CN1927953A - Pigment dispersant and pigment composition, pigment dispersion and printing ink using the same - Google Patents
Pigment dispersant and pigment composition, pigment dispersion and printing ink using the same Download PDFInfo
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- CN1927953A CN1927953A CN 200510098426 CN200510098426A CN1927953A CN 1927953 A CN1927953 A CN 1927953A CN 200510098426 CN200510098426 CN 200510098426 CN 200510098426 A CN200510098426 A CN 200510098426A CN 1927953 A CN1927953 A CN 1927953A
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Abstract
The present invention provides one kind of pigment dispersant. The pigment dispersant is used in printing ink and paint, and can reach excellent flowability, high dispersion stability, capacity of forming bright coating, etc. The pigment dispersant has the structure as shown.
Description
Technical field
The present invention relates to pigment dispersing agent, more particularly, the present invention relates to contain color compositions, pigment dispersion and the printing-ink of pigment dispersing agent.
Background technology
In printing-ink, coating etc.,, can make printed matter or application fabricated product have distinct adaptability such as color harmony gloss with the micro situation dispersed color.In addition,, can improve the flowability of printing-ink and coating, improve printing adaptability, reduce the labour and the energy when making printing-ink and coating significantly by with the stable status dispersed color.And then, if dispersion is in stable condition, general stability in storage excellence.
In fact the pigment that is used for printing-ink and coating, in order to realize distinct more tone, particle diameter is very tiny mostly.But if particle is too tiny, the cohesive force between pigment particles strengthens, and often is difficult to have above-mentioned adaptability.
In order to solve such problem, knownly can use pigment dispersing agent, make the affinity of pigment and vehicles become well, realize the stabilization of dispersion.Various pigment dispersing agents are disclosed up to now.
For example, disclose in special public clear 41-2466 communique and the US2855403 communique, used with pigment dyestuff and import the compound that substituting groups such as sulfonic acid, sulfonamido, amino methyl, phthalimidomethyl obtain as precursor skeleton and at side chain.Though these compounds are bigger for the effect of the non-compendency of pigment, crystallization-stable etc., owing to have the character that is similar to dyestuff, so compare poor durability sometimes with pigment.Therefore, when the color compositions that contains these compounds was used for printing ink and coating, sometimes along with the continuity of time, the color of compound can disappear and take off, and causes the tonal variation of filming.In addition, form film after, sometimes because of boil, high temperature such as baking handles and crimping, these compound emersions and mobile (migration) that produce tone.
In addition, the spy opens in flat 8-127749 communique and the flat 11-199796 communique of Te Kai, and as the measure that addresses these problems, disclosing does not have pigment peculiar painted and contain the triazine ring basic cpd for what various pigment had a versatility.But,, then can not show effect of sufficient when containing naphthols pigment and azo condensation pigment in the pigment though the tackiness agent that these compounds have an acidic functionality with acrylic resin or Synolac etc. demonstrates effect when using.In addition, when using urethane resin or polyamide resin etc. to have the tackiness agent of basic functionality, basic display does not go out effect.Especially use be used to gravure inks etc. contain the alkaline high urethane resin of urea key the time, can not show effect fully.
That is, wish development, develop a kind of when being used for printing-ink or coating flowability, dispersion stabilization and the excellences such as gloss when forming dry film, especially to naphthols pigment and the effective pigment dispersing agent of azo condensation pigment.
Summary of the invention
Embodiments of the present invention relate to the pigment dispersing agent with following general formula (1) expression.
General formula (1):
In the formula, R
1, R
2, R
3, R
4, R
5, R
6, R
7, R
8, R
9And R
10Independent separately expression-H ,-Cl ,-CH
3,-CF
3,-NO
2,-COOCH (CH
3)
2,-COOCH
2CH
2Cl.R
11, R
12, R
13And R
14Independent separately expression-H ,-Cl ,-CH
3,-CN.M represents the monovalent of divalence or tervalent metal.N represents 1～3 integer.
