CN104478876A - N,N'-dimethyl-3,4,9,10-perylenetetracarboxylic diimide derivative and application thereof - Google Patents
N,N'-dimethyl-3,4,9,10-perylenetetracarboxylic diimide derivative and application thereof Download PDFInfo
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- CN104478876A CN104478876A CN201410686779.7A CN201410686779A CN104478876A CN 104478876 A CN104478876 A CN 104478876A CN 201410686779 A CN201410686779 A CN 201410686779A CN 104478876 A CN104478876 A CN 104478876A
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- UUEMBUMWMJAXAK-WHLOCSMTSA-N C[C@H](c1ccc(C2=CC=C3C([O]4C5C4)=O)c4c1C1=CCC4C(CC4)C2C3=C4C5=O)OC1=O Chemical compound C[C@H](c1ccc(C2=CC=C3C([O]4C5C4)=O)c4c1C1=CCC4C(CC4)C2C3=C4C5=O)OC1=O UUEMBUMWMJAXAK-WHLOCSMTSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
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- 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/62—Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/006—Preparation of organic pigments
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Abstract
The invention relates to an N,N'-dimethyl-3,4,9,10-perylenetetracarboxylic diimide derivative and application thereof. The N,N'-dimethyl-3,4,9,10-perylenetetracarboxylic diimide derivative refers to the compound shown as a formula II in the specification or salts thereof. The designed and synthesized N,N'-dimethyl-3,4,9,10-perylenetetracarboxylic diimide derivative can be used for preparing perylene pigments such as C.I.pigment red 149. The perylene pigment prepared by the N,N'-dimethyl-3,4,9,10-perylenetetracarboxylic diimide derivative disclosed by the invention has large specific surface area and narrow particle size distribution.
Description
Technical field
The present invention relates to the application in Yi Zhong perylene tetracid diimide derivative and Bei perylene pigments thereof, specifically, relate to Yi Zhong perylene tetracid diimide derivative and the application in preparation C.I. pigment red 149 thereof.
Background technology
In perylene pigments, C.I. pigment red 149 (its structure is such as formula I Suo Shi) is a red high performance pigment, there is high thermostability, sun-proof and fastness to weathering, be particularly useful for the painted of high-grade plastics, have very high resistance to migration fastness in the plastic.
C.I. pigment red 149 can synthesize by known method, as following author in their works the method that discloses: Shen Yongjia, the kind of pigment dyestuff and application, Chemical Industry Press, 2002,357-375 page; H.Zollinger, " Color Chemistry ", VCH Verlagsgessellschaft, 1991, P227; M.A.Perkins, " Pyridines and Pyridones " edits at " TheChemistry of Synthetic Dyes and Pigments " H.A.Lubs, Malabar, Fla, Robert E, KriegerPublishing Company, 1955, P481-482.
The C.I. pigment red 149 obtained by above-mentioned synthetic method, can't use as pigment, and from the angle of application, it is only the crude product of pigment, and the processing having to pass through certain pigmenting technique could use as pigment.The object of pigmenting processing is the size distribution making crude product pigment, specific surface area, and even crystalline structure changes.Concrete principle can be see: K.Merkle andH.Schafer, " Surface Treatment of Organic Pigments " is at Pigment Handbook, Vol.III (New York:John Wiley & Sons, Inc., 1973), P157; R.B.McKay, " The Development of Organic Pigments withParticular Reference to Physical Form and Consequent Behavior in Use ", Rev.Prog.Coloration, 10,25-32 (1979); R.B.McKay, " Control of the application performance of classical organic pigments ", JOCCA, 89-93 (1989).
