CN1687157A - Method for preparing macromolecule modifier for organic pigment - Google Patents
Method for preparing macromolecule modifier for organic pigment Download PDFInfo
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- CN1687157A CN1687157A CN 200510040111 CN200510040111A CN1687157A CN 1687157 A CN1687157 A CN 1687157A CN 200510040111 CN200510040111 CN 200510040111 CN 200510040111 A CN200510040111 A CN 200510040111A CN 1687157 A CN1687157 A CN 1687157A
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Abstract
The present invention disclose sa method for preparing high-molecular modifying agent for organic pigment. The adoption of said modifying agent can obtain nano-grade organic pigment with bright colour, good flowability and high stability.
Description
Technical field
The invention discloses a kind of preparation method of macromolecule modifier for organic pigment, this properties-correcting agent can be used for preparing water-thinned nanometer paint and printing paste, belongs to field of fine chemical.
Background technology
Pigment is widely used in fields such as weaving, papermaking, furniture, rubber, plastics, metal spraying and building as a kind of tinting material.Yet,, cause the vividness and the luminance range of color, thereby limited the widespread use of pigment because the particle of common pigments is thick and maldistribution.In addition, pigment has only to be dispersed in uniformly and stably in the medium as a kind of tinting material, could bring into play its pigmentation preferably.Therefore, pigment refinement and dispersion processing are its prerequisites of being used widely.
The pigment dyestuff surface polarity is lower, is difficult to wetting in water and dispersion.Therefore, pigment dyestuff is that dispersion medium uses with the organic solvent under many circumstances.The use of organic solvent is contaminate environment not only, and influences the healthy of operating worker.Make colo(u)rant dispersion in aqueous medium, the use that reduces organic solvent is the emphasis research topic in current pigment field.To with colo(u)rant dispersion in aqueous medium, need carry out modification to surface of pigments.The method that the pigment dyestuff modification is generally adopted is with nonionic, negatively charged ion, cation dispersing agent surface of pigments to be handled, and perhaps adopts polymkeric substance that pigment is carried out micro encapsulation processing.The former is by deposition on surface of pigments or coat unit molecule or polymolecular dispersion agent, reaches to change surface of pigments polar purpose.The latter is to be the capsule heart with the pigment dyestuff, and natural, semi-synthetic or synthetic polymkeric substance is the wall material, adopts suitable physico-chemical process that it is deposited on the granules of pigments surface, forms the pigment microcapsule.
In recent years, hyper-dispersant (Hyper-dispersants) is because its special structure and performance become the research focus that colo(u)rant dispersion is processed, and relevant patent and bibliographical information are more.People such as C Ao Shila, E Eckstein disclose a kind of block copolymer-modified dose preparation method; MA SHEAU-HWA discloses a kind of preparation method of graft copolymer.In addition, United States Patent (USP) and European patent have also carried out numerous descriptions and report to the preparation method of macromolecule modifier.Although still there is certain problem in these macromolecule modifiers from having improved the stable and mobile of colo(u)rant dispersion in varying degrees on dispersion efficiency, how the pigment dyestuff dispersion processing is become nano particle is the focus that the scientific worker studies always.
Summary of the invention
The invention discloses a kind of macromolecule modifier that can be used for the pigment modification, this properties-correcting agent is the multipolymer of hydrophobic monomer and hydrophilic monomer.Adopt this properties-correcting agent that pigment is carried out modification, can prepare bright in colour bright, good fluidity, water nano organic pigment dispersions system that stability is high.
Technical scheme of the present invention is as follows:
The synthetic method of macromolecule modifier can adopt mass polymerization, solution polymerization process.Mass polymerization exists speed of response fast, and auto-acceleration effect is obvious, shortcomings such as the difficult control of reaction.The present invention adopts solution polymerization process, placement part solvent in reactor, after stirring is warmed up to certain temperature, reaction monomers, initiator and remaining solvent are added drop-wise in the reactor with certain speed, the insulation certain hour, after reaction is finished, add precipitation agent and make polymer precipitation, after the filtration product repetitive scrubbing is removed monomer and the impurity of not participating in reaction.After drying at a certain temperature, product obtains pulverous macromolecule modifier.Also properties-correcting agent can be dissolved in the water, adjusting the pH value with alkali is 6-10, makes certain density modification liquid.In addition, this properties-correcting agent can with the composite use of other low dispersal agent molecule, improve modified effect.
