CN1705717A - Benzimidazolone compound - Google Patents

Abstract

A benzimidazolone compound is disclosed which has a plurality of hues in a single structural formula and good dispersibility in a binder resin and thus is useful as a pigment. The benzimidazolone compound is further useful as a pigment since it suffers little aggregation even when two or more kinds of the compound having different hues are used at the same time for obtaining an aimed hue. The benzimidazolone compound is represented by the following general formula (1): (wherein R<1>, R<2>, R<3> and R<4> independently represent a hydrogen atom, an alkyl group having 1-5 carbon atoms or an alkoxy group having 1-5 carbon atoms; and R<5> and R<6> independently represent an alkyl group having 1-5 carbon atoms).

Description

Benzimidazolone compound

Technical field

The present invention relates to benzimidazolone compound, it provides multiple color tones by the single structure formula, and can be as the pigment that good dispersion is provided in adhesive resin.

Require in the right of priority of the Japanese patent application 2003-182574 of submission on June 26th, 2003, its content in this combination as a reference.

Background technology

In comprising the conventional coating of dispersed color, according to the characteristic of pigment, the dispersion stabilization of difference can cause pigment flocculation, or the separation between pigment and the adhesive resin (hereinafter referred to as " varnish separation ").A kind of known method that addresses these problems comprises add pigment dispersing agent in coating.But though pigment dispersing agent has improved dispersing of pigments, they tend to reduce the weathering resistance and the thermotolerance of paint film, and if pigment dispersing agent be colored, it also may be difficult reaching the coating tone that needs so.

In addition, have under the coating situation of middle color, for example pigment has under the situation of coating of the middle color between redness and the yellow, must mix the pigment of different structure formula together, for example the diketopyrrolo-pyrrole base pigment of red coloration, quinacridine ketone group pigment, or diaminoanthraquinone-quinonyl pigment and xanchromatic azo-group pigment, isoindoline base pigment, or isoindoline ketone group pigment.

The coating that comprises the multiple pigment with different structure formula tends to easier pigment flocculation than the coating that only comprises a kind of pigment to be separated with varnish.In order to prevent this pigment flocculation, must in coating, add pigment dispersing agent.Optimum pigment dispersing agent is different for the pigment with different structure formula usually, mean comprise multiple pigment with different structure formula in the middle shade coating, use multiple pigment dispersing agent.But, may influence another kind of dispersing of pigments in the coating unfriendly for the optimal pigment dispersing agent of a kind of pigment, cause thus flocculating and the deterioration of dispersion stabilization.Therefore, under those situations, must consider employed real combination in conjunction with multiple pigment dispersing agent quite a lot ofly.

Also have the method that is producing middle shade coating, this method comprises mixing to have the analog structure formula but the pigment of multiple different tones.Have the analog structure formula but the example of the pigment of multiple different tone comprises: by the benzoglyoxaline keto compounds of formula (2) (hereinafter referred to as " compound (2) ") shown in following and formula (3) (hereinafter referred to as " compound (3) ") expression (referring to W.Herbst and K.Hunger, " IndustrialOrganic Pigments; for the second time complete revised edition " VCH Verlagsgesellschaft mbH, 1997, the 345 to 370 pages).

When molecular structure comprises naphthalene nucleus (above shown in compound (2) be red), these benzoglyoxaline keto compounds form red to the brown tinting pigment, when not comprising naphthalene nucleus (above shown in compound (3) be yellow) in the molecular structure, these benzoglyoxaline keto compounds form Yellow-to-orange tinting pigments.

But even in the coating by the similar compound (2) of hybrid structures and (3 and) preparation, pigment still tends to flocculation, reaches the tone that needs and becomes difficult.

Summary of the invention

An object of the present invention is to provide the benzimidazolone compound that comes from the single structure formula, it provides multiple color tones, and can be as the pigment that good dispersion is provided in adhesive resin, with benzimidazolone compound is provided, it can be used as pigment, and when two or more different tone pigment were mixed in together the tone that needs with preparation, it showed minimum flocculation.