CN 1310203A and CN 1563200A all relates to preparation method's (comprising the pigmenting step of crude pigment product preparation and crude pigment product) of C.I. pigment red 149.The C.I. pigment red 149 using prior art to prepare can be applicable to the demand in market at that time.Along with the development of society, human consumer requires also more and more higher to the application performance of fine chemicals.Thereupon, the performance of this area to C.I. pigment red 149 it is also proposed higher requirement, that is: the user of C.I. pigment red 149 wishes that the size distribution of used C.I. pigment red 149 is narrower, and granules of pigments more easily disperses (feature is that its specific surface area wants large).Because the narrow diameter distribution of C.I. pigment red 149, mean that the color of pigment is tending towards more bright-coloured; And C.I. pigment red 149 easily disperses, mean that pigment was more prone to mixing of plastics (C.I. pigment red 149 is mainly used in the painted of plastics).So, the time of processing can be saved, enhance productivity.
In the technology (as CN 1563200A) of existing preparation C.I. pigment red 149, in pigmenting step, Jia Ru perylene tetracid diimide derivative, as dispersion agent, can play a role, but effect is unsatisfactory, is still had room for improvement usually.
Given this, narrower and there is the C.I. pigment red 149 of more bigger serface (surface-area (BET) of C.I. pigment red 149 adopting prior art to prepare is about 60cm for obtaining size distribution
2/ g) become ultimate aim of the present invention.
Summary of the invention
The present inventor, through extensively and further investigation, designs and synthesizes a kind of novel structure perylene tetracid diimide derivative.Meanwhile, the present inventor finds after deliberation: in crude pigment product preparation process, adds Shu perylene tetracid diimide derivative, and the size distribution of the pigment of gained is narrower and have more bigger serface, can meet the requirement of use department.
Therefore, one object of the present invention is, provides a kind of novel structure perylene tetracid diimide derivative.
Suo Shu perylene tetracid diimide derivative of the present invention, it is characterized in that, Suo Shu perylene tetracid diimide derivative is compound shown in formula II, or its salt:
In formula II, R
1~ R
10independently be selected from: hydrogen (H) or C
1~ C
6straight or branched alkyl in a kind of, and R
1~ R
5in have one at least for C
1~ C
6straight or branched alkyl and R
6~ R
10in have one at least for C
1~ C
6straight or branched alkyl; M is the integer of 1 ~ 4; N is the integer of 1 ~ 4.
Another object of the present invention is, a kind of purposes of Shu perylene tetracid diimide derivative in announcement, the application namely in Bei perylene pigments (as C.I. pigment red 149 etc.).
In addition, the present invention also provides the method for compound shown in a kind of preparation formula II, and described method comprises the steps:
(1) You perylene acid anhydride (shown in formula III compound) obtains the step of compound shown in formula IV through halogenation;
(2) compound shown in formula IV and corresponding fortified phenol
be obtained by reacting the step of compound shown in formula V; With
(3) compound shown in formula V and corresponding sulfonic compound
be obtained by reacting the step of target compound (shown in formula II compound);
Wherein, X is halogen (F, Cl, Br or I); R
1~ R
10, the definition of m with n is with described identical above.
Accompanying drawing explanation
Fig. 1 is the BET specific surface curve of the C.I. pigment red 149 finished product of the sample prepared by embodiment 2;
Fig. 2 is the grain size distribution curve of the C.I. pigment red 149 finished product of the sample prepared by embodiment 2;
Fig. 3 is the BET specific surface curve of the C.I. pigment red 149 finished product of the sample prepared by embodiment 3;
Fig. 4 is the grain size distribution curve of the C.I. pigment red 149 finished product of the sample prepared by embodiment 3;
Fig. 5 is the BET specific surface curve of the C.I. pigment red 149 finished product of the sample prepared by comparative example;
Fig. 6 is the grain size distribution curve of the C.I. pigment red 149 finished product of the sample prepared by comparative example.
Embodiment
In the present invention's optimal technical scheme, R
1~ R
10independently be selected from: H or C
1~ C
4straight or branched alkyl in a kind of, and R
1~ R
5in have one at least for C
1~ C
4straight or branched alkyl and R
6~ R
10in have one at least for C
1~ C
4straight or branched alkyl; M is 1 or 2; N is 1 or 2.