Macromolecule modifier of the present invention is two yuan or a terpolymer of hydrophobic monomer and hydrophilic monomer.Hydrophobic monomer is one or both mix monomers in divinyl, vinylchlorid, vinylidene chloride, vinyl fluoride, tetrafluoroethylene, iso-butylene, isoprene, dicyclopentadiene, vinylbenzene, butyl acrylate, ethyl propenoate, methyl acrylate, methyl methacrylate, Jia Jibingxisuanyizhi, butyl methacrylate, vinyl acetate, the methylvinylether.Hydrophilic monomer is one or both mix monomers in vinylformic acid, methacrylic acid, acrylamide, maleic toxilic acid, maleic anhydride, vinylformic acid methyl methylene-succinic acid, the third rare nitrile.
Solvent of the present invention has one or more mixed solvents in pimelinketone, vinyl acetic monomer, N-BUTYL ACETATE, tetrahydrofuran (THF), TriMethylolPropane(TMP), methylene dichloride, dimethyl formamide, acetone, butanone, pyrrolidone, methyl butyl ketone, dimethyl sulfoxide (DMSO), tetramethylene sulfone, chloroform, tetracol phenixin, the 2-methyl-2-pyrrolidone.
The initiator that polymerization is adopted has azo-initiator such as Diisopropyl azodicarboxylate, 2,2'-Azobis(2,4-dimethylvaleronitrile); Organic peroxy class initiator such as isopropyl benzene hydroperoxide, t-butyl hydrogen peroxide, dicumyl peroxide, di-tert-butyl peroxide, dibenzoyl peroxide, dilauroyl peroxide, di-cyclohexylperoxy dicarbonate, di-isopropyl peroxydicarbonate; A kind of in the radical initiators such as inorganic peroxy class initiator such as hydrogen peroxide, Ammonium Persulfate 98.5, peroxidation sulfuric acid potassium.
The precipitation agent that is adopted is one or more mixtures in the sherwood oil, benzene, toluene, ethylbenzene, dimethylbenzene, chlorobenzene of methyl alcohol, ethanol, propyl alcohol, Virahol, propyl carbinol, isopropylcarbinol, water, ether, dipropyl ether, methyl-phenoxide, hexanaphthene, methylcyclohexane, various boiling ranges.
The method of the invention be will monomer and initiator dissolving back be added drop-wise in the reactor with certain speed, the heat that polymerization produces can spread out rapidly, is unlikely to occur gel effect and auto-acceleration effect, thereby has guaranteed that successful reaction carries out.
The prepared properties-correcting agent of the present invention can be used for the surface modification of multiple pigment dyestuff, as azo class pigment, phthalocyanine pigment, quinoline azete ketone pigment, dioxazines pigment, 1,4-diketopyrrolo-pyrrole class pigment, condensed ring ketone pigment, nitro and nitroso pigments, nitrogen methyne class pigment, pyrazolo quinolinones pigment, quinophthalone class pigment, chloro isoindolinone and isoindoline class pigment.
The low dispersal agent molecule that adopts when composite is anionic dispersing agent such as potassium oleate, sodium abietate, sodium lauryl sulphate, Sodium dodecylbenzene sulfonate, sodium alkyl naphthalene sulfonate; A kind of among non-ionic dispersing agent such as Tween60, Tween61, Tween65, Tween80, Tween81, Tween85, OP-5, OP-10, OP-1 5, Span 20, Span40, Span 60, Span 65, Span 80, Span 83, Span 85, Tx-10, Tx-10s, peregal A-20, paregal O-25, peregal os-15, SG-10, LAE-9, OE-15, the SE-10.
The basic technology parameter of preparation properties-correcting agent is: hydrophobic monomer and hydrophilic monomer mol ratio are 3: 1-1: 3, and the consumption of initiator is the 1%-5% of monomer total mass, the solvent total amount is 1-5 a times of monomer total mass.When synthetic, the solvent with 1/2-2/3 joins in the reactor earlier, and temperature of reaction is controlled at 50 ℃-100 ℃, and the reaction times is 2-10 hour, and the consumption of precipitation agent is 1-3 a times of solvent total mass.When composite, the mass ratio of low dispersal agent molecule and macromolecule modifier is 5: 1-1: 5.
Beneficial effect of the present invention: adopt the macromolecule modifier range of molecular weight distributions of this method preparation narrow, constant product quality is used for the surface of pigments modification, can prepare bright-colored bright, good fluidity, nano level organic pigment dispersions system that stability is high.Preparation method's technical process of the present invention is brief, facility investment is little, reaction can be carried out under lower temperature, gelatin phenomenon and automatic hastening phenomenon can not occur.