In addition, embodiments of the present invention relate to the color compositions of the pigment dispersing agent that contains at least a pigment selected and above-mentioned general formula (1) from naphthols pigment and azo condensation pigment.Can contain the resin type pigment dispersing agent as required in the color compositions, its weight-average molecular weight is preferably 1000～100000.
And then embodiments of the present invention relate to above-mentioned color compositions are dispersed in pigment dispersion in the vehicles.Can enumerate non-aqueous and the water-based vehicles as vehicles.
It is 5000～100000 resin that non-aqueous vehicles can contain weight-average molecular weight, and this resin can be the urethane resin that has at least one urea key at an intramolecularly.
And then embodiments of the present invention relate to the printing-ink that contains pigment dispersion.
According to the embodiment of the present invention, can obtain not only non-compendency, amorphism, mobile excellent, and the gloss of filming, the also extraordinary printing ink of tone and coating.
Embodiment
Below, explain the present invention.
Embodiments of the present invention relate to the pigment dispersing agent with following general formula (1) expression.
General formula (1):
In the formula, R
1, R
2, R
3, R
4, R
5, R
6, R
7, R
8, R
9And R
10Independent separately expression-H ,-Cl ,-CH
3,-CF
3,-NO
2,-COOCH (CH
3)
2,-COOCH
2CH
2Cl.R
11, R
12, R
13And R
14Independent separately expression-H ,-Cl ,-CH
3,-CN.M represents the monovalent of divalence or tervalent metal.N represents 1～3 integer.
R
1～R
5In, be preferably be no more than two at most and be-Cl or-CF
3, all the other are-H.
R
6～R
10In, be preferably be no more than two at most and be-Cl or-CF
3, all the other are-H.
R
11～R
14Be preferably-H, perhaps be no more than two at most and be-Cl.
The preferred compound of general formula (1) can be enumerated following compound.
The pigment dispersing agent of general formula (1) is to import sulfonic acid in azo condensation pigment, and this sulfonic acid is become the material of metal-salt.
Azo condensation pigment as the pigment dispersing agent that is used for synthetic general formula (1), be not limited to following example, if but represented concrete example with the generic name of Colour Index, then could enumerate Pigment red 144,166,214,220,221,242,248,262, pigment brown 23,42 etc.
The metal M that contains in the formula of general formula (1) for example can be enumerated calcium, barium, magnesium, iron, aluminium, nickel, cobalt, strontium etc., but is not limited to these examples.Wherein, be preferably aluminium.The substituting group quantity n of sulfonic acid is 1～3, exists the different pigment dispersing agent of n also to have no relations even mix.If the substituting group quantity of sulfonic acid then not only can't obtain effect of sufficient more than or equal to 4, and the tendency that exists transport property to worsen.Use the substituting group quantity of average substituting group quantitaes sulfonic acid sometimes, average substituting group quantity is preferably 1～2.
The manufacture method of the pigment dispersing agent of general formula (1) can be enumerated as follows as an example.
At first, azo condensation pigment is dissolved in the vitriol oil.Under normal temperature or heated condition, this sulphuric acid soln is carried out sulfonation.Then, the frozen water that this sulphuric acid soln is injected q.s is made suspension.This suspension is filtered, washes, the filter cake that obtains being sulfonated.Water or organic solvent will be made slurry by the filter cake that aforesaid operations obtains, the metal strong acid salt powder or the aqueous solution of volumetric molar concentrations such as interpolation once more.Described strong acid salt for example can be enumerated hydrochloride, vitriol, nitrate etc., but is not limited to these examples.Then stir, filter then, washing, drying, the metal salt compound that just can obtain by general formula (1) expression is a pigment dispersing agent.
