CN107227044B - Synergist, pigment composition containing same and color paste - Google Patents
Synergist, pigment composition containing same and color paste Download PDFInfo
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- CN107227044B CN107227044B CN201710165148.4A CN201710165148A CN107227044B CN 107227044 B CN107227044 B CN 107227044B CN 201710165148 A CN201710165148 A CN 201710165148A CN 107227044 B CN107227044 B CN 107227044B
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- 239000000049 pigment Substances 0.000 title claims abstract description 62
- 239000000203 mixture Substances 0.000 title claims abstract description 31
- 239000000126 substance Substances 0.000 claims abstract description 105
- 150000001875 compounds Chemical class 0.000 claims abstract description 82
- 239000012860 organic pigment Substances 0.000 claims abstract description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 15
- 239000002270 dispersing agent Substances 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
- 229910006069 SO3H Inorganic materials 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 10
- -1 Morpholinyl Chemical group 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000004056 anthraquinones Chemical class 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 7
- 230000003389 potentiating effect Effects 0.000 claims 7
- 239000003623 enhancer Substances 0.000 claims 1
- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical compound C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 claims 1
- 230000000052 comparative effect Effects 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000007787 solid Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 239000006185 dispersion Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000012265 solid product Substances 0.000 description 8
- UBZVRROHBDDCQY-UHFFFAOYSA-N 20749-68-2 Chemical compound C1=CC(N2C(=O)C3=C(C(=C(Cl)C(Cl)=C3C2=N2)Cl)Cl)=C3C2=CC=CC3=C1 UBZVRROHBDDCQY-UHFFFAOYSA-N 0.000 description 7
- 238000006277 sulfonation reaction Methods 0.000 description 7
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 238000004040 coloring Methods 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000000976 ink Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229920002120 photoresistant polymer Polymers 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- NIDFGXDXQKPZMA-UHFFFAOYSA-N 14h-benz[4,5]isoquino[2,1-a]perimidin-14-one Chemical compound C1=CC(N2C(=O)C=3C4=C(C2=N2)C=CC=C4C=CC=3)=C3C2=CC=CC3=C1 NIDFGXDXQKPZMA-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- 235000019646 color tone Nutrition 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000007689 inspection Methods 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 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 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- OURXRFYZEOUCRM-UHFFFAOYSA-N 4-hydroxymorpholine Chemical compound ON1CCOCC1 OURXRFYZEOUCRM-UHFFFAOYSA-N 0.000 description 1
- 241001561902 Chaetodon citrinellus Species 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical group [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000002356 laser light scattering Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000001634 microspectroscopy Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- SWVGZFQJXVPIKM-UHFFFAOYSA-N n,n-bis(methylamino)propan-1-amine Chemical compound CCCN(NC)NC SWVGZFQJXVPIKM-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 229940035289 tobi Drugs 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000004383 yellowing 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
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/008—Preparations of disperse dyes or solvent 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
- 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
- C09B67/0084—Dispersions of dyes
- C09B67/0085—Non common dispersing agents
-
- 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
- C09D17/00—Pigment pastes, e.g. for mixing in paints
Abstract
The present invention provides a synergist comprising at least one compound represented by chemical formula 1: [ chemical formula 1]
In the chemical formula 1
m1And m2The definitions of (A) and (B) are as described in the specification and claims. The invention also provides a pigment composition and a color paste containing the synergist. The synergist is suitable for being combined with red organic pigment, so that the pigment composition or color paste prepared subsequently has good dispersibility and stability.
Description
Technical Field
The present invention relates to a synergist (synergist), a pigment composition containing the same, and a color paste, and more particularly, to a synergist suitable for use in combination with a red organic pigment, and a pigment composition containing the same.
Background
Organic pigments are widely used in the fields of inks, paints, plastics coloring, etc., and in recent years, in the fields of color filters, inks for inkjet, etc., and therefore, organic pigments are more strictly required to have properties such as high transparency, high contrast, good dispersibility, etc.
In order to improve color reproducibility and brightness, it is generally desirable that a colored layer formed of colored patterns of three primary colors of red, green, and blue in a color filter have high density and good light transmittance. However, a coloring composition containing an organic pigment at a high concentration must be used for a colored layer at a high concentration, and when the content of the organic pigment is increased, the content of other components of the coloring composition needs to be relatively reduced, which leads to problems that the dispersion stability of the organic pigment is not good and the coloring composition cannot be stably stored, and on the contrary, the light transmittance of the colored layer is decreased. Therefore, the dispersion stability of organic pigments is the first improvement to increase the light transmittance.
