CN105732404A - Binaphthalenediol compound and application thereof - Google Patents
Binaphthalenediol compound and application thereof Download PDFInfo
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- CN105732404A CN105732404A CN201610192043.3A CN201610192043A CN105732404A CN 105732404 A CN105732404 A CN 105732404A CN 201610192043 A CN201610192043 A CN 201610192043A CN 105732404 A CN105732404 A CN 105732404A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C291/00—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00
- C07C291/02—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds
- C07C291/04—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds containing amino-oxide bonds
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
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- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
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Abstract
The invention relates to a binaphthalenediol compound and an application thereof. The binaphthalenediol compound is obtained through proper structural modification of a parent compound 1,1'-binaphthalenediol; and the obtained binaphthalenediol compound can improve the dispersity and fluidity of organic pigment without influencing the tinting strength of the organic pigment. Therefore, the binaphthalenediol compound provided by the invention can be used as a dispersing agent of the organic pigment.
Description
Technical field
The present invention relates to a kind of Binaphthol compounds and application thereof, specifically, relate to a kind of Binaphthol compounds and
It is as the application of organic pigment dispersant.
Background technology
Organic pigment is the crystalline solid with packing of molecules, exists with fine particle (general granularity is 0.01 μm～0.1 μm),
Primary partical owing to generating has higher surface free energy, and it has strong adelphotaxy to each other, forms set
Particle, and particle is insoluble in most of solvent, difficulties in dispersion, big particle also makes the bin stability of system be deteriorated.One
As in coating or ink the granularity of organic pigment at least to reach 0.05 μm～0.15 μm.Therefore, before making pigment, pigment particles is made
Miniaturization, Control granularity scope, and reach the purpose of stable dispersion.
Dispersion pigment frequently with add dispersant method, dispersant with monolayer or polymolecular layer coated pigment particle surface,
To change the surface polarity of particle so that it is with medium, there is the more preferable compatibility.Conventional pigment dispersing agent mainly has: inorganic face
Material dispersant, polymer pigment dispersant and surfactant-based pigment dispersing agent etc..
Surfactant-based pigment dispersing agent mainly has: the amine salt of fatty amine or derivatives thereof or quaternary ammonium salt, and it can reduce pigment particles
Improve pigment-dispersing, the preparation process of organic pigment adds some amine salt or ammonium salt can improve pigment dispersibility and
Fluidity (Jie Wu, Li-Min Wang, Ping Zhao, FengWang, Gui-fengWang, A new type of quaternary
mmonium salt containing siloxane group and used as favorable dispersant in the surface treatment
of C.I.pigment red 170,Progress in Organic Coatings 2008,63,189–194.)。
Though but existing surfactant-based pigment dispersing agent can improve dispersibility and the fluidity of organic pigment, but it is to organic
The coloured light of pigment has certain impact, and can reduction pigmenting power in various degree.
Dispersibility and the fluidity of organic pigment can be improved in consideration of it, develop, the most not affect tinting strength, tinting power organic of organic pigment
Pigment dispersing agent becomes the technical issues that need to address of the present invention.
Summary of the invention
The present inventor it has been investigated that: with 1,1 '-binaphthol (BINOL) for parent compound, it is carried out suitably
Structural modification after obtain a kind of Binaphthol compounds.Obtained Binaphthol compounds can improve organic pigment
Dispersibility and fluidity, the most do not affect the tinting strength, tinting power of organic pigment.
Therefore, it is an advantage of the invention to provide the Binaphthol compounds of a kind of novel structure, described dinaphthalene two
Phenolic compound is formula I a or compound shown in I b:
In formula, R1～R6It is each independently selected from: C1～C8One in the alkyl of straight or branched, a is the integer of 1～10, and b is
The integer of 1～10, X is halogen (F, Cl, Br or I).
Another object of the present invention is, discloses the one of above-mentioned Binaphthol compounds (compound shown in formula I a or I b)
Purposes: i.e. shown in formula I a or I b, compound is as the application of organic pigment dispersant.
