CN105646278A - Rosinamino-bisdiazo condensation compound and preparation method thereof - Google Patents
Rosinamino-bisdiazo condensation compound and preparation method thereof Download PDFInfo
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- CN105646278A CN105646278A CN201610131583.0A CN201610131583A CN105646278A CN 105646278 A CN105646278 A CN 105646278A CN 201610131583 A CN201610131583 A CN 201610131583A CN 105646278 A CN105646278 A CN 105646278A
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
- C07C245/02—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides
- C07C245/06—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings
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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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/40—Preparation of azo dyes from other azo compounds by substituting hetero atoms by radicals containing other hetero atoms
Abstract
The invention discloses a rosinamino-bisdiazo condensation compound and a preparation method thereof. The rosinamino-bisdiazo condensation compound is shown as the below structural formula, wherein each of X and Y refers to fatty amino or arylamino. The rosinamino-bisdiazo condensation compound and the preparation method thereof have the advantages that specific fatty amine is added into a pigment yellow 93 condensation amidation process to synthesize the bisdiazo condensation compound by crystal mixing, and the bisdiazo condensation compound is stronger in green ray, remarkably improved in transparency and equivalent to existing pigment yellow 93 in heat resistance, solvent resistance, dispersity and rheological property on printing ink, thereby being applicable to highly-transparent printing ink.
Description
Technical field
The invention belongs to chemical dye field, be specifically related to a kind of disazo condensation compound and preparation method thereof.
Background technology
Biacetyl acetanilide azo condensation pigment couples a replacement aromatic ring again by amido link on biacetyl acetophenone amine pigment molecule basis at molecule two ends. This type of pigment, its molecular weight is big, and tinting strength, tinting power and fastness ability are stronger, especially more amide group is introduced, making compound be more likely formed in molecule and intermolecular hydrogen bonding, such molecular structure substantially improves every fastness ability, particularly thermostability and the solvent resistance of pigment. In coloring plastic, resistance to migration improves a lot. But owing to production cost is higher, therefore price is high, is mainly used in the occasion of top grade. Wherein pigment yellow 93 shows a kind of bright green light yellow, due to the thermostability of its brilliance, light resistance and good resistance to migration, has good application, be also widely used in plastic pvc, PP and LDPE in high-grade printing-ink, sedan car top coat.
Patent US3413279 discloses a kind of preparation method of yellow 93, the method by the diazol of diazo component 3-amino-4 chlorobenzoic acid and coupling component 2-chloro-5-methyl biacetyl acetyl-p-phenylenediamine at 105-110 DEG C in o-dichlorohenzene coupling prepare bisazo dicarboxylic acids intermediate, owing to the method is inhomogeneous reaction, causing that reaction is difficult to completely, productivity is relatively low.
The pigmentation method of pigment yellow 93 disclosed in patent US5194088. Crude pigment product, anhydrous sodium sulfate and steel ball are placed in ball grinder by the method, ball milling 48h under room temperature. Treat that ball milling is complete, under room temperature, ball milling crude product is processed in dimethyl sulfoxide 2h, through hot water making beating washing, dry can obtain pigment yellow 93 product.
According to market survey, although yellow 93 have high-fire resistance, good resistance to migration, the transparency of pigment yellow 93 needs the property improved, current Huang 93 adopts the preparation method disclosed in foregoing invention and pigmentation method, the product transparency obtained is still not satisfactory, for disazo condensation class pigment, it, by the particle adjustment of self, is difficult to there is breakthrough progress in the transparency. Present invention introduces the synthesis mode of mixed crystal, to obtain high transparent, thermostability has the excellent derivant being greatly improved simultaneously.
Summary of the invention
In order to overcome the problems referred to above, disazo pigment and preparation method thereof has been carried out studying with keen determination by the present inventor, obtain a kind of green glow disazo condensation compound significantly improved higher, transparent, on its thermostability, solvent resistance, dispersibility, ink, rheological characteristic is all suitable with existing pigment yellow 93, it is adaptable in the ink of the high grade of transparency.
