CN107227044A - Synergist, pigment composition containing same and color paste - Google Patents
Synergist, pigment composition containing same and color paste Download PDFInfo
- Publication number
- CN107227044A CN107227044A CN201710165148.4A CN201710165148A CN107227044A CN 107227044 A CN107227044 A CN 107227044A CN 201710165148 A CN201710165148 A CN 201710165148A CN 107227044 A CN107227044 A CN 107227044A
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- chemical formula
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- synergist
- compound
- pigment
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- 239000000203 mixture Substances 0.000 title claims abstract description 32
- 239000000049 pigment Substances 0.000 title claims abstract description 27
- 239000000126 substance Substances 0.000 claims abstract description 114
- 150000001875 compounds Chemical class 0.000 claims abstract description 80
- 239000001054 red pigment Substances 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 19
- 239000002270 dispersing agent Substances 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 229910006069 SO3H Inorganic materials 0.000 claims description 11
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 11
- -1 NR1R2 Chemical group 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000002757 morpholinyl group Chemical group 0.000 claims description 5
- 125000004193 piperazinyl group Chemical group 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000005936 piperidyl group Chemical group 0.000 claims description 3
- 150000004056 anthraquinones Chemical class 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
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- 150000002790 naphthalenes Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 150000003053 piperidines Chemical class 0.000 claims 1
- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical class C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 claims 1
- 239000012860 organic pigment Substances 0.000 abstract description 14
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000007787 solid Substances 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000006185 dispersion Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000002329 infrared spectrum Methods 0.000 description 7
- 239000012265 solid product Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000012530 fluid Substances 0.000 description 6
- 239000000654 additive Substances 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 238000004140 cleaning Methods 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 239000006071 cream Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 3
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 0 CC=C=Cc1cccc(N(C(CC=CC=CC=CC=C2C=C*)C#[U])C2=N2)c1C2=C Chemical compound CC=C=Cc1cccc(N(C(CC=CC=CC=CC=C2C=C*)C#[U])C2=N2)c1C2=C 0.000 description 2
- 241001561902 Chaetodon citrinellus Species 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical class C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 235000006200 Glycyrrhiza glabra Nutrition 0.000 description 1
- 244000303040 Glycyrrhiza glabra Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 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
- XAIKOVRFTSBNNU-UHFFFAOYSA-N anthracene-9,10-dione Chemical class C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 XAIKOVRFTSBNNU-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 150000004054 benzoquinones Chemical class 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- LPLVUJXQOOQHMX-QWBHMCJMSA-N glycyrrhizinic acid Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@@H]1C([C@H]2[C@]([C@@H]3[C@@]([C@@]4(CC[C@@]5(C)CC[C@@](C)(C[C@H]5C4=CC3=O)C(O)=O)C)(C)CC2)(C)CC1)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O LPLVUJXQOOQHMX-QWBHMCJMSA-N 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000011477 liquorice Nutrition 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000002156 mixing 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
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000003386 piperidinyl group Chemical group 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
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229940035289 tobi Drugs 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229910052726 zirconium Inorganic materials 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 1m1And 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 invention relates to a kind of synergist (synergist), color compositions and color containing it, particularly relate to
A kind of synergist, color compositions and color containing it suitable for being applied in combination with organic red pigment.
Background technology
Organic pigment is also widely used in coloured silk recently in addition to being widely used in the fields such as ink, coating, coloring plastic
The fields such as colo(u)r filter, ink for inking, so, organic pigment more by strictly requirement need to possess high transparency, high-contrast,
The properties such as good dispersion.
By taking colored filter as an example, in order to improve color reprodubility and brightness, it will usually it is desirable that in colored filter, by
The dyed layer that the colored pattern of Red Green Blue is constituted can possess high concentration and good light transmittance.However, high
The dyed layer of concentration must use the coloured composition containing high concentration organic pigment, when organic pigment content is improved, coloring
The content of the other compositions of composition is accomplished by relatively reducing, so again can derive organic pigment dispersion stability it is not good and
Colour cell compound can not storage-stable the problem of, instead result in dyed layer light transmittance decline.Therefore, organic pigment is scattered steady
It is qualitative to turn into the primary improving countermeasure for improving light transmittance.
The scheme of the existing known dispersion stabilization for improving organic pigment, for example, modified to pigment, using pigment
Disperse additive (also known as synergist) etc..Most literature and patent have pointed out with organic red pigment and the scattered auxiliary of pigment
Agent, such as TW I447177 disclose a kind of colored filter and disperse Photoresisting agent composition with pigment, contain lower formula (I) or (II) institute
The pigment disperse additive shown：
Formula (I)
Formula (II)
In formula (I) and (II), M0Represent H, Na, K, NH4Or NR11R12R13R14, R11、R12、R13And R14To be identical or different
And each represent the C that can be replaced through other substituents1~C10Saturation or unsaturated fatty hydrocarbons base can be through other substituents
The C replaced6~C10Aromatic hydrocarbyl；m0The integer of expression more than 1.Foregoing pigment disperse additive be mainly used for it is red
Chromatic colorant pigment (such as C.I. paratoneres 2) is used in combination.However, when actual use, the face shown in above-mentioned formula (I) and formula (II)
The C.I. paratoneres 2 that material disperse additive is arranged in pairs or groups with it may be produced because heat resistance is not good in photoresistance plus baking journey
Cracking distils, and more likely allows the tone of photoresistance partially yellow, and cause luminance-reduction.