A further object of the invention is, it is provided that one prepares Binaphthol compounds of the present invention (formula I a or I b institute
Show compound) method, having main steps that of described method: first, by Binaphthol (compound shown in formula II) with corresponding
Halohydrin (Y (CH2)aOH is or/and Y (CH2)bOH) reaction, obtains corresponding intermediate A (compound shown in formula III)；
Then, the intermediate A of gained is reacted with secondary amine, obtain corresponding intermediate B (compound shown in formula IV)；Finally, in inciting somebody to action
Mesosome B reacts with alkyl halide or oxidized for intermediate B dose (fat of peroxide or aromatic carboxylic acids) is aoxidized, and obtains object
(compound shown in corresponding quaternary ammonium salt or amine oxide, formula I a or I b):
Wherein, Y is halogen (F, Cl, Br or I), and the definition of a with b is identical with described previously.
Detailed description of the invention
In one optimal technical scheme of the present invention, R1～R6It is each independently selected from: C1～C8One in the alkyl of straight or branched.
In presently preferred technical scheme, X is chlorine (Cl), bromine (Br) or iodine (I).
In another optimal technical scheme of the present invention, a is the integer of 3～8, and b is the integer of 3～8, and a=b.
In another optimal technical scheme of the present invention, described organic pigment is azo organic pigment and heterocyclic organic pigment.
Below by embodiment, the present invention is further elaborated, and its purpose is only that and is best understood from present disclosure.Therefore,
The cited case is not intended to protection scope of the present invention.
Embodiment 1
The preparation of compound shown in formula I a-1:
(1) at ambient temperature, by 4.50g (15.7mmol) Binaphthol (compound shown in formula II), triphenylphosphine (12.37g,
During 47.10mmol) oxolane processed with drying is placed in the reactor with stirring and heater, stirring；
To be made up of ethylene bromohyrin (47.10mmol) and 9.35mL (47.10mmol) diisopropyl azodiformate (DIAD)
Mixture add in above-mentioned reactor, charging is finished, and is heated to reflux state and keeps 7 hours at reflux state, cooling
To room temperature, reduce pressure and remove reaction dissolvent, residue by silicagel column column chromatography (eluant: dichloromethane: ether is 1: 1 (v/v)),
Obtaining 5g colorless oil (compound shown in formula III-1), productivity is 65%；
1H NMR(400MHz,CDCl3): δ (ppm) 8.00 (d, J=8.9Hz, 2H), 7.91 (d, J=8.1Hz, 2H), 7.45 (d,
J=9.0Hz, 2H), 7.38 (t, J=8.1Hz, 2H), 7.29 (m, 2H), 7.17 (d, J=8.5Hz, 2H), 4.23 (m, 4H), 3.26
(m,4H).
(2) under condition of ice bath, dry oxolane (20mL) is equipped with three mouthfuls of sodium hydride (19.2mmol)
In flask, stirring, then by dimethylamine ((CH3)2NH) oxolane (30mL) solution of (16.0mmol) be slowly added dropwise to
In above-mentioned reactant liquor, drip complete holding reaction 10 minutes, then be added dropwise to by compound shown in formula III (8.0mmol) and tetrahydrochysene
The mixture that furan (10mL) forms, is warming up to room temperature.TLC monitors reaction, treats that raw material point disappears substantially, with water (20mL)
Cancellation is reacted.Dichloromethane carries out extracting three times, and saturated nacl aqueous solution is washed till neutrality, and anhydrous sodium sulfate is dried, and filters, will
Filtrate concentrates, and carries out silica gel column chromatography separating-purifying (eluant: dichloromethane: ether is 1: 1 (v/v)), obtains 5.5g
Faint yellow solid (compound shown in formula IV-1), productivity is 93%.