In order to reach top described purpose, as intensive result of study, if promptly have the multiple different tone of compound exhibits of single structure formula based on this conception of species, the middle color that produces by mixed these different tones should suppress pigment flocculation so, the present inventor finds: have the benzimidazolone compound of introducing functional group, described functional group forms three 6 yuan of rings by intramolecular hydrogen bond action in two dimensional structure, even have the same structure formula, also can show multiple different tone.In addition, they also find: do not add pigment dispersing agent, under the situation of using single pigment of planting tone, under the situation of mixed pigment with different tones together, these benzimidazolone compounds can produce to have excellent stability and not to have the isolating coating of varnish.

In other words, the invention provides a kind of benzimidazolone compound by following general formula (1) expression:

(wherein, R ¹, R ², R ³And R ⁴The alkyl of independent separately expression hydrogen atom, 1 to 5 carbon atom, or the alkoxyl group of 1 to 5 carbon atom, and R ⁵And R ⁶The alkyl of representing 1 to 5 carbon atom independently of one another).

Even the benzimidazolone compound of expression also has superior dispersion stability not adding under the pigment dispersing agent, mean that their are ideal as the tinting pigment that is used for printing-ink, coating, the tinting material that is used for various plastics, toning agent, jetted ink and colour filter etc. by general formula (1).Radicals R in the wherein top general formula (1) ¹, R ², R ³And R ⁴All be hydrogen atom and radicals R ⁵And R ⁶All be the compound of methyl, though expression single structure formula, the variation according to determining in the crystalline structure shows multiple different tone, comprises bright-coloured redness, yellow, red-violet colour and blue red, is particularly preferred therefore.Because these pigment provide good inhibition to pigment flocculation, be single pigment of planting regardless of what use, two or more pigment with different tones that still mix use together are with color in the middle of producing, so they are very useful.

The accompanying drawing summary

Fig. 1 is the X-ray diffractogram of the alpha type crystal of the The compounds of this invention (1H) that obtains in embodiment 1.

Fig. 2 is the X-ray diffractogram of the β N-type waferN of the The compounds of this invention (1H) that obtains in embodiment 2.

Fig. 3 is the X-ray diffractogram of the γ N-type waferN of the The compounds of this invention (1H) that obtains in embodiment 3.

Fig. 4 is the X-ray diffractogram of the δ N-type waferN of the The compounds of this invention (1H) that obtains in embodiment 4.

Implement best mode of the present invention

Synthetic method 1

Can prepare the benzimidazolone compound of general formula (1), wherein R by following method ¹And R ⁴Represent identical group, and R ²And R ³Represent identical group: at acid sulfuric acid for example, under the existence of hydrochloric acid or phosphoric acid, under 150 to 180 ℃ temperature, at proton-less polarity solvent for example 1,3-dimethyl-2-imidazolone, methyl-sulphoxide, N, in dinethylformamide or the N-N-methyl-2-2-pyrrolidone N-, the compound (hereinafter referred to as " compound (4) ") of general formula (4) expression shown in making below 1 equivalent, the compound (hereinafter referred to as " compound (5) ") of the general formula shown in below 1 equivalent (5) expression, with 1 equivalent below shown in compound (hereinafter referred to as " compound (6) ") reaction of general formula (6) expression, reaction mixture uses usual method to filter to room temperature then, washing, drying and the sedimentary crystal of pulverizing.

(wherein, R ⁵And R ⁶The alkyl of representing 1 to 5 carbon atom independently of one another.)

(wherein, R ¹And R ²The alkyl of representing hydrogen atom, 1 to 5 carbon atom independently of one another, or the alkoxyl group of 1 to 5 carbon atom.)

(wherein, R ³And R ⁴The alkyl of representing hydrogen atom, 1 to 5 carbon atom independently of one another, or the alkoxyl group of 1 to 5 carbon atom.)

Synthetic method 2

Can prepare the benzimidazolone compound of general formula (1), wherein R by following method ¹And R ⁴Represent different groups, or R ²And R ³Represent different groups: with as above institute's synthetic method 1 under the identical reaction conditions, at first make 1 normal compound (4) and the reaction of 1 normal compound (5), then, make the reaction product and compound (6) reaction that obtain, the product that obtains of cooling is to room temperature then, uses that usual method filters, washing, dry and pulverize sedimentary crystal.

