CN105778564B - Color compositions containing rosin amine disazo condensation compound and preparation method thereof - Google Patents
Color compositions containing rosin amine disazo condensation compound and preparation method thereof Download PDFInfo
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- CN105778564B CN105778564B CN201610130721.3A CN201610130721A CN105778564B CN 105778564 B CN105778564 B CN 105778564B CN 201610130721 A CN201610130721 A CN 201610130721A CN 105778564 B CN105778564 B CN 105778564B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 51
- 239000000203 mixture Substances 0.000 title claims abstract description 30
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 title claims description 12
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 title claims description 12
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 title claims description 12
- 238000009833 condensation Methods 0.000 title abstract description 19
- 230000005494 condensation Effects 0.000 title abstract description 19
- 238000002360 preparation method Methods 0.000 title abstract description 9
- 239000000049 pigment Substances 0.000 claims abstract description 60
- 239000002904 solvent Substances 0.000 claims abstract description 15
- 239000001052 yellow pigment Substances 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 29
- 150000001412 amines Chemical class 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 238000001914 filtration Methods 0.000 claims description 7
- RQRKMXABSUYQBV-UHFFFAOYSA-N 2-chloro-3-methylaniline Chemical class CC1=CC=CC(N)=C1Cl RQRKMXABSUYQBV-UHFFFAOYSA-N 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- 238000006482 condensation reaction Methods 0.000 claims description 6
- 238000009413 insulation Methods 0.000 claims description 4
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical class ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 claims description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical group ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims description 3
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- IBSQPLPBRSHTTG-UHFFFAOYSA-N 1-chloro-2-methylbenzene Chemical group CC1=CC=CC=C1Cl IBSQPLPBRSHTTG-UHFFFAOYSA-N 0.000 claims 2
- 150000004982 aromatic amines Chemical class 0.000 abstract description 17
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract description 16
- 125000003368 amide group Chemical group 0.000 abstract description 5
- 230000000052 comparative effect Effects 0.000 description 23
- 239000000976 ink Substances 0.000 description 22
- 239000000047 product Substances 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 150000002430 hydrocarbons Chemical group 0.000 description 12
- 239000004033 plastic Substances 0.000 description 12
- 229920003023 plastic Polymers 0.000 description 12
- -1 biacetyl acetophenone amine Chemical class 0.000 description 10
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 229920001684 low density polyethylene Polymers 0.000 description 7
- 239000004702 low-density polyethylene Substances 0.000 description 7
- 150000004816 dichlorobenzenes Chemical class 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 238000009738 saturating Methods 0.000 description 5
- 238000010792 warming Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000001448 anilines Chemical class 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- ZUVPLKVDZNDZCM-UHFFFAOYSA-N 3-chloro-2-methylaniline Chemical class CC1=C(N)C=CC=C1Cl ZUVPLKVDZNDZCM-UHFFFAOYSA-N 0.000 description 3
- 238000002441 X-ray diffraction Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 238000000498 ball milling Methods 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 238000013508 migration Methods 0.000 description 3
- 230000005012 migration Effects 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 235000010215 titanium dioxide Nutrition 0.000 description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- 235000017166 Bambusa arundinacea Nutrition 0.000 description 2
- 235000017491 Bambusa tulda Nutrition 0.000 description 2
- 241001330002 Bambuseae Species 0.000 description 2
- 0 CC(C(*)C(*c1c(C)cc(*C([C@@](*=*c2c(C)ccc(C(*c3c(C)c(I)ccc3)=C)c2)C(C)=*)=O)c(C)c1)=*)=* Chemical compound CC(C(*)C(*c1c(C)cc(*C([C@@](*=*c2c(C)ccc(C(*c3c(C)c(I)ccc3)=C)c2)C(C)=*)=O)c(C)c1)=*)=* 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 235000015334 Phyllostachys viridis Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000011425 bamboo Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 235000021388 linseed oil Nutrition 0.000 description 2
- 239000000944 linseed oil Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical class [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 230000019612 pigmentation Effects 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229920002160 Celluloid Polymers 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 1
- 238000010218 electron microscopic analysis Methods 0.000 description 1
- 125000005909 ethyl alcohol group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005360 mashing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/22—Compounds containing nitrogen bound to another nitrogen atom
- C08K5/23—Azo-compounds
- C08K5/235—Diazo and polyazo compounds
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (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 rosin amine 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 two 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, has preferably in high-grade printing-ink, sedan car top coat
Application, be also widely used in plastic pvc, PP and LDPE.
