CN110387017A - Combed polycarboxylate salt dispersant containing polyether lateral chain and preparation method thereof - Google Patents
Combed polycarboxylate salt dispersant containing polyether lateral chain and preparation method thereof Download PDFInfo
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- CN110387017A CN110387017A CN201910741657.6A CN201910741657A CN110387017A CN 110387017 A CN110387017 A CN 110387017A CN 201910741657 A CN201910741657 A CN 201910741657A CN 110387017 A CN110387017 A CN 110387017A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
- C08F283/065—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals on to unsaturated polyethers, polyoxymethylenes or polyacetals
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- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
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Abstract
The present invention provides a kind of combed polycarboxylate salt dispersant and preparation method thereof containing polyether lateral chain, which is mixed by the component of following mass ratio: 4-50 parts of allyl polyethenoxy ether, 1-10 parts of acrylic homolog and 1-10 parts of acrylate.Its method includes: (1), a certain amount of chain-transferring agent, water and methanol is added in reaction vessels, and stirring is heated to 90 DEG C or more;(2), the mixed solution of allyl polyethenoxy ether, acrylic homolog, acrylate and a certain amount of methanol is added dropwise into reaction vessel with constant flow pump;Initiator solution is added dropwise into reaction flask with another constant flow pump;Master control time for adding is 1-2 hours, keeps the temperature 2-3h after dripping;(3) it is cooled to room temperature, being neutralized to pH with aqueous slkali is 7~8, then heats to 110 DEG C or more and steams methanol.
Description
Technical field
The present invention relates to a kind of combed polycarboxylate salt dispersant and preparation method thereof containing polyether lateral chain, is related to one in other words
Kind has the polycarboxylate surfactant and preparation method thereof of polyoxyethylene ether branch.
Background technique
Dispersing agent plays dispersion and stable effect to by dispersed substance, in pigment, dyestuff, aqueous solution coal slurry, pesticide etc.
Industry suffers from important application.Polycarboxylate salt dispersant is a kind of new and effective agricultural dispersants, which has long carbon
Chain, more adsorption site.Branched group such as carboxyl, sulfonic group, amino and polyoxyethylene base side chain etc. can play space
Repulsive interaction, therefore its special construction has good dispersion performance to suspension system.With traditional lignosulfonates, naphthalene sulphur
Hydrochlorate formaldehyde condensation products sodium salt dispersing agent is compared, and the dispersion stabilization of polycarboxylate salt dispersant is high first, is not easily susceptible to suspended substance
The influence of ion, pH value in system and temperature;Secondly polycarboxylate salt dispersant can be adsorbed on raw medicine particle surface, make raw medicine
Particle has preferable spreadability in plant leaf surface, to reach maximum drug effect.And combed polycarboxylate salt dispersant, because of its combed knot
Structure has independent suction-operated, can form multiple spot absorption, and the macromolecule carbochain hydrophobic group of suitable length at raw medicine interface
Group protrudes into water phase and is centered around around powder, and by steric barrier effect, can significantly improve the stability of dispersant system.Research
Show that the side chain polycarboxylate containing polyethers has good dispersion performance, when polycarboxylic-acid high polymer is added to pesticidal aqueous suspension
In agent, pesticide granules surface is adsorbed on by hydrophobic chain, carboxyl enhances the electrostatic repulsion between pesticide granules, in polyethylene oxide side chains
Oxygen and hydrone on ehter bond form hydrogen bond, to form hydrophily stereoscopic film, generate wetting, suction-operated in solid liquid interface,
To generate peptizaiton to system.
But the synthesis technology of existing dispersing agent, it is mostly manual operations, labor efficiency is low, and technique also not environmentally, and is deposited
Molecular size range is difficult to control, system viscosity is high, the technology for being difficult to overcome such as undesirable to part pesticide dispersion effect is asked
Topic.
