CN101418137A - Method for preparing ultrafine organic pigment/polymer compound powder by using in-situ polymerization - Google Patents
Method for preparing ultrafine organic pigment/polymer compound powder by using in-situ polymerization Download PDFInfo
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Abstract
The invention relates to a method for preparing superfine organic pigment/polymer composite powder by adopting in-situ polymerization, which belongs to the technical field of the fine chemistry industry. The method is as follows: organic pigment is dispersed in a solvent for a period of time by means of supersonic waves or grinding, and is subjected to temperature rise to a certain temperature; a corresponding amount of mixed monomers and an initiator are dissolved in the same solvent and uniformly mixed; and a solution containing the monomers and the initiator is dripped into a dispersing solution of the organic pigment under the condition of continuous dispersion, and the superfine organic pigment/polymer composite powder material is prepared and applied to prepare a pigment dispersant for dyeing textile fabrics. The method has simple and convenient technology, is easy to operate, and effectively controls the surface property of the composite powder material by adjustment of the structure of synthon; and the composite powder material prepared has good compatibility with a dispersing medium, and can effectively reduce aggregation of particles and improve the properties such as the wettability, the decentrality, the specific surface area, the tinctorial yield and the transparency.
Description
Technical field
The invention belongs to field of fine chemical, be specifically related to a kind of method of using situ aggregation method to coat one deck or multiple layer polymer on the ultrafine organic paint surface.
Background technology
Commercial pigment dyestuff mainly is to exist with forms such as aggregate, aggregates, and surface polarity is low, is difficult to wetted and dispersion at aqueous phase.So processability is stable, the good textile coating of color characteristics need carry out modification to pigment dyestuff.
Surface coating modification is main means of improving pigment dyestuff surface property and processing characteristics, this method is core with the pigment dyestuff, by proper method at its surperficial coated polymer, inorganic materials or other material, thereby change the surface polarity of pigment dyestuff, make itself and working medium have better consistency.The surface coated method of common pigment dyestuff has solvent evaporated method, spray-drying process, situ aggregation method and phase separation method etc.People such as Feng Wei adopt situ aggregation method to coat urea-formaldehyde resin on the Phthalocyanine Green G surface, have obtained the uniform mobile ball-type solid microcapsule of size distribution; People such as Zhang Tianyong adopt phase separation method to coat polystyrene on the CuPc surface, have greatly improved the stability of pigment in organic solvent and mobile; And CN01811377.X discloses the method for a kind of spray-drying process in the agent of surface of pigments coating and bonding; Among the CN95103810.9 organic modifiers is coated to the conductive pigment surface, has prepared the conductive pigment of surface modification.
Add dispersion agent, it also is the important method of pigment dyestuff surface modification that powder is ground.A kind of method that adopts the physical grinding method to coat one deck nano silicone base oxide and nano-titanium oxide, zinc oxide mixture on the pigment dyestuff surface is disclosed among the CN00125874.5.In addition, introducing active group on the pigment dyestuff surface, also is the surface coated common methods of pigment dyestuff by polyreaction then.People such as Paul Palumbo utilize the azo group of pigment dyestuff self, introduced active function groups by diazotization reaction on the pigment dyestuff surface, then by copolyreaction, realized the dispersion of pigment dyestuff and stable thereby introduce long solvent chain on the pigment dyestuff surface.
The present invention adopts situ aggregation method, has coated polymer materials on the pigment dyestuff surface, has prepared ultrafine organic paint/polymer particle composite granule.
Summary of the invention
The objective of the invention is the method that open employing in-situ polymerization prepares ultrafine organic paint/polymer composite particle, composite granule and working medium through this method preparation have better consistency, thereby minimizing particle accumulation, improve the dispersed and stable of pigment dyestuff, and, the function of polymkeric substance can be incorporated into pigment dyestuff/polymer particle composite granule by changing the polymer wall equipment structure.
