CN101220229B - Dye dispersion liquid - Google Patents
Dye dispersion liquid Download PDFInfo
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- CN101220229B CN101220229B CN2008100022556A CN200810002255A CN101220229B CN 101220229 B CN101220229 B CN 101220229B CN 2008100022556 A CN2008100022556 A CN 2008100022556A CN 200810002255 A CN200810002255 A CN 200810002255A CN 101220229 B CN101220229 B CN 101220229B
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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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
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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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
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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
- 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
- C09D17/00—Pigment pastes, e.g. for mixing in paints
- C09D17/003—Pigment pastes, e.g. for mixing in paints containing an organic pigment
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- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
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- Dispersion Chemistry (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
The invention relates to a pigment disoersion liquid which can form a coating film with a higher transparency and contrast, wherein the decentrality of the pigment and the solubleness of the decentralized resin are excellent and the coating capability is high. The pigment disoersion liquid contains pigment and organic solvents which are at least one organic solvent selected from (a) hydroxycarboxylate compound groups composed of hydroxycarboxylate of which the carbon atom number of the carboxylic acid part is 2-6, (b) acetoxy carboxylate compound groups composed of acetoxy carboxylate of which the carbon atom number of the carboxylic acid part is 2-6, and (c) alkoxy carboxylate compound groups composed of alkoxy carboxylate of which the carbon atom number of the carboxylic acid part is 2-6.
Description
Technical field
The present invention relates to a kind of dispersible pigment dispersion that in coating, printing-ink and other purposes, uses; More specifically relate to and in such as automobile, coated steel plate, building materials, jar, flat board, intaglio plate (グ ラ PVC ァ), flexographic plate (Off レ キ ソ), ink-jet printer, colour filter etc., to use; Excellent in safety during use; Pigment-dispersing, coating, transparency excellence, the coating back forms the dispersible pigment dispersion that high-contrast is filmed.
Background technology
Dispersible pigment dispersion requires to possess various performances, for example the polymolecularity of pigment, dispersing of pigments stability, disperse the good fluidity of high resolution, dispersion liquid with resin, in the security of the volatile solvent of the stability of flow of apparatus for coating injection part, use etc.In addition, behind the coating pigment dispersion liquid, require to have high-luster, high resolution, high-light-fastness, particularly colour filter, require to have high-contrast, high transmissivity etc.In order to satisfy this requirement, all kinds of SOLVENTS is used as and disperses to use solvent.As the desired performance of solvent, the characteristic that colo(u)rant dispersion is used, can enumerate that dispersing of pigments property for example is high, safe, the cheapness when disperseing high with dissolving resin property, excellent, use etc. in the stability of flow drying property excellent, that film of apparatus for coating injection part.
But the solvent that in fact can fully satisfy above-mentioned performance, characteristic seldom.Its reason can be enumerated and satisfy pigment-dispersing simultaneously and disperse the polarity of solvent with resin dissolves property to be restricted.In the past, the solvent as colo(u)rant dispersion is used used cellosolve class, propylene glycol monomethyl ether and their acetic ester (for example, with reference to patent documentation 1) such as glycol monomethyl methyl ether, ethylene glycol monomethyl ether all the time.But the drying property of these solvents is high, thereby dry at apparatus for coating injection parts such as gap coating (ス リ ッ ト コ one ト), ink-jet application, occur because of stop up or solids to separate out the seepage (liquid ダ レ), the coating that cause bad.In addition, the cellosolve class is the high solvent of toxicity, therefore the dangerous height on processing safety.
Patent documentation 1 spy opens flat 6-279702 communique
Summary of the invention
Therefore, the object of the present invention is to provide not only pigment-dispersing and disperse with dissolving resin property excellent and coating height, can form the transparency and the higher dispersible pigment dispersion of filming of contrast gradient.
The present inventor concentrates on studies, and the result finds: through using specific organic solvent as the solvent that constitutes dispersible pigment dispersion, can realize above-mentioned purpose, thereby accomplish the present invention.
Promptly; The present invention provides dispersible pigment dispersion; It is characterized in that; It contains pigment and organic solvent, and this organic solvent contains that to be selected from (a) be the hydroxycarboxylic acid ester cpds group that constitutes of 2～6 hydroxycarboxylic acid esters, (b) by the carbonatoms of carboxylic moiety is the acetoxyl group carbonate group that constitutes of 2～6 acetoxyl group carboxylicesters and (c) is at least a kind of organic solvent among the alkoxyl carboxylate compound group that constitutes of 2～6 alkoxyl carboxylate by the carbonatoms of carboxylic moiety by the carbonatoms of carboxylic moiety.
In the above-mentioned dispersible pigment dispersion, organic solvent also can contain from (a), and to be the hydroxycarboxylic acid ester cpds group that constitutes of 2～6 hydroxycarboxylic acid esters, (b) by the carbonatoms of carboxylic moiety be the acetoxyl group carbonate group that constitutes of 2～6 acetoxyl group carboxylicesters and (c) be to select the multiple organic solvent more than a kind respectively at least two group compound groups these three groups of compound groups of alkoxyl carboxylate compound group of constituting of 2～6 alkoxyl carboxylate by the carbonatoms of carboxylic moiety by the carbonatoms of carboxylic moiety.
In the above-mentioned dispersible pigment dispersion, organic solvent can further contain at least a kind of organic solvent that is selected among single propylene glycol monomethyl ether and the single methyl proxitol acetate.In addition, organic solvent can also further contain at least a kind of organic solvent that is selected among alkyl carboxylates class and the aliphatics ketone.Except that pigment and organic solvent, said dispersible pigment dispersion can also further contain resin and/or dispersing auxiliary.
The present invention can provide drying property, coating raising and the transparency and contrast gradient and the safe dispersible pigment dispersion that colo(u)rant dispersion is high with dissolving resin property, the stability of dispersible pigment dispersion improves and can regulate this dispersible pigment dispersion.
Embodiment
In the dispersible pigment dispersion of the present invention; As organic solvent, contain that to be selected from (a) be the hydroxycarboxylic acid ester cpds group that constitutes of 2～6 hydroxycarboxylic acid esters, (b) by the carbonatoms of carboxylic moiety is the acetoxyl group carbonate group that constitutes of 2～6 acetoxyl group carboxylicesters and (c) is at least a kind of organic solvent among the alkoxyl carboxylate compound group that constitutes of 2～6 alkoxyl carboxylate by the carbonatoms of carboxylic moiety by the carbonatoms of carboxylic moiety.
These organic solvents can be distinguished independent use, also can mix use with arbitrary proportion more than 2 kinds.In addition, also can also use with other organic solvents beyond above-mentioned.
Above-mentioned " carbonatoms of carboxylic moiety is 2～6 hydroxycarboxylic acid esters " refers in the ester of carboxylic acid of carbonatoms 2～6 at the compound that is connected with (preferred 1) hydroxyl more than 1 or 2 on the carbon atom of carboxylic moiety; " carbonatoms of carboxylic moiety is 2～6 acetoxyl group carboxylicesters " refers in the ester of carboxylic acid of carbonatoms 2～6 at the compound that is connected with (preferred 1) acetoxyl group more than 1 or 2 on the carbon atom of carboxylic moiety, and " carbonatoms of carboxylic moiety is 2～6 alkoxyl carboxylate " refers in the ester of carboxylic acid of carbonatoms 2～6 at the compound that is connected with (preferred 1) alkoxyl group more than 1 or 2 on the carbon atom of carboxylic moiety.As " carboxylic acid " in above-mentioned (a)～(c), aliphatic carboxylic acid or ester ring type carboxylic acid, wherein, aliphatic carboxylic acid (particularly aliphatics saturated carboxylic acid)." carboxylic acid " can be monocarboxylic acid, also can be polycarboxylic acids such as dicarboxylicacid, tricarboxylic acid.As " ester " in above-mentioned (a)～(c), preferred alkyl ester, the alkyl ester of carbonatomss 1～4 such as wherein preferred methyl esters, ethyl ester, propyl ester, butyl ester.The preferred all esterifications of the carboxyl of carboxylic acid.As " alkoxyl group " in above-mentioned (c), the alkoxyl group of preferred carbonatoms 1～6, wherein, the alkoxyl group of carbonatomss 1～4 such as preferred methoxyl group, oxyethyl group, propoxy-, butoxy.