The pigment dispersing agent of general formula (1) is usually to being used for the various pigment performance effects of printing-ink or coating, especially for naphthols pigment and the excellent effect of azo condensation pigment performance.As naphthols pigment, if the generic name with Colour Index is represented concrete example, can enumerate Pigment red 2,3,5,7,9,12,14,22,23,31,112,146,170,171,175,176,185, pigment orange 5,24,38, pigment brown 25, pigment violet 32 etc., but be not limited to these examples.In addition, as azo condensation pigment,, can enumerate Pigment red 144,166,214,220,221,242,248,262, pigment orange 31, pigment brown 23,41,42 etc., but be not limited to these examples if represent concrete example with the generic name of Colour Index.
Color compositions of the present invention is the color compositions that the pigment dispersing agent of general formula (1) expression is used in independent interpolation or the pigment dispersing agent of general formula (1) expression is used in interpolation under the situation of also using the resin type pigment dispersing agent in pigment.
The resin type pigment dispersing agent that is used for color compositions of the present invention, the straight chain shape or the comb form height molecule multipolymer that are preferably by polyester, acrylic acid or the like, polyurethanes constitute.Also have, the resin type pigment dispersing agent is preferably in the matrix position of end at straight-chain polymer, comb shape polymkeric substance or the two kinds of polymkeric substance block or contains basic group, acidic-group, aromatic group etc. disorderly.This pigment dispersing agent has opened the spy that clear 60-166318 communique, spy are opened clear 61-174939 communique, the spy opens in clear 46-7294 communique and the flat 9-169821 communique of Te Kai etc. and discloses.
The weight-average molecular weight of resin type pigment dispersing agent is advisable 1000～100000, is preferably 5000～50000.If less than 1000, can't obtain enough sterically hinderedly, reduce dispersion effect sometimes.In addition, if weight-average molecular weight greater than 100000, can produce agglutination on the contrary.
The amine value of resin type pigment dispersing agent is advisable at 5～200mgKOH/g, if less than 5mgKOH/g, will be insufficient with the interaction of pigment dispersing agent of the present invention, even pigment dispersing agent of the present invention is adsorbed on the surface of pigments, also can not get sufficient dispersion effect sometimes.On the other hand, if the amine value of pigment dispersing agent surpasses 200mgKOH/g, then compare with affine portion for pigment composition, sterically hindered layer can reduce, and can't obtain sufficient dispersion effect.
This resin type pigment dispersing agent can be a product sold on the market, for example can enumerate Solsperse 24000 (ア PVC シ ア system), Disperbyk-160, Disperbyk-161, Disperbyk-162, Disperbyk-163, Disperbyk-170 (PVC Star Network ケ ミ one society's system), ア ジ ス パ one PB711, ア ジ ス パ one PB821 (monosodium glutamate Off ア イ Application テ Network ノ Co., Ltd. system) etc., but be not limited to these examples.
With respect to pigment 100 weight parts, be advisable in 0.5～30 weight part scope with the addition of the pigment dispersing agent of general formula (1) expression, be preferably 1～10 weight part.With respect to pigment 100 weight parts, the addition of resin type pigment dispersing agent is advisable in 0.5～100 weight part scope, is preferably 5～30 weight parts.
With general formula (1) if the pigment dispersing agent of expression and the addition of resin type pigment dispersing agent separately less than 0.5 weight part, then the colo(u)rant dispersion effect is little.In addition, use general formula (1) if the addition of the pigment dispersing agent of expression greater than 30 weight parts, also can not get the component corresponding effects of using.If the addition of resin type pigment dispersing agent greater than 100 weight parts, not only can not get effect, and the rerum natura of filming descends sometimes.
Pigment dispersing agent of the present invention is dispersed in the vehicles can obtains pigment dispersion.The dispersing method example has following method.
1. pigment and pigment dispersing agent are pre-mixed, resulting color compositions are added to making it in the vehicles to disperse.
2. in vehicles, add pigment respectively and pigment dispersing agent disperses.