Conventionally, there have been known methods of improving the dispersion stability of an organic pigment, such as modifying a pigment and using a pigment dispersion auxiliary (also called a synergist). Many documents and patents have proposed pigment dispersion aids for use with red organic pigments, for example TW I447177 discloses a pigment dispersion photoresist composition for a color filter, containing a pigment dispersion aid represented by the following formula (I) or (II):
formula (I)
Formula (II)
In the formulae (I) and (II), M0Represents H, Na, K, NH4Or NR11R12R13R14，R11、R12、R13And R14Are the same or different and each represents C which may be substituted by other substituents1～C10Saturated or unsaturated aliphatic hydrocarbon group, or C which may be substituted with other substituent6～C10An aromatic hydrocarbon group; m is0Represents an integer of 1 or more. The aforementioned pigment dispersion auxiliary is mainly used in combination with a red color pigment (e.g., c.i. pigment red 2). However, in practical use, the pigment dispersion auxiliary agents represented by the above formulas (I) and (II) and the c.i. pigment red 2 with which they are matched may crack or sublimate during the photoresist baking process due to poor heat resistance, and may cause the color tone of the photoresist to be yellowish, and thus the brightness to be reduced.
As is apparent from the above description, there is a demand for a pigment dispersion aid (synergist) which is used in combination with a red coloring pigment and which enables a pigment composition to be obtained subsequently and which has good dispersibility and stability, does not cause a color shift to yellow, and can maintain brightness.
Disclosure of Invention
It is therefore an object of the present invention to provide a synergist which is suitable for use in combination with red organic pigments.
Thus, the potentiator of the present invention comprises at least one compound represented by chemical formula 1:
[ chemical formula 1]
Wherein the content of the first and second substances,
to represent
Or
X1、X2、X3And X4Are identical or different and each represents hydrogen, a halogen atom, an alkyl group or an acyl group, with the proviso that X1、X2、X3And X4Not both being hydrogen, X5、X6、X7、X8、X9And X10Are the same or different and each represents hydrogen, a halogen atom, an alkyl group or an acyl group;
Y1and Y2Are respectively connected to naphthalene ring,
Or the two aforementioned rings, each being different and representing SO3H、[SO3]nM、SO2-(CH2)p-L1、SO2NH-(CH2)q-L2、
SO2N-[(CH2)r-L3][(CH2)s-L4]；
Wherein M represents an n-valent metal;
n represents an integer of 1 to 3;
p, q, r, s each represent an integer of 1 to 8;
L1represents hydrogen, COOH, NR1R2Morpholinyl (morpholinol), N-methylpiperazinyl (N-methylpiperazinyl), piperazinyl (piperazinyl), pyrazolyl (pyrazolyl), imidazolyl (imidazoyl) or piperidinyl (piperazinyl);
L2、L3and L4Each represents COOH, NR1R2Morpholinyl, N-methylpiperazinyl, piperazinyl, pyrazolyl, imidazolyl or piperidinyl;
R1and R2Each represents hydrogen, C1～C8Alkyl, benzyl or C3～C5A cycloalkyl group; and
m1and m2Each represents an integer of 0 to 4, and m1+m2Is an integer of 1 to 4.
Another object of the present invention is to provide a pigment composition having good dispersibility and good stability.
Thus, the pigment composition of the present invention comprises a red organic pigment and the synergist.
It is still another object of the present invention to provide a color paste having good dispersibility and good stability.
The color paste of the present invention contains a red organic pigment, the above-mentioned synergist, a solvent and a dispersant.
The invention has the following effects: by using the synergist with special structural design, the pigment composition containing the synergist has good dispersibility and stability, and meets the requirements of subsequent application. In addition, the pigment composition of the present invention can selectively avoid the phenomenon of color shift to yellow, and the color paste prepared subsequently can be applied to the fields of color filters or ink-jet inks, etc., which are required to present high brightness and high contrast color.
The present invention will be described in detail below:
[ synergists ]
Preferably, m1+m2Is an integer of 1 to 3.
Preferably, p, q, r and s each represent an integer of 2 to 6; more preferably, p, q, r and s each represent an integer of 2 to 4.
Preferably, in the compound represented by chemical formula 1, m2To 0, the structure is as follows:
preferably, in the compound of chemical formula 1,
to represent
The X is1、X2、X3And X4Are identical or different and each represents a hydrogen or halogen atom, with the proviso that X1、X2、X3And X4Not both hydrogen and the structure is shown as follows:
still more preferably, in the compound of chemical formula 1,
to represent
The X is1、X2、X3And X4Each is a chlorine atom, the Y1Represents SO3H、[SO3]nM or SO2NH-(CH2)q-L2，m2Is 0. In one synthetic example of the present invention, X in the chemical formula 11、X2、X3And X4Each is a chlorine atom, the Y1Represents SO3H [ represented by the following chemical formula 1-1, m1Is 1 or 2]. In another synthesis example of the present invention, X in the chemical formula 11、X2、X3And X4Each is a chlorine atom, the Y1Is represented by [ SO3]nM [ represented by the following chemical formula 1-2]. In another synthesis example of the present invention, X in the chemical formula 11、X2、X3And X4Each is a chlorine atom, the Y1Represents SO2NH-(CH2)q-L2[ as shown in the following chemical formulas 1 to 3]。
[ chemical formula 1-1 ]
[ chemical formula 1-2 ]
[ chemical formula 1-3 ]
Preferably, M in the chemical formula 1-2 represents Al, Mg, Ca, Sr or Ba. In one synthesis example of the present invention, M represents Al and n is 3, M1Is 1 or 2.
