CN110366583A - Print ink dispersant composition - Google Patents
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- CN110366583A CN110366583A CN201880014152.3A CN201880014152A CN110366583A CN 110366583 A CN110366583 A CN 110366583A CN 201880014152 A CN201880014152 A CN 201880014152A CN 110366583 A CN110366583 A CN 110366583A
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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
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
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Abstract
The present invention provides a kind of printing ink dispersant composition, contains: the copolymer of alkene and unsaturated dibasic acid amidate or its salt (a) obtained from the amine with the branched alkyl below of carbon atom number 6 or more 10；With the mixed organic solvents (b) of acetic acid esters (b1) and lower alcohol (b2).
Description
Technical field
The present invention relates to printing ink dispersant composition, printing ink composition and printing ink dispersant packages
The manufacturing method of object.
Background technique
Mode of printing has used the off-set oil being respectively applicable in it has been known that there is intaglio printing, hectographic printing, flexographic printing etc.
Ink.In general, ink contains organic solvent or water equal solvent.For example, the solvent as intaglio printing ink, can be used first
Non-aromatic series solvent as the aromatic systems such as benzene, dimethylbenzene, benzene solvent or ethyl acetate, isopropanol etc..Due to ink
Used in resin and additive dissolubility is high, printing when drying property appropriate etc., it is presently preferred to use toluene.However, by
It is reinforced in the concentration control of the revision of the law of labour safety and health, toluene, therefore, for response environment improvement, an urgent demand weight
Solvent composition in new selection ink, without using the ink of toluene, for example used ethyl acetate, isopropanol ink demand
It improves.
It is described in Japanese Unexamined Patent Publication 2009-138115 bulletin, uses dispersing agent group in electronic material oil below
Object is closed, dispersion in the oil of the electronic materials powder such as carbon black is obtained, dispersant composition contains in electronic material oil: choosing
From at least one kind of dispersing agent in amidate below or carboxylate, the amidate or carboxylate are alkene and unsaturation two
The amidate or carboxylate of the copolymer of first acid and be 10~60 relative to the amide rate or esterification yield of unsaturated dibasic acid
Mole %；It is 8.5~22 (cal/cm with solubility parameter3)1/2Non-aromatic family organic solvent.
In addition, disclosing in Japanese Patent Publication 41-17852 bulletin, the copolymerization of alkene and unsaturated dibasic acid is used
The amidate of object is dispersed in particle in the nonaqueous solvents such as dyestuff or pigment.
Summary of the invention
The present invention provides a kind of printing ink dispersant composition of available following printing ink, the off-set oil
Even if the ink non-aromatic family organic solvent small using effect on environment, also has sufficient dispersion performance to colorant, even if
Ink setting is also easy dispersion when being mixed in organic solvent again, and the dispersibility after preservation is excellent.
The present invention relates to a kind of printing ink dispersant compositions, contain: the copolymerization of alkene and unsaturated dibasic acid
Object amidate or its salt (a) obtained from the amine with the branched alkyl below of carbon atom number 6 or more 10；And acetic acid esters
(b1) with the mixed organic solvents (b) of lower alcohol (b2).
Moreover, it relates to which a kind of printing ink composition, contains:
Print ink powder；
The copolymer of alkene and unsaturated dibasic acid utilize with the branched alkyl below of carbon atom number 6 or more 10 amine and
Obtained amidate or its salt (a)；With
The mixed organic solvents (b) of acetic acid esters (b1) and lower alcohol (b2).
Moreover, it relates to a kind of manufacturing method for printing ink dispersant composition comprising:
Alkene is set to react and obtain in the reaction dissolvent containing acetic acid esters (b1) and lower alcohol (b2) with unsaturated dibasic acid
To the process of copolymer；With
Make above-mentioned copolymer amidation using the amine with the branched alkyl below of carbon atom number 6 or more 10 and obtains above-mentioned
The process of the amidate of copolymer.
Moreover, it relates to which purposes of the composition below as printing ink dispersing agent, the composition contain: alkene
The copolymer of hydrocarbon and unsaturated dibasic acid amide obtained from the amine with the branched alkyl below of carbon atom number 6 or more 10
Compound or its salt (a)；With the mixed organic solvents (b) of acetic acid esters (b1) and lower alcohol (b2).