As the carbonatoms of the carboxylic moiety in (a) is 2～6 hydroxycarboxylic acid esters, can enumerate for example glycolic acid esters such as hydroxy methyl acetate, hydroxyl ethyl acetate, oxyacetic acid propyl ester, oxyacetic acid butyl ester; Hydroxy propionates (2 hydroxy propanoic acid ester, 3-hydroxy propionate) such as hydroxy methyl propionate, hydroxy-propionic acid ethyl ester, hydroxy-propionic acid propyl ester, hydroxy-propionic acid butyl ester; Butyric esters (2-butyric ester, 3-butyric ester, 4 hydroxybutyric acid ester) such as beta-hydroxymethyl butyrate, 3-hydroxyethyl butyrate, hydroxybutyric acid propyl ester, hydroxybutyric acid butyl ester; Hydroxyl valerates (2-hydroxyl valerate, 3-hydroxyl valerate, 4-hydroxyl valerate, 5-hydroxyl valerate) such as hydroxypentanoic acid methyl esters, hydroxypentanoic acid ethyl ester, hydroxypentanoic acid propyl ester, hydroxypentanoic acid butyl ester; Tartronic acid diester such as tartronic acid dimethyl ester, tartronic acid diethyl ester, tartronic acid dipropyl, tartronic acid dibutylester, tartronic acid methyl ethyl ester, tartronic acid first propyl ester, tartronic acid first butyl ester; Hydroxy succinic acid diester such as hydroxy succinic acid dimethyl ester, diethyl hydroxysuccinate, hydroxy succinic acid dipropyl, hydroxy succinic acid dibutylester, hydroxy succinic acid methyl ethyl ester, hydroxy succinic acid first propyl ester, hydroxy succinic acid first butyl ester; Hydroxyl pentanedioic acid diester (2-hydroxyl pentanedioic acid diester, 3-hydroxyl pentanedioic acid diester) such as hydroxyl Methyl glutarate, hydroxyl ethyl glutarate, hydroxyl pentanedioic acid dipropyl, hydroxyl pentanedioic acid dibutylester, hydroxyl pentanedioic acid methyl ethyl ester, hydroxyl pentanedioic acid first propyl ester, hydroxyl pentanedioic acid first butyl ester; Hydroxyl di adipates (2-hydroxyl di adipate, 3-hydroxyl di adipate, 4-hydroxyl di adipate) such as hydroxyl dimethyl adipate, hydroxyl diethylene adipate, hydroxyl dipropyl adipate, hydroxyl Polycizer W 260, hydroxyl hexanodioic acid methyl ethyl ester, hydroxyl hexanodioic acid first propyl ester, hydroxyl hexanodioic acid first butyl ester; 2-hydroxyl-1,2,3-tricarballylic acid trimethyl, 2-hydroxyl-1,2,3-tricarballylic acid triethyl, 2-hydroxyl-1; 2,3-tricarballylic acid three propyl ester, 2-hydroxyl-1,2,3-tricarballylic acid tri-n-butyl, 2-hydroxyl-1; 2,3-tricarballylic acid dimethyl ethyl ester, 2-hydroxyl-1,2,3-tricarballylic acid dimethyl propyl ester, 2-hydroxyl-1; 2,3-tricarballylic acid dimethylbutyl ester, 2-hydroxyl-1,2,3-tricarballylic acid methylethyl propyl diester, 2-hydroxyl-1; 2,2-hydroxyls-1,2 such as 3-tricarballylic acid methylethyl butyl ester, 3-tricarballylic acid three esters etc.Wherein, 2 hydroxy propanoic acid alkyl ester such as preferred 2 hydroxy propanoic acid methyl esters.In addition, hydroxyl polycarboxylic acid's ester (especially hydroxyl polycarboxylic acid's alkyl ester) of 2-hydroxy succinic acid dialkyl such as preferred especially 2-hydroxy succinic acid dimethyl ester etc.
As the carbonatoms of the carboxylic moiety in (b) is 2～6 acetoxyl group carboxylicesters, can enumerate for example acetoxy acid esters such as acetoxy acid methyl esters, acetoxy acid ethyl ester, acetoxy acid propyl ester, acetoxy acid butyl ester; Acetoxyl group propionic esters (2-acetoxyl group propionic ester, 3-acetoxyl group propionic ester) such as acetoxyl group methyl propionate, acetoxyl group ethyl propionate, acetoxyl group propyl propionate, acetoxyl group butyl propionate; Acetoxyl group butyric esters (2-acetoxyl group butyric ester, 3-acetoxyl group butyric ester, 4-acetoxyl group butyric ester) such as acetoxyl group methyl-butyrate, acetoxyl group ethyl n-butyrate, acetoxyl group propyl butyrate, acetoxyl group butyl butyrate; Acetoxyl group valerates (2-acetoxyl group valerate, 3-acetoxyl group valerate, 4-acetoxyl group valerate, 5-acetoxyl group valerate) such as acetoxyl group methyl valerate, acetoxyl group Valeric acid ethylester, acetoxyl group propyl valerate, acetoxyl group butyl valerate; Acetoxyl group diester malonates such as acetoxyl group methyl-malonate, acetoxyl group ethyl malonate, acetoxyl group dipropyl malonate, acetoxyl group TERT-BUTYL MALONATE, acetoxyl group propanedioic acid methyl ethyl ester, acetoxyl group propanedioic acid first propyl ester, acetoxyl group propanedioic acid first butyl ester; Acetoxyl group succinic diester such as acetoxyl group Succinic acid dimethylester, acetoxyl group ethyl succinate, acetoxyl group Dipropyl Succinate, acetoxyl group dibutyl succinate, acetoxyl group succsinic acid methyl ethyl ester, acetoxyl group succsinic acid first propyl ester, acetoxyl group succsinic acid first butyl ester; Acetoxyl group pentanedioic acid diester (2-acetoxyl group pentanedioic acid diester, 3-acetoxyl group pentanedioic acid diester) such as acetoxyl group Methyl glutarate, acetoxyl group ethyl glutarate, acetoxyl group pentanedioic acid dipropyl, acetoxyl group pentanedioic acid dibutylester, acetoxyl group pentanedioic acid methyl ethyl ester, acetoxyl group pentanedioic acid first propyl ester, acetoxyl group pentanedioic acid first butyl ester; Acetoxyl group di adipates (2-acetoxyl group di adipate, 3-acetoxyl group di adipate, 4-acetoxyl group di adipate) such as acetoxyl group dimethyl adipate, acetoxyl group diethylene adipate, acetoxyl group dipropyl adipate, acetoxyl group Polycizer W 260, acetoxyl group hexanodioic acid methyl ethyl ester, acetoxyl group hexanodioic acid first propyl ester, acetoxyl group hexanodioic acid first butyl ester; 2-acetoxyl group-1,2,3-tricarballylic acid trimethyl, 2-acetoxyl group-1,2,3-tricarballylic acid triethyl, 2-acetoxyl group-1; 2,3-tricarballylic acid three propyl ester, 2-acetoxyl group-1,2,3-tricarballylic acid tri-n-butyl, 2-acetoxyl group-1; 2,3-tricarballylic acid dimethyl ethyl ester, 2-acetoxyl group-1,2,3-tricarballylic acid dimethyl propyl ester, 2-acetoxyl group-1; 2,3-tricarballylic acid dimethylbutyl ester, 2-acetoxyl group-1,2,3-tricarballylic acid methylethyl propyl diester, 2-acetoxyl group-1; 2,2-acetoxyl groups-1,2 such as 3-tricarballylic acid methylethyl butyl ester, 3-tricarballylic acid three esters etc.Wherein, 2-acetoxyl group dialkyl succinates such as 2-acetoxyl group alkyl propionates, 2-acetoxyl group Succinic acid dimethylester such as preferred especially 2-acetoxyl group methyl propionate.