Preferred technical scheme is further: R
1~ R
10independently be selected from: H or C
4straight or branched alkyl in a kind of, and R
1~ R
5in have one at least for C
4straight or branched alkyl and R
6~ R
10in have one at least for C
4straight or branched alkyl.
Further preferred technical scheme is: R
1~ R
10independently be selected from: H or C
4straight or branched alkyl in a kind of, and R
1~ R
5in only have one for C
4straight or branched alkyl and R
6~ R
10in only have one for C
4straight or branched alkyl.
Further preferred technical scheme is again: R
1~ R
10independently be selected from: a kind of in H or the tertiary butyl, and R
1~ R
5in only have one for the tertiary butyl and R
6~ R
10in only have one for the tertiary butyl.
Most preferred technical scheme is: R
1~ R
10in, except R
3and R
8for outside the tertiary butyl, all the other are H.
In another optimal technical scheme of the present invention, to prepare C.I. pigment red 149, set forth the purposes of put forward Gong perylene tetracid diimide derivative of the present invention further, that is:
One prepares the method for C.I. pigment red 149 (shown in formula I compound), and it comprises the steps:
(1) step of C.I. pigment red 149 crude product is prepared; And
(2) the pigmenting procedure of processing of C.I. pigment red 149 crude product; It is characterized in that, in step (1) implementation process, add compound shown in formula II, or its salt.
Further preferred technical scheme is:
One prepares the method for C.I. pigment red 149 (shown in formula I compound), and it comprises the steps:
(perylene acid anhydride is dissolved in the aqueous solution of alkali (as Strong oxdiative sodium or Strong oxdiative potassium etc.) by 1), heating makes it dissolve completely, be cooled to room temperature, add 3 again, compound or its salt shown in 5-xylidine and formula II, after mixing, regulate the pH value of material to neutral (pH value is 6 ~ 7), this material is moved in withstand voltage still, airtight, 180 DEG C ~ 200 DEG C are warmed up under stirring, reaction is followed the tracks of in sampling, question response Wu Zhong perylene acid anhydride exhausts, then stopped reaction, cool to room temperature, filter, filter cake obtains N after washing and drying, N '-two (3 ', 5 '-3,5-dimethylphenyl) perylene four pyromellitic imide (C.I. pigment red 149 crude product).
(2) above-mentioned C.I. pigment red 149 crude product is put into ball mill, add steel ball, grinding aid (if sodium-chlor, sodium sulfate are or/and sodium carbonate etc.), organic acid (as solid-state citric acid, succinic acid or tosic acid etc.) and organic solvent (if toluene, dimethylbenzene, sherwood oil, ethyl acetate, butylacetate, propyl carbinol are or/and isopropylcarbinol etc.), ball milling 3 ~ 6 hours, being poured into by ball milling material in the water medium containing the acidity of tensio-active agent boils boils 1 ~ 2 hour, after filtration, washing and dry C.I. pigment red 149 finished product.
Further preferred technical scheme is again:
The add-on of grinding aid is 3 ~ 10 times of C.I. pigment red 149 crude product weight; More preferably technical scheme is: the add-on of grinding aid is 5 ~ 7 times of C.I. pigment red 149 crude product weight.
Organic acid add-on is the 1wt% ~ 10wt% of C.I. pigment red 149 crude product weight; More preferably technical scheme is: organic acid add-on is the 4wt% ~ 7wt% of C.I. pigment red 149 crude product weight.
The add-on of organic solvent is the 1wt% ~ 10wt% of C.I. pigment red 149 crude product weight; More preferably technical scheme is: the add-on of organic solvent is the 4wt% ~ 7wt% of C.I. pigment red 149 crude product weight.
The add-on of compound or its salt shown in formula II is the 1wt% ~ 10wt% of C.I. pigment red 149 crude product weight; More preferably technical scheme is: the add-on of compound or its salt shown in formula II is the 4wt% ~ 7wt% of C.I. pigment red 149 crude product weight.
In addition, the present invention is to tensio-active agent used and have no special requirements, and the existing tensio-active agent for C.I. pigment red 149 crude product pigmenting is all suitable for the present invention.