3. in vehicles, distinguish dispersed color and pigment dispersing agent in advance, resulting dispersion is mixed.At this moment, can only use the solvent dispersion pigment dispersing agent.
4. in vehicles, behind the dispersed color, in the pigment dispersion that obtains, add pigment dispersing agent.
Adopt any above method can obtain desired effects.
As the modulator approach of color compositions, can obtain sufficient dispersion effect as long as pigment powder and pigment dispersing agent of the present invention just mixed simply.In order to obtain better result, can adopt kneader, Rolled machine, attritor, horizontal sand mill, various pulverizers etc. to carry out mechanically mixing; In the water of pigment or organic solvent suspension system, add the solution that contains pigment dispersing agent of the present invention, pigment dispersing agent is deposited on the surface of pigments; Perhaps, have at sulfuric acid etc. and to dissolve pigment dyestuff and pigment dispersing agent in the strong solvent solvent altogether, utilize lean solvents such as water to make it co-precipitation; Etc. sufficient blending means.
In addition, can use dispersing apparatus that pigment or pigment dispersing agent are disperseed, are blended in non-water system or water system vehicles or the solvent.Described dispersing apparatus can be enumerated dissolver, high-speed mixer, homogenizing mixing machine, kneader, Rolled machine, sand mill, attritor, but is not limited to these examples.Dispersed color well thus.
In the pigment dispersion that contains non-water system vehicles, to compare with the situation of independent use pigment, when using the pigment dispersing agent of general formula (1), the viscosity degradation of dispersion and structural viscosity reduce, and demonstrate good flowability.In addition, there are not problems such as loose colour, crystallization variation in printing-ink of the present invention and coating, and printed matter or the gloss of filming are good, can obtain goods attractive in appearance.
Pigment dispersing agent of the present invention and color compositions even be used to contain printing-ink, coating, plastics painted of water-based vehicles, also can access the dispersion effect excellence, have tinting strength printed matter, film, painted thing.And then, also be effective for the purposes of the colo(u)rant dispersion of requirements such as magnetic coating, color filter, ink-jet height.
The vehicles that can be used in pigment dispersion of the present invention has non-aqueous vehicles and water-based vehicles.Non-aqueous vehicles can be enumerated limed rosin varnish, polyamide resin varnish, urethane resin varnish or vinyl chloride resin varnish, but is not limited to these examples.These vehicles can be used for the Air drying of gravure printing ink, zapon varnish, amino-alkyd resin or baked paint, acrylic varnish, aminoacrylic acid resin baked paint, polyurethanes cold coating etc.In addition, the water-based vehicles for example can be enumerated water-borne acrylic resin varnish, waterborne polyurethane resin varnish, but is not limited to these examples.Vehicles described here is by the resin solid component with the material that its dissolving or dispersive solvent constitute, and is meant the medium of dispersible pigment composition.With respect to 100 parts by weight resin, the ratio of resin and solvent is preferably solvent 100～10000 in the vehicles, more preferably 400～2000 weight parts.With respect to pigment dispersing agent 100 weight parts, vehicles is preferably 500～100000 weight parts, more preferably 1000～50000 weight parts.
Pigment dispersion of the present invention contains resin.Resin can use all resins that are used for common coating or printing ink.For example can enumerate soluble cotton as this resin, cellulose acetate, ethyl cellulose, urethane resin, polyamide resin, polyvinyl butyral resin, acrylic resin, vibrin, Synolac, calcium fat, appropriate youngster's oil rosin, wood rosin, rosin ester, rosin modified phenol, petroleum resin, linseed oil, tung oil, soybean oil, maleic acid resin, Vinylite, thermoprene, chlorinated rubber, ethene-vinyl acetate resin, gilsonite, reach horse natural gum, shellac, Resins, epoxy, vinylchlorid, silicone resin, melamine resin, urea resin, benzo guanamine resin etc., but be not limited to these examples.Wherein, for molecular weight the urethane resin of 5000～100000 the tackiness agent that is generally used for printing ink etc., pigment dispersing agent in the past almost be can't see effect, the colo(u)rant dispersion difficulty.But,, can obtain king-sized effect if use color compositions of the present invention.
