CN113121763A - Acrylate comb dispersant, organic pigment color paste and preparation method thereof - Google Patents

Acrylate comb dispersant, organic pigment color paste and preparation method thereof Download PDF

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Publication number
CN113121763A
CN113121763A CN202110261614.5A CN202110261614A CN113121763A CN 113121763 A CN113121763 A CN 113121763A CN 202110261614 A CN202110261614 A CN 202110261614A CN 113121763 A CN113121763 A CN 113121763A
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China
Prior art keywords
acrylate
organic pigment
aromatic
comb
dispersant
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Chinese (zh)
Inventor
张云杰
李鑫
魏国静
赵秀蓉
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Zhuhai Zhongmo Technology Co ltd
TRENDVISION ELECTRONICS SCIENCE TECHNOLOGY (ZHUHAI) CO LTD
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Zhuhai Zhongmo Technology Co ltd
TRENDVISION ELECTRONICS SCIENCE TECHNOLOGY (ZHUHAI) CO LTD
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Priority to CN202110261614.5A priority Critical patent/CN113121763A/en
Publication of CN113121763A publication Critical patent/CN113121763A/en
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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
    • C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/32—Inkjet printing inks characterised by colouring agents
    • C09D11/322—Pigment inks
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D17/00—Pigment pastes, e.g. for mixing in paints
    • C09D17/001—Pigment pastes, e.g. for mixing in paints in aqueous medium
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D17/00—Pigment pastes, e.g. for mixing in paints
    • C09D17/003—Pigment pastes, e.g. for mixing in paints containing an organic pigment

Abstract

The invention belongs to the technical field of ink-jet ink, and discloses an acrylate comb dispersant, an organic pigment color paste and a preparation method thereof. The dispersing agent comprises A, B parts, wherein the A part consists of an aromatic acrylate structural unit and a non-aromatic lipophilic acrylate structural unit, and the B part consists of a hydrophilic acrylate structural unit; the mass ratio of the aromatic acrylate structural unit to the non-aromatic lipophilic acrylate structural unit is 1 (0.5-1.5). The acrylate comb-shaped object dispersant provided by the invention can enable the organic pigment to be stably dispersed in water, and the organic pigment color paste prepared by using the acrylate comb-shaped object dispersant has strong stability and low viscosity, and is not easy to generate sedimentation and flocculation.

Description

Acrylate comb dispersant, organic pigment color paste and preparation method thereof
Technical Field
The invention belongs to the technical field of ink-jet ink, and particularly relates to an acrylate comb dispersant, organic pigment color paste and a preparation method thereof.
Background
The ink-jet technology has high requirement on the stability of pigment ink, needs the ink not to block a spray head, does not generate ink inclined spray, has good printing fluency, is storage-resistant, and can be stored for at least one year without flocculation, delamination, obvious coarseness and other phenomena. The key to the high stability of pigment inks is the dispersant, which can stably disperse the organic pigment in the liquid, not only needs to separate the organic pigment particles, but also needs to form steric hindrance to prevent the particles from flocculating.
The common dispersant is straight-chain, the chain length of the dispersant is difficult to control, stable steric hindrance is difficult to form between organic pigment particles, phenomena such as precipitation, flocculation and the like are easy to occur, and the requirements of the ink-jet color paste cannot be met.
Therefore, it is desired to provide a dispersant capable of stably dispersing an organic pigment in water without causing precipitation and flocculation.
Disclosure of Invention
The present invention is directed to solving at least one of the problems of the prior art described above. Therefore, the invention provides an acrylate comb-shaped matter dispersing agent which can form stable steric hindrance between organic pigment particles, so that the organic pigment is stably dispersed in water without precipitation and flocculation.
The invention conception is as follows: the inventors have found in the previous studies that an acrylate comb-like dispersant composed of a hydrophilic oligomer (comb teeth) and a lipophilic oligomer (comb handle) has good dispersibility and can disperse inorganic pigments such as titanium dioxide, but cannot disperse organic pigments. Through continuous research, the inventor surprisingly finds that the organic pigment can be effectively dispersed by skillfully introducing aromatic groups into the comb-shaped dispersing agent for dispersing the inorganic pigment and matching the aromatic acrylate structure with the nonaromatic lipophilic acrylate structure.
