CN111607247A - Mixed crystal type naphthol AS organic pigment and preparation method thereof - Google Patents
Mixed crystal type naphthol AS organic pigment and preparation method thereof Download PDFInfo
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- CN111607247A CN111607247A CN202010549687.XA CN202010549687A CN111607247A CN 111607247 A CN111607247 A CN 111607247A CN 202010549687 A CN202010549687 A CN 202010549687A CN 111607247 A CN111607247 A CN 111607247A
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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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/18—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides
- C09B29/20—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides of the naphthalene series
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/22—Compounds containing nitrogen bound to another nitrogen atom
- C08K5/23—Azo-compounds
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
-
- 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
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
- C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the 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
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/322—Pigment inks
Abstract
The invention belongs to the field of preparation of coloring agents, and relates to a mixed crystal type naphthol AS organic pigment and a preparation method thereof. The mixed crystal form naphthol AS organic pigment I consists of two organic pigment molecules Ia and Ib, wherein R in Ib molecule1，R2And R3May be one or more of alkyl, alkoxy, nitro, halogen or heterocycle. Solves the problems of short operation time and poor flame retardance of the prior epoxy resin and prepreg thereof.
Description
Technical Field
The invention belongs to the field of preparation of coloring agents, and relates to a mixed crystal type naphthol AS organic pigment and a preparation method thereof.
Background
The naphthol AS series organic pigments are red organic pigments prepared by coupling a diazonium salt of a substituted aromatic amine with 2-hydroxy-N-substituted phenyl-3-naphthamide and are widely used for coloring paints, inks and plastics [ W.Herbst, Industrial organic pigments, Thirdedition, ISBN: 3-527-. One important variety, N- (4-chloro-2, 5-dimethoxyphenyl) -3-hydroxy-4- [ [ 2-methoxy-5- [ (anilino) -carbonyl ] phenyl ] azo ] -2-naphthalimide Ia, organic pigment Red 146, has good solvent resistance, acid and base resistance and retort resistance, and is used for packaging inks and digital inkjet four-color Red. In recent years, with the development of package printing applications and the popularization of digital ink-jet technology applications, the chromatographic requirements of four-color red are widened, and the hue angle of 0.8 degrees (D65,10 degrees) of the original rubine color cannot meet the requirements of different applications; in addition, since the fields of application of packaging inks and digital inkjet inks are related to human contact and food packaging, there is a high demand for the content of harmful substances in the products. The color properties (hue angle, saturation and transparency) of conventional products and the content of harmful components of the products are to be improved.
Disclosure of Invention
The invention mainly solves the defects in the prior art, and provides a mixed crystal type naphthol AS organic pigment and a preparation method thereof, which solve the problems of short operation time and poor flame retardance of the prior epoxy resin and prepreg thereof.
The technical problem of the invention is mainly solved by the following technical scheme:
a mixed crystal type naphthol AS organic pigment is composed of two organic pigment molecules Ia and Ib, wherein R in Ib molecule1，R2And R3Can be one or more of alkyl, alkoxy, nitro, halogen or heterocycle, and the structural formula of I is as follows:
I1-6the powder X-ray diffraction pattern of (A) shows a characteristic diffraction peak at 6:
wherein Ia represents the molecular structural formula of the organic pigment red 146, Ib represents the molecular structural formula of the second component, and R in Ib molecule1,R2And R3Represents a substituent which may be an alkyl group, an alkoxy group, a nitro group, a halogen group or a heterocyclic group. The product I obtained1-6Compared with the hue angle of Ia, the hue angle of (A) is obviously enlarged, and the requirements of different application chromatograms can be met. Other color properties, as shown in Table-1, such as a color strength index K/S of greater than 21.42 for pigment Red 146 and a chroma index C of greater than 62.8 for pigment Red 146, are superior to the corresponding properties for pigment Red 146. In addition, through process optimization, the harmful impurity haematochrome KD in the obtained product is less than or equal to 100ppm, and the content of 4-chloro-2, 5-dimethoxyaniline or other substituted arylamine is less than or equal to 150ppm, so that the application safety of the product in the fields of human body contact and food packaging is ensured, and the product is an ideal colorant for packaging ink, digital ink jet, plastics and special ornaments.
