CN109111787A - A kind of organic amine improving organic pigment dispersion performance - Google Patents
A kind of organic amine improving organic pigment dispersion performance Download PDFInfo
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- CN109111787A CN109111787A CN201810548274.2A CN201810548274A CN109111787A CN 109111787 A CN109111787 A CN 109111787A CN 201810548274 A CN201810548274 A CN 201810548274A CN 109111787 A CN109111787 A CN 109111787A
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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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C291/00—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00
- C07C291/02—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds
- C07C291/04—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds containing amino-oxide bonds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
Abstract
The present invention relates to organic chemicals technical fields, more particularly to a kind of organic amine for improving organic pigment dispersion performance, it is polymeric ether amine salt, after adding the sulfonated products of organic pigment dispersion or the pigment base in organic pigment addition dicyandiamide solution ink after the polymeric ether amine salt is mixed with the pigment base in dicyandiamide solution ink, then it is directly added into the polymeric ether amine salt and is dispersed；For improving dispersion performance of the organic pigment in dicyandiamide solution ink, the dispersion product of the high yield synthesized in the aqueous state, while improving the mobile performance and environmental-protecting performance of dispersion product.
Description
Technical field
The present invention relates to organic chemicals technical fields, improve the organic of organic pigment dispersion performance more particularly to a kind of
Amine and the preparation method and application thereof.
Background technique
The solvent dispersion of organic pigment needs low viscosity, high transparency and high gloss, is especially packed for solvent inkjet ink.This
Solvent in a little ink, more typically oxygen-containing type, alcohols, esters, ethers and its mixture, such as: ethyl alcohol, propyl alcohol, acetic acid
Ethyl ester, isopropyl acetate, monomethyl ether of propyleneglycoles etc..Typical resins of the dissolution in these solvents as packaging ink have
Nitrocellulose, polyamide, polyurethane or CPP resin.
United States Patent (USP) U.S.Pat.Nos.4,057,436 and 4,518,435 propose, with amine or the acid of quaternary ammonium salt and pigment
Reaction, obtains certain salt, the method can substantially reduce viscosity, improve the mobility of pigment dispersion.But these salts
It is that alcoxyl base class rather than is based on based on the salt for using tertiary amine or quaternary ammonium, therefore, to the subsequent water-soluble and feature of environmental protection
It hinders.United States Patent (USP) U.S.Pat.Nos.6,926,768 propositions improve the mobility of pigment dispersion with alkoxide compound, no
Crossing the substance not is water solubility, in pigment process, needs pH value by inorganic acid, such as hydrochloric acid to be adjusted to reactant
To 1-2, temperature is increased to 80-95 DEG C to guarantee that reaction carries out, reacts handling poor, reaction yield is lower.
Summary of the invention
The present invention is in order to improve water solubility, the feature of environmental protection that organic pigment is dispersed in solvent inkjet ink and finally improve final receipts
Low temperature in rate and production process is handling, provides a kind of new structural organic amine, organic under the action of the organic amine
Pigment is dispersed in the various performances in solvent inkjet ink and shows well.
The technical solution for solving above-mentioned technical problem is as follows:
It is a kind of improve organic pigment dispersion performance organic amine, be polymeric ether amine salt, by the polymeric ether amine salt with it is molten
Organic pigment dispersion is added after pigment base mixing in agent system ink or organic pigment is added in dicyandiamide solution ink
After the sulfonated products of pigment base, then it is directly added into the polymeric ether amine salt and is dispersed；
The polymeric ether amine salt, has a structure that
Wherein, R is the alkyl group or aryl group of 1~21 carbon；
The integer that n is 1~50.
Pigment base in the dicyandiamide solution ink be phthalocyanine, copper phthalocyanine, it is any one in quinacridone, carbazole violet
Kind is a variety of；The organic pigment be phthalocyanine, copper phthalocyanine, any one or more in quinacridone, carbazole violet.
