CN112341473B - Novel green phthalocyanine derivative and preparation method thereof - Google Patents
Novel green phthalocyanine derivative and preparation method thereof Download PDFInfo
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- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
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- 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
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
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Abstract
The invention provides a novel green phthalocyanine derivative, the structure of which is shown as the general formula (1)
Wherein M represents a 2-valent metal or two hydrogen atoms; r1 is selected from the group consisting of hydrogen, C1-24 alkyl, C2-24 alkoxyalkyl, C2-24 alkylaminoalkyl, C2-24 alkylmercaptoalkyl, C2-24 alkylsulfonamido, substituted and unsubstituted C3-24 cycloalkyl, substituted and unsubstituted C2-24 heterocycloalkyl, substituted and unsubstituted C7-24 aralkyl, C2-24 acyl, substituted and unsubstituted C6-24 aryl, and substituted and unsubstituted C4-24 heteroaryl; r2 is selected from nitro, cyano, C2-24 acyl, C2-24 alkyl substituted ester group and C2-24 alkyl substituted amide group. The invention also provides a preparation method of the phthalocyanine derivative. The maximum absorption wavelength of the compound is 698-700nm, and the compound can be applied to green new pigments and has high contrast.
Description
Technical Field
The invention relates to the technical field of organic synthetic dyes, in particular to a novel green phthalocyanine derivative and a preparation method thereof.
Background
In the prior art, common organic synthetic green dye is phthalocyanine pigment, for example, pigment green 58 (polybrominated zinc phthalocyanine P.G.58) is the main green pigment in the current market, a large amount of halogen and aluminum trichloride are used in the production process, the production process of the pigment needs a highly-polluted halogenation process, the treatment of waste liquid in the production process is also a great problem, and the pigment has high potential safety hazard and causes great load on the environment. Secondly, most phthalocyanine compounds are insoluble in organic solvents, pigments are dispersed in organic solvents in the form of small particles, pigments exist in the form of small particles, agglomeration easily occurs in organic solvents, and there is generally a problem of insufficient dispersibility, which in turn leads to insufficient brightness and contrast.
The patent with publication number WO2016015208A1 discloses a phenoxy substituted green phthalocyanine derivative which has good solubility, and has the advantages of high contrast and good stability when applied in the field of liquid crystal, but is not suitable for large-scale industrial application.
Therefore, more phthalocyanine compounds with good solubility and high contrast ratio, which can be produced on a large scale, are required to meet the demand of phthalocyanine green dyes in the market.
Disclosure of Invention
The present invention has been made to solve the above-mentioned problems occurring in the prior art.
The first aspect of the present invention provides a novel green phthalocyanine derivative having a structure represented by general formula (1):
wherein M represents a 2-valent metal or two hydrogen atoms;
r1 is selected from the group consisting of a hydrogen atom, a C1-24 alkyl group, a C2-24 alkoxyalkyl group, a C2-24 alkylaminoalkyl group, a C2-24 alkylmercaptoalkyl group, a C2-24 alkylsulfonamido alkyl group, a substituted and unsubstituted C3-24 cycloalkyl group, a substituted and unsubstituted C2-24 heterocycloalkyl group, a substituted and unsubstituted C7-24 aralkyl group, a C2-24 acyl group, a substituted and unsubstituted C6-24 aryl group, and a substituted and unsubstituted C4-24 heteroaryl group;
r2 is selected from nitro, cyano, C2-24 acyl, C2-24 alkyl substituted ester group and C2-24 alkyl substituted amido.
Preferably, M is selected from copper, zinc, iron, nickel, cobalt, titanium, magnesium or palladium.