Table one: i is1-6Color and application property data (Ia: Ib ═ 1:1 mixed coupling products)
To achieve the object of the present invention, the inventors provide the following technical solutions according to the following chemical reaction equations:
a preparation method of mixed crystal type naphthol AS organic pigment comprises the following steps:
the preparation method of I has three methods:
a. hybrid coupling method: diazotizing 3-amino-4-methoxybenzoyl aniline, and then carrying out coupling reaction on the diazotized 3-amino-4-methoxybenzoyl aniline, the coupling component 2 ', 5 ' -dimethoxy-4 ' -chloro-3-hydroxy-2-naphthoyl aniline of Ia and the coupling component naphthol AS and derivatives thereof of Ib in a mixture with a molar ratio of 100:1 to 1:1 in water in the presence of a surfactant with an HLB value of 15-18, and heating, filtering, rinsing, drying and grinding the obtained pigment suspension to obtain I;
the inventors have found that controlling the end point of the reaction by thin layer chromatography ensures that the unreacted red base KD is present in the product in an amount of less than 100ppm and also reduces its self-coupling reaction in the diazonium salt solution, which generally has a negative effect on the shading and boiling resistance properties of the pigment. Preferably, the thin layer chromatography is performed by using a fluorescent silica gel plate as a thin layer plate, methanol/toluene (3: 1) as a developing agent, and an ultraviolet light source with the wavelength of 254nm as an observation light source, wherein the sample is spotted every 15 minutes until the spot at the Rf of 0.5 disappears as the reaction end point.
The inventor researches and discovers that the coupling components IV and V can be increased by using a surfactant with the HLB value of 15-18 as a coupling assistant agent1-6The solubility in water ensures that the coupling reaction is completely carried out, and 4-chloro-2, 5-dimethoxyaniline or other arylamine is avoided from being generated due to the hydrolysis of the coupling component in the post-processing procedure, so that the content of the hydrolysis products in the pigment product is less than or equal to 150ppm, and the safety of the product in food contact application is ensured. As a preferred scheme, the surfactant which can be used is polysorbate, polyoxyethylene fatty acid ester or fatty alcohol polyoxyethylene ether; the amount of the surfactant is 1-12% of the pigment content.
The inventors have found that, in the mixed coupling process, the coupling components IV and V are adjusted1-6The molar ratio of (A) to (B) can obtain products with different color strength, saturation, glossiness and transparency. The adjustment range is from 100:1 to 1: 1. Preferably, the transparency and gloss are highest at a molar ratio of 1: 1.
b. Coating coupling method: diazotizing 3-amino-4-methoxybenzoyl aniline, firstly coupling with a certain amount of coupling component naphthol AS of Ib and derivatives thereof in the presence of a surfactant with an HLB value of 15-18, then coupling with coupling component 2 ', 5 ' -dimethoxy-4 ' -chloro-3-hydroxy-2-naphthoyl aniline of Ia, and heating, filtering, rinsing, drying and grinding the obtained pigment suspension to obtain I;
the inventors have found that the product obtained by this coupling process, in addition to an improvement in shade, has a resistance which is more favourable to the properties of the pigment corresponding to the second coupling component than the pigment corresponding to the two coupling components. Preferably, a product with good boiling resistance can be obtained by using IV as the second coupling component and V6As the second coupling component, a product having good solvent resistance can be obtained.
c. A mixing and grinding method: diazotizing two parts of 3-amino-4-methoxybenzoyl aniline, then respectively mixing the diazotized two parts of 3-amino-4-methoxybenzoyl aniline with a coupling component of 2 ', 5 ' -dimethoxy-4 ' -chloro-3-hydroxy-2-naphthoyl aniline and a coupling component of naphthol AS for synthesizing Ib and derivatives thereof to prepare a suspension or a filter cake of Ia and Ib, then uniformly mixing the suspension or the filter cake according to a molar ratio of 100:1 to 1:1, grinding the mixture to a fineness of less than or equal to 40 mu m by using a colloid grinder, and heating, filtering, rinsing, drying and grinding the mixture to obtain I.
The inventors have found that the products obtained in this way have better dispersibility in plastics colorations than the corresponding products Ia and Ib; and better storage stability in applications such as digital ink jet, packaging ink and paint tinting. Preferably, the mixing of Ia and Ib can be performed by a high-speed beater or a sand mill to achieve the effect of mixing the microcrystals. The mixture can be dried by spray drying, and the obtained pigment can be used without grinding.
