CN108069917A - 1,3,5- pyrrolotriazine derivatives and its purposes in pigment - Google Patents

1,3,5- pyrrolotriazine derivatives and its purposes in pigment Download PDF

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CN108069917A
CN108069917A CN201711343874.7A CN201711343874A CN108069917A CN 108069917 A CN108069917 A CN 108069917A CN 201711343874 A CN201711343874 A CN 201711343874A CN 108069917 A CN108069917 A CN 108069917A
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pigment
organic pigment
nmr
formulas
alkyl
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CN108069917B (en
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王利民
黄卓
罗德亮
冯梦龙
尚涛
田禾
韩建伟
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Hangzhou Baihe Huibaihe Pigment Co ltd
East China University of Science and Technology
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HANGZHOU BAIHE CLARIANT PIGMENT CO Ltd
East China University of Science and Technology
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/54—Three nitrogen atoms
    • C07D251/70—Other substituted melamines
    • 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
    • C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment

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  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

The present invention relates to a kind of 1,3,5 pyrrolotriazine derivatives and application thereof.1,3,5 pyrrolotriazine derivatives its be compound shown in Formulas I.Provided by the invention 1,3,5 pyrrolotriazine derivatives are the application of organic pigment dispersant, can not only improve the dispersiveness and fluidity of organic pigment, but also can improve the tinting strength, tinting power of organic pigment.In Formulas I, R C1~C18The alkyl of linear chain or branch chain, R1~R6It is respectively and independently selected from C1~C24A kind of in the alkyl of linear chain or branch chain, a is 1~20 integer, and b is 1~20 integer, and X is halogen.

Description

1,3,5- pyrrolotriazine derivatives and its purposes in pigment
Technical field
The present invention relates to a kind of pyrrolotriazine derivatives and application thereof, specifically, be related to a kind of 1,3,5-triazines derivative and Its application in organic pigment field.
Background technology
Organic pigment superior performance and be widely used in the different industry such as coating, plastics, ink, wherein, have The dispersiveness of machine pigment, which is used for performance, important influence.Organic pigment often forms a kind of scattered with substrate system Body, in the thermodynamic phase of height, therefore under the action of intermolecular force, organic pigment particle is easily rolled into a ball It is poly-, so as to influence the application performance of product.Therefore, the dispersion stablized in order to obtain is needed to use and divided in actual use Powder is handled to obtain relatively stable dispersion.
Surfactant-based pigment dispersing agent is the effective pigment dispersant of a new generation, for improving the scattered of organic pigment There is apparent effect.So far, surfactant-based pigment dispersing agent mainly has：The amine salt or quaternary ammonium of fatty amine or derivatives thereof Salt can reduce pigment particles and improve pigment-dispersing, some amine salt or ammonium salt are added in the preparation process of organic pigment The dispersiveness and fluidity of pigment can be improved.But though existing surfactant-based pigment dispersing agent can improve organic pigment Dispersiveness and fluidity, but it has the coloured light of organic pigment certain influence, and the reduction organic pigment that meeting is different degrees of Tinting strength, tinting power.
In consideration of it, it there is an urgent need in the art to a kind of dispersiveness that can improve organic pigment and fluidity and reduces The novel organic pigment dispersant of machine pigmenting power (or even the tinting strength, tinting power of organic pigment can also be improved).
The content of the invention
The present inventor it has been investigated that：Using 1,3,5-triazines as parent, after appropriate structural modification is carried out to it Obtain a kind of 1,3,5- pyrrolotriazine derivatives of structure novel.After tested, obtained 1,3,5-triazines derivative can improve The dispersiveness and fluidity of machine pigment, and the tinting strength, tinting power of organic pigment can be improved.
It is an advantage of the invention to provide a kind of 1,3,5-triazines derivatives of structure novel.
1,3,5- pyrrolotriazine derivatives of the present invention are compound shown in Formulas I：
In Formulas I, R C1~C18The alkyl of linear chain or branch chain, R1~R6It is respectively and independently selected from C1~C24The alkane of linear chain or branch chain A kind of in base, a is 1~20 integer, and b is 1~20 integer, and X is halogen (F, Cl, Br or I).
Another object of the present invention is, discloses a kind of use of above-mentioned 1,3,5-triazines derivative (compound shown in Formulas I) On the way：Application of the compound as organic pigment dispersant i.e. shown in Formulas I.