Technical scheme of the present invention: a kind of method that adopts in-situ polymerization to prepare ultrafine organic paint/polymer compound powder body material, pigment dyestuff is distributed in the solvent, adopt ultrasonic wave or grinding means that it is disperseed for some time, take out dispersion liquid and place reactor, be warming up to certain temperature; Mix monomer and the initiator of getting respective amount are dissolved in in a kind of solvent, mix; The drips of solution that will contain monomer and initiator under stirring condition is added in the dispersion liquid of pigment dyestuff, the isothermal reaction certain hour, and suction filtration, and with washing composition repetitive scrubbing suction filtration thing, vacuum-drying makes ultrafine organic paint/polymer compound powder body material;
The basic technology parameter is: pigment dyestuff and monomer weight ratio 1: 1-1: 2.5 (mol ratio is 2: 1-20: 1), solvent load is 2-12 a times of monomer total mass, initiator amount is the 0.1%-5% of monomer total mass, and temperature of reaction is controlled at 50 ℃-80 ℃, and the time is 3h-8h.
Pigment dyestuff is selected for use: azo class pigment, triarylmethane compound pigment, phthalocyanine pigment, dioxazines pigment, quinophthalone class pigment, nitrogen methyne class pigment, nitro and nitrous base class pigment, condensed ring ketone pigment, pyrazolo quinolinones pigment, pyroles pigment or indoline-like pigment.
The monomer that uses is selected for use: one or more in vinylbenzene, tetrafluoroethylene, iso-butylene, isoprene, methyl acrylate, ethyl propenoate, butyl acrylate, methyl methacrylate, Jia Jibingxisuanyizhi, butyl methacrylate, methylvinylether, vinylformic acid, acrylamide, maleic anhydride, the vinyl cyanide.
The solvent that uses is selected for use: toluene, tetrahydrofuran (THF), TriMethylolPropane(TMP), dimethyl formamide, pyrrolidone, methyl butyl ketone, tetramethylene sulfone or tetracol phenixin.
The initiator that uses is selected for use: Diisopropyl azodicarboxylate, 2,2'-Azobis(2,4-dimethylvaleronitrile), dicumyl peroxide, di-tert-butyl peroxide, dibenzoyl peroxide, dilauroyl peroxide, di-cyclohexylperoxy dicarbonate or di-isopropyl peroxydicarbonate.
The washing composition that uses is selected for use: methyl alcohol, ethanol, Virahol, water or sherwood oil.
The application of the ultrafine organic paint/polymer compound powder body material of preparation, be used for the pigment preparation dispersion liquid, fabric is dyeed, the preparation of dispersible pigment dispersion: ultrafine organic paint/polymer compound powder body material 10-20g, dispersion agent 2-3.5g evenly spreads in the 100g water;
The dispersion agent that uses is selected for use: anionic: sodium lauryl sulphate, Sodium dodecylbenzene sulfonate, potassium oleate, sodium alkyl naphthalene sulfonate, sodium abietate; In non-ionic type: OP series emulsifying agent, Tween series emulsifying agent, Span series emulsifying agent, Tx series emulsifying agent, the peregal series emulsifying agent one or more.
Beneficial effect of the present invention: the preparation method of a kind of easy, easy to operate ultrafine organic paint/polymer compound powder body is provided, and this method can be effectively controlled the surface properties of composite particles by adjusting the structure of synthon.And the composite particles of present method preparation has good consistency with dispersion medium, can effectively reduce aggregation of particles, improves wettability and dispersiveness.
Embodiment
Below by examples of implementation, further set forth outstanding advantage of the present invention and distinguishing feature, but the present invention is in no way limited to examples of implementation.
Embodiment 1: take by weighing 10g C.I. pigment Yellow 12, be distributed in the 40g toluene, disperse 30min under the ultrasonic wave effect, place four-hole boiling flask, be warming up to 65 ℃, and constantly stir.Monomer maleic anhydride 6.5g, n-butyl acrylate 8g and 0.14g Diisopropyl azodicarboxylate are dissolved in the other 50g toluene, monomer solution is added drop-wise in the Pigment Yellow 73 dispersion liquid, insulation reaction 3h, finish the back and take out sample, suction filtration makes the composite particles powder of C.I. pigment Yellow 12/polymkeric substance more also with a large amount of methyl alcohol repetitive scrubbings through 60 ℃ of vacuum-drying 12h.Take by weighing above-mentioned powder 9.3g, Sodium dodecylbenzene sulfonate 0.9g, OP-100.1g place in the 200ml beaker, add deionized water 50g, dispersed with stirring 30min, and obtaining median size is the composite granule dispersion liquid of 152.4nm.