Although having there is deep technological accumulation in terms of polymer molecular weight control, such as application No. is
(200810201806.1 styrene-styrene sodium sulfonate-hydroxypropyl acrylate ternary polymerization dispersing agent), 201110055926.7
(methacrylic acid-Styrene And Chloroalkyl Acrylates hydroxypropyl acrylate terpolymer dispersants), 201110440872.6 (methacrylic acids-benzene
Ethylene binary copolymerization dispersing agent) and 201110440854.8 (methacrylic acids-phenylethylene-maleic anhydride ternary polymerization dispersing agent)
Chinese patent literature, the also " synthesis and its dispersibility of acrylic copolymer dispersing agent as delivered on process engineering journal
Can ".And in addition to this, it controls the method for polymer molecular weight size also in the art: being made using sulfhydryl compound
Polymer molecular weight (such as European patent document of Publication No. EP1304314) is controlled for chain-transferring agent;Made using metal salt
For molecular weight regulator (such as Chinese patent literature of Publication No. CN1085570);It polymerize in water-isopropyl alcohol mixed solvent
Reaction achievees the purpose that control polymer molecular weight (such as american documentation literature of Publication No. US4301226) etc..But this
The shortcomings that a little methods, is: the substance due to introducing penetrating odor in product, and then causes pollution environment, and after increasing
The difficulty of reason, further such that production cost is higher.
Summary of the invention
Technical problem to be solved by the present invention lies in drawbacks described above of the existing technology is overcome, a kind of molecular weight is provided
System easy to control in size, dispersion performance is good, good, at low cost, the environmentally friendly combed containing polyoxyethylene ether side chain of stability is poly-
Carboxylate dispersants' (surfactant) and its preparation process.
Its technical problem to be solved can be implemented by the following technical programs.
A kind of combed polycarboxylate salt dispersant containing polyether lateral chain, is mixed by the component of following mass ratio:
4-50 parts of allyl polyethenoxy ether
1-10 parts of acrylic homolog
1-10 parts of acrylate.
As the preferred embodiment of the present invention, combed polycarboxylate salt dispersant by the component mixing of following mass ratio and
At: 40 parts of allyl polyethenoxy ether;10 parts of acrylic homolog;10 parts of acrylate.
Also be used as the preferred embodiment of the present invention, combed polycarboxylate salt dispersant by following mass ratio component mixing and
At: 30 parts of allyl polyethenoxy ether;8 parts of acrylic homolog;5 parts of acrylate.
As the further improvement of the technical program, the acrylic homolog is one in acrylic acid and methacrylic acid
Kind is a variety of.
Also as the further improvement of the technical program, the acrylate is methyl acrylate, ethyl acrylate and third
One of olefin(e) acid N-butyl is a variety of.
Another technical problem to be solved by this invention is to provide a kind of combed polycarboxylate dispersion containing polyether lateral chain
The preparation method of agent, this method use following steps:
(1), chain-transferring agent, water and methanol 1:1 mixing (80%-90% of monomer mass) are added in reaction flask, stirs,
It is heated to 90 DEG C or more;
(2), be added dropwise with constant flow pump into reaction vessel allyl polyethenoxy ether, acrylic homolog, acrylate and
The mixed solution of a certain amount of methanol (80%-90% of monomer weight ratio);It is added dropwise and is drawn into reaction flask with another constant flow pump
Hair agent aqueous solution drips off after guaranteeing initiator solution;Controlling total time for adding is 1-2 hours, keeps the temperature 2-3h after dripping;
(3), it is cooled to room temperature, being neutralized to pH with aqueous slkali is 7~8, then heats to 110 DEG C or more and steams methanol.
As the further improvement of the preparation method, the chain-transferring agent in step (1) be pentamethyldivinyltriamine and
One of tetramethylethylenediamine, dosage are the 2-5% of monomer gross mass.
Also the initiator solution (mass fraction 4%-6%) as the further improvement of the preparation method, in step (2)
For water-soluble azo V50, dosage is the 2-6% of monomer gross mass.