Preferably, the diazotization reaction for preparing I is carried out in a water/inorganic acid medium, and the completeness of diazotization is monitored by adopting thin-layer chromatography, so that the diazotization reaction is ensured to be complete, and the content of diazotization components in a final product is less than or equal to 100 ppm.
Preferably, the coupling reaction for preparing I is carried out in an acid-out solution of the coupling component; the coupling reaction is completely carried out by adopting the coupling assistant agent, the content of unreacted coupling components in the obtained pigment is low, the condition that the content of 4-chloro-2, 5-dimethoxyaniline in the product exceeds 150ppm due to hydrolysis of the coupling components in the post-process is avoided, and the safety of the product in human contact and food packaging application is ensured.
Preferably, the molar ratio of Ia to Ib in I can be adjusted according to needs, so that the transmission rate is from 20 to 27, the gray degree is from 58 to 36, the definition is from 92 to 95, and the visual transparency is from 3 to 6 grades; the product with the color phase angle from 1 degree to 353 degrees can meet different application requirements.
The three different preparation methods can obtain products which can meet different requirements of customers on product transparency; the mixing and coupling method can prepare a high-transparency product which is suitable for manufacturing packaging ink; the coating coupling method can prepare a product with moderate transparency, and is suitable for manufacturing digital ink jet; the mixing method can prepare relatively covered products, and is suitable for coloring plastics and special decorative materials.
The invention relates to a mixed crystal type naphthol AS organic pigment and a preparation method thereof, and solves the problems of short operation time and poor flame retardance of the conventional epoxy resin and prepreg thereof.
Detailed Description
Below with I1，The preparation of Ia: Ib ═ 1:1 is an example, illustrating the contents of the invention more specifically. It is to be understood that the practice of the present invention is not limited to the following examples, and that various changes or modifications may be made without departing from the scope of the invention.
In the invention, all parts and percentages are weight units, and all equipment, raw materials and the like can be purchased from the market or are commonly used in the industry, if not specifically indicated. Unless otherwise indicated, the examples employ methods that are within the ordinary skill in the art.
Example 1:
preparation of I by hybrid coupling1
Diazotizing the red base KD, namely adding 32.5g of red base KD (II) (99 percent, 0.133mol) and 3400ml of water into a 1000ml beaker, stirring for 60 minutes to fully wet the red base KD, and adding ice to adjust the temperature to be 0-5 ℃. 72g (0.31mol) of 31.5% hydrochloric acid was added thereto, and the stirring was adjusted to be rapid, and 26.8g of a sodium nitrite solution (35%, 0.14mol) was rapidly added thereto under liquid, and the diazotization reaction was completed by stirring. During this period, a fluorescent silica gel plate was used as a thin layer plate, methanol/toluene (3: 1) was used as a developing agent, spotting was performed once every 15 minutes by stirring, an ultraviolet light source having a wavelength of 254nm was used as a light source for observation, and stirring was performed until the spot at Rf of 0.5 disappeared to be regarded as a reaction end point.
1. Preparation of mixed coupling component solution: into a 1000ml beaker were added 24.3g of naphthol AS-LC (IV) (99%, 0.067mol) and 17.87g of naphthol AS (V)1) (99%, 0.067mol) and 400ml of water, and then 45.4g (0.34mol) of 29.5% aqueous alkali was added thereto, and the mixture was dissolved at a certain temperature for several minutes. After complete dissolution, the mixture is immediately cooled to normal temperature by ice for standby.
2. Mixing and coupling: 35ml of water, 5g (0.052mol) of 29.5% liquid alkali, 60g of 98% acetic acid and 803.0g of polysorbate are sequentially added into a 5000ml coupling beaker, rapid stirring is started, and the naphthol AS-LC and AS solution prepared in the step 2 are added into the coupling beaker for about 60 minutes for acid precipitation. After the acid precipitation is finished, the pH value is between 5.0 and 5.2, and the temperature is less than 30 ℃. After stirring for 5 to 10 minutes, the temperature of the naphthol AS-LC and AS coupling component suspension is adjusted to about 50 ℃, and a proper amount of liquid alkali is added to adjust the pH to 5.6. The diazo salt solution is pumped into the prepared coupling component suspension at a constant speed for coupling within 3 hours, and the temperature is controlled between 50 ℃ and 60 ℃. After the addition of the diazonium salt solution is finished, stirring is continued for 15 to 30 minutes, and the temperature is maintained until the excess diazonium disappears. The resulting red pigment suspension was filtered and the filter cake was rinsed with about 3000ml of water to a pH of 6-8 in the filtrate. Drying the filter cake at 110 deg.C for 3 hr to obtain red dry cake with water content less than 1%, and grinding to obtain dark red powder I171.0g, yield: 99.6 percent, and the KD content and the arylamine content in the product are 50ppm and 125ppm respectively.