It is an object of the invention to provide following aspect:
(1) the structure such as disazo condensation compound shown in formula I,
Wherein, X, Y are fat amido or aryl amine,
Containing aromatic hydrocarbons substituent group in described fatty amine based structures formula, it is preferable that containing C4��C20Aromatic hydrocarbons substituent group, and/or
Described aryl amine is substituted or unsubstituted anilino-, it is preferred to by one or more replaced anilino-of alkyl, alkoxyl or halogen atom;
(2) compound as described in above-mentioned (1), it is characterised in that
Containing C in described fatty amine based structures formula8��C16Aromatic hydrocarbons substituent group, and/or
Described aryl amine is by the replaced anilino-of methyl and/or chlorine atom;
(3) compound as described in above-mentioned (1) or (2), it is characterised in that
In formula I, X, Y are selected from group as shown in formula II or formula III, and are group shown in formula II during X, Y difference,
(4) compound as described in one of above-mentioned (1)��(3), it is characterised in that
In formula I, X is group shown in formula II for such as group shown in formula III and Y, or, X is group shown in formula III for such as group shown in formula II and Y,
Preferably, the compound that formula I is as follows:
(5) one prepares the method for compound as described in one of above-mentioned (1)��(4), with fatty amine and arylamine, the such as compound shown in formula IV is carried out condensation reaction, obtains described disazo condensation compound,
Containing aromatic hydrocarbons substituent group in described fatty amine structural formula, it is preferable that containing C4��C20Aromatic hydrocarbons substituent group, and/or
Described arylamine is substituted or unsubstituted aniline, it is preferred to by one or more replaced aniline of alkyl, alkoxyl or halogen atom;
(6) method as described in above-mentioned (5), it is characterised in that
Containing C in described fatty amine structural formula8��C16Aromatic hydrocarbons substituent group, and/or
Described arylamine is by the replaced aniline of methyl and/or chlorine atom;
(7) method as described in above-mentioned (5) or (6), it is characterised in that
The mole of described fatty amine is the 1��50% of arylamine mole, it is preferable that 3��30%, more preferably 5��20%;
(8) method as described in one of above-mentioned (5)��(7), it is characterised in that the method comprises the following steps:
Step 1, the such as compound shown in formula IV is dissolved in solvent,
Step 2, it is added thereto to fatty amine and arylamine, the lower insulation reaction of heating,
Step 3, reaction are lowered the temperature after terminating, are filtered, and obtain described compound.
(9) method as described in above-mentioned (8), it is characterised in that
In step 1, described solvent is halogeno-benzene or alkylbenzene, it is preferred to dichloro-benzenes, trichloro-benzenes, dimethyl benzene or trimethylbenzene, and/or
Preferably it is initially charged fatty amine, adds arylamine;
(10) such as above-mentioned (5) to the method as described in one of (9), it is characterised in that
In step 2, react 0.5��10 hour at 100��200 DEG C, it is preferable that react 1��6 hour at 120��180 DEG C, react 2��4 hours at 140��160 DEG C.
The present invention is had the advantage that to include:
(1) present invention adds specific fatty amine in the pigment yellow 93 amidated process of condensation, a kind of disazo condensation compound of mixed crystal synthesis, its green glow is higher, the transparency significantly improves, on thermostability, solvent resistance, dispersibility, ink, rheological characteristic is all suitable with existing pigment yellow 93, it is adaptable in the ink of the high grade of transparency;
(2) preparation method of disazo condensation compound provided by the invention is simple, easily-controlled reaction conditions, and cheaper starting materials is easy to get, and is suitable to large-scale industrial production;
(3) disazo condensation compound provided by the invention can mix with pigment yellow 93 by special ratios, obtains color compositions, significantly improves the transparency of pigment, and its green glow is higher, can as coloring agent in multiple system.
Accompanying drawing explanation
Fig. 1 illustrates the testing electronic microscope figure of solid U.S.A yellow 3GNP thoroughly;
Fig. 2 illustrates the testing electronic microscope figure of the disazo condensation compound that embodiment 1 prepares;
Fig. 3 illustrates the X ray diffracting spectrum of solid U.S.A yellow 3GNP thoroughly;
Fig. 4 illustrates the X ray diffracting spectrum of the disazo condensation compound that embodiment 1 prepares;
Fig. 5 illustrates the infrared spectrogram of pigment yellow 93 that comparative example prepares;
Fig. 6 illustrates the infrared spectrogram of the disazo condensation compound that embodiment 1 prepares.