The present invention's tensio-active agent used can be aniorfic surfactant, cationic surfactant or nonionic surface active agent, or their mixture.
Suitable aniorfic surfactant has: the condenses of lipid acid and taurine, the condenses of lipid acid and N methyl taurine, the condenses of lipid acid and hydroxyethylsulfonic acid, alkyl benzene sulphonate (ABS), alkyl naphthalene sulfonic acid, the sulfuric ester of alkylphenol polyoxyethylene, the sulfuric ester of fatty alcohol-polyoxyethylene ether, the sulfuric ester of fatty amide polyoxyethylene ether, dialkyl succinylsuccinate monoamide, alkenyl succinic acid monoesters, fatty alcohol-polyoxyethylene ether sulfuric acid succinate monoester, alkylsulphonic acid, lipid acid L-glutamic acid condenses is or/and alkylsurfuric acid succinate monoester, wherein said lipid acid refers to: palmitinic acid, stearic acid, oleic acid,
Suitable cationic surfactant is: quaternary ammonium salt, aliphatic amide alcoxyl hydrochlorate, alcoxyl acid polyamines, aliphatic amine polyoxyethylene ether, and aliphatic amide is or/and diamines and the polyamine that derived by aliphatic amide and fatty alcohol;
Suitable nonionic surface active agent is as amine oxide, fatty alcohol-polyoxyethylene ether, aliphatic alcohol polyethenoxy ester, trimethyl-glycine (as fatty acid amide-N-CAB), fat alcohol phosphate, fatty alcohol-polyoxyethylene ether, fatty amide ethoxy hydrochlorate, the oxidation of fat enol adds and thing, and polyoxyethylene alkylphenol ether is or/and poly N-vinyl pyrrolidone (PVP).
The present invention in the crude product preparation process (namely in step (1)) of C.I. pigment red 149 (shown in formula I compound), compound or its salt shown in adding type II.So, the formation of compound molecule crystal shown in the participatory of compound or its salt molecule shown in formula II I, in the lattice of compound shown in the entry type of compound or its salt molecule shown in formula II I, the regularity of the crystal of compound shown in suppressed FCM I.The crude pigment product of gained is processed (as having under grinding aid, organic acid and organic solvent existence condition through pigmenting again, carry out ball milling, again ball milling material is poured in the water medium containing the acidity of tensio-active agent and carries out aftertreatment, after filtration, washing, drying and other steps) C.I. pigment red 149 finished product.
Compared with the C.I. pigment red 149 (finished product) prepared by prior art, the C.I. pigment red 149 (finished product) obtained by technical scheme provided by the invention, its size distribution is narrower and have more bigger serface.
Below will the present invention is described in detail by embodiment, but the cited case does not limit the scope of the invention:
Embodiment 1
The synthesis of N, N '-two (2-sulfoethyl)-1,7-bis-(4-tertiary butyl phenoxy group)-3,4,9,10-perylene four pyromellitic imide (shown in formula II a compound).
