CN109554004A - Pigment dispersing agent and application thereof - Google Patents
Pigment dispersing agent and application thereof Download PDFInfo
- Publication number
- CN109554004A CN109554004A CN201811540571.9A CN201811540571A CN109554004A CN 109554004 A CN109554004 A CN 109554004A CN 201811540571 A CN201811540571 A CN 201811540571A CN 109554004 A CN109554004 A CN 109554004A
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- CN
- China
- Prior art keywords
- pigment
- amino
- naphthalimide
- dispersing agent
- pigment dispersion
- Prior art date
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- 239000000049 pigment Substances 0.000 title claims abstract description 108
- 239000002270 dispersing agent Substances 0.000 title claims abstract description 28
- 239000006185 dispersion Substances 0.000 claims abstract description 48
- -1 substituted-amino anthraquinones Chemical class 0.000 claims abstract description 36
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 6
- 125000003368 amide group Chemical group 0.000 claims abstract description 5
- 239000001054 red pigment Substances 0.000 claims abstract description 5
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 4
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 4
- 150000002790 naphthalenes Chemical class 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 229920000768 polyamine Polymers 0.000 claims abstract description 4
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical group 0.000 claims abstract description 3
- 150000001721 carbon Chemical group 0.000 claims abstract 2
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 11
- 239000011347 resin Substances 0.000 claims description 9
- 229920005989 resin Polymers 0.000 claims description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical group CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 claims description 5
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexamethylene diamine Natural products NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- QOMPUPSCNWHNHA-UHFFFAOYSA-N 1-amino-2-anilinoanthracene-9,10-dione Chemical class NC1=C(C=CC=2C(C3=CC=CC=C3C(C12)=O)=O)NC1=CC=CC=C1 QOMPUPSCNWHNHA-UHFFFAOYSA-N 0.000 claims description 2
- NJISMZXTNCCWMK-UHFFFAOYSA-N 1-n',1-n'-diethylbutane-1,1-diamine Chemical compound CCCC(N)N(CC)CC NJISMZXTNCCWMK-UHFFFAOYSA-N 0.000 claims description 2
- UXHXJLUCIJFHIS-UHFFFAOYSA-N 1-n',1-n'-diethylpentane-1,1-diamine Chemical compound CCCCC(N)N(CC)CC UXHXJLUCIJFHIS-UHFFFAOYSA-N 0.000 claims description 2
- USNXAEGVSAOWNJ-UHFFFAOYSA-N N-(4-amino-9,10-dioxoanthracen-1-yl)propanamide Chemical class NC1=CC=C(C=2C(C3=CC=CC=C3C(C12)=O)=O)NC(CC)=O USNXAEGVSAOWNJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000004040 coloring Methods 0.000 claims description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 claims 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 claims 2
- CVQDLPIREXNIHP-UHFFFAOYSA-N 1,2,3,4,5,6-hexaaminoanthracene-9,10-dione Chemical class NC=1C(=C2C(C=3C(=C(C(=C(C=3C(C2=CC=1)=O)N)N)N)N)=O)N CVQDLPIREXNIHP-UHFFFAOYSA-N 0.000 claims 1
- XJXWRADQYNMQHL-UHFFFAOYSA-N 1-n',1-n'-dimethylhexane-1,1-diamine Chemical compound CCCCCC(N)N(C)C XJXWRADQYNMQHL-UHFFFAOYSA-N 0.000 claims 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 claims 1
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 claims 1
- IXUJSVVQCPFGAV-UHFFFAOYSA-N 4-piperidin-1-ylbutanamide Chemical class NC(=O)CCCN1CCCCC1 IXUJSVVQCPFGAV-UHFFFAOYSA-N 0.000 claims 1
- PXNNPGGYHAWDJW-UHFFFAOYSA-N N-(4-amino-9,10-dioxo-1-anthracenyl)benzamide Chemical group C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=CC=C1NC(=O)C1=CC=CC=C1 PXNNPGGYHAWDJW-UHFFFAOYSA-N 0.000 claims 1
- 150000003983 crown ethers Chemical class 0.000 claims 1
- UICBCXONCUFSOI-UHFFFAOYSA-N n'-phenylacetohydrazide Chemical compound CC(=O)NNC1=CC=CC=C1 UICBCXONCUFSOI-UHFFFAOYSA-N 0.000 claims 1
- CKLPECFHCLIYKN-UHFFFAOYSA-N n'-phenylbenzohydrazide Chemical compound C=1C=CC=CC=1C(=O)NNC1=CC=CC=C1 CKLPECFHCLIYKN-UHFFFAOYSA-N 0.000 claims 1
- 238000003860 storage Methods 0.000 abstract description 5
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 238000001879 gelation Methods 0.000 abstract description 2
- 230000008719 thickening Effects 0.000 abstract description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 2
- 238000006467 substitution reaction Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 description 27
- 239000002585 base Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 8
- 239000010408 film Substances 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 238000002834 transmittance Methods 0.000 description 8
- 239000003086 colorant Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 239000012860 organic pigment Substances 0.000 description 6
- 230000005540 biological transmission Effects 0.000 description 5
- 239000004973 liquid crystal related substance Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 229920000178 Acrylic resin Polymers 0.000 description 4
