CN114634719A - Surface-modified pigments and their use - Google Patents
Surface-modified pigments and their use Download PDFInfo
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- CN114634719A CN114634719A CN202011484740.9A CN202011484740A CN114634719A CN 114634719 A CN114634719 A CN 114634719A CN 202011484740 A CN202011484740 A CN 202011484740A CN 114634719 A CN114634719 A CN 114634719A
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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
- C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
- C09B68/40—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the chemical nature of the attached groups
- C09B68/42—Ionic groups, e.g. free acid
- C09B68/423—Cationic groups
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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
- C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
- C09B68/20—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the process features
-
- 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
- C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
- C09B68/40—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the chemical nature of the attached groups
- C09B68/42—Ionic groups, e.g. free acid
- C09B68/425—Anionic groups
- C09B68/4253—Sulfonic acid groups
-
- 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
- C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
- C09B68/40—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the chemical nature of the attached groups
- C09B68/46—Aromatic cyclic groups
- C09B68/467—Heteroaromatic groups
- C09B68/4673—5-Membered rings
-
- 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
-
- 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
- C09D7/41—Organic pigments; Organic dyes
Abstract
The invention belongs to the technical field of fine chemical synthesis, and particularly relates to a modified coloring pigment containing benzothiazole organic groups and application of the pigment in an ink-jet ink composition. The surface modified pigment is a pigment having at least one organic group and at least one ionizable group on the surface. The modified pigments may be used in inkjet printers, coatings, paints, toners, color filters, or electrophoretic displays. The ink-jet ink of the present invention has excellent stability over a long period of time and a wide temperature range, and has desired viscosity and surface tension, and when printed, has good optical density, print definition, rub resistance, and water resistance.
Description
Technical Field
The invention belongs to the technical field of fine chemical synthesis, and particularly relates to a modified coloring pigment containing benzothiazole organic groups and application of the pigment in an ink-jet ink composition.
Background
Coloring pigments are widely used in many fields of industry with their excellent properties, but the particle size of commercially available coloring pigments has hindered the development of colored pigment preparations. The conventional approach to satisfying the small particle size of the colored pigment is generally to add a dispersant such as a surfactant, a polymer resin, or the like. The dispersant has two-sidedness in the process of preparing the coloring pigment with small particle size, and the stable existence of the pigment requires the existence of the dispersant and restricts the application of the pigment. If the dispersant may be incompatible with other inks, the addition of a large amount of dispersant may result in a decrease in the surface tension of the ink.
The pigment derivative has a skeleton structure similar to that of the pigment, has better affinity with the pigment, and derived substituent groups extend outwards, so that the electrical characteristics of the pigment and the affinity characteristics with a solvent and an auxiliary agent can be obviously changed; in addition, the pigment derivative exists as "impurity" and forms "alloy" with the original pigment, which microscopically changes the crystallization characteristic of the pigment and has the effects of refining crystal grains and improving apparent strength.
U.S. Pat. No. 5,876,628 discloses surface-modified colored pigments and aqueous compositions containing such surface-modified pigments which provide a considerable improvement in the stability of dyes or conventional pigment systems. US6506245 discloses ink jet inks containing coloured pigments and compositions thereof, the purpose of modifying the surface of the pigments being achieved by incorporating in the pigments sulfanilic acid, para aminobenzoic acid, N-para aminophenylpyridinium chloride, 3, 5-bis (trifluoromethyl) aniline. US6896726 discloses surface treated organic pigments comprising c.i. pigment red 255 modified by diazotized procaine and c.i. pigment blue 15:3 modified by diazotized hexadecylsulfonanilide. While these methods provide significant improvements in particle size and storage stability for modified pigments having attached organic groups, and are useful in a variety of applications such as inkjet inks, further improvements are needed.
In view of the excellent properties of pigment derivatives, there is still a need to develop more pigment derivatives for a wider range of applications.
Disclosure of Invention
In order to solve the above problems, the present invention aims to provide a modified colored pigment containing a benzothiazole organic group and use of the pigment in an inkjet ink composition.
In order to achieve the purpose, the invention adopts the technical scheme that:
a surface modified pigment, the surface modified pigment having at least one organic group and at least one ionizable group on the surface of the pigment.
The organic group is at least one aryl or arylene group. Further, the aryl group is a substituted phenyl group or a substituted naphthyl group.
The organic group aryl comprises at least one heterocyclic group attached.
The organo group aryl comprises at least one benzothiazole group attached.
The organic group benzothiazole contains at least one ionizable group which is a sulfonic acid group, a sulfonate salt, a carboxylic acid group or a carboxylate.