Preferably, q in the chemical formulas 1 to 3 is 3, and L2Is NR1R2. In one synthetic example of the present invention, L is2Is N (CH)3)2，m1Is 1 or 2.
Preferably, the compound of formula 1 has the structure
[ chemical formulae 1-4 ]
Preferably, in the compound represented by chemical formula 1, the
To represent
The X is5、X6、X7、X8、X9And X10Are the same or different and each represents a hydrogen or halogen atom, and the structure is shown as follows:
still more preferably, the X5、X6、X7、X8、X9And X10Are each a hydrogen atom, the Y1Represents SO3H [ represented by the following chemical formula 1-5, m1Is 1 or 2]：
[ chemical formula 1-5 ]
The synergist comprises one, two or more than two compounds shown in a chemical formula 1. In one embodiment of the present invention, the synergist comprises a compound represented by chemical formula 1 (i.e., the kind of the compound represented by chemical formula 1 is one), the chemical formula 1 being represented by chemical formula 1-1. In another embodiment of the present invention, the synergist comprises a compound represented by chemical formula 1, wherein chemical formula 1 is represented by chemical formula 1-2. In another embodiment of the present invention, the synergist comprises a compound represented by chemical formula 1, wherein chemical formula 1 is represented by chemical formula 1-3. In another embodiment of the present invention, the synergist comprises a compound represented by chemical formula 1, wherein chemical formula 1 is represented by chemical formula 1-5. In another embodiment of the present invention, the synergist comprises two compounds represented by chemical formula 1 (i.e., the kinds of the compounds represented by chemical formula 1 are two), wherein the chemical formula 1 of one compound is represented by chemical formulas 1 to 3, and the chemical formula 1 of the other compound is represented by chemical formulas 1 to 4.
When the synergist contains two or more compounds represented by chemical formula 1, the amount of each compound may be in terms of m1(and/or m)2) The value size and subsequent applications are adjusted. For example, when the synergist comprises a compound P1 represented by chemical formula 1-1, a compound P3 represented by chemical formula 1-3, and a compound P4 represented by chemical formula 1-4, the ratio of P1/(P3+ P4) is in the range of
Preferably, the ratio of P1/(P3+ P4) is in the range of
The preparation of the synergist of the present invention can be carried out according to a general chemical synthesis method, and taking the compound represented by the chemical formula 1-1 as an example, the synergist can be obtained by sulfonating a c.i. solvent red 135[ chemical name is 8,9,10, 11-tetrachloro-12H-phthalimide-12-one (8,9,10, 11-tetrachloro-12H-phthalimide-12-one) represented by the following chemical formula ]:
taking the compound represented by chemical formula 1-2 as an example, it can be obtained by subjecting c.i. solvent red 135 to a sulfonation reaction, followed by a precipitation reaction with a salt containing M. In one embodiment of the invention, the salt containing M is aluminum sulfate.
Taking the compounds of chemical formulas 1-3 and 1-4 as examples, C.I. solvent Red 135 can be first sulfonated and then treated with thionyl chloride (SOCl)2) After formation of the sulfonyl chloride, it is reacted with NH2-(CH2)q-L2Carrying out sulphonation reaction to obtain the product. In one embodiment of the invention, NH2-(CH2)q-L2Is NH2-(CH2)3-N(CH3)2。
Taking the compounds represented by the chemical formulas 1 to 5 as an example, they can be obtained by sulfonating c.i. solvent red 179{ chemical name of 14H-benzo [4,5] isobenzoquinone [2,1-a ] perimidine-14-one (14H-benzoquinone [4,5] isoquino [2,1-a ] perimidin-14-one) }:
[ pigment composition ]
The pigment composition of the present invention comprises a red organic pigment and the at least one synergist.
The amount of the synergist varies according to the composition and amount of the red organic pigment, and preferably ranges from 0.1 to 30 parts by weight based on 100 parts by weight of the red organic pigment.
Preferably, the red organic compoundThe pigment is selected from diketopyrrolopyrroles, anthraquinones, or combinations thereof. Commercially available commercial products of the diketopyrrolopyrrole type pigments are exemplified by, but not limited to, c.i. pigment red 254 (e.g., BASF)
Red S3611 CF), c.i. pigment Red 255, c.i. pigment Red 264, c.i. pigment Red 272, and the like. Commercially available products of the anthraquinone pigments include, but are not limited to, c.i. pigment red 177, c.i. pigment red 83, c.i. pigment red 85, c.i. pigment red 89, c.i. pigment red 168, c.i. pigment red 194, c.i. pigment red 195, and c.i. pigment red 196. The aforementioned various red organic pigments may be used singly or in combination of two or more. In one embodiment of the present invention, the red organic pigment is a combination of c.i. pigment red 254 and c.i. pigment red 177.
