CN1654546A - Method for preparing black perylene derivatives pigment - Google Patents
Method for preparing black perylene derivatives pigment Download PDFInfo
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- CN1654546A CN1654546A CN 200510023160 CN200510023160A CN1654546A CN 1654546 A CN1654546 A CN 1654546A CN 200510023160 CN200510023160 CN 200510023160 CN 200510023160 A CN200510023160 A CN 200510023160A CN 1654546 A CN1654546 A CN 1654546A
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Abstract
The present invention discloses black perylene pigment preparing process. During the preparation process, 3, 4, 9, 10-perylene tetracid dihydride is first reacted with aryl or substituent aryl aliphatic primary amine in the presence of potassium hydroxide and acetic acid to prepare coarse pigment product; the coarse pigment product is then ball milled in the presence of milling assistant, dispersant, and organic solvent, solid citric acid, maleic acid fumaric acid or calcium stearate; and the and the ball milled material is finally boiled in acid water medium containing surfactant and treated through filtering, water washing and drying to obtain the black perylene pigment. Thus prepared pigment has high black degree, high coloring capacity and easy dispersing.
Description
Technical field
The present invention relates to the preparation method that a kind of Hei Se perylene is (Perylene) pigment.
Background technology
Perylene pigments is a class high performance pigments, and chemical stability that is had and application performance are that common pigments can not be mentioned in the same breath with it.The Da mostly chromatogram of perylene pigments is bright red, purplish red, purplish red and brown, so their Bei Cheng Wei perylene reds again usually.The perylene red 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.
The related De perylene pigments of the present invention is unusual, and its chromatogram is a black, usually Cheng Qi Wei the perylene mineral black, its structure is as follows:
In the formula (1), n=1～3, R is H, CH
3, OH or OCH
3
The chromatogram of Jin Guan perylene mineral black is unusual, but their every application performance is but identical with the crowd.This pigment has very high blackness and tinctorial strength, and remarkable heat-resisting and fastness to weathering can be used as the tinting material of rubber, plastics, printing ink, paint and ink-jet printing ink, also can be used as the toning agent of colour powder of xerographic printing, the black wave filter in the color liquid crystal.With regard to melanochrome, carbon black is the most widely used.It has high tinctorial strength and blackness, remarkable acidproof and fastness to weathering, however the particle of carbon black is tiny soft again, easily causes dust from flying in production and use.In addition, because the resistance of carbon black is lower, so it is difficult to be used to need high-resistance occasion (as the black wave filter in the color liquid crystal).
Shen Yongjia, " kind of pigment dyestuff and application ", 357～375, Chemical Industry Press 2002; H.Zollinger, " Color Chemistry ", VCH Verlagsgessellschaft, 227～228,1991 and U.S. Pat 4,450,273 report the preparation method of perylene mineral black, these methods are each has something to recommend him.But as a complete unit, also has unsatisfactory part.As according to U.S. Pat 4,450,273 report, synthesize De perylene mineral black and can directly use as pigment.But in fact, so the effect of using is unsatisfactory.Say that from application point of view the perylene diimide compounds only was the crude product of pigment, must could use as pigment through the processing of certain pigmenting technology before not through pigmenting processing.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 Organic Pigments " be at Pigment Handbook, Vol.III (New York:John Wiley ﹠amp; Sons, Inc., 1973), the page number: 157, R.B.McKay, " TheDevelopment of Organic Pigments with Particular Reference to Physical Form andConsequent Behavior in Use ", Rev.Prog.Coloration, 10,25-32 (1979), and R.B.McKay, " Control of the application performance of classical organic pigments ", JOCCA, 89-93 (1989).