Improve the preparation method of the organic amine of organic pigment dispersion performance, comprising the following steps:
(1) ether amines are put intoInto reaction kettle, nitrogen protection after the completion of investment；
(2) rabbling mechanism for opening reaction kettle, is adjusted to 80~85 DEG C for temperature of reaction kettle, to material in reactor temperature
When reaching 75~78 DEG C, methyl chloride CH is added into reaction kettle by the way of dropwise addition3Cl dripped methyl chloride in 1~3 hour
It adds complete；
(3) after methyl chloride all adds, control reaction mass temperature is 85~100 DEG C, is reacted 2-4 hours；Until anti-
Answering material in kettle is in yellowish transparency liquid, sampling analysis.
The feed ratio of the ether amines and methyl chloride is 7-10:1 according to mass ratio.
The application of the organic amine is the dispersion performance for improving organic pigment in dicyandiamide solution ink, obtains water-soluble
The dispersion product of property, while improving the mobile performance and environmental-protecting performance of dispersion product.
Organic pigment be phthalocyanine, copper phthalocyanine, any one or more in quinacridone, carbazole violet, the solvent body
Be pigment base in ink be phthalocyanine, copper phthalocyanine, any one or more in quinacridone, carbazole violet.
Beneficial effects of the present invention:
The present invention provides a kind of organic amine for improving organic pigment dispersion performance, organic pigment is dispersed in solvent inkjet ink,
Add the organic amine so that the solvent type dispersion product synthesizes in the aqueous state, meet dispersion steps need low viscosity,
The requirement of high transparency and high gloss, organic amine use alkyl group or aryl group, can play a role in low-temperature condition,
The yield of dispersion product 20-30% can be improved.And due to avoiding dispersing in oleaginous system, substantially reduces pollution and reach environmental protection
Purpose.
Detailed description of the invention
The present invention will be further described in detail below with reference to the accompanying drawings and specific embodiments.
Fig. 1 is that (R is the alkyl group of 7 carbon to polymeric ether amine salt of the present invention；N is carbon spectrum spectrogram 18), can from figure
Contain Cl-, CH to analyze sintetics2,CH3It is strong；
Fig. 2 is that (R is the alkyl group of 7 carbon to polymeric ether amine salt of the present invention；N is hydrogen spectrum spectrogram 18)；It can from figure
Cl- base is shown to analyze the section 6.5-7.5, and the section 3-4 is shown containing 1-2 O-CH2Strong, 2-3 contains 1 NH and is good for, and 0-1 contains
There is the CH of sealing end3Base；
Fig. 3 is that (R is the alkyl group of 7 carbon to polymeric ether amine salt of the present invention；N is infrared spectrogram 18)；From figure
It can analyze out sintetics and contain Cl-, CH2,CH3It is strong；
Specific embodiment
Following example 1 and 2 is to use to be added without " polymeric ether amine salt " of the present invention and addition 8 under equal conditions
Example made by " the polymeric ether amine salt " of mass parts, comparative example 3 and 4 are using United States Patent (USP) US6, and 926,768 methods are made
Dispersion product comparison case.
Embodiment 1:
86 parts of copper phthalocyanines and 4 parts of copper phthalocyanine sulfonic acid filter cake CuPc (SO3) .n=1.5, it is suspended in 1500 parts of water,
Stirring at normal temperature 1 hour, filtering, filter cake was through 50~60 DEG C of hot water wash, and when PH=7-8,70 DEG C are dried, yield 65%.
Embodiment 2:
86 parts of copper phthalocyanines and 4 parts of copper phthalocyanine sulfonic acid filter cake CuPc (SO3) .n=1.5, it is suspended in 1500 parts of water, beats
Polymeric ether amine salt prepared by the present invention is added in slurry, and (R is the aryl group of 6 carbon；N is 6) 8 parts of quantity, small in stirring at normal temperature 1
When, filtering, filter cake is through 50~60 DEG C of hot water wash, and when PH=7-8,70 DEG C are dried, yield 85%.
The pigment of 20 parts of processing, are added in 80 parts of nitrocellulose base-materials, add 100 parts of diameter 2mm beades, in earthquake machine
Dispersion 60 minutes, then diluted with nitrocellulose base-material and solvent (ethyl alcohol: ethyl acetate=2:1-3:1).