- 239000004925 Acrylic resin Substances 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- LZKGFGLOQNSMBS-UHFFFAOYSA-N 4,5,6-trichlorotriazine Chemical compound ClC1=NN=NC(Cl)=C1Cl LZKGFGLOQNSMBS-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 108010021119 Trichosanthin Proteins 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 238000005034 decoration Methods 0.000 description 3
- 150000004816 dichlorobenzenes Chemical class 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000003486 chemical etching Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000004070 electrodeposition Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229920005732 JONCRYL® 678 Polymers 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 206010034960 Photophobia Diseases 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000001055 blue pigment Substances 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 150000005125 dioxazines Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000009713 electroplating Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 208000013469 light sensitivity Diseases 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 238000004045 reactive dyeing Methods 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- 230000000007 visual effect Effects 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
- C09B67/0084—Dispersions of dyes
- C09B67/0085—Non common dispersing agents
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Optical Filters (AREA)
Abstract
A kind of Red Pigment Dispersion agent, general formula are as follows:
Description
Technical field
The invention belongs to organic pigment, water paint and liquid crystal display crossing domains, and being related to one kind can be used for LCD TV
Colour filter red pigment nano dispersion fluid extremely preparation method.
Technical background
There is display device high-resolution and picture quality to have become necessarily requiring for electronic product.Meanwhile people couple
The light, thin of electronic product, wide-angle is visual and low energy consumption requirement is also higher and higher.In face of such demand, it has been developed that LCD
(liquid crystal display) product.
LCD is non-active luminescent device, and color displays light source must back light system (transmission-type) by itself or outside
Environment light (emission type or semi-transparency type) provide.Grayscale is formed by driver and controller to show, recycles color filter
Piece generates red (R), green (G), blue (B) three primary colours (Primary color), forms colored display picture according to colour mixture principle.It is color
Color colour filter is made of glass substrate, black matrix", color layer, protective layer and ITO conductive film.Glass substrate is chromatic color filter
Carrier, generally use heat-resisting, resistant to chemical etching and good mechanical performance alkali-free Pyrex；Black matrix" is in order to prevent
Light leakage, color contamination confuse and increase contrast and design；Colored film (CF) is made of R, G, B three primary colours film, and configuration mode is general
There are stripe, Mosaic style and triangular form；To prevent pollution, the chemical resistance of enhancing color layer, anti-ITO from sputtering and improving it and putting down
Slip need to deposit protective layer, finally deposit ITO electrode after forming color layer.The ITO electrode and figure of colored filter
Electrode constitutes the positive and negative anodes of driving liquid crystal molecule.Transparent electrode answers conductive and translucency, therefore it is required that it have compared with
Low resistance and higher light transmittance.
The material and technique of color layer determine the spectral characteristic of chromatic color filter, flatness and heat-resisting, resistant to chemical etching
Property.The performance of liquid crystal display colour filter should meet claimed below:
(1) high excitation purity and high transmittance
Excitation purity and transmitance are to reflect the ability and range of display device performance color.High color purity and high-transmission rate are
TFT-LCD shows performance indicator essential to high resolution image true to nature rich in color.Constitute the pigment and pigment light of color layer
Resistance is to influence the deciding factor of excitation purity and transmitance.R, the projection spectrum of G, B three primary colours is answered moderate, and transmission peak wavelength range is not
Can be too narrow, otherwise the light transmittance of color layer is too low；Transmission peak wavelength range can not it is too wide, otherwise three primary colours spectrum by occur weight
It is folded, keep the colour reproduction of colour filter less able.Therefore, the reasonable selection of pigment and pigment photoresistor is critically important.
