CN105602285A - Pigment composition containing octadecylamino bisazo condensation compound and preparation method of pigment composition - Google Patents
Pigment composition containing octadecylamino bisazo condensation compound and preparation method of pigment composition Download PDFInfo
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- CN105602285A CN105602285A CN201610128207.6A CN201610128207A CN105602285A CN 105602285 A CN105602285 A CN 105602285A CN 201610128207 A CN201610128207 A CN 201610128207A CN 105602285 A CN105602285 A CN 105602285A
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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
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0055—Mixtures of two or more disazo dyes
-
- 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
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
- C09B43/124—Preparation of azo dyes from other azo compounds by acylation of amino groups with monocarboxylic acids, carbamic esters or halides, mono- isocyanates, or haloformic acid esters
- C09B43/132—Preparation of azo dyes from other azo compounds by acylation of amino groups with monocarboxylic acids, carbamic esters or halides, mono- isocyanates, or haloformic acid esters having the carboxylic group directly attached to an aromatic carbocyclic ring
-
- 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
- C09B67/0079—Azoic dyestuff preparations
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
- C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
Abstract
The invention discloses a pigment composition containing an octadecylamino bisazo condensation compound with a following structure (please see the structure in the description) and a preparation method of the pigment composition, wherein X and Y are selected from fatty amine groups or arylamine groups. The yellow pigment composition is obtained by mixing the bisazo condensation compound with the specific structure into pigment yellow 93, green light is higher, the transparency is significantly improved, the heat resistance, the solvent resistance, the dispersity and the rheological property on ink are equivalent to those of existing pigment yellow 93, and the composition is suitable for being used in high-transparency printing ink.
Description
Technical field
The invention belongs to chemical dye field, be specifically related to a kind of pigment that contains octadecylamine base disazo condensation compoundComposition and method of making the same.
Background technology
Biacetyl antifebrin azo condensation pigment passes through amido link on biacetyl acetophenone amine pigment molecule basisConnect again a replacement aromatic ring at molecule two ends. This type of pigment, its molecular weight is large, and tinting strength, tinting power and fastness ability are stronger, especially introduceMore amide group, makes compound more easily form in molecule and intermolecular hydrogen bonding, and such molecular structure has improved face greatlyEvery fastness ability, particularly heat resistance and the solvent resistance of material. In coloring plastic, resistance to migration improves a lot. ButBecause production cost is higher, therefore price is high, is mainly used in high-grade occasion. Wherein pigment yellow 93 shows a kind of bright green light HuangLook due to its remarkable heat resistance, light resistance and good resistance to migration, has better in high-grade printing-ink, sedan car top coatApplication, in plastic pvc, PP and LDPE, be also widely used.
Patent US3413279 discloses a kind of preparation method of yellow 93, and the method is by diazo component 3-amino-4 chlorobenzene firstDiazol and the coupling in o-dichlorohenzene at 105-110 DEG C of the chloro-5-methyl of coupling component 2-biacetyl acetyl-p-phenylenediamine of acidMake bisazo dicarboxylic acids intermediate, because the method is heterogeneous reaction, cause reaction to be difficult to carry out completely, productive rate is lower.
The pigmentation method of pigment yellow 93 is disclosed in patent US5194088. In the method by crude pigment product, anhydrous slufuric acidSodium and steel ball are placed in ball grinder, ball milling 48h under room temperature. Treat that ball milling is complete, under room temperature by ball milling crude product in dimethyl sulfoxide (DMSO)Process 2h, through hot water making beating washing, dryly can obtain pigment yellow 93 products.
According to market survey, although yellow 93 have high-fire resistance, good resistance to migration, the transparency of pigment yellow 93 need to changeKind property, current Huang 93 adopts disclosed preparation method and pigmentation method in foregoing invention, and the product transparency obtaining is not stillSatisfactory, for disazo condensation class pigment, it,, by the particle adjustment of self, is difficult to breakthrough entering in the transparencyExhibition. The present invention introduces the synthesis mode of mixed crystal, and to obtain high transparent, heat resistance has the good derivative significantly improving simultaneously.
