CN106752060A - A kind of water base orchil and ink-jet imaging ink and preparation method thereof - Google Patents
A kind of water base orchil and ink-jet imaging ink and preparation method thereof Download PDFInfo
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- CN106752060A CN106752060A CN201611064265.3A CN201611064265A CN106752060A CN 106752060 A CN106752060 A CN 106752060A CN 201611064265 A CN201611064265 A CN 201611064265A CN 106752060 A CN106752060 A CN 106752060A
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Classifications
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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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
- C09B29/0007—Monoazo dyes prepared by diazotising and coupling from diazotized anilines containing acid groups, e.g. CO2H, SO3H, PO3H2, OSO3H, OPO2H2; Salts thereof
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/16—Naphthol-sulfonic acids
-
- 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
- C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
-
- 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
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
-
- 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
- C09B67/0079—Azoic dyestuff preparations
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes
Abstract
The invention provides a kind of water base orchil, including various compounds represented by chemical structural formula (formula 1).Water base orchil of the present invention, stability is high, water resistance and light resistance are good.Present invention also offers the preparation method of above-mentioned water base orchil.The present invention still further provides the ink-jet imaging ink being made of above-mentioned water base orchil, ink jet image is had fine definition, persistence high and high-durability,Wherein Ar is：A is H or SO3M；M is Na+、K+、Li+、NH4 +Or HN (CH3)3 +；B be OH, C is
Description
Technical field
The invention belongs to technical field of ink, more particularly to a kind of water base orchil and ink-jet imaging ink and its
Preparation method.
Background technology
In recent years, with developing rapidly that ink-jet printing system is applied in office and family, in printing quality, have
Significant raising, but the durability of printed matter still has much room for improvement, especially in the ink jet printable product of porous media, due to smelly
The reason for oxygen or illumination, the long-term text for preserving and photo can fade, it is impossible to enough keep its fine definition, persistence high
And high-durability.This requires that printed matter has color fastness to water high, high light-fast fastness, ozone fastness high.To preparing ink jet ink
Stability, water resistance, light resistance of the dyestuff of water etc. propose requirements at the higher level.
The content of the invention
For above-mentioned technical problem, it is an object of the invention to provide a kind of water base orchil and ink-jet imaging ink
And preparation method thereof, to improve orchil stability high, water resistance and light resistance, its preparation method is simple.
The technical solution adopted by the present invention is：
A kind of water base orchil, including various compounds represented by following chemical structural formula (formula 1)：
Wherein Ar is
A is H or SO3M；M is Na+、K+、Li+、NH4 +Or HN (CH3)3 +；
B be-OH, C is
Water base orchil of the present invention, wherein, the orchil is included by following chemical structural formula (formula 2) table
The compound for showing：
Water base orchil of the present invention, wherein, the orchil is included by following chemical structural formula (formula 4) table
The compound for showing：
The preparation method of water base orchil of the present invention, comprises the following steps：
(1) one contracting：Cyanuric Chloride and emulsifying agent, water are beaten to obtain Cyanuric Chloride slurries；Then it is a contracting of 6-7 by pH value
Substitution compound solution is slowly added to obtain mixed liquor in the Cyanuric Chloride slurries, adjusts the mixed liquor pH value to 5-6,
Stirring is reacted completely to amino substance, obtains a contracting solution；
(2) two contractings：By pH value for the 2.4- diamino benzene sulfonic acids or m-phenylenediamine solution of 6-7 are added to institute in step (1)
State in a contracting solution, be warmed up to 40-45 DEG C, regulation pH value is reacted to 2.4- diamino benzene sulfonic acids or m-phenylene diamine (MPD) disappears to 5-8
It is terminal, cooling adds natrium nitrosum, and stirring and dissolving obtains two contracting solution；