(2) high contrast
Contrast refers under regulation lighting condition, the maximum brightness value (Quan Bai) of display and minimum luminance value (completely black)
Ratio.The reduced value of general TFT-LCD (thin film transistor liquid crystal display) is 200:1~400:1.For high color purity and height
For the picture of clarity, high contrast is most important.High contrast must require CF to have antiradar reflectivity requirement.
(3) good heat-resisting, fast light and chemical corrosion resistance
The rear process of LCD can meet with 250 DEG C or so of high temperature, therefore chromatic color filter should have good heat resistance, no
It can deform or change colour because heated, should also have good light resistance, will not fade because of the irradiation of backlight.In addition, must also
It must bear the corrosion of the chemical reagent such as acid, the alkali used in LCD manufacturing process.
The production of colored filter is exactly the organic material by Red Green Blue on the glass substrate, is produced on each
A pixel rate.More common colored filter production method has print process, electrodeposition process, decoration method and pigment dispersion method etc., tool
Body is as follows.
(1) print process
With the technique of print process production chromatic color filter by screen painting, flexopress, adherography printing and intaglio process
Four kinds of brush.The advantages of print process is at low cost, high production efficiency, the disadvantage is that product resolution ratio is low, profile pattern is poor.
(2) electrodeposition process
The pattern of ITO electrode is made to it is completely the same with pixel configuration mode, and by the electrode pattern of same color connect
It is electroplated together.The dispersion of colorant and resin micelle is put into electroplating bath, coating is just deposited on transparency conducting layer after energization
On.Three times using three kinds of different colorant plating, three color films are just obtained.The product surface of this method preparation is smooth, but ITO resistance
Variation can cause the variation of CF performance, and higher to the uniformity requirement of ITO.
(3) decoration method
Main material used in decoration method is water-soluble transparent polymer.Diazo compound or again is added in the polymer
Photosensitive material is made in chromate.Stainable photosensitive polymer is applied on the glass substrate, is rinsed by mask exposure and water,
Form transparent pattern, and with sour or reactive dyeing, the pattern after dyeing is handled with curing agent, to prevent colour migration, this technique
Also in triplicate (RGB is each primary).The colorized optical filtering flake products high color purity produced with this method, contrast is high, but its is heat-resisting
Chemical corrosion resistance is poor.
(4) pigment dispersion method
Pigment dispersion method is that first pigment is distributed in photosensitive resin, by light blockage coating, front baking, exposure, development, after
The techniques such as baking, etching are eventually fabricated chromatic color filter in triplicate after (RGB is each primary).Pigment dispersion method simple process,
Manufactured colour filter light sensitivity and resistance to optical activity are good, and precision is high, have very high heat-resistant stability, are resistant to 250 DEG C or so
High temperature, and there is preferable moisture-proof, wearability and chemical stability, it is in current chromatic color filter production using most
Main stream approach.
It include using ultraviolet light solidification photoresist printing ink (UV-Curable photoresists), organic in pigment dispersion method
Pigment, ultraviolet light solidification vector resin, photoinitiator (Photo initiator), organic solvent, dispersing agent etc..Wherein, organic
Pigment requires to have high vividness, three kinds of spectral hues of specific three primary colors (Primary color, R, G, B), durability, resistance to
Chemical reagent and the high grade of transparency etc..The organic pigment mainly selected is high-grade organic pigment kind, passes through efficient decentralized processing
Technique obtains the fine stable pigment dispersion of partial size.The technology that pigment dispersion method prepares most critical in colour filter is pigment
Apolegamy and dispersion technology.
