CN1563200A - Fabricating methods of color class for perylene series of pigment - Google Patents
Fabricating methods of color class for perylene series of pigment Download PDFInfo
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Abstract
A porylene pigment product is prepared by applying dried ball-grinding method of ball-grinding solid, organic solvent, dispersing agent, organic solvent and solid organic acid for 5-6 h., pouring ball-ground material in acidic aqueous media containing surface activator for 1-2h hr. boiling and obtaining the perylene pigment through filtering, washing and drying.
Description
Technical field
The present invention relates to the pigmenting working method of Yi Zhong perylene (Perylene) series pigments, belong to field of fine chemical.
Background technology
Perylene pigments is a class high performance pigments, and chemical stability that is had and application performance are that common red pigment can not be mentioned in the same breath with it, and their chromatogram is mainly bright red, purplish red, purplish red and brown, so their Bei Cheng Wei perylene reds again usually.This class pigment has high organic solvent resistance and thermostability, and very high sun-proof and fastness to weathering.Very high anti-migration fastness is arranged in plastics, extraordinary fastness to overvarnishing energy is arranged in paint.
Perylene pigments chemically is being 3,4,9,10-perylene tetracid imide (Jian Cheng perylene diimide) derivative, its structure is as follows:
In the formula, X represents O or N-R, and R represents H, CH
3The perhaps phenyl ring of Qu Daiing, the substituting group on the phenyl ring comprises methyl, methoxyl group, oxyethyl group and azobenzene.The synthetic available known method of this compounds is synthetic, the method that for example following author is disclosed in their works: Shen Yongjia, the kind of pigment dyestuff and application, Chemical Industry Press, 2002, the page number: 357-375.H.Zollinger, " Color Chemistry ", VCHVerlagsgessellschaft, 1991, the page number: 227-228, M.A.Perkins, " Pyridines andPyridones " edits at " The Chemistry of Synthetic Dyes and Pigments " H.A.Lubs, Malabar, Fla, Robert E, Krieger Publishing Company, 1955, the page number: 481-482.
Obtain the De perylene diimide and still can not use by aforesaid method is synthetic, say that from application point of view they only are the crude products of pigment, must pass through the processing of certain pigmenting technology and could use as pigment as pigment.The purpose of pigmenting processing is the size distribution that makes crude product pigment, particle shape, so that crystalline structure changes.Concrete principle can referring to: K.Merkle and H.Schafer, " Surface Treatment of OrganicPigments " be at Pigment Handbook, Vol.III (New York:John Wiley ﹠amp; Sons, Inc., 1973), the page number: 157, 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), and R.B.McKay, " Control of the applicationperformance of classical organic pigments ", JOCCA, 89-93 (1989).
The perylenetetracarboxylic dianhydride is (in the formula 1, X=O) in " Colour Index ", be registered as C.I. Pigment red 224 perylene diimides (in the formula 1, X=NR, R=H) self be used as the existing quite long history of pigment, the many derivatives that are registered as C.I. pigment violet 29 (C.I.71129) perylene diimide in " Colour Index " also can be used as pigment, and by " Colour Index " login, for example, in the formula 1, X=NR, the R=phenyl ring has oxyethyl group to replace De perylene diimide derivative again on the phenyl ring, be registered as the C.I. pigment red 123 in " Colour Index ".Being authorized by State Intellectual Property Office about the technology of preparing of C.I. pigment red 149 and 179 is patent of invention (seeing ZL01105357.7).