The synthesis of bromo-3,4,9, the 10-perylene tetracid dianhydrides of (1) 1,7-bis-(shown in formula IV a compound):
In the 1000mL four-hole boiling flask being furnished with device for absorbing tail gas, add the 450mL vitriol oil with perylene acid anhydride (29g, 74.0mmol), be warmed up to 55 DEG C, insulated and stirred 30h, add I
2(0.7g), be warming up to 85 DEG C, drip the sulphuric acid soln of bromine (8.2mL, 162.8mmol), add in 2.5h.Finish, insulation reaction 30h.Be cooled to room temperature, dropwise add water (100mL), solid is separated out, sand core funnel filters.Filter cake first uses 80%H
2sO
4(250mL) wash, then be washed to filtrate in neutral, dry, obtain compound (32.4g) shown in bright red solid formula IV a, productive rate 80%.Mp>300℃。
MS(EI
+)m/z(％):550([M+2]
+,100)，548(M
+,31.57)，246(31.53)，123(16.83)，504(10.43)。
The synthesis of (2) 1,7-bis-(4-tertiary butyl phenoxy group)-3,4,9,10-perylene tetracid dianhydrides (shown in formula V a compound):
In 500mL flask, add N, N '-dimethyl methane amide (350mL), under stirring, add compound (8.0g shown in formula IV a, 14.6mmol), 4-TBP (7.16g, 47.7mmol), salt of wormwood (3.73g, 27mmol).Backflow is heated to, reaction 6h under nitrogen protection.Be cooled to room temperature, by mixture impouring 25% acetic acid (450mL), filter the solid of separating out, washing filter cake to filtrate is neutral, dry rear dichloromethane extraction, extraction liquid is concentrated into dry red-purple solid 3.6g (shown in formula V a compound), productive rate 36%.Mp>300℃。
MS(EI
+)m/z(％):689(25.74)，688(80.96)，615(31.31)，329(33.46)，135(100)。
1H NMR(CDCl
3,500MHz)(δ):9.73(d,J＝8.52,2H)，8.66(d,J＝8.53,2H)，8.47(s,2H)，7.60(d,J＝8.85,4H)，7.23(d,J＝8.90,4H)，1.36(s,18H)。
(3) synthesis of target compound (shown in formula II a compound):
In 250mL flask, add compound (3g, 4.36mmol) shown in formula V a, taurine (5.50g, 43.3mmol), ethanol (150mL), under nitrogen protection, be heated to backflow, reaction 8h.Be cooled to room temperature, revolve and steam except desolventizing, residue from dichloromethane/acetone mixed solvent (20:1, v/v) extraction, is concentrated into extraction liquid dry, obtains bright red solid 3.6g (shown in formula II a compound), productive rate 40%.Mp>300℃。
MS(EI
+)m/z(％):903(45)，902(100)，388(41.3)，149(10.4)，125(15.4)。
Compound shown in formula II a is applied in preparation C.I. pigment red 149:
Embodiment 2
The preparation of N, N '-two (3 ', 5 '-3,5-dimethylphenyl) perylene four pyromellitic imide (C.I. pigment red 149)
(1) synthesis of C.I. pigment red 149 crude product:
Jiang perylene acid anhydride (industrial goods, 98%, Liaoning Liangang Pigment and Dyestuff Chemicals Co., Ltd. produces, 400g, 1mol) be dissolved in 10%KOH (6000mL), heating makes it dissolve completely, be cooled to room temperature, add 3, 5-xylidine (industrial goods, 98%, Liaoning Liangang Pigment and Dyestuff Chemicals Co., Ltd. produces, 309g, 2.5mol), add compound shown in 24g formula II a again, after mixing, extremely neutral by the pH value of acetic acid adjustment material, this material is transferred in 10L autoclave pressure, airtight, 180 ~ 200 DEG C are warmed up under stirring, reaction detection is followed the tracks of in sampling, question response Wu Zhong perylene acid anhydride exhausts substantially (reacting about 10 hours), then stopped reaction, cool to room temperature, filter, the micro-siemens of electric conductivity <300 of filtrate washed by filter cake, N is obtained after drying, N '-two (3 ', 5 '-3,5-dimethylphenyl) perylene four pyromellitic imide 593g (C.I. pigment red 149 crude product, yield 95%.
(2) preparation (the pigmenting step of C.I. pigment red 149 crude product) of C.I. pigment red 149 finished product:
Above-mentioned 593g C.I. pigment red 149 crude product is put into ball mill, adds 4500g steel ball, the mixture (2400g, 1:1) of sodium-chlor and sodium sulfate, citric acid (30g) and dimethylbenzene (30g) ball milling 5-6h.After ball milling terminates, material is transferred to 2%HCl (36L, wherein containing PVP and polyoxyethylene oleic acid ester), boil and boil 1-2h, filtered while hot, the micro-siemens of electric conductivity <200 is arrived in washing, through pulverizing and obtain the C.I. pigment red 149 finished product that 540g is gorgeous redness after drying.C.I. pigment red 149 finished product is suitable for the painted of plastics very much, has tinting strength feature that is high and that easily disperse.By the C.I. pigment red 149 finished product prepared by embodiment 1 referred to as C.I. pigment red 149 (A).