According to Color Television Standards (McGraw-Hill, New York, 1955) and
Recommendation ITU-R BT 709-5(Parameter values for the HDTV standards for
Production and international programme exchange) in defined standard, red primary (red
Primary x=0.67, the requirement of y=0.33 (CIE, 1931)) should be met, green primary (green primary) should meet x=
0.21, y=0.71 (CIE, 1931)；The coordinate of blue primary is x=0.15 and y=0.06.In addition to chromaticity coordinate, three base of RGB
Color must also meet certain brightness and transmittance requirement, and the brightness requirement of red-green-blue is 21.4,52.1 Hes respectively
6.90。
In transmittance requirement, the max transmissive of green color filter is higher than 60% than requirement at 520nm, and in 590-
It is no more than 10% at 480nm, the halfwidth of transmission peaks is no more than 80nm.Halfwidth is transmittance peak at max transmissive is than half
Width.Chromaticity coordinate (x, y) of such color filter layer in 1931 CIE XYZ colorimetric systems uses CIE Standard Illuminant
D65 meets 0.19≤x≤0.24 and 0.68≤y≤0.72.
Red color filter requires have good transmittance in spectrum red area, and in green and green area with good
Good light absorption.This is usually realized by using the combination of two kinds of pigment: having good transmission ratio in the red area of spectrum
Red pigment and in 400-500nm range by the yellow uitramarine of maximum absorption wavelength.Final prepared red color filter
Max transmissive ratio, up to 80% or more, is no more than all transmittances of 10%, 580-410nm range in 585nm wavelength in 650nm wavelength
No more than 2%, chromaticity coordinate (xy) of such colour filter in 1931 CIE XYZ colorimetric systems uses CIE standard D65 light
Source calculates, and meets 0.665≤x≤0.68 and 0.30≤y≤0.34；
The max transmissive of blue color filter is higher than 60% in 450nm wavelength than requirement, but within the scope of 515nm to 700nm
All wavelengths be no more than 5%, chromaticity coordinate (xy) of such colour filter in 1931 CIE XYZ colorimetric systems use CIE
Standard D65 light source calculates, and meets 0.134≤x≤0.15 and 0.03≤y≤0.06.In order to realize this target, gold is generallyd use
Category phthalocyanine color be main pigments, such as pigment blue 15: 6, be then equipped with dioxazines pigment, such as pigment Violet 23.
Organic pigment currently used for preparing colour filter mainly has:
It is red: C.I. pigment red 122, C.I. paratonere 177, C.I. paratonere 242, C.I. paratonere 254, and be equipped with suitable
When yellow uitramarine, such as C.I. pigment yellow 13 8, C.I. pigment yellow 13 9, C.I. pigment yellow 150.
Green: C.I. pigment Green 7, C.I. pigment green 36 add specific yellow uitramarine and violet pigment when necessary.
Blue: C.I. pigment blue 15, C.I. pigment blue 15: 3 C.I. pigment blue 15s: 6 C.I. pigment blue 60s etc., when necessary
Add specific yellow uitramarine and violet pigment, such as pigment Violet 23.
It is used to prepare the pigment dispersion of colour filter, can be aqueous, is also possible to non-aqueous.Preparing pigment
After dispersion, it is mixed and made into pigment application liquid with resin, surfactant solution, (squeezes out moulding mixture using certain tool
Bucket coating, rotary coating, spraying, ultrasonic coating, blade coating, intaglio plate coating) it is coated on glass or transparent resin, then
It is prepared into colour filter.
It is being formed as mainly being used in colour filter (Color filiter) with the film shaped resin in dispersible pigment dispersion
Acrylic resin (such as Joncryl678, a kind of styrene that can have acid value high when being developed with alkaline aqueous solution after film
Acrylic copolymeric resin).But in the pigment application liquid formed with dispersible pigment dispersion and high acid value acrylic resin, face
Material is easy to happen cohesion, and it is such agglomerate as the extension of time is increasingly severe, lead to the storage stability of pigment application liquid
Difference, viscosity are increasing.When the granules of pigments cohesion in the raising of pigment application fluid viscosity or dispersion liquid, pigment application liquid is cashed out
Certain thixotropy viscosity, will lead to it and is unevenly coated on substrate, especially in the display colour filter for preparing big picture
When, tone, which is generated, in the center portion of substrate and the coloured film of peripheral portion unevenly becomes apparent from concentration difference.
Colour filter is in pigment application liquid, and pigment content is usually in the range of 5-10%, but it must satisfy dispersion
It is not agglomerated between granules of pigments under state, the low viscosity with 5-20 centipoise (Pas), and there is excellent stable storing
Property.