Patent US3413279 discloses a kind of yellow 93 preparation method, and the 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- in o-dichlorohenzene at 105-110 DEG C
Bisazo dicarboxylic acids intermediate is obtained, 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 the method
Sodium and steel ball are placed in ball grinder, at room temperature ball milling 48h.Treat that ball milling is finished, at room temperature by ball milling crude product in dimethyl sulfoxide (DMSO)
Treatment 2h, the product of pigment yellow 93 can be obtained through hot water mashing washing, drying.
According to market survey, although yellow 93 have high-fire resistance, good resistance to migration, the transparency of pigment yellow 93 needs to change
Kind property, using the preparation method and pigmentation method disclosed in foregoing invention, the product transparency for obtaining is still not for current Huang 93
Satisfactory, for disazo condensation class pigment, the particle adjustment that it passes through itself is difficult to have in the transparency and breakthrough enters
Exhibition.Present invention introduces the synthesis mode of mixed crystal, to obtain high transparency, while heat resistance has the excellent derivative for greatly improving.
The content of the invention
In order to overcome above mentioned problem, the present inventor is studied disazo pigment and preparation method thereof with keen determination, is obtained
A kind of green glow is stronger, the transparent disazo condensation compound for significantly improving, and itself and pigment yellow 93 are mixed to get into a kind of Huang
Color color compositions, rheological characteristic is suitable with existing pigment yellow 93 on its heat resistance, solvent resistance, dispersiveness, 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,
Containing fragrant hydrocarbon substituent in the fatty amino structure formula, C is preferably comprised4~C20Fragrant hydrocarbon substituent, and/or
The aryl amine is substituted or unsubstituted anilino-, preferably by the one or more of alkyl, alkoxy or halogen atom
Individual replaced anilino-；
(2) composition as described above described in (1), it is characterised in that
Contain C in the fatty amino structure formula8~C16Fragrant hydrocarbon substituent, and/or
The aryl amine is the anilino- replaced by methyl and/or chlorine atom；
(3) composition as described above described in (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) (1) to one of (3) described composition as described above, it is characterised in that
In formula (I) compound, X, Y can be with identical or different, and preferably X is the group and Y is formula (II) institute as shown in formula (III)
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：
(5) (1) to one of (4) described composition as described above, it is characterised in that
Pigment yellow 93 can be added additionally, it is also possible to acquisition is synthesized together with compound shown in formula (I)；
(6) method that one kind prepares (1) as described above to one of (5) composition, it is characterised in that will be such as formula (IV) institute
The compound for showing carries out condensation reaction with fatty amine and arylamine, obtains compound shown in formula (I),
Optionally add pigment yellow 93；
It is preferred that the method is comprised the following steps：
Step 1, the compound as shown in formula (IV) is dissolved in solvent,
Step 2, fatty amine and arylamine are added thereto to, the lower insulation reaction of heating,
Step 3, reaction are lowered the temperature after terminating, filtering, obtain compound shown in formula (I)；
(7) method as described above described in (6), it is characterised in that
In step 2, the reaction is condensation reaction, 0.5~10h is preferably carried out at 100~200 DEG C, more preferably 120
1~6h is carried out at~180 DEG C, 2~4h is particularly preferably carried out at 140~160 DEG C；
(8) method as described above described in (6) or (7), it is characterised in that
Containing fragrant hydrocarbon substituent in the fatty amine structural formula, C is preferably comprised4~C20Fragrant hydrocarbon substituent, more preferably contain
There is C8~C16Fragrant hydrocarbon substituent, 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 for more preferably being replaced 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) (6) to one of (8) described method as described above, it is characterised in that
The solvent is halogeno-benzene or alkylbenzene, preferably dichloro-benzenes, trichloro-benzenes, dimethylbenzene or trimethylbenzene, and/or
It is preferred that first adding fatty amine, arylamine is added.