Summary of the invention
In order to overcome the problems referred to above, the inventor has carried out research with keen determination to disazo pigment and preparation method thereof, obtainsThe disazo condensation compound that green glow is stronger, the transparency significantly improves, and itself and pigment yellow 93 are mixed to get a kind of yellowLook color compositions, on its heat resistance, solvent resistance, dispersiveness, ink, rheological characteristic is all suitable with existing pigment yellow 93, is suitable forIn the seal China ink of the high grade of transparency.
The object of the present invention is to provide following aspect:
(1) a yellow uitramarine composition, it contains at least one suc as formula compound shown in (I) and pigment yellow 93,
In formula (I) compound, X, Y are fatty amido or aryl amine,
Preferred described fatty amido is straight chain saturated fat amido, is preferably C6～C22Straight chain alkylamino radical, more preferablyC12～C18Straight chain alkylamino radical, and/or
Preferred described aryl amine, for replacing or unsubstituted anilino-, is preferably by one of alkyl, alkoxyl or halogen atomOr multiple replaced anilino-s, the anilino-more preferably being replaced by methyl and/or chlorine atom;
(2) composition as described in above-mentioned (1), is characterized in that,
In formula (I) compound, X, Y are selected from suc as formula group shown in (II) or formula (III),
(3) composition as described in above-mentioned (1) or (2), is characterized in that,
In formula (I) compound, X, Y can be identical or different, and preferably X is for being formula (II) institute suc as formula group shown in (III) and YShow group, or X is for being group shown in formula (III) suc as formula group shown in (II) and Y, more preferably formula (I) is change as followsCompound:
(4) if above-mentioned (1) is to the composition as described in one of (3), it is characterized in that,
Pigment yellow 93 can additionally add, and also can react to synthesize with compound one shown in formula (I) obtains;
(5) one is prepared if above-mentioned (1) is to the method for composition as described in one of (4), it is characterized in that, will be suc as formula (IV) instituteThe compound showing and fatty amine and arylamine carry out condensation reaction, obtain compound shown in formula (I),
The optional pigment yellow 93 that adds;
(6) method as described in above-mentioned (5), is characterized in that, the method comprises the following steps:
To be dissolved in solvent suc as formula the compound shown in (IV),
Add wherein fatty amine and arylamine, the lower insulation reaction of heating,
Reaction finishes rear cooling, filtration, obtains compound shown in formula (I);
(7) method as described in above-mentioned (5) or (6), is characterized in that,
0.5～10h is carried out in described condensation reaction at 100～200 DEG C, preferably at 120～180 DEG C, carries out 1～6h, morePreferably at 140～160 DEG C, carry out 2～4h;
(8) if above-mentioned (5) are to the method as described in one of (7), it is characterized in that,
Described fatty amine is straight chain saturated fat amine, is preferably C6～C22Straight chain alkanamine, more preferably C12～C18StraightChain alkanamine, for example, be octadecylamine, and/or
Described arylamine, for replacing or unsubstituted aniline, is preferably by one or more institute of alkyl, alkoxyl or halogen atomThe aniline replacing, the aniline more preferably being replaced by methyl and/or chlorine atom, for example 3-methyl-2-chloroaniline, and/or
The mole of described fatty amine is 2～60% of arylamine mole, preferably 4～40%, more preferably 5～20%;
(9) if above-mentioned (6) are to the method as described in one of (8), it is characterized in that,
Described solvent is halogeno-benzene or alkylbenzene, is preferably dichloro-benzenes, trichloro-benzenes, dimethyl benzene or trimethylbenzene, and/or
Preferably first add fatty amine, then add arylamine;
(10) purposes of the composition that method makes as described in above-mentioned (1) to one of (4) or (5) to one of (9), as HuangLook pigment uses.
The beneficial effect that the present invention has comprises:
(1) the present invention adds specific fatty amine in the amidated process of pigment yellow 93 condensation, and mixed crystal is synthetic a kind of twoAzo condensation compound, its green glow is stronger, and the transparency significantly improves, rheological characteristic on heat resistance, solvent resistance, dispersiveness, inkAll suitable with existing pigment yellow 93, be applicable in the seal China ink of the high grade of transparency;
(2) preparation method of disazo condensation compound provided by the invention is simple, easily-controlled reaction conditions, raw material cheapnessBe easy to get, be suitable for large-scale industrial production;
(3) color compositions provided by the invention mixes the above-mentioned disazo condensation chemical combination of special ratios in pigment yellow 93Thing, significantly improved the transparency of pigment, and its green glow is stronger, can be used as colouring agent for multiple system.