Also as the further improvement of the preparation method, the alkali in step (3) is in sodium hydroxide, potassium hydroxide and ammonium hydroxide
One kind, dosis neutralisata be carboxyl total mole number 60-100%.
The combed polycarboxylate surfactant of side chain containing polyoxyethylene ether being prepared by adopting the above technical scheme has
Preferable dispersibility, molecular weight is moderate, and to calcium carbonate, the inorganic particles such as aluminum oxide and pesticide have good moisture dispersibility
Can, it additionally can be widely applied to pigment, dyestuff, water-coal-slurry etc..
Compared with prior art, above-mentioned technical proposal has the advantage that
1, the polyacids dipersant structure novel of combed containing polyether lateral chain that the present invention obtains, belongs to novel dispersant;
2, polyoxyethylene ether side chain protrudes into water, can form hydrogen bond with water, form steric barrier, increase steric hindrance, make
Particle separates, and increases the stability of particle;
3, acrylic homolog contains carboxyl, makes particle surface with charge, to generate electric double layer around itself, increases
Add electronic double layer repulsion power, hydrophilic solvent has good adaptability to the pH value of dispersion;
4, using " one kettle way ", preparation process is simple, and operation is easy, efficiently;
5, this preparation method is raw materials used cheap and easy to get, and loss of material is few, and earning rate is high;
6, the combed polycarboxylate salt dispersant provided by the invention containing polyether lateral chain has the suitable degree of polymerization and carboxyl, ester
Base functional group makes dispersing agent have good dispersibility, widely used application prospect by steric hindrance and electrostatic repulsion.
Detailed description of the invention
It elaborates with reference to the accompanying drawing to a specific embodiment of the invention.
Fig. 1 is the infrared spectrum (IR) of dispersing agent made from the embodiment of the present invention 3;Abscissa indicates wave number.3394cm-1Place
For the stretching vibration peak of-OH, 2922cm-1、2871cm-1The respectively stretching vibration peak of methyl and methylene, 1735cm-1It is C=
The stretching vibration peak of O, 1453cm-1Position is the bending vibration of methyl and methylene, 1109cm-1Place is the stretching vibration of C-O-C
Peak, in 2500-2000cm-1No absorption peak, illustrate that double bond disappears substantially, features above shows each monomer successful polymerization.
Fig. 2 be it is produced by the present invention containing polyether lateral chain combed polycarboxylate salt dispersant hydrogen nuclear magnetic resonance spectrogram (1HNMR)。
Abscissa indicates displacement.It is solvent peak at δ=4.80 in nuclear-magnetism figure, is the ethylene oxide structure list in polyethers at δ=3.8-3.47
Member (CH2CH2O), illustrate there is this structure in polymer.δ=0.8-1.58 is-CH on ester group2CH2CH2CH3Proton peak.δ=
1.2 be the proton peak of H in main carbochain.Do not occur the proton peak of double bond after δ=5.7, illustrates that double bond disappears, participate in reaction
Polymerization.
Specific embodiment
The present invention provides a kind of the combed polycarboxylate salt dispersant and preparation method thereof containing polyether lateral chain, combed of the present invention
The monomer ratio used of polycarboxylate salt dispersant is following (mass parts):
4-50 parts of allyl polyethenoxy ether;
1-10 parts of acrylic homolog;
1-10 parts of acrylate.
Synthetic route containing polyoxyethylene ether side chain combed polycarboxylate surfactant is as follows:
Using following preparation step:
(1), chain-transferring agent (4%-6% of monomer mass), water and methanol 1:1 are added in reaction flask and mixes (monomer matter
The 80%-90% of amount), stirring is heated to 90 DEG C or more;
(2), the three kinds of monomers and methanol of certain proportion (mass ratio) preparation are then added dropwise into above-mentioned solution with constant flow pump
The mixed solution of (80%-90% of monomer mass);
(3), initiator solution is added dropwise into reaction flask with another constant flow pump.Controlling time for adding is 1-2 hours, drop
2-3h is kept the temperature after adding;
(4), step (3) acquired solution is cooled to room temperature, being neutralized to pH with aqueous slkali is about 7~8, is then heated to
110 DEG C or more steam methanol.
Below in conjunction with specific embodiment, the present invention is described in detail.Following embodiment will be helpful to the skill of this field
Art personnel further understand the present invention, but the invention is not limited in any way.It should be pointed out that the common skill of this field
For art personnel, without departing from the inventive concept of the premise, various modifications and improvements can be made.These belong to this hair
Bright protection scope.
