsorption efficiency of different adsorbents for ammonia;
FIG. 3(e) is a graph comparing the adsorption efficiency of different adsorbents for phenol;
Detailed Description
The following examples are provided to more clearly illustrate the technical solutions of the present invention, and should not be construed as limiting the scope of the present invention.
The examples of the invention are as follows:
example 1
The preparation method comprises the following steps of (1) mixing carboxymethyl starch, methacrylic acid, potassium persulfate and deionized water in parts by mass: 2.1 parts of carboxymethyl starch, 16.4 parts of methacrylic acid, 0.56 part of potassium persulfate and 100 parts of deionized water.
The preparation method comprises the following steps:
(1) 1.0463g (6.45mmol) of carboxymethyl starch was dissolved in 30ml of deionized water and stirred at 70 ℃ under 450rpm under argon atmosphere for 30 min.
(2) 278.9mg (1.03mmol) of potassium persulfate as an initiator dissolved in 20ml of deionized water was added and the reaction was continued for 30 min.
(3) 8.2ml (96.75mmol) of monomeric methacrylic acid were added dropwise to the reaction mixture, and the reaction was continued for 2 hours.
(4) After 2 hours, the reaction was stopped and the reaction mixture was cooled at room temperature for 40 min.
(5) After cooling, the mixture was washed with a mixture of methanol and water (volume 70:30) and centrifuged five times. The resulting product was washed three times with deionized water and finally five times with ethanol to completely remove homopolymers, monomers and other impurities.
(6) The product was placed in a vacuum oven at 40 ℃ for 24 hours to completely dry. Finally, a dry powder of CMS-g-PMAA3 was obtained and placed in a desiccator for further characterization and application.
Example 2
The preparation method comprises the following steps of (1) mixing carboxymethyl starch, methacrylic acid, potassium persulfate and deionized water in parts by mass: 2.2 parts of carboxymethyl starch, 5.3 parts of methacrylic acid, 0.22 part of potassium persulfate and 100 parts of deionized water.
The preparation method comprises the following steps:
(1) 1.0884g (6.71mmol) of carboxymethyl starch was dissolved in 30ml of deionized water and stirred at 70 ℃ under 450rpm under argon atmosphere for 30 min.
(2) 108.8mg (0.4026mmol) of potassium persulfate as an initiator dissolved in 20ml of deionized water was added and the reaction was continued for 30 min.
(3) 2.6ml (33.55mmol) of monomeric methacrylic acid were added dropwise to the reaction mixture and the reaction was continued for 2 hours.
(4) After 2 hours, the reaction was stopped and the reaction mixture was cooled at room temperature for 40 min.
(5) After cooling, the mixture was washed with a mixture of methanol and water (volume 70:30) and centrifuged five times. The resulting product was washed three times with deionized water and finally five times with ethanol to completely remove homopolymers, monomers and other impurities.
(6) The product was placed in a vacuum oven at 40 ℃ for 24 hours to completely dry. Finally, a dry powder of CMS-g-PMAA2 was obtained and placed in a desiccator for further characterization and application.
Example 3
the preparation method comprises the following steps of (1) mixing carboxymethyl starch, methacrylic acid, potassium persulfate and deionized water in parts by mass: 2.2 parts of carboxymethyl starch, 2.7 parts of methacrylic acid, 0.13 part of potassium persulfate and 100 parts of deionized water.
The preparation method comprises the following steps:
(1) 1.0682g (6.58mmol) of carboxymethyl starch was dissolved in 30ml of deionized water and stirred at 70 ℃ under 450rpm under argon atmosphere for 30 min.
(2) 62.2mg (0.2303mmol) of potassium persulfate as an initiator dissolved in 20ml of deionized water was added and the reaction was continued for 30 min.
(3) 1.3ml (16.45mmol) of monomeric methacrylic acid were added dropwise to the reaction mixture, and the reaction was continued for 2 hours.
(4) After 2 hours, the reaction was stopped and the reaction mixture was cooled at room temperature for 40 min.
(5) after cooling, the mixture was washed with a mixture of methanol and water (volume 70:30) and centrifuged five times. The resulting product was washed three times with deionized water and finally five times with ethanol to completely remove homopolymers, monomers and other impurities.
(6) The product was placed in a vacuum oven at 40 ℃ for 24 hours to completely dry. Finally, a dry powder of CMS-g-PMAA1 was obtained and placed in a desiccator for further characterization and application.
Testing of the examples
A. Filter tube filling
The adsorption study was performed on gaseous ammonia and phenol using a glass filter tube. These glass tubes are filled with blank cigarette filter rods with adsorbent. The sample tube filling process is as follows: firstly, all the cigarette filter sticks are taken out, then the cigarette filter sticks are cut into two equal parts, and one half of the cigarette filter sticks are put into a filter tube. After the addition of the adsorbent material, the other half was added. The adsorption material is clamped between the two parts of the cigarette filter stick. Thus, all filter tubes are filled, 4 filter tubes are filled with the adsorption material, and 1 filter tube is filled with the cigarette filter stick as a reference blank tube. The adsorption materials filled in the filter tube are CMS, CMS-g-PMAA1, CMS-g-PMAA2 and CMS-g-PMAA3 respectively.
B. Ammonia adsorption Performance test [ see FIG. 3(a) ]