(10) purposes of one of (1) to (5) or composition obtained in (6) to one of (9) methods described as described above, as Huang
Color pigment is used.
The present invention have the advantage that including：
(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 is significantly improved, rheological characteristic on heat resistance, solvent resistance, dispersiveness, ink
It is suitable with existing pigment yellow 93, it is adaptable in the ink of the high grade of transparency；
(2) preparation method of the disazo condensation compound that the present invention is provided is simple, and easily-controlled reaction conditions, raw material is cheap
It is easy to get, is suitable to large-scale industrial production；
(3) color compositions that the present invention is provided mix the above-mentioned disazo condensation chemical combination of special ratios in pigment yellow 93
Thing, significantly improves the transparency of pigment, and its green glow is stronger, can be used in various systems as colouring agent.
Brief description of the drawings
Fig. 1 shows the testing electronic microscope figure of solid beautiful Huang 3GNP thoroughly；
Fig. 2 shows the testing electronic microscope figure of disazo condensation compound obtained in embodiment 1；
Fig. 3 shows the X ray diffracting spectrum of solid beautiful Huang 3GNP thoroughly；
Fig. 4 shows the X ray diffracting spectrum of disazo condensation compound obtained in embodiment 1；
Fig. 5 shows the infrared spectrogram of pigment yellow 93 obtained in comparative example；
Fig. 6 shows the infrared spectrogram of disazo condensation compound obtained in embodiment 1.
Specific embodiment
Below by accompanying drawing, experimental example and embodiment, the present invention is described in more detail.Illustrated by these, 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, fragrant hydrocarbon substituent is contained in the fatty amino structure formula, preferably
Contain C4~C20Fragrant hydrocarbon substituent, further preferably C8~C16Fragrant hydrocarbon substituent, and/or
The aryl amine is substituted or unsubstituted anilino-, preferably by the one or more of alkyl, alkoxy or halogen atom
Individual replaced anilino-, the anilino- for more preferably being replaced 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 the group and Y is formula (II) institute as shown in formula (III)
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, it is also possible to acquisition is synthesized together with compound shown in formula (I).
The green glow of the above-mentioned disazo condensation compound that the present invention is provided is stronger, and the transparency is significantly improved, its heat resistance, resistance to
Rheological characteristic is suitable with existing pigment yellow 93 on solvent borne, dispersiveness, ink, and it is mixed with special ratios with pigment yellow 93
The yellow pigment composition for obtaining, its transparency is significantly improved, and can be used in various systems as colouring agent, for example, be 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 addition pigment yellow 93
Wherein, C is preferably comprised containing fragrant hydrocarbon substituent in the fatty amine structural formula4~C20Fragrant hydrocarbon substituent, it is more excellent
Choosing contains C8~C16Fragrant hydrocarbon substituent, 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 for more preferably being replaced 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%.
The method specifically includes following steps：Compound as shown in formula (IV) is dissolved in solvent, fat is added thereto to
Fat amine and arylamine, the lower insulation reaction of heating, reaction is lowered the temperature after terminating, filtering, obtains compound shown in formula (I).
Wherein, the solvent is halogeno-benzene or alkylbenzene, preferably dichloro-benzenes, trichloro-benzenes, dimethylbenzene 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 preferably carried out at 120~180 DEG C
Hour, more preferably carried out at 140~160 DEG C 2~4 hours.
In a preferred embodiment in accordance with the present invention, methods described includes：Compound as shown in formula (IV) is dissolved in
Dichloro-benzenes, is sequentially added dropwise the dichlorobenzene solution of fatty amine and arylamine thereto, and 140~160 DEG C, insulation are heated to after completion of dropping
Reaction 2~4 hours, reaction is lowered the temperature after terminating, filtering, is dried after filter cake methyl alcohol and water washing, obtains chemical combination shown in formula (I)
Thing.