An acrylate comb dispersant comprises a part A and a part B, wherein the part A is composed of an aromatic acrylate structural unit and a non-aromatic lipophilic acrylate structural unit, and the part B is composed of a hydrophilic acrylate structural unit; the mass ratio of the aromatic acrylate structural unit to the non-aromatic lipophilic acrylate structural unit is 1: (0.5-1.5).
In the acrylate comb-shaped matter dispersing agent, a part consisting of the aromatic acrylate structural unit and the nonaromatic lipophilic acrylate structural unit forms a comb handle which can be adsorbed on the surface of an organic pigment; the ratio of the aromatic acrylate structural unit to the nonaromatic lipophilic acrylate structural unit is controlled, so that the dispersing agent and the organic pigment are tightly adsorbed and combined; and the part consisting of hydrophilic acrylate structural units forms comb teeth and is completely unfolded in water.
Because the chemical chain segment of the aromatic group can not rotate, the aromatic group on the dispersing agent can not contact with the aromatic group on the organic pigment and can be well adsorbed, so that the adsorption capacity of the dispersing agent is reduced; and the chemical chain segment of the aliphatic group can rotate, so that the flexibility of the dispersant molecule is enhanced, and the deficiency of the aromatic group is just made up. It is also important to control the ratio of aromatic groups to aliphatic groups, and too many aromatic groups will result in insufficient rotation of the chemical segment, reducing the chance of adsorption of the dispersant to the organic pigment. Too few aromatic groups and insufficient adsorption groups cause insufficient adsorption of the dispersing agent and the organic pigment.
Preferably, the mass ratio of the aromatic acrylate structural unit to the non-aromatic lipophilic acrylate structural unit is 1 (0.8-1.2); preferably, the mass ratio of the aromatic acrylate structural unit to the non-aromatic lipophilic acrylate structural unit is 1 (1-1.2).
Preferably, the molecular weight of the B moiety is 2000-3000; the molecular weight of the acrylate comb dispersant is 20000-30000. Further preferably, the molecular weight of the moiety B is 2200-3000; the molecular weight of the acrylate comb dispersant is 22000-30000. The acrylate comb dispersant enables the organic pigment to be stably dispersed in water by controlling the molecular weight thereof so that it forms appropriate steric hindrance between the organic pigment particles.
Preferably, the aromatic acrylate structural unit comprises one or two benzene ring structures.
Preferably, the hydrophilic acrylate structural unit contains a hydroxyl group and/or a hydroxyl group.
The invention also provides a preparation method of the acrylate comb dispersant, which comprises the following steps:
(1) mixing a hydrophilic acrylate monomer, a chain transfer agent and a second solvent, then adding a second initiator, reacting, and then adding an end-capping agent to prepare a hydrophilic polymer;
(2) mixing an aromatic acrylate monomer, a non-aromatic lipophilic acrylate monomer, the hydrophilic polymer prepared in the step (1) and a first solvent, then adding a first initiator, and reacting to prepare the acrylate comb-shaped matter dispersing agent.
Preferably, the step (1), the step (2) and the reaction temperature are all 5-10 ℃ below the boiling point of the solvent used.
Preferably, the hydrophilic acrylate monomer in step (1) is at least one of acrylic acid, methacrylic acid or hydroxyethyl methacrylate.
Preferably, the aromatic acrylate monomer in step (2) is at least one selected from ethoxyphenol acrylate, 2-phenoxyethyl methacrylate, methyl benzyl acrylate or o-phenylphenoxyethyl acrylate. The aromatic acrylate monomer containing one or two benzene ring structures is adopted, so that the prepared dispersing agent can be adsorbed on organic pigment particles, and the steric hindrance cannot be influenced by the excessively strong adsorption formed by excessive benzene ring structures.
Preferably, the non-aromatic lipophilic acrylate monomer in step (2) is at least one selected from the group consisting of dimethyl methacrylate, ethoxytriethylene glycol methacrylate, isobornyl methacrylate, 1, 6-hexanediol diacrylate, 1, 4-butanediol diacrylate, dipropylene glycol diacrylate, n-butyl acrylate, methyl acrylate and methyl methacrylate.
