CN105602285B - Color compositions containing octadecylamine base disazo condensation compound and preparation method thereof - Google Patents
Color compositions containing octadecylamine base disazo condensation compound and preparation method thereof Download PDFInfo
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- CN105602285B CN105602285B CN201610128207.6A CN201610128207A CN105602285B CN 105602285 B CN105602285 B CN 105602285B CN 201610128207 A CN201610128207 A CN 201610128207A CN 105602285 B CN105602285 B CN 105602285B
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- 0 CC(C(*c(cc(cc1)C(I)=O)c1N)C(*c1c(C)cc(CC*#CC([C@@](*=*c2cc(C(*)O)ccc2*)C(C)=O)=O)c(C)c1)=O)=O Chemical compound CC(C(*c(cc(cc1)C(I)=O)c1N)C(*c1c(C)cc(CC*#CC([C@@](*=*c2cc(C(*)O)ccc2*)C(C)=O)=O)c(C)c1)=O)=O 0.000 description 2
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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
The invention discloses a kind of containing color compositions of disazo condensation compound and preparation method thereof shown in following structure,
Description
Technical field
The invention belongs to chemical dye field, and in particular to a kind of pigment containing octadecylamine base disazo condensation compound
Composition and preparation method thereof.
Background technology
Biacetyl antifebrin azo condensation pigment passes through amido link on the basis of biacetyl acetophenone amine pigment molecule
Couple a substitution aromatic ring again at molecule both ends.Such pigment, its molecular weight is big, and tinting strength, tinting power and fastness ability are stronger, especially introduce
More amide groups, make compound be more likely formed intramolecular and intermolecular hydrogen bonding, and such molecular structure substantially improves face
Every fastness ability of material, particularly heat resistance and solvent resistance.In coloring plastic, resistance to migration improves a lot.But
Because production cost is higher, therefore price is high, is mainly used in the occasion of top grade.Wherein pigment yellow 93 shows that a kind of bright green light is yellow
Color, due to its remarkable heat resistance, light resistance and good resistance to migration, have in high-grade printing-ink, sedan car top coat preferably
Application, be also widely used in plastic pvc, PP and LDPE.
Patent US3413279 discloses a kind of yellow 93 preparation method, and this method is by the chlorobenzene first of diazo component 3- amino -4
The diazol of acid is coupled with the chloro- 5- methyl biacetyl acetyl-p-phenylenediamines of coupling component 2- at 105-110 DEG C in o-dichlorohenzene
Bisazo dicarboxylic acids intermediate is made, because the method is heterogeneous reaction, causes reaction to be difficult to completely, yield is relatively low.
The pigmentation method of pigment yellow 93 is disclosed in patent US5194088.By crude pigment product, anhydrous slufuric acid in this method
Sodium and steel ball are placed in ball grinder, at room temperature ball milling 48h.Treat that ball milling finishes, at room temperature by ball milling crude product in dimethyl sulfoxide (DMSO)
2h is handled, the product of pigment yellow 93 can be obtained through hot water mashing washing, drying.
According to market survey, although Huang 93 has high-fire resistance, good resistance to migration, the transparency of pigment yellow 93 needs to change
Kind property, current Huang 93 is using preparation method and pigmentation method disclosed in foregoing invention, and the obtained product transparency is still not
Satisfactory, for disazo condensation class pigment, it is adjusted by the particle of itself, is difficult to have breakthrough to enter in the transparency
Exhibition.Present invention introduces the synthesis mode of mixed crystal, and to obtain high transparency, while heat resistance has the excellent derivative greatly improved.
The content of the invention
In order to overcome above mentioned problem, the present inventor is studied disazo pigment and preparation method thereof, obtained with keen determination
A kind of green glow is stronger, the transparent disazo condensation compound significantly improved, and itself and pigment yellow 93 are mixed to get into a kind of Huang
Color color compositions, its heat resistance, solvent resistance, dispersiveness, rheological characteristic is suitable with existing pigment yellow 93 on ink, is applicable
In the ink of the high grade of transparency.