From described above, with red tinting color and using, while follow-up obtained color compositions can be allowed to possess good
Dispersiveness, stability are got well, will not occur the partially yellow phenomenon of tone and the pigment disperse additive (synergist) of brightness can be maintained still to have
Continue the demand researched and developed.
The content of the invention
Therefore, the purpose of the present invention, that is, providing a kind of synergist suitable for being applied in combination with organic red pigment.
Then, synergist of the present invention, includes at least one compound as shown in chemical formula 1：
【Chemical formula 1】
Wherein,RepresentOrX1、X2、X3And X4To be identical or different and each
From hydrogen, halogen atom, alkyl or acyl group is represented, its condition is X1、X2、X3And X4It is not simultaneously hydrogen, X5、X6、X7、X8、X9And
X10To be identical or different and each represent hydrogen, halogen atom, alkyl or acyl group；
Y1And Y2Be respectively connecting to naphthalene nucleus,Or foregoing two ring, it is respectively different and expression SO3H、[SO3]nM、SO2-
(CH2)p-L1、SO2NH-(CH2)q-L2、
SO2N-[(CH2)r-L3][(CH2)s-L4]；
Wherein, M represents n valency metals；
N represents 1 to 3 integer；
P, q, r, s each represent 1 to 8 integer；
L1Represent hydrogen, COOH, NR1R2, morpholinyl (morpholinyl), N methyl piperazine base (N-
Methylpiperazinyl), piperazinyl (piperazinyl), pyrazolyl (pyrazolyl), imidazole radicals (imidazolyl) or
Piperidyl (piperidinyl)；
L2、L3And L4Each represent COOH, NR1R2, morpholinyl, N methyl piperazine base, piperazinyl, pyrazolyl, imidazole radicals or
Piperidyl；
R1And R2Each represent hydrogen, C1~C8Alkyl, benzyl or C3~C5Cycloalkyl；And
m1And m2The integer of expression 0 to 4, and m respectively1+m2For 1 to 4 integer.
Another object of the present invention, i.e., provide it is a kind of possess good dispersion, good stability color compositions.
Then, color compositions of the invention, include organic red pigment and the synergist.
The present invention again another object, i.e., offer it is a kind of possess good dispersion, good stability color.
Then, color of the invention, includes organic red pigment, above-mentioned synergist, solvent and dispersant.
Effect of the present invention is：By using the synergist designed with special construction, it is able to allow and contains the synergist
Color compositions possess good dispersiveness and stability, meet the demand of subsequent applications.In addition, it will be further appreciated that,
Color compositions of the present invention selectively further avoid the generation of the partially yellow phenomenon of tone, can more allow follow-up obtained color simultaneously
Cream is suitably applied in requirement and presented in the field such as high brightness and the colored filter or jetted ink of high contrast hue.
It will be described in detail below with regard to present invention：
[synergist]
It is preferred that m1+m2For 1 to 3 integer.
It is preferred that p, q, r and s each represent 2 to 6 integer；More preferably, p, q, r and s each represent 2 to 4 integer.
It is preferred that in the compound shown in the chemical formula 1, m2For 0, structure is as follows：
It is preferred that in the compound shown in the chemical formula 1,RepresentThe X1、X2、X3And X4For
Identical or different and each represent hydrogen or halogen atom, its condition is X1、X2、X3And X4It is not simultaneously hydrogen, the following institute of structure
Show：
More preferably, the m2For 0, structure is as follows：
Again more preferably, in the compound shown in the chemical formula 1,RepresentThe X1、X2、X3And X4
Respectively chlorine atom, the Y1Represent SO3H、[SO3]nM or SO2NH-(CH2)q-L2, m2For 0., should in the synthesis example of the present invention
X in chemical formula 11、X2、X3And X4Respectively chlorine atom, the Y1Represent SO3H [as shown in formula 1 below -1, m1For 1 or 2].
In another synthesis example of the present invention, the X in the chemical formula 11、X2、X3And X4Respectively chlorine atom, the Y1Represent [SO3]nM is [such as
Shown in formula 1 below -2].In another synthesis example of the present invention, the X in the chemical formula 11、X2、X3And X4Respectively chlorine is former
Son, the Y1Represent SO2NH-(CH2)q-L2[as shown in formula 1 below -3].
【Chemical formula 1-1】
【Chemical formula 1-2】
【Chemical formula 1-3】
It is preferred that the M in chemical formula 1-2 represents Al, Mg, Ca, Sr or Ba.In the synthesis example of the present invention, the M tables
Show Al and n=3, m1For 1 or 2.
It is preferred that the q in chemical formula 1-3 is 3, and L2For NR1R2.In the synthesis example of the present invention, the L2For N
(CH3)2, m1For 1 or 2.