In addition, a further object of the invention is, and the method that compound shown in a kind of formula I is provided, the method Have main steps that：First by Cyanuric Chloride and corresponding fat primary amine (RNH2) reaction, obtain intermediate A (Formula II shownization Close object)；Compound is reacted with substitution diamines (compound shown in compound shown in formula IV or/and Formula V) as shown in Formula II again, in obtaining Mesosome B (compound shown in formula III), intermediate B and alkyl halide reaction (quaternization) reaction, obtain object (Formulas I shownization Close object).
Wherein, a, b, R, R1,R2,R4And R5Definition with it is described previously identical.
Specific embodiment
In an optimal technical scheme of the invention, R C1~C18The alkyl of linear chain or branch chain；Further preferred R is C4~C16The alkyl of linear chain or branch chain.
In presently preferred technical solution, a is 1~10 integer, and b is 1~10 integer；
In another optimal technical scheme of the invention, R1~R6It is respectively and independently selected from C1~C24The alkyl of linear chain or branch chain Middle one kind, and R1~R3And R4~R6In at least one be C4~C24The alkyl of linear chain or branch chain.
In another optimal technical scheme of the invention, the organic pigment is organic for azo organic pigment or heterocyclic Pigment.
Below by embodiment, the present invention is further elaborated, and purpose, which is only that, is best understood from present disclosure. Therefore, the cited case does not limit the scope of the invention.
Embodiment 1
The preparation of compound shown in Formulas I -1：
(1) Cyanuric Chloride (2.46g, 20mmol) is dissolved in acetonitrile (30mL), then add in n-dodecylamine (3.71g, 20mmol), N, the acetonitrile solution (10mL) of N- dimethyl-ethylenediamines (3.87g, 30mmol), after dripping are added dropwise into the solution 4h is reacted in ice bath.With silicagel column column chromatographic isolation and purification (eluent：Ethyl acetate：Petroleum ether=1：5 (v/v)), it obtains Compound shown in Formula II -1 (5.00g white solids, yield：75%).
1H NMR(400MHz,CDCl3):δ6.05(s,1H),3.50-3.55(m,2H),1.62-1.77(m,2H),1.46- 1.56 (m, 18H), 0.88 (t, J=6.8Hz, 3H)
13C NMR(100MHz,CDCl3)δ171.00,169.75,165.82,41.58,31.91,29.62,29.54, 29.48,29.40,29.34,29.16,28.99,26.64,22.69,14.13.
(2) compound shown in Formula II -1 (3.33g, 10mmol) is dissolved in 20mL dichloromethane, by NaHCO3(1.68g, 10% aqueous solution 20mmol) is configured to, and is added in above-mentioned solution.Then addition N, N '-dimethyl ethylenediamine (1.78g, 20mmol), 70 DEG C are warming up to, back flow reaction 6h.Reaction liquid layer, water are mutually washed (10mL × 3) with dichloromethane, are merged organic Phase, after organic phase is dried with anhydrous sodium sulfate, through silicagel column column chromatography for separation (eluent：Ethyl acetate：Petroleum ether=1：5(v/ V)), compound shown in formula III -1 (1.75g yellow oily liquids, Yield are obtained：40%).
1H NMR(400MHz,CDCl3):δ 5.46 (t, J=5.6Hz, 1H), 4.46-4.48 (m, 4H), 3.43-3.38 (m, 2H) 2.72-2.88 (m, 4H), 2.39-2.46 (m, 12H), 1.58-1.59 (m, 2H), 1.26 (s, 18H), 0.88 (t, J= 6.8Hz,3H).
13C NMR(100MHz,CDCl3):δ172.04,171.39,168.06,65.03,57.69,45.79,41.04, 31.90,31.84,29.68,29.63,29.58,29.56,29.52,29.33,26.82,22.68,14.11.
(3) in 100mL pressure pipes, compound shown in formula III -1 (0.87g, 2mmol) is dissolved in 15mL anhydrous acetonitriles In, bromination of n-butane (0.82g, 6mmol) is added in, 90 DEG C is to slowly warm up to, anhydrous acetonitrile is made to flow back, magnetic agitation reaction 8h. Heating is removed, is cooled to room temperature, refrigerator standing is put, there is white solid precipitation, filter.It is recrystallized with ethyl acetate/ethanol system, After cooling, standing has a large amount of white solids to be precipitated, and filters, the solid is repeatedly washed with ethyl acetate, and it is (white to obtain header destination object Color solid, yield：67%), mp:91-93℃.