Brief description of the drawings
Fig. 1 illustrates the testing electronic microscope figure of the solid saturating yellow 3GNP of U.S.;
Fig. 2 illustrates the testing electronic microscope figure of the disazo condensation compound that embodiment 1 makes;
Fig. 3 illustrates the X ray diffracting spectrum of the solid saturating yellow 3GNP of U.S.;
Fig. 4 illustrates the X ray diffracting spectrum of the disazo condensation compound that embodiment 1 makes;
Fig. 5 illustrates the infrared spectrogram of the pigment yellow 93 that comparative example makes;
Fig. 6 illustrates the infrared spectrogram of the disazo condensation compound that embodiment 1 makes.
Detailed description of the invention
Below by accompanying drawing, experimental example and embodiment, the present invention is described in more detail. By these explanations, the present inventionFeature and advantage will become more explicit.
According to a first aspect of the invention, provide a kind of yellow uitramarine composition, it contains at least one suc as formula shown in (I)Compound and pigment yellow 93,
In formula (I) compound, X, Y are fatty amido or aryl amine.
According in the preferred embodiment of the present invention, described fatty amido is straight chain saturated fat amido, is preferably C6～C22Straight chain alkylamino radical, more preferably C12～C18Straight chain alkylamino radical, and/or
Described aryl amine, for replacing or unsubstituted anilino-, is preferably by one of alkyl, alkoxyl or halogen atom or manyIndividual replaced anilino-, the anilino-more preferably being replaced by methyl and/or chlorine atom.
Preferably, in formula (I) compound, X, Y are selected from suc as formula group shown in (II) or formula (III),
In formula (I) compound, X, Y can be identical or different, and preferably X is for being formula (II) institute suc as formula group shown in (III) and YShow group, or X is for being group shown in formula (III) suc as formula group shown in (II) and Y, more preferably formula (I) is change as followsCompound:
According in the preferred embodiment of the present invention, in described color compositions, suc as formula rubbing of compound shown in (I)Your amount is pigment yellow 93 moles 1～50%, preferably 3～30%, more preferably 5～20%.
Wherein, pigment yellow 93 can additionally add, and also can react to synthesize with compound one shown in formula (I) obtains.
The green glow of above-mentioned disazo condensation compound provided by the invention is stronger, and the transparency significantly improves, its heat resistance, resistance toOn solvent borne, dispersiveness, ink, rheological characteristic is all suitable with existing pigment yellow 93, and it is mixed with pigment yellow 93 with special ratiosThe yellow uitramarine composition obtaining, its transparency significantly improves, and can be used as colouring agent for multiple system, for example, be applied to heightIn the seal China ink of transparency.
According to a second aspect of the invention, provide a kind of method of preparing color compositions described above, will be suc as formula (IV)Shown compound and fatty amine and arylamine carry out condensation reaction, obtain compound shown in formula (I), optionally add pigment yellow 93,
Wherein, described fatty amine is straight chain saturated fat amine, is preferably C6～C22Straight chain alkanamine, more preferably C12～C18Straight chain alkanamine, be for example octadecylamine, and/or
Described arylamine, for replacing or unsubstituted aniline, is preferably by one or more institute of alkyl, alkoxyl or halogen atomThe aniline replacing, the aniline more preferably being replaced by methyl and/or chlorine atom, for example 3-methyl-2-chloroaniline, and/or
The mole of described fatty amine is 2～60% of arylamine mole, preferably 4～40%, more preferably 5～20%.
The method specifically comprises the following steps: by being dissolved in solvent suc as formula the compound shown in (IV), add wherein fatFat amine and arylamine, the lower insulation reaction of heating, reaction finishes rear cooling, filtration, obtains compound shown in formula (I).
Wherein, described solvent is halogeno-benzene or alkylbenzene, is preferably dichloro-benzenes, trichloro-benzenes, dimethyl benzene or trimethylbenzene,And/or
Preferably first add fatty amine, then add arylamine, and/or
Described condensation reaction is carried out 0.5～10 hour at 100～200 DEG C, preferably at 120～180 DEG C, carries out 1～6Hour, more preferably at 140～160 DEG C, carry out 2～4 hours.