Detailed description of the invention
Below by accompanying drawing, experimental example and embodiment, the present invention is described in more detail. Being illustrated by these, the features and advantages of the invention will become more apparent from clearly.
According to the first aspect of the invention, it is provided that a kind of disazo condensation compound, its structure is such as shown in formula I,
Wherein, X, Y are fat amido or aryl amine.
In a preferred embodiment in accordance with the present invention, containing aromatic hydrocarbons substituent group in described fatty amine based structures formula, it is preferable that containing C4��C20Aromatic hydrocarbons substituent group, more preferably contain C8��C16Aromatic hydrocarbons substituent group, and/or
Described aryl amine is substituted or unsubstituted anilino-, it is preferred to by one or more replaced anilino-of alkyl, alkoxyl or halogen atom, more preferably by the anilino-that methyl and/or chlorine atom are replaced.
Preferably, in formula I, X, Y are selected from group as shown in formula II or formula III, and are group shown in formula II during X, Y difference,
It is highly preferred that in formula I, X is group shown in formula II for such as group shown in formula III and Y, or, X is group shown in formula III for such as group shown in formula II and Y.
Most preferably, the compound that formula I is as follows:
The green glow of above-mentioned disazo condensation compound provided by the invention is higher, and the transparency significantly improves, and on its thermostability, solvent resistance, dispersibility, ink, rheological characteristic all with existing pigment yellow 93 quite, can be applicable in the ink of the high grade of transparency.
According to the second aspect of the invention, it is provided that a kind of method preparing disazo condensation compound described above, the such as compound shown in formula IV is carried out condensation reaction with fatty amine and arylamine, obtains described disazo condensation compound,
Wherein, containing aromatic hydrocarbons substituent group in described fatty amine structural formula, it is preferable that containing C4��C20Aromatic hydrocarbons substituent group, more preferably contain C8��C16Aromatic hydrocarbons substituent group, and/or
Described arylamine is substituted or unsubstituted aniline, it is preferred to by one or more replaced aniline of alkyl, alkoxyl or halogen atom, more preferably by the aniline that methyl and/or chlorine atom are replaced, for instance 3-methyl-2-chloroaniline, and/or
The mole of described fatty amine is the 1��50% of arylamine mole, it is preferable that 3��30%, more preferably 5��20%.
The method specifically includes following steps: be dissolved in solvent by the such as compound shown in formula IV, is added thereto to fatty amine and arylamine, and the lower insulation reaction of heating, reaction is lowered the temperature after terminating, filtered, and obtains described compound.
Wherein, described solvent is halogeno-benzene or alkylbenzene, it is preferred to dichloro-benzenes, trichloro-benzenes, dimethyl benzene or trimethylbenzene, and/or
Preferably it is initially charged fatty amine, adds arylamine, and/or
React 0.5��10 hour at 100��200 DEG C, react 1��6 hour at 120��180 DEG C, it is most preferred that react 2��4 hours at 140��160 DEG C.
In a preferred embodiment in accordance with the present invention, described method includes: the such as intermediate shown in formula IV is dissolved in dichloro-benzenes, sequentially drip the dichlorobenzene solution of fatty amine and arylamine wherein, dropwise post-heating to 140��160 DEG C, insulation reaction 2��4 hours, reaction is lowered the temperature after terminating, is filtered, dry after filter cake methanol and water washing, obtains described compound.
The present invention also provides for a kind of color compositions containing disazo condensation compound described above, and it contains at least one compound and pigment yellow 93 as shown in formula I, described pigment yellow 93 as shown in formula (V),
In formula I, X, Y are selected from group as shown in formula II or formula III, and are group shown in formula II during X, Y difference,
In a preferred embodiment in accordance with the present invention, in above-mentioned color compositions, the mole of compound as shown in formula I is the 1��50% of pigment yellow 93 mole, preferably 3��30%, more preferably 5��20%, wherein, pigment yellow 93 can additionally add, it is also possible to acquisition is synthesized together with compound shown in formula I.
Above-mentioned color compositions provided by the invention can as coloring agent in ink, coating and plastic, and its green glow is higher, and transparency significantly improves.