Embodiment 2:
Accurately take by weighing 8g C.I. Pigment red 53, be distributed in the 50g tetrahydrofuran (THF), place sand mill grinding at room temperature 3h.Other gets and is dissolved in the 60g tetrahydrofuran (THF) after vinylbenzene 6.2g, acrylamide 4.6g mix, 0.12g the initiator dibenzoyl peroxide is dissolved in the 10g tetrahydrofuran (THF), then C.I. Pigment red 53 dispersion liquids are added in the four-hole boiling flask, again vinylbenzene, acrylamide monomer mixed solution 23.6g and initiator solution 3g are added in the four-hole boiling flask, stirring is warming up to 50 ℃, constant temperature 20min.Remaining 47.2g monomer solution and 7.1g initiator solution are joined the constant voltage separating funnel, 15min dropwises, and 70 ℃ of insulation reaction 6h finish the back and take out sample then, also with a large amount of ethanol repetitive scrubbings, 50 ℃ of vacuum-drying 8h make C.I. Pigment red 53/ polymer particle powder to suction filtration.Get above-mentioned powder 8.6g, sodium alkyl naphthalene sulfonate 0.5g, this class 800.5g places in the 200ml beaker, adds deionized water 50g, and dispersed with stirring 15min obtains the dispersible pigment dispersion that median size is 164.3nm.
Embodiment 3: accurately take by weighing 6.3g C.I. pigment violet 19, be distributed in the 30g TriMethylolPropane(TMP), use ultrasonic dispersing 20min.Methylvinylether 4.7g, vinyl cyanide 9.5g are dissolved in the 70g TriMethylolPropane(TMP) after mixing, 0.16g the initiator Diisopropyl azodicarboxylate is dissolved in the other 20g TriMethylolPropane(TMP), then C.I. pigment violet 19 dispersion liquids are added in the four-hole boiling flask, again methylvinylether, acrylonitrile monemer mixed solution 24.2g and initiator solution 6.3g are added in the four-hole boiling flask, stirring is warming up to 55 ℃, constant temperature 10min.Remaining 60g monomer solution and 13.84g initiator solution are joined the constant voltage separating funnel, 20min dropwises, and 70 ℃ of insulation reaction 4h finish the back and take out sample then, also with a large amount of ethanol repetitive scrubbings, 50 ℃ of vacuum-drying 12h make C.I. pigment violet 1 9/ polymer particle powder to suction filtration.Take by weighing above-mentioned modified powder 6.5g, sodium lauryl sulphate 0.73g, paregal O 0.47g places in the 200ml beaker, adds deionized water 35g, and dispersed with stirring 20min obtains the dispersible pigment dispersion that median size is 128.5nm.
Embodiment 4: accurately take by weighing 3.6g C.I. pigment orange 40, be distributed in the 36g methyl butyl ketone, place sand mill grinding at room temperature 4h.Monomer vinylformic acid 7.2g is dissolved in the 72g methyl butyl ketone.0.08g the initiator dilauroyl peroxide is dissolved in the other 12g methyl butyl ketone.C.I. pigment orange 40 dispersion liquids are added in the four-hole boiling flask, again Acrylic Acid Monomer solution 36g and initiator solution 6.08g are added in the four-hole boiling flask, stir and be warming up to 60 ℃, constant temperature 20min.Remaining 43.2g monomer solution and 6g initiator solution are joined the constant voltage separating funnel, 15min dropwises, and 80 ℃ of insulation reaction 3h finish the back and take out sample then, also with a large amount of methyl alcohol repetitive scrubbings, 60 ℃ of vacuum-drying 24h make C.I. pigment orange 40/ polymer particle powder to suction filtration.Take by weighing above-mentioned powder 5g, OP emulsifying agent 1g places in the 200ml beaker, adds deionized water 35g, and dispersed with stirring 30min obtains the dispersible pigment dispersion that median size is 137.2nm.