Embodiment
Embodiment 1
Reaction monomers methyl methacrylate 10.1 grams (0.1mol), methacrylic acid 8.6 grams (0.1mol) and butyl acrylate 12.9 grams (0.1mol) are dissolved in the 31.6 gram pimelinketone, add dibenzoyl peroxide 0.57 gram, make monomer in solvent, fully dissolve, mix with initiator.Get the reactor that 63.2 gram pimelinketone place band stirring and condenser, stir, be warming up to 75 ℃, mix monomer is added drop-wise in the reactor, reacted 8 hours.Cooling adds 100-300 gram sherwood oil in reaction mixture, make polymer precipitation, filters and obtains synthetic product.With product filter cake repetitive scrubbing, dry under 40～60 ℃, obtain macromolecule modifier.
Accurately weighing 1 gram macromolecule modifier adds 24 gram deionized waters, and the pH value that the aqueous sodium hydroxide solution of employing 1mol/l is adjusted system is 8-9, prepares the certain density macromolecule modifier aqueous solution.
In modifier aqueous solution, add 1.0 gram Tween80, obtain the combination solution of properties-correcting agent and low dispersal agent molecule.
Embodiment 2
Reaction monomers methyl methacrylate 10.1 grams (0.1mol), methacrylic acid 8.6 grams (0.1mol) are dissolved in the 18.7 gram dimethyl formamides, add Diisopropyl azodicarboxylate 0.56 gram, monomer and initiator fully are dissolved in the solvent.Get the reactor that 37.4 gram dimethyl formamides place band stirring and condenser, stir, be warming up to 60 ℃, mix monomer is added drop-wise in the reactor, reacted 10 hours.Cooling adds 50-150 gram hexanaphthene in reaction mixture, make polymer precipitation, filter crude product.With the crude product repetitive scrubbing, dry under 40～60 ℃, obtain macromolecule modifier.
Accurately weighing 4 gram macromolecule modifiers add 76 gram deionized waters, and the pH value that the aqueous sodium hydroxide solution of employing 1mol/l is adjusted system is 8-9, prepares the certain density macromolecule modifier aqueous solution.
In modifier aqueous solution, add 1.0 gram Sodium dodecylbenzene sulfonatees, obtain the combination solution of properties-correcting agent and low dispersal agent molecule.
Embodiment 3
Reaction monomers maleic anhydride 9.8 grams (0.1mol), methylvinylether 11.6 grams (0.2mol) are dissolved in the 21.2 gram tetrahydrofuran (THF)s, add di-cyclohexylperoxy dicarbonate 0.51 gram, monomer and initiator fully are dissolved in the solvent.Get the reactor that 42.4 gram tetrahydrofuran (THF)s place band stirring and condenser, stir, be warming up to 70 ℃, mix monomer is added drop-wise in the reactor, reacted 6 hours.Cooling adds 50-150 gram toluene in reaction mixture, make polymer precipitation, filter crude product, with the crude product repetitive scrubbing, 40～60 ℃ dry down, obtain macromolecule modifier.
Accurately weighing 1 gram macromolecule modifier adds 24 gram deionized waters, and the pH value that the aqueous sodium hydroxide solution of employing 1mol/l is adjusted system is 8-9, prepares the certain density macromolecule modifier aqueous solution.
In modifier aqueous solution, add 4.0 gram OP-15, obtain the combination solution of properties-correcting agent and low dispersal agent molecule.
Embodiment 4
Reaction monomers vinylbenzene 10.4 grams (0.1mol), butyl acrylate 6.3 grams (0.05mol) and vinylformic acid 7.2 grams (0.1mol) are dissolved in the 23.9 gram dimethyl sulfoxide (DMSO), add Diisopropyl azodicarboxylate 0.48 gram, monomer and initiator fully are dissolved in the solvent.Get the reactor that 47.8 gram dimethyl sulfoxide (DMSO) place band stirring and condenser, stir, be warming up to 85 ℃, mix monomer is added drop-wise in the reactor, reacted 8 hours.Cooling adds 70-200 gram ethanol in reaction mixture, make polymer precipitation, filter crude product, with the crude product repetitive scrubbing, 40～60 ℃ dry down, obtain macromolecule modifier.
Accurately weighing 1 gram macromolecule modifier adds 24 gram deionized waters, and the pH value that the aqueous sodium hydroxide solution of employing 1mol/l is adjusted system is 8-9, prepares the certain density macromolecule modifier aqueous solution.
In modifier aqueous solution, add 1.0 gram OE-15, obtain the combination solution of properties-correcting agent and low dispersal agent molecule.
