CN105838103A - Method for direct synthesis of nano phthalocyanine copper pigment - Google Patents
Method for direct synthesis of nano phthalocyanine copper pigment Download PDFInfo
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- CN105838103A CN105838103A CN201610187828.1A CN201610187828A CN105838103A CN 105838103 A CN105838103 A CN 105838103A CN 201610187828 A CN201610187828 A CN 201610187828A CN 105838103 A CN105838103 A CN 105838103A
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- pigment
- copper phthalocyanine
- microwave
- organic solvent
- filter cake
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y40/00—Manufacture or treatment of nanostructures
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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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
- C09B47/067—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile
Abstract
The invention belongs to the field of preparation of organic pigments, and in particular to a method for direct synthesis of a nano phthalocyanine copper pigment. The method comprises the following steps: weighing materials; evenly stirring by ultrasonic mixing; heating by microwave to the end of reaction to obtain preliminary reaction products; stirring washing the preliminary products, standing for layering, and taking a lower layer material; subjecting the lower material to azeotropic distillation to obtain a filter cake; washing and drying the filter cake with methanol to obtain the nano copper phthalocyanine. The method employ a chemical method for direct synthesis of nano grade copper phthalocyanine pigment, which can satisfy the requirement of dyeing ability, dispersion and stability of the pigment in the medium, and the full color and luster.
Description
Technical field
The invention belongs to the preparation field of organic pigment, a kind of nanoscale copper phthalocyanine pigments that is directly synthesized
Method.
Technical background
The miniaturization always pigment manufacturer of pigment (organic pigment and inorganic pigment) granule needs to solve for a long time
Key problem in technology and a difficult problem.So that pigment has a wide range of applications characteristic, pigment production producer needs preparation
Going out tinting strength, tinting power high, good dispersion, good stability in using medium, and full pigment bright in colour, this is just
Require pigment granule is tiny and narrow particle size distribution.But owing to granules of pigments is the most tiny, its surface can be the biggest, more
Easily again can be condensed into hard bulky grain, make application performances such as tinting strength, tinting power, dispersibility, particle diameter distribution etc. big
Big decline, this problem always perplexing pigment manufacturer.
At present, manufacturing field at pigment, the method tackling this problem mainly has following several:
(1) polytype surface conditioning agent is added to stop or to subtract less granular gathering;
(2) mix certain specific isomeric compound to reach to stop or reduce to coagulate with the crystal growth affecting pigment
Poly-generation;
(3) raw by crystal formation being modified or controlled by post processing means such as solvent method, acid pasting, ball-milling methods
Long, reach suppression flocculation and occur;
(4) take the grinding and processing technology of machinery and physics, manufacture attritive powder, increase pressure as used
Contracting power and frictional force carry out the high pressure homogenizer pulverized or use grinding of media material.
Owing to introducing surface conditioning agent and other isomeric compound in said method (1) and (2), to some to product
The special occasions that product purity has higher requirements is the most inapplicable, and divides with the pigment particle size of both of these approaches manufacture
Cloth wider (i.e. size is uneven) is also significant deficiency.
Said method (3) is to introduce again substantial amounts of organic solvent or concentrated sulphuric acid or grinding aid after pigment synthesizes specially
Agent carries out pigmentation process to pigment, makes crystalline pigment and granular size meet application requirement, this method shortcoming
The step pigmentation treatment process that has been many, and produce a large amount of waste liquid simultaneously, process in this way and be also difficult to make
Go out nano level pigment.
Said method (4) is after drying by physical method at pigment, uses substantial amounts of mechanical energy to reach super
Finely divided purpose.This method easily causes microstrain, defect, causes the poly-of high surface energy at fresh surface
Collection, its particle size distribution is to be evenly distributed, less application in pigment manufactures.
And can be used for manufacturing ultra-fine and that dispersive property is good organic pigment currently without effective technological means.
Summary of the invention
In order to realize above-mentioned technical purpose, the present invention provides a kind of side being directly synthesized nanoscale copper phthalocyanine pigments
Method, it can meet producer and to pigmenting power, dispersibility in media as well and stablize and full color
Requirement.