Pigment yellow 93 can be added additionally, it is also possible to acquisition is synthesized together with compound shown in formula (I).Extra addition
During pigment yellow so that the mole of pigment yellow 93 is 1~50% of the compound mole as shown in formula (I), preferably 3~30%,
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 the above-mentioned color compositions that the present invention is provided are used in ink, coating and plastic products as colouring agent, its
Green glow is stronger, and transparency is significantly improved.
Embodiment
Embodiment 1
By in 30g acyl chlorides compound (0.0144mol) 250ml four-hole boiling flasks of the input containing 100g dichloro-benzenes, oil bath is warming up to
130 DEG C, be added dropwise 0.84g (0.00288mol) rosin amine, and 3.67g (0.02592mol) 3- chloro-2-methyl anilines dichloro
Benzole soln, is added dropwise 30min, 150 DEG C is warming up to after completion of dropping and is incubated 3 hours.Cooling filtering, washes, solvent after methyl alcohol washing
Reclaim, 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 rosin
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 obtained theoretical product, preparation method stabilization that the present invention is provided, can
Lean on.
Its elementary analysis result is：C, 44.32；H, 37.15；Cl, 4.96；N, 8.09；O, 6.The molecular formula for thereby determining that
It is C44.3H37.3N8.1O6Cl4.9.It is computed, C, H element content increase in product obtained in embodiment 1, Cl constituent contents are reduced,
Meet the molecular composition of modified structure.
Embodiment 2
By in 30g acyl chlorides compound (0.0144mol) 250ml four-hole boiling flasks of the input containing 100g dichloro-benzenes, oil bath is warming up to
130 DEG C, be added dropwise 1.25g (0.00432mol) rosin amine, and 3.46g (0.02448mol) 3- chloro-2-methyl anilines dichloro
Benzole soln, is added dropwise 30min, 150 DEG C is warming up to after completion of dropping and is incubated 3 hours.Cooling filtering, washes, solvent after methyl alcohol washing
Reclaim, 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, 44.85；H, 38.56；Cl, 4.79；N, 8.21；O, 6.The molecular formula for thereby determining that
It is C44.95H38.45N8.15O6Cl4.85.It is computed, C, H element content increase in product obtained in embodiment 2, Cl constituent contents subtract
It is few, also comply with the molecular composition of modified structure.
Comparative example
By in 30g acyl chlorides compound (0.0144mol) 250ml four-hole boiling flasks of the input containing 100g dichloro-benzenes, 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, risen after completion of dropping
Warm to 150 DEG C are incubated 3 hours.Cooling filtering, is washed, solvent recovery after methyl alcohol washing, and filter cake drying is obtained as shown in formula (V)
Compound, as pigment yellow 93.
Only have a small amount of methylene, methyl to exist from formula (V) structure, in pigment yellow 93 obtained in 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 for thereby determining that
It is C43H35N8O6Cl5。
Experimental example
All verification test standards are the solid beautiful Huang 3GNP thoroughly of Ciba companies.
The electron-microscopic analysis of experimental example 1
Using electron microscope, solid beautiful Huang 3GNP, disazo condensation compound obtained in embodiment 1 thoroughly are surveyed respectively
Examination, is as a result shown in Fig. 1~2.
As shown in Fig. 1~2, its particle crystallization state of product clearly changes obtained in the present invention.
Experimental example 2X x ray diffraction analysis xs
Using X-ray diffractometer, solid beautiful Huang 3GNP, disazo condensation compound obtained in embodiment 1 thoroughly are 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 obtained in the embodiment of the present invention 1 is different from standard items
Yellow 3GNP, its distinguishing characteristics is X-ray diffraction Fig. 2 θ angles to have 3 compared with weak absorbing peak at double at 44.5 °, 64.8 °, 78.2 °
Number weakens, meanwhile, 2 θ angles are that absworption peak is changed into 4.8 ° and 9.0 ° of two absworption peaks at 7.1 °, it can be seen that, the present invention is obtained
Product its microstructure 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 obtained in embodiment 1~2 is dispersed into 0.600 linseed oil,
The 5 totally 250 circle dispersions of plain grinding instrument, pigment difference is compared with the identical ink of pigment yellow obtained in comparative example 93 dispersion scraper plate.