C.I. the performance test of pigment red 149 (A):
C.I. pigment red 149 (A) particle ratio surface area instrument (the precise and tiny Gao Bo GHD-030 in Beijing) instrument test, its BET specific surface curve is shown in Fig. 1, obtains specific surface area 95m according to this curve calculation
2/ g.With particle size analyzer (Dandong Bai Te BT-9300S) test, its grain size distribution curve is shown in Fig. 2.
Embodiment 3
The preparation of N, N '-two (3 ', 5 '-3,5-dimethylphenyl) perylene four pyromellitic imide (C.I. pigment red 149)
(1) synthesis of C.I. pigment red 149 crude product:
Jiang perylene acid anhydride (industrial goods, 98%, Liaoning Liangang Pigment and Dyestuff Chemicals Co., Ltd. produces, 400g, 1mol) be dissolved in 10%KOH (6000mL), heating makes it dissolve completely, be cooled to room temperature, add 3, 5-xylidine (industrial goods, 98%, Liaoning Liangang Pigment and Dyestuff Chemicals Co., Ltd. produces, 309g, 2.5mol), add compound shown in 40g formula II a again, after mixing, extremely neutral by the pH value of acetic acid adjustment material, this material is transferred in 10L autoclave pressure, airtight, 180 DEG C ~ 200 DEG C are warmed up under stirring, reaction detection is followed the tracks of in sampling, question response Wu Zhong perylene acid anhydride exhausts substantially (reacting about 10 hours), then stopped reaction, cool to room temperature, filter, the micro-siemens of electric conductivity <300 of filtrate washed by filter cake, N is obtained after drying, N '-two (3 ', 5 '-3,5-dimethylphenyl) perylene four pyromellitic imide 610g (C.I. pigment red 149 crude product), yield 95%.
(2) preparation (the pigmenting step of C.I. pigment red 149 crude product) of C.I. pigment red 149 finished product:
Above-mentioned 610g C.I. pigment red 149 crude product is put into ball mill, adds 4500g steel ball, the mixture (2400g, 1:1) of sodium-chlor and sodium sulfate, citric acid (30g) and dimethylbenzene (30g) ball milling 5-6h.After ball milling terminates, material is transferred to 2%HCl (36L, wherein containing PVP and polyoxyethylene oleic acid ester), boil and boil 1-2h, filtered while hot, the micro-siemens of electric conductivity <200 is arrived in washing, through pulverizing and obtain the C.I. pigment red 149 finished product that 580g is gorgeous redness after drying.C.I. pigment red 149 finished product is suitable for the painted of plastics very much, has tinting strength feature that is high and that easily disperse.By the C.I. pigment red 149 finished product prepared by embodiment 1 referred to as C.I. pigment red 149 (B).
C.I. the performance test of pigment red 149 (B):
C.I. pigment red 149 (B) particle ratio surface area instrument (the precise and tiny Gao Bo GHD-030 in Beijing) instrument test, its BET specific surface curve is shown in Fig. 3, obtains specific surface area 98m according to this curve calculation
2/ g.With particle size analyzer (Dandong Bai Te BT-9300S) test, its grain size distribution curve is shown in Fig. 4.
Comparative example (preparing C.I. pigment red 149 by method described in CN 1563200A)
(1) synthesis of crude pigment product:
Jiang perylene acid anhydride (industrial goods, 98%, Liaoning Liangang Pigment and Dyestuff Chemicals Co., Ltd. produces, 400g, 1mol) be dissolved in 10%KOH (6000mL), heating makes it dissolve completely, be cooled to room temperature, add 3, 5-xylidine (industrial goods, 98%, Liaoning Liangang Pigment and Dyestuff Chemicals Co., Ltd. produces, 309g, 2.5mol), after mixing, regulate material pH to neutral with acetic acid, this material is transferred in 10L autoclave pressure, airtight, 180 DEG C ~ 200 DEG C are warmed up under stirring, reaction detection is followed the tracks of in sampling, question response Wu Zhong perylene acid anhydride exhausts substantially (reacting about 10 hours), then stopped reaction, cool to room temperature, filter, the micro-siemens of electric conductivity <300 of filtrate washed by filter cake, N is obtained after drying, N '-two (3 ', 5 '-3,5-dimethylphenyl) perylene four pyromellitic imide 568g (C.I. pigment red 149 crude product), yield 95%.
