CN113278324B - Preparation method and application of modifying agent of azo organic pigment water-based ink - Google Patents
Preparation method and application of modifying agent of azo organic pigment water-based ink Download PDFInfo
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- CN113278324B CN113278324B CN202110610349.7A CN202110610349A CN113278324B CN 113278324 B CN113278324 B CN 113278324B CN 202110610349 A CN202110610349 A CN 202110610349A CN 113278324 B CN113278324 B CN 113278324B
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- 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
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
- C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/74—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by halogenation, hydrohalogenation, dehalogenation, or dehydrohalogenation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
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- 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
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
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- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
The invention provides a preparation method and application of a modifier of azo organic pigment water-based ink. The preparation method provided by the invention aims at the water-based ink, can reduce the viscosity and simultaneously improve the stability according to the requirement of the pigment content of the water-based ink, is beneficial to the storage and transportation of the azo organic pigment water-based ink, and has a good market application prospect.
Description
Technical Field
The invention belongs to the field of preparation of high molecular compounds by using carbon-carbon unsaturated bonds, and relates to a preparation method and application of a modifier of azo organic pigment water-based ink.
Background
Azo organic pigments generally require an organic solvent to fully wet and disperse the pigment, and are uniformly dispersed with polymer resins and organic pigments to prepare a desired color dispersion, and then the color dispersion is applied to various printing forms. In recent years, with the enhancement of environmental awareness, more and more alternatives to organic solvents have been created during the use of pigments, and non-toxicity, non-odor, and non-irritation have become a trend. The substitution of water as a cheap organic solvent is the subject of intensive research in the current pigment application field, and the application of pigment aqueous systems is rapidly developing due to the constant innovation and development of technology. Generally, the pigment content in the aqueous ink is 5 to 30% when applied. Due to the need for cost savings, aqueous ink manufacturers are continually seeking to produce aqueous base inks having higher pigment content that can be used when diluted to the desired printing consistency by the addition of water before use by the customer. The pigment content of the aqueous base ink is generally 30 to 50%, and the viscosity and viscosity stability of the aqueous base ink are critical factors for smooth use.
For example, chinese patent application CN104497695A discloses an aqueous coating ink added with a dendritic polymer dispersant, which comprises the following components by weight: 1-3 parts of dendritic polymer, 80-150 parts of water-based resin, 8-12 parts of toner and 11-22 parts of solvent. The invention achieves the following beneficial effects: 1. the method has the advantages of industrial production, simple process and batch popularization; 2. the performance of the coating can be improved, the process effect is improved, and the mechanical properties such as the adhesive force, the flexibility, the hardness, the wear resistance and the like of the coating are not reduced; 3. the dendritic dispersing agent has the advantages that the organic pigment dispersing agent is universal for azo organic pigments, quinacridone organic pigments and the like, compared with the traditional dispersing agent, the dendritic dispersing agent has obvious advantages in final evaluation index viscosity and fineness compared with the traditional dispersing agent, the addition amount of the dendritic dispersing agent is less than that of the traditional dispersing agent, the overall advantages are obvious, and the purposes of saving cost and improving process effects can be achieved. However, the dispersant of the present invention is applicable only to aqueous inks, and the viscosity reducing effect of aqueous base inks having a higher pigment content is neither mentioned nor expected.
The popularization and application of the water-based ink put higher requirements on the viscosity reduction and stability improvement of the ink by the modifier. In the current research on the aqueous pigment ink modifier, no modifier is proposed specifically for aqueous base ink, and no modifier is proposed that is effective in improving the viscosity and viscosity stability of aqueous base ink.
Disclosure of Invention
The invention provides a preparation method and application of a modifier of azo organic pigment water-based ink, aiming at the problems in the prior art. The preparation method of the modifying agent provided by the invention aims at the azo organic pigment water-based base ink, can effectively reduce the viscosity of the water-based base ink and improve the viscosity stability of the water-based base ink, is beneficial to the use, storage and transportation of the water-based base ink, further promotes the further popularization and application of the water-based base ink, and has a wide market application prospect.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
the modifying agent for azo organic pigment water-based ink comprises organic triamine, inorganic acid, organic dimer acid and solvent.