The surface modified pigment is prepared by connecting a primary amine compound diazonium salt containing an organic group to the surface of the pigment through a free radical reaction mode.
The primary amine compound diazonium salt containing organic groups is shown in a formula 1,
wherein the content of the first and second substances,
R1-R4may be the same or different and is selected from H or halogen; r5Is H, C1-C10Alkyl, sulfonic acid, carboxylic acid, sulfonate or carboxylate; r6Sulfonic acid group, carboxylic acid group, sulfonate or carboxylate.
The primary amine compound diazonium salt containing organic groups is
Preferably, M is Na or K.
The coloring pigment is pigment blue 15, pigment blue 16, pigment yellow 74, pigment yellow 155, pigment yellow 221, pigment red 122, pigment red 254 or pigment red 269.
The modified pigments may be used in inkjet printers, coatings, paints, toners, color filters, or electrophoretic displays.
Preparation of surface modified pigment:
1. sequentially adding primary amine containing benzothiazole groups, water and an alkali solution into a reaction vessel to enable the pH of the system to be 6-6.5, stirring and dissolving, adding hydrochloric acid, cooling in an ice water bath, slowly dropping a sodium nitrite solution, carrying out heat preservation reaction, and monitoring the reaction end point to obtain the diazonium salt.
The alkali solution is sodium hydroxide solution or potassium hydroxide solution.
The heat preservation reaction temperature is 0-10 ℃, and the reaction time is 1-2 h.
2. Adding pigment and water into a reactor, heating to raise the temperature for pre-dispersion, slowly adding the prepared diazonium salt solution, and adjusting the reactant to be neutral by using alkali after the reaction is finished. And then desalting and sanding to obtain the surface modified pigment.
The reaction temperature is 40-60 ℃, the pre-dispersion time is 2-4 h, and the sanding time is 10-18 h.
Wherein the molar ratio of the primary amine compound containing organic groups to water is 1: 40-50.
The invention has the following beneficial effects:
1. the surface modified dye prepared by the invention bonds a modifying group to the surface of the coloring pigment in a free radical reaction mode; the color of the modified colored pigment is basically consistent before and after modification, and the modified colored pigment can be easily dispersed in a required liquid carrier without adding a dispersing agent and has stable colloidal state. The indexes of the pigment color paste such as particle size distribution, conductivity, Zeta potential, surface tension, thermal storage and cold storage stability and the like can meet the requirements of the market on the pigment color paste, and the problems of large particle size, poor storage stability and the like commonly existing in similar products in the market are solved.
2. The ink-jet ink of the present invention has excellent stability over a long period of time and a wide temperature range, and has desired viscosity and surface tension, and when printed, has good optical density, print definition, rub resistance, and water resistance.
3. The pigments prepared according to the present invention can be used in ink jet printers, coatings, paints, toners, color filters, or electrophoretic displays.
Detailed Description
The following examples are presented to further illustrate the present invention, and it should be noted that the specific embodiments described herein are only intended to illustrate and explain the present invention and are not intended to limit the present invention.
The invention starts from pigment surface modification, researches on surface modification and nanocrystallization dispersion are carried out on representative pigment varieties such as pigment blue 15 (phthalocyanine), pigment red 122 (heterocycle), pigment yellow 74 (azo) and the like, and the nano-scale pigment color paste with excellent storage stability is prepared on the basis of not changing or slightly changing the color light of the pigment, so that the problems of large particle size, poor storage stability and the like commonly existing in similar products in the market are solved.
The parts referred to in the following examples are parts by weight, and are converted into pure product measurement except for the solution with the special indicated concentration, and the concentration unit is the weight percentage concentration. The methods employed for the pigment testing are well known and commonly used by those skilled in the art.
EXAMPLE 1 treatment of pigment blue 15:4 with 2- (4-aminophenyl) -6-methylbenzothiazole 7-sulphonic acid
1) Diazotization of 2- (4-aminophenyl) -6-methylbenzothiazole 7-sulphonic acid (Compound 1)
Adding 58g of 2- (4-aminophenyl) -6-methylbenzothiazole 7-sulfonic acid, 150ml of water and 40ml of 15% NaOH solution into a 500ml three-neck flask in sequence, stirring and dissolving, then adding 22ml of 30% hydrochloric acid, cooling to 0-5 ℃ in an ice water bath, slowly dropping 90ml of 140g/L sodium nitrite solution, keeping the temperature at 5 ℃ for reaction for 1h, detecting by using starch-KI test paper in the process, and keeping the nitrous acid in slight excess in the reaction liquid to prepare a compound 1 diazonium salt for later use.