Preferably, the chain transfer agent in step (1) comprises at least one of aliphatic thiol, carbon tetrachloride, dithioester, iodoform, 1-chloro-1-iodoalkane, 2, 4-diphenyl-4-methyl-1-pentene or isooctyl 3-mercaptopropionate.
Preferably, the blocking agent in step (1) is selected from at least one of hexamethylene diisocyanate, tert-butyl peroxy (2-ethyl acetate) or methyl ethyl ketone oxime.
Preferably, the first initiator and the second initiator are independently selected from at least one of azobisisobutyrimidazole hydrochloride, azobisisoheptonitrile, azobisisobutyronitrile, azobisisovaleronitrile, azobisdicyclohexylcarbonitrile, methyl azobisisobutyrate, azobiscyanovaleric acid, or azobisisobutyrocarboxamide.
Preferably, the first solvent and the second solvent independently comprise at least one of ethanol, n-propanol, isopropanol, butanone, methyl isobutyl ketone, ethyl acetate, ethyl ester isopropyl ester, dichloromethane, acetone, dichloroethane, toluene, xylene, tetrahydrofuran, or cyclohexanone.
Preferably, the preparation method of the acrylate comb dispersant comprises the following steps:
(1) mixing 25-50 parts of hydrophilic acrylate monomer, 0.1-1 part of chain transfer agent and 50-70 parts of second solvent, then adding 0.1-1 part of second initiator, reacting, and then adding 0.1-1 part of end capping agent to prepare hydrophilic polymer;
(2) mixing 10-30 parts of aromatic acrylate monomer, 20-40 parts of non-aromatic lipophilic acrylate monomer, 20-50 parts of the hydrophilic polymer prepared in the step (1) and 10-30 parts of first solvent, then adding 0.1-1 part of first initiator, and reacting to prepare the acrylate comb-shaped material dispersing agent.
The invention also provides application of the acrylate comb-shaped object dispersing agent in preparation of organic pigment color paste.
The invention also provides organic pigment color paste which comprises the following components in parts by weight: the acrylate comb dispersant, organic pigment and water.
Preferentially, the organic pigment color paste also comprises a neutralizer; the neutralizing agent is at least one selected from sodium hydroxide, potassium hydroxide, monoethanolamine, diethanolamine, triethanolamine, N-methyldiethanolamine, N-ethyldiethanolamine, N-propyldiethanolamine or N-butyldiethanolamine. The neutralizer modifies the lipophilic part of the dispersant into hydrophilic, so that the dispersant can be stably dispersed in the water-phase color paste.
Preferably, the organic pigment color paste comprises the following components in parts by weight; 10-30 parts of acrylate comb dispersing agent, 10-40 parts of organic pigment, 1-5 parts of neutralizing agent and 20-80 parts of water.
The organic pigments include, but are not limited to, pigment yellow No. 74, pigment red No. 122, pigment blue 15: no. 3, pigment black No. 7.
The invention also provides a preparation method of the organic pigment color paste, which comprises the following steps:
(1) mixing a neutralizing agent, the acrylate comb-shaped matter dispersing agent and water, then adding an organic pigment, and mixing to obtain a pre-dispersion liquid;
(2) and (2) grinding the pre-dispersion liquid prepared in the step (1), filtering, and taking filtrate to obtain the organic pigment color paste.
An ink comprises the organic pigment color paste.
Compared with the prior art, the invention has the following beneficial effects:
the acrylate comb-shaped matter dispersing agent provided by the invention forms a comb handle by a part consisting of an aromatic acrylate structural unit and a non-aromatic lipophilic acrylate structural unit, is adsorbed on the surface of organic pigment and is tightly combined with the organic pigment; and the part consisting of hydrophilic acrylate structural units forms comb teeth, and the comb teeth are completely unfolded in water, so that steric hindrance is formed among organic pigment particles. The acrylate comb-shaped object dispersant provided by the invention can enable the organic pigment to be stably dispersed in water, and the organic pigment color paste prepared by using the acrylate comb-shaped object dispersant has strong stability and low viscosity, and is not easy to generate sedimentation and flocculation.