As the carbonatoms of the carboxylic moiety in (c) is 2～6 alkoxyl carboxylate, can enumerate for example alkoxy acetic acid esters such as methoxy menthyl acetate, ethoxy acetate, propoxy-methyl acetate, butoxy acetic acid methyl esters, NSC 7300 ethyl ester, ethoxy ethyl acetate, propoxy-ETHYLE ACETATE, butoxy acetic acid ethyl ester, NSC 7300 propyl ester, ethoxyacetic acid propyl ester, propoxy-propyl acetate, butoxy acetic acid propyl ester, NSC 7300 butyl ester, ethoxyacetic acid butyl ester, propoxy-butylacetate, butoxy acetic acid butyl ester; Alkoxyl propionic esters such as methoxypropionic acid methyl esters, ethoxy-propionic acid methyl esters, propoxy-methyl propionate, butoxy methyl propionate, methoxy propyl acetoacetic ester, ethoxyl ethyl propionate, propoxy-ethyl propionate, butoxy ethyl propionate, methoxy propyl propyl propionate, ethoxy-c propyl propionate, propoxy-propyl propionate, butoxy propyl propionate, methoxy propyl acid butyl ester, ethoxy-c acid butyl ester, propoxy-butyl propionate, butoxy butyl propionate; Alkoxyl group butyric esters such as methoxyl group methyl-butyrate, oxyethyl group methyl-butyrate, propoxy-methyl-butyrate, butoxy methyl-butyrate, methoxyl group ethyl n-butyrate, oxyethyl group ethyl n-butyrate, propoxy-ethyl n-butyrate, butoxy ethyl n-butyrate, methoxyl group propyl butyrate, oxyethyl group propyl butyrate, propoxy-propyl butyrate, butoxy propyl butyrate, methoxyl group butyl butyrate, oxyethyl group butyl butyrate, propoxy-butyl butyrate, butoxy butyl butyrate; Alkoxyl group valerates such as methoxyl group methyl valerate, oxyethyl group methyl valerate, propoxy-methyl valerate, butoxy methyl valerate, methoxyl group Valeric acid ethylester, oxyethyl group Valeric acid ethylester, propoxy-Valeric acid ethylester, butoxy Valeric acid ethylester, methoxyl group propyl valerate, oxyethyl group propyl valerate, propoxy-propyl valerate, butoxy propyl valerate, methoxyl group butyl valerate, oxyethyl group butyl valerate, propoxy-butyl valerate, butoxy butyl valerate; The methoxyl group methyl-malonate; The oxyethyl group methyl-malonate; The propoxy-methyl-malonate; The butoxy methyl-malonate; The methoxyl group ethyl malonate; The oxyethyl group ethyl malonate; The propoxy-ethyl malonate; The butoxy ethyl malonate; The methoxy propyl dipropyl malona-te; The ethoxy-c dipropyl malona-te; The propoxy-dipropyl malonate; The butoxy dipropyl malonate; The methoxyl group TERT-BUTYL MALONATE; The oxyethyl group TERT-BUTYL MALONATE; The propoxy-TERT-BUTYL MALONATE; The butoxy TERT-BUTYL MALONATE; Methoxy propyl diacid methyl ethyl ester; Ethoxy-c diacid methyl ethyl ester; Propoxy-propanedioic acid methyl ethyl ester; Butoxy propanedioic acid methyl ethyl ester; Methoxy propyl diacid first propyl ester; Ethoxy-c diacid first propyl ester; The third oxygen propanedioic acid first propyl ester; Butoxy propanedioic acid first propyl ester; Methoxy propyl diacid first butyl ester; Ethoxy-c diacid first butyl ester; Propoxy-propanedioic acid first butyl ester; Alkoxyl group diester malonates such as butoxy propanedioic acid first butyl ester; The methoxyl group Succinic acid dimethylester; The oxyethyl group Succinic acid dimethylester; The propoxy-Succinic acid dimethylester; The butoxy Succinic acid dimethylester; The methoxyl group ethyl succinate; The oxyethyl group ethyl succinate; The propoxy-ethyl succinate; The butoxy ethyl succinate; The methoxyl group Dipropyl Succinate; The oxyethyl group Dipropyl Succinate; The propoxy-Dipropyl Succinate; The butoxy Dipropyl Succinate; The methoxyl group dibutyl succinate; The oxyethyl group dibutyl succinate; The propoxy-dibutyl succinate; The butoxy dibutyl succinate; Methoxyl group succsinic acid methyl ethyl ester; Oxyethyl group succsinic acid methyl ethyl ester; Propoxy-succsinic acid methyl ethyl ester; Butoxy succsinic acid methyl ethyl ester; Methoxyl group succsinic acid first propyl ester; Oxyethyl group succsinic acid first propyl ester; Propoxy-succsinic acid first propyl ester; Butoxy succsinic acid first propyl ester; Methoxyl group succsinic acid first butyl ester; Oxyethyl group succsinic acid first butyl ester; Propoxy-succsinic acid first butyl ester; Alkoxyl group succinic diester such as butoxy succsinic acid first butyl ester; The methoxyl group Methyl glutarate; The oxyethyl group Methyl glutarate; The propoxy-Methyl glutarate; The butoxy Methyl glutarate; The methoxyl group ethyl glutarate; The oxyethyl group ethyl glutarate; The propoxy-ethyl glutarate; The butoxy ethyl glutarate; Methoxyl group pentanedioic acid dipropyl; Oxyethyl group pentanedioic acid dipropyl; Propoxy-pentanedioic acid dipropyl; Butoxy pentanedioic acid dipropyl; Methoxyl group pentanedioic acid dibutylester; Oxyethyl group pentanedioic acid dibutylester; Propoxy-pentanedioic acid dibutylester; Butoxy pentanedioic acid dibutylester; Methoxyl group pentanedioic acid methyl ethyl ester; Oxyethyl group pentanedioic acid methyl ethyl ester; Propoxy-pentanedioic acid methyl ethyl ester; Butoxy pentanedioic acid methyl ethyl ester; Methoxyl group pentanedioic acid first propyl ester; Oxyethyl group pentanedioic acid first propyl ester; Propoxy-pentanedioic acid first propyl ester; Butoxy pentanedioic acid first propyl ester; Methoxyl group pentanedioic acid first butyl ester; Oxyethyl group pentanedioic acid first butyl ester; Propoxy-pentanedioic acid first butyl ester; Alkoxyl group pentanedioic acid diester (2-alkoxyl group pentanedioic acid diester such as butoxy pentanedioic acid first butyl ester; 3-alkoxyl group pentanedioic acid diester); The methoxyl group dimethyl adipate; The oxyethyl group dimethyl adipate; The propoxy-dimethyl adipate; The butoxy dimethyl adipate; The methoxyl group diethylene adipate; The oxyethyl group diethylene adipate; The propoxy-diethylene adipate; The butoxy diethylene adipate; The methoxyl group dipropyl adipate; The oxyethyl group dipropyl adipate; The propoxy-dipropyl adipate; The butoxy dipropyl adipate; The methoxyl group Polycizer W 260; The oxyethyl group Polycizer W 260; The propoxy-Polycizer W 260; The butoxy Polycizer W 260; Methoxyl group hexanodioic acid methyl ethyl ester; Oxyethyl group hexanodioic acid methyl ethyl ester; Propoxy-hexanodioic acid methyl ethyl ester; Butoxy hexanodioic acid methyl ethyl ester; Methoxyl group hexanodioic acid first propyl ester; Oxyethyl group hexanodioic acid first propyl ester; Propoxy-hexanodioic acid first propyl ester; Butoxy hexanodioic acid first propyl ester; Methoxyl group hexanodioic acid first butyl ester; Oxyethyl group hexanodioic acid first butyl ester; Propoxy-hexanodioic acid first butyl ester; Alkoxyl group di adipate (2-alkoxyl group di adipates such as butoxy hexanodioic acid first butyl