According in the preferred embodiment of the present invention, described method comprises: will be dissolved in suc as formula the compound shown in (IV)Dichloro-benzenes, drips the dichlorobenzene solution of fatty amine and arylamine in turn wherein, is heated to 140～160 DEG C after dropwising, insulationReact 2～4 hours, reaction finishes rear cooling, filtration, and filter cake, with dry after methyl alcohol and water washing, obtains chemical combination shown in formula (I)Thing.
Pigment yellow 93 can additionally add, and also can react to synthesize with compound one shown in formula (I) obtains. Extra interpolationWhen pigment yellow, the mole that makes pigment yellow 93 is for suc as formula 1～50% of compound mole shown in (I), and preferably 3～30%,More preferably 5～20%.
According to a third aspect of the invention we, provide the purposes of color compositions described above, it uses as yellow uitramarine.
Preferably above-mentioned color compositions provided by the invention is used for ink, coating and plastic products as colouring agent, itsGreen glow is stronger, and transparency significantly improves.
Embodiment
Embodiment 1
30g acyl chlorides compound (0.0144mol) is dropped into containing in the 250ml four-hole boiling flask of 100g dichloro-benzenes, and oil bath is warming up to130 DEG C, drip 0.77g (0.00288mol) octadecylamine, and 3.67g (0.02592mol) 3-chloro-2-methyl aniline twoChlorobenzene solution, drips 30min, is warming up to 150 DEG C of insulations 3 hours after dropwising. Cooling is filtered, and methanol wash after washing is moltenAgent is reclaimed, and filter cake is dried, and obtains described disazo condensation compound.
Its electron microscope observation result as shown in Figure 2.
Its X-ray diffraction result as shown in Figure 4.
Adopt infrared spectrometer to carry out examination of infrared spectrum, result as shown in Figure 6. As seen from Figure 6, owing to introducing octadecaneAmine, making has multiple methylene to exist in product, and its infrared spectrogram is at vas≈2925cm-1And vs≈2850cm-1Place has obviouslyMethylene stretching vibration absworption peak, illustrate that embodiment 1 has made theoretical product, preparation method provided by the invention is stable, canLean on.
Its results of elemental analyses is: C, 44.11; H, 37.89; Cl, 4.88; N, 8.22; O, 6. Definite molecular formula thusFor C44.1H38.1N8.1O6Cl4.9. As calculated, in the product that embodiment 1 makes, C, H constituent content increase, and Cl constituent content reduces,Meet the molecular composition of structure after modification.
Embodiment 2
30g acyl chlorides compound (0.0144mol) is dropped into containing in the 250ml four-hole boiling flask of 100g dichloro-benzenes, and oil bath is warming up to130 DEG C, drip 1.16g (0.00432mol) octadecylamine, and 3.46g (0.02448mol) 3-chloro-2-methyl aniline twoChlorobenzene solution, drips 30min, is warming up to 150 DEG C of insulations 3 hours after dropwising. Cooling is filtered, and methanol wash after washing is moltenAgent is reclaimed, and filter cake is dried, and obtains described disazo condensation compound.
Its electron microscope observation result, X-ray diffractogram and infrared spectrogram and embodiment 1 products obtained therefrom are similar;
Its results of elemental analyses is: C, 44.56; H, 38.99; Cl, 4.80; N, 8.07; O, 6. Definite molecular formula thusFor C44.65H39.65N8.15O6Cl4.85. As calculated, in the product that embodiment 2 makes, C, H constituent content increase, and Cl constituent content subtractsFew, also meet the molecular composition of structure after modification.
Comparative example
30g acyl chlorides compound (0.0144mol) is dropped into containing in the 250ml four-hole boiling flask of 100g dichloro-benzenes, and oil bath is warming up to130 DEG C, the dichlorobenzene solution of dropping 4.08g (0.0288mol) 3-chloro-2-methyl aniline, drips 30min, dropwises rear literTemperature was to 150 DEG C of insulations 3 hours. Cooling is filtered, methanol wash after washing, and solvent recovery, filter cake is dried, and obtains suc as formula shown in (V)Compound, is pigment yellow 93.
From formula (V) structure, in the pigment yellow 93 that comparative example 1 makes, only have a small amount of methylene, methyl to exist, it is redExternal spectrum result as shown in Figure 5, at vas≈2925cm-1And vs≈2850cm-1Place only has unconspicuous methylene stretching vibration to inhaleReceive peak.