Detailed Description
In order to make the technical solutions of the present invention more apparent to those skilled in the art, the following examples are given for illustration. It should be noted that the following examples are not intended to limit the scope of the claimed invention.
The starting materials, reagents or apparatuses used in the following examples are conventionally commercially available or can be obtained by conventionally known methods, unless otherwise specified.
Example 1
A preparation method of the dispersing agent comprises the following steps:
(1) in a dry clean four-neck flask provided with a stirring and condensing reflux device, firstly introducing nitrogen for 10 minutes, pouring 50g of butanone, 100g of ethanol, 50g of acrylic acid, 50g of hydroxyethyl methacrylate and 5g of dodecyl sulfuric acid into the four-neck flask in sequence, uniformly stirring and heating, and controlling the temperature at 72 ℃.
(2) 3g of azodiisoheptanonitrile and 40g of butanone are mixed and stirred, the mixture is added into a four-neck flask in a slow dropwise manner, the adding time is 90 minutes, the temperature is maintained at 72 ℃, and the stirring is continued for 120 minutes after the adding is finished and the temperature is maintained at 72 ℃.
(3) Mixing and stirring 7g of hexamethylene diisocyanate and 60g of butanone, adding the mixture into a reaction kettle in a slow dropwise manner for 60 minutes, maintaining the temperature at 72 ℃ after the addition, and continuing stirring for 60 minutes to obtain 350g of hydrophilic acrylate oligomer.
(4) In a dry clean four-neck flask provided with a stirring and condensing reflux device, nitrogen is firstly introduced for 10 minutes, and 50g of ethanol, 100g of ethoxyphenol acrylate and 200g of methyl methacrylate are sequentially poured into a reaction kettle to be uniformly stirred and heated, and the temperature is controlled at 77 ℃.
(5) 350g of hydrophilic acrylate oligomer and 100g of ethanol are mixed and stirred, 5g of azobisisoheptonitrile and 50g of butanone are mixed, the two solutions are injected into the reaction kettle in the step (4) in a cocurrent mode, the adding time is 180 minutes, the temperature is maintained at 72 ℃ after the adding, the stirring is continued for 60 minutes, and 1840 g of the comb dispersant can be obtained.
Example 2
(1) In a dry clean four-neck flask equipped with a stirring and condensing reflux device, nitrogen is firstly introduced for 10 minutes, and 50g of isopropanol, 100g of ethanol, 50g of methacrylic acid, 50g of hydroxyethyl methacrylate and 5g of dithioester (CPDB) are poured into the four-neck flask in sequence, uniformly stirred and heated, and the temperature is controlled at 75 ℃.
(2) 3g of azobisisobutyronitrile and 40g of butanone are mixed and stirred, added into a four-neck flask in a slow dropwise manner for 90 minutes, the temperature is maintained at 75 ℃, and the mixture is continuously stirred for 120 minutes after the addition, the temperature is maintained at 75 ℃.
(3) 7g of tert-butyl peroxy (2-ethylhexanoate) and 60g of butanone are mixed and stirred, the mixture is added into a reaction kettle in a slow dropwise manner for 60 minutes, the temperature is maintained at 75 ℃, and the stirring is continued for 60 minutes after the addition, so that 350g of hydrophilic acrylate oligomer can be obtained.
(4) In a dry clean four-neck flask provided with a stirring and condensing reflux device, nitrogen is firstly introduced for 10 minutes, and 50g of isopropanol, 100g of 2-phenoxyethyl methacrylate and 200g of dimethyl methacrylate are sequentially poured into a reaction kettle to be uniformly stirred and heated, and the temperature is controlled at 75 ℃.
(5) 350g of hydrophilic acrylate oligomer and 100g of ethanol are mixed and stirred, 5g of azobisisobutyronitrile and 50g of butanone are mixed, the two solutions are injected into the reaction kettle in the step (4) in a cocurrent flow mode, the adding time is 180 minutes, the temperature is maintained at 75 ℃ after the adding, the stirring is continued for 60 minutes, and 2840 g of the comb-shaped object dispersing agent can be obtained.
Example 3
(1) In a dry clean four-neck flask provided with a stirring and condensing reflux device, firstly introducing nitrogen for 10 minutes, pouring 50g of butanone, 100g of isopropanol, 50g of acrylic acid and 50g of methacrylate and 5g of 2, 4-diphenyl-4-methyl-1-pentene into the four-neck flask in sequence, uniformly stirring and heating, and controlling the temperature at 72 ℃.