Embodiment
Embodiment 1
30g acyl chlorides compound (0.0144mol) is put in the 250ml four-hole boiling flask containing 100g dichloro-benzenes, oil bath is warming up to 130 DEG C, dropping 0.84g (0.00288mol) rosin amine, and the dichlorobenzene solution of 3.67g (0.02592mol) 3-chloro-2-methyl aniline, dropping 30min, is warming up to 150 DEG C and is incubated 3 hours after dropwising. Cooling is filtered, washing after methanol washing, and solvent recovery, filter cake is dried, and obtains described disazo condensation compound.
Its electron microscope observation result is as shown in Figure 2; Its X-ray diffraction result is as shown in Figure 4; Its infrared spectrogram is as shown in Figure 6; The table 1 that its elementary analysis result sees below.
Embodiment 2
30g acyl chlorides compound (0.0144mol) is put in the 250ml four-hole boiling flask containing 100g dichloro-benzenes, oil bath is warming up to 130 DEG C, dropping 1.25g (0.00432mol) rosin amine, and the dichlorobenzene solution of 3.46g (0.02448mol) 3-chloro-2-methyl aniline, dropping 30min, is warming up to 150 DEG C and is incubated 3 hours after dropwising. Cooling is filtered, washing after methanol washing, and solvent recovery, filter cake is dried, and obtains described disazo condensation compound.
Its electron microscope observation result, X-ray diffractogram are similar with embodiment 1 products obtained therefrom with infrared spectrogram, the table 1 that its elementary analysis result sees below.
Comparative example
30g acyl chlorides compound (0.0144mol) is put in the 250ml four-hole boiling flask containing 100g dichloro-benzenes, oil bath is warming up to 130 DEG C, the dichlorobenzene solution of dropping 4.08g (0.0288mol) 3-chloro-2-methyl aniline, dropping 30min, is warming up to 150 DEG C and is incubated 3 hours after dropwising. Cooling is filtered, washing after methanol washing, and solvent recovery, filter cake is dried, and obtains compound as shown in formula (V), is pigment yellow 93.
Its infrared spectrogram is as it is shown in figure 5, the table 1 that sees below of its elementary analysis result.
Experimental example
All verification test standards are the solid beautiful yellow 3GNP thoroughly of Ciba company.
Experimental example 1 electron-microscopic analysis
Adopting ultramicroscope, the disazo condensation compound respectively solid U.S.A yellow 3GNP thoroughly, embodiment 1 prepared is tested, and result is shown in Fig. 1��2.
As shown in Fig. 1��2, its particle crystallization state of the product that the present invention prepares clearly changes.
Experimental example 2X x ray diffraction analysis x
Adopting X-ray diffractometer, the disazo condensation compound respectively solid U.S.A yellow 3GNP thoroughly, embodiment 1 prepared is tested, and result is shown in Fig. 3��4.
Comparison diagram 3 and Fig. 4 are known, its crystal habit of product that the embodiment of the present invention 1 prepares is different from the solid beautiful yellow 3GNP thoroughly of standard substance, its be distinguished by X-ray diffraction Fig. 2 �� angle be 44.5 ��, 64.8 ��, 78.2 �� places have 3 relatively weak absorbing peak become multiple to weaken, simultaneously, 2 �� angles are that 7.1 �� of place's absworption peaks become 4.8 �� and 9.0 �� of two absworption peaks, as can be seen here, its microstructure of product that the present invention prepares clearly changes.
Experimental example 3 infrared spectrum detects
Employing infrared spectrometer, the disazo condensation compound that the pigment yellow 93 respectively comparative example prepared, embodiment 1 prepare carries out examination of infrared spectrum, and result is shown in Fig. 5��6.
By formula (V) structure it can be seen that only a small amount of methylene, methyl exist in the pigment yellow 93 for preparing of comparative example, its infrared spectrogram (Fig. 5) is at vas��2925cm-1With vs �� 2850cm-1Place is unconspicuous methylene stretching vibration absworption peak only;
And owing to introducing rosin amine in embodiment 1 so that having multiple methylene to exist in product, its infrared spectrogram (Fig. 6) is at vas��2925cm-1And vs��2850cm-1There is obvious methylene stretching vibration absworption peak at place, illustrates that embodiment 1 has prepared theoretical product, and preparation method provided by the invention is stable, reliable.
Experimental example 4 elementary analysis
The product that embodiment 1��2, comparative example are prepared carries out elementary analysis, and result is in Table 1.
