CN102816457B - Red azo condensation mixed pigment with high tinting strength and its preparation method - Google Patents
Red azo condensation mixed pigment with high tinting strength and its preparation method Download PDFInfo
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- CN102816457B CN102816457B CN2012103027914A CN201210302791A CN102816457B CN 102816457 B CN102816457 B CN 102816457B CN 2012103027914 A CN2012103027914 A CN 2012103027914A CN 201210302791 A CN201210302791 A CN 201210302791A CN 102816457 B CN102816457 B CN 102816457B
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- 239000000049 pigment Substances 0.000 title claims abstract description 57
- 238000009833 condensation Methods 0.000 title claims abstract description 33
- 230000005494 condensation Effects 0.000 title claims abstract description 33
- 238000002360 preparation method Methods 0.000 title claims description 8
- 150000004985 diamines Chemical class 0.000 claims abstract description 50
- 150000001263 acyl chlorides Chemical class 0.000 claims abstract description 46
- 239000000203 mixture Substances 0.000 claims abstract description 30
- 150000001412 amines Chemical class 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 239000004033 plastic Substances 0.000 abstract description 3
- 229920003023 plastic Polymers 0.000 abstract description 3
- 238000007639 printing Methods 0.000 abstract description 3
- 238000004040 coloring Methods 0.000 abstract description 2
- 239000003973 paint Substances 0.000 abstract description 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 21
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 14
- 239000000975 dye Substances 0.000 description 10
- 238000005859 coupling reaction Methods 0.000 description 8
- 230000008878 coupling Effects 0.000 description 7
- 238000010168 coupling process Methods 0.000 description 7
- 238000010792 warming Methods 0.000 description 6
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- -1 acyl chlorides compound Chemical class 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 229920001903 high density polyethylene Polymers 0.000 description 3
- 239000004700 high-density polyethylene Substances 0.000 description 3
- 238000001746 injection moulding Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- PMVZTQWNRAVKLK-UHFFFAOYSA-N 1-n,4-n-dichlorobenzene-1,4-diamine Chemical class ClNC1=CC=C(NCl)C=C1 PMVZTQWNRAVKLK-UHFFFAOYSA-N 0.000 description 2
- QAYVHDDEMLNVMO-UHFFFAOYSA-N 2,5-dichlorobenzene-1,4-diamine Chemical compound NC1=CC(Cl)=C(N)C=C1Cl QAYVHDDEMLNVMO-UHFFFAOYSA-N 0.000 description 2
- 229910010413 TiO 2 Inorganic materials 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 229960005081 diclofenamide Drugs 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000001054 red pigment Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- LXASMCOZTLEVFY-VXPUYCOJSA-N C=C(C(Cl)=C)/N=N\c(c(cccc1)c1cc1C(Cl)=C)c1O Chemical compound C=C(C(Cl)=C)/N=N\c(c(cccc1)c1cc1C(Cl)=C)c1O LXASMCOZTLEVFY-VXPUYCOJSA-N 0.000 description 1
- 0 CC(CC*)=C(C(C)=C)N=NC1=CC(Cl)=CCC1Cl Chemical compound CC(CC*)=C(C(C)=C)N=NC1=CC(Cl)=CCC1Cl 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Abstract
The invention relates to a red azo condensation mixed pigment, which is formed by condensation of an acyl chloride mixture composed of the acyl chloride shown in the following formula (3) and the acyl chloride shown in formula (4) and a diamine mixture composed of the diamine shown in the following formula (6), the diamine shown in formula (7), as well as the diamine shown in formula (8). Specifically, the acyl chloride mixture and the diamine mixture are in a mole ratio of 2:1, the acyl chloride shown in formula (3) and the acyl chloride shown in formula (4) are in a mole ratio of 15-85:85-15, and the diamine shown in formula (6), the diamine shown in formula (7) as well as the diamine shown in formula (8) are in a mole ratio of 0-30:5-60:40-95. The mixed pigment has high coloring strength, good vividness, high dispersibility, good heat resistance, high transparency, and has tinting strength enhanced by over 10% compared with that of pigments prepared from a single azo component, so that it can be used in plastics, printing ink and paints.