The preparation method of the modifier comprises the following steps:
(1) reacting organic triamine with inorganic acid to obtain an intermediate 1; wherein the organic triamine is selected from one or more of linear chain structures and branched chain structures of diethylene triamine, dipropylene triamine, dibutylene triamine, dipentylene triamine, dihexylene triamine and diheptylene triamine, and preferably is diethylene triamine; the inorganic acid is selected from one or more of dilute sulfuric acid, hydrochloric acid, dilute nitric acid and hydrobromic acid, and preferably dilute sulfuric acid and hydrochloric acid; wherein the mass concentration of the inorganic acid is 10-35%. The general formula of the chemical reaction is as follows:
wherein n is 2 to 7.
(2) Carrying out single-end condensation reaction on the intermediate 1 obtained in the step (1) and organic dimer acid to obtain a macromolecular hydrophilic compound; wherein the structural formula of the organic dimer acid is HOOC-CxHy-COOH, wherein x is 32-34 and y is 62-66, preferably dimer fatty acid, wherein said dimer fatty acid is obtained by polymerizing one or two of oleic acid and linoleic acid, and the effective content is 95% or more. The general formula of the chemical reaction is as follows:
wherein n is 2-7, x is 32-34, and y is 62-66.
(3) Heating the macromolecular hydrophilic compound obtained in the step (2) in a solvent, and dispersing at a high speed to obtain a modifier with a required concentration; wherein the weight ratio of the macromolecular hydrophilic compound to the solvent is 1: 10-100; the temperature is raised to 50-80 ℃, and the high-speed dispersion time is 1.5-5 h; wherein the solvent is selected from one or more of methanol, ethanol, propanol, acetic acid and water.
Further, the step (1) is specifically as follows: heating organic triamine to 25-80 ℃, adding inorganic acid, and reacting for 0.5-5h to obtain an intermediate 1; wherein the molar ratio of the organic triamine to the inorganic acid is 1: 1-1.2.
Further, the condensation reaction in the step (2) is specifically as follows: adding organic dimer acid into the intermediate 1 obtained in the step (1), stirring, heating to 95-100 ℃, preserving heat for 1-5h, and continuously heating to 120-220 ℃, preserving heat for 1-5h to obtain a macromolecular hydrophilic compound; wherein the molar ratio of the intermediate 1 to the organic dimer acid is 1: 0.45-0.50.
The modifier is applied to improving the viscosity and viscosity stability of the azo organic pigment water-based ink; the specific using method of the modifier is as follows: adding the modifier after the pigmentation stage of azo pigment synthesis, fully stirring, filtering, rinsing, drying and crushing to obtain the modified azo organic pigment; the pigmenting step of the azo pigment synthesis is a surface coating and particle modification treatment step of the pigment.
The modifier is added in the synthesis process of the organic pigment, wherein the red series of the organic pigment comprises: c.i. pigment red 2, c.i. pigment red 4, c.i. pigment red 8, c.i. pigment red 21, c.i. pigment red 22, c.i. pigment red 48: 1. c.i. pigment red 48: 2. c.i. pigment red 48: 3. c.i. pigment red 48: 4. c.i. pigment red 48: 5. c.i. pigment red 49: 1. c.i. pigment red 49: 2. c.i. pigment red 49: 3. c.i. pigment red 52: 1. c.i. pigment red 52: 2. c.i. pigment red 53: 1. c.i. pigment red 57: 1. c.i. pigment red 58: 1. c.i. pigment red 58: 2. c.i. pigment red 58: 3. c.i. pigment red 58: 4. c.i. pigment red 60: 1. c.i. pigment red 61, c.i. pigment red 62, c.i. pigment red 63: 1. c.i. pigment red 63: 2. c.i. pigment red 112, c.i. pigment red 146, c.i. pigment red 170, c.i. pigment red 185, c.i. pigment red 187, c.i. pigment red 188, c.i. pigment red 266, and the like.