It is an object of the invention to provide following aspect：
(1) a kind of yellow pigment composition, it contains at least one compound and pigment yellow 93 as shown in formula (I),
In formula (I) compound, X, Y are fatty amido or aryl amine,
It is preferred that the fatty amido is straight chain saturated fat amido, preferably C6~C22Straight chain alkylamino radical, more preferably
C12~C18Straight chain alkylamino radical, and/or
It is preferred that the aryl amine is substituted or unsubstituted anilino-, preferably by one of alkyl, alkoxy or halogen atom
Or multiple substituted anilino-s, the anilino- more preferably substituted by methyl and/or chlorine atom；
(2) composition described in (1) as described above, it is characterised in that
In formula (I) compound, X, Y are selected from the group as shown in formula (II) or formula (III),
(3) composition described in (1) or (2) as described above, it is characterised in that
In formula (I) compound, X, Y can be with identical or different, and preferably X is formula (II) institute for the group as shown in formula (III) and Y
Show group, or, X is that group and Y as shown in formula (II) are group shown in formula (III), the change that more preferably formula (I) is as follows
Compound：
(4) composition described in one of (1) to (3) as described above, it is characterised in that
Pigment yellow 93 can be added additionally, and the synthesis that can also be reacted with compound one shown in formula (I) obtains；
(5) one kind prepare as described above (1) to the method for one of (4) composition, it is characterised in that will be such as formula (IV) institute
The compound shown carries out condensation reaction with fatty amine and arylamine, obtains compound shown in formula (I),
Optionally addition pigment yellow 93；
(6) method described in (5) as described above, it is characterised in that this method comprises the following steps：
Compound as shown in formula (IV) is dissolved in solvent,
Fatty amine and arylamine are added thereto, heat lower insulation reaction,
Cooling, filtering, obtain compound shown in formula (I) after reaction terminates；
(7) method described in (5) or (6) as described above, it is characterised in that
The condensation reaction carries out 0.5~10h at 100~200 DEG C, 1~6h is carried out preferably at 120~180 DEG C, more
It is preferred that 2~4h is carried out at 140~160 DEG C；
(8) method described in one of (5) to (7) as described above, it is characterised in that
The fatty amine is straight chain saturated fat amine, preferably C6~C22Straight chain alkanamine, more preferably C12~C18It is straight
Chain alkanamine, for example, octadecylamine, and/or
The arylamine is substituted or unsubstituted aniline, preferably by one or more institutes of alkyl, alkoxy or halogen atom
Substituted aniline, the aniline more preferably substituted by methyl and/or chlorine atom, such as 3- methyl -2- chloroanilines, and/or
The mole of the fatty amine is the 2~60% of arylamine mole, preferably 4~40%, more preferably 5~20%；
(9) method described in one of (6) to (8) as described above, it is characterised in that
The solvent is halogeno-benzene or alkylbenzene, preferably dichloro-benzenes, trichloro-benzenes, dimethyl benzene or trimethylbenzene, and/or
It is preferred that first adding fatty amine, arylamine is added；
(10) purposes of composition made from one of (1) to (4) or (5) to one of (9) methods described as described above, as Huang
Color pigment uses.
Beneficial effect includes possessed by the present invention：
(1) present invention pigment yellow 93 be condensed it is amidated during add specific fatty amine, mixed crystal synthesis is a kind of double
Azo condensation compound, its green glow is stronger, and the transparency significantly improves, heat resistance, solvent resistance, dispersiveness, rheological characteristic on ink
It is suitable with existing pigment yellow 93, suitable for 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 raw material is cheap
It is easy to get, suitable for large-scale industrial production；
(3) color compositions provided by the invention mix the above-mentioned disazo condensation chemical combination of special ratios in pigment yellow 93
Thing, the transparency of pigment is significantly improved, and its green glow is stronger, colouring agent can be used as to be used in a variety of systems.
Brief description of the drawings
Fig. 1 shows solid beautiful yellow 3GNP thoroughly testing electronic microscope figure；
Fig. 2 shows the testing electronic microscope figure of disazo condensation compound made from embodiment 1；
Fig. 3 shows solid beautiful yellow 3GNP thoroughly X ray diffracting spectrum；
Fig. 4 shows the X ray diffracting spectrum of disazo condensation compound made from embodiment 1；
Fig. 5 shows the infrared spectrogram of pigment yellow 93 made from comparative example；
Fig. 6 shows the infrared spectrogram of disazo condensation compound made from embodiment 1.