In the formula (1), n=2, R=H De perylene diimide derivative is registered as C.I. Pigment black 31 in " Colour Index "; And n=1, R=OCH
3De perylene diimide derivative is registered as C.I. Pigment black 32 in " Colour Index ".They are suitable as the black pigment of polyethylene and polyvinyl chloride coloring very much.If be used for transparent polyvinyl chloride coloring, then goods present olive-green.Polystyrene, the thermoplastics of polycarbonate or polyacrylic ester and so on can increase along with the rising of temperature the dissolving power of pigment, is lower than 250 ℃ coloring plastic so 32 of Pigment black 31 and Pigment blacks are suitable for those processing temperatures.Surpass 250 ℃ thermoplastics painted if they are used to processing temperature, just have the part pigment dissolved in wherein.When processing temperature is enough high, the working concentration of Pigment black 31 or Pigment black 32 is enough low again, and at this moment, Pigment black 31 or Pigment black 32 can just all be dissolved in wherein.If transparent plastics, then the coloured light of goods can be changed into orange and intense fluorescence is arranged by black, still has sufficiently high light fastness simultaneously.If the plastic opaque goods, because of it includes white pigment, so present bois de rose.
Pigment black 31 Ke You perylene tetracids or its acid anhydride and phenylethylamine make through reaction.Pigment black 32 Ke You perylene tetracids or its acid anhydride and 4-methoxybenzylamine make through reaction.Reaction can be carried out in water or in the organic solvent, if the former, need be under pressure, if the latter then can react under normal pressure.The synthetic crude product that obtains is according to U.S. Pat 4,450,273 and German patent DE 2832761 can directly use behind its porphyrize.Can re-use after to its pigmenting with traditional method although they also mention, they do not provide concrete pigmenting processing conditions.English Patent GB 1537358 once disclosed and a kind of the black crude product of perylene had been processed into the method for pigment, that is: adopt the means of grinding in solvent (acetone) to realize crude product pigment is carried out the purpose that pigmenting is processed.The shortcoming of this technology is that manufacturing cost is very high, not only needs expensive equipment (so that solvent is reclaimed), and more fatal be that used acetone is low boiling point solvent, highly volatile and inflammable and explosive in air.
Summary of the invention
The object of the invention is, provides a kind of preparation (comprising the synthetic of crude product pigment and pigmenting processing) method of easy and Jing Ji De perylene mineral black, to overcome defective of the prior art.
Suo of the present invention is Shuoed its structure of De perylene mineral black as the formula (1), and the preparation method comprises as follows suddenly:
(1) crude product pigment is synthetic:
In the KOH aqueous solution, add 3,4,9, the 10-perylene tetracid dianhydride, heating is dissolved it fully, be cooled to room temperature and add the Armeen of aryl or substituted aryl replacement again (as phenylethylamine, 4-methoxybenzylamines etc.), both mol ratios Wei perylene tetracid dianhydride: primary amine is 1: 2～5, preferably 1: 2.5～3.5, after stirring, add acetate again, after mixing material is transferred in the autoclave pressure, airtight, be warmed up to 120～190 ℃, preferably 130～150 ℃, insulation reaction, Zhi exhausts substantially Zhi the perylene acid anhydride, cool to room temperature, filter, wash neutrality, obtain the solid (perylene mineral black crude product of black after the drying);
Perhaps above-mentioned being reflected in the organic solvent carried out, temperature of reaction is 120～180 ℃ (preferred 130-150 ℃); Do not need to add KOH and acetate this moment in reaction mixture, need not carry out in autoclave pressure yet.Wherein said organic solvent is that boiling point is higher than 180 ℃ various liquefied compounds, as: dichlorobenzene, trichlorobenzene, Ortho Nitro Toluene, ortho-chlorotolu'ene, parachlorotoluene etc.Or aliphatic compound is as glycerol, ethylene glycol dibutyl ether, dimethyl succinate etc.
(2) pigmenting processing:
To make the black crude product pigment of De perylene by step (1) and adopt the dry type ball milled, in the presence of water miscible grinding aid, dispersion agent, organic solvent and solid-state citric acid, maleic acid, FUMARIC ACID TECH GRADE or calcium stearate, carry out ball milling, after ball milling finishes, the ball milling material poured into to boil in the tart water medium that contains tensio-active agent boil, after filtration, washing, dry De perylene mineral black finished product (target compound);
Wherein: said dispersion agent has structure as the formula (2):
In the formula (2): n=1-2, R=H, CH
3, OH or OCH
3, its add-on is the black crude product pigment weight 0.05%～4% of perylene; The add-on of solid-state citric acid, maleic acid, FUMARIC ACID TECH GRADE or calcium stearate is the black crude product pigment weight 0.5%～5% of perylene.