Its results of elemental analyses is: C, 42.71; H, 34.85; Cl, 5.07; N, 7.86; O, 6. Definite molecular formula thusFor C43H35N8O6Cl5。
Experimental example
All verification test standards are the solid U.S. saturating yellow 3GNP of Ciba company.
Experimental example 1 electron-microscopic analysis
Adopt electron microscope, the disazo condensation the compound respectively saturating yellow 3GNP of solid U.S., embodiment 1 being made is surveyedExamination, the results are shown in Figure 1～2.
As shown in Fig. 1～2, its particle crystallization state of the product that the present invention makes clearly changes.
Experimental example 2X x ray diffraction analysis x
Adopt X-ray diffractometer, the disazo condensation the compound respectively saturating yellow 3GNP of solid U.S., embodiment 1 being made carries outTest, the results are shown in Figure 3～4.
Comparison diagram 3 and Fig. 4 are known, and it is solid thoroughly beautiful that its crystal habit of the product that the embodiment of the present invention 1 makes is different from standard itemsYellow 3GNP, its distinguishing characteristics is that X-ray diffraction Fig. 2 θ angle is 44.5 °, 64.8 °, 78.2 ° and has located 3 weak absworption peaks at doubleNumber weakens, and as can be seen here, its microstructure of the product that the present invention makes clearly changes.
In experimental example 3 ink systems, compare coloured light, tinctorial strength and transparency
Coloured light comparative approach: the pigment sample 0.200g that embodiment 1～2 is made is dispersed to 0.600 linseed oil,5 totally 250 circle dispersions of plain grinding instrument, the relatively pigment difference of the identical distributes ink scraper plate of pigment yellow 93 making with comparative example.
Tinctorial strength comparative approach: the pigment sample 0.050g that embodiment 1～2 is made, and 1.000g titanium dioxide(R902) dispersed to 1.000g linseed oil, plain grinding instrument 5 times totally 250 circles disperses, pigment yellow 93 phases that make with comparative exampleWith relatively pigment difference of distributes ink scraper plate.
Transparency comparative approach: with the paper that is printed on black strip line as a setting, the method for naked eyes judgement compares.
Coloured light, tinctorial strength and transparency comparative result in table 1. ink system
| Gu U.S. saturating yellow 3GNP | 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 | 104 | 106 |
As shown in Table 1, the product that the embodiment of the present invention 1～2 makes and standard items comparison, its coloured light is obviously partially green, transparentDegree significantly improves, and pigment yellow that comparative example makes 93 is redder with standard items, hides highlyer, and transparency is lower.
Experimental example 4 ink flow degree comparisons
The coloured light that contains pigment sample of preparing when carrying out coloured light comparison in experimental example 3 disperses black 0.100g to be placed in metalCircular glass sheet center in fixed disk, is placed on upper Circular glass sheet on the Circular glass sheet in metal fixed disk, has black portion in the middle of makingPoint overlapping, press immediately 200g counterweight (noticing that metal fixed disk keeps level), start timing;
After 15min, remove counterweight, measure maximum and the minimum of a value of ink cylinder diameter with transparent gage, if maximumThe difference of value and minimum of a value is more than or equal to 2mm, and experiment re-starts.
The arithmetic mean of instantaneous value of measurement result is the numerical value of fluidity, the results are shown in Table 2.
Table 2. ink flow degree measurement result
| Gu U.S. saturating yellow 3GNP | Comparative example | Embodiment 1 | Embodiment 2 | |
| Fluidity/mm | 23.2 | 18.9 | 20.5 | 21.5 |
As shown in table 2, its ink flow degree of the product that embodiment 1～2 makes has clear improvement.
Experimental example 5 plastics (LDPE) system is coloured light, tinctorial strength and covering power relatively
True qualities: the each 0.1500g of pigment yellow 93 that the pigment sample that weighing embodiment 1～2 makes and comparative example make, LDPEResin is placed on after two roller machines (120 DEG C), opens motor, and preplasticizing approximately 1 minute is (in the time that two roller machines roll, before resin should stick toOn roller, must again refund between two rollers from the material dropping between two rollers), after resin plastifies completely, by the above-mentioned face weighing upMaterial sample slowly add equably in the plastics that plastified, on two roller machines, carry out mixing, after resin mixes completely with pigment,Start timing, and overturn 6 minutes with bamboo chip scraper is continual, close motor, adjusting roller spacing is 5mm, opens motor, continuesMembrane, comparing embodiment and comparative example gained compressing tablet after continuous mixing 0.5 minute (color chips should stick on preliminary roller).