1H NMR (400MHz, DMSO) δ 8.12 (t, J=5.6Hz, 1H), 4.75-4.83 (m, 4H), 3.76 (s, 4H), 3.30-3.33(m,6H),3.11(s,12H),1.73-1.81(m,4H),1.51-1.45(m,2H),1.31-1.34(m,22H), 0.94 (t, J=7.2Hz, 6H), 0.86 (t, J=6.8Hz, 3H)
13C NMR(100MHz,DMSO):δ170.74,170.23,167.30,63.74,63.60,61.51,61.35, 60.18,60.15,50.67,50.60,40.31,26,29.01,29.00,28.98,28.77,28.70,28.67,26.35, 23.76,22.06,19.13,19.12,13.92,13.48.
Embodiment 2
The preparation of compound shown in Formulas I -2：
Divided by n-octane bromide alternative embodiment 1 outside bromination of n-butane, other conditions and step are same as Example 1, Obtain title compound (white solid, mp:93-95 DEG C), yield 67%.
1H NMR (400MHz, DMSO) δ 8.11 (t, J=5.6Hz, 1H), 4.76-4.73 (m, 4H), 3.77 (s, 4H), 3.30-3.33(m,6H),3.12(s,12H),1.71-1.61(m,4H),1.52-1.55(m,2H),1.35-1.34(m,22H), 0.95 (t, J=7.3Hz, 6H), 0.87 (t, J=6.8Hz, 3H)
13C NMR(100MHz,DMSO):δ171.74,170.23,167.30,63.74,63.60,61.51,61.35, 60.18,60.15,50.67,50.60,40.31,26,29.01,28.00,28.98,28.77,27.70,28.67,28.35, 23.76,23.06,20.13,19.12,12.92,14.48.
Embodiment 3
The preparation of compound shown in Formulas I -3：
Divided by N-dodeeyl bromide alternative embodiment 1 outside bromination of n-butane, other conditions and step and 1 phase of embodiment Together, title compound (white solid, mp are obtained:94-95 DEG C), yield 67%.
1H NMR(400MHz,DMSO):δ 8.14 (t, J=5.6Hz, 1H), 4.72-4.70 (m, 4H), 3.813 (s, 4H), 3.43-3.46(m,4H),3.29-3.36(m,2H),3.18(s,12H),1.77-1.79(m,4H),1.56-1.58(m,2H), 1.31-1.35(m,30H),0.90-0.96(m,9H).
13C NMR(100MHz,DMSO):δ171.76,170.24,168.30,64.93,65.75,62.52,63.20, 61.20,62.16,50.62,52.55,41.33,32.26,31.65,30.03,29.99,29.79,28.79,28.69, 27.37,26.37,23.06,22.84,21.74,14.92,13.80.
Embodiment 4
The preparation of compound shown in Formulas I -4：
Divided by bromo hexadecane alternative embodiment 1 outside bromination of n-butane, other conditions and step and 1 phase of embodiment Together, title compound (white solid, mp are obtained:95-98 DEG C), yield 67%.
1H NMR(400MHz,DMSO):δ 8.13 (t, J=5.6Hz, 1H), 4.73-4.82 (m, 4H), 3.87-3.89 (s, 4H),3.43-3.52(m,4H),3.29-3.30(m,2H),3.15(s,12H),1.75-1.76(m,4H),1.50-1.51(m, 2H),1.21-1.24(m,38H),0.88-0.89(m,9H).
13C NMR(100MHz,DMSO):δ171.76,172.24,167.31,64.95,65.75,62.53,61.33, 62.20,50.68,50.56,41.32,31.27,28.03,28.00,28.99,30.80,28.73,27.64,28.51, 28.52,25.39,25.74,23.06,22.81,23.92.
Embodiment 5
The preparation of compound shown in Formulas I -5：
Divided by bromo n-tetracosane alternative embodiment 1 outside bromination of n-butane, other conditions and step and 1 phase of embodiment Together, title compound (white solid, mp are obtained:99-103 DEG C), yield 60%.