(3) diazotising：Under agitation, step (2) the two contractings solution is slowly added drop-wise in cryosel acid, keeping temperature is
0-5 DEG C, natrium nitrosum excess, it is terminal that reaction to amino disappears, and adds sulfamic acid, removes excessive natrium nitrosum and obtains diazonium
Salt；
(4) three contractings：Regulation H acid pH is dissolved in water to 6-7, is warmed up to 40-45 DEG C, after stirring and dissolving, is slowly added into
Chlorobenzoyl chloride, benzene sulfonyl chloride or toluene sulfochloride, regulation pH value to 6-7, the free H acid of control is terminal within 0.5wt%；Instead
Should be to after terminal, regulation pH value to 9-9.5, after temperature rising reflux reacts, three contracting things of lowering the temperature to obtain；
(5) it is coupled：After diazol cools to 0 DEG C described in step (3), three contracting things described in step (4) are added to
In the diazol after cooling, pH value to 8-9 is then adjusted, react 2-4h, it is terminal to be disappeared to diazol, obtains conjugates；
(6) four contractings：By pH value for the four contracting substitution compound solutions of 7-8 are added to described in step (5) in conjugates,
80-90 DEG C is warmed up to, insulation, regulation pH value after reaction, adds the refined salt of 10-15g/L to saltout to 8-9.5, filters, and discards filter
Liquid, filter cake dissolving, solution dialysis, filtering, spray drying obtains final product the water base orchil of following chemical structural formula (formula 3),
Wherein Ar is
A is H or SO3M；M is Na+、K+、Li+、NH4 +Or HN (CH3)3 +；
B is C is
The preparation method of water base orchil of the present invention, comprises the following steps：
(1) one contracting：Cyanuric Chloride and emulsifying agent, water are beaten to obtain Cyanuric Chloride slurries；Then it is a contracting of 6-7 by pH value
Substitution compound solution is slowly added to obtain mixed liquor in the Cyanuric Chloride slurries, adjusts the mixed liquor pH value to 5-6,
Stirring is reacted completely to amino substance, obtains a contracting solution；
(2) two contractings：By pH value for the 2.4- diamino benzene sulfonic acids or m-phenylenediamine solution of 6-7 are added to institute in step (1)
State in a contracting solution, be warmed up to 40-45 DEG C, regulation pH value is reacted to 2.4- diamino benzene sulfonic acids or m-phenylene diamine (MPD) disappears to 5-8
It is terminal, cooling adds natrium nitrosum, and stirring and dissolving obtains two contracting solution；
(3) diazotising：Under agitation, step (2) the two contractings solution is slowly added drop-wise in cryosel acid, keeping temperature is
0-5 DEG C, natrium nitrosum excess, it is terminal that reaction to amino disappears, and adds sulfamic acid, removes excessive natrium nitrosum and obtains diazonium
Salt；
(4) three contractings：Regulation H acid pH is dissolved in water to 6-7, is warmed up to 40-45 DEG C, after stirring and dissolving, is slowly added into
Chlorobenzoyl chloride, benzene sulfonyl chloride or toluene sulfochloride, regulation pH value to 6-7, the free H acid of control is terminal within 0.5wt%；Instead
Should be to after terminal, regulation pH value to 9-9.5, after temperature rising reflux reacts, three contracting things of lowering the temperature to obtain；
(5) it is coupled：After diazol cools to 0 DEG C described in step (3), three contracting things described in step (4) are added to
In the diazol after cooling, pH value to 8-9 is then adjusted, react 2-4h, it is terminal to be disappeared to diazol, obtains conjugates；
(6) it is 10-12.5 with conjugates pH value described in liquid caustic soda regulating step (5), is warmed up to 75-90 DEG C, insulation reaction
4-6h, it is terminal to be disappeared to conjugates；With salt acid for adjusting pH value to 7-9, the refined salt of 10-15g/L is added, be incubated 2h, filtering；Filter
Cake dissolves again, crosses film, and concentration, spray drying obtains final product the water base orchil of following chemical structural formula (formula 5),
Wherein, A is H or SO3M；M is：Na+, K+,Li+,NH4 +Or HN (CH3)3 +；
C is
The preparation method of water base orchil of the present invention, wherein, a contracting substitution compound is adjacent in step (1)
Aminobenzoic acid, ethylene glycol amine, iminodiacetic acid, 5- amino isophathalic acid, 2- aminobenzoic acid -5- sulfonic acid and 2- aminobenzoics
It is a kind of in acid -4- sulfonic acid.
The preparation method of water base orchil of the present invention, wherein, four contracting substitution compounds are ammonia in step (6)
It is a kind of in base ethyl sulfonic acid, the acid of 3- sulfydryl -1- propane sulfonic acid, morpholine and diglycolamine.