In compound, by the compound (hereinafter referred to as " compound (7) ") of the general formula (1) of formula (7) expression shown in following, wherein R by general formula (1) expression ¹, R ², R ³And R ⁴All represent hydrogen atom, and R ⁵And R ⁶All represent methyl, can prepare 4 kinds of different crystal types, alpha type crystal promptly described below, β N-type waferN, γ N-type waferN and δ N-type waferN have identical structural formula all, are preferred therefore.

(alpha type crystal)

(1) X-ray diffraction peak

Show the diffraction peak of Cu-K α characteristic X-ray when being 9.9 ± 0.2 °, 12.8 ± 0.2 °, 15.0 ± 0.2 ° and 25.0 ± 0.2 ° at Bragg angle 2 θ.

(2) tone

Bright-coloured redness.

(3) preparation method

Can use top described synthesis mode 1 preparation.

(β N-type waferN)

(1) X-ray diffraction peak

Show the diffraction peak of Cu-K α characteristic X-ray when being 14.3 ± 0.2 °, 16.6 ± 0.2 °, 24.2 ± 0.2 ° and 24.8 ± 0.2 ° at Bragg angle 2 θ.

(2) tone

Bright-coloured yellow.

(3) preparation method

Under 60 to 120 ℃ temperature, heat at N, the top alpha type crystal in the dinethylformamide, causing red crystals to change color gradually is yellow crystals.After heating at least 6 hours, to room temperature, use usual method filtration, washing and dried crystals by cooling mixture, can obtain the β N-type waferN.

(γ N-type waferN)

(1) X-ray diffraction peak

Show the diffraction peak of Cu-K α characteristic X-ray when being 9.9 ± 0.2 °, 14.3 ± 0.2 °, 16.3 ± 0.2 °, 24.5 ± 0.2 ° and 26.0 ± 0.2 ° at Bragg angle 2 θ.

(2) tone

Bright-coloured red-violet colour.

(3) preparation method

Can be by the following γ of obtaining N-type waferN: use the equipment from mechanical shear stress to mixture for example ball mill, attritor (atriter), vibration mill or the kneader that apply, grind and mixed above alpha type crystal with as the water-soluble inorganic salt of grinding medium for example sodium-chlor or sodium sulfate, with liquid honing auxiliary agent glycol ether for example, then use dissolving grinding medium and liquid honing auxiliary agent but do not dissolve the crystalline solvent, the mixture that peptization grinds uses usual method filtration, washing, dry and pulverizing crystal then.

(δ N-type waferN)

(1) X-ray diffraction peak

Show the diffraction peak of Cu-K α characteristic X-ray when being 12.8 ± 0.2 °, 15.8 ± 0.2 °, 25.0 ± 0.2 ° and 26.5 ± 0.2 ° at Bragg angle 2 θ.

(2) tone

Bright-coloured is blue red.

(3) preparation method

Can be by the following δ N-type waferN that obtains: alpha type crystal, β N-type waferN or γ N-type waferN above the dissolving be in the vitriol oil, solution is poured in the frozen water, deposit again, therefore deposit blue red crystals, filter blue red colored slurries then, use usual method washing, dry and pulverizing crystal.

Four kinds of crystal types recited above have the not more detailed understanding of reason of different tones mutually, but can infer that following factor is important.

Compound (7) comprises an aromatic monocyclic in structure centre.If the carbonyl of two amino that are connected with this aromatic ring and two carboxylicesters groups forms intramolecular hydrogen bonds, form a kind of like this structure so, be arranged in order (referring to following formula (8)) comprising three 6 yuan of rings of center aromatic ring.Represent chromophoric group by the plane that these three 6 yuan rings form, and think to form generation red basic crystalline reason (alpha type crystal, γ N-type waferN and δ N-type waferN).

In addition, think that tone different reason between alpha type crystal, γ N-type waferN and δ N-type waferN is due to the fact that, promptly by the variation of angle in the different crystal type between the plane of the plane that three 6 yuan of center aromatic ring rings form comprising of forming of the result as the intramolecular hydrogen bond effect and benzoglyoxaline ketone groups, this is the result who rotates on every side at the key by the expression of the arrow " A " in the top formula (8).