Claims (7)
1, a kind of method that adopts in-situ polymerization to prepare ultrafine organic paint/polymer compound powder body material is characterized in that pigment dyestuff is distributed in the solvent, and employing ultrasonic wave or grinding means are warming up to certain temperature after it is disperseed for some time; Mix monomer and the initiator of getting respective amount are dissolved in in a kind of solvent, mix; The drips of solution that will contain monomer and initiator under continuing the dispersive condition is added in the dispersion soln of pigment dyestuff, the isothermal reaction certain hour, suction filtration, and with washing composition repetitive scrubbing suction filtration thing, vacuum-drying makes ultrafine organic paint/polymer compound powder body material;
The basic technology parameter is: pigment dyestuff and monomer weight ratio 1: 1-1: 2.5, and solvent load is 2-12 a times of monomer total mass, and initiator amount is the 1%-5% of monomer total mass, and temperature of reaction is controlled at 50 ℃-80 ℃, and the time is 3h-8h.
2, method according to claim 1 is characterized in that pigment dyestuff selects for use: azo class pigment, triarylmethane compound pigment, phthalocyanine pigment, dioxazines pigment, quinophthalone class pigment, nitrogen methyne class pigment, nitro and nitrous base class pigment, condensed ring ketone pigment, pyrazolo quinolinones pigment, pyroles pigment or indoline-like pigment.
3, method according to claim 1 is characterized in that the monomer that uses selects for use: one or more in vinylbenzene, tetrafluoroethylene, iso-butylene, isoprene, methyl acrylate, ethyl propenoate, butyl acrylate, methyl methacrylate, Jia Jibingxisuanyizhi, butyl methacrylate, methylvinylether, vinylformic acid, acrylamide, maleic anhydride, the vinyl cyanide.
4, method according to claim 1 is characterized in that the solvent that uses selects for use: toluene, tetrahydrofuran (THF), TriMethylolPropane(TMP), dimethyl formamide, pyrrolidone, methyl butyl ketone, tetramethylene sulfone or tetracol phenixin.
5, method according to claim 1 is characterized in that the initiator that uses selects for use: Diisopropyl azodicarboxylate, 2,2'-Azobis(2,4-dimethylvaleronitrile), dicumyl peroxide, di-tert-butyl peroxide, dibenzoyl peroxide, dilauroyl peroxide, di-cyclohexylperoxy dicarbonate or di-isopropyl peroxydicarbonate.
6, method according to claim 1 is characterized in that the washing composition that uses selects for use: methyl alcohol, ethanol, Virahol, water or sherwood oil.
7, the application of the ultrafine organic paint/polymer compound powder body material of claim 1 method preparation, it is characterized in that the pigment preparation dispersion liquid, be used for fabric is dyeed, the preparation of dispersible pigment dispersion: ultrafine organic paint/polymer compound powder body material 10-20g, dispersion agent 2-3.5g evenly is dissolved in the 100g water;
The dispersion agent that uses is selected for use: anionic: sodium lauryl sulphate, Sodium dodecylbenzene sulfonate, potassium oleate, sodium alkyl naphthalene sulfonate, sodium abietate; In non-ionic type: OP series emulsifying agent, Tween series emulsifying agent, Span series emulsifying agent, Tx series emulsifying agent, the peregal series emulsifying agent one or more.
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| 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 |
| CN106752254A (en) * | 2016-12-06 | 2017-05-31 | 浙江力禾集团有限公司 | A kind of production method of the special C.I. pigment Yellow 14s of water paint |
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| CN102926224A (en) * | 2012-11-27 | 2013-02-13 | 江南大学 | Preparation method of pigment ink for inkjet printing of non-adhesive textile |
| 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 |
| CN106752254A (en) * | 2016-12-06 | 2017-05-31 | 浙江力禾集团有限公司 | A kind of production method of the special C.I. pigment Yellow 14s of water paint |
| CN107168012A (en) * | 2017-07-11 | 2017-09-15 | 深圳市华星光电技术有限公司 | A kind of colored photoresist and preparation method thereof |
| CN107793786A (en) * | 2017-11-10 | 2018-03-13 | 南通恒盛精细化工有限公司 | The method for preparing the azo compound of narrow particle diameter distribution |
| CN111269518A (en) * | 2020-03-20 | 2020-06-12 | 杨海青 | Antioxidant pigment composition and preparation method thereof |
| CN113668094A (en) * | 2021-07-20 | 2021-11-19 | 浙江理工大学 | Preparation method of polyphenyl acrylic/pigment composite colored filament |
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