German patent DE 1619531 discloses and a kind of perylene diimide has been processed into the method for pigment, that is, adopt the means of grinding in solvent to realize the purpose that crude product pigment is processed.The shortcoming of this technology is that manufacturing cost is very high, not only needs expensive equipment, also needs solvent is reclaimed.German patent DE 2043820 discloses and a kind of perylene diimide has been processed into the method for pigment, promptly adopt at alkaline water medium confrontation crude product pigment and grind, but its quality of product of using such technology to obtain can not satisfy current user's requirement.German patent DE 2316536 discloses a kind of technology of two-step approach, and promptly Xian Dui perylene diimide crude product pigment adopts dry grinding, carries out the acid method that expands again and handle in sulfuric acid.Because need to add amine (or amides) compound when grinding, this causes prepared product not match in some applicating medium, thereby is not widely adopted.German patent DE 2851752 discloses a kind of technology of multistep processes Dui perylene diimide crude product pigment processing, at first carries out dry grinding in the presence of small amount of acid, then uses solvent recrystallization.In acid, grind the grinding plant that means that the needs use is made by exotic materials, moreover in the operation of reality, operative employee's human and environment can't can be polluted with avoiding.European patent EP 39912 discloses the method that a kind of Dui perylene diimide crude product pigment carries out pigmenting, in their method, to add a kind of halo De perylene diimide, one reinstate the vitriol oil to carry out acid molten then, carry out dry grinding subsequently again, carry out solvent treatment at last again.This method is very time-consuming, can produce a large amount of sulfur waste acid again simultaneously, and is unfavorable to environmental protection.European patent EP 366062 also discloses a kind of method that needs interpolation Lu Dai perylene diimide Bing Dui perylene diimide crude product pigment to carry out pigmenting, and problem is that the manufacturing of this halo De perylene diimide itself is just very complicated.German patent DE 4007728 disclose a kind of Zhong organic solvent Dui perylene diimide crude product pigment carry out the method for pigmenting.This also is a kind of technology of two-step approach, and used organic solvent is a carboxylicesters, and it will and discard it through saponification after completion of processing.European patent EP 678559 discloses another kind of two-step approach perylene diimide crude product pigment has been carried out the method for pigmenting,, carries out dry grinding earlier that is, carries out wet grinding again.The production cycle of above-mentioned these two kinds of technologies is all very long, so manufacturing cost is all very high.Chinese patent (ZL 01105357.7) discloses a kind of method of dry ball milling, in ball milling, add symmetric on a small quantity, water-insoluble at perylene tetracid diimide derivative as pigment dispersing agent.But the pigment that so makes mobile undesirable in being coated with material products still has room for improvement.
Summary of the invention
The objective of the invention is to, disclose a kind of pigmenting working method of easy and Jing Ji De perylene pigments, to overcome defective of the prior art.
Technical scheme of the present invention:
It is as follows that Suo of the present invention is Shuoed the key step of pigmenting working method of De perylene pigments:
The crude product (its method that is disclosed in preparing by the works of aforementioned author at them is carried out) of perylene pigments is adopted the dry type ball milled, carry out ball milling having in the presence of grinding aid, dispersion agent and the organic solvent, after ball milling finishes, the ball milling material poured in the tart water medium that contains tensio-active agent carry out aftertreatment, washing after filtration,, dry De perylene pigments finished product, it is characterized in that said dispersion agent has structure as the formula (1):
In the formula: X=N-R, R=phenyl or substituted-phenyl, said substituted-phenyl is preferred: have one or more sulfonic groups on the phenyl; Add solid-state citric acid, Succinic Acid, sodium acetate or calcium stearate when ball milling, its add-on is a crude product pigment weight 0.5%～5% Wei perylene.
The said pigmenting working method of the present invention is suitable for Suo You De perylene pigments, and what right effect was best is to have following Jie Gou De perylene pigments:
In the formula: X represents O or N-R, and R represents H, CH
3The perhaps phenyl ring of Qu Daiing, the substituting group on the phenyl ring comprises methyl, methoxyl group, oxyethyl group and/or azobenzene.
Embodiment
It is that: adopts the dry type ball milled Jiang the perylene pigments crude product that Suo of the present invention is Shuoed the key step of pigmenting working method of perylene pigments, ball milling there are being in the presence of grinding aid, organic solvent, dispersion agent and solid-state citric acid, Succinic Acid, sodium acetate or the calcium stearate 5～6 hours, after ball milling finishes, the ball milling material poured into to boil in the tart water medium that contains tensio-active agent boil 1～2 hour, after filtration, washing, dry De perylene pigments finished product.
Wherein: said grinding aid is that sodium-chlor, sodium sulfate are or/and yellow soda ash; Said organic solvent is a dimethylbenzene, sherwood oil, and ethyl acetate, butylacetate, N, N '-dimethyl formamide (DMF), propyl carbinol is or/and isopropylcarbinol; The add-on Fen other of grinding aid and organic solvent is 2～5 times and 0.1～0.2 times of crude product pigment weight Wei perylene; The add-on of solid-state citric acid, Succinic Acid, sodium acetate or calcium stearate is a crude product pigment weight 0.5%～5% Wei perylene; The add-on of dispersion agent is 1%～5% of a crude product pigment weight Wei perylene, preferred 2%～3%.