ester; 3-alkoxyl group di adipate; 4-alkoxyl group di adipate); 2-methoxyl group-1,2,3-tricarballylic acid trimethyl, 2-methoxyl group-1,2,3-tricarballylic acid triethyl, 2-methoxyl group-1,2; 3-tricarballylic acid three propyl ester, 2-methoxyl group-1,2,3-tricarballylic acid tri-n-butyl, 2-methoxyl group-1,2,3-tricarballylic acid dimethyl ethyl ester, 2-methoxyl group-1,2; 3-tricarballylic acid dimethyl ethyl ester, 2-methoxyl group-1,2,3-tricarballylic acid dimethyl propyl ester, 2-methoxyl group-1,2,3-tricarballylic acid dimethylbutyl ester, 2-methoxyl group-1,2; 3-tricarballylic acid methylethyl propyl diester, 2-methoxyl group-1,2,3-tricarballylic acid methylethyl butyl ester, 2-oxyethyl group-1,2,3-tricarballylic acid trimethyl, 2-oxyethyl group-1,2; 3-tricarballylic acid triethyl, 2-oxyethyl group-1,2,3-tricarballylic acid three propyl ester, 2-oxyethyl group-1,2,3-tricarballylic acid tri-n-butyl, 2-oxyethyl group-1,2; 3-tricarballylic acid dimethyl ethyl ester, 2-oxyethyl group-1,2,3-tricarballylic acid dimethyl propyl ester, 2-oxyethyl group-1,2,3-tricarballylic acid dimethylbutyl ester, 2-oxyethyl group-1; 2,3-tricarballylic acid methylethyl propyl diester, 2-oxyethyl group-1,2,3-tricarballylic acid methylethyl butyl ester, 2-propoxy--1,2; 3-tricarballylic acid trimethyl, 2-propoxy--1,2,3-tricarballylic acid triethyl, 2-propoxy--1,2,3-tricarballylic acid three propyl ester, 2-propoxy--1; 2,3-tricarballylic acid tri-n-butyl, 2-propoxy--1,2,3-tricarballylic acid dimethyl ethyl ester, 2-propoxy--1,2; 3-tricarballylic acid dimethyl propyl ester, 2-propoxy--1,2,3-tricarballylic acid dimethylbutyl ester, 2-propoxy--1,2,3-tricarballylic acid methylethyl propyl diester, 2-propoxy--1; 2,3-tricarballylic acid methylethyl butyl ester, 2-butoxy-1,2,3-tricarballylic acid trimethyl, 2-butoxy-1,2; 3-tricarballylic acid triethyl, 2-butoxy-1,2,3-tricarballylic acid three propyl ester, 2-butoxy-1,2,3-tricarballylic acid tri-n-butyl, 2-butoxy-1; 2,3-tricarballylic acid dimethyl ethyl ester, 2-butoxy-1,2,3-tricarballylic acid dimethyl propyl ester, 2-butoxy-1,2; 3-tricarballylic acid dimethylbutyl ester, 2-butoxy-1,2,3-tricarballylic acid methylethyl propyl diester, 2-butoxy-1,2,3-tricarballylic acid methylethyl butyl ester etc.Wherein, 2-alkoxyl group dialkyl succinates such as 2-alkoxypropan acid alkyl ester, 2-methoxyl group Succinic acid dimethylester such as preferred especially 2-methoxypropionic acid methyl esters.
Above-mentioned organic solvent can use separately, but considers dispersing of pigments property and dissolving resin property etc., also can make up use more than 2 kinds.When combination is used more than 2 kinds; Preferably from aforementioned (a) hydroxycarboxylic acid ester cpds group, (b) acetoxyl group carbonate group and (c) select the mixed system of the multiple organic solvent more than a kind at least in the 2 group compound groups these 3 groups of compound groups of alkoxyl carboxylate compound group respectively; The mixed system of the organic solvent that contains in organic solvent that wherein, contains in the preferred above-mentioned alkoxyl carboxylate compound group and the acetoxyl group carbonate group.
As stated, when 2 kinds of organic solvent combinations were used, both ratios were suitably selected according to solvent types and purpose.For example; When the organic solvent combination that contains in organic solvent that contains in the above-mentioned alkoxyl carboxylate compound group and the acetoxyl group carbonate group is used; Both ratios for the former/latter's (weight ratio)=1/99～99/1; Preferred 5/95～95/5, further preferred about 10/90～90/10.The organic solvent combination that contains in organic solvent that contains in the hydroxycarboxylic acid ester cpds group and the alkoxyl carboxylate compound group is used; Or when the combination of the organic solvent that contains in organic solvent that contains in the hydroxycarboxylic acid ester cpds group and the acetoxyl group carbonate group used, preferably adopt ratio same as described above.
Among the present invention, in the scope that does not hinder effect of the present invention, can be also with other organic solvents beyond the above-mentioned organic solvent.As these other organic solvent, can enumerate for example single propylene glycol monomethyl ether, single methyl proxitol acetate, alkyl carboxylates class, aliphatics ketone.
For example comprise the alkyl ester of the aliphatic carboxylic acid of carbonatoms such as alkyl acetate, alkyl propionates about 1～4 (C for example in the above-mentioned alkyl carboxylates class
1-6Alkyl ester etc.) etc.
More specifically, as alkyl acetate, can enumerate acetate C such as propyl acetate, n-butyl acetate, n-amyl acetate
1-6Alkyl esters etc. as alkyl propionates, can be enumerated propionic acid C such as methyl propionate, ethyl propionate, propyl propionate, butyl propionate
1-6Alkyl ester etc.
As aliphatic ketone, can enumerate the aliphatics ketone (aliphatics single ketones class etc.) of carbonatomss such as 2-butanone, 2 pentanone, methyl-n-butyl ketone, 2-heptanone about 3～10 etc.
In the present invention; Be selected from the dispersible pigment dispersion above-mentioned (a) and (b) and (c) in the total amount of organic solvent, with respect to the total amount of the organic solvent in the dispersible pigment dispersion, preferred 20 weight %; Further more than the preferred 40 weight %, more preferably more than the 60 weight % (particularly more than the 80 weight %).Organic solvent in the dispersible pigment dispersion of the present invention, also can be in fact only by be selected from above-mentioned (a) and (b) and (c) in organic solvent constitute.The total amount of the organic solvent in the dispersible pigment dispersion, whole with respect to dispersible pigment dispersion, be generally 10～99 weight %, about preferred 50～95 weight %.
In the present invention, pigment can separately or make up more than 2 kinds and use.As said pigment, can be from suitably select and use the known various pigment (mineral dye, pigment dyestuff) in the past.No matter consider that dispersible pigment dispersion is advisable with high-transmission rate, be mineral dye or pigment dyestuff, all preferred thin as far as possible pigment of pigment; When considering operability; Preferred median size is below 0.1 μ m, further preferably at 0.01～0.1 μ m, most preferably in the scope of 0.01～0.05 μ m.
As pigment dyestuff, Colour Index (C.I. for example; The Society of Dyers and Colourists company distribution) compound that belongs to pigment (Pigment) type in specifically can be enumerated the pigment dyestuff that has following Colour Index (C.I.) number.But the invention is not restricted to these.