Reduced shade: weigh the each 0.0250g of pigment yellow 93 that the pigment sample that makes of embodiment 1～2 and comparative example make,0.2500g titanium dioxide, LDPE resin is placed on heat on two roller machines and, after 20 seconds, opens motor, and preplasticizing (is rolled at two roller machines for approximately 1 minuteWhen moving, resin should stick on preliminary roller, must again refund between two rollers from the material dropping between two rollers), treat that resin moulds completelyAfter change, load weighted pigment and titanium dioxide are slowly added in the plastics that plastified equably, on two roller machines, carry out mixingly, treatAfter resin mixes completely with pigment, start timing, and overturn 6 minutes with bamboo chip scraper is continual, close motor, adjust rollerSpacing is 5mm, opens motor, continues mixing 0.5 minute (color chips should stick on preliminary roller) rear membrane; Standard items are solid beautiful thoroughly yellow3GNP is independent compressing tablet according to the method described above.
Taking the solid U.S. saturating yellow 3GNP of standard items as reference, evaluate the tinctorial strength of sample by Computer color testing instrument.
Coloured light and covering power comparative result in table 3. plastics (LDPE) system
| Title | Gu U.S. saturating yellow 3GNP | 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 4. plastics (LDPE) system
| Gu U.S. saturating yellow 3GNP | Comparative example | Embodiment 1 | Embodiment 2 | |
| Relative intensity | 100.000 | 98.962 | 97.926 | 95.368 |
Heat resistance test result in table 5. plastics (LDPE) system
The above results demonstration, it is partially green that the prepared modified pigment of embodiment 1～2 is applied coloured light in plastics system, but do not haveHave ink system medium green mutually obvious, covering power is partially saturating, does not also have in ink system obviously, and intensity declines slightly.
The application of experimental example 6 in NC China ink
In vial, add successively 28.8g celluloid lacquer, 32.0g absolute ethyl alcohol, 120g bead, 19.2g faceMaterial, with vibration case vibration 50 minutes, shakes and takes off and leave standstill 15 minutes after good after sealing, obtains dispersion.
True qualities: get 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 being made with disposable dropper and standard sample drip a little on PP film, with silk(12 μ m) spread to uniform film to rod, and placing after 10 minutes is drying and forming-film (evaluating the transparency).
Drip a little in band by the disposable dropper pigment sample that just embodiment 1～2, comparative example make and standard sampleOn black thick stick art paper, put 75 μ m wet film preparing devices, scrape coating agent which has to be dissolved in alcohol before use with automatic spray device, placing after 10 minutes is drying and forming-film(evaluating coloured light and glossiness).
Reduced shade: get the above-mentioned dispersion of 1.50g in plastic cup, add 13.5g chalk, stir evenly with glue head, with disposableThe dropper pigment sample that just embodiment 1～2, comparative example make and standard sample drip a little in being with on black thick stick art paper, putUpper 75 μ m wet film preparing devices, scrape coating agent which has to be dissolved in alcohol before use with automatic spray device, and placing after 10 minutes is drying and forming-film, uses colour photometer colour examining.
Coloured light and covering power test result in table 6.NC China ink system
| Title | Gu U.S. saturating yellow 3GNP | Comparative example | Embodiment 1 | Embodiment 2 |
| Form and aspect | Standard | 2 grades red | 2 grades green | 2 grades green |
| Covering power | Standard | 2 grades high | 3 grades thoroughly | 4 grades thoroughly |
Tinctorial strength test result in table 7.NC China ink system
| Title | Gu U.S. saturating yellow 3GNP | Comparative example | Embodiment 1 | Embodiment 2 |
| Relative intensity | 100.000 | 99.321 | 97.021 | 98.706 |
The above results shows, under N/C system, the pigment sample coloured light that embodiment 1～2 makes is obviously partially green, and micro-Huang hidesLid power significantly becomes thoroughly, and intensity declines slightly.