(2) preparation (the pigmenting step of C.I. pigment red 149 crude product) of C.I. pigment red 149 finished product:
Above-mentioned 568g C.I. pigment red 149 crude product is put into ball mill, add 4500g steel ball, the mixture (2400g, 1:1) of sodium-chlor and sodium sulfate, citric acid (30g) and dimethylbenzene (30g), the 5-6h of compound ball milling shown in 25g formula a.After ball milling terminates, material is transferred to 2%HCl (36L, wherein containing PVP and polyoxyethylene oleic acid ester), boil and boil 1-2h, filtered while hot, the micro-siemens of electric conductivity <200 is arrived in washing, through pulverizing and obtain the C.I. pigment red 149 (finished product) that 540g takes on a red color after drying.By the C.I. pigment red 149 finished product prepared by comparative example referred to as C.I. pigment red 149 (a).
C.I. the performance test of pigment red 149 (a):
C.I. pigment red 149 (a) granules of pigments ratio surface area instrument (the precise and tiny Gao Bo GHD-030 in Beijing) instrument test, its BET specific surface curve is shown in Fig. 5, obtains specific surface area 78m according to this curve calculation
2/ g.With particle size analyzer (Dandong Bai Te BT-9300S) test, its grain size distribution curve is shown in Fig. 6.
C.I. pigment red 149 (a) also can be used for the painted of plastics, but tinting strength than C.I. pigment red 149 (A) and C.I. pigment red 149 (B) low, and not easily to disperse.
Claims (10)
1. Yi Zhong perylene tetracid diimide derivative, is characterized in that, Suo Shu perylene tetracid diimide derivative is compound shown in formula II, or its salt:
In formula II, R
1~ R
10independently be selected from: hydrogen or C
1~ C
6straight or branched alkyl in a kind of, and R
1~ R
5in have one at least for C
1~ C
6straight or branched alkyl and R
6~ R
10in have one at least for C
1~ C
6straight or branched alkyl; M is the integer of 1 ~ 4; N is the integer of 1 ~ 4.
2., as claim 1 Suo Shu perylene tetracid diimide derivative, it is characterized in that, wherein R
1~ R
10independently be selected from: hydrogen or C
1~ C
4straight or branched alkyl in a kind of, and R
1~ R
5in have one at least for C
1~ C
4straight or branched alkyl and R
6~ R
10in have one at least for C
1~ C
4straight or branched alkyl; M is 1 or 2; N is 1 or 2.
3., as claim 2 Suo Shu perylene tetracid diimide derivative, it is characterized in that, wherein R
1~ R
10independently be selected from: hydrogen or C
4straight or branched alkyl in a kind of, and R
1~ R
5in have one at least for C
4straight or branched alkyl and R
6~ R
10in have one at least for C
4straight or branched alkyl.
4., as claim 3 Suo Shu perylene tetracid diimide derivative, it is characterized in that, wherein R
1~ R
10independently be selected from: hydrogen or C
4straight or branched alkyl in a kind of, and R
1~ R
5in only have one for C
4straight or branched alkyl and R
6~ R
10in only have one for C
4straight or branched alkyl.
5., as claim 4 Suo Shu perylene tetracid diimide derivative, it is characterized in that, wherein R
1~ R
10independently be selected from: a kind of in hydrogen or the tertiary butyl, and R
1~ R
5in only have one for the tertiary butyl and R
6~ R
10in only have one for the tertiary butyl.