Comparative example 3:
86 parts of copper phthalocyanines and 4 parts of copper phthalocyanine sulfonic acid filter cake CuPc (SO3) .n=1.5, it is suspended in 1200 parts of water, beats
Slurry is added sodium hydroxide and adjusts pH=9.5~10.0, stirs 1 hour at 85~90 DEG C, 2.5 parts of polyethylene-polypropylene lists are added
Methyl ether (2- propyl) amine (Jeffamine M2070) and 2.5 parts of polyethylene-polypropylene glycol monoethyl ether (2- propyl) amine
(Jeffamine M2005) is stirred 30 minutes.Then 2 part of two cocoyl alkyl dimethyl ammonium chloride (Arquad 2TH-75) is added,
It is stirred 1 hour at 80~90 DEG C.Filtering, 50~60 DEG C of hot water wash of filter cake, when pH=7-8,70 DEG C are dried.
Comparative example 4:
86 parts of copper phthalocyanines and 4 parts of copper phthalocyanine sulfonic acid filter cake CuPc (SO3) .n=1.5, mashing 6.5 parts of poly- second of addition
Alkene-glycol polypropylene monomethyl ether (2- propyl) amine Jeffamine M2005,80~90 DEG C are stirred 1 hour, and filtration washing is dry
It is dry.
It is shown in Table 1 in the testing result of nitrocellulose base-material solvent system, testing conditions are the same as example 2.
Table 1
| Example | Tinting strength, tinting power % | 60 degree of angle % of gloss | Viscosity (cps) | The transparency |
| 1 (untreated) | 100% | 20.1 | > 500 | - |
| 2 | 120.5 | 108 | 150 | 6 grades or more thoroughly |
| 3 | 110 | 58.5 | 200 | 4 grades thoroughly |
| 4 | 108 | 65.5 | 450 | 3-4 grades thoroughly |
Evaluation method is as follows:
Mobility: the pigment dispersion of production measures viscosity in 6 and 60rpm with BF viscosimeter.
Tone and gloss: intaglio inks scrape sample on a tectorial paper with a bar applicator.Tone is estimated, glossiness is used
Meter is in 60 degree of angular measurement gloss.
Tinting strength, tinting power: intaglio inks are mixed with chalk, on tectorial paper, visual valuation.
Table 1 is the evaluation result of intaglio inks, it can be seen that for the present invention compared with comparative example, performance is more outstanding.
In order to further expand operability of the invention, embodiment 5-8 further changes organic pigment and dicyandiamide solution
Pigment base in ink makees further derivative explanation to the present invention.
Embodiment 5:
(1) 100 parts of ether amines are put into(R CH3) into reaction kettle, investment is completed
Nitrogen protection afterwards；
(2) rabbling mechanism for opening reaction kettle, is adjusted to 80 DEG C for temperature of reaction kettle, reaches to material in reactor temperature
At 75 DEG C, 10 parts of methyl chloride CH are added into reaction kettle by the way of dropwise addition3Methyl chloride is added dropwise in 1 hour by Cl；
(3) after methyl chloride all adds, control reaction mass temperature is 85 DEG C, is reacted 2 hours；Until object in reaction kettle
Material is in yellowish transparency liquid, and sampling analysis obtains(R CH3；1) n is.
Added after the polymeric ether amine salt is mixed with the pigment base in dicyandiamide solution ink organic pigment dispersion or
After the sulfonated products of the pigment base in dicyandiamide solution ink are added in organic pigment, then it is directly added into the polymeric ether amine salt and is divided
It dissipates；Pigment base in dicyandiamide solution ink is phthalocyanine；Organic pigment is.According to embodiment 2 method handle pigment with it is right
Ratio 3 and 4 compares, gloss, transparent higher, tinting strength, tinting power 117%.
Embodiment 6:
(1) 70 parts of ether amines are put into(alkyl group that R is 21 carbon) arrives reaction kettle
In, nitrogen protection after the completion of investment；
(2) rabbling mechanism for opening reaction kettle, is adjusted to 85 DEG C for temperature of reaction kettle, reaches to material in reactor temperature
At 78 DEG C, 10 parts of methyl chloride CH are added into reaction kettle by the way of dropwise addition3Methyl chloride is added dropwise in 3 hours by Cl；
(3) after methyl chloride all adds, control reaction mass temperature is 100 DEG C, is reacted 4 hours；Until in reaction kettle
Material is in yellowish transparency liquid, and sampling analysis obtainsWherein, R is 21
The alkyl group of carbon；N is 50.