Embodiment
Below by accompanying drawing, experimental example and embodiment, the present invention is described in more detail.Pass through these explanations, the present invention
The characteristics of and advantage will become more apparent from clearly.
According to the first aspect of the invention, there is provided a kind of yellow pigment composition, it contains at least one as shown in formula (I)
Compound and pigment yellow 93,
In formula (I) compound, X, Y are fatty amido or aryl amine.
In a preferred embodiment in accordance with the present invention, the fatty amido is straight chain saturated fat amido, preferably C6
~C22Straight chain alkylamino radical, more preferably C12~C18Straight chain alkylamino radical, and/or
The aryl amine is substituted or unsubstituted anilino-, preferably by the one or more of alkyl, alkoxy or halogen atom
Individual substituted anilino-, the anilino- more preferably substituted by methyl and/or chlorine atom.
Preferably, in formula (I) compound, X, Y are selected from the group as shown in formula (II) or formula (III),
In formula (I) compound, X, Y can be with identical or different, and preferably X is formula (II) institute for the group as shown in formula (III) and Y
Show group, or, X is that group and Y as shown in formula (II) are group shown in formula (III), the change that more preferably formula (I) is as follows
Compound：
In a preferred embodiment in accordance with the present invention, in the color compositions, compound rubs as shown in formula (I)
Your amount is the 1~50% of the mole of pigment yellow 93, preferably 3~30%, more preferably 5~20%.
Wherein, pigment yellow 93 can be added additionally, and the synthesis that can also be reacted 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 to
Solvent borne, dispersiveness, rheological characteristic is suitable with existing pigment yellow 93 on ink, and it is mixed with special ratios with pigment yellow 93
Obtained yellow pigment composition, its transparency significantly improve, and colouring agent can be used as to be used in a variety of systems, such as applied to height
In the ink of transparency.
According to the second aspect of the invention, there is provided a kind of method for preparing color compositions as described above, will be such as formula (IV)
Shown compound carries out condensation reaction with fatty amine and arylamine, obtains compound shown in formula (I), optionally adds pigment yellow 93,
Wherein, the fatty amine is straight chain saturated fat amine, preferably C6~C22Straight chain alkanamine, more preferably C12~
C18Straight chain alkanamine, for example, octadecylamine, and/or
The arylamine is substituted or unsubstituted aniline, preferably by one or more institutes of alkyl, alkoxy or halogen atom
Substituted aniline, the aniline more preferably substituted by methyl and/or chlorine atom, such as 3- methyl -2- chloroanilines, and/or
The mole of the fatty amine is the 2~60% of arylamine mole, preferably 4~40%, more preferably 5~20%.
This method specifically includes following steps：Compound as shown in formula (IV) is dissolved in solvent, adds fat thereto
Fat amine and arylamine, lower insulation reaction is heated, cooling, filtering, obtain compound shown in formula (I) after reaction terminates.
Wherein, the solvent is halogeno-benzene or alkylbenzene, preferably dichloro-benzenes, trichloro-benzenes, dimethyl benzene or trimethylbenzene,
And/or
It is preferred that first adding fatty amine, arylamine is added, and/or
The condensation reaction is carried out 0.5~10 hour at 100~200 DEG C, and 1~6 is carried out preferably at 120~180 DEG C
Hour, carried out 2~4 hours more preferably at 140~160 DEG C.
In a preferred embodiment in accordance with the present invention, methods described includes：Compound as shown in formula (IV) is dissolved in
Dichloro-benzenes, the dichlorobenzene solution of fatty amine and arylamine is sequentially added dropwise thereto, 140~160 DEG C is heated to after being added dropwise, insulation
Reaction 2~4 hours, reaction cools after terminating, filtering, is dried after filter cake methanol and water washing, obtains chemical combination shown in formula (I)
Thing.