Embodiment 1:
1), the preparation of surfactant
The chain-transferring agent and a certain amount of water and methanol of 15 parts of addition, stirring, 90 DEG C of heated at constant temperature weigh in reaction flask
500 parts of allyl polyethenoxy ethers, 80 parts of acrylic homologs and 80 parts of acrylate and a certain amount of methanol are in conical flask
In, rate of addition is controlled with constant flow pump, is instilled in four-hole boiling flask;Weigh 20 parts of initiator solutions.Coutroi velocity starts to be added dropwise
Monomer and initiator, control time for adding are 3 hours.2 hours are kept the temperature after being added dropwise.It is cooled to while stirring after heat preservation
Room temperature, being neutralized to pH with sodium hydroxide solution is about 7~8, and dosis neutralisata is the 80% of carboxyl total mole number, then heats to 110
DEG C methanol is steamed, dispersant solution is made.
2), dispersibility of the measurement surfactant to inorganic mineral
Has the distilled water solution of the dispersing agent and 50mL that are added in 0.4g step (1) in plug graduated cylinder to 100mL, to dispersing agent
After dissolution, 1.00g solid particle to be dispersed is added, then plus aqueous solution is to 100mL, it turns upside down in 1 minute 30 times,
180 ° are first overturned, returning in situ is 1 time.Graduated cylinder is vertically disposed in 25 DEG C of thermostatic water-circulator baths, 30min is stood, with suction
Pipe extracts upper layer 90mL suspension out, completes in 15s.It is m that remaining 10mL suspension is transferred to the quality weighed1Drying
In culture dish, and graduated cylinder is rinsed with distilled water solution, it is ensured that the sediment in graduated cylinder is transferred completely into culture dish, by culture dish
80 DEG C of drying in baking oven are put into, weigh m2, calculate the mass M of insoluble matter, M=m2-m1, suspensibility according to the following formula:
Wherein: M be 100mL tool plug graduated cylinder bottom 10mL suspension contained by dispersing agent and solid particle quality (g), 1400
Has the gross mass (g) of contained dispersing agent and solid particle in plug graduated cylinder for 100mL.
By aforesaid operations step, measuring prepared dispersing agent is 96.7% to the suspensibility of calcium carbonate suspension, to three
The suspensibility of Al 2 O suspension is 97.5%.
3), dispersibility of the measurement surfactant to pesticide:
The pesticide suspension concentrate for taking 1g to prepare has in plug graduated cylinder in 250mL, and 250mL standard hard water is added, rocks up and down
30 times, then graduated cylinder is disposed vertically in 25 DEG C of constant temperature water bath, stands half an hour.The upper layer 225mL is extracted with vacuum pump
Liquid, it is m that remaining 25mL suspension, which pours into quality,2In the drying evaporating dish of g, and with distilled water flushing graduated cylinder, it is ensured that sediment
It is transferred completely into culture dish, culture dish is put into 75 DEG C of baking oven, weighing is denoted as m after drying2g.Calculation formula are as follows:
Effective content refers to the content of raw medicine in SC.
By aforesaid operations step, measure prepared dispersing agent be 98.7% to the suspensibility of 43% Tebuconazole SC, it is right
The suspensibility of the imidacloprid SC of 480g/L is 97.4%, is 96.3% to the suspensibility of the imidacloprid SC of 600g/L.