(1) the ammonia adsorption performance test was performed at 25 ℃. In order to obtain the result of the adsorption property of the adsorbent for ammonia, 150ml of an aqueous ammonia solution (0.98mol/L) was placed in the two-necked round-bottomed flask (B).
(2) One end of the round-bottom flask is connected with an argon inlet (A), and the other end is connected with a flowmeter (C).
(3) One end (C) of the flow meter is connected with the ammonia source solution in the double-neck round-bottom flask (B), and the other end is connected with 5 glass filter tubes (D) through pipes.
(4) Each filter tube (D) is connected with one of 5 conical flasks (E).
(5) All 5 erlenmeyer flasks (E) were connected to 5 other erlenmeyer flasks (F), respectively.
(6) argon was passed through the aqueous ammonia solution (B) to form an argon-ammonia gaseous mixture.
(7) the gaseous mixture was passed through a flow meter (C) which controlled the flow of gas at a rate of 0.4m 3/h.
(8) The flow meter (C) lets the gas enter the glass filter tube (D), 4 of 5 glass filter tubes are filled with cigarette filter elements (CMS10.4mg, CMS-g-PMAA110.4mg, CMS-g-PMAA210.5mg and CMS-g-PMAA310.4mg) containing adsorbing materials, and 1 cigarette filter stick is arranged.
(9) Where the adsorption material adsorbs a certain amount of ammonia and the remaining ammonia is passed through 5 erlenmeyer flasks (E) containing 75ml of 0.05mol/LHCl solution. The remaining ammonia was adsorbed by HCl solution, which was changed in pH by a pH meter.
(10) the remaining ammonia was passed through another 5 erlenmeyer flasks (F) containing 100ml of water to achieve complete adsorption.
(11) After a certain adsorption time, the change in pH of the HCl solution was determined by a pH meter. Finally, by obtaining HCl solutions of different pH values in Erlenmeyer flasks (E) connected to each glass filter tube (D), the HCl concentration was calculated from the following formula (r).
[H+]=10-pH
Here [ H + ] is the acid concentration in the Erlenmeyer flask (E) connected to Erlenmeyer flask (F.) this concentration is always less than the initial concentration, since part of the hydrochloric acid is used for the neutralization reaction with ammonia.
The amount of ammonia adsorbed by an adsorbent was calculated by multiplying the difference between the residual hydrochloric acid concentrations of the adsorbent and the blank sample by the volume of the hydrochloric acid solution using the following equation.
X=[[H+]Ads-[H+]blank]V②
Where "X" is the amount of ammonia adsorbed by the particular adsorbent material (in moles) compared to the blank sample, "[ H + ] Ads" is the concentration of hydrochloric acid in the remaining flask added to the glass filter tube of the particular adsorbent material, "[ H + ] blank" is the remaining concentration of hydrochloric acid in the flask attached to the blank glass filter tube, and "V" is the volume of hydrochloric acid solution.
C. Phenol adsorption Performance test [ see FIG. 3(b) ]
(1) To obtain the results of the adsorption performance of the adsorbent material on phenol, a phenol solution containing 30.2483g (321.53mmol) of a mixture of phenol in water (100ml) and ethanol (50ml) was prepared in a two-necked round-bottomed flask (C).
(2) One end of flask (C) (placed in an oil bath at 35 ℃ C.) containing the phenol solution was connected to a flow meter (B), and the other end was connected to 5 glass filter tubes (D).
(3) 5 glass filter tubes (D) were connected to 5 flasks (E) which were then connected to 5 other flasks (F).
(4) Argon (A) was passed through a flow meter (B) which controlled the gas flow at a rate of 0.4m 3/h.
(5) When argon (a) is passed through phenol solution (C), an argon-phenol gaseous mixture is formed.
(6) The gaseous argon-phenol mixture was passed through a glass filter tube (D) containing adsorbent materials (CMS30.2mg, CMS-g-PMAA130.1mg, CMS-g-PMAA230.1mg and CMS-g-PMAA330.2mg) and the sample adsorbed an amount of phenol in the glass filter tube.
(7) And the remaining phenol was passed into an Erlenmeyer flask (E) containing 75ml of ethanol, which adsorbed phenol, the concentration of phenol in ethanol being varied with the adsorption of phenol.
(8) The remaining phenol was passed into another set of erlenmeyer flasks (F) each containing 100ml of water, at which point the phenol was completely absorbed.
(9) in order to determine the amount of phenol adsorbed by the adsorbent, a 2ml sample of ethanol was taken from each Erlenmeyer flask (E) after a phenol adsorption test experiment was conducted for 30min and studied by an ultraviolet spectrophotometer method. Finally, the concentration of phenol in the blank ethanol solution was subtracted from the concentration of phenol in the sample ethanol solution to determine the concentration of phenol adsorbed by each adsorbent.
The experimental results of FIG. 3 show that the adsorption material provided by the invention has good adsorption performance on ammonia and phenol, and the maximum adsorption efficiencies of CMS, CMS-g-PMAA1, CMS-g-PMAA2 and CMS-g-PMAA3 on ammonia are respectively 0.005g/g, 0.020g/g, 0.023g/g and 0.031 g/g. For phenol, the adsorption efficiencies of CMS, CMS-g-PMAA1, CMS-g-PMAA2, and CMS-g-PMAA3 were 0.2085g/g, 0.2445g/g, 0.2473g/g, and 0.2501g/g, respectively.
Although the present invention has been described in detail with reference to the foregoing embodiments, it will be apparent to those skilled in the art that changes may be made in the embodiments and/or equivalents thereof without departing from the spirit and scope of the invention. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.