It is preferred that the structure of the compound shown in the chemical formula 1 is
X1、X2、X3And X4For identical or different and respective expression
Hydrogen or halogen atom, its condition is X1、X2、X3And X4It is not simultaneously hydrogen, and m1With m2It is not 0.More preferably, X1、X2、X3And X4
For chlorine atom, the Y1Represent SO3H, and the Y2Represent SO2NH-(CH2)q-L2(as shown in formula 1 below -4).Again more preferably, L2
For NR1R2.In the synthesis example of the present invention, the L2For N (CH3)2, q=3, m1For 1 and m2For 1.
【Chemical formula 1-4】
It is preferred that in the compound shown in chemical formula 1, shouldRepresentThe X5、X6、X7、X8、
X9And X10To be identical or different and each represent hydrogen or halogen atom, structure is as follows：
More preferably, the m2For 0, structure is as follows：
Again more preferably, the X5、X6、X7、X8、X9And X10Respectively hydrogen atom, the Y1Represent SO3H [such as formula 1 below -5
It is shown, m1For 1 or 2]：
【Chemical formula 1-5】
The synergist comprising it is a kind of, two or more as the compound shown in chemical formula 1.In the tool of the present invention
In style, the synergist (is namely somebody's turn to do the kind of the compound as shown in chemical formula 1 comprising a kind of compound as shown in chemical formula 1
Class is one kind), the chemical formula 1 is as shown in chemical formula 1-1.In another concrete example of the present invention, the synergist includes one kind
As the compound shown in chemical formula 1, the chemical formula 1 is as shown in chemical formula 1-2.In another concrete example of the present invention, the increasing
Imitate agent and include a kind of compound as shown in chemical formula 1, the chemical formula 1 is as shown in chemical formula 1-3.In another tool of the present invention
In style, the synergist includes a kind of compound as shown in chemical formula 1, and the chemical formula 1 is as shown in chemical formula 1-5.Yu Ben
In another concrete example of invention, the synergist (namely should be by the institute of chemical formula 1 as the compound shown in chemical formula 1 comprising two kinds
Show compound species be two kinds), in the chemical formula 1 of one of which compound be as shown in chemical formula 1-3, in anotherization
The chemical formula 1 of compound is as shown in chemical formula 1-4.
When the synergist contains two or more the compound as shown in chemical formula 1, the consumption of every kind of compound
Can be according to m1(and/or m2) value size and subsequent applications are adjusted.For example, when the synergist contains one kind by chemical formula 1-1
Compound P3 and one kind are as shown in chemical formula 1-4 during compound P4 as shown in chemical formula 1-3 for shown compound P1, one kind, P1/
(P3+P4) consumption ratio range is It is preferred that P1/ (P3+P4) consumption ratio range is
The preparation method of synergist of the present invention can be carried out according to general chemical synthesis mode, with shown in chemical formula 1-1
Exemplified by compound, can by make C.I. solvent of red 135 [entitled 8,9,10, the 11- tetra- chloro- 12H- phthaleins peri-position -12- ketone of chemistry (8,9,
10,11-tetrachloro-12H-phthaloperin-12-one), as shown in following chemical formula] carry out it is sulfonated reaction and
Obtain：
By taking compound shown in chemical formula 1-2 as an example, sulfonated reaction can be first carried out by making C.I. solvent of red 135, then with
Salt containing M carries out precipitation reaction and obtained.In a specific example of the present invention, it is aluminum sulfate to be somebody's turn to do the salt containing M.
, can be by making C.I. solvent of red 135 first carry out sulfonic acid by taking compound shown in chemical formula 1-3 and chemical formula 1-4 as an example
Change reaction, through thionyl chloride (SOCl2) generation sulfonic acid chloride after, then with NH2-(CH2)q-L2Carry out sulphur aminating reaction and obtain.Yu Ben
In one concrete example of invention, NH2-(CH2)q-L2For NH2-(CH2)3-N(CH3)2。
, can be by making { the chemical entitled 14H- benzos [4,5] of C.I. solvent reds 179 by taking compound shown in chemical formula 1-5 as an example
Different benzoquinones [2,1-a] pyridine -14- ketone (14H-benzo [4,5] isoquino [2,1-a] perimidin-14-one) pah, it is such as following
Shown in chemical formula } carry out sulfonated reaction and obtain：
[color compositions]
Color compositions of the present invention include organic red pigment and at least one synergist.
The consumption of the synergist is to be changed according to the organic red pigment into subassembly and consumption, it is preferred that with
The consumption of the organic red pigment is 100 parts by weight meters, and the consumption of the synergist is 0.1 to 30 parts by weight.
It is preferred that the organic red pigment is to be selected from diketopyrrolo-pyrrole class (diketopyrrolopyrroles)
Pigment, anthraquinone (anthraquinone) class pigment or foregoing combination.The commercial goods example of the diketopyrrolo-pyrrole class pigment
As but be not limited to (such as BASF of C.I. paratoneres 254Red S3611 CF), C.I. paratoneres 255, C.I. paratoneres
264th, C.I. paratoneres 272 etc..The commercial goods of the Anthraquinones pigment are such as, but not limited to C.I. paratoneres 177, C.I. pigment
Red 83, C.I. pigment Red 8s 5, C.I. pigment Red 8s 9, C.I. paratoneres 168, C.I. paratoneres 194, C.I. paratoneres 194, C.I.