The preparation method of water base orchil of the present invention, wherein, a contracting substitution compound described in step (1)
It is 0.9~1.1 with Cyanuric Chloride mol ratio：1.0, preferably 0.95~1.05：1.0, most preferably 0.97~1.0：1.0；Step (2)
Described in Cyanuric Chloride and 2.4- diamino benzene sulfonic acids or m-phenylene diamine (MPD) mol ratio be 0.9~1.1：1.0, preferably 0.9~1.0：
1.0, most preferably 0.95~1.0：1.0；The acid of H described in step (4) and chlorobenzoyl chloride, benzene sulfonyl chloride or tosyl cl molar ratio
It is 1.0：1.0~1.6, preferably 1.0：1.1~1.3, most preferably 1.0：0.97~1.2, H described in step (6) acid and four contractings take
The mol ratio of alternative compound is 1.0：0.9~1.1, preferably 1.0：0.9~1.0, most preferably 1.0：0.95~1.0.
Present invention also offers a kind of ink-jet imaging ink, it is made up of the component of following mass percent：Water base red
Dyestuff 3%, ethylene glycol 5-20%, 1.2- propane diols 5-10%, glycerine 5-10%, N methyl pyrrolidone 3-10%, Proxel
GXL 0.1%, Surfynol 465 0.2% and water 65-75%；The water base orchil be one kind in above-mentioned dyestuff or
Two or more compounds.
The present invention still further provides the preparation method of above-mentioned ink-jet imaging ink, comprise the following steps：It is accurate by proportioning
Standby raw material, after stirring, crosses 0.25 μm of PC film, and filtrate is ink-jet imaging ink.
Beneficial effect of the present invention：
Water base orchil of the present invention, stability is high, water resistance and light resistance are good.
Ink-jet imaging ink of the present invention, for ink-jet imaging ink provides a kind of new dyestuff, makes ink-jet
Image can have fine definition, persistence high and high-durability, will not be faded due to ozone or illumination.
Specific embodiment
Embodiment 1
A kind of water base orchil, is the compound represented by chemical structural formula (formula 1)：
The preparation method of the water base orchil described in the present embodiment, comprises the following steps：
(1) one contracting：In 1000ml beakers, 18.5g (0.1mol) Cyanuric Chlorides and 5wt% emulsifying agents and 100g ice are added
0.5h being beaten together with 50ml water and obtaining Cyanuric Chloride slurries, the emulsifying agent is APG APG10；And with liquid caustic soda (30wt%)
13.8g (0.1mol) ortho-aminobenzoic acid is dissolved in beaker b in 150ml water, regulation pH value obtains ortho-aminobenzoic acid for 6-7
Solution；The o-amino benzoyl acid solution is slowly added in the Cyanuric Chloride slurries, stirring 0.5h is added, is adjusted with soda
Section pH value detects that it is terminal that amino disappears, and obtains a contracting solution to 5-6 with amino indicator；
(2) two contractings：In 250ml beakers, 18.8g is added to roll over hundred (0.1mol) 2.4- diamino benzene sulfonic acid liquid caustic soda
(30wt%) regulation pH value is 6-7, and stirring and dissolving obtains 2.4- diamino benzene sulfonic acid solution in 200ml water；Then will be described
2.4- diamino benzene sulfonic acid solution is added to described in step (1) in a contracting solution, is warmed up to 40-45 DEG C, and pH is adjusted with soda ash
It is worth 5-8, is analyzed with HPLC, is terminal until 2.4- diamino benzene sulfonic acids disappear；Cooling, adds 6.9g natrium nitrosums, stirring
Two contracting solution are dissolved to obtain, it is standby；
(3) diazotising：In 2000ml beakers, 200g ice and 35ml hydrochloric acid are added, obtain cryosel acid, under agitation, will
Two contracting things described in step (2) is slowly added drop-wise in the cryosel acid, is added, 0-5 DEG C of keeping temperature, natrium nitrosum excess, instead
Answer 2h；Detected with amino indicator, it is terminal that amino disappears, and adds sulfamic acid, removes excessive natrium nitrosum, obtains diazonium
Salt, it is standby；
(4) three contractings：300ml water will be dissolved in after the H acid soda ash regulation pH value of 40g 85wt% (0.1mol) to 6-7
In, 40-45 DEG C, after stirring and dissolving is warmed up to, 16g chlorobenzoyl chlorides are slowly added into, while adjusting pH value to 6-7, control with soda
Free H acid is terminal within 0.5wt%；After being reacted to terminal, soda, regulation pH value to 9-9.5, temperature rising reflux reaction are added
2h, three contracting things of lowering the temperature to obtain are standby；
(5) it is coupled：Continue on the rocks in diazol described in step (3), cool to 0 DEG C；By three contracting described in step (4)
Thing is added in the diazol, is added and is adjusted pH value to 8-9 with soda, reacts 2-4h, with H acid detection diazols, diazol
It is terminal to disappear, and obtains conjugates；
(6) four contractings：In 100ml beakers, add tarine 12.5g (0.1mol), add liquid caustic soda (30wt%) and
70ml water, stirring and dissolving, regulation pH value obtains tarine solution to 7-8；The tarine solution is added to step
(5) described in conjugates, 80-90 DEG C is warmed up to, insulation adjusts pH value to 8-9.5 with soda ash, is analyzed with TLC, detection coupling
It is terminal that thing disappears；After reaction terminates, add the refined salt of 10-15wt% to saltout, filter, discard filtrate, filter cake dissolving, solution oozes
Analysis (is less than 60 μ s/cm), filters (0.45 μm of film of GF/A, GF/F glass fiber filter), and spray drying obtains water base orchil.