In conjunction with preferred embodiment and exemplary example, the present invention is had been described in detail above. But need to stateThat these detailed description of the invention are only to illustrative explanation of the present invention, protection scope of the present invention are not formed to any limitSystem. In the situation that not exceeding the present invention's spirit and protection domain, can carry out the technology of the present invention content and embodiment thereofVarious improvement, of equal value replacement or modification, these all fall within the scope of protection of the present invention. Protection scope of the present invention is with appended powerProfit requires to be as the criterion.
Claims (10)
1. a yellow uitramarine composition, is characterized in that, it contains at least one suc as formula compound and pigment yellow shown in (I)93，
In formula (I) compound, X, Y are fatty amido or aryl amine,
Preferred described fatty amido is straight chain saturated fat amido, is preferably C6～C22Straight chain alkylamino radical, more preferably C12～C18Straight chain alkylamino radical, and/or
Preferred described aryl amine, for replacing or unsubstituted anilino-, is preferably by one of alkyl, alkoxyl or halogen atom or manyIndividual replaced anilino-, the anilino-more preferably being replaced by methyl and/or chlorine atom.
2. composition according to claim 1, is characterized in that,
In formula (I) compound, X, Y are selected from suc as formula group shown in (II) or formula (III),
3. composition according to claim 1 and 2, is characterized in that,
In formula (I) compound, X, Y can be identical or different, and preferably X is to be base shown in formula (II) suc as formula group shown in (III) and YGroup, or X is for being group shown in formula (III) suc as formula group shown in (II) and Y, and more preferably formula (I) is compound as follows:
4. according to the composition one of claims 1 to 3 Suo Shu, wherein,
Pigment yellow 93 can additionally add, and also can react to synthesize with compound one shown in formula (I) obtains.
5. a method of preparing composition as described in one of claim 1 to 4, is characterized in that,
Carry out condensation reaction suc as formula the compound shown in (IV) and fatty amine and arylamine, obtain compound shown in formula (I),
The optional pigment yellow 93 that adds.
6. method according to claim 5, is characterized in that, the method comprises the following steps:
To be dissolved in solvent suc as formula the compound shown in (IV),
Add wherein fatty amine and arylamine, the lower insulation reaction of heating,
Reaction finishes rear cooling, filtration, obtains compound shown in formula (I).
7. according to the method described in claim 5 or 6, it is characterized in that,
0.5～10h is carried out in described condensation reaction at 100～200 DEG C, preferably at 120～180 DEG C, carries out 1～6h, more preferablyAt 140～160 DEG C, carry out 2～4h.
8. according to the method one of claim 5 to 7 Suo Shu, it is characterized in that,
Described fatty amine is straight chain saturated fat amine, is preferably C6～C22Straight chain alkanamine, more preferably C12～C18Straight chain alkaneAmine, for example, be octadecylamine, and/or
Described arylamine, for replacing or unsubstituted aniline, is preferably by one or more of alkyl, alkoxyl or halogen atom and replacesAniline, the aniline more preferably being replaced by methyl and/or chlorine atom, for example 3-methyl-2-chloroaniline, and/or
The mole of described fatty amine is 2～60% of arylamine mole, preferably 4～40%, more preferably 5～20%.
9. according to the method one of claim 6 to 8 Suo Shu, it is characterized in that,
Described solvent is halogeno-benzene or alkylbenzene, is preferably dichloro-benzenes, trichloro-benzenes, dimethyl benzene or trimethylbenzene, and/or
Preferably first add fatty amine, then add arylamine.
10. the purposes of the composition making according to one of claim 1 to 4 or according to the described method of one of claim 5 to 9,Use as yellow uitramarine.
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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 |
| US5559216A (en) * | 1992-09-02 | 1996-09-24 | Hoechst Ag | Single-step process for the preparation of bis-(acetoacetylamino) benzene disazo pigments |
| CN103048900A (en) * | 2011-10-12 | 2013-04-17 | 佳能株式会社 | Toner including compound having bisazo skeleton |
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2016
- 2016-03-08 CN CN201610128207.6A patent/CN105602285B/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 |
| US5559216A (en) * | 1992-09-02 | 1996-09-24 | Hoechst Ag | Single-step process for the preparation of bis-(acetoacetylamino) benzene disazo pigments |
| CN103048900A (en) * | 2011-10-12 | 2013-04-17 | 佳能株式会社 | Toner including compound having bisazo skeleton |
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