A kind of paratonere 177 and a small amount of pigment yellow 13 9 are described in patent US2002/0009654A1, blending is dispersed and made
The method of standby red pigment base colour filter；A kind of utilization trimerization s-triazine, amino anthraquinones are described in patent ZL97125486.9
Pigment derivative, formaldehyde, NN- dimethylated propyl diethylenetriamine etc. are condensed, and are then carried out being neutralized into salt with acetic acid, have been prepared one kind
The pigment dispersing agent of yellow, and a series of dispersible pigment dispersions that can be used for preparing colour filter have been prepared using this dispersing agent.
Described in ZL201280006727.X it is a kind of is blended with pigment using pigment derivative, filtered to inhibit crystalline pigment to increase to prepare
The method of color chips dispersible pigment dispersion.It mainly prepares pigment dispersion using Diketopyrrolopyrrolederivative derivative.Specially
It is described in sharp ZL201210201440.4 a kind of for manufacturing the organic pigment dispersing agent of colour filter pigment dispersion, structure
It is one kind by polyoxyalkylene acrylate ester compounds (solvophilic monomer, such as five condensed ethandiol ethyl ether acrylates) and tertiary amine acrylate
The block macromolecular of compound (such as dimethylamino ethyl acrylate) copolymerization.
Summary of the invention
For overcome the deficiencies in the prior art, the purpose of the present invention is to provide a kind of pigment dispersing agents and application thereof.
In order to achieve the above-mentioned object of the invention, the invention adopts the following technical scheme:
The pigment dispersing agent as shown in general formula (I) is light yellow, orange-yellow or even brown solid powder substance:
Wherein: X is substituted or unsubstituted phenylamino, amino anthraquinones, and aminoalkyl naphthalimide or naphthalene nucleus replace aminoalkyl
Naphthalimide；
Y is the aliphatic at least with the carbon atom number 2-10 of an amino, alicyclic or heteroalicyclic polyamines base；
N is the integer of 2-6；
R1It is halogen, nitro, substituted amido.
X is aminoalkyl naphthalimide or naphthalene nucleus replaces aminoalkyl naphthalimide, and specifically: amino-ethyl naphthoyl is sub-
Amine, 3- aminopropyl naphthalimide, 4- aminobutyl naphthalimide, the chloro- 2- amino-ethyl naphthalimide of 4-, 4- nitro -3- ammonia
Base propyl naphthalimide, 4- benzamido -2- amino-ethyl naphthalimide, 4- caprinoyl amido -3- aminopropyl naphthalimide；
X is substituted-amino anthraquinone, specifically 4- acetylaminohydroxyphenylarsonic acid 1- amino anthraquinones, 4- benzamido -1- amino anthracene
Quinone, 4- butyrylamino -1- amino anthraquinones, 4- propionamido -1- amino anthraquinones, 4- hexanoyl amino -1- amino anthraquinones, penta ammonia of 4- second
Base -1- amino anthraquinones；
Y is the group of at least aliphatic polyamine of the carbon atom number 2-30 with an amino, specifically N, N- bis-
Methyl ethylenediamine, N, N- dimethylated propyl diethylenetriamine, N, N- diamine dimethyl butyrate, N, N- dimethyl-penten diamines, N, N- dimethyl oneself two
Amine, N, N- diethyl butanediamine, N, N- dipropyl butanediamine, N, N- dipropyl hexamethylene diamine, N, N- diethyl pentanediamine.
Dispersible pigment dispersion, comprising: pigment, above-mentioned pigment dispersing agent, film-forming resin and liquid medium, pigment are red face
Material, then specifically pigment is C.I. paratonere 177；
Pigment dispersing agent and pigment add the ratio of the pigment dispersing agent of 0.5-50 parts of weight according to every 100 parts of weight pigment
Mixing.
Dispersible pigment dispersion is used to manufacture the purposes of red color filter, and pigment point is used specifically on colour filtering chip basic board
Dispersion liquid forms coloring graphic pattern.