Embodiment 2~48
The chemical structure of general formula of the water base orchil of embodiment 1~48 is as follows：
The preparation method of the water base orchil of embodiment 2~24, except spent glycol amine, iminodiacetic acid, 5- amino are different
Ortho-aminobenzoic acid is replaced in phthalandione, 2- aminobenzoic acid -5- sulfonic acid or 2- aminobenzoic acid -4- sulfonic acid and step (1)
Corresponding C groups are obtained, is replaced with tarine in the acid of 3- sulfydryl -1- propane sulfonic acid, morpholine or diglycolamine and step (6)
Get corresponding B group in return, the other the same as in Example 1 obtains corresponding water base orchil 2~24.Water base orchil 2~24
Corresponding A, B and C group is as shown in table 1.
Corresponding A, B and C group list of the water base orchil 2~48 of table 1
The preparation method of the water base orchil of embodiment 25~48, except in (2) step with m-phenylene diamine (MPD) replace 2,4- bis-
Aminobenzenesulfonic acid, spent glycol amine, iminodiacetic acid, 5- amino isophathalic acid, 2- aminobenzoic acid -5- sulfonic acid or 2- aminobenzenes
Formic acid -4- sulfonic acid is replaced with ortho-aminobenzoic acid in step (1) and obtains corresponding C groups, with 3- sulfydryl -1- propane sulfonic acid
Acid, morpholine or diglycolamine are replaced with tarine in step (6) and obtain corresponding B group, the other the same as in Example 1,
Obtain corresponding water base orchil 25~48.Corresponding A, B and C group of water base orchil 25~48 is as shown in table 2.
Corresponding A, B and C group list of the water base orchil 25~48 of table 2
Embodiment 49
A kind of water base orchil, is the compound represented by chemical structural formula (formula 2)：
The preparation method of the water base orchil described in the present embodiment, liquid caustic soda is used except replacing with step (6) after coupling
(30wt%) regulation pH value is 10-12.5, is warmed up to 75-90 DEG C, insulation reaction 4-6h；Analyzed with thin-layered chromatography (TLC), extremely
It is terminal that conjugates disappear；With salt acid for adjusting pH value to 7-9, the refined salt of 10-15g/L is added, be incubated 2h, filtering；Filter cake is again
Dissolving, crosses film, and concentration, spray drying obtains water base orchil.
Embodiment 50~60
The chemical structure of general formula of the water base orchil of embodiment 50~60 is as follows：
The preparation method of the water base orchil of embodiment 50~60, m-phenylene diamine (MPD) or 2,4- diamino are used except step (2) is middle
Base benzene sulfonic acid, spent glycol amine, iminodiacetic acid, 5- amino isophathalic acid, 2- aminobenzoic acid -5- sulfonic acid or 2- aminobenzoics
Acid -4- sulfonic acid is replaced with ortho-aminobenzoic acid in step (1) and obtains corresponding C groups, and the other the same as in Example 49 obtains phase
The water base orchil 50~60 answered.Corresponding A, B and C group of water base orchil 50~60 is as shown in table 3.
Corresponding A, B and C group list of the water base orchil 50~60 of table 3
Embodiment 61~120
The chemical structure of general formula of the water base orchil of embodiment 61~120 is as follows：
The preparation method of the water base orchil of embodiment 61~120, benzene first is substituted except benzene sulfonyl chloride is used in step (4)
Outside acyl chlorides, with embodiment 1, embodiment 85~108 is with embodiment 25, the same embodiment of embodiment 109~120 for embodiment 61~84
49, obtain corresponding water base orchil 61~120.Corresponding A, B and C group of water base orchil 61~120 such as institute of table 4
Show.