For achieving the above object, the concrete technical scheme that the present invention takes is: one is directly synthesized nanoscale phthalein
The method of cyanines copper pigment, comprises the technical steps that: first operation, weighs following material by weight: pole
Property organic solvent 270-280 part, phthalic nitrile 40-60 part, carbamide 8-15 part, ammonium molybdate 0.3-1 part, chlorine
Change cuprous;Wherein, the weight portion of Cu-lyt. is the 1/8-1/5 of phthalic nitrile;
Second operation work, is uniformly mixed the material weighed on supersonic generator;The most ultrasonic
Condition is: frequency 80-95HZ, and the time is 30min-1h;
Three process, is placed in microwave reactor microwave heating to 180-190 DEG C by the material of mix homogeneously,
Material reacts, and constant temperature keeps 20min, and reaction terminates, and obtains the primary product of reaction;The frequency of microwave
For 2.45GHZ-3GHZ;
4th procedure, by primary product take out, in the environment of being placed in 0-10 DEG C cool down, toward cool down after preliminary
Add PH=12 in product, temperature is the water of 90-100 DEG C, and primary product is stirred washing standing point
Layer, takes off a layer material;Repeat this process, until the PH=7-8 of lower floor's material;Then lower floor's material is carried out
Azeotropic distillation, steams remanent polarization organic solvent and water, obtains filter cake;Described filter cake methanol is dried after cleaning,
I.e. obtain nanoscale copper phthalocyanine pigments.
The technical scheme improved as the present invention, described polar organic solvent is that boiling point is more than the polarity of 200 DEG C and has
Machine solvent.
The technical scheme improved as the present invention, described polar organic solvent is Nitrobenzol or dimethyl sulfoxide.
The beneficial effects of the present invention is:
By ultrasonic and two kinds of reaction bonded technology of microwave, it is directly synthesized and produces nano-level pigment.Its technological principle
When being to utilize ultrasonic cavitation produce mechanically and chemically effect, make mass transfer, heat transfer, chemical bond fracture effect strong
Changing, microwave heating can make chemical substance be brought rapidly up within tens of seconds to a few minutes simultaneously, makes the face being immediately generated
Material granule is tiny to be had uniformly, particle diameter about 3-4nm, narrow particle size distribution, it is to avoid secondary nucleation, the most ultrasonic sky
Change effect can be stablized the granulation tissue of nanosized and be assembled.Synthetic reaction terminates, and recycles azeotropic dehydration technology,
Remove the moisture in suspension pigment, it is to avoid granules of pigments produces hard agglomeration, after being then peeled off organic solvent
It is dried, so that it may the most once obtain the hydrophobic micropowder nano-level pigment of soilless sticking.
Accompanying drawing explanation
The ultraviolet spectrogram of the nanoscale copper phthalocyanine pigments prepared by Fig. 1 present invention.
Detailed description of the invention
Purpose and technical scheme for making the embodiment of the present invention are clearer, below in conjunction with the embodiment of the present invention
Accompanying drawing 1, is clearly and completely described the technical scheme of the embodiment of the present invention.Obviously, described reality
Execute a part of embodiment rather than whole embodiments that example is the present invention.Reality based on the described present invention
Execute example, the every other enforcement that those of ordinary skill in the art are obtained on the premise of without creative work
Example, broadly falls into the scope of protection of the invention.
Those skilled in the art of the present technique are appreciated that unless otherwise defined, and all terms used herein (include
Technical term and scientific terminology) have with the those of ordinary skill in art of the present invention be commonly understood by identical
Meaning.Should also be understood that those terms defined in such as general dictionary should be understood that have with
The meaning that meaning in the context of prior art is consistent, and unless defined as here, will not be by ideal
Change or the most formal implication is explained.
Embodiment 1
A kind of method being directly synthesized nanoscale copper phthalocyanine pigments, comprises the technical steps that: by following weight portion
Nitrobenzol 280 parts, phthalic nitrile 56 parts, 13 parts of carbamide, ammonium molybdate 0.6 part, Cu-lyt. 11 parts
Add to being placed in the glass flask on supersonic generator stirring, be heated to material dissolution, mix homogeneously, its
Middle supersonic frequency is 80HZ, and the time is 30min;The material of mix homogeneously is placed in microwave in microwave reactor
Being heated to 180 DEG C, material reacts, and constant temperature keeps 20min, and reaction terminates, and obtains the preliminary product of reaction
Thing;The frequency of microwave is 2.45GHZ;Primary product is taken out, cools down in the environment of being placed in 0 DEG C, toward cooling
After primary product in add the water that PH=12, temperature are 90 DEG C, primary product is stirred washing quiet
Put layering, take off a layer material;Repeat this process, until the PH=7 of lower floor's material;Then lower floor's material is entered
Row azeotropic distillation, steams residual Nitrobenzol and water, obtains filter cake;Described filter cake methanol is dried after cleaning, i.e.