Above-mentioned pigment dispersing agent is that aminoalkyl naphthalimide reacts gained compound with trichloro-triazine, is contained in structure
Have more rigid aromatic ring structure, amide structure and amino, can by hydrogen bond, pi bond, dispersion force, dipolar forces, hydrophobic effect with
Pigment is firmly combined, and amino therein forms positively charged pigment particles in aqueous solution, utilizes electrostatic repulsion and dispersing agent
Effect of steric hindrance prevent dispersible pigment dispersion from agglomerating.Therefore, the dispersible pigment dispersion prepared using the pigment dispersing agent, structure are viscous
Property reduce, storage stability improve, it is suppressed that the thickening gelation of pigment dispersion.
Specific embodiment:
Below by way of specific embodiment, the present invention is further described.
Embodiment 1: the preparation of compound P-1:
(in P-1, Y=N, N- dimethyl-ethylenediamine, n=2, X=amino-ethyl naphthalimide)
Preparation method: by 2mol 2- amine ethyl -1,8- naphthalimide and 1mol trichloro-triazine in such as dichloro-benzenes, nitro
In the atent solvent of benzene, 2-6h is reacted at 70-160 DEG C, and adds 1mol N, N- dimethyl-ethylenediamine, at 150-180 DEG C
It reacts 3-4 hours and is made under reaction condition.
The Structural Identification of compound P-1: elemental analysis result surveys (theory): C:65.42 (65.31), H:5.13
(5.17), (19.58) N:19.60.
1H-NMR (DMSO), it is as a result as follows: δ=7.99 (d, 4H)；δ=7.92 (d, 4H)；δ=7.66 (d, 4H)；δ=
4.09 (s, 3H)；δ=3.43 (t, 4H)；δ=3.36 (t, 4H)；δ=3.16 (t, 2H)；δ=2.59 (t, 2H)；δ=2.27 (s,
6H)。
On the basis of compound P-1, increases substituent group, compound P-2, P-3, P-4, P-5, P-6, P-7 can be obtained,
Structural formula is as follows:
Embodiment 2: the preparation of compound M-1:
(in M-1, Y=N, N- dimethyl-ethylenediamine, n=2, X=aniline)
Preparation method: by the way that 1mol 2- amine ethyl -1,8- naphthalimide, 1mol aniline and 1mol trichloro-triazine exist
In such as dichloro-benzenes, nitrobenzene atent solvent, 2-6h is reacted at 70-160 DEG C, and adds 1mol N, N- diamine dimethyl butyrate,
It reacts 3-4 hours and is made under 150-180 DEG C of reaction condition.
The elemental analysis result of M-1 surveys (theory): C:65.37 (65.31), H:5.63 (5.68), N:22.55
(22.57)。
1H-NMR (DMSO), it is as a result as follows: δ=7.94 (d, 2H)；δ=7.91 (d, 2H)；δ=7.56 (d, 2H)；δ=
6.56-7.04 (d, 5H)；δ=4.04 (s, 3H)；δ=3.44 (t, 2H)；δ=3.36 (t, 2H)；δ=3.16 (t, 2H)；δ=
2.59 (t, 2H)；δ=2.27 (s, 6H).
On the basis of compound M-1, increases substituent group, compound M-2 to M--7 can be obtained, structural formula is as follows:
Embodiment 3: the preparation of compound Q -1:
(in Q-1, Y=N, N- dimethylhexanediamine, n=2, X=1- amino anthraquinones)
Compound Q -1, can be by by 1mol 2- amine ethyl -1,8- naphthalimide, 1mol amino anthraquinones and 1mol trichlorine
S-triazine reacts 2-6h in the atent solvents such as such as dichloro-benzenes, nitrobenzene at 70-160 DEG C, and adds 1mol N, N- diformazan
Base hexamethylene diamine is reacted 3-4 hours under 150-180 DEG C of reaction condition and is made.