Preferably, the pigment composition further comprises a color-adjusting organic pigment, which is different from the red organic pigment and is a pigment of other colors that does not affect the dispersibility, stability, light transmittance and other properties of the pigment composition. Examples of commercially available products of the toning pigment include, but are not limited to, c.i. pigment orange 73, c.i. pigment orange 40, c.i. pigment orange 51, c.i. pigment orange 77, and the like. The aforementioned various color-adjusting organic pigments may be used singly or in combination of two or more.
[ color paste ]
The color paste comprises a red organic pigment, a synergist, a solvent and a dispersant.
The red organic pigment is as described in the above [ pigment composition ] for the "red organic pigment", and the synergist is as described in the above [ synergist ]. Examples of such solvents include, but are not limited to, propylene glycol methyl ether acetate, propylene glycol methyl ether, cyclohexanone, n-butanol, and the like. The aforementioned various solvents may be used singly or in combination of two or more. In one embodiment of the invention, the solvent is propylene glycol methyl ether acetate and n-butanol.
Examples of such dispersants include, but are not limited to, LP-N-21324 and LP-N-21116, LP-N-21208, LP-N-6919, Disperbyk-2000, Disperbyk-2001, manufactured by BYK Chemie; EFKA-4300, EFKA-4330, EFKA-4340, EFKA-4400, EFKA-4401, EFKA-4402, EFKA-4046 and EFKA-4060 manufactured by BASF corporation; ajisper PB821, PB822, PB880 manufactured by Ajinomoto corporation; solsperse20000, Solsperse 24000, Solsperse 27000, Solsperse 28000, etc., manufactured by Lubrizol corporation. The foregoing various dispersants may be used singly or in combination of two or more. In one embodiment of the present invention, the dispersants LP-N-21324 and LP-N-21116 are available from BYKChemie, Inc.
The color paste may optionally further comprise a dispersing resin, a tinting organic pigment, or a combination of the two. Such as, but not limited to, polyacrylic (polyacrylate) resin, cardo (cardo) resin, polyester (polyester) resin, polyimide (polyimide) resin, and the like. The dispersion resins described above may be used singly or in combination of two or more. The tinting organic pigments are as described above in [ pigment composition ] for "tinting organic pigments".
In the color paste, the dosage of the red organic pigment, the synergist, the solvent and the dispersant can be adjusted according to actual needs. Preferably, the amount of the red organic pigment is 5-20 wt%, the amount of the synergist is 0.1-4 wt%, the amount of the dispersant is 5-15 wt%, and the amount of the solvent is 70-85 wt%, based on 100 wt% of the total color paste. More preferably, the amount of the red organic pigment is 10-18 wt%, the amount of the synergist is 0.1-2 wt%, the amount of the dispersant is 7-10 wt%, and the amount of the solvent is 75-80 wt%.
Detailed Description
The invention will be further described in the following examples, but it should be understood that these examples are for illustrative purposes only and should not be construed as limiting the practice of the invention.
< example >
EXAMPLE 1 preparation of potentiator comprising Compound represented by chemical formula 1-1
480 parts of (by weight) SO 20 percent3The fuming sulfuric acid is placed in a round bottom bottle, a magnet is placed in the round bottom bottle for stirring, and then the round bottom bottle is placed in a water bath kettle. 70.5 parts of c.i. solvent red 135 are taken and slowly added to the above-mentioned round-bottomed flask and the temperature of the water bath is allowed to fall below 40 ℃. Forming a reaction solution after the C.I. solvent red 135 in the round-bottomed bottle is completely dissolved, and reacting the reaction solution at room temperature for 1 hour. After 0.5mL of the reaction solution was extracted and added to 10mL of water to confirm that the entire amount of the reaction product was soluble in water, 2000 parts of butanone was added to the beaker and the beaker was placed in an ice bath, the reaction solution was slowly added to the beaker to form a mixture, and the temperature of the reaction solution in the beaker was allowed to fall below 40 ℃. The mixture was filtered to obtain a crude product, which was then repeatedly washed with butanone. After each washing, the washing liquid was collected, and 1 part of the washing liquid was mixed with 4 parts of water to obtain a test liquid, which was subjected to conductivity test using a conductivity meter (purchased from EUTECH, inc., model number COND 6 +). And finishing the cleaning step until the conductivity of the test solution is less than 200 mu S/cm, drying the cleaned crude product in a 60 ℃ oven, crushing the dried crude product, and baking the crushed crude product in a 150 ℃ oven for 1 hour to obtain 99.6 parts of dark red solid product.