Corresponding A, B and C group list of the water base orchil 61~120 of table 4
Embodiment 121~180
The chemical structure of general formula of the water base orchil of embodiment 121~180 is as follows：
The preparation method of the water base orchil of embodiment 121~180, except using p-methyl benzene sulfonic chloride in step (4)
Substitute outside chlorobenzoyl chloride, embodiment 121~144 with embodiment 1, embodiment 145~168 with embodiment 25, embodiment 169~
180 with embodiment 49, obtains corresponding water base orchil 121~180.Water base orchil 121~180 corresponding A, B and C
Group is as shown in table 5.
Corresponding A, B and C group list of the water base orchil 121~180 of table 5
Embodiment 181
A kind of ink-jet imaging ink, is made up of the raw material of following mass percent：Water base orchil：3%；Second two
Alcohol：5%；1.2- propane diols 5%, glycerine 5%, N methyl pyrrolidones 6.7%, Proxel GXL 0.1%, Surfynol
465 0.2% and water 75%.
The preparation method of ink-jet imaging ink, comprises the following steps described in the present embodiment：Prepare raw material, stirring by proportioning
After uniform, 0.25 μm of makrolon (PC) film is crossed, filtrate is red ink.
Water base orchil described in embodiment 181 is in 180 kinds of water base orchils in above-described embodiment 1-180
Plant or two or more compounds.Proxel GXL are purchased from the U.S. Austria Qi chemical industry (ARCH) Co., Ltd, and Surfynol 465 is purchased
From Air Prod ＆ Chem of the U.S..
Comparative example 1
A kind of ink-jet imaging ink, is made up of the raw material of following mass percent：Dyestuff：Ethylene glycol：5%；1.2- third
Glycol 5%, glycerine 5%, N methyl pyrrolidones 6.7%, Proxel GXL 0.1%, Surfynol 465 0.2% and water
75%, the chemical structural formula (formula 8) of the dyestuff is as follows：
Form and aspect and vividness to red ink in embodiment 181 and comparative example 1 are compared.By embodiment 181 and right
Red ink is scraped on kodak (Kodak) micropore photographic paper respectively in ratio 1, is surveyed using X Rite XR8200 colour photometers
Color, measures L, a*, b*, C, whereinMeasurement result is as shown in table 6.
The colour photometer of table 6 measures red ink parameter list in embodiment 181 and comparative example 1
| L | a* | b* | C | |
| Embodiment 181 | 55.3 | 74.5 | -1.5 | 74.5 |
| Comparative example 1 | 48.7 | 70.8 | -4.4 | 70.9 |
Remarks：1976 uniform colour spaces recommended by CIE.The space is three-dimensional cartesian coordinate system system, is most to receive wide at present
Chromatic measuring system.With lightness L* and chromaticity coordinate, a*, b* represent position of the color in the colour space.L* represents color
Lightness；A* is red on the occasion of expression, negative values greenness；B* is on the occasion of expression yellow, negative values blueness；C is color saturation.
As can be seen from Table 6, the ink prepared using Monoazo compound of the invention is bright-coloured with preferable brightness
Degree.
Embodiment described above is only that the preferred embodiment of the present invention is described, not to model of the invention
Enclose and be defined, on the premise of design spirit of the present invention is not departed from, those of ordinary skill in the art are to technical side of the invention
Various modifications and improvement that case is made, all should fall into the protection domain of claims of the present invention determination.