1H NMR(400MHz,CDCl3): δ (ppm) 8.02 (d, J=8.9Hz, 2H), 7.88 (d, J=8.1Hz, 2H), 7.45 (d,
J=9.0Hz, 2H), 7.39 (t, J=8.1Hz, 2H), 7.28 (m, 2H), 7.17 (d, J=8.5Hz, 2H), 4.21 (m, 4H), 2.85
(s,12H),2.76(m,4H).
(3) by compound shown in formula IV (5.0mmol), DMF (DMF) is placed in reactor, the most again
In this reaction, add iodomethane (5.1mmol), continue to be stirred at room temperature.TLC monitors reaction, treats that raw material point disappears, stops stirring
Mixing, filter, filter cake, through recrystallization (DMF), obtains 5.6 grams of faint yellow solids (compound shown in formula I a-1), productivity 95%.
Nuclear magnetic data:
1H NMR(400MHz,CDCl3): δ (ppm) 8.01 (d, J=8.8Hz, 2H), 7.89 (d, J=8.2Hz, 2H), 7.47 (d,
J=8.9Hz, 2H), 7.31 (t, J=8.1Hz, 2H), 7.30 (m, 2H), 7.18 (d, J=8.7Hz, 2H), 4.28 (m, 4H),
2.30(s,18H),4.77(m,4H).
Embodiment 2
The preparation of compound shown in formula I b-1:
Compound shown in formula IV-1 (5.0mmol) and dichloromethane are placed in reactor, are stirred at room temperature, add in this reactor
Entering the metachloroperbenzoic acid (mCPBA, 30.0mmol) of three equivalents, continue to be stirred at room temperature, TLC monitors reaction, treats raw material
Point disappears, then adds solid carbonic acid potassium or sodium sulfite stirring in described reactor, to starch potassium iodide paper no longer variable color,
Cancellation reaction (sodium hydrate aqueous solution), decompression be spin-dried for solvent, crude reaction is carried out silica gel column chromatography separating-purifying (eluant:
Dichloromethane: methanol=5: 1 (v/v)), obtain 5.7 grams of faint yellow solids (compound shown in formula I b-1), productivity 95%.
1H NMR(400MHz,CDCl3): δ (ppm) 8.02 (d, J=8.9Hz, 2H), 7.88 (d, J=8.1Hz, 2H), 7.45 (d,
J=9.0Hz, 2H), 7.39 (t, J=8.1Hz, 2H), 7.28 (m, 2H), 7.17 (d, J=8.5Hz, 2H), 4.36 (m, 4H), 3.02
(s,12H),2.92(m,4H)。
With reference to the preparation method of embodiment 1 and 2, and do the replacement of corresponding reagent, it is also possible to synthesis obtains listed by Tables 1 and 2
Compound:
Table 1 quarternary ammonium salt compound
Table 2 amine oxide compounds
Compounds I a-2
1H NMR(400MHz,CDCl3): δ (ppm) 8.01 (d, J=8.8Hz, 2H), 7.89 (d, J=8.2Hz, 2H), 7.47 (d,
J=8.9Hz, 2H), 7.31 (t, J=8.1Hz, 2H), 7.30 (m, 2H), 7.18 (d, J=8.7Hz, 2H), 4.28 (m, 6H),
2.30(s,18H),2.77(m,6H).
Compounds I a-3
1H NMR(400MHz,CDCl3): δ (ppm) 8.01 (d, J=8.8Hz, 2H), 7.89 (d, J=8.2Hz, 2H), 7.47 (d,
J=8.9Hz, 2H), 7.31 (t, J=8.1Hz, 2H), 7.30 (m, 2H), 7.18 (d, J=8.7Hz, 2H), 4.28 (m, 8H),
2.30(s,18H),4.77(m,8H).
Compounds I a-4
1H NMR(400MHz,CDCl3): δ (ppm) 8.01 (d, J=8.8Hz, 2H), 7.89 (d, J=8.2Hz, 2H), 7.47 (d,
J=8.9Hz, 2H), 7.31 (t, J=8.1Hz, 2H), 7.30 (m, 2H), 7.18 (d, J=8.7Hz, 2H), 4.28 (m, 10H),
2.30(s,18H),4.77(m,10H).