The dark red solid product described above was subjected to the following analysis:
1. sulfonation value per molecule: measured by an elemental analyzer (SGS, Taiwan inspection science and technology Co., Ltd.), to determine whether sulfur atom occupies the molecule
I.e. a sulfonation value of 1.8 per molecule.
IR spectral analysis: the dark red solid product and KBr are placed in an agate mortar and ground into powder, and then the powder is taken out to prepare salt tablets. The salt tablets were placed in an infrared spectrometer (model number Spectrum 100 from Perkin Elmer) for testing and IR spectra were obtained. Comparing the IR spectrum with that of C.I. solvent Red 135, the dark red solid product was found at 1030cm-1Has a strong S ═ O signal, and is based on the above elemental analysis at point 1 and sulfonation per moleculeThe test of the value confirmed that the dark red solid product was the compound (m) of the formula 1-11Is 1) and the compound (m) of the formula 1-11Is 2).
EXAMPLE 2 preparation of potentiator comprising Compound represented by chemical formula 1-2
3.0 parts by weight of the product of example 1 were taken, 85.9 parts by weight of 0.1722N KOH aqueous solution was added thereto and stirred well, and thereafter 1.52 parts by weight of Al was slowly added2(SO4)3·16H2And O, obtaining a reaction solution. After the reaction solution was allowed to stand overnight, a solid was observed to be precipitated. The reaction solution was filtered, washed with water several times, and dried to obtain 2.54 parts by weight of red powder.
When analyzed according to the IR spectroscopy procedure of example 1, the sulfonate signal was observed at 1036cm from the obtained IR spectrum-1From this, it was confirmed that the red powder was the compound represented by chemical formula 1-2 (M ═ Al, n ═ 3, M ═ 3)11) and the compound of formula 1-2 (M ═ Al, n ═ 3, M12). The sulfonation number per molecule was the same as in example 1 and was 1.8.
EXAMPLE 3 preparation of potentiator comprising Compound represented by chemical formula 1-3 and Compound represented by chemical formula 1-4
A reaction solution was obtained by adding 10.0 parts by weight of the product obtained in example 1 to a double-necked flask, and adding 30.0 parts by weight of thionyl chloride and 60 parts by weight of dimethylformamide thereto. The reaction solution was heated to 90 ℃ and reacted for 5 hours. After the reaction solution was cooled to room temperature, the reaction solution was dropped into ice water, and the solid was collected and washed with water 3 times. The solid was placed in 200 parts by weight of ice water (ice/water-1/1). Under an ice bath, 16.0 parts by weight of N, N-dimethylaminopropylamine was slowly added to the solid, and stirred for 5 minutes to obtain a mixed solution. The temperature of the mixture was raised to 90 ℃ and reacted for 1.5 hours. And (3) carrying out ice bath on the mixed solution, adjusting the pH value to 1-2 by using concentrated sulfuric acid, precipitating a solid, washing the solid by using water until the conductivity of the water filtrate is less than 200 mu S/cm, and drying to obtain 10.6 parts by weight of brown solid.
Analysis was carried out according to the IR Spectroscopy procedure of example 1, from which sulphur was observedAmide signal at 1027cm-1And sulfonate signal at 1036cm-1From this, it was confirmed that the brown solid contained the compound represented by chemical formula 1-3 (q ═ 3, L)2＝N(CH3)2，m11), the compound represented by the chemical formula 1-3 (q ═ 3, L2＝N(CH3)2，m12) and the compounds of formulae 1 to 4 (q ═ 3, L)2＝N(CH3)2，m11 and m2＝1)。
The above brown solid was subjected to the following analysis:
the compound represented by chemical formula 1-3 (q ═ 3, L) was obtained by measuring 8.29% of sulfur atoms and 10.58% of nitrogen atoms with an elemental analyzer (SGS, taiwan inspection science and technology ltd), and calculating the elemental analysis data in table 1 below and the three equations in table 1 below (q ═ 3, L)2＝N(CH3)2，m162% of ═ 2), and the compound represented by the chemical formula 1-4 (q ═ 3, L)2＝N(CH3)2，m11 and m218% of ═ 1), and the compound represented by chemical formula 1-3 (q ═ 3, L)2＝N(CH3)2，m11) with a sulphonation value of 0.18 per molecule and a sulphonamide value of 1.62 per molecule.
[ TABLE 1]
11.41a +8.59b +9.79c ═ 10.58, 8.71a +9.83b +5.60c ═ 8.29, and a + b + c ═ 1[ a denotes a compound represented by formula 1-3 (m +8.59b + 1.3)12) the content percentage; b is a compound (m) of the formula 1-411 and m21) the content percentage; c is a compound (m) of the formula 1-311) in percentage by weight]。
EXAMPLE 4 preparation of potentiator comprising Compound represented by chemical formula 1-5
The procedure and conditions were as described in example 1 except that the C.I. solvent Red 135 used in example 1 was changed to C.I. solvent Red 179, thereby obtaining113.1 parts of a red solid product are obtained. The red solid product is the compound (m) of the formula 1-511) and the compound represented by the chemical formula 1-5 (m)1＝2)。
The red solid product described above was subjected to the following analysis:
sulfonation value per molecule: the content of sulfur atoms in the molecule was 13.0%, that is, the sulfonation value per molecule was 1.9, as measured by an elemental analyzer (entrusted GHS).