Tinctorial strength comparative approach：By pigment sample 0.050g obtained in embodiment 1~2, and 1.000g titanium dioxides
(R902) in the dispersed linseed oil to 1.000g, 5 totally 250 circle dispersions of plain grinding instrument, with the phase of pigment yellow obtained in comparative example 93
Compare pigment difference with ink dispersion scraper plate.
Transparency comparative approach：To be printed on the paper of black ribbon line as background, the method that naked eyes judge is compared.
Coloured light, tinctorial strength and transparency comparative result in the ink system of table 1.
| Gu beautiful Huang 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 | 97 | 95 |
As shown in Table 1, product obtained in the embodiment of the present invention 1~2 compares with standard items, and its coloured light is substantially partially green, transparent
Degree is greatly improved, and pigment yellow 93 obtained in comparative example compares then substantially slightly red with standard items, and covering is higher, and transparency is relatively low.
The ink fluidity of experimental example 4 compares
The dispersion of the coloured light containing the pigment sample ink 0.100g that will carry out being prepared when coloured light compares in experimental example 3 is placed in metal
Circular glass piece center in fixed disk, on the Circular glass piece that upper Circular glass piece is placed in metal fixed disk, makes centre have black portion
Divide and overlap, upper 200g counterweights (noting metal fixed disk holding level) are pressed immediately, start timing；
Counterweight is removed after 15min, the maximum and minimum value of ink cylinder diameter is measured with transparent gage, if maximum
The difference of value and minimum value is more than or equal to 2mm, then experiment is re-started.
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 Huang 3GNP thoroughly | Comparative example | Embodiment 1 | Embodiment 2 | |
| Fluidity/mm | 23.2 | 18.9 | 21.0 | 22.8 |
As shown in table 2, its ink fluidity of product obtained in embodiment 1~2 has clear improvement.
Experimental example 5 plastics (LDPE) system compares coloured light, tinctorial strength and covering power
True qualities：Weigh pigment sample and pigment yellow 93 each 0.1500g, LDPE obtained in comparative example obtained in embodiment 1~2
After resin is placed on two roller machines (120 DEG C), motor is opened, preplasticizing about 1 minute is (when two roller machines are rolled, before resin should be sticked to
On roller, must be refunded again between two rollers from the material dropped between two rollers), after resin is plastified completely, the above-mentioned face that will be weighed up
Material sample is slowly homogeneously added into the plastics for having plastified, and 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 knead 0.5 minute (color chips is sticked on preliminary roller) membrane afterwards, comparing embodiment and comparative example gained compressing tablet.
Reduced shade：Weigh pigment sample obtained in embodiment 1~2 and each 0.0250g of pigment yellow 93 obtained in comparative example,
0.2500g titanium dioxides, LDPE resin is placed on heat on two roller machines and after 20 seconds, opens motor, and preplasticizing (is rolled for about 1 minute in two roller machines
When dynamic, resin should be sticked on preliminary roller, must be refunded again between two rollers from the material 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 for having plastified, are kneaded on two roller machines, treated
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 knead 0.5 minute (color chips should be sticked on preliminary roller) membrane afterwards；Standard items are solid beautiful thoroughly yellow
3GNP independent compressing tablets according to the method described above.
With the solid beautiful Huang 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 table 3. plastics (LDPE) system
| Title | Gu beautiful Huang 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 4. plastics (LDPE) system
| Gu beautiful Huang 3GNP thoroughly | Comparative example | Embodiment 1 | Embodiment 2 | |
| Relative intensity | 100.000 | 98.962 | 95.719 | 94.698 |
Heat resistance test result in table 5. plastics (LDPE) system
The above results show that the application coloured light in plastics system of the modified pigment prepared by embodiment 1~2 is partially green, but does not have
Substantially, covering power is partially saturating for green phase in having ink system, also without substantially, intensity slightly declines in ink system.
Application of the experimental example 6 in NC ink
To sequentially adding 28.8g celluloid lacquers, 32.0g absolute ethyl alcohols, 120g beades, 19.2g face in vial
Material, is vibrated 50 minutes after sealing with vibration case, standing is removed after shaking well 15 minutes, obtains dispersion.