Compounds I a-5
1H NMR(400MHz,CDCl3): δ (ppm) 8.01 (d, J=8.8Hz, 2H), 7.89 (d, J=8.2Hz, 2H), 7.47 (d,
J=8.9Hz, 2H), 7.31 (t, J=8.1Hz, 2H), 7.30 (m, 2H), 7.18 (d, J=8.7Hz, 2H), 4.28 (m, 12H),
2.30(s,18H),4.77(m,12H).
Compounds I a-6
1H NMR(400MHz,CDCl3): δ (ppm) 8.01 (d, J=8.8Hz, 2H), 7.89 (d, J=8.2Hz, 2H), 7.47 (d,
J=8.9Hz, 2H), 7.31 (t, J=8.1Hz, 2H), 7.30 (m, 2H), 7.18 (d, J=8.7Hz, 2H), 4.28 (m, 14H),
2.30(s,18H),4.77(m,14H).
Compounds I a-7
1H NMR(400MHz,CDCl3): δ (ppm) 8.01 (d, J=8.8Hz, 2H), 7.89 (d, J=8.2Hz, 2H), 7.47 (d,
J=8.9Hz, 2H), 7.31 (t, J=8.1Hz, 2H), 7.30 (m, 2H), 7.18 (d, J=8.7Hz, 2H), 4.28 (m, 16H),
2.30(s,18H),4.77(m,16H).
Compounds-b-2
1H NMR(400MHz,CDCl3): δ (ppm) 8.02 (d, J=8.9Hz, 2H), 7.88 (d, J=8.1Hz, 2H), 7.45 (d,
J=9.0Hz, 2H), 7.39 (t, J=8.1Hz, 2H), 7.28 (m, 2H), 7.17 (d, J=8.5Hz, 2H), 4.36 (m, 6H), 3.02
(s,12H),3.92(m,6H)。
Compounds-b-3
1H NMR(400MHz,CDCl3): δ (ppm) 8.02 (d, J=8.9Hz, 2H), 7.88 (d, J=8.1Hz, 2H), 7.45 (d,
J=9.0Hz, 2H), 7.39 (t, J=8.1Hz, 2H), 7.28 (m, 2H), 7.17 (d, J=8.5Hz, 2H), 4.36 (m, 8H), 3.02
(s,12H),3.92(m,8H)。
Compounds-b-4
1H NMR(400MHz,CDCl3): δ (ppm) 8.02 (d, J=8.9Hz, 2H), 7.88 (d, J=8.1Hz, 2H), 7.45 (d,
J=9.0Hz, 2H), 7.39 (t, J=8.1Hz, 2H), 7.28 (m, 2H), 7.17 (d, J=8.5Hz, 2H), 4.36 (m, 10H),
3.02(s,12H),3.92(m,10H)。
Compounds-b-5
1H NMR(400MHz,CDCl3): δ (ppm) 8.02 (d, J=8.9Hz, 2H), 7.88 (d, J=8.1Hz, 2H), 7.45 (d,
J=9.0Hz, 2H), 7.39 (t, J=8.1Hz, 2H), 7.28 (m, 2H), 7.17 (d, J=8.5Hz, 2H), 4.36 (m, 12H),
3.02(s,12H),3.92(m,12H)。
Compounds-b-6
1H NMR(400MHz,CDCl3): δ (ppm) 8.02 (d, J=8.9Hz, 2H), 7.88 (d, J=8.1Hz, 2H), 7.45 (d,
J=9.0Hz, 2H), 7.39 (t, J=8.1Hz, 2H), 7.28 (m, 2H), 7.17 (d, J=8.5Hz, 2H), 4.36 (m, 14H),
3.02(s,12H),3.92(m,14H)。
Compounds-b-7
1H NMR(400MHz,CDCl3): δ (ppm) 8.02 (d, J=8.9Hz, 2H), 7.88 (d, J=8.1Hz, 2H), 7.45 (d,
J=9.0Hz, 2H), 7.39 (t, J=8.1Hz, 2H), 7.28 (m, 2H), 7.17 (d, J=8.5Hz, 2H), 4.36 (m, 16H),
3.02(s,16H),3.92(m,14H)。
Embodiment 3 (performance test)
Pigment fluidity is tested
The Binaphthol compounds of 1.5 parts of present invention synthesis is dissolved in the water, under vigorous stirring, is added to containing 30 parts of pigment
In the slurry of 800 parts of pigment of red PR57:1 (Hangzhou Baihe Clariant Pigments Co., Ltd.), add in 10 minutes.Finish,
In 20 minutes, it is warming up to 75 DEG C, is incubated 10 minutes, adjust pH=7.3-7.5 with hydrochloric acid, be incubated 15 minutes, at 90 DEG C, dry
Dry 12 hours, obtain pigment sample.