(2) 3g of azobisisovaleronitrile and 40g of butanone are mixed and stirred, the mixture is added into a four-neck flask in a slow dropwise manner, the adding time is 90 minutes, the temperature is maintained at 72 ℃, and the stirring is continued for 120 minutes after the adding is finished and the temperature is maintained at 72 ℃.
(3) And mixing and stirring 7g of methyl ethyl ketoxime and 60g of butanone, adding the mixture into a reaction kettle in a slow dropwise manner for 60 minutes, maintaining the temperature at 72 ℃, and maintaining the temperature at 72 ℃ after the addition and continuing stirring for 60 minutes to obtain 350g of hydrophilic acrylate oligomer.
(4) In a dry clean four-neck flask provided with a stirring and condensing reflux device, nitrogen is firstly introduced for 10 minutes, and 50g of isopropanol, 100g of methyl benzyl acrylate and 200g of n-butyl acrylate are poured into a reaction kettle in sequence, uniformly stirred and heated, and the temperature is controlled at 77 ℃.
(5) 350g of hydrophilic acrylate oligomer and 100g of isopropanol are mixed and stirred, 5g of azobisisovaleronitrile and 50g of butanone are mixed, the two solutions are injected into the reaction kettle of the step (4) in a parallel flow mode in the same amount, the adding time is 180 minutes, the temperature is maintained at 72 ℃ after the adding, the stirring is continued for 60 minutes, and 3840 g of the comb-shaped object dispersing agent can be obtained.
Example 4
(1) In a dry clean four-neck flask provided with a stirring and condensing reflux device, firstly introducing nitrogen for 10 minutes, pouring 50g of butanone, 100g of n-propanol, 150g of methacrylic acid and 5g of 3-mercaptopropionic acid isobutyl ester (IDMP) into the four-neck flask in sequence, uniformly stirring and heating, and controlling the temperature at 75 ℃.
(2) 3g of azodicyclohexyl formonitrile and 40g of butanone are mixed and stirred, the mixture is added into a four-neck flask in a slow dropwise adding mode, the adding time is 90 minutes, the temperature is maintained at 72 ℃, and after the adding, the temperature is maintained at 75 ℃ and the stirring is continued for 120 minutes.
(3) Mixing and stirring 7g of hexamethylene diisocyanate and 60g of butanone, adding the mixture into a reaction kettle in a slow dropwise manner for 60 minutes, maintaining the temperature at 75 ℃ after the addition, and continuing stirring for 60 minutes to obtain 350g of hydrophilic acrylate oligomer.
(4) In a dry clean four-neck flask provided with a stirring and condensing reflux device, nitrogen is firstly introduced for 10 minutes, and 50g of n-propanol, 100g of o-phenylphenoxyethyl acrylate and 200g of methyl acrylate are poured into a reaction kettle to be uniformly stirred and heated, and the temperature is controlled at 77 ℃.
(5) 350g of hydrophilic acrylate oligomer and 100g of n-propanol are mixed and stirred, 5g of azodicyclohexyl formonitrile and 50g of butanone are mixed, the two solutions are injected into the reaction kettle of the step (4) in a parallel flow mode in the same amount, the adding time is 180 minutes, the temperature is maintained at 72 ℃ after the adding, the stirring is continued for 60 minutes, and 3840 g of the comb-shaped object dispersing agent can be obtained.
Application example 1
The preparation method of the color paste comprises the following steps:
(1) 12g of sodium hydroxide and 236g of deionized water were dissolved by stirring, and 72g of the dispersant prepared in example 1 was further added and dissolved by stirring.
(2) 80g of pigment yellow 74 is added into the solution in the step (1), and the mixture is stirred for 60 minutes to completely wet the pigment, so that a pre-dispersion liquid can be obtained.
(3) And (3) grinding the pre-dispersion liquid in a sand mill until the particle size of D50 of the toner reaches 100 nanometers, and filtering to remove large particles and colloid to obtain 400g of stable pigment yellow 74 color paste.
