CN107057054B - Quinacridone polyether derivatives and preparation method and application thereof - Google Patents
Quinacridone polyether derivatives and preparation method and application thereof Download PDFInfo
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- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- 239000004721 Polyphenylene oxide Substances 0.000 title claims abstract description 20
- 229920000570 polyether Polymers 0.000 title claims abstract description 20
- 239000000049 pigment Substances 0.000 claims abstract description 35
- 125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 12
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims abstract description 10
- -1 quinacridone compound Chemical class 0.000 claims abstract description 9
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 8
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- WIWJFWANKMRGGS-UHFFFAOYSA-N 3,4-dimethyl-1,6-dioxecane-2,5,7,10-tetrone Chemical compound C1(CCC(=O)OC(C(C(C(=O)O1)C)C)=O)=O WIWJFWANKMRGGS-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000000654 additive Substances 0.000 claims abstract description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000000576 coating method Methods 0.000 claims abstract description 4
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 4
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 3
- BFWYZZPDZZGSLJ-UHFFFAOYSA-N 4-(aminomethyl)aniline Chemical compound NCC1=CC=C(N)C=C1 BFWYZZPDZZGSLJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000007363 ring formation reaction Methods 0.000 claims description 2
- LJRGBERXYNQPJI-UHFFFAOYSA-M sodium;3-nitrobenzenesulfonate Chemical compound [Na+].[O-][N+](=O)C1=CC=CC(S([O-])(=O)=O)=C1 LJRGBERXYNQPJI-UHFFFAOYSA-M 0.000 claims description 2
- 239000000976 ink Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 5
- 230000000996 additive effect Effects 0.000 abstract description 4
- 238000012545 processing Methods 0.000 abstract description 4
- 239000002270 dispersing agent Substances 0.000 abstract description 3
- 239000003995 emulsifying agent Substances 0.000 abstract description 3
- 239000011248 coating agent Substances 0.000 abstract description 2
- 230000001804 emulsifying effect Effects 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 16
- 238000001514 detection method Methods 0.000 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- SDHWNDQQYQOORG-UHFFFAOYSA-N 2-anilinocyclohexa-1,4-diene-1,4-dicarboxylic acid Chemical compound C1C(C(=O)O)=CCC(C(O)=O)=C1NC1=CC=CC=C1 SDHWNDQQYQOORG-UHFFFAOYSA-N 0.000 description 2
- XKLXSHQEFPJNEL-UHFFFAOYSA-N 4-(aminomethyl)aniline;hydrochloride Chemical compound Cl.NCC1=CC=C(N)C=C1 XKLXSHQEFPJNEL-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 229940023462 paste product Drugs 0.000 description 2
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- HBBWQVPXGBHVPE-UHFFFAOYSA-N 3-(2-aminoethyl)aniline;hydrochloride Chemical compound Cl.NCCC1=CC=CC(N)=C1 HBBWQVPXGBHVPE-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- HCFPRFJJTHMING-UHFFFAOYSA-N ethane-1,2-diamine;hydron;chloride Chemical compound [Cl-].NCC[NH3+] HCFPRFJJTHMING-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000001053 orange pigment Substances 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000001054 red pigment Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
- C08G65/33396—Polymers modified by chemical after-treatment with organic compounds containing nitrogen having oxygen in addition to nitrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- C09D17/003—Pigment pastes, e.g. for mixing in paints containing an organic pigment
-
- 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
- C09D7/65—Additives macromolecular
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterized by the type of post-polymerisation functionalisation
- C08G2650/04—End-capping
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention relates to a quinacridone pigment polyether derivative and a preparation method thereof, wherein the quinacridone pigment polyether derivative has a structure shown as a formula (P):
Description
Technical Field
The invention belongs to the field of organic pigments and high-grade coatings, and relates to a derivative of a high-grade pigment quinacridone series pigment and a preparation method thereof.
Background
Quinacridones (quinacridones, QA) are all known as quino [2,3-b ] -acridine-5, 12-dihydro-7, 12-dione, first synthesized by h.liebermann in 1935. The pigment is an orange pigment and a red pigment with excellent performance due to good light, heat and chemical stability. Quinacridone molecules have highly conjugated large pi bonds and can form a planar structure, so that the quinacridone molecules are widely applied as organic photoelectric materials including organic electroluminescent devices, solar cells and field effect transistors.