Said tensio-active agent is a negatively charged ion, the tensio-active agent of positively charged ion and/or nonionic type.
Suitable anion 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 Soxylat A 25-7, the dialkyl succinylsuccinate monoamide, alkenyl succinic acid monoesters, fatty alcohol-polyoxyethylene ether sulfuric acid succinate monoester, alkylsulphonic acid, lipid acid L-glutamic acid condenses, the alkylsurfuric acid succinate monoester, wherein said lipid acid refers to: palmitinic acid, stearic acid, oleic acid;
The suitable cationic surfactants kind mainly is a quaternary ammonium salt, aliphatic amide alcoxyl hydrochlorate, alcoxyl acid polyamines, aliphatic amine polyoxyethylene ether, aliphatic amide, binary aliphatic amide and derived and the polyamine that comes by aliphatic amide and Fatty Alcohol(C12-C14 and C12-C18);
Suitable nonionogenic tenside kind mainly contains amine oxide, fatty alcohol-polyoxyethylene ether, the aliphatic alcohol polyethenoxy ester, trimethyl-glycine (as fatty acid amide-N-CAB), the 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 pigment finished product that adopts the said pigmenting working method of the present invention to be obtained, its coloured light is bright-coloured, tinting strength is high, easily disperses in applicating medium.In addition, the present invention also has convenient and easy and advantage such as process cost is cheap.
Below will do detailed explanation to the present invention, but the cited case does not limit protection scope of the present invention by embodiment:
Embodiment 1
The preparation of perylene tetracid imide (C.I. pigment violet 29)
1) crude product pigment is synthetic:
In the stainless steel pressure still, add 6000ml water, 600g 3,4,9,10-perylene tetracid dianhydride and 360g 25% ammoniacal liquor, after stirring, be warmed up to 150 ℃ under airtight, insulated and stirred 5h, reaction steams excess of ammonia water after finishing, cool to room temperature, filter, wash neutrality, dry back De is Dao perylene tetracid imide 590g.
2) pigmenting of crude product pigment:
To put into ball mill through exsiccant 568g perylene tetracid imide, add the 4500g steel ball, the mixture of 2400g sodium-chlor and sodium sulfate (1: 1), 15g citric acid and 50ml dimethylbenzene and butylacetate (1: 1), 12g N, N '-two (3 '-sulphenyl) perylene tetracid imide, ball milling 5-6h.After ball milling finishes, material transferred among the 34L 2%HCl (contain 1% polyoxyethylene aliphatic alcohol ether and polyoxyethylene oleic acid ester), boil and boil 1-2h, filtered while hot, wash neutrality, drying is purpureal C.I. pigment violet 29 after pulverizing promptly gets 540g, and it is suitable for the various industrial paints of modulation and has good flowability therein very much.
Embodiment 2
The preparation of perylene tetracid imide (C.I. pigment violet 29)
1) crude product pigment is synthetic:
In the stainless steel pressure still, add 500kg 5% ammoniacal liquor, 50kg 3,4,9, the 10-perylene tetracid dianhydride, after stirring, pressurization is warmed up to 150 ℃, insulated and stirred 5h.Reaction steams excess of ammonia water after finishing, and cool to room temperature filters, and washes neutrality, and dry back De is Dao perylene tetracid imide 49kg.
2) pigmenting of crude product pigment:
To put into ball mill through exsiccant 5kg perylene tetracid imide, add the 40kg steel ball, the mixture of 20kg sodium-chlor and sodium sulfate (1: 1), 150g Succinic Acid and 500ml dimethylbenzene and butylacetate (1: 1), 100g N, N '-two (3 '-sulphenyl) perylene tetracid imide, ball milling 5h.After ball milling finishes, with vacuum the material sucking-off is transferred among the 300kg 2%HCl and (to be contained 1% polyoxyethylene aliphatic alcohol ether and polyoxyethylene oleic acid ester), boil and boil 2h, filtered while hot, wash neutrality, drying is purpureal C.I. pigment violet 29 after pulverizing promptly gets 4.5kg, and it is suitable for the various industrial paints of modulation and has good flowability therein very much.