Application example 2
The preparation method of the color paste comprises the following steps:
(1) 12g of sodium hydroxide and 236g of deionized water were dissolved by stirring, and 72g of the dispersant prepared in example 2 was further added and dissolved by stirring.
(2) 80g of pigment Red No. 122 is added into the solution of step (1), and the mixture is stirred for 60 minutes to completely wet the pigment, so that a pre-dispersion liquid can be obtained.
(3) And (3) grinding the pre-dispersion liquid in a sand mill until the particle size of D50 of the toner reaches 100 nanometers, and filtering to remove large particles and colloid to obtain 400g of stable pigment red 122 color paste.
Application example 3
The preparation method of the color paste comprises the following steps:
(1) 12g of sodium hydroxide and 236g of deionized water were dissolved by stirring, and 72g of the dispersant prepared in example 3 was further added and dissolved by stirring.
(2) 80g of pigment blue 15: adding No. 3 into the solution in the step (1), and stirring for 60 minutes to completely wet the pigment to obtain a pre-dispersion liquid.
(3) And (3) grinding the pre-dispersion liquid in a sand mill until the particle size of D50 of the toner reaches 100 nanometers, and filtering to remove large particles and colloid to obtain the stable pigment blue 15: and 400g of 3 color paste.
Application example 4
The preparation method of the color paste comprises the following steps:
(1) 12g of sodium hydroxide and 236g of deionized water were dissolved by stirring, and 72g of the dispersant prepared in example 4 was further added and dissolved by stirring.
(2) 80g of pigment Black No. 7 is added into the solution in the step (1), and the mixture is stirred for 60 minutes to completely wet the pigment, so that a pre-dispersion liquid can be obtained.
(3) And (3) grinding the pre-dispersion liquid in a sand mill until the particle size of D50 of the toner reaches 100 nanometers, and filtering to remove large particles and colloid to obtain 400g of stable pigment black 7 color paste.
Comparative example 1
(1) 72g of dispersant DISPERBYK-190 (dispersant DISPERBYK-190 is a high-market-occupation aqueous organic pigment dispersant and has high representativeness) and 248g of deionized water are taken and stirred to be dissolved, so as to obtain solution.
(2) Adding 80g of pigment yellow 74 into the solution prepared in the step (1), and stirring for 60 minutes to completely wet the pigment to obtain a pre-dispersion liquid.
(3) And (3) grinding the pre-dispersion liquid in a sand mill until the particle size of D50 of the toner reaches 100 nanometers, and filtering to remove large particles and colloid to obtain 400g of stable pigment yellow 74 color paste.
Comparative example 2
(1) 72g of comb dispersing agent prepared in patent 202010030757.0 example 2 and 248g of deionized water are taken and stirred to be dissolved to obtain solution.
(2) Adding 80g of pigment yellow 74 into the solution prepared in the step (1), and stirring for 60 minutes to completely wet the pigment to obtain a pre-dispersion liquid.
(3) And (3) grinding the pre-dispersion liquid in a sand mill until the particle size of D50 of the toner reaches 100 nanometers, and filtering to remove large particles and colloid to obtain 400g of stable pigment yellow 74 color paste.
Comparative example 3
(1) Taking DISPERBYK-19072 g of dispersant and 248g of deionized water, stirring and dissolving to obtain a solution.
(2) 80g of pigment Red No. 122 was added to the solution obtained in step (1), and stirred for 60 minutes to completely wet the colorant, thereby obtaining a predispersion.
(3) And (3) grinding the pre-dispersion liquid in a sand mill until the particle size of D50 of the toner reaches 100 nanometers, and filtering to remove large particles and colloid to obtain 400g of stable pigment red 122 color paste.
Comparative example 4
(1) 72g of comb dispersing agent prepared in patent 202010030757.0 example 2 and 248g of deionized water are taken and stirred to be dissolved to obtain solution.
(2) 80g of pigment Red No. 122 was added to the solution obtained in step (1), and stirred for 60 minutes to completely wet the colorant, thereby obtaining a predispersion.
(3) And (3) grinding the pre-dispersion liquid in a sand mill until the particle size of D50 of the toner reaches 100 nanometers, and filtering to remove large particles and colloid to obtain 400g of stable pigment red 122 color paste.