2) Preparation of surface-modified organic pigments
70g of pigment blue 15:4 and 700ml of water are added into a 2L three-necked bottle, stirring is started, heating is carried out to 50 ℃, predispersion is carried out for 2H, the diazonium salt solution prepared in the step 1) is slowly added, the existence of the diazonium salt in a reaction mixture sample is detected by using an H-acid spot, the reaction liquid and the H acid are dripped on a filter paper, no red color is generated at the intersection, the reaction is carried out to the end point, and then the reactant is adjusted to be neutral by 15% of sodium hydroxide. The purified mill base dispersion was obtained by percolating 5 volumes of distilled water of the reactant until the conductivity of the mill base was less than 1500 μm/cm, and the solid content of the mill base dispersion was concentrated to 10%, followed by sanding for 10h to obtain a stable aqueous mill base dispersion of surface-modified phthalocyanine blue, and further, as a comparison, the pigment blue 15:4 was surface-modified by replacing 2- (4-aminophenyl) -6-methylbenzothiazole 7-sulfonic acid (compound 1) with sulfanilic acid according to the same procedure as in example 1. The results are as follows:
the results show that the pigment blue 15:4 pigment pastes modified with the diazonium salt of the compound 1 are equivalent to the pigment blue 15:4 pigment pastes modified with sulfanilic acid in terms of average particle size, viscosity, surface tension and the like.
Example 2 treatment of pigment yellow 74 with 2- (4-aminophenyl) -6-methylbenzothiazole 7-sulphonic acid diazonium salt
47g of pigment yellow 74, 600ml of water are placed in a 2L three-necked flask, stirred, heated to 56 ℃ and predispersed for 3H, the diazonium salt solution prepared in example 1) is slowly added, and the reaction mixture is neutralized with 15% sodium hydroxide after detection of the absence of diazonium salt in a sample of the reaction mixture by means of an H-acid spot. Percolating with 5 times volume of distilled water of reactant until the conductivity of the color paste is lower than 1500 μm/cm to obtain purified color paste dispersion, and concentrating the solid content of the color paste dispersion to 10%. Then sanding was performed for 10h to obtain a stable aqueous mill base dispersion of surface modified pigment yellow 74.
Example 3 surface treatment with 2- (4-aminophenyl) -6-methylbenzothiazole 7-sulfonic acid diazonium pigment Red 122.
41g of pigment Red 122, 800ml of water are placed in a 2L three-necked flask, stirred, heated to 45 ℃ with stirring, predispersed for 4 hours, the diazonium salt solution prepared in example 1) is slowly added, and the reaction mixture is neutralized with 15% sodium hydroxide after detection of the absence of diazonium salt in a sample of the reaction mixture by means of an H-acid spot. Percolating with 5 times volume of distilled water of reactant until the conductivity of the color paste is lower than 1500 μm/cm to obtain purified color paste dispersion, and concentrating the solid content of the color paste dispersion to 10%. The mill was then sanded for 18h to obtain a stable aqueous mill base dispersion of surface modified pigment Red 122. The results are shown in the following table:
the results show that treatment of the surfaces of pigment yellow 74 and pigment red 122 with the diazonium salt of Compound 1 effectively modifies the pigments thereof to obtain modified pigment dispersions having small average particle size, low viscosity, and high surface tension.
EXAMPLE 4 treatment of pigment blue 15:4 with 2- (3-chloro-4-aminophenyl) -6-methylbenzothiazole 7-sulfonic acid
1) Diazotization of 2- (3-chloro-4-aminophenyl) -6-methylbenzothiazole 7-sulphonic acid
Adding 64.6g of 2- (3-chloro-4-aminophenyl) -6-methylbenzothiazole 7-sulfonic acid, 160ml of water and 40ml of 15% NaOH solution into a 500ml three-neck flask in sequence, stirring and dissolving, then adding 22ml of 30% hydrochloric acid, cooling to 5-10 ℃ in an ice water bath, slowly dropping 90ml of 140g/L sodium nitrite solution, keeping the temperature at 10 ℃ for reaction for 2 hours, detecting by using starch-KI test paper during the reaction, and keeping the reaction liquid slightly excessive in nitrous acid to prepare a compound 2 diazonium salt for later use.