True qualities：The above-mentioned dispersions of 12.0g are taken in plastic cup, add 18.0g Letdown Varnish glue heads to stir evenly,
Pigment sample obtained in 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 (evaluating the transparency) after placing 10 minutes.
With disposable dropper just obtained in embodiment 1~2, comparative example pigment sample and standard sample be added dropwise it is 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, be drying and forming-film after placing 10 minutes
(evaluating coloured light and glossiness).
Reduced shade：The above-mentioned dispersions of 1.50g are taken in plastic cup, add 13.5g chalks, stirred evenly with glue head, with disposable
Dropper just obtained in embodiment 1~2, comparative example pigment sample and standard sample be added dropwise a little on the black thick stick art paper of band, 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, is drying and forming-film after placing 10 minutes, uses colour photometer colour examining.
Coloured light and covering power test result in table 6.NC ink systems
Tinctorial strength test result in table 7.NC ink systems
| Title | Gu beautiful Huang 3GNP thoroughly | Comparative example | Embodiment 1 | Embodiment 2 |
| Relative intensity | 100.000 | 99.321 | 98.568 | 95.486 |
The above results show, under N/C systems, obvious partially green, the micro- Huang of pigment sample coloured light obtained in embodiment 1~2 hides
Lid power significantly becomes saturating, and intensity slightly declines.
The present invention has been described in detail above in association with preferred embodiment and exemplary example.But need statement
It is that these specific embodiments are only, to illustrative explanations of the invention, not constitute 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 modification, 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 (15)
1. a kind of yellow pigment composition, it is characterised in that it contains at least one compound and pigment yellow as shown in formula (I)
93,
In formula (I) compound, X, Y are selected from the group as shown in formula (II) or formula (III),
And X, Y are the group as shown in formula (II) when different.
2. composition according to claim 1, it is characterised in that
The compound that formula (I) is as follows：
3. composition according to claim 1 and 2, wherein,
Pigment yellow 93 can be added additionally, it is also possible to acquisition is synthesized together with compound shown in formula (I).
4. a kind of method for preparing the composition as described in one of claims 1 to 3, it is characterised in that
Compound as shown in formula (IV) carries out condensation reaction with rosin amine and 3- methyl -2- chloroanilines, obtains formula (I) shownization
The composition of compound and pigment yellow 93,
Optionally add pigment yellow 93.
5. method according to claim 4, it is characterised in that the method is comprised the following steps：
Step 1, the compound as shown in formula (IV) is dissolved in solvent,
Step 2, rosin amine and 3- methyl -2- chloroanilines are added thereto to, the lower insulation reaction of heating,
Step 3, reaction are lowered the temperature after terminating, filtering, obtain the composition of compound shown in formula (I) and pigment yellow 93.
6. method according to claim 5, it is characterised in that
In step 2, the reaction is condensation reaction.
7. method according to claim 6, it is characterised in that in step 2, the reaction is carried out at 100~200 DEG C
0.5~10h.
8. method according to claim 7, it is characterised in that in step 2, the reaction carries out 1 at 120~180 DEG C
~6h.
9. method according to claim 8, it is characterised in that in step 2, the reaction carries out 2 at 140~160 DEG C
~4h.
10. according to the method that one of claim 4 to 9 is described, it is characterised in that
The mole of the rosin amine is the 2~60% of 3- methyl -2- chloroaniline moles.
11. methods according to claim 10, it is characterised in that the mole of the rosin amine is 3- methyl -2- chlorobenzenes
The 4~40% of amine mole.
12. methods according to claim 11, it is characterised in that the mole of the rosin amine is 3- methyl -2- chlorobenzenes
The 5~20% of amine mole.
13. method according to claim 11 or 12, it is characterised in that
The solvent be halogeno-benzene or alkylbenzene, and/or
Rosin amine is first added, 3- methyl -2- chloroanilines are added.
14. methods according to claim 13, it is characterised in that the solvent is dichloro-benzenes, trichloro-benzenes, dimethylbenzene or three
Toluene.
15. according to one of claims 1 to 3 composition or the group according to obtained in one of claim 4 to 14 methods described
The purposes of compound, uses 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 CN201610130721.3A patent/CN105778564B/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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