Table 1. elementary analysis result
| C | H | CI | N | O | Molecular formula | |
| Comparative example | 42.71 | 34.85 | 5.07 | 7.86 | 6 | C43H35N8O6Cl5 |
| Embodiment 1 | 44.32 | 37.15 | 4.96 | 8.09 | 6 | C44.3H37.3N8.1O6Cl4.9 |
| Embodiment 2 | 44.85 | 38.56 | 4.79 | 8.21 | 6 | C44.95H38.45N8.15O6Cl4.85 |
As shown in table 1, being computed, in the product that embodiment 1��2 prepares, C, H element content increase, and Cl constituent content reduces, and meets the molecular composition of modified structure.
Experimental example 5 ink system compares coloured light, tinctorial strength and transparency
Coloured light comparative approach: pigment sample 0.200g embodiment 1��2 prepared is dispersed to 0.600 oleum lini, 5 the totally 250 circle dispersions of plain grinding instrument, ink dispersion scraper plate identical with the pigment yellow 93 that comparative example prepares compares pigment difference.
Tinctorial strength comparative approach: the pigment sample 0.050g that embodiment 1��2 is prepared, and 1.000g titanium dioxide (R902) is dispersed to 1.000g oleum lini, 5 the totally 250 circle dispersions of plain grinding instrument, ink dispersion scraper plate identical with the pigment yellow 93 that comparative example prepares compares pigment difference.
Transparency comparative approach: to be printed on the paper of black ribbon line as a setting, the method that naked eyes judge compares.
Coloured light, tinctorial strength and transparency comparative result in table 2. ink system
| Gu beautiful yellow 3GNP thoroughly | Comparative example | Embodiment 1 | Embodiment 2 | |
| Form and aspect | Standard | Slightly red | Slightly green | Greener |
| Covering power | Standard | Micro-high | More saturating | More saturating |
| Intensity | Standard | 100 | 97 | 95 |
As shown in Table 2, the product that the embodiment of the present invention 1��2 prepares compares with standard substance, and its coloured light is substantially partially green, and transparency is greatly improved, and the pigment yellow 93 that comparative example prepares compares then substantially slightly red with standard substance, hides higher, and transparency is relatively low.
Experimental example 6 ink fluidity compares
By the dispersion ink 0.100g of the coloured light containing pigment sample carrying out in experimental example 5 preparing when coloured light the compares Circular glass sheet center being placed in metal fixed disk, upper Circular glass sheet is placed on the Circular glass sheet in metal fixed disk, centre is made to have ink to partly overlap, press 200g counterweight (noticing that metal fixed disk keeps level) immediately, start timing;
Removing counterweight after 15min, measure maximum and the minima of ink cylinder diameter with transparent gage, if the difference of maximum and minima is be more than or equal to 2mm, then experiment re-starts.
The arithmetic mean of instantaneous value of measurement result is the numerical value of fluidity, and result is in Table 3.
Table 3. ink fluidity measurement result
| Gu beautiful yellow 3GNP thoroughly | Comparative example | Embodiment 1 | Embodiment 2 | |
| Fluidity/mm | 23.2 | 18.9 | 21.0 | 22.8 |
As shown in table 3, its ink fluidity of product that embodiment 1��2 prepares has clear improvement.
Experimental example 7 plastics (LDPE) system compares coloured light, tinctorial strength and covering power
True qualities: weigh pigment sample that embodiment 1��2 prepares and each 0.1500g of pigment yellow 93 that comparative example prepares, after LDPE resin is placed on two roller machines (120 DEG C), open motor, preplasticizing about 1 minute is (when two roller machines roll, resin should stick on preliminary roller, must again refund between two rollers from the material dropped between two rollers), after resin plastifies completely, the above-mentioned pigment sample weighed up slowly is homogeneously added in the plastics plastified, two roller machines carry out mixing, after resin and pigment are thoroughly mixed, start timing, and carry out upset 6 minutes with bamboo chip scraper is continual, close motor, adjusting roller spacing is 5mm, open motor, continue mixing 0.5 minute (color chips should stick on preliminary roller) membrane afterwards, comparing embodiment and comparative example gained tabletting.