C.I. Pigment Yellow 73 1; C.I. Pigment Yellow 73 3; The C.I pigment Yellow 12; C.I. pigment yellow 13; The C.I pigment Yellow 14; C.I. Pigment Yellow 73 15; C.I. Pigment Yellow 73 16; C.I. pigment yellow 17; C.I Pigment Yellow 73 20; C.I Pigment Yellow 73 24; C.I. Pigment Yellow 73 31; C.I Pigment Yellow 73 55; C.I. Pigment Yellow 73 60; C.I. Pigment Yellow 73 61; C.I. Pigment Yellow 73 65; C.I. Pigment Yellow 73 71; C.I. Pigment Yellow 73 73; C.I. Pigment Yellow 73 74; C.I. pigment yellow 81; C.I. pigment yellow 83; C.I Pigment Yellow 73 93; C.I. Pigment Yellow 73 95; C.I. Pigment Yellow 73 97; C.I. Pigment Yellow 73 98; C.I. Pigment Yellow 73 100; C.I. Pigment Yellow 73 101; C.I. Pigment Yellow 73 104; C.I. Pigment Yellow 73 106; C.I. Pigment Yellow 73 108; C.I. Pigment Yellow 73 109; C.I Pigment Yellow 73 110; C.I. Pigment Yellow 73 113; C.I. Pigment Yellow 73 114; C.I Pigment Yellow 73 116; C.I. Pigment Yellow 73 117; C.I Pigment Yellow 73 119; C.I pigment Yellow 12 0; C.I. pigment Yellow 12 6; C.I. pigment Yellow 12 7; C.I. pigment Yellow 12 8; C.I pigment Yellow 12 9; C.I. pigment yellow 13 8; C.I pigment yellow 13 9; C.I. Pigment Yellow 73 150; C.I Pigment Yellow 73 151; C.I. Pigment Yellow 73 152; C.I. Pigment Yellow 73 153; C.I. pigment yellow 154; C.I. Pigment Yellow 73 155; C.I. Pigment Yellow 73 156; C.I. Pigment Yellow 73 166; C.I Pigment Yellow 73 168; C.I pigment yellow 17 5; C.I. pigment orange 1, C.I. pigment orange 5, C.I pigment Orange 13, C.I pigment orange 14, C.I pigment orange 16, C.I pigment orange 17, C.I pigment orange 24, C.I pigment orange 34, C.I. pigment orange 36, C.I. pigment orange 38, C.I pigment orange 40, C.I pigment orange 43, C.I. pigment orange 46, C.I pigment orange 49, C.I pigment orange 51, C.I pigment orange 61, C.I. pigment orange 63, C.I pigment orange 64, C.I. pigment orange 71, C.I. pigment orange 73; C.I pigment violet 1, C.I. pigment violet 19, C.I. pigment Violet 23, C.I. pigment violet 29, C.I. pigment violet 32, C.I. pigment violet 36, C.I. pigment violet 38; C.I. Pigment red 1; C.I. Pigment red 2; C.I. pigment red 3; C.I. pigment red 4; C.I. Pigment red 5; C.I. Pigment red 6; C.I. Pigment red 7; C.I. pigment Red 8; C.I. Pigment Red 9; C.I. Pigment red 10; C.I. Pigment red 11; C.I. Pigment red 12; C.I. Pigment red 14; C.I Pigment red 15; C.I. Pigment red 16; C.I. Pigment red 17; C.I. Pigment red 18; C.I. Pigment red 19; The C.I pigment red 21; C.I. Pigment red 22; C.I. Pigment red 23; C.I. pigment red 30; C.I. pigment red 31; C.I. pigment red 32; C.I. pigment red 37; C.I. pigment red 38; C.I. pigment red 40; C.I. pigment red 41; C.I pigment red 42; C.I. pigment red 4 8:1; C.I pigment red 4 8:2; C.I pigment red 4 8:3; C.I pigment red 4 8:4; C.I. pigment red 4 9:1; C.I pigment red 4 9:2; C.I. Pigment red 50:1; C.I Pigment red 52:1; C.I. Pigment red 53:1; C.I. Pigment red 57; C.I Pigment red 57:1; C.I Pigment red 57:2; C.I. Pigment red 58:2; C.I. Pigment red 58:4; C.I. Pigment red 60:1; C.I Pigment red 63:1; C.I. Pigment red 63:2; C.I. Pigment red 64:1; C.I. pigment red 81: 1; C.I pigment Red 83; C.I. pigment Red 88; C.I. Pigment Red 9 0:1; C.I. Pigment Red 97; C.I Pigment red 101; C.I Pigment red 102; C.I. Pigment red 104; C.I. Pigment red 105; C.I. Pigment red 106; C.I. Pigment red 108; The C.I Pigment Red 112; C.I. Pigment red 113; C.I. Pigment red 114; C.I. pigment red 122; C.I. pigment red 123; C.I. Pigment red 144; C.I. pigment red 146; C.I. pigment red 149; C.I Pigment red 150; C.I. Pigment red 151; C.I. Pigment red 166; C.I Pigment red 168; C.I Pigment red 170; C.I Pigment red 171; C.I Pigment red 172; C.I. Pigment red 174; C.I. Pigment red 175; C.I. Pigment red 176; C.I. Pigment red 177; C.I. Pigment red 178; C.I. Pigment red 179; C.I. Pigment red 180; C.I Pigment red 185; C.I Pigment red 187; C.I. Pigment red 188; C.I. Pigment red 190; C.I. Pigment red 193; C.I Pigment red 194; C.I Pigment red 202; C.I. Pigment red 206; C.I. Pigment Red 207; C.I Pigment red 208; C.I. Pigment red 209; C.I. pigment red 21 5; C.I. pigment red 21 6; C.I. Pigment red 220; C.I. Pigment red 224; C.I. Pigment red 226; C.I. Pigment red 242; C.I. Pigment red 243; C.I. Pigment red 245; C.I Pigment red 254; C.I. Pigment red 255; C.I. Pigment red 264; C.I. Pigment red 265; C.I. pigment Blue 15; C.I. pigment Blue 15: 3; C.I. pigment Blue 15: 4; C.I. pigment Blue 15: 6; The C.I pigment blue 60; C.I. pigment Green 7, C.I pigment green 36; C.I. pigment brown 23, C.I. pigment brown 25; C.I Pigment black 1, C.I. Pigment black 7.
In addition; As the object lesson of above-mentioned mineral dye or filler pigment, can enumerate titanium oxide, permanent white, lime carbonate, zinc white, lead sulfate, yellow lead, zinc yellow, iron oxide red (RED IRON OXIDE (III)), cadmium red, ultramarine, Prussian blue, chromoxide green, cobalt green, amber (ァ Application バ one), titanium black, synthesize iron oxide black, carbon black etc.
The total amount of the pigment in the dispersible pigment dispersion can suitably selected, but is generally about 1～80 weight %, preferred 1～50 weight % according to purposes.
When in dispersible pigment dispersion of the present invention, carrying out dispersing of pigments, can use the resin more than a kind or 2 kinds.Operable resin during as dispersion; Do not have particular restriction, can enumerate alkyd based resin, acrylics, trimeric cyanamide resinoid, polyurethanes resin, redix, silicon resinoid, polyester resin, polyamic acid resinoid, polyimide based resin, styrene maleic acid resinoid, styrene-maleic anhydride resinoid etc.Can also be suitable for various acrylic monomers, acrylic ester monomer.Preferred especially resin, monomer can be enumerated polyurethanes resin, acrylics, acrylic monomer, polyamic acid resinoid, polyimide based resin, styrene maleic acid resinoid, styrene-maleic anhydride resinoid.
The above-mentioned resin in the dispersible pigment dispersion and the total of monomeric amount for example are 1～80 weight %, about preferred 1～50 weight %.
Dispersible pigment dispersion of the present invention can be through preparing colo(u)rant dispersion with known dispersing method.As operable dispersion machine, for example roller mill, ball mill, ball mill, vertical ball mill, dispersator etc.In order to disperse effectively, with dispersion machines such as roller mills, disperse (promptly admittedly type mixing) with the ratio that nonvolatile component content is high, as required it is adjusted, nonvolatile component content appropriateness is reduced, then effect is better if disperse with ball mill etc.
In addition, also can be as required, the known in the past various additives such as (also comprising tensio-active agent) of proper fit dispersing auxiliary in dispersible pigment dispersion.Operable dispersing auxiliary does not receive particular restriction during dispersion; For example, can use the resin type dispersion agent (polymer pigment dispersant) (commercially available article have Disperbyk 130, Disperbyk 161, Disperbyk162, Disperbyk 163, Disperbyk 170, ェ Off カ 46, ェ Off カ 47 etc.) of amides, amino formate compounds, lactam analog compound, barbituric acid compounds, polyamide-based compound, polyurethanes compound and so on.In addition; Also can make up and use acrylic acid or the like, the such resin type dispersion agent (polymer pigment dispersant) of polyethylene kind; Silicon class or the such flow agent of non-silicon class, silicane, the such coupler of aluminium class, anionic, no ionic, cationic surfactant etc.
The amount of the above-mentioned dispersing auxiliary in the dispersible pigment dispersion for example is 1～80 weight %, about preferred 1～30 weight %.