Comparative example 1 Compound represented by the following chemical formula 2
[ chemical formula 2]
The compound of comparative example 1 was purchased from Daiwa, japan, and was model number 254 SR.
[ application examples 1 to 4] and [ comparative application examples 1 and 2] preparation of color pastes
Color pastes of application examples 1 to 3 and comparative application examples 1 and 2 were co-prepared: red organic pigments (manufactured by BASF Corp.) were used in the following proportions in Table 2
Red S3611 CF), synergist, solvent (propylene glycol monomethyl ether acetate and N-butanol) and dispersant (LP-N-21324 and LP-N-21116) were added to 0.3mm zirconium balls, 4 times the weight of the color paste, at room temperature, placed in a PP grinding pot of appropriate size, mixed for 1 hour with a Red devil equal equipment mixer (model 1400-OH), filtered to remove the zirconium balls, and the color paste was obtained.
Application example 1 used the synergist of example 1 (including the compound represented by chemical formula 1-1), application example 2 used the synergist of example 2 (including the compound represented by chemical formula 1-2), application example 3 used the synergist of example 3 (including the compound represented by chemical formula 1-3 and the compound represented by chemical formula 1-4), application example 4 used the synergist of example 4 (including the compound represented by chemical formula 1-5), comparative application example 1 used no synergist, and comparative application example 2 used the synergist of comparative example 1.
3. And (3) testing:
the color pastes of application examples 1 to 4 and comparative application examples 1 and 2 were subjected to the following tests, respectively, the results of which are collated in table 3:
(1) theoretical solid content and actual solid content (wt%): the theoretical solids content is obtained by summing up the amounts of red organic pigment, synergist and dispersant in table 1. Placing 1 g of color paste on an aluminum dish to obtain a test sample, and weighing the test sample to obtain the weight before baking; then, the test sample was placed on a heating plate at 150 ℃ for 60 minutes and weighed to obtain the baked weight.
(2) Particle size (nm): the color paste was diluted 500-fold with propylene glycol monomethyl ether acetate, and then the average particle diameter (Zave) was measured with a dynamic laser light scattering instrument (model No. Zetasizer 1000HSA, manufactured by DKSH).
(3) Original viscosity (cp): the viscosity of the color paste was measured at 25 ℃ and a spindle rotation speed of 60rpm by using a viscometer (model TVE-20L manufactured by Toyobo industries, Ltd.).
(4) Viscosity and rate of change of viscosity after 1 week at room temperature: the color paste is placed at room temperature (23-28 ℃) for 1 week, and then the viscosity of the color paste is measured by a viscometer. Recalculation
(5) C.i.e. chromaticity coordinate diagram: the color paste was coated on a glass substrate having a thickness of 0.7mm using a spin coater (model MSC-450, manufactured by TOBI Co., Ltd.). Thereafter, the mixture was dried on a hot plate at 100 ℃ for 3 minutes. Then, c.i.e. chromaticity coordinates (Y, x, Y) were obtained by measuring with a microspectrometry device (model LCF-6000, manufactured by tsukamur electronics corporation, model MCPD-2000).
[ TABLE 2]
[ TABLE 3]
From the results of tables 2 and 3, it can be seen that when application examples 1 to 4 are compared with comparative application examples 1 and 2, the particle diameters and viscosity change rates of application examples 1 to 4 are lower than those of comparative application example 1 and almost identical to those of comparative application example 2, and it is shown that the addition of the synergist of the present invention can indeed improve the dispersibility of the red organic pigment and the stability of the color paste, and can also meet the standard of the commercially available synergist (e.g., comparative application example 2). Compared with the comparative application example 1, the viscosity stability of the composite material can be improved by adding the application examples 1 to 4 of the chemical formulas 1 to 5. Although the viscosity stability was improved as compared with comparative application example 2, the luminance (Y value) was more decreased than that of comparative application example 1 in which no synergist was used. Comparing the comparative application example 2 with the application examples 1 to 4 to which the chemical formulas 1 to 5 were added, it can be found that the luminance (Y value) of the application examples 1 to 4 is excellent.
Comparing application examples 1 and 2 with comparative application example 2, it can be found that the viscosity change rate of application examples 1 and 2 is lower than that of comparative application example 2, and the synergist of the present invention (especially the synergist containing the compound represented by chemical formula 1-1 or 1-2) can make the stability of the color paste prepared later better than that of the commercial synergist.