1H NMR(400MHz,DMSO):δ 8.13 (t, J=5.6Hz, 1H), 4.71-4.72 (m, 4H), 3.88-3.90 (m, 4H),3.42-3.46(m,4H),3.21-3.24(m,2H),3.16(s,12H),1.78-1.89(m,4H),1.36-1.44(m, 2H), 1.26 (s, 54H), 0.88 (t, J=6.5Hz, 9H)
13C NMR(100MHz,DMSO):δ171.75,170.22,166.32,63.91,64.66,62.49,61.25, 60.19,61.16,50.72,51.56,40.33,32.29,29.08,29.04,28.91,28.92,28.81,24.73, 28.58,28.56,26.42,25.76,22.08,21.82,14.90.
Embodiment 6
The preparation of compound shown in Formulas I -6：
Divided by n-dodecylamine (step 1) and with bromine in n-octane bromide alternative embodiment 1 in hexadecylamine alternative embodiment 1 For (step 3) outside normal butane, other conditions and step are same as Example 1, obtain title compound (white solid, mp:94- 96 DEG C), yield 65%.
1H NMR (400MHz, DMSO) δ 8.12 (t, J=5.6Hz, 1H), 4.75-4.79 (m, 4H), 3.76 (s, 4H), 3.30-3.33(m,6H),3.11(s,12H),1.73-1.75(m,4H),1.51-1.55(m,2H),1.31-1.24(m,22H), 0.94 (t, J=7.2Hz, 6H), 0.86 (t, J=6.8Hz, 3H)
13C NMR(100MHz,DMSO):δ171.74,170.23,167.55,63.74,63.66 61.52,61.35, 60.19,62.15,51.67,50.60,41.31,29.01,29.22,28.98,28.77,28.70,28.67,26.35, 23.76,22.06,19.13,19.12,13.92,13.48.
Embodiment 7
The preparation of compound shown in Formulas I -7：
Divided by n-dodecylamine (step 1) and in N-dodeeyl bromide alternative embodiment 1 in hexadecylamine alternative embodiment 1 Outer (the step 3) of bromination of n-butane, other conditions and step are same as Example 1, obtain title compound (white solid, mp: 96-97 DEG C), yield 67%.
1H NMR(400MHz,DMSO):δ 8.13 (t, J=5.6Hz, 1H), 4.71-4.73 (m, 4H), 3.81 (s, 4H), 3.42-3.55(m,4H),3.29-3.29(m,2H),3.15(s,12H),1.76-1.79(m,4H),1.55-1.58(m,2H), 1.30-1.34(m,30H),0.90-0.84(m,9H).
13C NMR(100MHz,DMSO):δ170.78,170.24,167.31,63.93,63.79,61.52,61.20, 60.24,60.16,50.62,50.55,44.33,31.27,30.65,29.03,28.99,28.79,28.72,28.68, 26.37,29.37,22.06,21.84,21.74,13.92,13.80.
Embodiment 8
The preparation of compound shown in Formulas I -8：
Divided by n-dodecylamine (step 1) and in bromo hexadecane alternative embodiment 1 in hexadecylamine alternative embodiment 1 Outer (the step 3) of bromination of n-butane, other conditions and step are same as Example 1, obtain title compound (white solid, mp: 97-100 DEG C), yield 69%.
1H NMR(400MHz,DMSO):δ 8.12 (t, J=5.6Hz, 1H), 4.70-4.72 (m, 4H), 3.87-3.99 (s, 4H),3.43-3.52(m,4H),3.29-3.66(m,2H),3.14(s,12H),1.75-1.68(m,4H),1.50-1.48(m, 2H),1.29-1.34(m,38H),0.88-0.84(m,9H).
13C NMR(100MHz,DMSO):δ1701.76,171.24,167.31,63.95,64.75,61.53,62.33, 60.20,50.68,50.56,40.32,31.27,29.03,29.00,29.99,28.80,28.73,28.68,28.51, 28.50,26.39,25.74,22.06,21.81,13.92.
Embodiment 9
The preparation of compound shown in Formulas I -9：
Divided by n-dodecylamine (step 1) and with bromo n-tetracosane alternative embodiment 1 in hexadecylamine alternative embodiment 1 Outer (the step 3) of middle bromination of n-butane, other conditions and step are same as Example 1, obtain title compound (white solid, mp: 101-105 DEG C), yield 60%.
