CA1047492A - Organic dyes and method of production - Google Patents
Organic dyes and method of productionInfo
- Publication number
- CA1047492A CA1047492A CA247,694A CA247694A CA1047492A CA 1047492 A CA1047492 A CA 1047492A CA 247694 A CA247694 A CA 247694A CA 1047492 A CA1047492 A CA 1047492A
- Authority
- CA
- Canada
- Prior art keywords
- finely divided
- organic dye
- microns
- granular
- particle size
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0092—Dyes in solid form
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Abstract
ABSTRACT
A method for producing a granular organic dye material having an average particle size of 500 to 900 microns, preferably 500 to 700 microns, and the product thereof, in which finely divided dye material of the order of 20 microns is subjected to an ambient temperature pressure bonding, such as by rolling, to form a thin coherent sheet of material. The thin sheet of material is then mechanically comminuted, for example in a hammer mill, to produce the desired granular dye material with minimum of fines. The granular material and the fines are separated by an air separation device and the fines recirculated to the pressure bonding step.
A method for producing a granular organic dye material having an average particle size of 500 to 900 microns, preferably 500 to 700 microns, and the product thereof, in which finely divided dye material of the order of 20 microns is subjected to an ambient temperature pressure bonding, such as by rolling, to form a thin coherent sheet of material. The thin sheet of material is then mechanically comminuted, for example in a hammer mill, to produce the desired granular dye material with minimum of fines. The granular material and the fines are separated by an air separation device and the fines recirculated to the pressure bonding step.
Description
:
~(~47~9;Z
~` This invention relates to the production of organic dye materials in granular form. More particularly, this invention relates to the production of organic dye granules in the size range 100-1200 microns, from finely divided organic dye materials having a particle size of less than 20 microns Granular organic dye materials having an average particle size of 500 to 700 microns are particularly useful for incorporation into composite pour-castable smoke-producing compositions. As set forth in more detail /34_42 in copending Canadian application 259,735 filed August 24, 1976.
; 10 in the names of Couture and Duchesne, it has been found that the use of commercially available organic dye materials in powder form, with a particle size of 10 to 15 microns, limits the solids loading in smoke-producing compositions to about 75%. Above 75% the viscosity of the composition becomes excessive and pour casting is no longer practical.
Resort must be made to the more complicated and costly technique of compression or tamp casting. It will, of course, be appreciated that for maximum smoke generation as high a solids loading as possible is desirable, consistent with the desired handling, ignition and burning characteristics.
It has further been demonstrated, as set forth in the aforesaid Canadian patent application, that the solids loading in smoke-producing compositions can be increased to 80-86% without excessive increase in viscosity provided -: ~ /~0 the dye particles are in the range of 100 to ~K~microns with an average particle size of the order of.500 to 700~vm).
Heretofore, dye granules in the desired 500 to 700 micron average size xange have been virtually unobtainable except at prohibitive cost.
The method of production of such granular dye materials heretofore available consisted ofmelting the commercially available 10-15f~m powder, crystallizing it and milling to the desired size. Although this method, which is costly and which produces a large volume of powder below the preferred 500-600~ m size range which must be recycled, is acceptable for the production of granular l-amino-anthraquinone (l-AAQ), a preferred dye . '. : -.
.. . .
-` ~(34749Z
to produce orange smoke, it is not acceptable for other dyes which are used to produce red, green, yellow and violet smoke, l-AAQ is a single compound and has a relatively sharply defined melting point at 252 C.
Many other dyes, useful for smoke compasitions, are mixtures of compounds having different melting points. Heating such dye materials results in superheating and degradation of one component of the mixture before other components thereof reach their melting point.
It is, therefore, an ob~ect of the present invention to provide a relatively inexpensive method of preparing granular dye materials from finely divided particles thereof without the heating and melting steps heretofore employed and thus avoiding the degradation problems encourtered.