Weigh above-mentioned pigment sample 500mg (accurately to 0.001g), at room temperature extract 1ml varnish, pigment with syringe
Being placed on the ground glass of flat-grinding machine with varnish, be slurred with inking cutter, mill base divides be placed on from glass surface center radius at 4
At 1/4th, lever bracket adds 1 kilogram of counterweight and is ground with 100 turns, grind 2 times, obtain mill base.
Draw an above-mentioned mill base of lattice with ink tube, slurry inking cutter remaining in pipe end is scraped off, keep ink slurry to put down with the mouth of pipe, then will
Blotting water pipe built-in slurry extrusion, the Circular glass center being placed in fixed bin, and with inking cutter by careful for the excess ink of blotting water pipe
Scrape and smear to the greatest extent in another block Circular glass center, upper block sheet glass is put on the glass of fixed bin, make two centers, part be connected,
While pressing counterweight, start clock, after 15 minutes, remove counterweight, with the transparent circle measured and extend after ink slurry pressurized measured by chi
Shape diameter, is measured by orthogonal directions, averages for twice, if twice measurement result difference more than 2mm, then should reform.
Result is shown in table 3.
Pigment dispersion stability is tested
The Binaphthol compounds taking 0.1 part of present invention synthesis is dissolved in 50 parts of ethanol, is warming up to 75 DEG C, lower point of strong agitation
Jia Ru 2 parts of PV19 (Hangzhou Baihe Clariant Pigments Co., Ltd.), PR170 (Hangzhou Baihe Clariant Pigments Co., Ltd.)
With PY74 (Hangzhou Baihe Clariant Pigments Co., Ltd.) dry powder, transfer to 100ml tool plug measuring tank after stirring 1 hour, stand
12 hours.Below liquid level, at 1cm, draw 0.5ml liquid, be diluted to 100ml, saturating with UV755B spectrophotometric determination
Cross rate T.With the transmitance numerical computations dispersion stabilization DE% of maximum absorption wave strong point (by DE%=(1-T) X100%, T
The transmitance of maximum absorption wave strong point), concrete outcome is shown in Table 3.
Pigmenting power is tested
On seven blocks of sheet glass, respectively weigh standard chalk 2g respectively, then weigh the Binaphthol class of 50mg present invention synthesis respectively
Compound, as the mill base of dispersant, is fully mixed well with inking cutter respectively, is scraped sample.Carrying out tinting strength, tinting power evaluation with colour photometer, result is shown in
Table 3.
The performance of table 3 pigment
Continued 3
#For existing organic pigment dispersant
As shown in Table 3, using Binaphthol compounds of the present invention as organic pigment dispersant, either pigment disperses
Stability and pigment fluidity, or pigmenting power is superior to existing organic pigment dispersant (1631 quaternary ammonium salt).
Claims (5)
1. a Binaphthol compounds, described Binaphthol compounds is formula I a or compound shown in I b:
In formula, R1～R6It is each independently selected from: C1～C8One in the alkyl of straight or branched, a is the integer of 1～10, and b is
The integer of 1～10, X is halogen.