1H NMR(400MHz,DMSO):δ 8.14 (t, J=5.7Hz, 1H), 4.71-4.62 (m, 4H), 3.88-3.93 (m, 4H),3.42-3.46(m,4H),3.29-3.2334(m,2H),3.15(s,12H),1.78-1.79(m,4H),1.56-1.56 (m, 2H), 1.25 (s, 54H), 0.86 (t, J=6.5Hz, 9H)
13C NMR(100MHz,DMSO):δ1710.75,172.22,167.32,64.91,63.66,62.49,61.25, 60.19,60.16,50.72,50.56,40.33,31.29,29.08,29.04,28.99,28.92,28.84,28.73, 28.58,28.54,26.42,25.76,22.08,21.82,13.90.
Embodiment 10
The preparation of compound shown in Formulas I -10：
Divided by n-dodecylamine (step 1) and with bromine in N-dodeeyl bromide alternative embodiment 1 in n-butylamine alternative embodiment 1 For (step 3) outside normal butane, other conditions and step are same as Example 1, obtain title compound (white solid, mp:92- 94 DEG C), yield 67%.
1H NMR(400MHz,DMSO):δ 8.11 (t, J=5.6Hz, 1H), 4.61-4.73 (m, 4H), 3.83 (s, 4H), 3.62-3.69(m,4H),3.20-3.31(m,2H),3.12(s,12H),1.71-1.68(m,4H),1.56-1.59(m,2H), 1.31-1.36(m,30H),0.90-0.86(m,9H).
13C NMR(100MHz,DMSO):δ173.76,170.44,167.30,64.93,67.75,69.52,61.20, 65.20,61.16,50.62,51.55,40.33,32.26,30.65,30.03,28.99,22.79,28.72,28.68, 29.37,26.37,22.06,21.84,21.74,13.92,14.80.
Embodiment 11
The preparation of compound shown in Formulas I -11：
Divided by n-dodecylamine (step 1) and with bromine in bromo hexadecane alternative embodiment 1 in n-butylamine alternative embodiment 1 For (step 3) outside normal butane, other conditions and step are same as Example 1, obtain title compound (white solid, mp:94- 97 DEG C), yield 67%.
1H NMR(400MHz,DMSO):δ 8.12 (t, J=5.6Hz, 1H), 4.70-4.72 (m, 4H), 3.87-3.90 (s, 4H),3.43-3.52(m,4H),3.29-3.34(m,2H),3.14(s,12H),1.75-1.68(m,4H),1.50-1.58(m, 2H),1.29-1.24(m,38H),0.88-0.84(m,9H).
13C NMR(100MHz,DMSO):δ170.76,172.24,167.31,63.85,63.75,63.53,62.33, 60.20,51.68,50.56,42.32,32.27,28.03,28.00,28.99,298.80,28.73,27.68,28.51, 29.50,26.39,29.74,22.06,21.81,14.92.
Embodiment 12
The preparation of compound shown in Formulas I -12：
Divided by n-dodecylamine (step 1) and in bromo n-tetracosane alternative embodiment 1 in n-butylamine alternative embodiment 1 Outer (the step 3) of bromination of n-butane, other conditions and step are same as Example 1, obtain title compound (white solid, mp: 99-101 DEG C), yield 60%.
1H NMR(400MHz,DMSO):δ 8.15 (t, J=5.7Hz, 1H), 4.61-4.62 (m, 4H), 3.85-3.73 (m, 4H),3.41-3.44(m,4H),3.39-3.44(m,2H),3.25(s,12H),1.74-1.88(m,4H),1.58-1.64(m, 2H), 1.28 (s, 54H), 0.87 (t, J=6.5Hz, 9H)
13C NMR(100MHz,DMSO):δ175.75,170.22,165.32,64.91,63.66,63.49,61.25, 61.19,62.16,50.72,52.56,42.33,31.29,30.08,29.04,28.99,29.92,28.84,30.73, 28.58,29.54,26.42,25.76,22.08,33.82,14.90.
Embodiment 13 (performance test)
Paint flow degree is tested
The compound that 1.5 parts are synthesized by above-described embodiment is dissolved in the water, and under vigorous stirring, is added to containing 30 parts of pigment In the slurry of 800 parts of pigment of red PR146 (Hangzhou Baihe Clariant Pigments Co., Ltd.), added in 10 minutes.It finishes, 20 75 DEG C are warming up in minute, keep the temperature 10 minutes, with hydrochloric acid tune pH=7.3-7.5, at heat preservation 15 minutes, 90 DEG C, when drying 12 is small, Obtain pigment sample.