Description
Technical field
The present invention relates to pigment, be specifically related to the preparation process of red azo condensation hybrid pigment of high tinctorial strength, high-clarity and Gao Yandu and the detection of application performance.
Background technology
Azo pigment refers in chemical structure the pigment dyestuff that contains azo-group (N=N-).The classical pigment of red monoazo is class cheapness and the higher pigment dyestuff of tinting strength, and they have certain fast light and weather-proof fastness and are applicable in paint and printing ink.But, while using in plastics, the Red Classic monoazo pigment at high temperature easily occurs to decompose or the crystal variation causes variable color, thereby cause tinting strength to descend, and resistance to migration is poor, the coloring intensity of the existing classical monoazo pigment of azo condensation pigment, have again excellent fast light, weather-proof and thermotolerance, and the red pigment the present invention relates to is azo condensation pigment.
The preparation of relevant this class pigment, document GB1595489 proposes: the mixture that acyl chlorides compound as follows forms by the 2mol structural formula; With
A kind of in 1mol structural formula diamines as follows carries out condensation,
The pigment composition made has tinctorial property and gorgeous degree preferably, adopts the mixture of diamines but the document is thought, prepared pigment composition does not have good performance.
Document US005883167A proposes: adopt independent a kind of acyl chlorides compound as follows; With
The diamines mixed according to different ratio carries out the mixture of the pigment that condensation makes, can improve tinctorial strength and the vividness of pigment, the pigment made that is better than single acyl chlorides compound and independent diamines of its successful, equally also be better than the simple physical mixed of two kinds of different pigment.
Summary of the invention
The inventor finds through research, the acyl chlorides compound be mixed with according to certain ratio by the different intermediate para-dye that will prepare according to conventional method, the diamines mixed from ratio according to different under certain conditions carry out condensation obtain having high tinctorial strength and gorgeous degree gold-tinted red azo condensation pigment and blue light red azo condensation pigment, complete thus the present invention.
The first purpose of the present invention is to provide a kind of azo condensation hybrid pigment of redness, and it is by the acyl chlorides mixture with acyl chlorides shown in acyl chlorides shown in following formula 3 and formula 4,
Formula (3) formula (4)
With the two amine mixt condensations with diamines shown in diamines shown in diamines shown in following formula 6, formula 7 and formula 8, form,
formula (6)
formula (7)
Wherein, mol ratio (the acyl chlorides mixture: two amine mixt)=2: 1,
Mol ratio (acyl chlorides shown in formula 3: acyl chlorides shown in formula 4)=15-85:85-15,
Mol ratio (diamines shown in formula 6: diamines shown in formula 7: diamines shown in formula 8)=0-30: 5-60: 40-95.
The second purpose of the present invention is to provide the described red azo condensation of above-mentioned the first purpose hybrid pigment, wherein, and mol ratio (acyl chlorides shown in formula 3: acyl chlorides shown in formula 4)=90:10, or 15:85.
The 3rd purpose of the present invention is to provide the described red azo condensation of above-mentioned the first purpose hybrid pigment, wherein, and mol ratio (diamines shown in formula 6: diamines shown in formula 7: diamines shown in formula 8)=10:10:80, or 25:25:50; Perhaps 0:15:85.
The 4th purpose of the present invention is to provide the preparation method of above-mentioned red azo condensation hybrid pigment, and the method is by 100-180 ℃ of temperature, and acyl chlorides mixture and two amine mixt couplings are carried out.
Can be prepared acyl chlorides and diamines according to this area ordinary method.
As acyl chlorides, can also can prepare according to conventional methods by commercial acquisition, for example, by arylamine and 2, the middle dyestuff that 3 acid (2-hydroxyl-3-naphthoic acid) coupling obtains, in the orthodichlorobenzene solvent, is warming up to 80-85 ℃, with sulfur oxychloride, reacts, filter, the orthodichlorobenzene rinsing, obtain acyl chlorides.