Claims (9)
1. the preparation method of a macromolecule modifier for organic pigment, it is characterized in that properties-correcting agent is two yuan or terpolymer of hydrophobic monomer and hydrophilic monomer, the mol ratio of hydrophobic monomer and hydrophilic monomer is 3: 1-1: 3, in reactor, place 1/3～2/3 solvent, under agitation be warming up to 50 ℃-100 ℃, the consumption of initiator is the 1%-5% of monomer total mass, with reaction monomers, initiator and remaining solvent are added drop-wise in the reactor with certain speed, the total consumption of solvent is 1-5 a times of monomer total mass, after insulation reaction 2-10 hour, add precipitation agent and make polymer precipitation, product repetitive scrubbing after the filtration is removed monomer and the impurity of not participating in reaction, it is dried at a certain temperature, obtain pulverous macromolecule modifier; Maybe the macromolecule modifier with preparation is dissolved in the water, and adjusting the pH value with alkali is 6-10, makes certain density modifier solution, this properties-correcting agent and the composite use of other low dispersal agent molecule, and effect is better.
2. preparation method according to claim 1 is characterized in that used hydrophobic monomer is one or both mix monomers in divinyl, vinylchlorid, vinylidene chloride, vinyl fluoride, tetrafluoroethylene, iso-butylene, isoprene, dicyclopentadiene, vinylbenzene, butyl acrylate, ethyl propenoate, methyl acrylate, methyl methacrylate, Jia Jibingxisuanyizhi, butyl methacrylate, vinyl acetate or the methylvinylether.
3. preparation method according to claim 1 is characterized in that used hydrophilic monomer is one or both mix monomers in vinylformic acid, methacrylic acid, acrylamide, maleic toxilic acid, maleic anhydride, vinylformic acid methyl methylene-succinic acid, the third rare nitrile.
4. preparation method according to claim 1 is characterized in that solvent for use is one or more mixed solvents in pimelinketone, vinyl acetic monomer, N-BUTYL ACETATE, tetrahydrofuran (THF), TriMethylolPropane(TMP), methylene dichloride, dimethyl formamide, acetone, butanone, pyrrolidone, methyl butyl ketone, dimethyl sulfoxide (DMSO), tetramethylene sulfone, chloroform, tetracol phenixin, the 2-methyl-2-pyrrolidone.
5. preparation method according to claim 1 is characterized in that used initiator is that azo-initiator is Diisopropyl azodicarboxylate, 2,2'-Azobis(2,4-dimethylvaleronitrile); Organic peroxy class initiator is isopropyl benzene hydroperoxide, t-butyl hydrogen peroxide, dicumyl peroxide, di-tert-butyl peroxide, dibenzoyl peroxide, dilauroyl peroxide, di-cyclohexylperoxy dicarbonate, di-isopropyl peroxydicarbonate; Inorganic peroxy class initiator is hydrogen peroxide, Ammonium Persulfate 98.5, peroxidation sulfuric acid potassium, a kind of in the above-mentioned initiator.
6. preparation method according to claim 1 is characterized in that used precipitation agent is one or more mixtures in the sherwood oil, benzene, toluene, ethylbenzene, dimethylbenzene, chlorobenzene of methyl alcohol, ethanol, propyl alcohol, Virahol, propyl carbinol, isopropylcarbinol, water, ether, dipropyl ether, methyl-phenoxide, hexanaphthene, methylcyclohexane, various boiling ranges.
7. preparation method according to claim 1 is characterized in that it is a kind of in aqueous sodium hydroxide solution, ammoniacal liquor, the trolamine aqueous solution, the aqueous sodium carbonate that used pH value is adjusted agent.
8. preparation method according to claim 1, it is characterized in that composite used low dispersal agent molecule is anionic dispersing agent such as potassium oleate, sodium abietate, sodium lauryl sulphate, Sodium dodecylbenzene sulfonate, sodium alkyl naphthalene sulfonate, or non-ionic dispersing agent such as Tween60, Tween61, Tween65, Tween80, Tween81, Tween85, OP-5, OP-10, OP-15, Span 20, Span 40, Span 60, Span 65, Span 80, Span 83, Span 85, Tx-10, Tx-10s, peregal A-20, paregal O-25, peregal os-15, SG-10, LAE-9, OE-15, a kind of among the SE-10.
9. preparation method according to claim 1, it is characterized in that elder generation joins the solvent of 1/2-2/3 in the reactor, remaining solvent is used for dissolved monomer and initiator, and adopt the mode that drips that monomer and initiator are joined in the reactor, constantly stir, the consumption of precipitation agent is 1-3 a times of the total consumption of solvent, and when composite, the mass ratio of low dispersal agent molecule and macromolecule modifier is 5: 1-1: 5.