[ application examples 5 to 8] and [ comparative application examples 3 and 4] preparation of color pastes
Color pastes of application examples 5 to 8 were prepared according to the procedure of application examples 1 to 3, except that the red organic pigment was replaced with c.i. pigment red 177 (model No. SR4C) manufactured by nintendo Chemicals (Cinic Chemicals (Shanghai) co., Ltd), the dispersant was used LP-N-21116, and the amounts of some components were changed.
The color pastes of comparative application examples 3 and 4 were prepared according to the procedure of comparative application examples 1 and 2, except that the red organic pigment was replaced with c.i. pigment red 177 (model SR4C) manufactured by nintendo Chemicals (Cinic Chemicals (Shanghai) co., Ltd), the dispersant was LP-N-21116, and the amounts of some components were changed according to table 4.
The color pastes prepared in application examples 5 to 8 and comparative application examples 3 and 4 were subjected to the same test as in application example 1, respectively, and the results are summarized in table 5.
[ TABLE 4]
[ TABLE 5]
From the results of tables 4 and 5, it is understood that when application examples 5 to 8 are compared with comparative application example 3, it is found that the viscosity change rates of application examples 5 to 8 are all lower than that of comparative application example 3, and it is shown that the dispersibility of the red organic pigment and the stability of the color paste can be improved with certainty by adding the synergist of the present invention. The brightness (Y value) of application examples 5 to 8 exhibited better or equal compared to comparative application example 3 where no synergist was used or comparative application example 4 where 254SR was used.
Comparing application example 5 with comparative application example 4, it can be seen that the particle size and viscosity change rate of application example 5 are lower than those of comparative application example 4, and it is shown that the synergist of the present invention (especially the synergist comprising the compound represented by chemical formula 1-1) can make the dispersibility and stability of the subsequently prepared color paste better than those of the commercially available synergist.
Application examples 9 to 11 preparation of color pastes
Color pastes of application examples 9 to 11 were prepared according to the procedure of application examples 1 to 3, except that the synergist was replaced with a combination of the synergist of example 1 (comprising the compound of chemical formula 1-1) and the synergist of example 3 (comprising the compound of chemical formula 1-3 and the compound of chemical formula 1-4). The color pastes prepared in application examples 9 to 11 were subjected to the same tests as in application example 1, and the results are shown in Table 6.
[ TABLE 6 ]
From the results in table 6, it can be seen that when application examples 9 to 11 were compared with examples 1 to 4 and comparative application examples 1 and 2 in table 1, the viscosity change rate of application examples 9 to 11 was 0% or less, which indicates that the addition of a synergist containing two or more compounds (particularly, a combination of a compound represented by chemical formula 1-1, a compound represented by chemical formula 1-3, and a compound represented by chemical formula 1-4) more improved the stability of the color paste. Comparing application example 2 with application examples 9 to 11, it was also found that the luminance (Y value) of application examples 9 to 11 performed better.
[ application examples 12 to 14] preparation of color pastes
Color pastes of application examples 12 to 14 were prepared according to the procedure of application examples 9 to 11, except that the red organic pigment was replaced with c.i. pigment red 177 (model No. SR4C) manufactured by nintendo Chemicals (Cinic Chemicals (Shanghai) co., Ltd), the dispersant was used LP-N-21116, and the amounts of some of the components were changed. The color pastes prepared in application examples 12 to 14 were subjected to the same tests as in application example 1, and the results are shown in tables 7 and 8.
[ TABLE 7 ]
[ TABLE 8]
As is clear from the results of tables 7 and 8, when application examples 12 to 14 were compared with examples 5 to 8 and comparative application examples 3 and 4 in table 2, it was found that the viscosity change rate of application examples 12 to 14 was 0% or less and that the addition of a synergist containing two or more compounds (particularly, a combination of a compound represented by chemical formula 1-1, a compound represented by chemical formula 1-3, and a compound represented by chemical formula 1-4) more improved the stability of the color paste. The brightness (Y value) of application examples 12 to 14 performed better or equal compared to comparative application example 3 where no synergist was used or comparative application example 4 where 254SR was used.
In conclusion, the synergist with a special structural design is used, so that the pigment composition containing the synergist has good dispersibility and stability; in addition, the pigment composition of the present invention can selectively further avoid the occurrence of color shift yellowing phenomenon to maintain good brightness, and simultaneously, the color paste prepared subsequently is more suitable for being applied in the fields of color filters or inkjet inks, etc. which are required to present high contrast color tones, so the object of the present invention can be achieved.
However, the above description is only an example of the present invention, and the scope of the present invention should not be limited thereby, and all simple equivalent changes and modifications made according to the claims and the contents of the patent specification are still included in the scope of the present invention.