Added after the polymeric ether amine salt is mixed with the pigment base in dicyandiamide solution ink organic pigment dispersion or
After the sulfonated products of the pigment base in dicyandiamide solution ink are added in organic pigment, then it is directly added into the polymeric ether amine salt and is divided
It dissipates；Pigment base in dicyandiamide solution ink is, the mixture of quinacridone, carbazole violet；Organic pigment is phthalocyanine, quinacridine
The mixture of ketone, carbazole violet.The pigment handled according to the method for embodiment 2 is gloss, transparent higher compared with comparative example 3 and 4,
Tinting strength, tinting power is 115.7%.
Embodiment 7:
(1) 80 parts of ether amines are put into(aryl group that R is 12 carbon) arrives reaction kettle
In, nitrogen protection after the completion of investment；
(2) rabbling mechanism for opening reaction kettle, is adjusted to 82 DEG C for temperature of reaction kettle, reaches to material in reactor temperature
At 77 DEG C, 10 parts of methyl chloride CH are added into reaction kettle by the way of dropwise addition3Methyl chloride is added dropwise in 2 hours by Cl；
(3) after methyl chloride all adds, control reaction mass temperature is 90 DEG C, is reacted 3 hours；Until object in reaction kettle
Material is in yellowish transparency liquid, and sampling analysis obtainsWherein, R is 12 carbon
Aryl group；N is 25.
Added after the polymeric ether amine salt is mixed with the pigment base in dicyandiamide solution ink organic pigment dispersion or
After the sulfonated products of the pigment base in dicyandiamide solution ink are added in organic pigment, then it is directly added into the polymeric ether amine salt and is divided
It dissipates；Pigment base in dicyandiamide solution ink be phthalocyanine, copper phthalocyanine, the mixture of quinacridone；Organic pigment is phthalocyanine, copper
Phthalocyanine, the mixture of quinacridone.The pigment handled according to the method for embodiment 2 is gloss, saturating with comparative example 3 and 4 compared with
Ming Genggao, tinting strength, tinting power 119%.
Embodiment 8:
(1) 90 parts of ether amines are put into(alkyl group that R is 18 carbon) arrives reaction kettle
In, nitrogen protection after the completion of investment；
(2) rabbling mechanism for opening reaction kettle, is adjusted to 84 DEG C for temperature of reaction kettle, reaches to material in reactor temperature
At 76 DEG C, 10 parts of methyl chloride CH are added into reaction kettle by the way of dropwise addition3Cl dripped methyl chloride in 1.5 hours
Finish；
(3) after methyl chloride all adds, control reaction mass temperature is 95 DEG C, is reacted 3 hours；Until object in reaction kettle
Material is in yellowish transparency liquid, and sampling analysis obtainsWherein, R is 18 carbon
Alkyl group；N is 40.
Added after the polymeric ether amine salt is mixed with the pigment base in dicyandiamide solution ink organic pigment dispersion or
After the sulfonated products of the pigment base in dicyandiamide solution ink are added in organic pigment, then it is directly added into the polymeric ether amine salt and is divided
It dissipates；Pigment base in dicyandiamide solution ink is any one or more in carbazole violet；Organic pigment is carbazole violet.According to embodiment
The pigment of 2 method processing is compared with comparative example 3 and 4, gloss, transparent higher, tinting strength, tinting power 123%.
The above is only presently preferred embodiments of the present invention, not does limitation in any form to the present invention, it is all according to
According to any simple modification to the above embodiments in technical spirit of the invention, equivalent variations, guarantor of the invention is each fallen within
Within the scope of shield.
Claims (6)
1. a kind of organic amine for improving organic pigment dispersion performance, which is characterized in that be polymeric ether amine salt, by the polymeric ether
Amine salt adds organic pigment dispersion after mixing with the pigment base in dicyandiamide solution ink or dicyandiamide solution is added in organic pigment
After the sulfonated products of pigment base in ink, then it is directly added into the polymeric ether amine salt and is dispersed；
The polymeric ether amine salt, has a structure that
Wherein, R is the alkyl group or aryl group of 1~21 carbon；
The integer that n is 1~50.