Since the advent of quinacridone pigments, there have been many reports on the preparation methods and properties thereof (Bishidong, Zhouyong, high-grade organic pigments-quinacridone pigment chemistry and progress. chemical progress, 1990, (6): 23-30; Wangyonghua, Lidefang. quinacridone pigment research progress. dye industry, 199936 (5): 9-12). Patent CN1280150A describes a continuous production method of quinacridone pigment; methods for synthesizing QA pigments are described in patent CN98117860X, patent CN03112801.7, patent CN96122040.6, patent CN201180022643.0, patent CN98112582.4, patent CN00126819.8, US4881980, US4400515 and patent US 4197404; patent CN200480020603.X describes a preparation method of an asymmetric QA pigment; patent CN200380104263.7, patent CN98115086.1 and US3007930 respectively describe a method for producing a beta type QA pigment; a method for producing gamma QA pigments is described in patents CN00126819.8 and US 4197404.
In the production of QA pigments, the use of QA pigment derivatives as auxiliaries to improve the use properties of QA pigments is an important method (Chua Xiaofei, Wang Li Min, Wang Feng, etc.. quinacridone pigments and their functional research progress.dyes and dyeings, 2013,50(3): 24-27).
A quinacridone borate derivative, a preparation method and application thereof are introduced in patent CN 201210260009.7; in patent CN201210377815.2, a pentaphenyl phenyl quinacridone derivative and its application as fluorescent material are described; patent CN201110102802.X introduces a preparation method and application of quinacridone derivative substituted by alkyl, alkoxy or alkyl halide on N, and substituted by aromatic ring group and heterocyclic group on 2-position.
Patent CN03127617.2 describes a series of preparation methods of QA pigment derivatives substituted on N and benzene ring and their application in organic electroluminescent devices; patent CN200580021864.0 describes a series of preparation methods of quinacridone derivatives with fluorescent property.
U.S. Pat. Nos. 3,33868,983,982,84890, 6,647,64733 and 20020078860 disclose a process for preparing 2, 9-disulfonylaminodquinacridone and 2, 9-disulfonic acid sodium quinacridone.
Disclosure of Invention
Unlike the quinacridone derivatives and the preparation methods thereof described in the above patents, the present invention provides a quinacridone pigment derivative having non-ionic surfactant properties and a preparation method thereof.
The quinacridone pigment derivative has good water solubility, surface activity and emulsifying and dispersing capacity, can be used as an additive in the post-treatment processing of a crude quinacridone pigment product, and can also be used as a dispersant and an emulsifier in the preparation of color paste and paint of the quinacridone pigment.
The preparation method of the quinacridone pigment polyether derivative is simple, the synthesis condition is mild, the raw materials are cheap and easy to obtain, and the yield of the reactant is high.
One of the objects of the present invention is to provide a quinacridone polyether derivative which can be used for red-based color filter quinacridone pigment dispersion.
The quinacridone polyether derivative has a structure shown as a formula (P):
wherein n is any integer between 2 and 20; m is 1 or 2.
Preferred compounds according to the invention are those in which n is 10, 11 or 12 and m is 1.
The second object of the present invention is to provide a process for preparing the quinacridone pigment polyether derivative, which comprises the following steps:
in a solvent, polyethylene glycol monoglycidyl ether is adopted to react with an aminoalkyl substituted quinacridone compound shown as a formula (I) to prepare a target compound (P), n is any integer between 2 and 20, and m is 1 or 2;
in the above production method, the compound represented by the formula (I) is produced by either of the following two methods:
the 1 st: taking aminoalkyl substituted aniline shown in a formula (III) and dimethyl succinyl succinate as raw materials, firstly carrying out dehydration reaction, then carrying out cyclization reaction under the action of polyphosphoric acid, and finally oxidizing by using sodium m-nitrobenzenesulfonate to obtain aminoalkyl substituted quinacridone shown in a formula (I), wherein m is 1 or 2;
the 2 nd: p-aminomethylaniline and dimethyl succinyl succinate are used as reaction raw materials for preparation.
In the preparation method, the molar ratio range of the amine alkyl substituted quinacridone compound shown in the formula (I) to the polyethylene glycol monoglycidyl ether is 1: 1 to 3, more preferably 1: 2.
in the preparation method, the temperature in the reaction process is controlled to be 60-90 ℃, and more preferably 70-80 ℃; the reaction time is 2-6 h, and preferably 4 h.