Moreover, it relates to which purposes of the composition below as printing ink, the composition contain: printing ink is used
Powder；The copolymer of alkene and unsaturated dibasic acid utilizes the amine with the branched alkyl below of carbon atom number 6 or more 10 and obtains
The amidate arrived or its salt (a)；With the mixed organic solvents (b) of acetic acid esters (b1) and lower alcohol (b2).
Hereinafter, the copolymer of alkene and unsaturated dibasic acid, which is utilized, has the branched alkane below of carbon atom number 6 or more 10
Amidate obtained from the amine of base or its salt (a) are used as (a) ingredient, acetic acid esters (b1) are used as (b1) ingredient, by lower alcohol
(b2) it is used as (b2) ingredient, above-mentioned mixed organic solvents (b) is regard as (b) ingredient, is illustrated.
Using the present invention, it is capable of providing a kind of printing ink dispersant package of available following printing ink
Object also has colorant and adequately divides even if the non-aromatic family organic solvent that the printing ink is small using effect on environment
Dissipate performance, even if ink setting, when being mixed in organic solvent again, also be easy dispersion, and save after, such as high temperature,
Dispersibility after long-term preservation is excellent.For example, when carrying out intaglio printing, even if printing ink occurs in the roller of intaglio press
Upper drying and consolidating, the consolidation object are mixed into such situation in newly supplied printing ink from falling on roller during roller rotates,
If printing ink composition made of being modulated using printing ink of the invention with dispersant composition, since printing ink is used
Powder is easy to be redispersed in printing ink, is also able to maintain that working efficiency and prints the quality of ink.
Specific embodiment
(printing ink dispersant composition)
(a) ingredient utilizes for the copolymer of alkene and unsaturated dibasic acid has the branch below of carbon atom number 6 or more 10
Amidate obtained from the amine of alkyl or its salt.(a) ingredient is functioned as the dispersing agent of printing ink powder.
As the alkene of composition (a) ingredient, from the viewpoint of obtaining good dispersion performance, preferably carbon atom number 3 with
Upper 12 alkene below, at least one kind of further preferably in diisobutylene and isobutene, more preferable diisobutylene.
As the unsaturated dibasic acid of composition (a) ingredient, from the viewpoint of obtaining good dispersion performance, preferably carbon is former
The aliphatic unsaturated dibasic acid below of subnumber 4 or more 6, further preferably in maleic anhydride, maleic acid and itaconic acid
It is at least one kind of, it is more preferably selected from least one kind of in maleic anhydride and maleic acid.
The alkene of composition monomer as (a) ingredient and the ratio of unsaturated dibasic acid, from obtaining good dispersion performance
From the viewpoint of, alkene/unsaturated dibasic acid molar ratio is preferably 0.25 or more, and further preferably 0.40 or more, it is more excellent
0.50 or more, and preferably 4 are selected as hereinafter, further preferably 2.5 hereinafter, more preferably 2.0 or less.
(a) amidate of the copolymer of the alkene and unsaturated dibasic acid of ingredient can be by making alkene and unsaturation two
The copolymer of first acid and the amine with the branched alkyl below of carbon atom number 6 or more 10 are reacted and are obtained.Amine as used herein
For the amine with the branched alkyl below of carbon atom number 6 or more 10, preferably there is the branched alkyl below of carbon atom number 6 or more 10
Primary amine.Specifically, dissident's amine, 2 ethyl hexylamine, octodrine, isodecyl amine etc. can be enumerated.These amine can be used a kind,
Or two or more is used in mixed way.Above-mentioned branched alkyl possessed by the amine is preferably the branch below of carbon atom number 8 or more 10
Alkyl.
From the viewpoint of obtaining good dispersion performance and good dissolubility to (b) ingredient, as (a) ingredient
The amide rate (relative to unsaturated dibasic acid) of amidate be preferably greater than 60 moles of %, further preferably 70 moles of %
More than, more preferably 80 moles of % or more, and preferably 150 moles of % hereinafter, further preferably 120 moles of % hereinafter,
More preferably 110 moles of % or less.
In addition, the amide rate can be calculated based on the addition mole % of raw material when manufacturing (a) ingredient.Amide rate is super
When crossing 200 moles of %, thus it is speculated that can have free acid amide compound.
The amidate of the copolymer of alkene and unsaturated dibasic acid may be salt.Salt can use amine, glycine betaine etc.
It is neutralized and is obtained.The preferred imidazoline salt of salt, the salt of the imidazolinium compounds of more preferable following formula (1).