As diamines, can prepare according to the method for conventional nitro thing reduction amino substance, for example, referring to Chen Yonggen, the development of 2,5-dichloro-p-phenylenediamine, [J] dyestuff and dyeing, 1987, vol 5:45-48; Cao Xuezeng, Wang Xueying, Chen Aiying, the research of Ursol D manufacturing condition, [J] applies chemical industry, 2002, (05)).
According to red azo condensation hybrid pigment provided by the invention, vividness is good, and tinctorial strength is high, and transparency is high, and dispersed high, thermotolerance is good, can be for plastics, printing ink and coating.
Embodiment
Below describe the present invention, the features and advantages of the invention will become more clear, clear and definite along with these descriptions.
In red azo condensation pigment according to the present invention, with the mixture of acyl chlorides shown in acyl chlorides shown in formula 3 and formula 4, and two amine mixt of diamines shown in diamines shown in diamines shown in formula 6, formula 7 and formula 8 are that the raw material coupling forms.
Research is found, two amine mixt)=2: 1 when mol ratio (acyl chlorides mixture:, mol ratio (acyl chlorides shown in formula 3: acyl chlorides shown in formula 4)=15-85:85-15, and mol ratio (diamines shown in formula 6: diamines shown in formula 7: diamines shown in formula 8)=0-30: 5-60: during 40-95, gained red azo condensation pigment has excellent performance.
Can infer, when the acyl chlorides mixture is reacted with two amine mixt, obtaining take pigment shown in formula (9) is main body, and formula (10,11,12) etc. is auxiliary mixture:
One preferred embodiment in, mol ratio (acyl chlorides shown in formula 3: acyl chlorides shown in formula 4)=90:10, or 15:85.
One preferred embodiment in, mol ratio (diamines shown in formula 6: diamines shown in formula 7: diamines shown in formula 8)=10:10:80, or 25:25:50; Perhaps 0:15:85.
In a preferred embodiment, at 100-120 ℃, preferably, at 110 ℃ of temperature, acyl chlorides mixture and two amine mixt carry out coupled reaction, obtain the red azo condensation pigment.
embodiment
Below further describe the present invention by specific examples.
Embodiment 1
Will be by 2, 5-dichlorphenamide bulk powder and 2, the middle dyestuff 3.61g that 3 acid (2-hydroxyl-3-naphthoic acid) coupling obtains, with by the chloro-5-5-trifluoromethylaniline of 2-and 2, 3 acid (the middle dyestuff 35.5g that 2-hydroxyl-3-naphthoic acid coupling obtains, under agitation drop in 260g orthodichlorobenzene solvent, be warming up to 80-85 ℃, the 16.6g sulfur oxychloride was splashed in 10-15 minute, be incubated 30 minutes, then reactant is warming up to 115-120 ℃, keep 1 hour, be cooled to 5-10 ℃, filter, a small amount of orthodichlorobenzene rinsing for filter cake, obtain the acyl chlorides mixture, through the thin-layer chromatography detection by quantitative, shown in formula 3 and formula 4, the ratio of acyl chlorides is 1: 9.
The acyl chlorides mixture thing of the above-mentioned preparation of 35g is under agitation put in the 250g orthodichlorobenzene, be warming up to 110 ℃, by 0.46g Ursol D, the adjacent chlorine Ursol D of 0.61g and 6.08g 2,5 dichloro-p-phenylenediamines join in the 50g orthodichlorobenzene and after being warming up to 110 ℃, in within 2-3 minute, joining the o-dichlorobenzene solution of acyl chlorides mixture, add rear insulation 30 minutes, then be warming up to 140-145 ℃, keep 4 hours.Gained material cooling down, to room temperature, is filtered, and filter cake is washed with 100g methyl alcohol, then washing, and filter cake, 90-95 ℃ of oven dry, obtains about 38.7g red pigment mixture, yield 99.05%.