Preferably, the novel green phthalocyanine derivative is selected from the following compounds:
in a second aspect, a process for the preparation of the novel green phthalocyanine derivative as described above has the general reaction formula:
the method specifically comprises the following steps:
s1: reacting 4-bromo-5-nitrophthalonitrile with compound 1 to prepare compound 2:
s11: under the protection of nitrogen, adding potassium carbonate and the compound 1 into a reaction bottle, adding anhydrous DMF (N, N-dimethylformamide), and uniformly stirring to obtain a first mixed solution;
s12: adding 4-bromo-5-nitrophthalonitrile into the first mixed solution in batches to obtain a second mixed solution;
s13: under the protection of nitrogen, heating the second mixed solution until the reaction is finished, cooling, pouring the second mixed solution into water, separating out a first solid, sequentially performing suction filtration and washing on the first solid, and drying to obtain the compound 2;
s2: the compound 2 is condensed to prepare the novel green phthalocyanine derivative:
s21: adding the compound 2, metal chloride and n-octanol into a dry reaction bottle under the protection of nitrogen to obtain a third mixed solution;
s22: under the protection of nitrogen, DBU (1,8-diazabicycloundecen-7-ene) is added, the third mixed solution is heated until the reaction is finished, methanol is added after the third mixed solution is cooled, the mixture is uniformly stirred and filtered to obtain a second solid, and the second solid is washed by methanol and dried to obtain the novel green phthalocyanine derivative.
Preferably, in step S11, the molar ratio of the 4-bromo-5-nitrophthalonitrile to the potassium carbonate is: 1:2 to 5; further, the molar ratio is: 1:4-5.
Preferably, in step S12, the molar ratio of the 4-bromo-5-nitrophthalonitrile to the compound 1 is: 1:1 to 2.5; further, the molar ratio is: 1, 2.0-2.5.
Preferably, in step S13, the heating temperature is 20-80 ℃ and the reaction time is 1-24 h.
Preferably, in step S21, the molar ratio of said compound 2 to said metal chloride: 1:0.25 to 0.4.
Preferably, in step S22, the molar ratio of said compound 2 to said DBU: 1:0.5 to 2.
Preferably, in step S22, the heating temperature is 120-190 ℃, the reaction time is 1-24 h, and the cooling temperature is 25-75 ℃.
Third aspect the present invention claims a green pigment comprising the novel green phthalocyanine derivative as described above.
By adopting the technical scheme, compared with the prior art, the invention has the following technical effects:
the invention provides a new phthalocyanine derivative, which has the maximum absorption wavelength of 698nm-700nm and can be applied to a new green pigment. The pigment prepared by the phthalocyanine derivative has higher contrast.
Drawings
FIG. 1 is an electrospray mass spectrometry test pattern of Compound 2 of example 2 of the present invention;
FIG. 2 is a test chart of the 2 1H NMR spectroscopy of the compound of example 2 of the present invention;
FIG. 3 is a test spectrum of the 2 13C NMR spectroscopy of the compound of example 2 of the present invention;
FIG. 4 is an ultraviolet-visible spectrum of a green phthalocyanine derivative ZnPc1 in example 3 of the present invention;
FIG. 5 is an ultraviolet-visible spectrum of a green phthalocyanine derivative CuPc1 in example 4 of the present invention.
Detailed Description
The invention provides a novel green phthalocyanine derivative, the structure of which is shown as a general formula (1):
wherein M represents a 2-4 valent metal or two hydrogen atoms;
r1 is selected from the group consisting of a hydrogen atom, a C1-24 alkyl group, a C2-24 alkoxyalkyl group, a C2-24 alkylaminoalkyl group, a C2-24 alkylmercaptoalkyl group, a C2-24 alkylsulfonamido alkyl group, a substituted and unsubstituted C3-24 cycloalkyl group, a substituted and unsubstituted C2-24 heterocycloalkyl group, a substituted and unsubstituted C7-24 aralkyl group, a C2-24 acyl group, a substituted and unsubstituted C6-24 aryl group, and a substituted and unsubstituted C4-24 heteroaryl group;
r2 is selected from nitro, cyano, C2-24 acyl, C2-24 alkyl substituted ester group and C2-24 alkyl substituted amide group.