Thus, by one aspect of this invention there is provided a method for producing granular organic dye material from dry, finely divided particles thereof which comprises: (a) pressure bonding said dry, finely divided particles of a particle size less than 20 microns, so as to produce a substantially coherent mass of material; (b~ comminuting said coherent mass of material; and (c) recovering granular organic dye material in the particle size range of 100 to lOaO microns from said comminuted material, steps (a~ and (b) being performed at ambient temperature.
It will be appreciated that, as the present invention contem-plates only a compaction-milling procedure, involving only ambient temperature mechanical operations, the high temperature degradation problems of the prior art are avoided. It will be further appreciated that dye granules can be economically produced, using equipment readily available in industry, in substantially any desired size range and with a minimum of fine powder.
This invention will be described in more detail hereinafter with reference to the examples and to the drawings in which the sole figure represents a schematic flow diagram of the method according to the invention.
Referring now to the Figure, finely divided, commercially available :' ls.)47~3~
organic dye material 1 haying a particle size in the range up to about 20~ m is fed from a feed hopper 2 into the nip of a pair of rolls in rolling mill 4. The laminar product 5, ~hich i~ normally 1-5 sq. cm.
in area and 0.5 to 1.3 ~m thick depending upon the specific dye and roll settingsi~then fed to a relatively slowly rotating hammer mill 6, which produces particles in the range lO to 2000J~m, depending upon the shape and size of the holes in the grid in the cruahing chamber. A grid (not shown) with oblique holes 1.15 x 125 mm yielded an average size of the order of 600 ~m for all of the dyes tested. The discharge from the mill 6 passes into an air separator 7 and is ~ubJected to an air backdraft which carries the fines (-SO~m) and dust, usually only about 5~, to a cyclone 8 where they are recovered for recycling to the rolling mill 4.
The granules of desired size are passed through the separator and collect-ed separately in collector 9. It will be appreciated that the air draft at the venturi in separator 7 may be varied as desired, thereby closely controlling the size range of the granules collected. A supplemental venturi 10 and air ~et 11 may be provided between the separator 7 and cyclone 8, to effect a supplemental alr stream to carry over the fines.
Example l 10 Kg/hr of commercially available l-AAQ orange dye (-20~ m) was fed to a rolling mill having two rolls 25 cm long and 15 cm diameter, rotating at 20 rpm. The rolls were set 80 that they ~ust touched when the mill was running empty. The laminar material produced from the mill was 1-5 sq. cm. in area, had an average thickness of 0.6 mm and approached the theoretical density of the dye material. The laminar material was then fed to a Bantam '~i~ro Pulverizer" hammer mill. The mill was designed to operate at 14,000 rpm to produce a fine powder, however, it was found that reduction of the speed to 850 rpm, which corresponds closely to the minimum speed to maintain good clrculation in ~ ~-the crushing chamber, resulted in granules of an average size of 500~m (including 6% fines) in the output. The crusher was equipped with a grid containing oblique holes 1.15 x 125 ~m. The output ~rom the hammer mill ~4~45~Z
was passed to an air separator, where an air stream (created by the air jet through venturi 10 located between the separator 7 and the cyclone 8) separated the 6% fines, all below 53~vm, which were collected in a cyclone and recycled. The remaining 94% of the output was collected as granules having an average si7e of 620~m.
The procedure outlined above was repeated and comparable results were obtained using commercially available finely divided (less than 20,l~m) blue (1,4-dimethylamino anthraquinone~, red (Disperse Red-9, Colour Index, (C.I.) name for l-methylamino anthraquinone [l-MAAQ]) and violet (Dye Mix, Violet C.I. name for 20% Disperse Red-9, 80% 1,4 diamino dihydro anthraqui-none) dyes.
Example 2 Commercially available finely divided yellow (Smoke Yellow 6, C.I. name for 36% dye Vat Yellow 4, 64% benzanthrone) and green (Smoke Green 4 C.I. name for 70% solvent green 3, 20% benzanthrone, 10% Vat Yellow 4) dyes were treated according to the procedure of Example 1, but it was found that these dyes did not form the desired laminar material after a single pass through the rolls. The rolling step was, therefore, repeated and the resultant laminar material was crushed as in Example 1 with comparable results. It was found preferable to set the rolls 0.2 mm apart for both rolling steps when processing the yellow dye for ease of operation because of the particular nature and adherence of this dye.