Pigment yellow 93 can be added additionally, and the synthesis that can also be reacted with compound one shown in formula (I) obtains.Extra addition
During pigment yellow so that the mole of pigment yellow 93 is 1~50%, preferably 3~30% of the compound mole as shown in formula (I),
More preferably 5~20%.
According to the third aspect of the invention we, there is provided the purposes of color compositions as described above, it is used as yellow uitramarine.
It is preferred that above-mentioned color compositions provided by the invention are used in ink, coating and plastic products as colouring agent, its
Green glow is stronger, and transparency significantly improves.
Embodiment
Embodiment 1
By in the 250ml four-hole boiling flasks of 30g acyl chlorides compound (0.0144mol) input dichloro-benzenes containing 100g, oil bath is warming up to
130 DEG C, 0.77g (0.00288mol) octadecylamine, and the two of 3.67g (0.02592mol) 3- chloro-2-methyl anilines are added dropwise
Chlorobenzene solution, 30min is added dropwise, 150 DEG C are warming up to after being added dropwise and is incubated 3 hours.Cooling filtering, washed after methanol washing, it is molten
Agent is reclaimed, and filter cake drying, obtains the 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.
Examination of infrared spectrum is carried out using infrared spectrometer, as a result as shown in Figure 6.As seen from Figure 6, due to introducing octadecane
Amine so that with the presence of multiple methylene in product, its infrared spectrogram is in vas≈2925cm-1And vs≈2850cm-1Place has substantially
Methylene stretching vibration absworption peak, illustrate that embodiment 1 has been made theoretical product, preparation method provided by the invention is stable, can
Lean on.
Its elementary analysis result is：C, 44.11；H, 37.89；Cl, 4.88；N, 8.22；O, 6.The molecular formula thereby determined that
For C44.1H38.1N8.1O6Cl4.9.It is computed, C, the increase of H element content, Cl constituent contents are reduced in product made from embodiment 1,
Meet the molecular composition of modified structure.
Embodiment 2
By in the 250ml four-hole boiling flasks of 30g acyl chlorides compound (0.0144mol) input dichloro-benzenes containing 100g, oil bath is warming up to
130 DEG C, 1.16g (0.00432mol) octadecylamine, and the two of 3.46g (0.02448mol) 3- chloro-2-methyl anilines are added dropwise
Chlorobenzene solution, 30min is added dropwise, 150 DEG C are warming up to after being added dropwise and is incubated 3 hours.Cooling filtering, washed after methanol washing, it is molten
Agent is reclaimed, and filter cake drying, obtains the disazo condensation compound.
Its electron microscope observation result, X-ray diffractogram and infrared spectrogram are similar with the products obtained therefrom of embodiment 1；
Its elementary analysis result is：C, 44.56；H, 38.99；Cl, 4.80；N, 8.07；O, 6.The molecular formula thereby determined that
For C44.65H39.65N8.15O6Cl4.85.It is computed, C, the increase of H element content, Cl constituent contents subtract in product made from embodiment 2
It is few, also comply with the molecular composition of modified structure.
Comparative example
By in the 250ml four-hole boiling flasks of 30g acyl chlorides compound (0.0144mol) input dichloro-benzenes containing 100g, oil bath is warming up to
130 DEG C, the dichlorobenzene solution of 4.08g (0.0288mol) 3- chloro-2-methyl anilines is added dropwise, 30min is added dropwise, is risen after being added dropwise
Warm to 150 DEG C are incubated 3 hours.Cooling filtering, wash, solvent recovery, filter cake drying, obtain as shown in formula (V) after methanol washing
Compound, as pigment yellow 93.
Only have a small amount of methylene, methyl to exist from formula (V) structure, in pigment yellow 93 made from comparative example 1, its is red
External spectrum result is as shown in figure 5, in vas≈2925cm-1And vs≈2850cm-1The only unconspicuous methylene stretching vibration in place is inhaled
Receive peak.
Its elementary analysis result is：C, 42.71；H, 34.85；Cl, 5.07；N, 7.86；O, 6.The molecular formula thereby determined that
For C43H35N8O6Cl5。
Experimental example
All verification test standards are the solid beautiful yellow 3GNP thoroughly of Ciba companies.