Obtaining nanoscale copper phthalocyanine pigments, and granules of pigments is uniformly dispersed, particle size average out to 3um, purity is
89%.
Embodiment 2
A kind of method being directly synthesized nanoscale copper phthalocyanine pigments, comprises the technical steps that: by following weight portion
Nitrobenzol 280 parts, phthalic nitrile 56 parts, 13 parts of carbamide, ammonium molybdate 0.6 part, Cu-lyt. 11 parts
Add to being placed in the glass flask on supersonic generator stirring, be heated to material dissolution, mix homogeneously, its
Middle supersonic frequency is 70HZ, and the time is 30min;The material of mix homogeneously is placed in microwave in microwave reactor
Being heated to 180 DEG C, material reacts, and constant temperature keeps 20min, and reaction terminates, and obtains the preliminary product of reaction
Thing;The frequency of microwave is 2.45GHZ;Primary product is taken out, cools down in the environment of being placed in 0 DEG C, toward cooling
After primary product in add the water that PH=12, temperature are 90 DEG C, primary product is stirred washing quiet
Put layering, take off a layer material;Repeat this process, until the PH=7 of lower floor's material;Then lower floor's material is entered
Row azeotropic distillation, steams residual Nitrobenzol and water, obtains filter cake;Described filter cake methanol is dried after cleaning, i.e.
The particle size obtaining phthalocyanine pigment is big, and skewness, and purity is 40%.
Embodiment 4
A kind of method being directly synthesized nanoscale copper phthalocyanine pigments, comprises the technical steps that: by following weight portion
Nitrobenzol 280 parts, phthalic nitrile 56 parts, 13 parts of carbamide, ammonium molybdate 0.6 part, Cu-lyt. 11 parts
Add to being placed in the glass flask on supersonic generator stirring, be heated to material dissolution, mix homogeneously, its
Middle supersonic frequency is 120HZ, and the time is 30min;The material of mix homogeneously is placed in microwave in microwave reactor
Being heated to 180 DEG C, material reacts, and constant temperature keeps 20min, and reaction terminates, and obtains the preliminary product of reaction
Thing;The frequency of microwave is 2.45GHZ;Primary product is taken out, cools down in the environment of being placed in 0 DEG C, toward cooling
After primary product in add the water that PH=12, temperature are 90 DEG C, primary product is stirred washing quiet
Put layering, take off a layer material;Repeat this process, until the PH=7 of lower floor's material;Then lower floor's material is entered
Row azeotropic distillation, steams residual Nitrobenzol and water, obtains filter cake;Described filter cake methanol is dried after cleaning, i.e.
Obtaining phthalocyanine pigment grain shape size uneven, and it is serious to reunite, purity is 45%.
Embodiment 5
A kind of method being directly synthesized nanoscale copper phthalocyanine pigments, comprises the technical steps that: by following weight portion
Nitrobenzol 280 parts, phthalic nitrile 56 parts, 13 parts of carbamide, ammonium molybdate 0.6 part, Cu-lyt. 11 parts
Add to being placed in the glass flask on supersonic generator stirring, be heated to material dissolution, mix homogeneously, its
Middle supersonic frequency is 80HZ, and the time is 30min;The material of mix homogeneously is placed in microwave in microwave reactor
Being heated to 180 DEG C, material reacts, and constant temperature keeps 20min, and reaction terminates, and obtains the preliminary product of reaction
Thing;The frequency of microwave is 2GHZ;Primary product is taken out, cools down in the environment of being placed in 0 DEG C, after cooling
Primary product in add the water that PH=12, temperature are 90 DEG C, primary product is stirred washing and stands
Layering, takes off a layer material;Repeat this process, until the PH=7 of lower floor's material;Then lower floor's material is carried out
Azeotropic distillation, steams residual Nitrobenzol and water, obtains filter cake;Described filter cake methanol is dried after cleaning, and to obtain final product
To phthalocyanine pigment reunion in bulk, purity is 50%.