Specifically, the novel green phthalocyanine derivative may be the following compound:
the reaction general formula of the preparation method of the novel green phthalocyanine derivative is as follows:
the method specifically comprises the following steps:
s1: 4-bromo-5-nitrophthalonitrile with compound 1 to prepare compound 2:
s11: under the protection of nitrogen, adding potassium carbonate and the compound 1 into a reaction bottle, adding anhydrous DMF, and uniformly stirring to obtain a first mixed solution;
s12: adding 4-bromo-5-nitrophthalonitrile into the first mixed solution in batches to obtain a second mixed solution;
s13: under the protection of nitrogen, heating the second mixed solution until the reaction is finished, cooling, pouring the second mixed solution into water, separating out a first solid, sequentially performing suction filtration and washing on the first solid, and drying to obtain the compound 2;
s2: the compound 2 is condensed to prepare the novel green phthalocyanine derivative
S21: adding the compound 2, metal chloride and n-octanol into a dry reaction bottle under the protection of nitrogen to obtain a third mixed solution;
s22: under the protection of nitrogen, after DBU is added, heating the third mixed solution until the reaction is finished, cooling the third mixed solution, adding methanol, uniformly stirring, filtering to obtain a second solid, washing the second solid with methanol, and drying to obtain the novel green phthalocyanine derivative.
The present invention will be described in detail and specifically with reference to the following examples to facilitate better understanding of the present invention, but the following examples do not limit the scope of the present invention.
Example 1
The embodiment provides a novel green phthalocyanine derivative ZnPc1, which has the following structure:
example 2
This example provides a method for preparing the following compound 2 (dicyano-substituted benzofuran derivative), among the methods for preparing the novel green phthalocyanine derivative ZnPc1 of example 1.
The method comprises the following specific steps:
pre-preparation: 4-bromo-5-nitrophthalonitrile synthesis is prepared according to patent US20060142553 A1;
s1: 4-bromo-5-nitrophthalonitrile with Compound 1 to prepare Compound 2 (dicyano-substituted benzofuran derivative):
s11: under the protection of nitrogen, adding 4.4eq potassium carbonate (47.1g, 0.44mol) and 2.2eq acetylacetone (22.2g, 0.22mol) into a reaction bottle, adding 350ml anhydrous DMF, and stirring uniformly to obtain a first mixed solution;
s12: adding 1eq of 4-bromo-5-nitrophthalonitrile (25.5g, 0.1mol) to the first mixed solution in portions, heating to 30 ℃, and reacting for 1 hour under nitrogen protection;
s13: after the reaction, the temperature was reduced, and the reaction solution was poured into water to precipitate a first solid, which was then filtered, washed, and dried to obtain compound 2 (6.5 g, yield 31%).
Characterization of compound 2 (dicyano-substituted benzofuran derivative):
as in FIG. 1, ESI-MS:255.1, [ M ] +H ],247.2[ 2 ], [ M ] +Na ],471.1[2 ] M + [ Na ].
As in FIG. 2, 1H NMR (400MHz, D6-DMSO): delta =8.61-8.62 (d, 2H), 2.88 (s, 3H), 2.64 (s, 3H).
13C NMR (101MHz, D6-DMSO): delta =193.2,168.2,152.9,130.3,127.8,117.8,117.0,116.1,110.2,109.8,30.8,15.3, as in FIG. 3.
Example 3
This example uses compound 2 of example 2 to prepare the new green phthalocyanine derivative ZnPc1 of example 1 by condensation. The method comprises the following specific steps:
s21: under the protection of nitrogen, 1eq of compound 2 (4.2g, 0.02mol), 0.3eq of zinc chloride (0.84g, 0.006mol) and 32eq of n-octanol (168.4 g, 0.64mol) were added to a dry reaction flask to obtain a third mixed solution;
s22: adding 1.5eq DBU (2.76g, 0.03mol) under the protection of nitrogen, heating to 180 ℃, reacting for 6 hours under the protection of nitrogen, cooling to 70 ℃ after the reaction is finished, adding 100g methanol, stirring for 10 minutes, filtering, washing the solid with 1000g methanol until the filtrate has no obvious color, and drying to obtain a green solid, namely a product ZnPc1 (1.34 g, yield 28%).