(in formula, R1For the alkyl below of carbon atom number 7 or more 21, R2For the hydrocarbon of the divalent below of carbon atom number 1 or more 5
Base.〕
In above-mentioned formula (1), R1Alkyl can enumerate alkyl, alkenyl.In addition, R1Carbon atom number be preferably 8 or more,
More preferable 10 or more, and preferably 22 hereinafter, more preferably 20 or less.R2The alkyl of divalent can enumerate alkylidene.R2's
Carbon atom number is preferably 1 or more, and preferably 4 or less.
When the amidate of the copolymer of alkene and unsaturated dibasic acid is salt, degree of neutralization is preferably 50 moles of % or more,
More preferably 60 moles of %, and preferably 100 moles of % are hereinafter, more preferably 90 moles of % or less.
From the viewpoint of obtaining good dispersion performance and good solubility to non-aromatic family organic solvent, make
Weight average molecular weight for the above-mentioned amidate of (a) ingredient is preferably 700 or more, and further preferably 3000 or more, more preferably
It is 5000 or more, and preferably 500,000 hereinafter, further preferably 300,000 hereinafter, more preferably 100,000 or less.Wherein, this theory
The weight average molecular weight of the amidate of (a) ingredient in bright book is GPC (gel permeation chromatography, polyphenyl second using following conditions
Alkene conversion) value that measures.
Column: α-M+ α-M (TOSOH Co., Ltd's manufacture)
Column temperature: 40 DEG C
Detector: RI
Eluent: 60mmol/L phosphoric acid, 50mmol/L lithium bromide, DMF solvent
Flow velocity: 1.0mL/min
Injection rate: 0.1mL
Standard: polystyrene
In the present invention, from the aggregate rate for improving copolymer and from the viewpoint of obtaining preferred weight average molecular weight, system
Polymerization initiator can be used when making copolymer.Polymerization initiator can enumerate organic peroxide, azo system etc., wherein it is preferred that
Organic peroxide, can specifically enumerate ketal peroxide, hydroperoxides, dialkyl peroxide, diacyl peroxide,
Peroxy dicarbonate, peroxyester can more specifically enumerate benzoyl peroxide, lauroyl peroxide, t-butyl peroxy -2-
Ethylhexoate etc..
From the viewpoint of obtaining good aggregate rate and dispersion performance, the usage amount of polymerization initiator is (relative to insatiable hunger
And binary acid) it is preferably 0.1 mole of % or more, further preferably 0.3 mole of % or more, more preferably 0.5 mole of % or more,
And preferably 20 moles of % hereinafter, further preferably 10 moles of % hereinafter, more preferably 5 moles of % or less.
In curing step after polymerization, for the purpose for the aggregate rate for further increasing copolymer, it can also add
Add polymerization initiator.Usage amount at this time is preferably 0.01 mole of % or more, 0.1 mole of % or less (relative to unsaturated binary
Acid).
It in the present invention, can be together with (a) ingredient, within the scope of the effect of the invention using containing not anti-
Base feed of the mixture of the alkene or unsaturated dibasic acid answered etc. as (a) ingredient.
(a) salt of the preferably above-mentioned amide compound of ingredient, the imidazoline salt of more preferable above-mentioned amidate.
Consider from the worry to environment, the mixed organic solvents of (b) used in the present invention ingredient are that non-aromatic family has
Solvent, in addition, can be used from the viewpoint of the dissolubility of raising (a) ingredient (b1) ingredient acetic acid esters and (b2) at
The mixed organic solvents of the lower alcohol divided.Printing ink of the invention is divided with dispersant composition suitable for modulating so-called oil
Dissipate the printing ink composition of type slurry form.
As the acetic acid esters of (b1) ingredient, the acetic acid esters below of total carbon atom number 2 or more 6 can be enumerated, can specifically be arranged
Lift ethyl acetate, propyl acetate, butyl acetate etc..(b1) ingredient is preferably selected from least one kind of in ethyl acetate and butyl acetate.
In addition, the lower alcohol as (b2) ingredient, can enumerate the alcohol below of carbon atom number 2 or more 6, can specifically enumerate
Isopropanol, normal propyl alcohol, isobutanol, n-butanol etc..(b2) ingredient is preferably selected from least one kind of in isopropanol and n-butanol.