Claims (5)

1. The utility model provides a toxic substance ammonia and phenol adsorption's high-efficient adsorption material for in cigarette flue gas which characterized in that: grafting methacrylic acid onto a carboxymethyl starch (CMS) backbone by free radical polymerization to obtain a modified starch.
2. The high-efficiency adsorption material for adsorbing toxic substances of ammonia and phenol in cigarette smoke according to claim 1, which is characterized in that: the modified starch is added with an initiator in the grafting preparation process, and the initiator is a water-soluble initiator.
3. The high-efficiency adsorption material for adsorbing toxic substances of ammonia and phenol in cigarette smoke according to claim 2, which is characterized in that: the initiator adopts ammonium persulfate or potassium persulfate.
4. the efficient adsorbing material for adsorbing toxic substances, namely ammonia and phenol, in cigarette smoke according to claim 1, characterized in that the carboxymethyl starch, the methacrylic acid, the initiator and the deionized water in a reaction system are prepared from the following components in parts by mass:
5. The high-efficiency adsorption material for adsorbing toxic substances of ammonia and phenol in cigarette smoke according to claim 1, which is characterized in that: the conditions of the free radical polymerization grafting reaction are that the polymerization is initiated by heating: the reaction temperature is 50-80 ℃, and the reaction time is 2-12 h.
CN201910701173.9A 2019-07-31 2019-07-31 Efficient adsorption material for adsorbing toxic substances in cigarette smoke Pending CN110548491A (en)

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Citations (5)

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Publication number Priority date Publication date Assignee Title
CN1916045A (en) * 2006-08-21 2007-02-21 中国科学院成都有机化学有限公司 Method for preparing starch grafted copolymer of dimethylaminoethyl methacrylate
CN103242786A (en) * 2013-04-22 2013-08-14 常州大学 Preparation method of environment-friendly modified starch adhesive for cigarette
CN103923428A (en) * 2014-04-24 2014-07-16 河南工业大学 Starch-based porous hydrogel and preparation method thereof
CN105254812A (en) * 2015-11-11 2016-01-20 江南大学 Grafted starch slurry preparation method based on enzymatic cascade reaction
US20170174927A1 (en) * 2015-12-18 2017-06-22 Michelman, Inc. Ionomer-based digital printable coatings for various substrates

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1916045A (en) * 2006-08-21 2007-02-21 中国科学院成都有机化学有限公司 Method for preparing starch grafted copolymer of dimethylaminoethyl methacrylate
CN103242786A (en) * 2013-04-22 2013-08-14 常州大学 Preparation method of environment-friendly modified starch adhesive for cigarette
CN103923428A (en) * 2014-04-24 2014-07-16 河南工业大学 Starch-based porous hydrogel and preparation method thereof
CN105254812A (en) * 2015-11-11 2016-01-20 江南大学 Grafted starch slurry preparation method based on enzymatic cascade reaction
US20170174927A1 (en) * 2015-12-18 2017-06-22 Michelman, Inc. Ionomer-based digital printable coatings for various substrates

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* Cited by examiner, † Cited by third party
Title
MUHAMMAD HAROON ET AL.,: ""Synthesis and characterization of carboxymethyl starch-g-polyacrylic acids and their properties as adsorbents for ammonia and phenol"", 《 INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES》 *

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Application publication date: 20191210