Paratonere 195, C.I. paratoneres 196 etc..Foregoing various organic red pigments individually one kind can be used or be combined two
Kind or more than two kinds use.In a specific example of the present invention, the organic red pigment is C.I. paratoneres 254 and C.I. face
Expect red 177 combination.
It is preferred that the color compositions are also comprising toning organic pigment, the toning organic pigment and organic red pigment are not
Together, be other do not influence the properties such as the dispersiveness, stability, light peneration of color compositions other colors pigment.The tune
The commercial goods of color pigment are such as, but not limited to C.I. pigment oranges 73, C.I. pigment oranges 40, C.I. pigment orange 5s 1, C.I. pigment oranges
77 etc..Foregoing various toning organic pigments individually one kind can be used or be combined two or more to use.
[color]
Color of the present invention includes organic red pigment, synergist, solvent and dispersant.
The organic red pigment is as described in foregoing [color compositions] on " organic red pigment ", and the synergist is as before
State described in [synergist].The solvent is such as, but not limited to propylene glycol methyl ether acetate, propylene glycol monomethyl ether, cyclohexanone, n-butanol
Deng.Foregoing various solvents individually one kind can be used or be combined two or more to use.In the tool of the present invention
In style, the solvent is propylene glycol methyl ether acetate and n-butanol.
The dispersant is such as, but not limited to LP-N-21324 and LP-N-21116, LP- manufactured by BYK Chemie companies
N-21208、LP-N-6919、Disperbyk-2000、Disperbyk-2001；EFKA-4300 manufactured by BASF AG,
EFKA-4330、EFKA-4340、EFKA-4400、EFKA-4401、EFKA-4402、EFKA-4046、EFKA-4060；
Ajisper PB821, PB822, PB880 manufactured by Ajinomoto companies；Solsperse manufactured by Lubrizol companies
20000th, Solsperse 24000, Solsperse 27000, Solsperse 28000 etc..Foregoing various dispersants can be with
Individually one kind is used or combined two or more to use.In the concrete example of the present invention, the dispersant is BYK
LP-N-21324 and LP-N-21116 manufactured by Chemie companies.
The color is selectively also comprising dispersion resin, toning organic pigment or both foregoing combinations.The dispersion resin
Such as, but not limited to polyacrylic acid (polyacrylate) resin, block many (cardo) resins, polyester (polyester) resin, gather
Acid imide (poly imide) resin etc..Foregoing various dispersion resins individually one kind can be used or be combined two kinds or two
Used more than kind.The toning organic pigment is as described in foregoing [color compositions] on " toning organic pigment ".
In color, the organic red pigment, synergist, solvent and dispersant consumption can be according to being actually needed progress
Adjustment.It is preferred that being calculated by 100wt% of the gross weight of the color, the amount ranges of the organic red pigment are 5~20wt%,
The amount ranges of the synergist are 0.1~4wt%, and the amount ranges of the dispersant are 5~15wt%, the amount ranges of the solvent
For 70~85wt%.More preferably, the amount ranges of the organic red pigment are 10~18wt%, and the amount ranges of the synergist are
0.1~2wt%, the amount ranges of the dispersant are 7~10wt%, and the amount ranges of the solvent are 75~80wt%.
Embodiment
The present invention will be described further with regard to following examples, however, it should be noted that the embodiment is only to illustrate it
With, and it is not necessarily to be construed as the limitation of implementation of the invention.
<Embodiment>
[embodiment 1] includes the preparation of the synergist of compound shown in chemical formula 1-1
By 480 parts, 20%SO3Oleum be positioned in round-bottomed bottle, being put into magnetite in the round-bottomed bottle is stirred,
The round-bottomed bottle is positioned in water-bath again.Take 70.5 parts of C.I. solvent of red 135 and be slowly added in above-mentioned round-bottomed bottle, and allow
Bath temperature is less than 40 DEG C.Reaction solution is formed after the C.I. solvent of red 135 in round-bottomed bottle is completely dissolved, then makes the reaction solution
React 1 hour at room temperature.Extract 0.5mL reaction solutions and add in 10mL water, confirm that the reactant can be dissolved in water totally, connect
, 2000 parts of butanone is added in beaker and beaker is positioned in ice bath, then above-mentioned reaction solution is slowly added to beaker
One mixed liquor of interior formation, and the fluid temperature allowed in beaker is less than 40 DEG C.The mixed liquor is carried out filtering and obtain crude product, then profit
Crude product is cleaned repeatedly with butanone.After cleaning every time, cleaning fluid is collected, and 1 part of cleaning fluid and 4 parts of water are carried out mixing acquisition
Test fluid, recycles conductoscope (being purchased from EUTECH companies, model COND 6+) test fluid is carried out conductivity test.