Embodiment 2
Prepare the red azo condensation pigment with method similar to Example 1, difference is: use by 2,5-dichlorphenamide bulk powder and 2, the middle dyestuff 30.68g that 3 acid (2-hydroxyl-3-naphthoic acid) coupling obtains and by the chloro-5-5-trifluoromethylaniline of 2-and 2, the middle dyestuff 5.92g that 3 acid (2-hydroxyl-3-naphthoic acid) coupling obtains, dyestuff in the middle of the mixing in alternate embodiment 1.
Embodiment 3
Prepare the red azo condensation pigment with method similar to Example 1, difference is: use 1.15g Ursol D, the adjacent chlorine Ursol D of 1.53g and 3.8g2,5 dichloro-p-phenylenediamines replace the mixture of the diamines in the above embodiments 1.
Embodiment 4
Prepare the red azo condensation pigment with method similar to Example 2, difference is: use 1.15g Ursol D, the adjacent chlorine Ursol D of 1.53g and 3.8g2,5 dichloro-p-phenylenediamines replace the mixture of the diamines in the above embodiments 2.
Embodiment 5
Prepare the red azo condensation pigment with method similar to Example 2, difference is: 2 of the adjacent chlorine Ursol D of use 5.2g and 1.14g, the mixture of 5-dichloro-p-phenylenediamine replaces two amine mixt in embodiment 2.
test example
compare coloured light, intensity and thermotolerance in polyethylene
Getting gained red azo condensation pigment in embodiment 1-5 is tested, testing standard is selected respectively PVFast Scarlet 4RF (C.I. Pigment red 242, Clariant), Cromophtal Scarlet RN(C.I. Pigment red 144, Ciba), Cromophtal Red BN(C.I. Pigment red 166, Ciba).
Coloured light comparative approach: get 0.2 gram pigment sample, evenly spread to 200 gram HDPE(2911 types), in resin, in 200-220 ℃ of moulding on injection moulding machine, then use under D65/10 ° of color measurement instrument (thinking scholar) the relatively color distortion of each pigment.The results are shown in following table 1.
Intensity comparative approach: get 0.2 gram pigment sample, add 1.0 gram TiO
2(E.I.Du Pont Company, R-902), evenly spread in 200 gram HDPE resins, in 200-220 ℃ of moulding on injection moulding machine, then with the color measurement instrument strength difference of each pigment relatively.The results are shown in following table 1.
The detection method of the transparency: get 0.1 gram pigment sample, the 50gPVC resin, be placed on the two roller machines of 140-150 ℃ membrane 10 minutes, then membrane, use the vulcanizing press compressing tablet, standard specimen and sample are forced together, then pass through the difference of the more transparent degree of method of range estimation.The results are shown in following table 1.
Method for Measuring Heat-resistibility: get 0.2 gram pigment sample, add 1.0 gram TiO
2(E.I.Du Pont Company, R-902), evenly spread in 200 gram HDPE resins, keeps 5min under 280 ℃, moulding on injection moulding machine.Detect heating front and back chromatic aberration with color measurement instrument.Thermally-stabilised data are △ E changing value.The results are shown in following table 1.
Table 1 coloured light, intensity and thermotolerance detected result
As shown in Table 1, in example 1 and example 3, tinctorial strength and the Pigment red 242 of the red hybrid pigment of gained more all improve more than 10%, all gorgeous than Pigment red 242 on coloured light, and transparency obviously lowers, and thermotolerance is suitable with it.Example 1 slightly is better than example 1 with the properties of example 3 comparative examples 3 simultaneously.
On the mixture of the pigment of preparation and corresponding standard comparison intensity, obvious rising is arranged in embodiment 2,4, obvious variation is also arranged on its form and aspect, gorgeous degree tool is greatly improved, and the transparency is all obviously lower.From heat-resisting stable data, its thermotolerance and standard are more suitable in addition.Example 2 slightly is better than example 2 with the properties of example 4 comparative examples 4 simultaneously.
In example 5, the tinctorial strength of the red hybrid pigment of gained and Pigment red 144 comparison properties also all are significantly improved, the trend of variation and result and above coming to the same thing.
Abovely by embodiment and preferred embodiment, describe the present invention; but should understand; scope of the present invention is not limited to above-mentioned explanation; in the case of without departing from the spirit and scope of protection of the present invention; those skilled in the art can do various modifications, replacement or improvement to the present invention, and these equivalent form of values are equally in the application's appended claims limited range.