The electron-microscopic analysis of experimental example 1
Using electron microscope, disazo condensation compound made from solid beautiful yellow 3GNP thoroughly, embodiment 1 is surveyed respectively
Examination, is as a result shown in Fig. 1~2.
As shown in Fig. 1~2, its particle crystallization state of product produced by the present invention clearly changes.
Experimental example 2X x ray diffraction analysis xs
Using X-ray diffractometer, disazo condensation compound made from solid beautiful yellow 3GNP thoroughly, embodiment 1 is carried out respectively
Test, is as a result shown in Fig. 3~4.
Comparison diagram 3 and Fig. 4 understand that it is solid U.S. saturating that its crystal habit of product made from the embodiment of the present invention 1 is different from standard items
Yellow 3GNP, its distinguishing characteristics are that X-ray diffraction Fig. 2 θ angles are to have 3 compared with weak absorbing peak at double at 44.5 °, 64.8 °, 78.2 °
Number weakens, it can be seen that, its microstructure of product produced by the present invention clearly changes.
Compare coloured light, tinctorial strength and transparency in the ink system of experimental example 3
Coloured light comparative approach：Pigment sample 0.200g made from embodiment 1~2 is dispersed into 0.600 linseed oil,
Totally 250 circles are scattered for plain grinding instrument 5 times, pigment difference compared with disperseing scraper plate with 93 identical ink of pigment yellow made from comparative example.
Tinctorial strength comparative approach：By pigment sample 0.050g made from embodiment 1~2, and 1.000g titanium dioxides
(R902) in the dispersed linseed oil to 1.000g, totally 250 circles are scattered for plain grinding instrument 5 times, with comparative example made from the phase of pigment yellow 93
Disperse scraper plate with ink and compare pigment difference.
Transparency comparative approach：Paper to be printed on black ribbon line is compared as background, the method for naked eyes judgement.
Coloured light, tinctorial strength and transparency comparative result in the ink system of table 1.
| Gu beautiful yellow 3GNP thoroughly | Comparative example | Embodiment 1 | Embodiment 2 | |
| Form and aspect | Standard | It is slightly red | It is slightly green | It is greener |
| Covering power | Standard | It is micro- high | It is more saturating | It is more saturating |
| Intensity | Standard | 100 | 104 | 106 |
As shown in Table 1, for product made from the embodiment of the present invention 1~2 compared with standard items, its coloured light is obvious partially green, transparent
Degree greatly improves, and pigment yellow 93 made from comparative example is then obvious slightly red compared with standard items, and covering is higher, and transparency is relatively low.
The ink fluidity of experimental example 4 compares
The coloured light containing pigment sample for carrying out preparing when coloured light compares in experimental example 3 is disperseed into black 0.100g and is placed in metal
Circular glass piece center in fixed disk, upper Circular glass piece is placed on the Circular glass piece in metal fixed disk, centre is had black portion
It is point overlapping, upper 200g counterweights (paying attention to metal fixed disk keep level) are pressed immediately, start timing；
Counterweight is removed after 15min, the maximum and minimum value of ink cylinder diameter are measured with transparent gage, if maximum
The difference of value and minimum value is 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, the results are shown in Table 2.
The ink fluidity measurement result of table 2.
| Gu beautiful yellow 3GNP thoroughly | Comparative example | Embodiment 1 | Embodiment 2 | |
| Fluidity/mm | 23.2 | 18.9 | 20.5 | 21.5 |
As shown in table 2, its ink fluidity of product made from embodiment 1~2 has clear improvement.