Embodiment 2:
1), the preparation of surfactant
The chain-transferring agent and a certain amount of water and methanol of 28 parts of addition, stirring, 95 DEG C of heated at constant temperature weigh in reaction flask
400 parts of allyl polyethenoxy ethers, 100 parts of acrylic homologs and 100 parts of acrylate and a certain amount of methanol are in conical flask
In, rate of addition is controlled with constant flow pump, is instilled in four-hole boiling flask;Weigh 28 parts of initiator solutions.Coutroi velocity starts to be added dropwise
Monomer and initiator, control time for adding are 1.5 hours.2 hours are kept the temperature after being added dropwise.It is cooled down while stirring after heat preservation
To room temperature, being neutralized to pH with sodium hydroxide solution is about 7~8, and dosis neutralisata is the 70% of carboxyl total mole number, is then heated to
110 DEG C steam methanol, and dispersant solution is made.
By operating procedure described in embodiment 1, measure prepared dispersing agent is to the suspensibility of calcium carbonate suspension
It 97.3%, is 96.9% to the suspensibility of aluminum oxide suspension.To 43% Tebuconazole SC suspensibility be 98.1%, it is right
The suspensibility of the imidacloprid SC of 480g/L is 98.3%, is 97.3% to the suspensibility of the imidacloprid SC of 600g/L.
Embodiment 3:
1), the preparation of surfactant
The chain-transferring agent and a certain amount of water and methanol of 10 parts of addition, stirring, 90 DEG C of heated at constant temperature weigh in reaction flask
350 parts of allyl polyethenoxy ethers, 98 parts of acrylic homologs and 98 parts of acrylate and a certain amount of methanol are in conical flask
In, rate of addition is controlled with constant flow pump, is instilled in four-hole boiling flask;Weigh 22 parts of initiator solutions.Coutroi velocity starts to be added dropwise
Monomer and initiator, control time for adding are 2 hours.1.5 hours are kept the temperature after being added dropwise.It is cooled down while stirring after heat preservation
To room temperature, being neutralized to pH with sodium hydroxide solution is about 7~8, and dosis neutralisata is the 60% of carboxyl total mole number, is then heated to
110 DEG C steam methanol, and dispersant solution is made.
By operating procedure described in embodiment 1, measure prepared dispersing agent is to the suspensibility of calcium carbonate suspension
It 97.8%, is 97.1% to the suspensibility of aluminum oxide suspension.To 43% Tebuconazole SC suspensibility be 98.6%, it is right
The suspensibility of the imidacloprid SC of 480g/L is 97.8%, is 98.1% to the suspensibility of the imidacloprid SC of 600g/L.
Embodiment 4:
1), the preparation of surfactant
The chain-transferring agent and a certain amount of water and methanol of 18 parts of addition, stirring, 98 DEG C of heated at constant temperature weigh in reaction flask
300 parts of allyl polyethenoxy ethers, 100 parts of acrylic homologs and 100 parts of acrylate and a certain amount of methanol are in conical flask
In, rate of addition is controlled with constant flow pump, is instilled in four-hole boiling flask;Weigh 25 parts of initiator solutions.Coutroi velocity starts to be added dropwise
Monomer and initiator, control time for adding are 1 hour.3 hours are kept the temperature after being added dropwise.It is cooled to while stirring after heat preservation
Room temperature, being neutralized to pH with sodium hydroxide solution is about 7~8, and dosis neutralisata is the 90% of carboxyl total mole number, then heats to 110
DEG C methanol is steamed, dispersant solution is made.
By operating procedure described in embodiment 1, measure prepared dispersing agent is to the suspensibility of calcium carbonate suspension
It 96.5%, is 96.7% to the suspensibility of aluminum oxide suspension.To 43% Tebuconazole SC suspensibility be 98.1%, it is right
The suspensibility of the imidacloprid SC of 480g/L is 97.6%, is 97.2% to the suspensibility of the imidacloprid SC of 600g/L.