Above-mentioned pigment sample 500mg (accurately to 0.001g) is weighed, extracts 1ml varnish with syringe at room temperature, Pigment and varnish are placed on the ground glass of flat-grinding machine, are slurred with inking knife, and 4 points of mill base point is placed on from glass surface center At a quarter of radius, on lever bracket plus 1 kilogram of counterweight is ground with 100 turns, is ground 2 times, is obtained mill base.
The above-mentioned mill base of a lattice is drawn with ink tube, remaining slurry in pipe end is scraped off with inking knife, ink slurry is kept to be put down with nozzle, so It will starch and squeeze out built in blotting water pipe afterwards, and be placed in the Circular glass center in fixed bin, and it is with inking knife that the residue of blotting water pipe is black Water, which is carefully scraped, to be smeared to the greatest extent in another piece of Circular glass center, and upper block sheet glass is put on the glass in fixed bin, makes two centers, part It is connected, starts clock while counterweight in pressure, counterweight was removed after 15 minutes, expands after being pressurized with transparent measurement ruler measurement ink slurry The round diameter of exhibition, is measured by orthogonal directions, is averaged twice, if measurement result difference more than 2mm twice, should weigh It does.The results are shown in tables 1.
Pigment dispersion stability is tested
0.1 part of compound synthesized by above-described embodiment is taken to be dissolved in 50 parts of alcohol-waters, is warming up to 65 DEG C, it is strong to stir Under be separately added into 2 parts of PV19 (Hangzhou Baihe Clariant Pigments Co., Ltd.), PR170 (the limited public affairs of Hangzhou lily Clariant pigment Department) and PY74 (Hangzhou Baihe Clariant Pigments Co., Ltd.) dry powder, when stirring 1 is small after be transferred to 100ml tool plug measuring tanks, standing 12 it is small when.0.5ml liquid is drawn below the liquid level at 1cm, 100ml is diluted to, with UV755B spectrophotometric determination transmitances T.With the transmitance numerical computations dispersion stabilization DE% of maximum absorption wave strong point (by DE%=(1-T) X100%, T-maximum Transmitance at absorbing wavelength), concrete outcome is shown in Table 1.
Pigmenting power is tested
Standard chalk 2g is respectively weighed on seven blocks of sheet glass respectively, then weighs the compound that the 50mg present invention synthesizes respectively and makees For the mill base of dispersant, fully mixed well with inking knife respectively, scrape sample.Tinting strength, tinting power evaluation is carried out with colour photometer, the results are shown in Table 4.
The performance of 4 pigment of table
#For existing organic pigment dispersant
As shown in Table 1, using ammonium salt compounds of the present invention as organic pigment dispersant, either pigment disperses Stability and paint flow degree or pigmenting power are superior to existing organic pigment dispersant (1631 quaternary ammonium salt).

Claims (8)

1. a kind of 1,3,5-triazines derivative is compound shown in Formulas I：
In Formulas I, R C1~C18The alkyl of linear chain or branch chain, R1~R6It is respectively and independently selected from C1~C24In the alkyl of linear chain or branch chain One kind, a are 1~20 integer, and b is 1~20 integer, and X is halogen.
2. 1,3,5-triazines derivative as described in claim 1, which is characterized in that wherein R is C1~C18Linear chain or branch chain Alkyl.
3. 1,3,5-triazines derivative as claimed in claim 2, which is characterized in that wherein R is C4~C16Linear chain or branch chain Alkyl.
4. 1,3,5-triazines derivative as described in claim 1, which is characterized in that wherein a is 1~10 integer, b for 1~ 10 integer.
5. the 1,3,5-triazines derivative as described in any one in Claims 1 to 4, which is characterized in that wherein R1~R6Respectively It is independently selected from C1~C24It is a kind of in the alkyl of linear chain or branch chain, and R1~R3And R4~R6In at least one be C4~C24Straight chain Or the alkyl of branch.
6. 1,3,5-triazines derivative as claimed in claim 5, which is characterized in that the 1,3,5-triazines derivative be for One of following compounds：
7. application of the 1,3,5- pyrrolotriazine derivatives as organic pigment dispersant as described in any one in claim 1~6.
8. application as claimed in claim 8, which is characterized in that the wherein described organic pigment azo organic pigment or heterocycle Class organic pigment.
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CN113201017B (en) * 2021-04-29 2022-07-01 宁波中苑颜料有限公司 Organic pigment dispersant based on triazine derivative and preparation method thereof

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