Claims (11)
1. A potentiator comprising at least one compound represented by chemical formula 1:
[ chemical formula 1]
Wherein the content of the first and second substances,
to represent
X1、X2、X3And X4Are the same or different and each represents hydrogen, a halogen atom, an alkyl group or an acyl group, provided thatIs X1、X2、X3And X4Not both may be hydrogen;
Y1and Y2Are respectively connected to naphthalene ring,
Or the two aforementioned rings, each being different and representing SO3H、[SO3]nM、SO2-(CH2)p-L1、SO2NH-(CH2)q-L2、SO2N-[(CH2)r-L3][(CH2)s-L4]；
Wherein M represents an n-valent metal;
n represents an integer of 1 to 3;
p, q, r, s each represent an integer of 1 to 8;
L1represents COOH, NR1R2Morpholinyl, N-methylpiperazinyl, piperazinyl, pyrazolyl, imidazolyl or piperidinyl;
L2、L3and L4Each represents COOH, NR1R2Morpholinyl, N-methylpiperazinyl, piperazinyl, pyrazolyl, imidazolyl or piperidinyl;
R1and R2Each represents hydrogen, C1～C8Alkyl, benzyl or C3～C5A cycloalkyl group; and
m1and m2Each represents an integer of 0 to 4, and m1+m2Is an integer of 1 to 4.
2. The potentiating agent as defined in claim 1, wherein the compound of formula 1 is a compound of formula 1
To represent
The X is1、X2、X3And X4Are identical or different and each represents a hydrogen or halogen atom, with the proviso that X1、X2、X3And X4Not both may be hydrogen.
3. The potentiating agent as defined in claim 2, wherein, in the compound of formula 1, the X is1、X2、X3And X4Each is a chlorine atom, the Y1Represents SO3H、[SO3]nM or SO2NH-(CH2)q-L2，m2Is 0.
4. The potentiating agent as defined in claim 3, wherein in the compound of formula 1, the Y is1Represents SO2NH-(CH2)q-L2Q is 3, and L2Is NR1R2。
5. The potentiating agent as defined in claim 1, wherein said kind of compound represented by the chemical formula 1 is one, said compound represented by the chemical formula 1 being
To represent
The X is1、X2、X3And X4Each is a chlorine atom, the Y1Represents SO3H，m2Is 0.
6. The potentiating agent as defined in claim 1, wherein said kind of compound represented by the chemical formula 1 is one, said compound represented by the chemical formula 1 being
To represent
The X is1、X2、X3And X4Each is a chlorine atom, the Y1Is represented by [ SO3]nM。
7. The potentiating agent as defined in claim 1, wherein said kind of compound represented by the chemical formula 1 is one, said compound represented by the chemical formula 1 being
To represent
The X is1、X2、X3And X4Each is a chlorine atom, the Y1Represents SO2NH-(CH2)q-L2。
8. The potentiating agent as defined in claim 1, wherein said compounds of the formula 1 are of three kinds, said compound of the formula 1 being
To represent
In one of the compounds of the formula X1、X2、X3And X4Each is a chlorine atom, the Y1Represents SO3H；
The X in the chemical formula 1 of another compound1、X2、X3And X4Each is a chlorine atom, the Y1Represents SO2NH-(CH2)q-L2；
The X in the chemical formula 1 of another compound1、X2、X3And X4Each is a chlorine atom, the Y1Represents SO3H, and Y2Represents SO2NH-(CH2)q-L2And m is1And m2Is not 0.
9. A pigment composition comprising:
a red organic pigment; and
the enhancer of any one of claims 1 to 8,
wherein the amount of the synergist is 0.1 to 30 parts by weight based on 100 parts by weight of the red organic pigment.
10. The pigment composition of claim 9, wherein the red organic pigment is selected from a pyrrolopyrrole pigment, an anthraquinone pigment, or a combination of the foregoing.
11. A color paste comprising:
the pigment composition of claim 9;
a solvent; and
a dispersant.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5530130A (en) * | 1993-08-19 | 1996-06-25 | Bayer Aktiengesellschaft | Phthaloperinone dyestuffs |
| CN1488018A (en) * | 2001-01-22 | 2004-04-07 | �����ﰲ�ز���(Bvi)����˾ | Use of pigment dyes for dispersion dyeing from aqueous media |
| CN102421855A (en) * | 2009-04-22 | 2012-04-18 | 德司达染料德国有限责任公司 | Dyes for polymer coloration, their preparation and their use |
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| JPS5857463B2 (en) * | 1975-12-16 | 1983-12-20 | 三菱化学株式会社 | Suiyouseisenriyounoseizohouhou |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5530130A (en) * | 1993-08-19 | 1996-06-25 | Bayer Aktiengesellschaft | Phthaloperinone dyestuffs |
| CN1488018A (en) * | 2001-01-22 | 2004-04-07 | �����ﰲ�ز���(Bvi)����˾ | Use of pigment dyes for dispersion dyeing from aqueous media |
| CN102421855A (en) * | 2009-04-22 | 2012-04-18 | 德司达染料德国有限责任公司 | Dyes for polymer coloration, their preparation and their use |
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