Embodiment 3
N, the N '-two (preparation of 4 '-ethoxyl phenenyl) perylene tetracid imide (C.I. pigment red 123)
1) crude product pigment is synthetic:
(1mol) perylene acid anhydride is dissolved in the solution of 6000mL 10%KOH with 392g, heating is dissolved it fully, be cooled to room temperature, add 392g (2.86mol) 4-phenetidine, add 2mol acetate again, after mixing material is transferred in the 10L autoclave pressure, airtight, be warmed up to 180 ℃, insulation reaction 10h under stirring, sampling detects, if reactant Zhong perylene acid anhydride exhausts substantially, stopped reaction then, cool to room temperature, reaction product is taken out, remove by filter moisture, wash neutrality, get N after the drying, N '-two (4 '-ethoxyl phenenyl) perylene tetracid imide 600g (0.95mol), yield 95%.
2) pigmenting of crude product pigment:
Will be through exsiccant 600g N, (4 '-ethoxyl phenenyl) perylene tetracid imide is put into ball mill to N '-two, add the 4500g steel ball, the mixture of 2400g sodium-chlor and sodium sulfate (1: 1), 20g calcium stearate and 15gN, N '-two (4 '-sulphenyl) perylene tetracid imide, ball milling 5-6h.After ball milling finishes, with vacuum the material sucking-off is transferred among the 36L 2%HCL and (to be contained 1%PVP and polyoxyethylene oleic acid ester), boil and boil 1-2h, filtered while hot, wash neutrality, dry after pulverizing promptly gets the C.I. pigment red 123 that 540g is gorgeous large red, it is suitable for the various industrial paints of modulation and has good flowability therein very much.
Embodiment 4
N, the N '-two (preparation of 4 '-ethoxyl phenenyl) perylene tetracid imide (C.I. pigment red 123)
1) crude product pigment is synthetic:
(153mol) perylene acid anhydride is dissolved in the solution of 600kg 10%KOH, and heating is dissolved it fully, is cooled to room temperature with 60kg, add 60kg (437mol) 4-phenetidine, add 80kg acetate again, after mixing material is transferred in the autoclave pressure, airtight, be warmed up to 180 ℃, insulation reaction 10h under stirring, sampling detects, if reactant Zhong perylene acid anhydride exhausts substantially, stopped reaction then, cool to room temperature, filter, wash neutrality.Add water 2500kg, solid potassium hydroxide 50kg again, vat powder (V-Brite B) 50kg is warmed up to 85 ℃, insulation 1h, in 1h, add 10% clorox 110kg again, finish, insulated and stirred 6 hours, behind the cool to room temperature, filter, wash neutrality, get N after the drying, N '-two (4 '-ethoxyl phenenyl) perylene tetracid imide 87kg (138mol), yield 90%.
2) pigmenting of crude product pigment:
Will be through exsiccant 60kg N, (4 '-ethoxyl phenenyl) perylene tetracid imide is put into ball mill to N '-two, add the 450kg steel ball, the mixture of 240kg sodium-chlor and sodium sulfate (1: 1), 2kg calcium stearate and 1.2kgN, N '-two (4 '-sulphenyl) perylene tetracid imide, ball milling 5-6h.After ball milling finishes, with vacuum the material sucking-off is transferred among the 360L 2%HCL and (to be contained 1%PVP and polyoxyethylene oleic acid ester), boil and boil 1-2h, filtered while hot, wash neutrality, dry it is very loose after pulverizing promptly gets the C.I. pigment red 123 that 54kg is gorgeous large red, is suitable for very much the various industrial paints of modulation and has good flowability therein.
Embodiment 5
The preparation of perylene tetracid dianhydride (C.I. Pigment red 224)
Making with extra care of 1) Cu Pin perylene acid anhydride:
(412g 1mol) mixes with 3200mL sulfuric acid, is warmed up to 50 ℃, insulated and stirred 6h with 95% purity De perylene acid anhydride, cool to room temperature, thin up is about 10% to vitriolic concentration, filters, wash neutrality, get 98% purity De perylene acid anhydride 396g (0.9mol), yield 99% after the drying.