Dispersible pigment dispersion of the present invention is applicable to coating, printing-ink, particularly, is applicable to for example middle coating that uses such as automobile, coated steel plate, building materials, jar, flat board, intaglio plate, flexographic plate, ink-jet printer, colour filter and printing-ink etc.
Embodiment
Below, specify the present invention through embodiment, but the invention is not restricted to this.
Embodiment 1
C.I. Pigment red 177 (Ciba-Geigy (チ バ ガ ィ キ one) corporate system, trade(brand)name " Cromophtal Red A3B (Network ロ モ Off タ one Le レ ッ De A3B) ") 15g, 2-acetoxyl group Succinic acid dimethylester 38g, polymer pigment dispersant (BYK-ChemieJapan (strain) (PVC ッ Network ケ ミ one ジ ャ パ Application) system, trade(brand)name " Disperbyk-161 ") 4g were disperseed 2 hours with homogenizer with granulated glass sphere 90g.Add vinyl resin (combine and grind chemistry (strain) system, trade(brand)name " ChemtreeL-20 (ケ ミ ト リ one L-20) ") 5g therein and be dissolved in the material among the 2-acetoxyl group Succinic acid dimethylester 38g, stir after 30 minutes, remove granulated glass sphere, the preparation dispersible pigment dispersion.
Embodiment 2
As pigment; With equivalent C.I. pigment Blue 15: 4 (BASF AG's system, trade(brand)name " Heliogen BlueD7100 ") replaced C .I. Pigment red 177 (Ciba-Geigy corporate system, trade(brand)name " Cromophtal RedA3B "); All likewise disperse the preparation dispersible pigment dispersion in addition with embodiment 1.
Embodiment 3
As pigment; With equivalent C.I. Pigment green 16 (BASF AG's system, trade(brand)name " Heliogen GreenD9360 ") replaced C .I. Pigment red 177 (Ciba-Geigy corporate system, trade(brand)name " Cromophtal RedA3B "); All likewise disperse the preparation dispersible pigment dispersion in addition with embodiment 1.
Embodiment 4
C.I. Pigment green 16 (BASF AG's system, trade(brand)name " Heliogen Green D9360 ") 15g, 2-methoxyl group Succinic acid dimethylester 38g, polymer pigment dispersant (BYK-ChemieJapan (strain) system, trade(brand)name " Disperbyk-161 ") 4g were disperseed 2 hours with homogenizer with granulated glass sphere 90g.Add vinyl resin (combine and grind chemistry (strain) system, trade(brand)name " Chemtree L-20 ") 5g therein and be dissolved in the material among the 2-methoxyl group Succinic acid dimethylester 38g, stir after 30 minutes, remove granulated glass sphere, the preparation dispersible pigment dispersion.
Embodiment 5
C.I. Pigment red 177 (Ciba-Geigy corporate system, trade(brand)name " Cromophtal RedA3B ") 15g, 2-hydroxy succinic acid dimethyl ester 38g, polymer pigment dispersant (BYK-ChemieJapan (strain) system, trade(brand)name " Disperbyk-161 ") 4g were disperseed 2 hours with homogenizer with granulated glass sphere 90g.Add vinyl resin (combine and grind chemistry (strain) system, trade(brand)name " Chemtree L-20 ") 5g therein and be dissolved in the material among the 2-hydroxy succinic acid dimethyl ester 38g, stir after 30 minutes, remove granulated glass sphere, the preparation dispersible pigment dispersion.
Embodiment 6
As pigment; With equivalent C.I. Pigment green 16 (BASF AG's system, trade(brand)name " Heliogen GreenD9360 ") replaced C .I Pigment red 177 (Ciba-Geigy corporate system, trade(brand)name " Cromophtal RedA3B "); All likewise disperse the preparation dispersible pigment dispersion in addition with embodiment 5.
Embodiment 7
C.I Pigment green 16 (BASF AG's system, trade(brand)name " Heliogen Green D9360 ") 15g, 2-acetoxyl group methyl propionate 38g, polymer pigment dispersant (BYK-ChemieJapan (strain) system, trade(brand)name " Disperbyk-161 ") 4g were disperseed 2 hours with homogenizer with granulated glass sphere 90g.Add vinyl resin (combine and grind chemistry (strain) system, trade(brand)name " Chemtree L-20 ") 5g therein and be dissolved in the material among the 2-acetoxyl group methyl propionate 38g, stir after 30 minutes, remove granulated glass sphere, the preparation dispersible pigment dispersion.
Embodiment 8
With the C.I. pigment Blue 15: 4 (BASF AG's system, trade(brand)name " Heliogen Blue D7100 ") 15g, 2 hydroxy propanoic acid methyl esters 38g, polymer pigment dispersant (BYK-Chemie (strain) system, trade(brand)name " Disperbyk-161 ") 4g disperseed 2 hours with homogenizer with granulated glass sphere 90g.Add vinyl resin (combine and grind chemistry (strain) system, trade(brand)name " Chemtree L-20 ") 5g therein and be dissolved in the material among the 2 hydroxy propanoic acid methyl esters 38g, stir after 30 minutes, remove granulated glass sphere, the preparation dispersible pigment dispersion.
Embodiment 9
C.I. Pigment red 177 (Ciba-Geigy corporate system, trade(brand)name " Cromophtal RedA3B ") 15g, 2-methoxypropionic acid methyl esters 38g, polymer pigment dispersant (BYK-ChemieJapan (strain) system, trade(brand)name " Disperbyk-161 ") 4g were disperseed 2 hours with homogenizer with granulated glass sphere 90g.Add vinyl resin (combine and grind chemistry (strain) system, trade(brand)name " Chemtree L-20 ") 5g therein and be dissolved in the material among the 2-methoxypropionic acid methyl esters 38g, stir after 30 minutes, remove granulated glass sphere, the preparation dispersible pigment dispersion.
Embodiment 10
C.I. Pigment red 177 (Ciba-Geigy corporate system, trade(brand)name " Cromophtal RedA3B ") 15g, 2-acetoxyl group Succinic acid dimethylester 38g, polymer pigment dispersant (BYK-ChemieJapan (strain) system, trade(brand)name " Disperbyk-161 ") 4g were disperseed 2 hours with homogenizer with granulated glass sphere 90g.Add vinyl resin (combine and grind chemistry (strain) system, trade(brand)name " Chemtree L-20 ") 5g therein and be dissolved in the material among the methyl proxitol acetate 38g, stir after 30 minutes, remove granulated glass sphere, the preparation dispersible pigment dispersion.
Embodiment 11
With the C.I. pigment Blue 15: 4 (BASF AG's system, trade(brand)name " Heliogen Blue D7100 ") 15g, 2-acetoxyl group methyl propionate 38g, polymer pigment dispersant (BYK-ChemieJapan (strain) system, trade(brand)name " Disperbyk-161 ") 4g disperseed 2 hours with homogenizer with granulated glass sphere 90g.Add vinyl resin (combine and grind chemistry (strain) system, trade(brand)name " Chemtree L-20 ") 5g therein and be dissolved in the material among the ethylene glycol monoethyl ether acetate 38g, stir after 30 minutes, remove granulated glass sphere, the preparation dispersible pigment dispersion.
Embodiment 12
C.I. Pigment green 16 (BASF AG's system, trade(brand)name " Heliogen Green D9360 ") 15g, 2-hydroxy succinic acid dimethyl ester 38g, polymer pigment dispersant (BYK-ChemieJapan (strain) system, trade(brand)name " Disperbyk-161 ") 4g were disperseed 2 hours with homogenizer with granulated glass sphere 90g.Add vinyl resin (combine and grind chemistry (strain) system, trade(brand)name " Chemtree L-20 ") 5g therein and be dissolved in the material among the propylene glycol monomethyl ether 38g, stir after 30 minutes, remove granulated glass sphere, the preparation dispersible pigment dispersion.
Comparative example 1
C.I. Pigment red 177 (Ciba-Geigy corporate system, trade(brand)name " Cromophtal RedA3B ") 15g, methyl proxitol acetate 38g, polymer pigment dispersant (BYK-ChemieJapan (strain) system, trade(brand)name " Disperbyk-161 ") 4g were disperseed 2 hours with homogenizer with granulated glass sphere 90g.Add vinyl resin (combine and grind chemistry (strain) system, trade(brand)name " Chemtree L-20 ") 5g therein and be dissolved in the material among the methyl proxitol acetate 38g, stir after 30 minutes, remove granulated glass sphere, the preparation dispersible pigment dispersion.