About (b) ingredient, from obtain good dispersion performance and good solubility from (a) ingredient to (b) ingredient sight
Point considers that mass ratio (b1)/(b2) of the content of the content and (b2) ingredient of (b1) ingredient is preferably 0.01 or more, further excellent
Be selected as 0.25 or more, more preferably 0.45 or more, be still more preferably 0.8 or more, and preferably 100 hereinafter, further
Preferably 99 hereinafter, more preferably 50 hereinafter, still more preferably for 9 hereinafter, being still more preferably 3 or less.
Printing ink dispersant composition of the invention can also be containing the organic solvent other than (b) ingredient, in whole
In organic solvent, (b) ratio shared by ingredient is preferably 10 mass % or more, further preferably 30 mass % or more, more excellent
It is selected as 70 mass % or more, and preferably 100 mass % or less, or 100 mass %.
In addition, the content of the printing preferred water of ink dispersant composition of the invention is few.More preferably contain substantially no
Water.Wherein, it " contains substantially no water " and refers to that the content of the water in composition is preferably 5 mass % hereinafter, further preferably 3
Quality % is hereinafter, more preferably 1 mass % or less.
About printing ink dispersant composition of the invention, from the viewpoint of improving dispersibility, (a) ingredient contains
Mass ratio (a)/(b) of amount and the content of (b) ingredient is preferably 0.1 or more, and further preferably 0.2 or more, more preferably 0.3
More than, and preferably 0.9 hereinafter, further preferably 0.7 hereinafter, more preferably 0.5 or less.
From the viewpoint of improving dispersibility, printing ink dispersant composition of the invention contains preferably 10 mass %
Above, further preferred 15 mass % or more, more preferable 20 mass % or more and preferably 80 mass % or less, further it is excellent
Select 60 mass % or less, more preferable 40 mass % (a) below ingredient.
Printing ink dispersant composition of the invention can contain higher alcohol, fatty acid, aliphatic ester, fatty amine etc.
As any ingredient.
In addition, printing ink of the invention uses dispersant composition that can directly use (b) ingredient as printing ink group
The solvent of object is closed, therefore according to composition, only mixed printing ink is used into printing ink dispersant composition of the invention
Powder, it will be able to obtain printing ink composition of the invention.For example, printing ink dispersant composition of the invention can be with
As printing ink vehicle or its solvent and then printing ink composition solvent etc..
From the viewpoint of the Combination for improving and printing ink powder or other organic solvents, printing of the invention
Printing ink composition is preferably liquid.
The present invention provides the composition for containing above-mentioned (a) ingredient and above-mentioned (b) ingredient as printing ink dispersing agent
Purposes.Composition involved in the purposes can be suitably using item described in printing ink composition of the invention.
(printing ink composition)
Printing ink composition of the invention contains printing ink powder, above-mentioned (a) ingredient and above-mentioned (b) ingredient.(a)
The concrete example of ingredient and (b) ingredient and preferred mode are identical as printing ink dispersant composition of the invention.
As printing ink powder, the inorganic particle other than colorant, colorant can be enumerated.
Colorant can enumerate pigment.As pigment, common various inorganic pigments in printing ink, organic can be used
Pigment etc..As inorganic pigment, for example, can enumerate titanium oxide, iron oxide red (Bengala), antimony red, cadmium yellow, cobalt blue, it is dark purple,
The colored pigments such as ultramarine, carbon black, graphite, satin white, zinc white, silica, calcium carbonate, kaolin, clay, barium sulfate, hydrogen-oxygen
Change extender pigments, the aluminium cream containing alumina particles being surface-treated using acrylic resin, the surfaces such as aluminium, talcum to be coated with
The pearl pigments such as the mica of titanium oxide, tin oxide and zirconium oxide.As organic pigment, such as soluble azo face can be enumerated
Material, insoluble azo colour, azo lake pigment, condensed azo pigment, copper phthalocyanine, condensation polycyclic pigment etc..
In addition, calcium phosphate, trbasic zinc phosphate, bentonite, ferrite, oxygen can be enumerated as the inorganic particle other than colorant
Change aluminium, magnesia, white carbon black, cement, gypsum, titanate, silicate etc..
It prints ink and preferably comprises colorant with powder.From the viewpoint of it can obtain good dispersibility, the present invention
Printing ink composition contain preferably 5 mass % or more, further preferred 7 mass % or more, more preferable 9 mass % or more,
And it is preferred that 50 mass % or less, further preferred 30 mass % colorant below.