The pigmenting of 2) perylene acid anhydrides:
Exsiccant 396g perylene acid anhydride is put into ball mill, add 3300g steel ball and 1230g sodium-chlor, add 30g Succinic Acid and 8g N again, N '-two (2 ', 5 '-disulfonic acid phenyl) perylene tetracid imide, ball milling 3h.After ball milling finishes, with vacuum the material sucking-off is transferred among the 8000ml 2%HCL and (to be contained 1%PV and alkylphenol polyoxyethylene ether), boil and boil 1-2h, filtered while hot, wash neutrality, dry after pulverizing promptly gets the C.I. Pigment red 224 of 368g large red, be suitable for very much original finish paint of automobile and retouching paint.
Embodiment 6
The preparation of perylene tetracid dianhydride (C.I. Pigment red 224)
Making with extra care of 1) Cu Pin perylene acid anhydride:
(65kg 153mol) mixes with 600kg 10%KOH, and stirring heats up down makes its dissolving, filters with 92% purity De perylene acid anhydride, filtrate is transferred PH=2-3 with the vitriol oil, stirs 6h, filters under the room temperature, wash neutrality, get 98% purity De perylene acid anhydride 55kg (145mol), yield 90% after the drying.
The pigmenting of 2) perylene acid anhydrides:
Exsiccant 10kg perylene tetracid dianhydride is put into ball mill, add 100kg steel ball and 30kg sodium-chlor, add the 300g Succinic Acid again, 250g N, N '-two (2 ', 5 '-disulfonic acid phenyl) perylene tetracid imide, ball milling 3h.After ball milling finishes, with vacuum the material sucking-off is transferred among the 200kg 2%HCl and (to be contained 1%PV and alkylphenol polyoxyethylene ether), boil and boil 1-2h, filtered while hot, wash neutrality, dry after pulverizing promptly gets the C.I. Pigment red 224 of 9.5kg large red, be suitable for very much original finish paint of automobile and retouching paint.
Claims (6)
1, Qi crude product Jiang perylene pigments of pigmenting working method of Yi Zhong perylene pigments adopts the dry type ball milled, carry out ball milling having in the presence of grinding aid, dispersion agent and the organic solvent, after ball milling finishes, the ball milling material poured in the tart water medium that contains tensio-active agent carry out aftertreatment, after filtration, washing, dry De perylene pigments finished product, it is characterized in that said dispersion agent has structure as the formula (1):
In the formula: X=N-R, R=phenyl or substituted-phenyl; Add solid-state citric acid, Succinic Acid, sodium acetate or calcium stearate when ball milling, its add-on is a crude product pigment weight 0.5%～5% Wei perylene.
2, pigmenting working method as claimed in claim 1 is characterized in that, wherein R is the phenyl that sulfonic group replaces.
3, pigmenting working method as claimed in claim 1 or 2 is characterized in that, wherein Suo is Shuoed the structure of De perylene pigments and is shown below:
In the formula: X represents O or N-R, and R represents H, CH
3The perhaps phenyl ring of Qu Daiing, the substituting group on the phenyl ring comprises methyl, methoxyl group, oxyethyl group and/or azobenzene.
4, pigmenting working method as claimed in claim 3, it is characterized in that, the key step of described pigmenting working method is that: adopts the dry type ball milled Jiang the perylene pigments crude product, ball milling there are being in the presence of grinding aid, organic solvent, dispersion agent and solid-state citric acid, Succinic Acid, sodium acetate or the calcium stearate 5～6 hours, after ball milling finishes, the ball milling material poured into to boil in the tart water medium that contains tensio-active agent boil 1～2 hour, after filtration, washing, dry De perylene pigments finished product;
Wherein: said grinding aid is that sodium-chlor, sodium sulfate are or/and yellow soda ash; Said organic solvent is a dimethylbenzene, sherwood oil, and ethyl acetate, butylacetate, N, N '-dimethyl formamide, propyl carbinol is or/and isopropylcarbinol; The add-on Fen other of grinding aid and organic solvent is 2～5 times and 0.1～0.2 times of crude product pigment weight Wei perylene; The add-on of said dispersion agent is 1%～5% of a crude product pigment weight Wei perylene; The add-on of said solid-state citric acid, Succinic Acid, sodium acetate or calcium stearate is a crude product pigment weight 0.5%～5% Wei perylene; Said tensio-active agent is a negatively charged ion, the tensio-active agent of positively charged ion and/or nonionic type.