The elemental analysis result of Q-1 surveys (theory): C:68.42 (68.61), H:5.63 (5.61), N:16.43
(16.41)。
1H-NMR (DMSO), it is as a result as follows: δ=7.94 (m, 4H)；δ=7.80 (d, 2H)；δ=7.55-7.57 (m, 4H)；
δ=7.30 (s, 1H)；δ=7.16 (s, 1H)；δ=6.75 (s, 1H)；δ=4.04 (s, 3H)；δ=3.04 (t, 2H)；δ=2.36
(t, 2H)；δ=2.27 (s, 6H)；δ=1.29-1.52 (m, 8H)
On the basis of compound Q -1, increases substituent group, compound M-2 to M--7 can be obtained, structural formula is as follows:
Embodiment 4
It is formulated according to shown in table 1, in acrylic resin soln (by methacrylic acid/butyl acrylate/styrene/propylene
Sour hydroxyl ethyl ester is polymerized with 25/50/15/10 molar ratio, molecular weight 12000, solid content 30%) in, paratonere 177 is added
(P.R 177) and above-mentioned dispersing agent P1 and solvent ethylene glycol ether acetate (EGEEAC), after premixing, with sand mill
(nanoscale recycles sand millRS is resistance to speed) grinding distribution 5 hours, 5 micrometer glass fiber filters filtering, from abrasive media
Separate to obtain red base pigment dispersion.
Embodiment 5-8
Successively with the dispersing agent P3, M5, Q2 of equivalent, Q4 is instead of obtaining the red of embodiment 2-5 after the dispersing agent P1 of embodiment
Color base pigment dispersion.
Comparative example 1
Compared using the dispersing agent P1 in commercially available yellow uitramarine derivative disperser (abbreviation YD) alternative embodiment 1
The red base pigment dispersion of example 1.
Comparative example 2
Compared using the dispersing agent P1 in commercially available blue pigment derivative disperser (abbreviation BD) alternative embodiment 1
The red base pigment dispersion of example 2.
The formula table of table 1 embodiment 4-8 and comparative example 1-2 (numerical value is indicated with " parts by weight ")
| 4 | 5 | 6 | 7 | 8 | Comparative example 1 | Comparative example 1 | |
| Pigment 177 | 20 | 20 | 20 | 20 | 20 | 20 | 20 |
| P1 | 2 | - | - | - | - | - | - |
| P3 | - | 2 | - | - | - | - | - |
| M5 | - | - | 2 | - | - | - | |
| Q2 | - | - | - | 2 | - | - | - |
| Q4 | - | - | - | - | 2 | - | - |
| YD | - | - | - | - | 2 | - | |
| BD | - | - | - | - | - | - | 2 |
| Acrylic resin soln | 50 | 50 | 50 | 50 | 50 | 50 | 50 |
| EGEEAC | 28 | 28 | 28 | 28 | 28 | 28 | 28 |
| It is total | 100 | 100 | 100 | 100 | 100 | 100 | 100 |
9 performance test of embodiment
1, the dispersible pigment dispersion of embodiment 4-8 and comparative example 1-2 are coated on the glass substrate with spin coater respectively,
Coating thickness is controlled after 2.5um, natural drying, measures the maximum transmission rate and maximum absorption wavelength of film.
2, prepared dispersible pigment dispersion is fitted into shake flask, is sealed, stored one month at room temperature, measure its viscosity
Variation, the results are shown in Table 2.
3, the distribution of particles of pigment uses Malvern nano particle size, zeta potentiometer (Zs90, Malvern company in dispersion liquid
Production) measurement, respectively measure dispersion liquid before placement with place one month after particle diameter distribution.It the results are shown in Table 3.
The light projection performance and storage stability of the red base colour filter pigment dispersion of table 2
It can be seen that: the dispersible pigment dispersion prepared using the pigment dispersing agent, structural viscosity are reduced, and storage stability improves.
The red base colour filter pigment dispersion particle diameter distribution of table 3
As it can be seen that preventing the cohesion of dispersible pigment dispersion using the pigment dispersing agent, there is lesser partial size.
Claims (8)
1. the pigment dispersing agent as described in general formula (I):
Wherein: X is substituted or unsubstituted phenylamino, amino anthraquinones, and aminoalkyl naphthalimide and naphthalene nucleus replace aminoalkyl naphthoyl
Imines；
Y is the aliphatic at least with the carbon atom number 2-10 of an amino, alicyclic or heteroalicyclic polyamines base；
N is the integer of 2-6；
R1 is halogen, nitro, substituted amido.