The resin that is used for pigment dispersion of the present invention can use one or more of above-mentioned resin, also can use one or more resins and other resin dilution back uses of dispersive high density colo(u)rant dispersion body and function.
The urethane resin that generally is used for the tackiness agent of printing-ink etc., its main skeleton are the compositions that the reaction by polyol and polymeric polyisocyanate obtains.In addition, for the purpose of giving as the performance of tackiness agent, urethane resin usually uses compounds such as one or both or above glycols, two amines, alkamine, carries out polymer by the reaction that is called as transfer reaction and quantizes.Among the present invention, also can use two amines or alkamine to carry out transfer reaction, obtain the stronger urethane resin of alkalescence that each intramolecularly has a urea key at least.If use this urethane resin, the pigment dispersion of color compositions and this color compositions of use can obtain significant effect.
Pigment dispersion of the present invention contains organic solvent.Described organic solvent for example can be enumerated: aromatic hydrocarbon such as toluene; Petroleum-type hydrocarbons such as mineral turpentine; Halohydrocarbon such as chlorobenzene; Ketones such as acetone, methyl ethyl ketone, methyl iso-butyl ketone (MIBK), pimelinketone; Ester classes such as ethyl acetate, butylacetate, pentyl acetate, acetate 2-ethoxy ethyl ester; Alcohols such as methyl alcohol, ethanol, propyl alcohol, butanols; Cellosolve such as ethyl cellosolve, ethylene glycol butyl ether class, but be not limited to these examples.Especially be preferably ketone, alcohols, cellosolve class, organic solvent that ester class isopolarity is strong.Certainly organic solvent also can be the mixture of two or more solvent.
Color compositions of the present invention or pigment dispersion can be used for printing-ink or coating., for example can enumerate defoamer, levelling agent, anti, tensio-active agent, viscosity modifier, wax etc., but be not limited to these examples with vehicles or be used for the additive of coating as the printing-ink that uses in this case.
Embodiment
Below, by embodiment the present invention is described.In these embodiments, described part of expression weight part, described % represents weight %.
Production Example 1
In 300 part of 99% sulfuric acid, add 15 parts of Pigment reds 166,25 ℃ of reactions 3 hours.This reaction solution is injected in 3000 portions of frozen water, filters after the stirring, clean with 2% aqueous hydrochloric acid.After the filter cake that obtains made slurries with 700 parts of water, regulate pH to 9 with sodium hydroxide.Then, be heated to 60 ℃, add 58 part of 10% aluminum sulfate aqueous solution, after 1 hour, filter 60 ℃ of stirrings, washing, drying obtains 18 parts of pigment dispersing agents (a).Sulfonic average substituting group quantity is 1.8.
Production Example 2
Pigment red 166 is changed to pigment red 21 4, simultaneously, temperature of reaction is changed to 30 ℃ from 25 ℃, and 58 part of 10% aluminum sulfate aqueous solution changed to 29 part of 10% calcium chloride water, in addition similarly operate with Production Example 1, obtain 17 parts of pigment dispersing agents (b).Sulfonic average substituting group quantity is 1.5.
Production Example 3
Pigment red 166 is changed to Pigment red 144, simultaneously, temperature of reaction is changed to 20 ℃ from 25 ℃, and 58 part of 10% aluminum sulfate aqueous solution changed to 33 part of 10% ferrous sulfate aqueous solution, in addition similarly operate with Production Example 1, obtain 18 parts of pigment dispersing agents (c).Sulfonic average substituting group quantity is 1.2.