The solvent is selected from methanol, ethanol, propanol, isopropanol or DMF.
The invention also provides the application of the aminoalkyl substituted quinacridone compound with the structure shown in the formula (P) in preparing an additive, a color paste, a coating or an aqueous ink during the post-treatment processing of a quinacridone pigment crude product.
Advantageous effects
The invention designs and synthesizes a series of not-yet-reported quinacridone polyether derivatives, and researches a methodology for synthesizing the derivatives. The quinacridone polyether derivative (P) prepared by the invention has good solubility and surface activity in water, can be used as an additive in the post-treatment processing of a crude quinacridone pigment, and can also be used as a dispersant and an emulsifier in the preparation of color paste and paint of the quinacridone pigment.
Detailed Description
The present invention will be described in further detail with reference to the following embodiments. It will be understood by those skilled in the art that the following examples are illustrative of the present invention only and should not be taken as limiting the scope of the invention. The examples do not specify particular techniques or conditions, and are performed according to the techniques or conditions described in the literature in the art or according to the product specifications. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products commercially available. The mass percentages described in the following examples refer to mass percentages unless otherwise specified.
Example 1
(1) 2, 9-diaminemethylquinacridone (I-1) is prepared from p-aminobenzylamine hydrochloride and dimethyl succinylsuccinate, as described in patent US3386843 and patent CN 98112582.4. P-aminobenzylamine hydrochloride (0.2mol, 31.6g) and dimethyl succinylsuccinate (22.8g, 0.1mol) were added to ethanol (ethanol: (ethanol-methanol-ethanol-was added to200ml) and concentrated hydrochloric acid (10ml, 37%) were reacted at 90 ℃ for 4 hours under pressure in a high-temperature high-pressure reaction vessel, cooled, filtered, washed with water, and recrystallized from methanol to give 2, 5-bis- (4' -aminomethyl) anilino-3, 6-dihydroterephthalic acid (36.74g, 0.09 mol). 2, 5-bis- (4' -aminomethyl) anilino-3, 6-dihydroterephthalic acid (40.82g, 0.1mol) was condensed with polyphosphoric acid (200g, 117% phosphoric acid) at 135 ℃ to give 2, 9-diaminomethyl-6, 13-dihydroquinacridone (37.2g, 0.1mol), and further subjected to reflux oxidation for 2 hours under sodium metanitrobenzenesulfonate (45.2g, 0.2mol), potassium hydroxide (16g, 0.285mol) and deionized water (500ml), acidified and neutralized with dilute hydrochloric acid (10%), washed with water and filtered to give 2, 9-diaminomethyl quinacridone (I-1) (31.5g, 0.085 mol). The product (I-1) hydrogen nuclear magnetic resonance detection result, 1HNMR (CDCl)3，500MHz)δ(ppm)：2.0(s,2H)，3.01(s,2H)，4.01(m,2H)，4.5(s,1H)，6.44(s,1H)，6.75(s,1H)，7.01(s,1H)，7.25(s,1H)。
(2) In a four-necked flask equipped with a condenser, ethanol (30ml) was added, and heated to 70 ℃ to add 2, 9-diaminomethylquinacridone (I-1) (0.01mol, 3.70g) under stirring, and PEG400 monoglycidyl ether (about 0.01mol, 10g) was added in portions, and after completion of the addition, heated to 80 ℃ under reflux for 4 hours, cooled to room temperature, and the mixture was transferred to a rotary evaporator to rotary-evaporate ethanol to give 13.5g of red paste product (P-1) in 99% yield.
Example 2
(1) 3, 8-Diaminoethylquinacridone (I-2) is prepared using m-aminophenylethylamine hydrochloride by the same method as in example 1.
(2) In a four-necked flask equipped with a condenser, ethanol (30ml) was added, the mixture was heated to 70 ℃ and 3, 8-diaminoethylquinacridone (I-2) (0.01mol, 3.98g) was added under stirring, PEG400 monoglycidyl ether (about 0.01mol, 10g) was further added in portions, after completion of the addition, the mixture was heated to 80 ℃ and refluxed for 4 hours, cooled to room temperature, the mixture was transferred to a rotary evaporator, and methanol was rotary-distilled off to obtain 13.78g of red paste product (P-2) in 99.5% yield. The product is confirmed by structure detection, and the main characteristic peak of the hydrogen nuclear magnetic resonance detection result is the same as that of the product in the example 1.