And (3) characterizing the product ZnPc 1:
as in fig. 4, the UV-vis spectrum UV-vis:698nm.
Matrix-assisted laser desorption ionization time-of-flight mass spectrometry Maldi-tof-MS:961.2[ M ] +H ];962.2[ M ] +2H ].
Example 4
This example provides a novel green phthalocyanine derivative CuPc1, which has the following structure:
this example uses compound 2 of example 2 to prepare the above-mentioned novel green phthalocyanine derivative CuPc1 by condensation. The method comprises the following specific steps:
s21: under the protection of nitrogen, 1eq of compound 2 (4.2g, 0.02mol), 0.3eq of anhydrous copper chloride (0.81g, 0.006mol) and 32eq of n-octanol (168.4 g, 0.64mol) were added to a dry reaction flask to obtain a third mixed solution;
s22: adding 1.5eqDBU (2.76g, 0.03mol) under the protection of nitrogen, heating to 180 ℃, reacting for 6 hours under the protection of nitrogen, cooling to 70 ℃ after the reaction is finished, adding 100g of methanol, stirring for 10 minutes, filtering, washing the solid with 1000g of methanol until the filtrate has no obvious color, and drying to obtain a green solid, namely a product CuPc1 (2.1 g, yield 43%).
And (3) characterizing the product CuPc 1:
as in fig. 5, the UV-vis spectrum UV-vis:700nm.
Matrix-assisted laser desorption ionization time-of-flight mass spectrometry Maldi-tof-MS:960.2[ M ] +H ].
Contrast testing
This example tested the contrast of the phthalocyanine compound ZnPc1 in example 1 and CuPc1 in example 4.
(1) Sample Dispersion
Pigment color paste prepared from the materials in the following table 1
TABLE 1 composition of pigment pastes
| Raw materials | Weight/g |
| disperbyk2001(NV40％) | 16.5 |
| PGMEA | 46.5 |
| PGME | 11.6 |
| ZnPc1 or CuPc1 | 9.0 |
| ZrO(0.1～0.2mm) | 190 |
The dispersion conditions were as follows: oscillator
Dispersing time: 7h +/-10 min
Dispersion temperature: 25 +/-5 ℃.
(2) Glass sheet preparation
2.1 preparation of glass sheets
Glass sheet size specification: 70mm 50mm 1.1mm, high quality float glass sheet, luoyanggulo glass ltd (www.guluoglass.com). The model of the spin coater: lab Spin6/8, inc: SUSS MicroTec.
Spin coating parameters: the spin coater rotation speeds were 200rpm,300rpm,600rpm,1000rpm and 1600rpm, respectively, depending on the film thickness, and spin coating was carried out for 60-120 seconds, respectively.
2.2 the glass sheet is dried in an oven after being coated, and is dried for 30min at the temperature of 80 ℃.
(3) Testing (x, Y) and Y values
3.1 Instrument model: hitachi, U3900H Spectrophotometer
3.2 the procedure of the test is as follows:
(1) starting the equipment and the computer, closing the shading plate, and waiting for automatic calibration of the instrument;
(2) selecting a test method (detecting wavelength is 380 nm-780 nm, and testing transmittance);
(3) placing a blank glass sheet, and running a base line;
(4) and (5) placing a sample wafer to be tested, and testing to obtain (x, Y) and Y values.
(4) Testing contrast
4.1 Instrument model: topcom, BM-5AS
4.2 procedure for testing as follows:
(1) blank contrast was adjusted to 10000. Respectively testing bright state data L/and testing dark state data L vertical;
(2) L/L ≠ is obtained, and the contrast at x =0.25 is calculated according to the linear relation and the (x, Y) and Y values.