Embodiment 6
A kind of method being directly synthesized nanoscale copper phthalocyanine pigments, comprises the technical steps that: by following weight portion
Nitrobenzol 280 parts, phthalic nitrile 56 parts, 13 parts of carbamide, ammonium molybdate 0.6 part, Cu-lyt. 11 parts
Add to being placed in the glass flask on supersonic generator stirring, be heated to material dissolution, mix homogeneously, its
Middle supersonic frequency is 80HZ, and the time is 30min;The material of mix homogeneously is placed in microwave in microwave reactor
Being heated to 180 DEG C, material reacts, and constant temperature keeps 20min, and reaction terminates, and obtains the preliminary product of reaction
Thing;The frequency of microwave is 4GHZ;Primary product is taken out, cools down in the environment of being placed in 0 DEG C, after cooling
Primary product in add the water that PH=12, temperature are 90 DEG C, primary product is stirred washing and stands
Layering, takes off a layer material;Repeat this process, until the PH=7 of lower floor's material;Then lower floor's material is carried out
Azeotropic distillation, steams residual Nitrobenzol and water, obtains filter cake;Described filter cake methanol is dried after cleaning, and to obtain final product
To micron order phthalocyanine pigment, and it is serious to reunite, and purity is 35%.
Embodiment 7
A kind of method being directly synthesized nanoscale copper phthalocyanine pigments, comprises the technical steps that: by following weight portion
Dimethyl sulfoxide 270 parts, phthalic nitrile 40 parts, 8 parts of carbamide, ammonium molybdate 0.3 part, Cu-lyt. 5
Part;Add to being placed in the glass flask on supersonic generator stirring, be heated to material dissolution, mix homogeneously,
Wherein ultrasound condition is: frequency 80HZ, and the time is 1h;The material of mix homogeneously is placed in microwave reactor
Microwave heating is to 190 DEG C, and material reacts, and constant temperature keeps 20min, and reaction terminates, and obtains at the beginning of reaction
Step product;The frequency of microwave is 3GHZ;Primary product is taken out, cools down in the environment of being placed in 0 DEG C, toward cold
But the primary product after adds the water that PH=12, temperature are 100 DEG C, is stirred washing also to primary product
Stratification, takes off a layer material;Repeat this process, until the PH=8 of lower floor's material;Then to lower floor's material
Carry out azeotropic distillation, steam residual dimethyl sulfoxide and water, obtain filter cake;Described filter cake methanol is dry after cleaning
Dry, i.e. obtain nanoscale copper phthalocyanine pigments, and granules of pigments is uniformly dispersed, particle size average out to 3um,
Purity is 80%.
Embodiment 8
A kind of method being directly synthesized nanoscale copper phthalocyanine pigments, comprises the technical steps that: by following weight portion
Dimethyl sulfoxide 280 parts, phthalic nitrile 60 parts, 15 parts of carbamide, ammonium molybdate 1 part, Cu-lyt. 12
Part;Add to being placed in the glass flask on supersonic generator stirring, be heated to material dissolution, mix homogeneously,
Wherein ultrasound condition is: frequency 80HZ, and the time is 30min;The material of mix homogeneously is placed in microwave reaction
In device, microwave heating is to 180 DEG C, and material reacts, and constant temperature keeps 20min, and reaction terminates, and is reacted
Primary product;The frequency of microwave is 2.5GHZ;Primary product is taken out, cools down in the environment of being placed in 0 DEG C,
In the primary product after cooling, add the water that PH=12, temperature are 95 DEG C, primary product is stirred water
Wash and stratification, take off a layer material;Repeat this process, until the PH=7 of lower floor's material;Then to lower floor
Material carries out azeotropic distillation, steams residual dimethyl sulfoxide and water, obtains filter cake;Described filter cake methanol cleans
Rear dry, i.e. obtain nanoscale copper phthalocyanine pigments, and granules of pigments is uniformly dispersed, particle size average out to
4um, purity is 78%.
Embodiment 9
A kind of method being directly synthesized nanoscale copper phthalocyanine pigments, comprises the technical steps that: by following weight portion
Dimethyl sulfoxide 277 parts, phthalic nitrile 42 parts, 12 parts of carbamide, ammonium molybdate 0.7 part, Cu-lyt. 7
Part;Add to being placed in the glass flask on supersonic generator stirring, be heated to material dissolution, mix homogeneously,
Wherein ultrasound condition is: frequency 87HZ, and the time is 45min;The material of mix homogeneously is placed in microwave reaction
In device, microwave heating is to 188 DEG C, and material reacts, and constant temperature keeps 20min, and reaction terminates, and is reacted
Primary product;The frequency of microwave is 2.7GHZ;Primary product is taken out, cools down in the environment of being placed in 0 DEG C,
In the primary product after cooling, add the water that PH=12, temperature are 95 DEG C, primary product is stirred water
Wash and stratification, take off a layer material;Repeat this process, until the PH=7 of lower floor's material;Then to lower floor
Material carries out azeotropic distillation, steams residual dimethyl sulfoxide and water, obtains filter cake;Described filter cake methanol cleans
Rear dry, i.e. obtain nanoscale copper phthalocyanine pigments, and granules of pigments is uniformly dispersed, particle size average out to
4um, purity is 75%.