Claims (10)
1. a kind of water base orchil, it is characterised in that：Including various compounds represented by following chemical structural formula (formula 1)：
Wherein Ar is
A is H or SO3M；M is Na+、K+、Li+、NH4 +Or HN (CH3)3 +；
B be-OH, C is
2. water base orchil according to claim 1, it is characterised in that：The orchil includes being tied by following chemistry
The compound that structure formula (formula 2) is represented：
3. water base orchil according to claim 1, it is characterised in that：The orchil includes being tied by following chemistry
The compound that structure formula (formula 4) is represented：
4. the preparation method of the water base orchil described in claim 1-3 any one, it is characterised in that：Including following step
Suddenly：
(1) one contracting：Cyanuric Chloride and emulsifying agent, water are beaten to obtain Cyanuric Chloride slurries；Then it is a contracting substitution of 6-7 by pH value
It is slowly added to obtain mixed liquor in the Cyanuric Chloride slurries with compound solution, adjusts the mixed liquor pH value to 5-6, stirring
Reacted completely to amino substance, obtain a contracting solution；
(2) two contractings：By pH value for the 2.4- diamino benzene sulfonic acids or m-phenylenediamine solution of 6-7 are added to one described in step (1)
In contracting solution, 40-45 DEG C is warmed up to, regulation pH value is reacted to 2.4- diamino benzene sulfonic acids or m-phenylene diamine (MPD) disappears for eventually to 5-8
Point, cooling adds natrium nitrosum, and stirring and dissolving obtains two contracting solution；
(3) diazotising：Under agitation, step (2) the two contractings solution is slowly added drop-wise in cryosel acid, keeping temperature is 0-5
DEG C, natrium nitrosum excess, it is terminal that reaction to amino disappears, and adds sulfamic acid, removes excessive natrium nitrosum and obtains diazol；
(4) three contractings：Regulation H acid pH is dissolved in water to 6-7, is warmed up to 40-45 DEG C, after stirring and dissolving, is slowly added into benzene first
Acyl chlorides, benzene sulfonyl chloride or toluene sulfochloride, regulation pH value to 6-7, the free H acid of control is terminal within 0.5wt%；It is reacted to
After terminal, regulation pH value to 9-9.5, after temperature rising reflux reaction, three contracting things of lowering the temperature to obtain；
(5) it is coupled：After diazol cools to 0 DEG C described in step (3), three contracting things described in step (4) are added to cooling
In the diazol afterwards, pH value to 8-9 is then adjusted, react 2-4h, it is terminal to be disappeared to diazol, obtains conjugates；
(6) four contractings：By pH value for the four contracting substitution compound solutions of 7-8 are added to described in step (5) in conjugates, heat up
To 80-90 DEG C, insulation, regulation pH value after reaction, adds the refined salt of 10-15g/L to saltout to 8-9.5, filters, and discards filtrate, filters
Cake dissolves, solution dialysis, and filtering, spray drying obtains final product the water base orchil of following structural formula (formula 3),
Wherein Ar is
A is H or SO3M；M is Na+、K+、Li+、NH4 +Or HN (CH3)3 +；
B is
C is
5. the preparation method of the water base orchil described in claim 1-3 any one, it is characterised in that：Described is water base red
The preparation method of color dyestuff, comprises the following steps：
(1) one contracting：Cyanuric Chloride and emulsifying agent, water are beaten to obtain Cyanuric Chloride slurries；Then it is a contracting substitution of 6-7 by pH value
It is slowly added to obtain mixed liquor in the Cyanuric Chloride slurries with compound solution, adjusts the mixed liquor pH value to 5-6, stirring
Reacted completely to amino substance, obtain a contracting solution；
(2) two contractings：By pH value for the 2.4- diamino benzene sulfonic acids or m-phenylenediamine solution of 6-7 are added to one described in step (1)
In contracting solution, 40-45 DEG C is warmed up to, regulation pH value is reacted to 2.4- diamino benzene sulfonic acids or m-phenylene diamine (MPD) disappears for eventually to 5-8
Point, cooling adds natrium nitrosum, and stirring and dissolving obtains two contracting solution；
(3) diazotising：Under agitation, step (2) the two contractings solution is slowly added drop-wise in cryosel acid, keeping temperature is 0-5
DEG C, natrium nitrosum excess, it is terminal that reaction to amino disappears, and adds sulfamic acid, removes excessive natrium nitrosum and obtains diazol；
(4) three contractings：Regulation H acid pH is dissolved in water to 6-7, is warmed up to 40-45 DEG C, after stirring and dissolving, is slowly added into benzene first
Acyl chlorides, benzene sulfonyl chloride or toluene sulfochloride, regulation pH value to 6-7, the free H acid of control is terminal within 0.5wt%；It is reacted to
After terminal, regulation pH value to 9-9.5, after temperature rising reflux reaction, three contracting things of lowering the temperature to obtain；
(5) it is coupled：After diazol cools to 0 DEG C described in step (3), three contracting things described in step (4) are added to cooling
In the diazol afterwards, pH value to 8-9 is then adjusted, react 2-4h, it is terminal to be disappeared to diazol, obtains conjugates；
(6) it is 10-12.5 with conjugates pH value described in liquid caustic soda regulating step (5), is warmed up to 75-90 DEG C, insulation reaction 4-6h,
Disappeared to conjugates is terminal；With salt acid for adjusting pH value to 7-9, the refined salt of 10-15g/L is added, be incubated 2h, filtering；Filter cake weight
New dissolving, crosses film, and concentration, spray drying obtains final product the water base orchil of following structural formula (formula 5),
Wherein, A is H or SO3M；M is：Na+, K+,Li+,NH4 +Or HN (CH3)3 +
C is
6. the preparation method of the water base orchil according to claim 4 or 5, it is characterised in that：One described in step (1)
Contracting substitution compound be ortho-aminobenzoic acid, ethylene glycol amine, iminodiacetic acid, 5- amino isophathalic acid, 2- aminobenzoic acids-
It is a kind of in 5- sulfonic acid and 2- aminobenzoic acid -4- sulfonic acid.