5, pigmenting working method as claimed in claim 4, it is characterized in that, wherein said anion surfactant is: 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 Soxylat A 25-7, the dialkyl succinylsuccinate monoamide, alkenyl succinic acid monoesters, fatty alcohol-polyoxyethylene ether sulfuric acid succinate monoester, alkylsulphonic acid, lipid acid L-glutamic acid condenses, the alkylsurfuric acid succinate monoester, wherein said lipid acid refers to: palmitinic acid, stearic acid, oleic acid;
Said cats product is: quaternary ammonium salt, aliphatic amide alcoxyl hydrochlorate, alcoxyl acid polyamines, aliphatic amine polyoxyethylene ether, aliphatic amide, binary aliphatic amide and derived and the polyamine that comes by aliphatic amide and Fatty Alcohol(C12-C14 and C12-C18);
Said nonionogenic tenside is: amine oxide, fatty alcohol-polyoxyethylene ether, the aliphatic alcohol polyethenoxy ester, trimethyl-glycine, the 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.
6, pigmenting working method as claimed in claim 5 is characterized in that, wherein the add-on of said dispersion agent is 2%～3% of a crude product pigment weight Wei perylene.
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| CN 200410017719 CN1229443C (en) | 2004-04-16 | 2004-04-16 | Fabricating methods of color class for perylene series of pigment |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1303159C (en) * | 2005-02-24 | 2007-03-07 | 天津理工大学 | Method for preparing perylene pigments with high hiding power |
| CN1303160C (en) * | 2005-02-24 | 2007-03-07 | 天津理工大学 | Process for catalytic preparation of perylenes pigment crudes by fatty alcohols in water intermediate |
| CN104478876A (en) * | 2014-11-25 | 2015-04-01 | 辽宁鸿港化工有限公司 | N,N'-dimethyl-3,4,9,10-perylenetetracarboxylic diimide derivative and application thereof |
| CN106084884A (en) * | 2016-06-12 | 2016-11-09 | 南通市争妍颜料化工有限公司 | Pigment red 3 BL pigmentation processes technique |
| CN108690365A (en) * | 2018-06-16 | 2018-10-23 | 山东宇虹新颜料股份有限公司 | A kind of preparation method of the pigment Yellow 14 of easy filtration drying |
| CN113122019A (en) * | 2021-04-23 | 2021-07-16 | 辽宁鸿港化工有限公司 | Method for performing pigmenting processing on perylene pigment by chemical method |
| CN113249984A (en) * | 2021-07-02 | 2021-08-13 | 浙江理工大学 | Deep eutectic solvent and high-energy ball milling technology-based red and yellow natural dye color matching dyeing method |
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2004
- 2004-04-16 CN CN 200410017719 patent/CN1229443C/en not_active Expired - Fee Related
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1303159C (en) * | 2005-02-24 | 2007-03-07 | 天津理工大学 | Method for preparing perylene pigments with high hiding power |
| CN1303160C (en) * | 2005-02-24 | 2007-03-07 | 天津理工大学 | Process for catalytic preparation of perylenes pigment crudes by fatty alcohols in water intermediate |
| CN104478876A (en) * | 2014-11-25 | 2015-04-01 | 辽宁鸿港化工有限公司 | N,N'-dimethyl-3,4,9,10-perylenetetracarboxylic diimide derivative and application thereof |
| CN106084884A (en) * | 2016-06-12 | 2016-11-09 | 南通市争妍颜料化工有限公司 | Pigment red 3 BL pigmentation processes technique |
| CN108690365A (en) * | 2018-06-16 | 2018-10-23 | 山东宇虹新颜料股份有限公司 | A kind of preparation method of the pigment Yellow 14 of easy filtration drying |
| CN108690365B (en) * | 2018-06-16 | 2020-03-20 | 山东宇虹新颜料股份有限公司 | Preparation method of easily-filtered and dried pigment yellow 14 |
| CN113122019A (en) * | 2021-04-23 | 2021-07-16 | 辽宁鸿港化工有限公司 | Method for performing pigmenting processing on perylene pigment by chemical method |
| CN113122019B (en) * | 2021-04-23 | 2022-09-09 | 辽宁鸿港化工有限公司 | Method for performing pigmenting processing on perylene pigment by chemical method |
| CN113249984A (en) * | 2021-07-02 | 2021-08-13 | 浙江理工大学 | Deep eutectic solvent and high-energy ball milling technology-based red and yellow natural dye color matching dyeing method |
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| Publication number | Publication date |
|---|---|
| CN1229443C (en) | 2005-11-30 |
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