Example 2:
preparation of I by coating coupling method1
32.5g of the red base KD (II) (99%, 0.133mol) were diazotized according to the diazotization method described in example-1 to give a diazonium salt solution for further use. Further according to example-1The coupling components were dissolved by preparing 24.3g of naphthol AS-LC (IV) (99%, 0.067mol) and 17.87g of naphthol AS (V) in two beakers1) (99%, 0.067mol) and acidified for use. The diazonium salt was then coupled with the first coupling component by the coupling method described in example-1, after the coupling was complete the second coupling component was added and the coupling was continued after stirring until homogeneous, after the coupling the pigment suspension was filtered, dried and milled to give 70.8g of a dark red powder with a yield of 99.2% and a KD content of 45ppm and an arylamine content of 110ppm in the product.
EXAMPLE-3 Mixed milling Process preparation I1
32.5g of the red base KD (II) (99%, 0.133mol) were diazotized according to the diazotization method described in example-1 to give a diazonium salt solution for further use. 24.3g of naphthol AS-LC (IV) (99%, 0.067mol) and 17.87g of naphthol AS (V) were prepared in two beakers, respectively, according to the method for dissolving the coupling component AS described in example-11) (99%, 0.067mol) and acidified for use. Half of the diazonium salt was then coupled to the first coupling component IV following the coupling procedure described in example-1 to give a red suspension of Ia and the other half of the diazonium salt was coupled to the second coupling component V1Coupling gave a red suspension of Ib 1. The two suspensions are mixed and stirred uniformly, filtered, rinsed and pulped to form slurry with solid content of about 15%, and then the slurry is dried by a small laboratory spray dryer to obtain dark red powder 69.0g, the yield is 96.8%, the KD content in the product is 38ppm, and the arylamine content is 115 ppm.
Analysis and test:
1. and (3) testing the color performance of the product:
according to DIN6174, nitrocellulose is used as a connecting material, ethanol is used as a solvent, 2mm glass balls are used as a grinding body to prepare slurry with the pigment concentration of 15%, and the slurry is dispersed for 30 minutes by using a DASH200K dispersing instrument to obtain concentrated slurry. The pigment concentration of the thick color paste is diluted to 7.5 percent, a Gravurrephrotter 'laboratory' model is used for scraping to form a sample card, the sample card is dried at 60 ℃, the K/S, H and C values of the sample card are tested by a DataColor600, the glossiness is measured by a BDG515-TRI gloss instrument, the transparency is visually measured by comparing a black board and a white board, and the test result is shown in table-1.
2. Quantitative analysis of the fraction KD which is not diazotized in the product:
extracting the non-diazotized component KD in the product by using methanol under ultrasonic vibration, filtering, and carrying out HPLC quantitative detection on the filtrate by using SymmeryC 18 as a chromatographic column and acetonitrile as a mobile phase, and calculating the content by using an external standard method.
3. Quantitative testing of arylamine in the product:
according to DIN55610, the harmful aromatic amines in the pigment samples are extracted with hydrochloric acid at a concentration of 0.1M, the extracted aromatic amines are diazotized with sodium nitrite and coupled with R-salt to give colored substances, which are then quantitatively determined by spectrophotometry.
X-ray crystal powder diffraction analysis:
x-ray diffraction analysis (XRD) was carried out on a PANALYTICAL X' PERPRO type X-ray diffractometer using CuK α radiation (λ ═ 0.15418nm), operating voltage 40kV, operating current 40mA, diffraction angle scan range 2 θ ═ 10 to 80 °, and Jade6.0XRD data analysis software was used to analyze the sample diffraction peak position (diffraction angle 2 θ) and the corresponding interplanar spacing d
Although the invention has been described and illustrated in some detail by the inventor, it should be understood that modifications and variations to the above-described embodiments, or equivalent substitutions, will occur to those skilled in the art without departing from the spirit of the invention, and that the present terminology is used for the purpose of describing and understanding the embodiments of the invention, and is not intended to be limiting.