Comparative example 5
(1) Taking DISPERBYK-19072 g of dispersant and 248g of deionized water, stirring and dissolving to obtain a solution.
(2) 80g of pigment blue 15: adding No. 3 into the solution prepared in the step (1), and stirring for 60 minutes to completely wet the pigment to obtain a pre-dispersion liquid.
(3) And (3) grinding the pre-dispersion liquid in a sand mill until the particle size of D50 of the toner reaches 100 nanometers, and filtering to remove large particles and colloid to obtain the stable pigment blue 15: 400g of No. 3 color paste.
Comparative example 6
(1) 72g of comb dispersing agent prepared in patent 202010030757.0 example 2 and 248g of deionized water are taken and stirred to be dissolved to obtain solution.
(2) 80g of pigment blue 15: adding No. 3 into the solution prepared in the step (1), and stirring for 60 minutes to completely wet the pigment to obtain a pre-dispersion liquid.
(3) And (3) grinding the pre-dispersion liquid in a sand mill until the particle size of D50 of the toner reaches 100 nanometers, and filtering to remove large particles and colloid to obtain the stable pigment blue 15: 400g of No. 3 color paste.
Comparative example 7
(1) Taking DISPERBYK-19072 g of dispersant and 248g of deionized water, stirring and dissolving to obtain a solution.
(2) 80g of pigment Black No. 7 is added into the solution prepared in the step (1), and the mixture is stirred for 60 minutes to completely wet the pigment, so that a pre-dispersion liquid can be obtained.
(3) And (3) grinding the pre-dispersion liquid in a sand mill until the particle size of D50 of the toner reaches 100 nanometers, and filtering to remove large particles and colloid to obtain 400g of stable pigment black No. 7 color paste.
Comparative example 8
(1) 72g of comb dispersing agent prepared in patent 202010030757.0 example 2 and 248g of deionized water are taken and stirred to be dissolved to obtain solution.
(2) 80g of pigment Black No. 7 is added into the solution prepared in the step (1), and the mixture is stirred for 60 minutes to completely wet the pigment, so that a pre-dispersion liquid can be obtained.
(3) And (3) grinding the pre-dispersion liquid in a sand mill until the particle size of D50 of the toner reaches 100 nanometers, and filtering to remove large particles and colloid to obtain 400g of stable pigment black No. 7 color paste.
Product effectiveness testing
And (3) detecting the molecular weight: the molecular weights of the hydrophilic oligomer prepared in examples 1 to 4 and the comb dispersant were measured by Shimadzu gel permeation chromatography LC-20 AD.
And (3) viscosity detection: the viscosities of the organic pigment ink-jet pastes prepared in application examples 1 to 4 and comparative examples 1 to 8 were measured using a Bohler fly (Brookfield) Wells cone and plate viscometer.
And (3) particle size detection: the particle sizes of the organic pigment ink-jet color pastes prepared in the application examples 1-4 and the comparative examples 1-8 are detected, and a Malvern (Malvern) Nano S90 nanometer particle size instrument is adopted as a detection instrument.
And (3) stability testing: and aging the organic pigment ink-jet color paste prepared in the application examples 1-4 and the comparative examples 1-8 at 60 ℃ for 7 days, wherein the particle size change is less than 10 percent and the viscosity change is less than 5 percent, judging the color paste to be qualified, otherwise, judging the color paste to be unqualified.
And (3) testing filterability: detecting the viscosity of the organic pigment ink-jet color paste prepared in the application examples 1-4 and the comparative examples 1-8, and judging the color paste to be qualified within 5min/500g by adopting a Minipore PVDF1.0 micron filter membrane; otherwise, the judgment is unqualified.
The test results are shown in tables 1 to 5
Table 1 shows the results of molecular weight measurements of the hydrophilic oligomers and comb dispersants prepared in examples 1-4.
TABLE 1
Figure BDA0002970275280000101
Table 2 shows the performance test results of the pigment yellow 74 ink-jet pastes prepared in application example 1, comparative example 1 and comparative example 2.
TABLE 2
Figure BDA0002970275280000102
Figure BDA0002970275280000111
Table 3 shows the results of performance tests of pigment Red 122 # ink-jet pastes prepared in application example 2, comparative example 3 and comparative example 4.