TABLE 2 contrast Performance comparison of ZnPc1, cuPc1 and P.G.58
| Sample(s) | CR (contrast) |
| P.G.58 | 100％ |
| ZnPc1 | 116 |
| CuPc1 | |
| 110％ |
As can be seen from table 2, the contrast of the phthalocyanine compounds ZnPc1 and CuPc1 is greatly improved compared to the existing product p.g.58. Among the phthalocyanine derivatives of the same type, znPc1 has higher contrast than CuPc1.
The embodiments of the present invention have been described in detail, but the embodiments are merely examples, and the present invention is not limited to the embodiments described above. Any equivalent modifications and substitutions to those skilled in the art are also within the scope of the present invention. Accordingly, equivalent changes and modifications made without departing from the spirit and scope of the present invention should be covered by the present invention.
Claims (10)
1. A green phthalocyanine derivative having a structure represented by general formula (1):
wherein M represents copper or zinc;
r1 is selected from C1-24 alkyl;
r2 is selected from C2-24 acyl or C2-24 alkyl substituted ester group.
2. The green phthalocyanine derivative according to claim 1, wherein the green phthalocyanine derivative is selected from the following compounds:
3. a process for preparing a green phthalocyanine derivative according to claim 1 or 2, characterized in that it has the general reaction formula:
wherein TM represents the green phthalocyanine derivative,
the method specifically comprises the following steps:
s1: reacting 4-bromo-5-nitrophthalonitrile with compound 1 to prepare compound 2:
s11: under the protection of nitrogen, adding potassium carbonate and the compound 1 into a reaction bottle, adding anhydrous DMF, and uniformly stirring to obtain a first mixed solution;
s12: adding 4-bromo-5-nitrophthalonitrile into the first mixed solution in batches to obtain a second mixed solution, and heating the second mixed solution under the protection of nitrogen until the reaction is finished;
s13: after cooling, pouring the second mixed solution into water, precipitating a first solid, sequentially carrying out suction filtration and washing on the first solid, and drying to obtain the compound 2;
s2: the compound 2 is condensed to prepare the green phthalocyanine derivative:
s21: adding the compound 2, metal chloride and n-octanol into a dry reaction bottle under the protection of nitrogen to obtain a third mixed solution;
s22: under the protection of nitrogen, heating the third mixed solution after DBU is added until the reaction is finished, cooling the third mixed solution, adding methanol, uniformly stirring, filtering to obtain a second solid, washing the second solid with methanol, and drying to obtain the green phthalocyanine derivative.
4. The method for producing a green phthalocyanine derivative according to claim 3, wherein in step S1, the molar ratio of the 4-bromo-5-nitrophthalonitrile to the potassium carbonate is: 1:2 to 5.
5. The method for producing a green phthalocyanine derivative according to claim 3, wherein in step S12, the molar ratio of the 4-bromo-5-nitrophthalonitrile to the compound 1 is: 1:1 to 2.5.
6. The method for producing a green phthalocyanine derivative according to claim 3, wherein the heating temperature is 20 to 80 ℃ and the reaction time is 1 to 24 hours in step S12.
7. The method for producing a green phthalocyanine derivative according to claim 3, wherein the molar ratio of the compound 2 to the metal chloride in step S21 is: 1:0.25 to 0.4.
8. The method for producing a green phthalocyanine derivative according to claim 3, wherein the molar ratio of the compound 2 to the DBU in step S22 is: 1:0.5 to 2.
9. The method for preparing a green phthalocyanine derivative according to claim 3, wherein the heating temperature is 120 to 190 ℃, the reaction time is 1 to 24 hours, and the cooling temperature is 25 to 75 ℃ in step S22.
10. A green pigment comprising the green phthalocyanine derivative as described in claim 1 or 2.
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