The modifier can also be applied to other color pigments, and the other color pigments comprise: c.i. pigment brown 1, c.i. pigment brown 3, c.i. pigment brown 5, c.i. pigment brown 23, c.i. pigment brown 25, c.i. pigment yellow 1, c.i. pigment yellow 2, c.i. pigment yellow 3, c.i. pigment yellow 4, c.i. pigment yellow 5, c.i. pigment yellow 12, c.i. pigment yellow 13, c.i. pigment yellow 14, c.i. pigment yellow 17, c.i. pigment yellow 63, c.i. pigment yellow 74, c.i. pigment yellow 81, c.i. pigment yellow 83, c.i. pigment yellow 150, c.i. pigment yellow 151, c.i. pigment yellow 154, c.i. pigment yellow 174, c.i. pigment orange 1, c.i. pigment orange 5, c.i. pigment yellow 13, c.i. pigment orange 16, c.i. pigment orange 34, c.i. pigment orange 36, and the like.
Compared with the prior art, the invention has the following beneficial effects:
improving the viscosity and viscosity stability of the aqueous base ink. The azo-based organic pigment is selectively added into the azo-based organic pigment, so that the viscosity of the azo-based organic pigment aqueous base ink can be reduced, and the storage stability can be improved.
Detailed Description
The embodiments of the present invention are described below with reference to specific embodiments, and other advantages and effects of the present invention will be easily understood by those skilled in the art from the disclosure of the present specification. The invention is capable of other and different embodiments and of being practiced or of being carried out in various ways, and its several details are capable of modification in various respects, all without departing from the spirit and scope of the present invention.
Before the present embodiments are further described, it is to be understood that the scope of the invention is not limited to the particular embodiments described below; it is also to be understood that the terminology used in the examples is for the purpose of describing particular embodiments only, and is not intended to limit the scope of the present invention.
When numerical ranges are given in the examples, it is understood that both endpoints of each of the numerical ranges and any value therebetween can be selected unless the invention otherwise indicated. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.
The sources of the raw materials used in the present invention are not limited, and the raw materials used in the present invention are all those commonly available in the art unless otherwise specified.
In the following examples, "parts" means "parts by mole" and "%" means "% by weight".
Example 1
(1) Heating 103g (1mol) of diethylenetriamine to 40 ℃, adding 122g of 30% (1mol) hydrochloric acid, and reacting for 3 hours to obtain an intermediate triamine hydrochloride solution;
(2) 282g (0.5mol) of HOOC-C were added to the triamine hydrochloride solution obtained in the above step (1)34H62Heating to 100 ℃ under strong stirring, and keeping the temperature for 3 hours; continuously heating to 220 ℃, and preserving heat for 1h to obtain a viscous macromolecular condensation compound;
(3) and (3) taking 10g of the viscous macromolecular condensation compound obtained in the step (2), adding 500g of water and 500g of ethanol, heating to 40 ℃, and dispersing at a high speed for 2 hours to obtain 1010g of modifier emulsion.
Example 2
(1) Heating 131g (1mol) of dipropylenetriamine to 80 ℃, adding 196g of 25% (1mol) of dilute sulfuric acid, and reacting for 0.5 hour to obtain an intermediate 1;
(2) 283g (0.5mol part) of HOOC-C was added to the intermediate 1 obtained in the above step (1)34H64Heating to 95 ℃ under strong stirring, and keeping the temperature for 5 hours; continuously heating to 120 ℃, and preserving heat for 5 hours to obtain a viscous macromolecular condensation compound;
(3) and (3) taking 10g of the viscous macromolecular condensation compound obtained in the step (2), adding 500g of water and 500g of ethanol, heating to 40 ℃, and dispersing at a high speed for 2 hours to obtain 1010g of modifier emulsion.