Claims (5)
1. the azo condensation hybrid pigment of a redness, it is by the acyl chlorides mixture with acyl chlorides shown in acyl chlorides shown in following formula 3 and formula 4,
With the two amine mixt condensation at 100-180 ℃ of temperature with diamines shown in diamines shown in diamines shown in following formula 6, formula 7 and formula 8, form,
Wherein, the acyl chlorides mixture: the mol ratio=2:1 of two amine mixt,
Acyl chlorides shown in formula 3: the mol ratio=15-85:85-15 of acyl chlorides shown in formula 4,
Diamines shown in formula 6: diamines shown in formula 7: the mol ratio=0-30:5-60:40-95 of diamines shown in formula 8.
2. the azo condensation hybrid pigment of redness according to claim 1, wherein, acyl chlorides shown in formula 3: the mol ratio=15:85 of acyl chlorides shown in formula 4.
3. the azo condensation hybrid pigment of redness according to claim 1, wherein, diamines shown in formula 6: diamines shown in formula 7: the mol ratio=10:10:80 of diamines shown in formula 8, or 25:25:50; Perhaps 0:15:85.
4. according to the preparation method of the azo condensation hybrid pigment of the described redness of any one in claim 1-3,
The method is passed through at 100-180 ℃ of temperature, by the acyl chlorides mixture with acyl chlorides shown in acyl chlorides shown in following formula 3 and formula 4,
With the two amine mixt condensations with diamines shown in diamines shown in diamines shown in following formula 6, formula 7 and formula 8, carry out,
Wherein, the acyl chlorides mixture: the mol ratio=2:1 of two amine mixt,
Acyl chlorides shown in formula 3: the mol ratio=15-85:85-15 of acyl chlorides shown in formula 4,
Diamines shown in formula 6: diamines shown in formula 7: the mol ratio=0-30:5-60:40-95 of diamines shown in formula 8.
5. method according to claim 4, the method is by 110 ℃ of temperature, and acyl chlorides mixture and two amine mixt condensations are carried out.
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| CN2012103027914A CN102816457B (en) | 2012-08-23 | 2012-08-23 | Red azo condensation mixed pigment with high tinting strength and its preparation method |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1595489A (en) * | 1976-12-31 | 1981-08-12 | Ciba Geigy Ag | Process for the production of azo pigments |
| CN1173520A (en) * | 1996-07-31 | 1998-02-18 | 西巴特殊化学品控股有限公司 | Process for preparation of highly coloured diazo pigment mixtures |
| EP1516896A1 (en) * | 2003-09-22 | 2005-03-23 | Fuji Photo Film Co., Ltd. | Organic pigment fine-particle, and method of producing the same |
| CN1854202A (en) * | 2005-04-19 | 2006-11-01 | 大日精化工业株式会社 | Pigment dispersants and their use |
-
2012
- 2012-08-23 CN CN2012103027914A patent/CN102816457B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1595489A (en) * | 1976-12-31 | 1981-08-12 | Ciba Geigy Ag | Process for the production of azo pigments |
| CN1173520A (en) * | 1996-07-31 | 1998-02-18 | 西巴特殊化学品控股有限公司 | Process for preparation of highly coloured diazo pigment mixtures |
| EP1516896A1 (en) * | 2003-09-22 | 2005-03-23 | Fuji Photo Film Co., Ltd. | Organic pigment fine-particle, and method of producing the same |
| CN1854202A (en) * | 2005-04-19 | 2006-11-01 | 大日精化工业株式会社 | Pigment dispersants and their use |
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Effective date of registration: 20200507 Address after: 114225, No. eight road, Teng Ao Economic Development Zone, Liaoning, Anshan Patentee after: ANSHAN HIFICHEM Co.,Ltd. Address before: 257299 No.8, Yanghe Road, Hekou District, Dongying City, Shandong Province Patentee before: DONGYING TIANZHENG CHEMICAL Co.,Ltd. |