TABLE 3
Figure BDA0002970275280000112
Table 4 shows pigment blue 15 prepared in example 3, comparative example 5, and comparative example 6: and (3) a performance test result of the ink-jet color paste.
TABLE 4
Figure BDA0002970275280000113
Figure BDA0002970275280000121
Table 5 shows the results of performance tests of the pigment Black No. 7 ink-jet pastes prepared in example 4, comparative example 7 and comparative example 8.
TABLE 5
Figure BDA0002970275280000122
From the test results in tables 2, 3, 4 and 5, it can be seen that the organic pigment inkjet pastes prepared using the comb dispersants provided by the present invention, no matter the D50 particle size before milling time and aging, are superior to the dispersants of DISPERBYK-190 and patent 202010030757.0, and the comb dispersants provided by the present invention have superior milling efficiency on organic pigments. In addition, the physical property change of the color paste after aging for 7 days is better than that of DISPERBYK-190 and the dispersant of patent 202010030757.0, which shows that the comb dispersant provided by the invention can form stable steric hindrance between organic pigment particles, so that the organic pigment is stably dispersed in water without precipitation and flocculation, and the prepared organic pigment color paste and the prepared ink-jet ink have high quality.

Claims (10)

1. An acrylate comb dispersant, which is characterized by comprising a part A and a part B, wherein the part A is composed of an aromatic acrylate structural unit and a non-aromatic lipophilic acrylate structural unit, and the part B is composed of a hydrophilic acrylate structural unit;
the mass ratio of the aromatic acrylate structural unit to the non-aromatic lipophilic acrylate structural unit is 1 (0.5-1.5).
2. The acrylate comb dispersant according to claim 1, characterized in that the mass ratio of the aromatic acrylate structural units and the non-aromatic lipophilic acrylate structural units is 1 (0.8-1.2).
3. The acrylate comb dispersant according to claim 1, characterized in that the molecular weight of said B moiety is 2000-3000; the molecular weight of the acrylate comb dispersant is 20000-30000.
4. A method of preparing the acrylate comb dispersant of any of claims 1 to 3, characterized by comprising the steps of:
(1) mixing a hydrophilic acrylate monomer, a chain transfer agent and a second solvent, then adding a second initiator, reacting, and then adding an end-capping agent to prepare a hydrophilic polymer;
(2) mixing an aromatic acrylate monomer, a non-aromatic lipophilic acrylate monomer, the hydrophilic polymer prepared in the step (1) and a first solvent, then adding a first initiator, and reacting to prepare the acrylate comb-shaped matter dispersing agent.
5. The method according to claim 4, wherein the hydrophilic acrylate monomer in step (1) is at least one of acrylic acid, methacrylic acid, or hydroxyethyl methacrylate.
6. The method according to claim 4, wherein the aromatic acrylate monomer in the step (2) is at least one selected from the group consisting of ethoxyphenol acrylate, 2-phenoxyethyl methacrylate, methyl benzyl acrylate and o-phenylphenoxyethyl acrylate.
7. The organic pigment color paste is characterized by comprising the following components: the acrylate comb dispersant of any one of claims 1 to 3, an organic pigment and water.
8. The organic pigment paste according to claim 7, further comprising a neutralizer; the neutralizing agent is at least one selected from sodium hydroxide, potassium hydroxide, monoethanolamine, diethanolamine, triethanolamine, N-methyldiethanolamine, N-ethyldiethanolamine, N-propyldiethanolamine or N-butyldiethanolamine.
9. The preparation method of the organic pigment color paste according to claim 8, which is characterized by comprising the following steps:
(1) mixing a neutralizing agent, the acrylate comb dispersant of any one of claims 1-3 and water, then adding an organic pigment, and mixing to obtain a pre-dispersion;
(2) and (2) grinding the pre-dispersion liquid prepared in the step (1), filtering, and taking filtrate to obtain the organic pigment color paste.
10. An ink comprising the organic pigment paste according to claim 7 or 8.
CN202110261614.5A 2021-03-10 2021-03-10 Acrylate comb dispersant, organic pigment color paste and preparation method thereof Pending CN113121763A (en)

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