Example 3
(1) Heating 131g (1mol) of dipropylenetriamine to 80 ℃, adding 252g (30% (1mol) of dilute nitric acid, and reacting for 0.5h to obtain an intermediate 1;
(2) 282g (1mol) of HOOC-C was added to the intermediate 1 obtained in the above step (1)34H62Heating the acid-COOH to 100 ℃ under strong stirring, and keeping the temperature for 1 h; continuously heating to 220 ℃, and preserving heat for 1h to obtain a viscous macromolecular condensation compound;
(3) and (3) taking 10g of the viscous macromolecular condensation compound obtained in the step (2), adding 1000g of water, heating to 40 ℃, and dispersing at a high speed for 2h to obtain 1010g of modifier.
Comparative example 1
The difference from example 1 is that hydrochloric acid was not added, and the rest was the same.
Comparative example 2
The difference from example 1 was that 30% hydrochloric acid was replaced with the same amount of acetic acid, and the rest was the same.
Examples of the experiments
Detection method
1. Preparation of azo pigment sample
18.7g (0.1mol) of 4-aminotoluene-3-sulfonic acid were added to 200g of water, 14g of 30% (0.105mol) sodium hydroxide solution was added, and the mixture was heated to 30 ℃ to dissolve completely. Adding ice blocks into the dissolved solution, adjusting the temperature to 0-5 ℃, adding 30g of 30% (0.25mol) hydrochloric acid, stirring for 5min, adding 23g of 30% (0.1mol) sodium nitrite solution, performing diazotization reaction, detecting by using starch-KI test paper to keep slight blue-slight blue, continuously stirring for 30min, and keeping the temperature at 0-5 ℃ to obtain a diazo component for later use.
19g (0.101mol) of 2-hydroxy-3-naphthoic acid was added to 150g of water, 14g of 30% (0.105mol) sodium hydroxide solution was added thereto, and the mixture was heated to 30 ℃ to completely dissolve the compound. Adding ice, cooling to 10-12 deg.C, adjusting volume to 300ml, and making into coupling component.
Adding diazo component into coupling component, standing for 10-20min, adjusting pH to 10-11 after coupling, and keeping stirring at 10-15 deg.C for 60 min. 12g of water-based modified rosin is added for hydrophilic coating, 48g of 30 percent (0.13mol) calcium chloride solution is added for precipitation reaction, and the stirring is continued for 30 min. Heating to 80 ℃, adding 30g of 30% (0.67mol) aluminum chloride solution, keeping the temperature for 20min, adjusting the pH value to 6-7 by using sodium hydroxide, adding 10g of the modifier emulsion prepared in the example 1-3 and the comparative example 1-2 respectively/without adding any modifier emulsion, continuously stirring for 10min, filtering, rinsing, drying, crushing, collecting samples to obtain C.I. pigment red 57:1 sample 45g, and detecting.
2. Preparation of aqueous base inks
Mixing the above components with 75g of zirconium beads with diameter of 0.4-0.6mm, placing in 250ml PVC bottle, dispersing on a shaking instrument for 60min, and filtering with a filter screen to remove zirconium beads to obtain the final product base ink.
3. Viscosity detection of aqueous based inks
The finished base ink prepared above was placed in a glass container, and the initial viscosity of the aqueous base ink immediately after formation was measured at 25 ℃ with a BM type viscometer. (Unit: cps)
4. Aqueous based ink viscosity stability detection
The base ink, which was tested for initial viscosity, was contained in a sealed glass container, and then subjected to an acceleration test: and (3) placing the ink in a constant temperature box at 60 ℃, preserving heat for 72h, taking out, cooling to 25 ℃, and measuring the viscosity of the water-based ink again by using a BM type viscometer. (Unit: cps)
Whether the pigment-based ink is excellent or not in fluidity is evaluated by testing the initial viscosity and the viscosity value after the accelerated test of each pigment-based ink, and the results are shown in table 1.
TABLE 1
The present invention has been further described with reference to specific embodiments, which are only exemplary and do not limit the scope of the present invention. It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention, and that such changes and modifications may be made without departing from the spirit and scope of the invention.