The present invention relates to the preparations of the polycarboxylate surfactant of the side chain containing polyoxyethylene ether, by graft polyether side
Chain, hydrophobic side chain, neutralize, steam methanol and etc. this kind of surfactant is prepared.Advantages of the present invention are as follows: use " one pot
Method " preparation, preparation method are simple and efficient, and raw materials used cheap and easy to get, loss of material is few, and earning rate is high, and synthetic product structure is new
Grain husk has excellent dispersion performance, has good dispersion performance with the long side chain polycarboxylate of polyoxyethylene ether, works as polycarboxylic acids
It is that high polymer is added in pesticide suspension concentrate, pesticide granules surface is adsorbed on by hydrophobic chain, carboxyl enhances between pesticide granules
Electrostatic repulsion, the oxygen in polyethylene oxide side chains on ehter bond can form hydrogen bond with hydrone, to form hydrophily stereoscopic film,
Wetting, suction-operated are generated in solid liquid interface, to generate peptizaiton to system, there is stronger moisture dispersibility, stabilization
Property and universality, with good application prospect.
Specific embodiments of the present invention are described above.It is to be appreciated that the invention is not limited to above-mentioned
Particular implementation, those skilled in the art can make various deformations or amendments within the scope of the claims, this not shadow
Ring substantive content of the invention.
Claims (8)
1. a kind of combed polycarboxylate salt dispersant containing polyether lateral chain, which is characterized in that by the component mixing of following mass ratio
At:
4-50 parts of allyl polyethenoxy ether;
1-10 parts of acrylic homolog;
1-10 parts of acrylate.
2. the combed polycarboxylate salt dispersant according to claim 1 containing polyether lateral chain, which is characterized in that the poly- carboxylic of the combed
Hydrochlorate dispersing agent is mixed by the component of following mass ratio:
40 parts of allyl polyethenoxy ether;10 parts of acrylic homolog;10 parts of acrylate;
Or, 30 parts of allyl polyethenoxy ether;8 parts of acrylic homolog;5 parts of acrylate.
3. the combed polycarboxylate salt dispersant according to claim 1 containing polyether lateral chain, which is characterized in that the acrylic acid
Homologue is one of acrylic acid and methacrylic acid or a variety of.
4. the combed polycarboxylate salt dispersant according to claim 1 containing polyether lateral chain, which is characterized in that the acrylic acid
Ester is one of methyl acrylate, ethyl acrylate and n-butyl acrylate or a variety of.
5. a kind of preparation method of the combed polycarboxylate salt dispersant containing polyether lateral chain, which is characterized in that use following steps:
(1), chain-transferring agent, water and methanol 1:1 mixing (80%-90% of monomer mass) are added in reaction flask, stirs, heating
To 90 DEG C or more;
(2), then with constant flow pump is added dropwise into above-mentioned solution certain proportion prepare three kinds of monomers and methanol (monomer mass
Mixed solution 80%-90%);
(3), the initiator solution that mass fraction is 4%-6% is added dropwise into reaction flask with another constant flow pump;The total drop of control
It is 1-2 hours between added-time, keeps the temperature 2-3h after dripping;
(4), step (3) acquired solution is cooled to room temperature, being neutralized to pH with aqueous slkali is about 7~8, then heats to 110 DEG C
Methanol is steamed above.
6. the preparation method of the combed polycarboxylate salt dispersant according to claim 5 containing polyether lateral chain, which is characterized in that
Chain-transferring agent in step (1) is one of pentamethyldivinyltriamine and tetramethylethylenediamine, and dosage is that monomer is total
The 2-5% of quality.
7. the preparation method of the combed polycarboxylate salt dispersant according to claim 5 containing polyether lateral chain, which is characterized in that
The aqueous solution that initiator solution in step (3) is water-soluble azo V50, dosage are the 2-6% of monomer gross mass.
8. the preparation method of the combed polycarboxylate salt dispersant according to claim 5 containing polyether lateral chain, which is characterized in that
Alkali in step (4) is one of sodium hydroxide, potassium hydroxide and ammonium hydroxide, and dosis neutralisata is the 60- of carboxyl total mole number
100%.
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Application publication date: 20191029 |