Satisfactory results, comparable to those of Example 1, were achieved with the yellow dye.
It will be appreciated that many modifications to the process of the present invention may be practiced without departing from the scope thereof. For example, although rolling has been particularly described to achieve the desired pressure bonding, such bonding may be effected in many other ways known, per se, to those skilled in the art. For example, y~
~ 4 - , - 14~74~Z
pressing in a vertical or hori~ontal press and even extrusion may be employed. Similarly, the comminution step may be effected in other ways, such as ball or rod mills or even in a core crusher of suitable dimensions, and is not limited to the use of a hammer mill. The separation step, while preferably carried out in an air ~et may be effected in other ways conven-tional to the art.
- 4a -
~(~47~9;Z
~` This invention relates to the production of organic dye materials in granular form. More particularly, this invention relates to the production of organic dye granules in the size range 100-1200 microns, from finely divided organic dye materials having a particle size of less than 20 microns Granular organic dye materials having an average particle size of 500 to 700 microns are particularly useful for incorporation into composite pour-castable smoke-producing compositions. As set forth in more detail /34_42 in copending Canadian application 259,735 filed August 24, 1976.
; 10 in the names of Couture and Duchesne, it has been found that the use of commercially available organic dye materials in powder form, with a particle size of 10 to 15 microns, limits the solids loading in smoke-producing compositions to about 75%. Above 75% the viscosity of the composition becomes excessive and pour casting is no longer practical.
Resort must be made to the more complicated and costly technique of compression or tamp casting. It will, of course, be appreciated that for maximum smoke generation as high a solids loading as possible is desirable, consistent with the desired handling, ignition and burning characteristics.
It has further been demonstrated, as set forth in the aforesaid Canadian patent application, that the solids loading in smoke-producing compositions can be increased to 80-86% without excessive increase in viscosity provided -: ~ /~0 the dye particles are in the range of 100 to ~K~microns with an average particle size of the order of.500 to 700~vm).
Heretofore, dye granules in the desired 500 to 700 micron average size xange have been virtually unobtainable except at prohibitive cost.
The method of production of such granular dye materials heretofore available consisted ofmelting the commercially available 10-15f~m powder, crystallizing it and milling to the desired size. Although this method, which is costly and which produces a large volume of powder below the preferred 500-600~ m size range which must be recycled, is acceptable for the production of granular l-amino-anthraquinone (l-AAQ), a preferred dye . '. : -.
.. . .
-` ~(34749Z
to produce orange smoke, it is not acceptable for other dyes which are used to produce red, green, yellow and violet smoke, l-AAQ is a single compound and has a relatively sharply defined melting point at 252 C.
Many other dyes, useful for smoke compasitions, are mixtures of compounds having different melting points. Heating such dye materials results in superheating and degradation of one component of the mixture before other components thereof reach their melting point.
It is, therefore, an ob~ect of the present invention to provide a relatively inexpensive method of preparing granular dye materials from finely divided particles thereof without the heating and melting steps heretofore employed and thus avoiding the degradation problems encourtered.
Thus, by one aspect of this invention there is provided a method for producing granular organic dye material from dry, finely divided particles thereof which comprises: (a) pressure bonding said dry, finely divided particles of a particle size less than 20 microns, so as to produce a substantially coherent mass of material; (b~ comminuting said coherent mass of material; and (c) recovering granular organic dye material in the particle size range of 100 to lOaO microns from said comminuted material, steps (a~ and (b) being performed at ambient temperature.
It will be appreciated that, as the present invention contem-plates only a compaction-milling procedure, involving only ambient temperature mechanical operations, the high temperature degradation problems of the prior art are avoided. It will be further appreciated that dye granules can be economically produced, using equipment readily available in industry, in substantially any desired size range and with a minimum of fine powder.