On the other hand, think if the intramolecular hydrogen bond that forms between the carbonyl of two amino and two carboxylic acid ester groups is heated destruction in organic solvent, form the chromophoric planar molecular moiety of expression at minute subcenter so and be reduced to just center aromatic ring, mean that it disappears as chromophoric contribution, therefore produce the crystal (β N-type waferN) of yellow tone.

Embodiment

Based on a series of embodiment, the present invention is described in more detail below.Except as otherwise noted, the unit among the embodiment " part " and " % " are meant the weight reference value.

Embodiment 1

To 750 parts 1, in 3-dimethyl-2-imidazolone, add 43.6 parts the amino benzimidazolone of 5-, 30 parts dimethyl succinyl succinate and 13.4 parts the vitriol oil, and the mixture that obtains 180 ℃ of heating 14 hours.Then be cooled to room temperature, the filter deposition thing, with 200 parts 1, the washing with acetone of 3-dimethyl-2-imidazolone and 600 parts, to remove impurity, under 110 ℃ of decompressions dry 8 hours then, therefore obtain the bright-coloured red colored alpha type crystal of 17.7 parts (productive rates 28%).When analyzing these red alpha type crystals, obtain following result by infrared spectra and field desorption(FD) mass spectrum (FD-MS).Infrared spectra

The Infrared spectroscopy that the Fourier transform infrared line spectrophotometer FT/IR-550 that use is prepared by Jasco Corporation carries out shows because the absorption peak that following stretching vibration causes:

3200cm ^-1: at the N-H stretching vibration of imidazolone intra-annular amide group

1720cm ^-1: the C=O stretching vibration of methyl ester.

1695cm ^-1: at imidazolone intra-annular C=O stretching vibration.

1220cm ^-1: the C-O stretching vibration of methyl ester.

Field desorption(FD) mass spectrum (FD-MS)

The field desorption(FD) mass spectrometric detection that use is undertaken by (bi-focal type) gas chromatograph mass spectrograph GCMS 9100MK of Shimadzu Corporation preparation is at molecular weight being molecular ion peak in 488.

The result of last surface analysis determines that the red alpha type crystal that obtains is the crystal of compound recited above (7) in embodiment 1.

In addition, use under the X-ray diffractometer RINT Ultima+ and condition below by Rigaku Corporation preparation, equally the alpha type crystal that obtains is used the powder x-ray diffraction analysis of Cu-K α x-ray bombardment in embodiment 1.

Power: 40kV, 30mA

Sampling angle: 0.020 °

Disperse/scatter slit: (1/2)

Emission slit: 0.3mm

Sweep velocity: 2 °/minute

The X-ray diffraction pattern that obtains from top powder x-ray diffraction analysis is shown in Fig. 1.The red alpha type crystal of compound (7) shows the diffraction peak of Cu-K α characteristic X-ray when being 9.9 ± 0.2 °, 12.8 ± 0.2 °, 15.0 ± 0.2 ° and 25.0 ± 0.2 ° at Bragg angle 2 θ.

Embodiment 2

To 10 parts N, add 2 parts of red alpha type crystals that obtain in an embodiment in the dinethylformamide, and 90 ℃ of heated mixt 6 hours.The mixture that obtains of cooling filters slurries to room temperature then, and with 50 parts washing with acetone, the dry settling that obtains 8 hours under 110 ℃ of decompressions then, so obtain the bright-coloured yellow coloring β N-type waferN of 1.6 parts (productive rates 80%).

Use with for obtaining the described same procedure of red alpha type crystal among the embodiment 1, by these yellow β N-type waferNs of powder x-ray diffraction analysis.The X-ray diffraction pattern that obtains is shown among Fig. 2.Show that this crystal is different with alpha type crystal, and show the diffraction peak of Cu-K α characteristic X-ray when being 14.3 ± 0.2 °, 16.6 ± 0.2 °, 24.2 ± 0.2 ° and 24.8 ± 0.2 ° at Bragg angle 2 θ.