Comparative example 2
As pigment; With equivalent C.I. pigment Blue 15: 4 (BASF AG's system, trade(brand)name " Heliogen BlueD7100 ") replaced C .I. Pigment red 177 (Ciba-Geigy corporate system, trade(brand)name " Cromophtal RedA3B "); All likewise disperse the preparation dispersible pigment dispersion in addition with comparative example 1.
Comparative example 3
As pigment; With equivalent C.I. Pigment green 16 (BASF AG's system, trade(brand)name " Heliogen GreenD9360 ") replaced C .I. Pigment red 177 (Ciba-Geigy corporate system, trade(brand)name " Cromophtal RedA3B "); All likewise disperse the preparation dispersible pigment dispersion in addition with comparative example 1.
Comparative example 4
C.I. Pigment red 177 (Ciba-Geigy corporate system, trade(brand)name " Cromophtal RedA3B ") 15g, ethylene glycol monoethyl ether acetate 38g, polymer pigment dispersant (BYK-ChemieJapan (strain) system, trade(brand)name " Disperbyk-161 ") 4g were disperseed 2 hours with homogenizer with granulated glass sphere 90g.Add vinyl resin (combine and grind chemistry (strain) system, trade(brand)name " Chemtree L-20 ") 5g therein and be dissolved in the material among the ethylene glycol monoethyl ether acetate 38g, stir after 30 minutes, remove granulated glass sphere, the preparation dispersible pigment dispersion.
Comparative example 5
As pigment; With equivalent C.I pigment Blue 15: 4 (BASF AG's system, trade(brand)name " Heliogen BlueD7100 ") replaced C .I. Pigment red 177 (Ciba-Geigy corporate system, trade(brand)name " Cromophtal RedA3B "); All likewise disperse the preparation dispersible pigment dispersion in addition with comparative example 4.
Comparative example 6
As pigment; With equivalent C.I Pigment green 16 (BASF AG's system, trade(brand)name " Heliogen GreenD9360 ") replaced C .I Pigment red 177 (Ciba-Geigy corporate system, trade(brand)name " Cromophtal RedA3B "); All likewise disperse the preparation dispersible pigment dispersion in addition with comparative example 4.
Test Example 1
Initial stage viscosity and 40 ℃ of measuring the dispersible pigment dispersion of preparation in embodiment 1～12 and the comparative example 1～6 preserve down after 2 weeks through the time viscosity, shown in table 1～3.Table 1, table 2, table 3 are used C.I. Pigment red 177 (Ciba-Geigy corporate system, trade(brand)name " Cromophtal Red A3B "), C.I. pigment Blue 15 respectively: 4 (BASF AG's system, trade(brand)names " Heliogen Blue D7100 "), C.I. Pigment green 16 (BASF AG's system, trade(brand)name " Heliogen Green D9360 ") are as pigment.Poor when the ageing stability of dispersible pigment dispersion, when aggegation etc. disperses state deteriorating again, viscosity significantly rises.The viscosity of the dispersible pigment dispersion of embodiment 1～12 after 2 weeks changes below 5cPs, has the basicly stable property as dispersible pigment dispersion equally with comparative example 1～6.
Table 1
| Dispersed | Initial stage viscosity (cPs) | Through the time viscosity (cPs) | Viscosity rising (cPs) | |
| Embodiment 1 | Well | 12.25 | 12.75 | 0.50 |
| Embodiment 5 | Well | 13.14 | 14.04 | 0.90 |
| Embodiment 9 | Well | 12.35 | 13.15 | 0.80 |
| Embodiment 10 | Well | 10.90 | 11.50 | 0.60 |
| Comparative example 1 | Well | 13.95 | 15.21 | 1.26 |
| Comparative example 4 | Well | 12.55 | 12.95 | 0.40 |
Table 2
| Dispersed | Initial stage viscosity (cPs) | Through the time viscosity (cPs) | Viscosity rising (cPs) | |
| Embodiment 2 | Well | 7.30 | 7.50 | 0.20 |
| Embodiment 8 | Well | 6.60 | 6.76 | 0.16 |
| Embodiment 11 | Well | 7.90 | 8.13 | 0.23 |
| Comparative example 2 | Well | 6.17 | 9.00 | 2.83 |
| Comparative example 5 | Well | 7.23 | 7.55 | 0.32 |
Table 3
| Dispersed | Initial stage viscosity (cPs) | Through the time viscosity (cPs) | Viscosity rising (cPs) | |
| Embodiment 3 | Well | 6.20 | 6.70 | 0.50 |
| Embodiment 4 | Well | 7.20 | 7.60 | 0.40 |
| Embodiment 6 | Well | 7.30 | 7.45 | 0.15 |
| Embodiment 7 | Well | 10.10 | 10.30 | 0.20 |
| Embodiment 12 | Well | 9.95 | 10.75 | 0.80 |
| Comparative example 3 | Well | 6.19 | 7.01 | 0.82 |
| Comparative example 6 | Well | 8.21 | 8.20 | -0.01 |
Test Example 2
The dispersible pigment dispersion of preparation in embodiment 1～12 and the comparative example 1～6 is spun on the glass substrate, measures thickness and contrast gradient.The measuring method of contrast gradient is described below.
On backlight (Meitaku System); With chroma-luminance meter (Topcon BM-5A); Under the 2 degree visuals field; Brightness (I is parallel) when the parallel-nicol of working sample (ニ コ Le) state promptly is in the polarizing axis configured in parallel of the locational polaroid of clamping sample and the brightness (I quadrature) under the quadrature Niccol state are with the ratio of the brightness under the brightness under the parallel-nicol state and the quadrature Niccol state (I parallel/I quadrature) degree as a comparison.
The measuring result of the transparency of filming and thickness and contrast gradient is shown in table 4～6.Table 4, table 5, table 6 are used C.I. Pigment red 177 (Ciba-Geigy corporate system, trade(brand)name " Cromophtal RedA3B "), C.I. pigment Blue 15 respectively: 4 (BASF AG's system, trade(brand)names " Heliogen Blue D7100 "), C.I. Pigment green 16 (BASF AG's system, trade(brand)name " Heliogen Green D9360 ") are as pigment.Here, the state that little height is poor, no concave-convex is uneven is not blured, do not had to the transparent film coated surface that refers to well.Embodiment 1～12 compares with comparative example 1～6, and contrast gradient improves.
Table 4
| Contrast gradient | The transparency | Thickness (μ m) | |
| Embodiment 1 | 590 | Well | 1.99 |
| Embodiment 5 | 588 | Well | 1.99 |
| Embodiment 9 | 591 | Well | 2.00 |
| Embodiment 10 | 586 | Well | 2.01 |
| Comparative example 1 | 500 | Well | 1.99 |
| Comparative example 4 | 487 | Well | 1.98 |
Table 5
| Contrast gradient | The transparency | Thickness (μ m) | |
| Embodiment 2 | 1586 | Well | 1.99 |
| Embodiment 8 | 1580 | Well | 1.99 |
| Embodiment 11 | 1592 | Well | 2.00 |
| Comparative example 2 | 1497 | Well | 2.00 |
| Comparative example 5 | 1530 | Well | 2.03 |
Table 6
| Contrast gradient | The transparency | Thickness (μ m) | |
| Embodiment 3 | 2890 | Well | 2.00 |
| Embodiment 4 | 2870 | Well | 2.00 |
| Embodiment 6 | 2880 | Well | 1.99 |
| Embodiment 7 | 2860 | Well | 2.00 |
| Embodiment 12 | 2790 | Well | 2.00 |
| Comparative example 3 | 2550 | Well | 2.00 |
| Comparative example 6 | 2573 | Well | 2.01 |
Test Example 3
Evaluation is passed through the coating of gap coating after being coated with the back on the glass substrate and passing through ink-jet application with the dispersible pigment dispersion of preparation in embodiment 1～12 and the comparative example 1～6.The result is shown in table 7～9.Table 7, table 8, table 9 use C.I. Pigment red 177 (Ciba-Geigy corporate system, trade(brand)name " CromophtalRed A3B "), C.I pigment Blue 15 respectively: 4 (BASF AG's system, trade(brand)names " Heliogen Blue D7100 "), C.I. Pigment green 16 (BASF AG's system, trade(brand)name " Heliogen Green D9360 ") are as pigment.Be coated with that bad finger is continuous to be coated with the situation that rear nozzle has obstruction, seepage, adheres to solids at injection part repeatedly more than 10 hours.If nozzle has obstruction, seepage, adheres to solids at injection part, can cause the thickness of local film different, occur damaged.Embodiment 1～12 compares with comparative example 1～6, and it is bad coating not occur.