In addition, printing ink composition of the invention contains the inorganic particle other than colorant as printing ink powder
When, it prints and contains preferably 10 mass % or more, further preferred 20 mass % or more, more preferable 30 mass % in ink powder
Above and the inorganic particle other than preferably 70 mass % or less, further preferred 60 mass % colorant below.
From the viewpoint of it can obtain good dispersibility, printing ink composition of the invention is relative to printing ink
With 100 mass parts of powder, containing it is more than preferably 1 mass parts, it is more than further preferred 2 mass parts, it is more than more preferable 5 mass parts,
And it is preferred that 30 below the mass, further preferably 20 (a) ingredient below the mass.
Printing ink composition of the invention contains preferably 80 mass % or more, further preferred 85 mass % or more, simultaneously
And preferably 95 mass % or less, further preferred 90 mass % (b) below ingredient.
The composition of printing ink composition of the invention can have various settings, for example, intaglio printing printing ink composition
When, the content of each ingredient for example can be as described below.
Colorant preferably 7 mass % or more, 30 mass % or less in the composition
(a) ingredient is relative to 100 mass parts of colorant, and more than preferably 0.5 mass parts 30 below the mass
(b) ingredient preferably 40 mass % or more, 92.5 mass % or less in the composition
About printing ink composition of the invention, the average grain diameter of the discrete particles at 25 DEG C is preferably 3 μm hereinafter, more
Preferably 2.5 μm hereinafter, as an example, preferably 2 μm or so.The lower limit value of average grain diameter is preferably 1.1 μm or more.Separately
Outside, average grain diameter is measured using method documented by embodiment.
Printing ink composition of the invention can contain adhesive, plasticizer etc..As adhesive, such as can enumerate
Ethyl cellulose, acrylic acid, polyvinyl butyral, polyvinyl acetal, polyvinyl alcohol, polyolefin, polyurethane, polyphenyl second
Alkene or their mixture etc..As plasticizer, such as dioctyl phthalate, adipic acid, phosphate, second can be enumerated
Glycol etc..
In addition, the viscosity of printing ink composition of the invention can also be set according to mode of printing.For example, being recessed
When version printing printing ink composition, 25 DEG C of viscosity is preferably 0.5mPas or more 20mPas or less.
The mechanism of the dispersion stability of printing ink composition of the invention is still not clear, thus it is speculated that is to constitute this by being originated from
The group of the unsaturated dibasic acid of (a) ingredient of invention is adsorbed in printing ink powder, from composition (a) ingredient of the invention
Alkene group dissolution diffusion in organic solvent, thus print ink powder dispersion stability improve.
Printing ink composition of the invention is preferably distributed slurry in oil.As obtaining printing ink group of the invention
The method for closing object, can be used common slurried method.For example, can enumerate: dispersing to printing ink of the invention
The method for addition printing ink powder in agent composition and being stirred, mixing；To printing ink with adding this hair in powder
Bright printing ink dispersant composition is simultaneously stirred, the method mixed etc..As the method for stirring, mixing, such as can
To use the common agitating device such as high speed disperser, mixer for well-distribution, ball mill.
In addition, can also carry out when with crushing simultaneously the pigment or slurried coarse granule for making to print ink powder to print
Printing ink dispersant composition of the invention is added in the ore or coarse granule of brush ink powder, is carried out simultaneously with crushing
Slurried method etc..Carrying out slurried method simultaneously with crushing can be used the common wet crushing mill such as ball mill.
The present invention, which provides, contains the composition for printing ink powder, above-mentioned (a) ingredient and above-mentioned (b) ingredient as printing
The purposes of ink.Composition involved in the purposes can suitably apply printing ink dispersant composition and print of the invention
Item described in brush printing ink composition.
(manufacturing method of printing ink dispersant composition or printing ink composition)
The present invention provides a kind of manufacturing method for printing ink dispersant composition comprising: make alkene and unsaturation
Binary acid reacts the process for obtaining copolymer in the reaction dissolvent containing acetic acid esters (b1) and lower alcohol (b2)；With
Make above-mentioned copolymer amidation using the amine with the branched alkyl below of carbon atom number 6 or more 10 and obtains above-mentioned
The process of the amidate of copolymer.
In above-mentioned manufacturing method, the amidate of above-mentioned copolymer is (a) ingredient.Contain (b1) ingredient and (b2) ingredient
Reaction dissolvent can directly as printing ink dispersant composition (b) ingredient.