Embodiment 3

Mixed together 15 parts of red alpha type crystals that in embodiment 1, obtain, 150 parts salt and 37.5 parts glycol ether, and in kneader, grind.At the molten mixture that obtains of 1000 parts 60 ℃ water-borne glue, then filter then.Repeated washing process 3 times in this washing process, at the molten wet cake that obtains thus of 1000 parts 60 ℃ water-borne glue, is filtered then.Wet cake after the dry washing that obtains under 110 ℃ of decompressions is 8 hours then, therefore obtains the painted γ N-type waferN of bright-coloured red-violet colour of 13.5 parts (productive rates 90%).

Use with for obtaining the described same procedure of red alpha type crystal among the embodiment 1, by these yellow β N-type waferNs of powder x-ray diffraction analysis.The X-ray diffraction pattern that obtains is shown among Fig. 3.Show that this crystal is different with alpha type crystal, and show the diffraction peak of Cu-K α characteristic X-ray when being 9.9 ± 0.2 °, 14.3 ± 0.2 °, 16.3 ± 0.2 °, 24.5 ± 0.2 ° and 26.0 ± 0.2 ° at Bragg angle 2 θ.

Embodiment 4

In 10 parts of vitriol oils (vitriolic concentration is at least 95%), dissolve the red alpha type crystal that obtains among 2 parts of embodiment 1.Then, in 100 parts of water, pour into the sulphuric acid soln that obtains, so deposit red crystal and generation slurries.Filter slurries, the water repeated washing becomes neutrality up to filtrate then.Wet cake after the dry washing that obtains under 110 ℃ of decompressions is 8 hours then, therefore obtains the red colored δ N-type waferN of bright-coloured indigo plant of 1.8 parts (productive rates 90%).

Use with for obtaining the described same procedure of red alpha type crystal among the embodiment 1, by these yellow β N-type waferNs of powder x-ray diffraction analysis.The X-ray diffraction pattern that obtains is shown among Fig. 4.Show that this crystal is different with alpha type crystal, and show the diffraction peak of Cu-K α characteristic X-ray when being 12.8 ± 0.2 °, 15.8 ± 0.2 °, 25.0 ± 0.2 ° and 26.5 ± 0.2 ° at Bragg angle 2 θ.

Each the diffraction peak of color harmony Cu-K α characteristic X-ray for 4 kinds of crystal types that obtain among the embodiment 1 to 4 in the above is summarised in the following table 1.

Table 1

Crystal type	The α type	The β type	The γ type	The δ type
					Tone	Red	Yellow	Red-violet colour	Blue red
Cu-K α characteristic X-ray peak (± 0.2 °)	??9.9° ??12.8° ??15.0° ??25.0°	??14.3° ??16.6° ??24.2° ??24.8°	??9.9° ??14.3° ??16.3° ??24.5° ??26.0°	??12.8° ??15.8° ??25.0° ??26.5°

Embodiment 5

Dimethylbenzene at 12 parts: just-butanols=7: 3 mixed solvent in, dissolve 66 parts mixed resin, it comprises 70% baking finish Synolac (ProductName: Beckosol J-524-IM-60, by Dainippon Ink and Chemicals, Incorporated preparation) and 30% melamine resin (ProductName: Super Beckamine G-821-60, by Dainippon Ink and Chemicals, the Incorporated preparation), therefore obtain binder resin solution.

In 78 parts this binder resin solution, add 2 parts of alpha type crystals that in embodiment 1, obtain, shake and dispersed mixture 2 hours at the coating conditioner, obtain coating (1) thus.

Embodiment 6

Except the alpha type crystal that replaces using among the embodiment 5 with the β N-type waferN that obtains among the embodiment 2, prepare coating (2) in the mode identical with embodiment 5.

Embodiment 7

The coating (2) that obtains among the coating (1) that obtains among mixed together 5 parts of embodiment 5 and the 5 parts of embodiment 6 forms 10 parts mixed coating (1).

Comparative example 1

Except using red pigment (trade(brand)name: Irgazin DPP Red BO (C.I. Pigment red 254), prepare by CibaSpecialty Chemicals Corporation, be designated hereinafter simply as DPP-BO) outside the alpha type crystal that replaces using among the embodiment 5, prepare coating (3) in the mode identical with embodiment 5.