Until the conductance of test fluid less than 200 μ S/cm is to terminate cleaning step, the crude product after cleaning is positioned over to 60 DEG C of baking oven
It is middle to be dried, finally crushed and toasted in 150 DEG C of baking ovens 1 hour again, that is, obtain 99.6 parts of dark red solid production
Thing.
Above-mentioned dark red solid product is set to carry out analysis below：
1. the sulfonated value of per molecule：Determined using elemental analyser (commission Taiwan Test Technology Co., Ltd. SGS),
Measure sulphur atom and account for the moleculeI.e. per molecule is sulfonated
It is worth for 1.8.
2.IR spectrum analyses：The dark red solid product is positioned in agate mortar with KBr and pulverizes last, then is taken
Go out powder and salt piece is made.The salt piece is positioned over infrared spectrum tester and (is purchased from Perkin Elmer companies, model
Spectrum 100) tested and obtain IR spectrum.The IR spectrum of this IR spectrum and C.I. solvent of red 135 are compared,
It can be found that this dark red solid product is in 1030cm-1There are strong S=O signals at place, and based on above-mentioned 1st point of elementary analysis
And the test of the sulfonated value of per molecule, can confirm that the dark red solid product is compound (m shown in chemical formula 1-11For 1)
And compound (m shown in chemical formula 1-11For 2).
[embodiment 2] includes the preparation of the synergist of compound shown in chemical formula 1-2
The product of embodiment 1 of 3.0 parts by weight is taken, 85.9 parts by weight is added and concentration is the 0.1722N KOH aqueous solution and stirred
Mix uniform, the Al of 1.52 parts by weight is slowly added into afterwards2(SO4)3·16H2O obtains reaction solution.By reaction solution stand it is overnight after,
Solid precipitation can be observed.Filter the reaction solution and with washed several times with water, the red powder of 2.54 parts by weight is obtained after drying.
IR spectrometry procedures according to embodiment 1 are analyzed, and sulfonate radical news can be observed by the IR spectrum obtained
Number in 1036cm-1, it is possible thereby to confirm that the red powder is compound (M=Al, n=3, m shown in chemical formula 1-21=1) and
Compound (M=Al, n=3, m shown in chemical formula 1-21=2).The sulfonated value of per molecule is same as Example 1, is 1.8.
[embodiment 3] includes the preparation of the synergist of compound shown in compound shown in chemical formula 1-3 and chemical formula 1-4
A two-neck bottle is taken, the product of embodiment 1 of 10.0 parts by weight is added, the thionyl chloride and 60 weights of 30.0 parts by weight is added
Measure the dimethylformamide of part and obtain reaction solution.Reaction solution is set to be heated to 90 DEG C and react 5 hours.Question response liquid is cooled to room
Wen Hou, reaction solution is instilled in frozen water, collects solid, and to wash 3 times.Solid is placed in the frozen water of 200 parts by weight (ice/
Water=1/1).In under ice bath, by the N of 16.0 parts by weight, N- Dimethylaminopropyl amine is slowly added in the solid, stirs 5 points
Mixed liquor is obtained after clock.The temperature of mixed liquor is increased to 90 DEG C and reacted 1.5 hours.Adjusted mixed liquor ice bath and with the concentrated sulfuric acid
Behind whole pH=1~2, there is solid precipitation, to wash solid until filter liquor electrical conductivity is less than after 200 μ S/cm, be dried to obtain 10.6
The brown solid of parts by weight.
IR spectrometry procedures according to embodiment 1 are analyzed, and sulfonamide news can be observed by the IR spectrum obtained
Number in 1027cm-1And sulfonate radical signal is in 1036cm-1, it is possible thereby to confirm that the brown solid includes chemical formula 1-3 shownization
Compound (q=3, L2=N (CH3)2, m1=1), compound (q=3, L shown in chemical formula 1-32=N (CH3)2, m1=2) and the change
Compound (q=3, L shown in formula 1-42=N (CH3)2, m1=1 and m2=1).
Above-mentioned brown solid is set to carry out analysis below：
Determined using elemental analyser (commission Taiwan Test Technology Co., Ltd., SGS companies), measure sulphur atom and account for
8.29%, nitrogen-atoms accounts for 10.58%, and the change is can be calculated by the Elemental analysis data of table 1 below and three formulas of the lower section of table 1
Compound (q=3, L shown in formula 1-32=N (CH3)2, m1=2) account for 62%, and compound (q=shown in chemical formula 1-4
3, L2=N (CH3)2, m1=1 and m2=18% 1) is accounted for, compound (q=3, L shown in chemical formula 1-32=N (CH3)2, m1=1)
20% is accounted for, the sulfonated value of per molecule is 0.18, and per molecule sulfuryl amine value is 1.62.
【Table 1】
11.41a+8.59b+9.79c=10.58, [a is chemical formula by 8.71a+9.83b+5.60c=8.29 and a+b+c=1
Compound (m shown in 1-31=2) shared by percentage composition；B is compound (m shown in chemical formula 1-41=1 and m2=1) shared contain
Measure percentage；C is compound (m shown in chemical formula 1-31=1) shared by percentage composition].