Item described in printing ink dispersant composition of the invention or printing ink composition of the invention can be with
It is suitable for the invention the manufacturing method of printing ink dispersant composition.
The manufacturing method of printing ink dispersant composition of the invention may include the imidazoline using above-mentioned formula (1)
In compound and the process of the amidate of above-mentioned copolymer.
In addition, the present invention also provides a kind of manufacturing methods of printing ink composition comprising will printing ink powder,
The copolymer of alkene and unsaturated dibasic acid acyl obtained from the amine with the branched alkyl below of carbon atom number 6 or more 10
The step of aminate or its salt (a) and acetic acid esters (b1) are mixed with the mixed organic solvents (b) of lower alcohol (b2).
In above-mentioned manufacturing method, the printing ink dispersion of the invention containing (a) ingredient and (b) ingredient can be used
Agent composition.At this point it is possible to (b1) ingredient and/or (b2) ingredient is added as needed, adjustment composition.Printing ink of the invention
The item described in dispersant composition or printing ink composition of the invention can be adapted for the printing ink composition
Manufacturing method.
Embodiment
Production Example 1
To with blender, thermometer, reflux cooling tube, nitrogen ingress pipe, addition funnel reaction vessel in Malaysia is added
Acid anhydrides (Mitsui Chemicals (strain) manufacture) 70.6g, ethyl acetate (SINOCHEM JAPAN (strain) manufacture) 32.5g and isopropanol (with
It is lower to be slightly denoted as IPA) (JX Energy (strain) manufacture) 32.5g, after being heated to 93 DEG C under nitrogen flowing, the temperature is maintained, and respectively
The acetic acid second of 85 mass % diisobutylene (ball is apt to petrochemistry (strain) and is manufactured) was added dropwise with 1.5 hours using other addition funnels
Ester is with IPA mixed solution 95.0g and as 2 mass %Perbutyl O (manufacture of You company, tert-butyl mistake of polymerization initiator
Oxygen -2 ethyl hexanoic acid ester) ethyl acetate and IPA mixed solution 74.0g, carry out polymerization reaction.After completion of dropwise addition 15 minutes,
Simultaneously add 2 mass %Perbutyl O ethyl acetate and IPA mixed solution 3.0g, later, with 93 DEG C carry out 9 hours it is ripe
Change, completes polymerization reaction.After reaction, cooling, 65 DEG C are maintained at, and using addition funnel with 1 hour dropwise addition 2- ethyl hexyl
Amine (wide honor chemical industry (strain) manufactures) 93.0g, carries out amidation process.After completion of dropwise addition, cure within 2 hours with 65 DEG C.
Later, cooling, 40 DEG C are maintained at, and be added dropwise using 1.5 hours as the oil base hydroxyethyl imidazole quinoline of neutralizer using addition funnel
(manufacture of (strain) eight generation) 185.5g carries out neutralization reaction.After completion of dropwise addition, cure within 1 hour with 40 DEG C, complete reaction, obtain
To the corrective of maleic anhydride/diisobutylene copolymer amidate oil base ethyl imidazol(e) quinoline.By the neutralization of the amidate
The solvent that is used when the amide rate of object, weight average molecular weight (measured using the above method value, similarly hereinafter), synthesis, neutralizer and
Degree of neutralization is shown in table 1.Wherein, oil base hydroxyethyl imidazole quinoline is the R in formula (1)1For oil base, R2For the compound of ethylidene.
By the reaction product obtained using this method directly as printing ink dispersant composition.
Production Example 2~4, comparison manufacturing example 1~8
So that manufacturing condition is become condition shown in table 1, in addition to this, equally operates, obtained containing 1 institute of table with Production Example 1
The amidate shown or in which the reaction product with object or carboxylate.Obtained reaction product is used directly as printing ink divides
Powder composite.
In addition, itaconic acid is manufactured by huge rock field chemical industry (strain), and isobutene is by (strain) Kuraray corporation in table 1
It makes, oleyl amine, octadecylamine, n-octyl amine are by spending king (strain) to manufacture, n-butylamine, n-Decylamine, 2-Ethylhexyl Alcohol, propylene glycol monomethyl ether acetic acid
Ester (PGMEA), methyl iso-butyl ketone (MIBK) (MIBK), toluene, methyl ethyl ketone (MEK), dimethylbenzene with Wako Pure Chemical Industries (strain) by making
Make, dissident's amine, octodrine, isodecyl amine, iso-amylamine, Permethyl 99A amine, stearyl ethyl imidazol(e) quinoline, lauryl ethyl imidazol(e) quinoline by
Tokyo chemical conversion industry (strain) manufacture.