2. the organic amine according to claim 1 for improving organic pigment dispersion performance, which is characterized in that the solvent body
Be pigment base in ink be phthalocyanine, copper phthalocyanine, any one or more in quinacridone, carbazole violet；Organic face
Material be phthalocyanine, copper phthalocyanine, any one or more in quinacridone, carbazole violet.
3. a kind of preparation method of the described in any item organic amines for improving organic pigment dispersion performances of such as claims 1 or 2,
It is characterized in that, comprising the following steps:
(1) ether amines are put intoInto reaction kettle, nitrogen protection after the completion of investment；
(2) rabbling mechanism for opening reaction kettle, is adjusted to 80~85 DEG C for temperature of reaction kettle, reaches to material in reactor temperature
At 75~78 DEG C, methyl chloride CH is added into reaction kettle by the way of dropwise addition3Cl dripped methyl chloride in 1~3 hour
Finish；
(3) after methyl chloride all adds, control reaction mass temperature is 85~100 DEG C, is reacted 2-4 hours；Until reaction kettle
Interior material is in yellowish transparency liquid, sampling analysis.
4. the preparation method of the organic amine according to claim 3 for improving organic pigment dispersion performance, which is characterized in that ether
The feed ratio of amine and methyl chloride is 7-10:1 according to mass ratio.
5. a kind of application of organic amine as described in claim 1, which is characterized in that for improving organic pigment in dicyandiamide solution
Dispersion performance in ink obtains water-soluble dispersion product, while improving the mobile performance and environmental-protecting performance of dispersion product.
6. the application of organic amine according to claim 5, which is characterized in that the organic pigment be phthalocyanine, copper phthalocyanine,
, quinacridone, any one or more in carbazole violet, the pigment base in the dicyandiamide solution ink be phthalocyanine, copper phthalocyanine,
, quinacridone, any one or more in carbazole violet.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6471764B1 (en) * | 2000-11-16 | 2002-10-29 | Sun Chemical Corporation | Treatment of high performance pigments with etheramine dispersing salts |
| CN101516992A (en) * | 2006-08-09 | 2009-08-26 | 胡茨曼石油化学公司 | Comb-like polyether alkanolamine in ink and paint |
| CN104508059A (en) * | 2012-07-16 | 2015-04-08 | 巴斯夫欧洲公司 | Pigment dispersions, their preparation, and dispersants |
| CN106232743A (en) * | 2014-04-18 | 2016-12-14 | 蓝宝迪有限公司 | Additive for jetted ink |
| CN107033341A (en) * | 2017-04-06 | 2017-08-11 | 浙江浩川科技有限公司 | A kind of organic pigment hyper-dispersant, Its Preparation Method And Use |
| CN107635917A (en) * | 2015-02-11 | 2018-01-26 | 塞特工业公司 | The amine of the modification useful as the scale inhibitor in Wet-process Phosphoric Acid Production |
-
2018
- 2018-05-31 CN CN201810548274.2A patent/CN109111787A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6471764B1 (en) * | 2000-11-16 | 2002-10-29 | Sun Chemical Corporation | Treatment of high performance pigments with etheramine dispersing salts |
| CN101516992A (en) * | 2006-08-09 | 2009-08-26 | 胡茨曼石油化学公司 | Comb-like polyether alkanolamine in ink and paint |
| CN104508059A (en) * | 2012-07-16 | 2015-04-08 | 巴斯夫欧洲公司 | Pigment dispersions, their preparation, and dispersants |
| CN106232743A (en) * | 2014-04-18 | 2016-12-14 | 蓝宝迪有限公司 | Additive for jetted ink |
| CN107635917A (en) * | 2015-02-11 | 2018-01-26 | 塞特工业公司 | The amine of the modification useful as the scale inhibitor in Wet-process Phosphoric Acid Production |
| CN107033341A (en) * | 2017-04-06 | 2017-08-11 | 浙江浩川科技有限公司 | A kind of organic pigment hyper-dispersant, Its Preparation Method And Use |
Non-Patent Citations (1)
| Title |
|---|
| XUESONG JIANG等: "《Amphiphilic Zwitterionic Poly(dimethylsiloxane) (PDMS)-Contained Poly(Ether amine) (Z-SIPEA) as the Responsive Polymeric Dispersant》", 《ACS APPLIED MATERIALS & INTERFACES》 * |
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