6., as claim 5 Suo Shu perylene tetracid diimide derivative, it is characterized in that, wherein at R
1~ R
10in, except R
3and R
8for outside the tertiary butyl, all the other are hydrogen.
7. as the application in any one Suo Shu perylene tetracid diimide derivative Bei perylene pigments in claim 1 ~ 6.
8. apply as claimed in claim 7, it is characterized in that, Qi Zhong Suo Shu perylene pigments is C.I. pigment red 149.
9. apply as claimed in claim 8, it is characterized in that, the method wherein preparing C.I. pigment red 149 comprises the steps:
(1) step of C.I. pigment red 149 crude product is prepared; And
(2) the pigmenting procedure of processing of C.I. pigment red 149 crude product;
And in step (1) implementation process, add any one Suo Shu perylene tetracid diimide derivative in claim 1 ~ 6.
10. apply as claimed in claim 9, it is characterized in that, the method wherein preparing C.I. pigment red 149 comprises the steps:
(perylene acid anhydride is dissolved in the aqueous solution of alkali by 1), heating makes it dissolve completely, be cooled to room temperature, add 3 again, any one Suo Shu perylene tetracid diimide derivative in 5-xylidine and claim 1 ~ 6, after mixing, regulate the pH value of material to neutral, this material is moved in withstand voltage still, airtight, be warmed up to 180 DEG C ~ 200 DEG C under stirring, reaction is followed the tracks of in sampling, and question response Wu Zhong perylene acid anhydride exhausts, then stopped reaction, cool to room temperature, filters, and filter cake obtains C.I. pigment red 149 crude product after washing and drying;
(2) above-mentioned C.I. pigment red 149 crude product is put into ball mill, add steel ball, grinding aid, organic acid and organic solvent, ball milling 3 ~ 6 hours, being poured into by ball milling material in the water medium containing the acidity of tensio-active agent boils boils 1 ~ 2 hour, after filtration, washing and dry C.I. pigment red 149 finished product;
Wherein, in claim 1 ~ 6, the add-on of any one Suo Shu perylene tetracid diimide derivative is the 1wt% ~ 10wt% of C.I. pigment red 149 crude product weight; The add-on of grinding aid is 3 ~ 10 times of C.I. pigment red 149 crude product weight; Organic acid add-on is the 1wt% ~ 10wt% of C.I. pigment red 149 crude product weight; The add-on of organic solvent is the 1wt% ~ 10wt% of C.I. pigment red 149 crude product weight.
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| CN105694531A (en) * | 2016-03-25 | 2016-06-22 | 电子科技大学 | Preparation method of perylene pigment |
| CN110143975A (en) * | 2019-05-20 | 2019-08-20 | 上海大学 | The O of naphthalimide or imide fluorescent label6Benzyl guanine derivative and preparation method thereof |
| CN110591445A (en) * | 2019-10-30 | 2019-12-20 | 辽宁鸿港化工有限公司 | Perylene black pigments suitable for the coloration of aqueous coatings (or inks) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105694531A (en) * | 2016-03-25 | 2016-06-22 | 电子科技大学 | Preparation method of perylene pigment |
| CN110143975A (en) * | 2019-05-20 | 2019-08-20 | 上海大学 | The O of naphthalimide or imide fluorescent label6Benzyl guanine derivative and preparation method thereof |
| CN110143975B (en) * | 2019-05-20 | 2022-06-10 | 上海大学 | Fluorescent-labeled O of naphthalimide or perylene bisimide6-benzylguanine derivatives and process for the preparation thereof |
| CN110591445A (en) * | 2019-10-30 | 2019-12-20 | 辽宁鸿港化工有限公司 | Perylene black pigments suitable for the coloration of aqueous coatings (or inks) |
| CN110591445B (en) * | 2019-10-30 | 2021-12-03 | 辽宁鸿港化工有限公司 | Perylene black pigments suitable for the coloration of aqueous coatings (or inks) |
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| CN104478876B (en) | 2016-08-24 |
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