Production Example 4
Pigment red 166 is changed to Pigment red 221, simultaneously, temperature of reaction is changed to 20 ℃ from 25 ℃, and 58 part of 10% aluminum sulfate aqueous solution changed to 25 part of 10% strontium chloride aqueous solution, in addition similarly operate with Production Example 1, obtain 17 parts of pigment dispersing agents (d).Sulfonic average substituting group quantity is 1.0.
Production Example 5
58 part of 10% aluminum sulfate aqueous solution changed to 128 parts, in addition similarly operate, obtain 20 parts of pigment dispersing agents (e) with Production Example 1.Sulfonic average substituting group quantity is 4.0.
Embodiment 1～16, comparative example 1～4
As shown in table 1, any 10 parts of color compositions, the gravure printing ink that has added pigment dispersing agent (a)～(d) in each pigment mixed for 100 parts with 90 parts of stand linseed oil and 3mm granulated glass sphere.Gravure printing ink contains nitrocellulose resin 12%, ethyl acetate 33%, toluene 30%, Virahol 15%, methyl alcohol 10% with stand linseed oil.Is the mixture that obtains that the printing ink setting device was disperseed 60 minutes with a kind of wet type microparticulate pulverizer, makes gravure printing ink.In addition, as a comparative example, do not add pigment dispersing agent, just similarly disperse various pigment, make the gravure printing ink that does not contain pigment dispersing agent of the present invention.Measure the viscosity of the printing ink made from Brookfield viscometer (6rpm).In addition, the printing ink made from winding the line excellent doctor knife coater color development to film, is measured the gloss number (60 °) of the dry epithelium of this moment.This results are shown in the table 1.
Use the printing ink of the embodiment 1～16 of pigment dispersing agent of the present invention to demonstrate low viscosity and excellent flowability, and then coating film gloss is also fine.By contrast, do not contain then viscosity height of the comparative example 2 of pigment dispersing agent of the present invention and 4 printing ink, the printing ink of comparative example 1～4 then coating film gloss is poor.
Table 1
| The example sequence number | Pigment type | Dispersion agent | Dispersion agent addition (with respect to pigment) | Viscosity 6rpm (mPs) | Gloss 60G (%) |
| Comparative example 1 | C.I. Pigment red 185 | - | - | 1620 | 34 |
| Embodiment 1 | a | 5％ | 380 | 55 | |
| Embodiment 2 | b | 5％ | 420 | 53 | |
| Embodiment 3 | c | 5％ | 450 | 52 | |
| Embodiment 4 | d | 5％ | 450 | 52 | |
| Comparative example 2 | C.I. pigment red 146 | - | - | 4500 | 30 |
| Embodiment 5 | a | 5％ | 1350 | 52 | |
| Embodiment 6 | b | 5％ | 1480 | 51 | |
| Embodiment 7 | c | 5％ | 1500 | 50 | |
| Embodiment 8 | d | 5％ | 1650 | 50 | |
| Comparative example 3 | C.I. Pigment red 166 | - | - | 1400 | 28 |
| Embodiment 9 | a | 3％ | 380 | 50 | |
| Embodiment 10 | b | 3％ | 420 | 50 | |
| Embodiment 11 | c | 3％ | 480 | 48 | |
| Embodiment 12 | d | 3％ | 500 | 48 | |
| Comparative example 4 | C.I. Pigment red 221 | - | - | 3500 | 20 |
| Embodiment 13 | a | 7％ | 800 | 48 | |
| Embodiment 14 | b | 7％ | 950 | 45 | |
| Embodiment 15 | c | 7％ | 1100 | 43 | |
| Embodiment 16 | d | 7％ | 1270 | 43 |
Viscosity: use the Type B rotational viscosimeter to measure down at 25 ℃.