This invention will be described in more detail hereinafter with reference to the examples and to the drawings in which the sole figure represents a schematic flow diagram of the method according to the invention.
Referring now to the Figure, finely divided, commercially available :' ls.)47~3~
organic dye material 1 haying a particle size in the range up to about 20~ m is fed from a feed hopper 2 into the nip of a pair of rolls in rolling mill 4. The laminar product 5, ~hich i~ normally 1-5 sq. cm.
in area and 0.5 to 1.3 ~m thick depending upon the specific dye and roll settingsi~then fed to a relatively slowly rotating hammer mill 6, which produces particles in the range lO to 2000J~m, depending upon the shape and size of the holes in the grid in the cruahing chamber. A grid (not shown) with oblique holes 1.15 x 125 mm yielded an average size of the order of 600 ~m for all of the dyes tested. The discharge from the mill 6 passes into an air separator 7 and is ~ubJected to an air backdraft which carries the fines (-SO~m) and dust, usually only about 5~, to a cyclone 8 where they are recovered for recycling to the rolling mill 4.
The granules of desired size are passed through the separator and collect-ed separately in collector 9. It will be appreciated that the air draft at the venturi in separator 7 may be varied as desired, thereby closely controlling the size range of the granules collected. A supplemental venturi 10 and air ~et 11 may be provided between the separator 7 and cyclone 8, to effect a supplemental alr stream to carry over the fines.
Example l 10 Kg/hr of commercially available l-AAQ orange dye (-20~ m) was fed to a rolling mill having two rolls 25 cm long and 15 cm diameter, rotating at 20 rpm. The rolls were set 80 that they ~ust touched when the mill was running empty. The laminar material produced from the mill was 1-5 sq. cm. in area, had an average thickness of 0.6 mm and approached the theoretical density of the dye material. The laminar material was then fed to a Bantam '~i~ro Pulverizer" hammer mill. The mill was designed to operate at 14,000 rpm to produce a fine powder, however, it was found that reduction of the speed to 850 rpm, which corresponds closely to the minimum speed to maintain good clrculation in ~ ~-the crushing chamber, resulted in granules of an average size of 500~m (including 6% fines) in the output. The crusher was equipped with a grid containing oblique holes 1.15 x 125 ~m. The output ~rom the hammer mill ~4~45~Z
was passed to an air separator, where an air stream (created by the air jet through venturi 10 located between the separator 7 and the cyclone 8) separated the 6% fines, all below 53~vm, which were collected in a cyclone and recycled. The remaining 94% of the output was collected as granules having an average si7e of 620~m.
The procedure outlined above was repeated and comparable results were obtained using commercially available finely divided (less than 20,l~m) blue (1,4-dimethylamino anthraquinone~, red (Disperse Red-9, Colour Index, (C.I.) name for l-methylamino anthraquinone [l-MAAQ]) and violet (Dye Mix, Violet C.I. name for 20% Disperse Red-9, 80% 1,4 diamino dihydro anthraqui-none) dyes.
Example 2 Commercially available finely divided yellow (Smoke Yellow 6, C.I. name for 36% dye Vat Yellow 4, 64% benzanthrone) and green (Smoke Green 4 C.I. name for 70% solvent green 3, 20% benzanthrone, 10% Vat Yellow 4) dyes were treated according to the procedure of Example 1, but it was found that these dyes did not form the desired laminar material after a single pass through the rolls. The rolling step was, therefore, repeated and the resultant laminar material was crushed as in Example 1 with comparable results. It was found preferable to set the rolls 0.2 mm apart for both rolling steps when processing the yellow dye for ease of operation because of the particular nature and adherence of this dye.
Satisfactory results, comparable to those of Example 1, were achieved with the yellow dye.
It will be appreciated that many modifications to the process of the present invention may be practiced without departing from the scope thereof. For example, although rolling has been particularly described to achieve the desired pressure bonding, such bonding may be effected in many other ways known, per se, to those skilled in the art. For example, y~
~ 4 - , - 14~74~Z
pressing in a vertical or hori~ontal press and even extrusion may be employed. Similarly, the comminution step may be effected in other ways, such as ball or rod mills or even in a core crusher of suitable dimensions, and is not limited to the use of a hammer mill. The separation step, while preferably carried out in an air ~et may be effected in other ways conven-tional to the art.