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| Application Number | Priority Date | Filing Date | Title |
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| CNB2005100401116A CN1308362C (en) | 2005-05-18 | 2005-05-18 | Method for preparing macromolecule modifier for organic pigment |
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| CNB2005100401116A CN1308362C (en) | 2005-05-18 | 2005-05-18 | Method for preparing macromolecule modifier for organic pigment |
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| CN1308362C CN1308362C (en) | 2007-04-04 |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102517106A (en) * | 2011-12-13 | 2012-06-27 | 南京大学 | Slurry stabilizing agent and applications thereof |
| CN102532939A (en) * | 2011-12-16 | 2012-07-04 | 江南大学 | Preparation method of water-based self-dispersion nano organic pigment powder |
| CN106009772A (en) * | 2016-05-27 | 2016-10-12 | 无锡润新染料有限公司 | Azo compound dye and preparation method thereof |
| CN108360288A (en) * | 2018-02-12 | 2018-08-03 | 广东轻工职业技术学院 | A kind of mill base dispersant and its preparation method and application of addition rosin |
| CN108666138A (en) * | 2017-03-29 | 2018-10-16 | 东莞东阳光科研发有限公司 | A kind of 650-700V electrolyte for aluminum electrolytic capacitor |
| CN108727869A (en) * | 2018-07-04 | 2018-11-02 | 南京林业大学 | Aqueous easy dispersion monoazo nanometer organic pigment of one kind and preparation method thereof |
| CN108878151A (en) * | 2017-05-09 | 2018-11-23 | 东莞市东阳光电容器有限公司 | A kind of 700-750V electrolyte for aluminum electrolytic capacitor |
| CN115197589A (en) * | 2021-04-08 | 2022-10-18 | 长沙族兴新材料股份有限公司 | Polymer-coated aluminum pigment with high metal effect and preparation method thereof |
-
2005
- 2005-05-18 CN CNB2005100401116A patent/CN1308362C/en not_active Expired - Fee Related
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102517106A (en) * | 2011-12-13 | 2012-06-27 | 南京大学 | Slurry stabilizing agent and applications thereof |
| CN102532939A (en) * | 2011-12-16 | 2012-07-04 | 江南大学 | Preparation method of water-based self-dispersion nano organic pigment powder |
| CN102532939B (en) * | 2011-12-16 | 2014-11-12 | 江南大学 | Preparation method of water-based self-dispersion nano organic pigment powder |
| CN106009772A (en) * | 2016-05-27 | 2016-10-12 | 无锡润新染料有限公司 | Azo compound dye and preparation method thereof |
| CN108666138A (en) * | 2017-03-29 | 2018-10-16 | 东莞东阳光科研发有限公司 | A kind of 650-700V electrolyte for aluminum electrolytic capacitor |
| CN108666138B (en) * | 2017-03-29 | 2020-12-29 | 东莞东阳光科研发有限公司 | Electrolyte for 650-plus 700V aluminum electrolytic capacitor |
| CN108878151A (en) * | 2017-05-09 | 2018-11-23 | 东莞市东阳光电容器有限公司 | A kind of 700-750V electrolyte for aluminum electrolytic capacitor |
| CN108878151B (en) * | 2017-05-09 | 2021-03-26 | 东莞市东阳光电容器有限公司 | 700-750V aluminum electrolytic capacitor electrolyte |
| CN108360288A (en) * | 2018-02-12 | 2018-08-03 | 广东轻工职业技术学院 | A kind of mill base dispersant and its preparation method and application of addition rosin |
| CN108727869A (en) * | 2018-07-04 | 2018-11-02 | 南京林业大学 | Aqueous easy dispersion monoazo nanometer organic pigment of one kind and preparation method thereof |
| CN115197589A (en) * | 2021-04-08 | 2022-10-18 | 长沙族兴新材料股份有限公司 | Polymer-coated aluminum pigment with high metal effect and preparation method thereof |
| CN115197589B (en) * | 2021-04-08 | 2023-09-22 | 长沙族兴新材料股份有限公司 | Polymer coated aluminum pigment with high metal effect and preparation method thereof |
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Assignee: Kunshan Sunmun Technology Development Co., Ltd. Assignor: Jiangnan University Contract fulfillment period: 2007.5.10 to 2017.5.10 contract change Contract record no.: 2008320000454 Denomination of invention: Method for preparing macromolecule modifier for organic pigment Granted publication date: 20070404 License type: Exclusive license Record date: 2008.9.27 |
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Free format text: EXCLUSIVE LICENCE; TIME LIMIT OF IMPLEMENTING CONTACT: 2007.5.10 TO 2017.5.10 Name of requester: KUNSHAN SHIMING SCIENCE & TECHNOLOGY DEVELOPMENT Effective date: 20080927 |
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