[embodiment 4] includes the preparation of the synergist of compound shown in chemical formula 1-5
In addition to C.I. solvent of red 135 used in embodiment 1 is changed into C.I. solvent reds 179, remaining Step By Condition
As described in Example 1, that is, 113.1 parts of red solid product is obtained.The red solid product is chemical combination shown in chemical formula 1-5
Thing (m1=1) and compound (m shown in chemical formula 1-51=2).
Above-mentioned red solid product is set to carry out analysis below：
The sulfonated value of per molecule：Determined using elemental analyser (commission GHS), measure sulphur atom and account for the molecule
13.0%, it is 1.9 to imply that the sulfonated value of per molecule.
[comparative example 1] compound shown in following chemical formula 2
【Chemical formula 2】
The compound of comparative example 1 is available from Japanese Daiwa companies, model 254SR.
The preparation of [application examples 1 to 4] and [comparing application examples 1 and 2] color
Application examples 1 to 3 and the common preparation method of color for comparing application examples 1 and 2：According to the usage ratio of table 2 below, red is had
Machine pigment (is manufactured using BASF AGRed S3611 CF), synergist, solvent (propylene glycol monomethyl ether vinegar
Acid esters and n-butanol) and dispersant (LP-N-21324 and LP-N-21116) add the 0.3mm zirconiums of 4 times of color weight at room temperature
Ball, is placed in appropriately sized PP grinding pots, and (red devil equipment are purchased from using Red Devil paint mixer
Company, model 1400-OH) mix 1 hour, filtering is removed after zirconium ball, obtains color.
Application examples 1 is the synergist (including compound shown in chemical formula 1-1) using embodiment 1, and application examples 2 is using real
The synergist (including compound shown in chemical formula 1-2) of example 2 is applied, application examples 3 is the synergist using embodiment 3 (comprising chemistry
Compound shown in compound shown in formula 1-3 and chemical formula 1-4), application examples 4 is (to include chemical formula using the synergist of embodiment 4
Compound shown in 1-5), compare application examples 1 and synergist is not used, it is the synergist using comparative example 1 to compare application examples 2.
3. test：
Application examples 1 to 4 carries out following test respectively with being compared the color of application examples 1 and 2, as a result arranges in table 3：
(1) theoretical solid content and actual solid content (wt%)：Theoretical solid content is by the organic red pigment in table 1, increased
The consumption of effect agent and dispersant, which is added up, to be obtained.Take 1 gram of color to be positioned on aluminum dish and obtain test sample, then this is tested
Sample carries out weighing and obtains toasting preceding weight；Afterwards, test sample is positioned over 150 DEG C of heater plates 60 minutes and carries out scale
Weight, weight after being toasted.
(2) particle diameter (nm)：Using propylene glycol monomethyl ether acetate, color is diluted after 500 times, dissipated with dynamic laser light
Penetrate instrument (DKSH companies manufacture, model Zetasizer 1000HSA) and measure average grain diameter (Zave).
(3) original viscosity (cp)：Using viscosimeter (being manufactured by Dong Ji industry companies, model TVE-20L) in 25 DEG C, turns
The viscosity of color is measured under the conditions of rotor speed 60rpm.
(4) viscosity and rate of change in viscosity of the room temperature after 1 week：Color is placed 1 week under room temperature (temperature range is 23~28 DEG C)
Afterwards, the viscosity of viscosity measurement colour examining cream is recycled.Calculate again
(5) C.I.E. chromaticity coordinates figure：Using spin coater (TOBI Co., Ltd. manufactures, model MSC-450), by color
Cream is coated on thickness 0.7mm glass substrate.Thereafter, in dry 3 minutes in 100 DEG C of heating plate.Followed by micro- point
Light measurement device (great Zhong Electronics Co., Ltd manufactures, model LCF-6000, optical splitter model MCPD-2000) is measured, can
Obtain C.I.E. chromaticity coordinates (Y, x, y).
【Table 2】
【Table 3】
From the result of table 2 and 3, application examples 1 to 4 is compared with being compared application examples 1 and 2, it can be found that using
The particle diameter and rate of change in viscosity of example 1 to 4, which are all less than, compares application examples 1 and almost consistent with being compared application examples 2, and this hair is added in display
Bright synergist can improve the dispersiveness of organic red pigment and the stability of color really, while can meet commercially available synergy
The standard of agent (such as comparing application examples 2).Compare with being compared application examples 1, add the application examples 1~4 of chemical formula 1~5, its viscosity is steady
It is qualitative to be improved.Compare with being compared application examples 2, although its viscosity stability can be improved, but compared to unused
The comparison application examples 1 of synergist has brightness (Y value) and declines more situation.Application examples 2 and addition chemical formula 1~5 will be compared
Application examples 1~4 be compared, it is also seen that brightness (Y value) performance of application examples 1~4 is preferable.
Application examples 1 and 2 is compared with being compared application examples 2, it can be found that the rate of change in viscosity of application examples 1 and 2 is less than
Compare application examples 2, it was demonstrated that synergist (synergist for particularly including compound shown in chemical formula 1-1 or 1-2) of the invention can
To allow the stability of follow-up obtained color to be better than commercially available synergist.