In table 1, mole % is mole % relative to unsaturated dibasic acid.
In table 1, in Production Example 1~4, the amidate of copolymer is (a) ingredient, and when synthesis is using solvent
(b) ingredient.
Examples 1 to 4, comparative example 1~9
Printing ink dispersant composition using table 1 and the dispersing agent compared, modulate printing ink composition, carry out
Evaluation below.Show the result in table 2.
(1) dispersed evaluation (I) (rigid modulated dispersibility)
Be added into the helix tube of 100mL carbon black the MA100 of manufacture (Mitsubishi Chemical's (strain)) 4g that average grain diameter is 24nm,
Solvent, the printing ink dispersant composition of table 1 or the dispersing agent that compares.Wherein, the dispersing agent compared is Lubrizol
24000 (polyethyleneimine amine system dispersing agent, the manufactures of Lubrizol company).In addition, the printing ink dispersant composition of table 1 and
The dispersing agent compared is modulated into solid component using being diluted using solvent identical with the solvent used when synthesis respectively
For the substance of 30 mass %.About the printing ink dispersant composition of table 1, the amount of solid component can be considered as copolymer
The amount of amidate or carboxylate or salt.Wherein, in the dispersing agent compared, solvent is using ethyl acetate/IPA mass ratio
1/1 mixed organic solvents.
Later, handle within 3 hours using the ultrasonic wave distributing device B1510 of Branson company manufacture, modulate slurry.
As printing ink composition.The amount of solvent is modulated, so that the carbon black concentration in printing ink composition becomes 10 matter
Measure %.
The additive amount for preparing printing ink dispersant composition or the dispersing agent compared is 8,10 or 12 mass % (opposite
In carbon black (solid component conversion)) printing ink composition.
The printing ink composition of each dispersing agent additive amount is manufactured just after modulation using Ku Chang manufacturing company
Laser diffraction particle size distribution meter LA-920, the average grain diameter of the carbon black of printing ink composition when to 25 DEG C are measured.It will
As a result it is shown in table 2.
In addition, will average grain diameter be 2 μm of compositions below under each dispersing agent additive amount about printing ink composition
It is evaluated as favorable dispersibility.
(2) dispersed evaluation (II) (redispersibility)
The pressure Reduction Dryer VO-320 manufactured using Advantec company is printed with 80 DEG C, 24 hours to obtained in (1)
Printing ink composition is dried under reduced pressure, and solvent is completely removed.And then secondary ethyl acetate/IPA mass ratio that is added is 1/1
Mixed organic solvents, being adjusted to carbon black concentration is 10 mass %, carries out 1 hour decentralized processing using ultrasonic wave distributing device, obtains
To making the printing ink composition after carbon black redisperse.Then, with (1) equally to the average grain of the carbon black of printing ink composition
Diameter is measured.Show the result in table 2.
In addition, will average grain diameter be 2 μm of compositions below under each dispersing agent additive amount about printing ink composition
It is good to be evaluated as redispersibility.
(3) dispersed evaluation (III) (dispersibility after preservation)
Printing ink composition obtained in (2) is stood 7 in the drying machine DK600 that Yamato company manufactures with 50 DEG C
Day.Later, equally the average grain diameter of the carbon black of printing ink composition is measured with (1).Show the result in table 2.
In addition, will average grain diameter be 2 μm of compositions below under each dispersing agent additive amount about printing ink composition
It is evaluated as favorable dispersibility, it is the better closer to its dispersibility of 2 μm of composition when more than 2 μm.
Claims (15)
1. a kind of printing ink dispersant composition, wherein
Contain:
The copolymer of alkene and unsaturated dibasic acid utilizes the amine with the branched alkyl below of carbon atom number 6 or more 10 and obtains
Amidate or its salt (a)；With
The mixed organic solvents (b) of acetic acid esters (b1) and lower alcohol (b2).
2. printing ink dispersant composition as described in claim 1, wherein
The salt of the amidate is the salt of the imidazolinium compounds of following formula (1),
In formula, R1For the alkyl below of carbon atom number 7 or more 21, R2For the alkyl of the divalent below of carbon atom number 1 or more 5.
3. printing ink dispersant composition as claimed in claim 1 or 2, wherein
(b1) to be at least one kind of in ethyl acetate and butyl acetate, (b2) is at least 1 in isopropanol and n-butanol
Kind.