Table 7
| Gap coating is bad | Ink-jet application is bad | |
| Embodiment 1 | Do not have | Do not have |
| Embodiment 5 | Do not have | Do not have |
| Embodiment 9 | Do not have | Do not have |
| Embodiment 10 | Do not have | Do not have |
| Comparative example 1 | Have | Have |
| Comparative example 4 | Have | Have |
Table 8
| Gap coating is bad | Ink-jet application is bad | |
| Embodiment 2 | Do not have | Do not have |
| Embodiment 8 | Do not have | Do not have |
| Embodiment 11 | Do not have | Do not have |
| Comparative example 2 | Do not have | Have |
| Comparative example 5 | Do not have | Have |
Table 9
| Gap coating is bad | Ink-jet application is bad | |
| Embodiment 3 | Do not have | Do not have |
| Embodiment 4 | Do not have | Do not have |
| Embodiment 6 | Do not have | Do not have |
| Embodiment 7 | Do not have | Do not have |
| Embodiment 12 | Do not have | Do not have |
| Comparative example 3 | Do not have | Have |
| Comparative example 6 | Have | Have |
Claims (7)
1. dispersible pigment dispersion; It contains pigment and organic solvent, and it be hydroxyl polycarboxylic acid's ester cpds group of constituting of hydroxyl polycarboxylic acid's ester of 2～6, (b) be the acetoxyl group carbonate group that constitutes of 2～6 acetoxyl group carboxylicesters and (c ') by the carbonatoms of polycarboxylic acid part by the carbonatoms of carboxylic moiety by the carbonatoms of polycarboxylic acid part is at least a kind of organic solvent among the alkoxyl group polycarboxylic acid ester cpds group that constitutes of 2～6 alkoxyl group multi-carboxylate that this organic solvent contains and be selected from (a ').
2. the dispersible pigment dispersion of claim 1; Wherein, to contain from (a) be the hydroxycarboxylic acid ester cpds group that constitutes of 2～6 hydroxycarboxylic acid esters, (b) be the acetoxyl group carbonate group that constitutes of 2～6 acetoxyl group carboxylicesters and (c ') by the carbonatoms of polycarboxylic acid part by the carbonatoms of carboxylic moiety by the carbonatoms of carboxylic moiety to this organic solvent is to select the multiple organic solvent more than a kind respectively at least two group compound groups these three groups of compound groups of alkoxyl group polycarboxylic acid ester cpds group of constituting of 2～6 alkoxyl group multi-carboxylate.
3. the dispersible pigment dispersion of claim 1, wherein this organic solvent further contains at least a kind of organic solvent that is selected among single propylene glycol monomethyl ether and the single propylene glycol methyl ether acetate.
4. the dispersible pigment dispersion of claim 2, wherein this organic solvent further contains at least a kind of organic solvent that is selected among single propylene glycol monomethyl ether and the single propylene glycol methyl ether acetate.
5. each dispersible pigment dispersion of claim 1～4, wherein this organic solvent further contains at least a kind of organic solvent that is selected among alkyl carboxylates class and the aliphatics ketone.
6. each dispersible pigment dispersion of claim 1～4 wherein, except that pigment and organic solvent, also contains resin and/or dispersing auxiliary.
7. the dispersible pigment dispersion of claim 5 wherein, except that pigment and organic solvent, also contains resin and/or dispersing auxiliary.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP001769/07 | 2007-01-09 | ||
| JP2007001769A JP5405000B2 (en) | 2007-01-09 | 2007-01-09 | Pigment dispersion |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101220229A CN101220229A (en) | 2008-07-16 |
| CN101220229B true CN101220229B (en) | 2012-05-23 |
Family
ID=39630318
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2008100022556A Expired - Fee Related CN101220229B (en) | 2007-01-09 | 2008-01-08 | Dye dispersion liquid |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP5405000B2 (en) |
| KR (1) | KR20080065549A (en) |
| CN (1) | CN101220229B (en) |
| TW (1) | TWI422648B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5067282B2 (en) | 2008-06-27 | 2012-11-07 | ソニー株式会社 | Object detection control device, object detection system, object detection control method, and program |
| EP2746349A1 (en) * | 2012-12-21 | 2014-06-25 | Eckart GmbH | Pigment preparation with metal effect pigments, method for their manufacture and use of the same |
| CN108276834A (en) * | 2017-12-22 | 2018-07-13 | 英德科迪颜料技术有限公司 | A kind of water nano mill base of resistance to ethyl alcohol |
| CN108084802B (en) * | 2017-12-22 | 2021-08-10 | 英德科迪颜料技术有限公司 | Ethanol-resistant aqueous glaze nano-grade color concentrate |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5880209A (en) * | 1990-01-13 | 1999-03-09 | Herberts Gmbh | Binder formulation for producing pigment |
| CN1654547A (en) * | 2004-02-13 | 2005-08-17 | 佳能株式会社 | Novel pigment compound, ink, ink cartridge, recording element, recording device and recording method |
| CN1709994A (en) * | 2005-07-05 | 2005-12-21 | 北京国科京彪新材料科技有限公司 | Anticorrosive waterproof nano industrial coating and its preparing method |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06306321A (en) * | 1993-04-26 | 1994-11-01 | Sakata Corp | Ink composition for metal printing |
| JPH09296142A (en) * | 1996-04-30 | 1997-11-18 | Japan Synthetic Rubber Co Ltd | Coloring composition |
| JP2001172541A (en) * | 1999-12-15 | 2001-06-26 | Mitsubishi Pencil Co Ltd | Writing ink composition |
| JP4070066B2 (en) * | 2000-09-12 | 2008-04-02 | 株式会社リコー | Ink jet ink composition |
| JP4783549B2 (en) * | 2003-08-22 | 2011-09-28 | 株式会社Ｄｎｐファインケミカル | Black ink for color pattern defect correction and color filter |
| JP2006225431A (en) * | 2005-02-15 | 2006-08-31 | Sakata Corp | Carbodiimide-based compound and method for producing pigment dispersed composition using the same |
-
2007
- 2007-01-09 JP JP2007001769A patent/JP5405000B2/en not_active Expired - Fee Related
-
2008
- 2008-01-08 KR KR1020080002061A patent/KR20080065549A/en not_active Application Discontinuation
- 2008-01-08 CN CN2008100022556A patent/CN101220229B/en not_active Expired - Fee Related
- 2008-01-08 TW TW097100646A patent/TWI422648B/en not_active IP Right Cessation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5880209A (en) * | 1990-01-13 | 1999-03-09 | Herberts Gmbh | Binder formulation for producing pigment |
| CN1654547A (en) * | 2004-02-13 | 2005-08-17 | 佳能株式会社 | Novel pigment compound, ink, ink cartridge, recording element, recording device and recording method |
| CN1709994A (en) * | 2005-07-05 | 2005-12-21 | 北京国科京彪新材料科技有限公司 | Anticorrosive waterproof nano industrial coating and its preparing method |
Also Published As
| Publication number | Publication date |
|---|---|
| TWI422648B (en) | 2014-01-11 |
| JP2008169251A (en) | 2008-07-24 |
| TW200837151A (en) | 2008-09-16 |
| KR20080065549A (en) | 2008-07-14 |
| JP5405000B2 (en) | 2014-02-05 |
| CN101220229A (en) | 2008-07-16 |
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