The preparation of [application examples 5 to 8] and [comparing application examples 3 and 4] color
Except by organic red pigment be replaced into first Nico chemical company (Cinic Chemicals (Shanghai) Co.,
Ltd C.I. paratoneres 177 (model SR4C), dispersant manufactured by) use the use of LP-N-21116 and changing section composition
Amount is outer, prepared by the step of color of application examples 5 to 8 is according to application examples 1 to 3.
Except by organic red pigment be replaced into first Nico chemical company (Cinic Chemicals (Shanghai) Co.,
Ltd C.I. paratoneres 177 (model SR4C), dispersant manufactured by) using LP-N-21116 and according to the changing section of table 4 into
Outside the consumption divided, the color for comparing application examples 3 and 4 is to be prepared the step of foundation compares application examples 1 and 2.
Application examples 5 to 8 carries out the same test of application examples 1 with being compared the color obtained by application examples 3 and 4 respectively, as a result
Arrange in table 5.
【Table 4】
【Table 5】
From the result of table 4 and 5, application examples 5 to 8 is compared with being compared application examples 3, it can be found that application examples 5
Rate of change in viscosity to 8 is all less than application examples 3 is compared, and the synergist of the display addition present invention can improve red organic face really
The dispersiveness and the stability of color of material.Comparison application examples 3 compared to unused synergist or the comparison application using 254SR
Example 4, brightness (Y value) performance of application examples 5 to 8 is relatively preferred or equal.
Application examples 5 is compared with being compared application examples 4, it can be found that the particle diameter of application examples 5, rate of change in viscosity are all less than
Compare application examples 4, show that synergist (synergist for particularly including compound shown in chemical formula 1-1) of the present invention can allow follow-up system
The dispersiveness and stability of the color obtained are better than commercially available synergist.
The preparation of [application examples 9 to 11] color
Except synergist is replaced into the synergist (including compound shown in chemical formula 1-1) using embodiment 1 with implementing
Outside the combination of the synergist (including compound shown in compound shown in chemical formula 1-3 and chemical formula 1-4) of example 3, application examples 9 to 11
Color be according to application examples 1 to 3 the step of prepared.Color obtained by application examples 9 to 11 carries out application examples 1 respectively
Same test, is as a result arranged in table 6.
【Table 6】
As shown in Table 6, by the embodiment 1 to 4 of application examples 9 to 11 and table 1, compared application examples 1 and 2 and compared
Compared with it can be found that the rate of change in viscosity of application examples 9 to 11 is equal to 0% or less than 0%, display addition contains two or more compounds
Synergist (particularly as shown in chemical formula 1-1 compound, compound shown in chemical formula 1-3 and compound shown in chemical formula 1-4
Combination) can more lift the stability of color.Application examples 2 will be compared to be compared with application examples 9 to 11, it is also seen that application examples
9 to 11 brightness (Y value) performance is preferable.
The preparation of [application examples 12 to 14] color
Except by organic red pigment be replaced into first Nico chemical company (Cinic Chemicals (Shanghai) Co.,
Ltd C.I. paratoneres 177 (model SR4C), dispersant manufactured by) use the use of LP-N-21116 and changing section composition
Amount is outer, prepared by the step of color of application examples 12 to 14 is according to application examples 9 to 11.Color obtained by application examples 12 to 14
Cream carries out the same test of application examples 1 respectively, as a result arranges in table 7 and table 8.
【Table 7】
【Table 8】
From the result of table 7 and 8, by the embodiment 5 to 8 of application examples 12 to 14 and table 2, compared application examples 3 and 4 and carried out
Compare, it can be found that the rate of change in viscosity of application examples 12 to 14 is equal to 0% or less than 0%, display addition contains two or moreization
Synergist (compound, compound shown in chemical formula 1-3 and the change shown in chemical formula 1-4 particularly as shown in chemical formula 1-1 of compound
The combination of compound) it can more lift the stability of color.Compared to the comparison application examples 3 of unused synergist or using 254SR
Compare application examples 4, brightness (Y value) performance of application examples 12 to 14 is relatively preferred or equal.
In summary, by the present invention in that with the synergist designed with special construction, being able to allow containing the synergist
Color compositions possess good dispersiveness and stability；In addition, color compositions of the present invention selectively further avoid color
The generation of tuningout Huang phenomenon and can maintain pretty good brightness, and allow simultaneously it is follow-up obtained by color be more suitable for applying and requiring presentation
In the fields such as the colored filter or jetted ink of high contrast hue, therefore the purpose of the present invention can be reached really.
Only as described above, only embodiments of the present invention are all when that can not limit the scope of implementation of the invention with this
It is the simple equivalent changes and modifications made according to scope of the present invention patent and patent specification content, all still belongs to the present invention
In the range of patent covers.