Reduced shade: weigh pigment sample that embodiment 1��2 prepares and each 0.0250g of pigment yellow 93 that comparative example prepares, 0.2500g titanium dioxide, LDPE resin is placed on two roller machines after hot 20 seconds, open motor, preplasticizing about 1 minute is (when two roller machines roll, resin should stick on preliminary roller, must again refund between two rollers from the material dropped between two rollers), after resin plastifies completely, load weighted pigment and titanium dioxide are slowly homogeneously added in the plastics plastified, two roller machines carry out mixing, after resin and pigment are thoroughly mixed, start timing, and carry out upset 6 minutes with bamboo chip scraper is continual, close motor, adjusting roller spacing is 5mm, open motor, continue mixing 0.5 minute (color chips should stick on preliminary roller) membrane afterwards, the solid beautiful independent tabletting according to the method described above of yellow 3GNP thoroughly of standard substance.
For reference, the tinctorial strength of sample is evaluated by Computer color testing instrument with the solid beautiful yellow 3GNP thoroughly of standard substance.
Coloured light and covering power comparative result in table 4. plastics (LDPE) system
| Title | Gu beautiful yellow 3GNP thoroughly | Comparative example | Embodiment 1 | Embodiment 2 |
| Form and aspect | Standard | 2 grades red | 2 grades green | 3 grades green |
| Covering power | Standard | 1 grade high | 2 grades thoroughly | 3 grades thoroughly |
Tinctorial strength comparative result in table 5. plastics (LDPE) system
| Gu beautiful yellow 3GNP thoroughly | Comparative example | Embodiment 1 | Embodiment 2 | |
| Relative intensity | 100.000 | 98.962 | 95.719 | 94.698 |
Thermostability test result in table 6. plastics (LDPE) system
The above results shows, it is partially green that the modified pigment prepared by embodiment 1��2 applies coloured light in plastics system, but does not have ink system medium green obvious mutually, and covering power is partially saturating, and also without obvious in ink system, intensity slightly declines.
The experimental example 8 application in NC ink
In vial, it is sequentially added into 28.8g celluloid lacquer, 32.0g dehydrated alcohol, 120g bead, 19.2g pigment, vibrates 50 minutes with vibration case after sealing, shake after well and take off standing 15 minutes, obtain dispersion.
True qualities: take the above-mentioned dispersion of 12.0g in plastic cup, add 18.0gLetdownVarnish glue head to stir evenly, pigment sample embodiment 1��2, comparative example prepared with disposable dropper is a little with standard sample dropping on PP film, scrape uniformly film with silk rod (12 ��m), be drying and forming-film (evaluating the transparency) after placing 10 minutes.
The pigment sample prepared by disposable dropper just embodiment 1��2, comparative example is a little with standard sample dropping in being with on black thick stick art paper, put 75 ��m of wet film preparing devices, scrape coating agent which has to be dissolved in alcohol before use with automatic spray device, be drying and forming-film (evaluating coloured light and glossiness) after placing 10 minutes.
Reduced shade: take the above-mentioned dispersion of 1.50g in plastic cup, add 13.5g chalk, stir evenly with glue head, the pigment sample prepared by disposable dropper just embodiment 1��2, comparative example is a little with standard sample dropping in being with on black thick stick art paper, put 75 ��m of wet film preparing devices, scrape coating agent which has to be dissolved in alcohol before use with automatic spray device, be drying and forming-film after placing 10 minutes, use colour photometer colour examining.
Coloured light and covering power test result in table 7.NC ink system
| Title | Gu beautiful yellow 3GNP thoroughly | Comparative example | Embodiment 1 | Embodiment 2 |
| Form and aspect | Standard | 2 grades red | 3 grades green | 4 grades green |
| Covering power | Standard | 2 grades high | 5 grades thoroughly | 6 grades thoroughly |
Tinctorial strength test result in table 8.NC ink system
| Title | Gu beautiful yellow 3GNP thoroughly | Comparative example | Embodiment 1 | Embodiment 2 |
| Relative intensity | 100.000 | 99.321 | 98.568 | 95.486 |
The above results shows, under N/C system, the pigment sample coloured light that embodiment 1��2 prepares is substantially partially green, and micro-Huang, covering power significantly becomes, and intensity slightly declines.