The plastics of experimental example 5 (LDPE) system compares coloured light, tinctorial strength and covering power
True qualities：Weigh pigment yellow 93 each 0.1500g, LDPE made from pigment sample made from embodiment 1~2 and comparative example
After resin is placed on two roller machines (120 DEG C), motor is opened, preplasticizing about 1 minute is (when two roller machines roll, before resin should be adhered to
On roller, must be refunded again between two rollers from the material to be dropped between two rollers), after resin completely plasticizing, the above-mentioned face that will weigh up
Material sample is slowly homogeneously added into the plastics plastified, is kneaded on two roller machines, after resin and pigment are thoroughly mixed,
Start timing, and upset 6 minutes is carried out with bamboo chip scraper is continual, close motor, it is 5mm to adjust roller spacing, opens motor, after
It is continuous to be kneaded 0.5 minute (color chips is adhered on preliminary roller) membrane afterwards, comparing embodiment and tabletting obtained by comparative example.
Reduced shade：Weigh 93 each 0.0250g of pigment yellow made from pigment sample and comparative example made from embodiment 1~2,
0.2500g titanium dioxides, LDPE resin are placed on heat on two roller machines and after 20 seconds, open motor, and preplasticizing (is rolled for about 1 minute in two roller machines
When dynamic, resin should be adhered on preliminary roller, must be refunded again between two rollers from the material to be dropped between two rollers), treat that resin is moulded completely
After change, load weighted pigment and titanium dioxide are slowly homogeneously added into the plastics plastified, is kneaded, treated on two roller machines
After resin is thoroughly mixed with pigment, start timing, and upset 6 minutes is carried out with bamboo chip scraper is continual, close motor, adjust roller
Spacing is 5mm, opens motor, continues to be kneaded 0.5 minute (color chips should be adhered on preliminary roller) membrane afterwards；Standard items are solid beautiful thoroughly yellow
3GNP independent tablettings according to the method described above.
Using the solid beautiful yellow 3GNP thoroughly of standard items as reference, the tinctorial strength of sample is evaluated by Computer color testing instrument.
Coloured light and covering power comparative result in the plastics of table 3. (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 of height | 2 grades thoroughly | 3 grades thoroughly |
Tinctorial strength comparative result in the plastics of table 4. (LDPE) system
| Gu beautiful yellow 3GNP thoroughly | Comparative example | Embodiment 1 | Embodiment 2 | |
| Relative intensity | 100.000 | 98.962 | 97.926 | 95.368 |
Heat resistance test result in the plastics of table 5. (LDPE) system
The above results show that the modified pigment prepared by embodiment 1~2 is partially green using coloured light in plastics system, but does not have
Have green mutually obvious in ink system, covering power is partially saturating, and also without obvious in ink system, intensity slightly declines.
Application of the experimental example 6 in NC ink
28.8g celluloid lacquers, 32.0g absolute ethyl alcohols, 120g beades, 19.2g face are sequentially added into vial
Material, vibrated 50 minutes with vibration case after sealing, standing is removed after shaking well 15 minutes, obtain dispersion.
True qualities：The above-mentioned dispersions of 12.0g are taken in plastic cup, 18.0g Letdown Varnish is added and is stirred evenly with rubber head,
Pigment sample made from embodiment 1~2, comparative example and standard sample are added dropwise a little on PP films with disposable dropper, with silk
Rod (12 μm) spreads to uniform film, is drying and forming-film (the evaluation transparency) after placing 10 minutes.
Pigment sample made from embodiment 1~2, comparative example and standard sample will be added dropwise with disposable dropper a little in band
On black thick stick art paper, 75 μm of wet film makers are put, coating agent which has to be dissolved in alcohol before use is scraped with automatic spray device, are drying and forming-film after placing 10 minutes
(evaluation coloured light and glossiness).
Reduced shade：The above-mentioned dispersions of 1.50g are taken in plastic cup, 13.5g chalks is added, is stirred evenly with rubber head, with disposable
Dropper pigment sample made from embodiment 1~2, comparative example and standard sample will be added dropwise a little on black thick stick art paper, put
Upper 75 μm of wet film makers, coating agent which has to be dissolved in alcohol before use is scraped with automatic spray device, be drying and forming-film after placing 10 minutes, with colour photometer colour examining.