Claims (15)
1. a kind of synergist, includes at least one compound as shown in chemical formula 1：
【Chemical formula 1】
Wherein,RepresentX1、X2、X3And X4For identical or different and respective table
Show hydrogen, halogen atom, alkyl or acyl group, its condition is X1、X2、X3And X4It is not simultaneously hydrogen, X5、X6、X7、X8、X9And X10For
It is identical or different and each represent hydrogen, halogen atom, alkyl or acyl group；
Y1And Y2Be respectively connecting to naphthalene nucleus,Or foregoing two ring, it is respectively different and expression SO3H、[SO3]nM、SO2-(CH2)p-
L1、SO2NH-(CH2)q-L2、SO2N-[(CH2)r-L3][(CH2)s-L4]；
Wherein, M represents n valency metals；
N represents 1 to 3 integer；
P, q, q, r, s each represent 1 to 8 integer；
L1Represent hydrogen, COOH, NR1R2, morpholinyl, N methyl piperazine base, piperazinyl, pyrazolyl, imidazole radicals or piperidyl；
L2、L3And L4Each represent COOH, NR1R2, morpholinyl, N methyl piperazine base, piperazinyl, pyrazolyl, imidazole radicals or piperidines
Base；
R1And R2Each represent hydrogen, C1~C8Alkyl, benzyl or C3~C5Cycloalkyl；And
m1And m2The integer of expression 0 to 4, and m respectively1+m2For 1 to 4 integer.
2. synergist as claimed in claim 1, wherein, should in the compound shown in the chemical formula 1RepresentThe X1、X2、X3And X4To be identical or different and each represent hydrogen or halogen atom, its condition is X1、X2、X3
And X4It is not simultaneously hydrogen.
3. synergist as claimed in claim 2, wherein, in the compound shown in the chemical formula 1, the X1、X2、X3And X4Respectively
For chlorine atom, the Y1Represent SO3H、[SO3]nM or SO2NH-(CH2)q-L2, m2For 0.
4. synergist as claimed in claim 3, wherein, in the compound shown in the chemical formula 1, the Y1Represent SO2NH-
(CH2)q-L2, q is 3, and L2For NR1R2。
5. synergist as claimed in claim 1, wherein, it is one kind, the chemical formula to be somebody's turn to do the species of the compound as shown in chemical formula 1
Being somebody's turn to do in 1RepresentThe X1、X2、X3And X4Respectively chlorine atom, the Y1Represent SO3H, m2For 0.
6. synergist as claimed in claim 1, wherein, it is one kind, the chemical formula to be somebody's turn to do the species of the compound as shown in chemical formula 1
Being somebody's turn to do in 1RepresentThe X1、X2、X3And X4Respectively chlorine atom, the Y1Represent [SO3]nM。
7. synergist as claimed in claim 1, wherein, it is one kind, the chemical formula to be somebody's turn to do the species of the compound as shown in chemical formula 1
Being somebody's turn to do in 1RepresentThe X1、X2、X3And X4Respectively chlorine atom, the Y1Represent SO2NH-(CH2)q-L2。
8. synergist as claimed in claim 1, wherein, it is one kind, the chemical formula to be somebody's turn to do the species of the compound as shown in chemical formula 1
In 1RepresentThe X5、X6、X7、X8、X9And X10To be identical or different and each represent hydrogen or halogen
Atom.
9. synergist as claimed in claim 1, wherein, the species for being somebody's turn to do the compound as shown in chemical formula 1 is three kinds, the chemical formula
Being somebody's turn to do in 1Represent
In the X of one of which compound1、X2、X3And X4Respectively chlorine atom, the Y1Represent SO3H；
The X in the chemical formula 1 of another compound1、X2、X3And X4Respectively chlorine atom, the Y1Represent SO2NH-
(CH2)q-L2；
The X in the chemical formula 1 of another compound1、X2、X3And X4Respectively chlorine atom, the Y1Represent SO3H, and Y2Table
Show SO2NH-(CH2)q-L2And m1And m2It is not 0.
10. synergist as claimed in claim 1, wherein, in the compound shown in chemical formula 1
In, shouldRepresentThe X5、X6、X7、X8、X9And X10For identical or different and respective expression hydrogen or halogen
Plain atom.
11. synergist as claimed in claim 10, wherein, in the compound shown in the chemical formula 1, the X5、X6、X7、X8、X9
And X10Respectively hydrogen atom, the Y1Represent SO3H, m2For 0.
12. a kind of color compositions, comprising：
Organic red pigment；And
Synergist as any one of claim 1 to 11.
13. color compositions as claimed in claim 12, wherein, counted by 100 parts by weight of the consumption of the organic red pigment,
The consumption of the synergist is 0.1 to 30 parts by weight.
14. color compositions as claimed in claim 12, wherein, the organic red pigment be selected from pyrrolopyrrole class pigment,
Anthraquinones pigment or foregoing combination.
15. a kind of color, comprising：
Organic red pigment；
Synergist as any one of claim 1-11；
Solvent；And
Dispersant.
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| TW105109190A TWI574964B (en) | 2016-03-24 | 2016-03-24 | A multiplier, a pigment composition containing the same, and a colorant |
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| JPS5272726A (en) * | 1975-12-16 | 1977-06-17 | Mitsubishi Chem Ind Ltd | Production of water-soluble dye |
| 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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| TW201734016A (en) | 2017-10-01 |
| TWI574964B (en) | 2017-03-21 |
| CN107227044B (en) | 2020-04-14 |
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