Above in association with preferred implementation and exemplary example, the present invention is described in detail. But it is to be understood that, these detailed description of the invention are only the illustrative explanations to the present invention, not to protection scope of the present invention constitute any restriction. When without departing from spirit and scope of the present invention, it is possible to the technology of the present invention content and embodiment thereof are carried out various improvement, equivalencing or modification, and these each fall within protection scope of the present invention. Protection scope of the present invention is as the criterion with claims.
Claims (10)
1. the structure such as disazo condensation compound shown in formula I,
Wherein, X, Y are fat amido or aryl amine,
Containing aromatic hydrocarbons substituent group in described fatty amine based structures formula, it is preferable that containing C4��C20Aromatic hydrocarbons substituent group, and/or
Described aryl amine is substituted or unsubstituted anilino-, it is preferred to by one or more replaced anilino-of alkyl, alkoxyl or halogen atom.
2. compound according to claim 1, it is characterised in that
Containing C in described fatty amine based structures formula8��C16Aromatic hydrocarbons substituent group, and/or
Described aryl amine is by the replaced anilino-of methyl and/or chlorine atom.
3. compound according to claim 1 and 2, it is characterised in that
In formula I, X, Y are selected from group as shown in formula II or formula III, and are group shown in formula II during X, Y difference,
4. according to the compound one of claims 1 to 3 Suo Shu, it is characterised in that
In formula I, X is group shown in formula II for such as group shown in formula III and Y, or, X is group shown in formula III for such as group shown in formula II and Y,
Preferably, the compound that formula I is as follows:
5. prepare the method for compound as described in one of Claims 1-4 for one kind, it is characterised in that the compound as shown in formula IV carries out condensation reaction with fatty amine and arylamine, obtains described disazo condensation compound,
Containing aromatic hydrocarbons substituent group in described fatty amine structural formula, it is preferable that containing C4��C20Aromatic hydrocarbons substituent group, and/or
Described arylamine is substituted or unsubstituted aniline, it is preferred to by one or more replaced aniline of alkyl, alkoxyl or halogen atom.
6. method according to claim 5, it is characterised in that
Containing C in described fatty amine structural formula8��C16Aromatic hydrocarbons substituent group, and/or
Described arylamine is by the replaced aniline of methyl and/or chlorine atom.
7. the method according to claim 5 or 6, it is characterised in that
The mole of described fatty amine is the 1��50% of arylamine mole, it is preferable that 3��30%, more preferably 5��20%.
8. according to the method one of claim 5 to 7 Suo Shu, it is characterised in that the method comprises the following steps:
Step 1, the such as compound shown in formula IV is dissolved in solvent,
Step 2, it is added thereto to fatty amine and arylamine, the lower insulation reaction of heating,
Step 3, reaction are lowered the temperature after terminating, are filtered, and obtain described compound.
9. method according to claim 8, it is characterised in that
In step 1, described solvent is halogeno-benzene or alkylbenzene, it is preferred to dichloro-benzenes, trichloro-benzenes, dimethyl benzene or trimethylbenzene, and/or
Preferably it is initially charged fatty amine, adds arylamine.
10. according to the method one of claim 5 to 9 Suo Shu, it is characterised in that
In step 2, react 0.5��10 hour at 100��200 DEG C, it is preferable that react 1��6 hour at 120��180 DEG C, react 2��4 hours at 140��160 DEG C.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3413279A (en) * | 1965-01-25 | 1968-11-26 | Ciba Ltd | Disazo pigments |
| US5194088A (en) * | 1991-07-08 | 1993-03-16 | Ciba-Geigy Corporation | Process for conditioning organic pigments |
| CN102558906A (en) * | 2011-12-22 | 2012-07-11 | 鞍山七彩化学股份有限公司 | Yellow disazo mixed pigment with high tinting strength |
-
2016
- 2016-03-08 CN CN201610131583.0A patent/CN105646278B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3413279A (en) * | 1965-01-25 | 1968-11-26 | Ciba Ltd | Disazo pigments |
| US5194088A (en) * | 1991-07-08 | 1993-03-16 | Ciba-Geigy Corporation | Process for conditioning organic pigments |
| CN102558906A (en) * | 2011-12-22 | 2012-07-11 | 鞍山七彩化学股份有限公司 | Yellow disazo mixed pigment with high tinting strength |
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