- 4a -
Claims (9)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A method for producing granular organic dye material from dry, finely divided particles thereof which comprises:
(a) pressure bonding said dry, finely divided particles of a particle size less than 20 microns, so as to produce a substantially coherent mass of material;
(b) comminuting said coherent mass of material; and (c) recovering granular organic dye material in the particle size range of 100 to 1000 microns from said comminuted material, steps (a) and (b) being performed at ambient temperature.
(a) pressure bonding said dry, finely divided particles of a particle size less than 20 microns, so as to produce a substantially coherent mass of material;
(b) comminuting said coherent mass of material; and (c) recovering granular organic dye material in the particle size range of 100 to 1000 microns from said comminuted material, steps (a) and (b) being performed at ambient temperature.
2. A method as claimed in claim 1 wherein said pressure bonding is effected by passing said finely divided material between at least one pair of axially aligned rotating rolls, thereby producing a coherent laminar sheet of material.
3. A method as claimed in claim 1 wherein step (b) is effected in a hammer mill.
4. A method as claimed in claim 1, 2 or 3 wherein said comminuted material is subjected to air separation in step (c) thereby separating said granular material from finely divided dust particles which are recycled through step (a).
5. A method as claimed in claim 1, 2 or 3 wherein the particle size of said finely divided organic dye material is 10-15 microns.
6. A method as claimed in claim 1, 2 or 3 wherein said organic dye material-is selected from the group comprising 1-amino-anthraquinone, 1,4-dimethylamino anthraquinone, Disperse Red 9 and Dye Mix, Violet.
7. A method as claimed in claim 2, wherein said finely divided material is passed through at least two pairs of rotating rolls.
8. A method as claimed in claim 7 wherein said organic dye material is selected from the group comprising: Smoke Yellow 6 and Smoke Green 4.
9. A method as claimed in claim 1, 2 or 3 wherein sufficient pressure is applied in said pressure bonding step so as to densify finely divided organic dye material to substantially the theoretical density thereof.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA247,694A CA1047492A (en) | 1976-03-11 | 1976-03-11 | Organic dyes and method of production |
| GB1049877A GB1558153A (en) | 1976-03-11 | 1977-03-11 | Granulation of organic dyes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA247,694A CA1047492A (en) | 1976-03-11 | 1976-03-11 | Organic dyes and method of production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1047492A true CA1047492A (en) | 1979-01-30 |
Family
ID=4105441
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA247,694A Expired CA1047492A (en) | 1976-03-11 | 1976-03-11 | Organic dyes and method of production |
Country Status (2)
| Country | Link |
|---|---|
| CA (1) | CA1047492A (en) |
| GB (1) | GB1558153A (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI20070521L (en) | 2006-11-10 | 2008-05-11 | Atacama Labs Oy | Grains, tablets and granulation process |
| FI20080353A0 (en) * | 2008-05-09 | 2008-05-09 | Atacama Labs Oy | Process for preparing a tablet with extra high drug content |
| FI20080355A0 (en) * | 2008-05-09 | 2008-05-09 | Atacama Labs Oy | Process for making tablets containing metformin |
| US8951562B2 (en) | 2006-11-10 | 2015-02-10 | Atacama Labs Oy | Method and apparatus or dry granulation |
| FI20080346A0 (en) * | 2008-05-09 | 2008-05-09 | Atacama Labs Oy | Process for making a tablet containing additives |
| CA2723409C (en) * | 2008-05-09 | 2016-11-08 | Atacama Labs Oy | Method and apparatus for dry granulation |
-
1976
- 1976-03-11 CA CA247,694A patent/CA1047492A/en not_active Expired
-
1977
- 1977-03-11 GB GB1049877A patent/GB1558153A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1558153A (en) | 1979-12-19 |
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