Coloured light and covering power test result in table 6.NC ink systems
| Title | Gu beautiful yellow 3GNP thoroughly | Comparative example | Embodiment 1 | Embodiment 2 |
| Form and aspect | Standard | 2 grades red | 2 grades green | 2 grades green |
| Covering power | Standard | 2 grades of height | 3 grades thoroughly | 4 grades thoroughly |
Tinctorial strength test result in table 7.NC ink systems
| Title | Gu beautiful yellow 3GNP thoroughly | Comparative example | Embodiment 1 | Embodiment 2 |
| Relative intensity | 100.000 | 99.321 | 97.021 | 98.706 |
The above results show, under N/C systems, obvious partially green, the micro- Huang of pigment sample coloured light made from embodiment 1~2, hide
Lid power significantly becomes saturating, and intensity slightly declines.
The present invention is described in detail above in association with preferred embodiment and exemplary example.But need what is stated
It is that these embodiments are only the illustrative explanations to the present invention, do not form any limit to protection scope of the present invention
System.In the case of without departing from spirit and scope of the present invention, the technology of the present invention content and embodiments thereof can be carried out
Various improvement, equivalencing or modifications, these are each fallen within protection scope of the present invention.Protection scope of the present invention is with appended power
Profit requires to be defined.
Claims (16)
1. a kind of yellow pigment composition, it is characterised in that it contains pigment yellow 93 and at least one chemical combination as shown in formula (I)
Thing,
In formula (I) compound, X, Y are fatty amido or aryl amine, and are the group as shown in formula (II) when X, Y difference,
The fatty amido is C6~C22Straight chain alkylamino radical, and
The aryl amine is the anilino- that is substituted by one or more of alkyl, alkoxy or halogen atom.
2. composition according to claim 1, it is characterised in that the fatty amido is C12~C18Straight chain alkylamino radical,
With
The aryl amine is the anilino- that is substituted by methyl and/or chlorine atom.
3. composition according to claim 1 or 2, it is characterised in that
In formula (I) compound, X, Y are selected from the group as shown in formula (II) or formula (III),
4. composition according to claim 3, it is characterised in that
In formula (I) compound, X is that group and Y as shown in formula (III) are group shown in formula (II), or, X is as shown in formula (II)
Group and Y are group shown in formula (III).
A kind of 5. method for preparing the composition as described in one of Claims 1-4, it is characterised in that
Compound as shown in formula (IV) carries out condensation reaction with fatty amine and arylamine, obtains compound shown in formula (I),
Pigment yellow 93 is added,
The fatty amine is C6~C22Straight chain alkanamine, and
The arylamine is the aniline that is substituted by one or more of alkyl, alkoxy or halogen atom.
6. according to the method for claim 5, it is characterised in that this method comprises the following steps：
Compound as shown in formula (IV) is dissolved in solvent,
Fatty amine and arylamine are added thereto, heat lower insulation reaction,
Cooling, filtering, obtain compound shown in formula (I) after reaction terminates.
7. according to the method for claim 5, it is characterised in that
The condensation reaction carries out 0.5~10h at 100~200 DEG C.
8. according to the method for claim 7, it is characterised in that
The condensation reaction carries out 1~6h at 120~180 DEG C.
9. according to the method for claim 8, it is characterised in that
The condensation reaction carries out 2~4h at 140~160 DEG C.
10. the method according to one of claim 5 to 9, it is characterised in that
The mole of the fatty amine is the 2~60% of arylamine mole.
11. according to the method for claim 10, it is characterised in that
The mole of the fatty amine is the 4~40% of arylamine mole.
12. according to the method for claim 11, it is characterised in that
The fatty amine is C12~C18Straight chain alkanamine, and
The arylamine is the aniline that is substituted by methyl and/or chlorine atom, and
The mole of the fatty amine is the 5~20% of arylamine mole.
13. according to the method for claim 12, it is characterised in that
The fatty amine is octadecylamine, and/or the arylamine is 3- chloro-2-methyl anilines.
14. according to the method for claim 6, it is characterised in that
The solvent is halogeno-benzene or alkylbenzene, and/or
Fatty amine is first added, adds arylamine.
15. according to the method for claim 14, it is characterised in that
The solvent is dichloro-benzenes, trichloro-benzenes, dimethyl benzene or trimethylbenzene.
16. according to the purposes of the composition of one of Claims 1-4, used 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 |
-
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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