7. the preparation method of water base orchil according to claim 6, it is characterised in that：Four contracting described in step (6)
Substitution compound is tarine, the acid of 3- sulfydryl -1- propane sulfonic acid, morpholine and one kind in diglycolamine.
8. the preparation method of water base orchil according to claim 7, it is characterised in that：A contracting described in step (1)
Substitution compound and Cyanuric Chloride mol ratio are 0.9~1.1：1.0；Cyanuric Chloride and 2.4- diaminourea described in step (2)
Benzene sulfonic acid or m-phenylene diamine (MPD) mol ratio are 0.9~1.1：1.0；The acid of H described in step (4) and chlorobenzoyl chloride, benzene sulfonyl chloride or first
Benzene sulfonyl chloride mol ratio is 1.0：The mol ratio of the sour and described four contractings substitution compound of 1.0~1.6, H described in step (6) is
1.0：0.9~1.1.
9. a kind of ink-jet imaging ink, it is characterised in that：It is made up of the component of following mass percent：Water base orchil
3%, ethylene glycol 5-20%, 1.2- propane diols 5-10%, glycerine 5-10%, N methyl pyrrolidone 5-10%, Proxel GXL
0.1%, Surfynol 4650.2% and water 65-75%；The water base orchil is the one kind or two in claim 1-3
Water base orchil more than kind.
10. the preparation method of the ink-jet imaging ink described in claim 9, it is characterised in that：Comprise the following steps：By proportioning
Prepare raw material, after stirring, cross 0.25 μm of PC film, filtrate is ink-jet imaging ink.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5831041A (en) * | 1995-11-14 | 1998-11-03 | Sumitomo Chemical Company, Limited | Monoazo compounds and dyeing or printing process for fiber materials using them |
| US6068687A (en) * | 1997-11-20 | 2000-05-30 | Ilford Imaging Switzerland Gmbh | Azo dyes and their preparation and use |
| JP2004083892A (en) * | 2002-07-04 | 2004-03-18 | Nippon Kayaku Co Ltd | Water-soluble monoazo compound and aqueous magenta ink composition and colored article |
| CN103154159A (en) * | 2010-09-06 | 2013-06-12 | 日本化药株式会社 | Ink set for inkjet recording, recording method, and colored body using same |
| JP2015168763A (en) * | 2014-03-07 | 2015-09-28 | 日本化薬株式会社 | Ink composition, inkjet recording method, and colored body |
-
2016
- 2016-11-28 CN CN201611064265.3A patent/CN106752060A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5831041A (en) * | 1995-11-14 | 1998-11-03 | Sumitomo Chemical Company, Limited | Monoazo compounds and dyeing or printing process for fiber materials using them |
| US6068687A (en) * | 1997-11-20 | 2000-05-30 | Ilford Imaging Switzerland Gmbh | Azo dyes and their preparation and use |
| JP2004083892A (en) * | 2002-07-04 | 2004-03-18 | Nippon Kayaku Co Ltd | Water-soluble monoazo compound and aqueous magenta ink composition and colored article |
| CN103154159A (en) * | 2010-09-06 | 2013-06-12 | 日本化药株式会社 | Ink set for inkjet recording, recording method, and colored body using same |
| JP2015168763A (en) * | 2014-03-07 | 2015-09-28 | 日本化薬株式会社 | Ink composition, inkjet recording method, and colored body |
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