Comparative example 2

Except using red pigment (trade(brand)name: Novoperm Red HFT (C.I. Pigment red 175), prepare by Clariant Japan K.K., be equivalent to compound recited above (2), be designated hereinafter simply as HFT) outside the alpha type crystal that replaces using among the embodiment 5, prepare coating (4) in the mode identical with embodiment 5.

Comparative example 3

Except using yellow ultramarine (trade(brand)name: Symuler Fast Yellow 4192 (C.I. pigment yellow 154), by Dainippon Ink and Chemicals, the Incorporated preparation, be equivalent to compound recited above (3), be designated hereinafter simply as 4192) outside the alpha type crystal that replaces using among the embodiment 5, prepare coating (5) in the mode identical with embodiment 5.

Comparative example 4

The coating (5) that obtains in the coating (3) that obtains in mixed together 5 parts of comparative examples 1 and the 5 parts of comparative examples 3 forms 10 parts mixed coating (2).

Comparative example 5

The coating (5) that obtains in the coating (4) that obtains in mixed together 5 parts of comparative examples 2 and the 5 parts of comparative examples 3 forms 10 parts mixed coating (3).

The assessment of coating flocculation

Every kind of coating for preparation in top embodiment 5 to 7 and the comparative example 1 to 5, use is by Nikkiso Co., and the Microtrac Particle Size Analyzer UPA150 of Ltd. preparation measures after the preparation volume averaging granular size of the pigment in immediately the coating.In addition, also measure the volume averaging granular size of the pigment in every kind of coating at room temperature placing after 1 day in the same way.In addition, the value by pigment volume mean particle size in immediately the coating after the preparation deducts the value of at room temperature placing the pigment volume mean particle size after 1 day, also calculates the difference (Δ mean particle size) of the volume averaging granular size of every kind of coating.Based on following evaluation criteria, the value of Δ mean particle size is used for assessing the flocculation level.

A: the Δ mean particle size is lower than 0.20 μ m, B: the Δ mean particle size is at least 0.20 μ m

The isolating assessment of coating varnish

In transparent glass sample bottle, put into every kind of coating sample of top embodiment 5 to 7 and comparative example 1 to 5 preparation, and allow at room temperature to place for 2 weeks.The isolating sign of visual control sample varnish (cause producing at the top of coating sample the transparent resin solution layer separating of pigment and resin solution) then.Based on following evaluation criteria, will obtain the result and be used for assessing the varnish separation.

A: do not observe varnish and separate B: observe varnish and separate

The assessment result of every kind of coating of preparation is summarised in the table 2 in top embodiment 5 to 7 and the comparative example 1 to 5.

Table 2

	Embodiment 5	Embodiment 6	Embodiment 7	Comparative example 1	Comparative example 2	Comparative example 3	Comparative example 4	Comparative example 5
									Coating	Coating (1)	Coating (2)	Mixed coating (3)	Coating (3)	Coating (4)	Coating (5)	Mixed coating (2)	Mixed coating (3)
Pigment	Alpha type crystal	The β N-type waferN	α and β N-type waferN	??DPP-BO	??HFT	??4192	??DPP-BO ??4192	??HFT ??4192
									Immediately pigment mean particle size (μ m) after the preparation	??0.97	??1.49	??1.26	??1.14	??0.87	??1.55	??1.44	??1.89
Place the pigment mean particle size (μ m) after 1 day	??0.95	??1.34	??1.25	??1.37	??1.20	??1.81	??1.65	??2.45
									Δ mean particle size (μ m)	??-0.02	??-0.15	??-0.01	??0.23	??0.33	??0.26	??0.21	??0.56
The coating flocculation	??A	??A	??A	??B	??B	??B	??B	??B
									Coating varnish separates	??A	??A	??A	??B	??B	??B	??B	??B

From the result shown in the table 2, carry out following observation.

Result from embodiment 5 and 6 is apparent that, when alpha type crystal that uses benzimidazolone compound of the present invention in coating separately or β N-type waferN, flocculation both occurred and the varnish separation also do not occurred.