2. Binaphthol compounds as claimed in claim 1, it is characterised in that wherein R1～R6It is each independently selected from:
C1～C8One in the alkyl of straight or branched.
3. Binaphthol compounds as claimed in claim 2, it is characterised in that wherein a is the integer of 3～8, b be 3～
The integer of 8, and a=b.
4. the Binaphthol compounds as described in any one in claims 1 to 3 is as the application of organic pigment dispersant.
Apply the most as claimed in claim 4, it is characterised in that wherein said organic pigment is azo organic pigment and heterocycle
Class organic pigment.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109796369A (en) * | 2019-01-21 | 2019-05-24 | 广东好顺欧迪斯科技股份有限公司 | The application of 1,1 '-union -2-naphthol derivatives and its fluorescent dye as water paint |
| WO2022085509A1 (en) * | 2020-10-23 | 2022-04-28 | 日本化薬株式会社 | Colored liquid, colored-liquid set, recording medium, and coloring method |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE929611C (en) * | 1953-05-17 | 1955-06-30 | Knoll Ag | Process for the production of quaternary salts of basic ethers of dinaphthyl |
| CN1264699A (en) * | 1999-12-24 | 2000-08-30 | 厦门大学 | High-optical-purity dinaphthdiol monomenthyl carbonate and its preparing process |
| CN102504573A (en) * | 2011-10-10 | 2012-06-20 | 杭州百合科莱恩颜料有限公司 | Naphthol AS organic azo pigment and its synthesis method |
| CN103804631A (en) * | 2014-02-19 | 2014-05-21 | 中国科学技术大学 | Polyketide with quaternized side chain and preparation method thereof as well as anion-exchange membrane |
-
2016
- 2016-03-30 CN CN201610192043.3A patent/CN105732404B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE929611C (en) * | 1953-05-17 | 1955-06-30 | Knoll Ag | Process for the production of quaternary salts of basic ethers of dinaphthyl |
| CN1264699A (en) * | 1999-12-24 | 2000-08-30 | 厦门大学 | High-optical-purity dinaphthdiol monomenthyl carbonate and its preparing process |
| CN102504573A (en) * | 2011-10-10 | 2012-06-20 | 杭州百合科莱恩颜料有限公司 | Naphthol AS organic azo pigment and its synthesis method |
| CN103804631A (en) * | 2014-02-19 | 2014-05-21 | 中国科学技术大学 | Polyketide with quaternized side chain and preparation method thereof as well as anion-exchange membrane |
Non-Patent Citations (1)
| Title |
|---|
| HUANG, XIAOBO等: "Polymer-based fluorescence sensors incorporating chiral binaphthyl and benzo[2,1,3]thiadiazole moieties for Hg2+ detection", 《JOURNAL OF POLYMER SCIENCE, PART A: POLYMER CHEMISTRY》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109796369A (en) * | 2019-01-21 | 2019-05-24 | 广东好顺欧迪斯科技股份有限公司 | The application of 1,1 '-union -2-naphthol derivatives and its fluorescent dye as water paint |
| WO2022085509A1 (en) * | 2020-10-23 | 2022-04-28 | 日本化薬株式会社 | Colored liquid, colored-liquid set, recording medium, and coloring method |
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| Publication number | Publication date |
|---|---|
| CN105732404B (en) | 2017-08-22 |
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Address after: No. 1888, Jingwu Road, Linjiang Industrial Park, Xiaoshan District, Hangzhou, Zhejiang 311,228 Patentee after: Hangzhou Baihe Huibaihe Pigment Co.,Ltd. Patentee after: EAST CHINA University OF SCIENCE AND TECHNOLOGY Address before: No. 1888, Jingwu Road, Linjiang Industrial Park, Xiaoshan District, Hangzhou, Zhejiang 311,228 Patentee before: HANGZHOU BAIHE KELAIEN PIGMENT CO.,LTD. Patentee before: EAST CHINA University OF SCIENCE AND TECHNOLOGY |
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