2. pigment dispersing agent described in claim 1, which is characterized in that in formula (I):
X be aniline, open-chain crown ether, parachloroanilinum, to ethyl aniline, m-chloroaniline, m-toluidine, paranitroanilinum, right
Acetylaminoaniline, meta nitro aniline, to benzamido aniline；
Alternatively, X is amino-ethyl naphthalimide, 3- aminopropyl naphthalimide, 4- aminobutyl naphthalimide, the chloro- 2- ammonia of 4-
Base ethyl naphthalimide, 4- nitro -3- aminopropyl naphthalimide, 4- benzamido -2- amino-ethyl naphthalimide, the 4- last of the ten Heavenly stems
Amide groups -3- aminopropyl naphthalimide；
Alternatively, X is 4- acetylaminohydroxyphenylarsonic acid 1- amino anthraquinones, 4- benzamido -1- amino anthraquinones, 4- butyrylamino -1- amino anthracene
Quinone, 4- propionamido -1- amino anthraquinones, 4- hexanoyl amino -1- amino anthraquinones, penta amino -1- amino anthraquinones of 4- second:
Y is N, N- dimethyl-ethylenediamine, N, N- dimethylated propyl diethylenetriamine, N, N- diamine dimethyl butyrate, N, N- dimethyl-penten diamines, N,
N- dimethylhexanediamine, N, N- diethyl butanediamine, N, N- dipropyl butanediamine, N, N- dipropyl hexamethylene diamine, N, N- diethyl
Pentanediamine, 1- (3- aminocarbonyl propyl) piperidines.
3. the dispersible pigment dispersion based on pigment dispersing agent described in claim 1, comprising: pigment, pigment dispersing agent, film-forming resin
And liquid medium, pigment are red pigments.
4. dispersible pigment dispersion according to claim 3, it is characterised in that pigment dispersing agent and pigment are according to every 100 parts of weight
Pigment adds the ratio mixing of the pigment dispersing agent of 0.5-50 parts of weight.
5. dispersible pigment dispersion according to claim 3, which is characterized in that pigment is C.I. paratonere 177.
6. the purposes that dispersible pigment dispersion as claimed in claim 3 is used to manufacture red color filter.
7. the purposes that dispersible pigment dispersion as claimed in claim 3 is used to manufacture red color filter, which is characterized in that in colour filter chip base
Coloring graphic pattern is formed using dispersible pigment dispersion on plate.
8. prepared colour filter described in claim 7.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112347685A (en) * | 2020-11-30 | 2021-02-09 | 江南大学 | Color fiber two-dimensional color mixing space grid model and grid point array color matrix construction method and application thereof |
| CN115247000A (en) * | 2022-07-27 | 2022-10-28 | 上海百艳实业有限公司 | Novel pigment and preparation method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03258859A (en) * | 1990-03-07 | 1991-11-19 | Mitsubishi Kasei Corp | Water-insoluble naphthalic acid imide-based pigment |
| CN103193765A (en) * | 2013-04-18 | 2013-07-10 | 苏州大学 | 1,8-naphthalene imide derivative and preparation method and application thereof |
| CN109020951A (en) * | 2018-08-24 | 2018-12-18 | 大连理工大学 | The naphthalimide analog derivative and its synthetic method that replace Cyanuric Chloride containing three and application |
-
2018
- 2018-12-16 CN CN201811540571.9A patent/CN109554004B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03258859A (en) * | 1990-03-07 | 1991-11-19 | Mitsubishi Kasei Corp | Water-insoluble naphthalic acid imide-based pigment |
| CN103193765A (en) * | 2013-04-18 | 2013-07-10 | 苏州大学 | 1,8-naphthalene imide derivative and preparation method and application thereof |
| CN109020951A (en) * | 2018-08-24 | 2018-12-18 | 大连理工大学 | The naphthalimide analog derivative and its synthetic method that replace Cyanuric Chloride containing three and application |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112347685A (en) * | 2020-11-30 | 2021-02-09 | 江南大学 | Color fiber two-dimensional color mixing space grid model and grid point array color matrix construction method and application thereof |
| CN112347685B (en) * | 2020-11-30 | 2021-08-10 | 江南大学 | Construction and application of color fiber two-dimensional color mixing space grid model and grid point array chromatogram |
| WO2022110589A1 (en) * | 2020-11-30 | 2022-06-02 | 江南大学 | Colored-fiber two-dimensional color mixing space grid model and grid point array color matrix construction method thereof and application thereof |
| CN115247000A (en) * | 2022-07-27 | 2022-10-28 | 上海百艳实业有限公司 | Novel pigment and preparation method thereof |
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