2) Preparation of surface-modified organic pigments
70g of pigment blue 15:4 and 700ml of water are added into a 2L three-necked bottle, stirring is started, heating is carried out to raise the temperature to 40-45 ℃, pre-dispersion is carried out for 3H, the diazo salt reaction solution of the compound 2 prepared in the step 1) is slowly added, and after the existence of no diazo salt in a reaction mixture sample is detected by using an H-acid spot, the reactant is adjusted to be neutral by using 15% of sodium hydroxide. Percolating the mixed solution with 5 times of distilled water until the conductivity of the color paste is lower than 1500 mu m/cm to obtain a purified color paste dispersoid, concentrating the solid content of the color paste dispersoid to 10 percent, and sanding the mixture for 15 hours to obtain the stable aqueous color paste dispersoid of the surface modified phthalocyanine blue.
Examples 5 and 6 treatment of pigment blue 15:4 with Compound 3, 4 diazonium salt
Pigment blue 15:4 was treated with the diazonium salt of compounds 3-4 according to the procedure of example 1, wherein the ratio of modifier to pigment was 1.5:1, and the test results are given in the following table:
the results show that the surface of pigment blue 15:4 is effectively modified by treating it with the diazonium salts of compound 2, compound 3 and compound 4, respectively, to obtain a modified pigment dispersion having a small average particle size, low viscosity and high surface tension.
Claims (9)
1. A surface modified pigment characterized by: the surface modified pigment is a pigment having at least one organic group and at least one ionizable group on the surface.
2. The surface-modified pigment of claim 1, wherein: the organic group is at least one aryl or arylene group.
3. A modified colored pigment according to claim 1, characterized in that: the organo group aryl comprises at least one benzothiazole group attached.
4. A modified colored pigment according to claim 1, characterized in that: the organic group benzothiazole at least contains one ionizable group, and the ionizable group is a sulfonic acid group, a sulfonate salt, a carboxylic acid group or a carboxylate.
5. A surface-modified pigment according to claim 1 or 2, characterized in that: the surface modified pigment is prepared by connecting a primary amine compound diazonium salt containing an organic group to the surface of the pigment through a free radical reaction mode.
6. The surface-modified pigment of claim 3, wherein: the primary amine compound diazonium salt containing organic groups is shown in a formula 1,
wherein
R1-R4May be the same or different and is selected from H or halogen; r5Is H, C1-C10Alkyl, sulfonic acid, carboxylic acid, sulfonate or carboxylate; r6Sulfonic acid group, carboxylic acid group, sulfonate or carboxylate.
7. The surface-modified pigment of claim 3, wherein: the primary amine compound diazonium salt containing organic groups is
Wherein M is H, K, Na or Li.
8. The surface-modified pigment of claim 1, wherein: the coloring pigment is pigment blue 15, pigment blue 16, pigment yellow 74, pigment yellow 155, pigment yellow 221, pigment red 122, pigment red 254 or pigment red 269.
9. The surface-modified pigment of claim 1, wherein: the modified pigments may be used in inkjet printers, coatings, paints, toners, color filters, or electrophoretic displays.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5837045A (en) * | 1996-06-17 | 1998-11-17 | Cabot Corporation | Colored pigment and aqueous compositions containing same |
| US5922118A (en) * | 1996-06-14 | 1999-07-13 | Cabot Corporation | Modified colored pigments and ink jet inks, inks, and coatings containing modified colored pigments |
| US6506245B1 (en) * | 1999-10-28 | 2003-01-14 | Cabot Corporation | Ink jet inks, inks, and other compositions containing colored pigments |
| CN1413236A (en) * | 1999-10-28 | 2003-04-23 | 卡伯特公司 | Ink jet inks, inks and other compositions containing colored pigments |
| CN1509319A (en) * | 2001-05-18 | 2004-06-30 | �������⻯ѧƷ�ع�����˾ | Surface-treated organic pigments |
-
2020
- 2020-12-16 CN CN202011484740.9A patent/CN114634719A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5922118A (en) * | 1996-06-14 | 1999-07-13 | Cabot Corporation | Modified colored pigments and ink jet inks, inks, and coatings containing modified colored pigments |
| US5837045A (en) * | 1996-06-17 | 1998-11-17 | Cabot Corporation | Colored pigment and aqueous compositions containing same |
| US6506245B1 (en) * | 1999-10-28 | 2003-01-14 | Cabot Corporation | Ink jet inks, inks, and other compositions containing colored pigments |
| CN1413236A (en) * | 1999-10-28 | 2003-04-23 | 卡伯特公司 | Ink jet inks, inks and other compositions containing colored pigments |
| CN101255284A (en) * | 1999-10-28 | 2008-09-03 | 卡伯特公司 | Ink jet inks, inks, and other compositions containing colored pigments |
| CN1509319A (en) * | 2001-05-18 | 2004-06-30 | �������⻯ѧƷ�ع�����˾ | Surface-treated organic pigments |
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