In this application, lower floor's material being carried out azeotropic distillation, the polar organic solvent steamed and water are after separating the layers
Recyclable apply mechanically.
Additionally it is an advantage of the current invention that:
(1) due to use ultrasonic, microwave technology, make the granule of phthalocyanine pigment up to nanoscale, and
Granule is uniform, and this is difficult to accomplish with existing traditional technology method;
(2) response time and manufacturing process all greatly reduce than existing common technology;
(3) owing to have employed microwave heating technique, it is to avoid material is in glass container wall part of the body cavity above the diaphragm housing the heart and lungs junction phenomena
(4) the pigment impurity of present invention synthesis is few, and purity is high, good stability;
(5) pigment of present invention synthesis is the most common method energy resource consumption and quantity of three wastes subtract significantly
Few.
These are only embodiments of the present invention, it describes more concrete and detailed, but can not therefore understand
For the restriction to the scope of the claims of the present invention.It should be pointed out that, for the person of ordinary skill of the art,
Without departing from the inventive concept of the premise, it is also possible to make some deformation and improvement, these belong to the present invention
Protection domain.
Claims (3)
1. the method being directly synthesized nanoscale copper phthalocyanine pigments, it is characterised in that include that following technique walks
Rapid: first operation, weigh following material by weight: polar organic solvent 270-280 part, adjacent benzene two
Nitrile 40-60 part, carbamide 8-15 part, ammonium molybdate 0.3-1 part, Cu-lyt.;Wherein, the weight of Cu-lyt.
Amount part is the 1/8-1/5 of phthalic nitrile;
Second operation work, is uniformly mixed the material weighed on supersonic generator;The most ultrasonic
Condition is: frequency 80-95HZ, and the time is 30min-1h;
Three process, is placed in microwave reactor microwave heating to 180-190 DEG C by the material of mix homogeneously,
Material reacts, and constant temperature keeps 20min, and reaction terminates, and obtains the primary product of reaction;The frequency of microwave
For 2.45GHZ-3GHZ;
4th procedure, by primary product take out, in the environment of being placed in 0-10 DEG C cool down, toward cool down after preliminary
Add PH=12 in product, temperature is the water of 90-100 DEG C, and primary product is stirred washing standing point
Layer, takes off a layer material;Repeat this process, until the PH=7-8 of lower floor's material;Then lower floor's material is carried out
Azeotropic distillation, steams remanent polarization organic solvent and water, obtains filter cake;Described filter cake methanol is dried after cleaning,
I.e. obtain nanoscale copper phthalocyanine pigments.
A kind of method being directly synthesized nanoscale copper phthalocyanine pigments the most according to claim 1, its feature exists
In, described polar organic solvent is the polar organic solvent that boiling point is more than 200 DEG C.
A kind of method being directly synthesized nanoscale copper phthalocyanine pigments the most according to claim 1 and 2, its feature
Being, described polar organic solvent is Nitrobenzol or dimethyl sulfoxide.
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108164539A (en) * | 2017-12-29 | 2018-06-15 | 先尼科化工(上海)有限公司 | A kind of novel green phthalocyanine compound and preparation method thereof |
CN108299844A (en) * | 2017-12-29 | 2018-07-20 | 先尼科化工(上海)有限公司 | Novel solvable green phthalocyanine compound of one kind and preparation method thereof |
CN111334085A (en) * | 2020-04-08 | 2020-06-26 | 德州学院 | Graphene modification method of phthalocyanine blue pigment |
-
2016
- 2016-03-29 CN CN201610187828.1A patent/CN105838103A/en active Pending
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108164539A (en) * | 2017-12-29 | 2018-06-15 | 先尼科化工(上海)有限公司 | A kind of novel green phthalocyanine compound and preparation method thereof |
CN108299844A (en) * | 2017-12-29 | 2018-07-20 | 先尼科化工(上海)有限公司 | Novel solvable green phthalocyanine compound of one kind and preparation method thereof |
CN108164539B (en) * | 2017-12-29 | 2020-09-18 | 先尼科化工(上海)有限公司 | Green phthalocyanine compound and preparation method thereof |
CN111334085A (en) * | 2020-04-08 | 2020-06-26 | 德州学院 | Graphene modification method of phthalocyanine blue pigment |
CN111334085B (en) * | 2020-04-08 | 2021-07-23 | 德州学院 | Graphene modification method of phthalocyanine blue pigment |
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