Gloss: 60 ° of angle gloss numbers
Embodiment 17～32, comparative example 5～10
As shown in table 2, any 20 parts of the color compositions, gravure printing ink that has added pigment dispersing agent (a)～(e) in each pigment mixed for 100 parts with 80 parts of stand linseed oil, 2 parts of resin type pigment dispersing agents (monosodium glutamate Off ア イ Application テ Network ノ Co., Ltd.'s system " ア ジ ス パ one PB821 ") and 3mm granulated glass sphere.Gravure printing ink contains urethane resin 15%, ethyl acetate 65% and Virahol 20% with stand linseed oil.Then, the mixture that obtains was disperseed 60 minutes with the printing ink setting device, make pigment dispersion.In addition, as a comparative example, similarly disperse various pigment separately, make the pigment dispersion that does not contain pigment dispersing agent of the present invention.Here, as above-mentioned urethane resin, use the urethane resin that obtains as follows, promptly, by polycondensation 3-methyl isophthalic acid, 5-pentanediol and hexanodioic acid obtain polyester polyol, with itself and isophorone diisocyanate condensation and obtain prepolymer, make its chainpropagation with isophorone diamine again and the urethane resin that contains the urea key of the weight-average molecular weight about 30000 that obtains.
Measure the viscosity of the pigment dispersion made from Brookfield viscometer (6rpm).In addition, in the pigment dispersion of making, add solvent (constituting) by 70% ethyl acetate and 30% Virahol, with examine No. 4, grace cup regulate the time that flows down be 14～16 seconds gravure printing ink with the excellent doctor knife coater color development of coiling to film, measure the gloss number (60 °) of the dry epithelium of this moment.And then the coated face of color development thing on nylon film and uncoated nylon film adhered to, after under 100 ℃ this test film being boiled 1 hour, investigate tone transport property (bleeding testing) to uncoated thin film.These the results are shown in the table 2.
The pigment dispersion that contains the embodiment 17～32 of pigment dispersing agent of the present invention demonstrates low viscosity and excellent flowability, and coating film gloss is also fine in addition.By contrast, do not contain then viscosity height of the comparative example 5～7,9 of pigment dispersing agent of the present invention and 10 pigment dispersion, do not contain the comparative example 5～7 of pigment dispersing agent of the present invention and the low in glossiness of 9 pigment dispersion.
In addition, in comparative example 8 and 10, contain the printing ink that has sulfonic pigment dispersing agent (e) more than 4 or 4 at an intramolecularly, tone has been moved to uncoated thin film from coated thin film.By contrast, used tone not migration mutually among the embodiment 17～32 of pigment dispersing agent of the present invention.
Table 2
| The example sequence number | Pigment type | Dispersion agent | Dispersion agent addition (with respect to pigment) | Viscosity 6rpm (mPs) | Gloss 60G (%) | Bleeding testing |
| Comparative example 5 | C.I. Pigment red 185 | - | - | 58000 | 30 | ○ |
| Embodiment 17 | a | 5％ | 2580 | 52 | ○ | |
| Embodiment 18 | b | 5％ | 3200 | 50 | ○ | |
| Embodiment 19 | c | 5％ | 3450 | 50 | ○ | |
| Embodiment 20 | d | 5％ | 4100 | 48 | ○ | |
| Comparative example 6 | C.I. pigment red 146 | - | - | 53000 | 32 | ○ |
| Embodiment 21 | a | 5％ | 1650 | 54 | ○ | |
| Embodiment 22 | b | 5％ | 1880 | 52 | ○ | |
| Embodiment 23 | c | 5％ | 2100 | 51 | ○ | |
| Embodiment 24 | d | 5％ | 2500 | 50 | ○ | |
| Comparative example 7 | C.I. Pigment red 166 | - | - | 5500 | 35 | ○ |
| Embodiment 25 | a | 3％ | 380 | 75 | ○ | |
| Embodiment 26 | b | 3％ | 440 | 73 | ○ | |
| Embodiment 27 | c | 3％ | 500 | 72 | ○ | |
| Embodiment 28 | d | 3％ | 580 | 70 | ○ | |
| Comparative example 8 | e | 3％ | 950 | 65 | × | |
| Comparative example 9 | C.I. Pigment red 221 | - | - | 95000 | 25 | ○ |
| Embodiment 29 | a | 7％ | 2400 | 72 | ○ | |
| Embodiment 30 | b | 7％ | 3000 | 70 | ○ | |
| Embodiment 31 | c | 7％ | 3500 | 70 | ○ | |
| Embodiment 32 | d | 7％ | 4400 | 69 | ○ | |
| Comparative example 10 | e | 7％ | 32500 | 55 | × |
Viscosity: use the Type B rotational viscosimeter to measure down at 25 ℃.