Example 3
3, 8-diaminomethylquinacridone (I-3) is prepared as in example 2, using the aminoethylamide hydrochloride. Then the product I-3 is further reacted with polyethylene glycol (15) monoglycidyl ether in a propanol solvent to obtain the product P-3 with a yield of 99.3%. The product is confirmed by structure detection, and the main characteristic peak of the hydrogen nuclear magnetic resonance detection result is the same as that of the product in the example 1.
Example 4
The experimental procedure was as in example 3, using polyethylene glycol glycidyl ether with a degree of polymerization of 20 to give product P-4 as shown in the following formula with a yield of 99.1%. The product is confirmed by structure detection, and the main characteristic peak of the hydrogen nuclear magnetic resonance detection result is the same as that of the product in the example 1.
Example 5
2, 9-diaminemethyl quinacridone (I-1) is reacted with polyethylene glycol glycidyl ether with the polymerization degree of 18 to obtain a product P-5. The product is confirmed by structure detection, and the main characteristic peak of the hydrogen nuclear magnetic resonance detection result is the same as that of the product in the example 1.
Comparative example 1
The commercially available pigmentary quinacridone PV19 is used as reference.
Performance detection
Preparation and performance test of C.I. pigment red 122 aqueous emulsion
37g of C.I. pigment Red 122, 3g of the hyperdispersant of the above examples and comparative examples and 60g of deionized water were put into a glass bottle, sealed, put into a shaker for shaking for 3 hours, and then subjected to various performance tests. The test results are given in table 1 below.
Table 1 emulsion test results
As can be seen from the above table, the quinacridone polyether derivative prepared by the invention has better dispersibility, and when used in dyes, the dispersion effect is better than that of the existing quinacridone pigment, wherein the P1 compound has the best dispersibility.
Claims (9)
1. A quinacridone polyether derivative having a structure represented by formula (P):
wherein n is any integer between 2 and 20; m is 1 or 2.
2. The quinacridone polyether derivative according to claim 1, characterized in that n is 10, 11 or 12 and m is 1.
3. A process for preparing quinacridone polyether derivatives according to claim 1, comprising the steps of:
in a solvent, polyethylene glycol monoglycidyl ether is adopted to react with an aminoalkyl substituted quinacridone compound shown as a formula (I) to prepare a target compound (P), n is any integer between 2 and 20, and m is 1 or 2;
4. a process for preparing quinacridone polyether derivatives according to claim 3, characterized in that: the compound shown in the formula (I) is prepared by the following method:
taking aminoalkyl substituted aniline shown in a formula (III) and dimethyl succinyl succinate as raw materials, firstly carrying out dehydration reaction, then carrying out cyclization reaction under the action of polyphosphoric acid, and finally oxidizing by using sodium m-nitrobenzenesulfonate to obtain aminoalkyl substituted quinacridone shown in a formula (I), wherein m is 1 or 2;
5. a process for preparing quinacridone polyether derivatives according to claim 4, characterized in that: the aminoalkyl substituted aniline represented by the formula (III) is p-aminomethylaniline.
6. A process for preparing quinacridone polyether derivatives according to claim 3, characterized in that: the molar ratio of the aminoalkyl substituted quinacridone compound according to formula (I) to the polyethylene glycol monoglycidyl ether is in the range of 1: 1 to 3.
7. A process for preparing quinacridone polyether derivatives according to claim 3, characterized in that: the temperature in the reaction process is controlled to be 60-90 ℃; the reaction time is 2-6 h.
8. A process for preparing quinacridone polyether derivatives according to claim 3, characterized in that: the solvent is selected from methanol, ethanol, propanol, isopropanol or DMF.
9. Use of the quinacridone polyether derivative according to claim 1 or 2 in additives, pastes, coatings or aqueous inks for the preparation of the quinacridone pigment crude aftertreatment processes.
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| CN201611155661.7A CN107057054B (en) | 2016-12-14 | 2016-12-14 | Quinacridone polyether derivatives and preparation method and application thereof |
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| EP1295919A3 (en) * | 2001-09-20 | 2003-11-19 | Eastman Kodak Company | Ink jet ink composition comprising a hyperbranched polymer and printing method |
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