Claims (6)
1. A mixed crystal type naphthol AS organic pigment is characterized in that:
the mixed crystal form naphthol AS organic pigment I consists of two organic pigment molecules Ia and Ib, wherein R in Ib molecule1，R2And R3Can be one or more of alkyl, alkoxy, nitro, halogen or heterocycle, and the structure of IThe formula is as follows:
2. the preparation method of the mixed crystal form naphthol AS organic pigment according to claim 1, which is characterized by comprising the following steps:
the preparation method of I has three methods:
a. hybrid coupling method: diazotizing 3-amino-4-methoxybenzoyl aniline, and then carrying out coupling reaction on the diazotized 3-amino-4-methoxybenzoyl aniline, the coupling component 2 ', 5 ' -dimethoxy-4 ' -chloro-3-hydroxy-2-naphthoyl aniline of Ia and the coupling component naphthol AS and derivatives thereof of Ib in a mixture with a molar ratio of 100:1 to 1:1 in water in the presence of a surfactant with an HLB value of 15-18, and heating, filtering, rinsing, drying and grinding the obtained pigment suspension to obtain I;
b. coating coupling method: diazotizing 3-amino-4-methoxybenzoyl aniline, firstly coupling with a certain amount of coupling component naphthol AS of Ib and derivatives thereof in the presence of a surfactant with an HLB value of 15-18, then coupling with coupling component 2 ', 5 ' -dimethoxy-4 ' -chloro-3-hydroxy-2-naphthoyl aniline of Ia, and heating, filtering, rinsing, drying and grinding the obtained pigment suspension to obtain I;
c. a mixing and grinding method: diazotizing two parts of 3-amino-4-methoxybenzoyl aniline, then respectively mixing the diazotized two parts of 3-amino-4-methoxybenzoyl aniline with a coupling component of 2 ', 5 ' -dimethoxy-4 ' -chloro-3-hydroxy-2-naphthoyl aniline and a coupling component of naphthol AS for synthesizing Ib and derivatives thereof to prepare a suspension or a filter cake of Ia and Ib, then uniformly mixing the suspension or the filter cake according to a molar ratio of 100:1 to 1:1, grinding the mixture to a fineness of less than or equal to 40 mu m by using a colloid grinder, and heating, filtering, rinsing, drying and grinding the mixture to obtain I.
3. The preparation method of the mixed crystal form naphthol AS organic pigment according to claim 2, wherein the method comprises the following steps: the diazotization reaction for preparing the compound I is carried out in a water/inorganic acid medium, and the completeness of the diazotization is monitored by adopting thin-layer chromatography, so that the diazotization reaction is ensured to be complete, and the content of diazotization components in a final product is less than or equal to 100 ppm.
4. The preparation method of the mixed crystal form naphthol AS organic pigment according to claim 2, wherein the method comprises the following steps: the coupling reaction for preparation I is carried out in an acid-out solution of the coupling component. The coupling reaction is completely carried out by adopting the coupling assistant agent, the content of unreacted coupling components in the obtained pigment is low, the condition that the content of 4-chloro-2, 5-dimethoxyaniline in the product exceeds 150ppm due to hydrolysis of the coupling components in the post-process is avoided, and the safety of the product in human contact and food packaging application is ensured.
5. The preparation method of the mixed crystal form naphthol AS organic pigment according to claim 2, wherein the method comprises the following steps: the molar ratio of Ia to Ib in the I can be adjusted according to the needs, so that a rubiginous spectrum from a yellow phase to a blue phase is obtained, and different application requirements can be met.
6. The use of a mixed crystal form of a naphthol AS organic pigment according to claim 2, wherein: the three different preparation methods can obtain products which can meet different requirements of customers on product transparency; the mixing and coupling method can prepare a high-transparency product which is suitable for manufacturing packaging ink; the coating coupling method can prepare a product with moderate transparency, and is suitable for manufacturing digital ink jet; the mixing method can prepare relatively covered products, and is suitable for coloring plastics and special decorative materials.
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Cited By (1)
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| WO2023283932A1 (en) * | 2021-07-16 | 2023-01-19 | Clariant International Ltd. | Dispersants for the water-borne dispersion of pigments, composition thereof, and the method for preparing the same |
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| WO2023283932A1 (en) * | 2021-07-16 | 2023-01-19 | Clariant International Ltd. | Dispersants for the water-borne dispersion of pigments, composition thereof, and the method for preparing the same |
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