Gloss: 60 ° of angle gloss numbers
Bleeding testing: zero expression does not have painted, and * expression is painted.
In addition, contain the color compositions of above-mentioned pigment dispersing agent (a)～(e), promptly be used in the coating of resins such as containing alkyd amino, aminoacrylic acid, also can not cause aggegation, demonstrate good flowability and coating film gloss.
Claims (6)
1. by the pigment dispersing agent of following general formula (1) expression,
In the formula, R
1, R
2, R
3, R
4, R
5, R
6, R
7, R
8, R
9And R
10Independently of one another expression-H ,-Cl ,-CH
3,-CF
3,-NO
2,-COOCH (CH
3)
2,-COOCH
2CH
2C1; R
11, R
12, R
13And R
14Independently of one another expression-H ,-Cl ,-CH
3,-CN; M represents the monovalent of divalence or tervalent metal; N represents 1～3 integer.
2. color compositions is characterized in that, contains at least a pigment and the described pigment dispersing agent of claim 1 selected from the group of being made up of naphthols pigment and azo condensation pigment.
3. the described color compositions of claim 2 is characterized in that, also contains weight-average molecular weight and be 1000～100000 resin type pigment dispersing agent.
4. the described color compositions of claim 2 is dispersed in the pigment dispersion in non-aqueous or the water-based vehicles.
5. the described pigment dispersion of claim 4 is characterized in that, it is 5000～100000 resin that described non-aqueous vehicles contains weight-average molecular weight, and described resin is the urethane resin that has at least one urea key at an intramolecularly.
6. printing-ink is characterized in that, contains claim 4 or 5 described pigment dispersions.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200510098426 CN100560660C (en) | 2005-09-06 | 2005-09-06 | Pigment dispersing agent and with its color compositions, pigment dispersion and printing-ink |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200510098426 CN100560660C (en) | 2005-09-06 | 2005-09-06 | Pigment dispersing agent and with its color compositions, pigment dispersion and printing-ink |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1927953A true CN1927953A (en) | 2007-03-14 |
| CN100560660C CN100560660C (en) | 2009-11-18 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 200510098426 Expired - Fee Related CN100560660C (en) | 2005-09-06 | 2005-09-06 | Pigment dispersing agent and with its color compositions, pigment dispersion and printing-ink |
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| Country | Link |
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| CN (1) | CN100560660C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101205418B (en) * | 2007-11-29 | 2010-06-09 | 东华大学 | Polyether primary amine derivative disperser for paint, preparation and use thereof |
| CN103623739A (en) * | 2012-08-24 | 2014-03-12 | 第一工业制药株式会社 | Dispersant for non-aquous dispersion medium and dispersion |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104292968B (en) * | 2014-10-30 | 2016-04-06 | 泸州观宇玻璃制品有限公司 | A kind of glass wine bottle ink for screen printing |
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2005
- 2005-09-06 CN CN 200510098426 patent/CN100560660C/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101205418B (en) * | 2007-11-29 | 2010-06-09 | 东华大学 | Polyether primary amine derivative disperser for paint, preparation and use thereof |
| CN103623739A (en) * | 2012-08-24 | 2014-03-12 | 第一工业制药株式会社 | Dispersant for non-aquous dispersion medium and dispersion |
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| Publication number | Publication date |
|---|---|
| CN100560660C (en) | 2009-11-18 |
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