Claims (7)
1. The preparation method of the modifier is characterized by comprising the following steps of:
(1) reacting organic triamine with inorganic acid to obtain an intermediate 1;
(2) carrying out single-end condensation reaction on the intermediate 1 obtained in the step (1) and organic dimer acid to obtain a macromolecular hydrophilic compound;
(3) dispersing the macromolecular hydrophilic compound obtained in the step (2) in a solvent to obtain a modifier;
the organic triamine in the step (1) is selected from one or more of straight chain structures and branched chain structures of diethylene triamine, dipropylene triamine, dibutyl triamine, dipentylene triamine, dihexyl triamine and diheptylene triamine;
the inorganic acid in the step (1) is selected from one or more of dilute sulfuric acid, hydrochloric acid, dilute nitric acid and hydrobromic acid; wherein the mass concentration of the inorganic acid is 10-35%;
the structural formula of the organic dimer acid in the step (2) is HOOC-CxHy-COOH, wherein x =32-34, y = 62-66;
the molar ratio of the organic triamine to the inorganic acid is 1: 1-1.2; the molar ratio of the intermediate 1 to the organic dimer acid is 1: 0.45-0.50.
2. The method of claim 1, wherein: and (3) the solvent is selected from one or more of methanol, ethanol, propanol, acetic acid and water.
3. The method of claim 1, wherein: the step (1) is specifically as follows: heating organic triamine to 25-80 ℃, adding inorganic acid, and reacting for 0.5-5h to obtain an intermediate 1.
4. The method of claim 1, wherein: the condensation reaction in the step (2) is specifically as follows: adding organic dimer acid into the intermediate 1 obtained in the step (1), stirring, heating to 80-100 ℃, preserving heat for 1-5h, and continuously heating to 120-220 ℃, preserving heat for 1-5h to obtain the macromolecular hydrophilic compound.
5. The method of claim 1, wherein: in the step (3), the weight part ratio of the macromolecular hydrophilic compound to the solvent in the modifier is 1: 10-100.
6. The modifier produced by the production method according to any one of claims 1 to 5, wherein the raw materials comprise an organic triamine, an inorganic acid, an organic dimer acid and a solvent.
7. Use of the modifier according to claim 6 for improving the viscosity and viscosity stability of aqueous azo-based organic pigment-based inks.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101380555A (en) * | 2008-10-09 | 2009-03-11 | 东华大学 | Dispersant for salicylic acid derivatives pigments and preparation method and use thereof |
| CN103275518A (en) * | 2013-05-30 | 2013-09-04 | 鞍山七彩化学股份有限公司 | Method for preparing high-transparency high-strength pigment yellow 155 for water-based ink and water-based paint |
| CN106833005A (en) * | 2017-01-23 | 2017-06-13 | 浙江浩川科技有限公司 | A kind of method for preparing permeability azo organic pigment high |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO1999007758A1 (en) * | 1997-08-04 | 1999-02-18 | Nippon Bee Chemical Co., Ltd. | Emulsion and process for preparing the same |
| DE10318233A1 (en) * | 2003-04-22 | 2004-11-11 | Clariant Gmbh | Water-based colorant preparations for ink jet printing |
| KR102012613B1 (en) * | 2012-05-09 | 2019-08-20 | 선 케미칼 코포레이션 | Surface modified pigment particles, method of preparation and application thereof |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101380555A (en) * | 2008-10-09 | 2009-03-11 | 东华大学 | Dispersant for salicylic acid derivatives pigments and preparation method and use thereof |
| CN103275518A (en) * | 2013-05-30 | 2013-09-04 | 鞍山七彩化学股份有限公司 | Method for preparing high-transparency high-strength pigment yellow 155 for water-based ink and water-based paint |
| CN106833005A (en) * | 2017-01-23 | 2017-06-13 | 浙江浩川科技有限公司 | A kind of method for preparing permeability azo organic pigment high |
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