Result from embodiment 7 is apparent that, when the coating and the coating of the β N-type waferN that comprises benzimidazolone compound of the alpha type crystal that comprises benzimidazolone compound of the present invention are mixed, flocculation have both occurred and the varnish separation also do not occurred.

Result from comparative example 1,2 and 3 is apparent that, uses separately conventional pigment for example DPP-BO, HFT or in coating at 4192 o'clock, flocculation occurs and separates with varnish.

Result from ratio example 4 is apparent that, when coating that comprises conventional pigment DPP-BO (3) and the coating (5) that comprises pigment 4192 are mixed, flocculation occur and separates with varnish.

Comparative example 5 expression such an embodiment, the coating (4) that wherein comprises conventional pigment HFT is mixed with the coating (5) that comprises pigment 4192, it has the similar structural formula with HFT, but is clear that, has still occurred pigment flocculation in this embodiment and has separated with varnish.In addition, the interior pigment mean particle size of coating (4) that comprises pigment HFT is 0.87 μ m, the interior pigment mean particle size of coating (5) that comprises pigment 4192 is 1.55 μ m, the result, what expect is pigment mean particle size in mixed coating (3), described mixed coating (3) comprises the mixture of these two kinds of coating equivalent, will be the mean value of these two kinds of mean particle sizes, i.e. 1.21 μ m.But immediately the observed value of mean particle size was 1.89 μ m after two kinds of coating were mixed, indicated that pigment flocculation occurs after two kinds of coating are mixed immediately.

Industrial usability

The present invention even the benzimidazolone compound of expression also has excellent dispersion stabilization not adding under the pigment dispersing agent, means that their are desirable as the coloring pigment that is used for printing-ink, coating, the colouring agent that is used for various plastics, toner, jetted ink and colour filter etc. by general formula (1). The radicals R in the top general formula (1) wherein¹、R ²、R ³And R⁴All be hydrogen atom and radicals R⁵And R⁶All be the compound of methyl, although expression single structure formula, the variation according to determining in the crystal structure shows multiple different tone, comprises bright-coloured redness, yellow, reddish violet and blue red, is particularly preferred therefore. Because these pigment provide good inhibition to pigment flocculation, be single pigment of planting regardless of what use, still mix together two or more pigment with different tones of use with color in the middle of producing, so they are very useful.

Claims (6)

1. benzimidazolone compound by the expression of the general formula (1) shown in following:

(wherein, R ¹, R ², R ³And R ⁴The alkyl of independent separately expression hydrogen atom, 1 to 5 carbon atom, or the alkoxyl group of 1 to 5 carbon atom, and R ⁵And R ⁶The alkyl of representing 1 to 5 carbon atom independently of one another).

2. according to the benzimidazolone compound of claim 1, wherein in described general formula (1), R ¹, R ², R ³And R ⁴All represent hydrogen atom, and R ⁵And R ⁶All represent methyl.

3. according to the benzimidazolone compound of claim 2, it shows the diffraction peak of Cu-K α characteristic X-ray when Bragg angle 2 θ are 9.9 ± 0.2 °, 12.8 ± 0.2 °, 15.0 ± 0.2 ° and 25.0 ± 0.2 °.

4. according to the benzimidazolone compound of claim 2, it shows the diffraction peak of Cu-K α characteristic X-ray when Bragg angle 2 θ are 14.3 ± 0.2 °, 16.6 ± 0.2 °, 24.2 ± 0.2 ° and 24.8 ± 0.2 °.

5. according to the benzimidazolone compound of claim 2, it shows the diffraction peak of Cu-K α characteristic X-ray when Bragg angle 2 θ are 9.9 ± 0.2 °, 14.3 ± 0.2 °, 16.3 ± 0.2 °, 24.5 ± 0.2 ° and 26.0 ± 0.2 °.

6. according to the benzimidazolone compound of claim 2, it shows the diffraction peak of Cu-K α characteristic X-ray when Bragg angle 2 θ are 12.8 ± 0.2 °, 15.8 ± 0.2 °, 25.0 ± 0.2 ° and 26.5 ± 0.2 °.

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