4. the printing ink dispersant composition as described in claims 1 to 3, wherein
Alkene is at least one kind of in diisobutylene and isobutene.
5. the printing ink dispersant composition as described in Claims 1 to 4, wherein
Unsaturated dibasic acid is at least one kind of in maleic anhydride, maleic acid and itaconic acid.
6. such as printing ink dispersant composition according to any one of claims 1 to 5, wherein
(a) mass ratio (a)/(b) of the content of content and (b) is 0.1 or more 0.9 or less.
7. such as printing ink dispersant composition according to any one of claims 1 to 6, wherein
It is (a) below containing 10 mass % or more, 80 mass % in dispersant composition.
8. such as printing ink dispersant composition according to any one of claims 1 to 7, wherein
(b1) mass ratio (b1)/(b2) of the content of content and (b2) is 0.01 or more 100 or less.
9. a kind of printing ink composition, wherein
Contain:
Print ink powder；
The copolymer of alkene and unsaturated dibasic acid utilizes the amine with the branched alkyl below of carbon atom number 6 or more 10 and obtains
Amidate or its salt (a)；With
The mixed organic solvents (b) of acetic acid esters (b1) and lower alcohol (b2).
10. printing ink composition as claimed in claim 9, wherein
Printing ink with powder is colorant.
11. the printing ink composition as described in claim 9 or 10, wherein
Printing ink composition is relative to printing ink 100 mass parts of powder, below the mass containing more than 1 mass parts 30
(a)。
12. a kind of manufacturing method for printing ink dispersant composition, wherein
Include:
Alkene is set to react and be total in the reaction dissolvent containing acetic acid esters (b1) and lower alcohol (b2) with unsaturated dibasic acid
The process of polymers；With
Make the copolymer amidation using the amine with the branched alkyl below of carbon atom number 6 or more 10 and obtains the copolymerization
The process of the amidate of object.
13. the manufacturing method of printing ink dispersant composition as claimed in claim 12, wherein
Include:
The process that the amidate of the copolymer is neutralized using the imidazolinium compounds of following formula (1),
In formula, R1For the alkyl below of carbon atom number 7 or more 21, R2For the alkyl of the divalent below of carbon atom number 1 or more 5.
14. purposes of the composition as printing ink dispersing agent, wherein
The composition contains:
The copolymer of alkene and unsaturated dibasic acid utilizes the amine with the branched alkyl below of carbon atom number 6 or more 10 and obtains
Amidate or its salt (a)；With
The mixed organic solvents (b) of acetic acid esters (b1) and lower alcohol (b2).
15. purposes of the composition as printing ink, wherein
The composition contains:
Print ink powder；
The copolymer of alkene and unsaturated dibasic acid utilizes the amine with the branched alkyl below of carbon atom number 6 or more 10 and obtains
Amidate or its salt (a)；With
The mixed organic solvents (b) of acetic acid esters (b1) and lower alcohol (b2).
Applications Claiming Priority (3)
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| JP2017-066605 | 2017-03-30 | ||
| JP2017066605A JP6839585B2 (en) | 2017-03-30 | 2017-03-30 | Dispersant composition for printing ink |
| PCT/JP2018/012097 WO2018181155A1 (en) | 2017-03-30 | 2018-03-26 | Dispersant composition for printing ink |
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| CN110366583B CN110366583B (en) | 2022-04-12 |
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| JP7461222B2 (en) * | 2020-05-26 | 2024-04-03 | サカタインクス株式会社 | Gravure printing ink composition for film, printing method, printed matter and laminate |
| JP7509595B2 (en) | 2020-07-21 | 2024-07-02 | サカタインクス株式会社 | Gravure printing ink composition for film |
| KR20240130084A (en) | 2021-12-27 | 2024-08-28 | 카오카부시키가이샤 | Dispersant for capacitor device electrodes |
| JP7339404B2 (en) * | 2021-12-27 | 2023-09-05 | 花王株式会社 | Dispersant composition for electricity storage device electrode |
| WO2023127917A1 (en) | 2021-12-27 | 2023-07-06 | 花王株式会社 | Dispersant composition for power storage device electrodes |
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| JP6839585B2 (en) | 2021-03-10 |
| CN110366583B (en) | 2022-04-12 |
| WO2018181155A1 (en) | 2018-10-04 |
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