Embodiment
Suo of the present invention is Shuoed its structure of De perylene mineral black as the formula (1), and the preparation method comprises as follows suddenly:
(1) crude product pigment is synthetic:
In the KOH aqueous solution, add 3,4,9, the 10-perylene tetracid dianhydride, heating is dissolved it fully, is cooled to the Armeen (as phenylethylamine, 4-methoxybenzylamine etc.) that room temperature adds aryl or substituted aryl replacement again, both mol ratio Wei perylene tetracid dianhydrides: primary amine is 1: 2.5～3.5, after stirring, add acetate again, after mixing material is transferred in the autoclave pressure, airtight, be warmed up to 130～150 ℃, insulation reaction, Zhi exhausts substantially Zhi the perylene acid anhydride, cool to room temperature, filter, wash neutrality, obtain the solid (perylene mineral black crude product of black after the drying);
Perhaps above-mentioned being reflected in the organic solvent carried out, temperature of reaction is 130～150 ℃; Said organic solvent is that boiling point is higher than 180 ℃ various liquefied compounds (as: dichlorobenzene, trichlorobenzene, Ortho Nitro Toluene, ortho-chlorotolu'ene or parachlorotoluene etc., or aliphatic compound is as glycerol, ethylene glycol dibutyl ether, dimethyl succinate etc.).
(2) pigmenting processing:
To adopt the dry type ball milled by the crude product pigment of step (1) gained, ball milling is 5～6 hours in the presence of water miscible grinding aid, organic solvent, dispersion agent and solid-state citric acid, maleic acid, FUMARIC ACID TECH GRADE or calcium stearate, 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 mineral black finished product.
Wherein: said water miscible 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 water miscible 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, maleic acid, FUMARIC ACID TECH GRADE or calcium stearate is the black crude product pigment weight 0.5%～5% of perylene; The add-on of dispersion agent is 0.05%～4% of a crude product pigment weight Wei perylene, preferred 0.1%～2%.
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 (but being not limited to): 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, the alkenyl succinic acid monoesters, fatty alcohol-polyoxyethylene ether sulfuric acid succinate monoester, alkylsulphonic acid, lipid acid L-glutamic acid condenses is or/and 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/or 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).Described tensio-active agent is commercially available product.
The pigment finished product that adopts said synthetic method of the present invention and pigmenting working method to be obtained, its blackness height, tinting strength height easily disperse 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, should be understood that but the cited case does not limit protection scope of the present invention by embodiment:
Embodiment 1
N, the preparation of N '-two styroyl perylene tetracid imide (C.I. Pigment black 31)
1) crude product pigment is synthetic:
In 1200g 10%KOH, add 120g (0.3mol) 3,4,9, the 10-perylene tetracid dianhydride, heating is dissolved it fully, is cooled to room temperature and adds 89g (0.75mol) phenylethylamine again, after stirring, add 160g acetate again, after mixing material is transferred in the autoclave pressure, airtight, be warmed up to 130～135 ℃ (about 5 normal atmosphere), insulated and stirred 5h, sampling detects, if reactant Zhong perylene acid anhydride exhausts substantially, then reaction finishes, cool to room temperature filters, and washes neutrality, obtain the solid of 180g black after the drying, be N, N '-two styroyl perylene tetracid imide, yield is near 100%.
2) pigmenting of crude product pigment:
The crude product pigment that exsiccant 60g makes is as stated above put into ball mill, add the 450g steel ball, the mixture of 240g calcium chloride and sodium sulfate (1: 1), 2g citric acid and 8ml dimethylbenzene and butylacetate (1: 1), 1.2g N, N '-two styroyl perylene tetracid imide disulfonic acid, ball milling 5～6h.After ball milling finishes, material transferred among the 2L 2%HCl (contain 1% polyoxyethylene aliphatic alcohol ether and polyoxyethylene oleic acid ester), boil and boil 1～2h, filtered while hot is washed neutrality, and is dry after pulverizing promptly gets the C.I. Pigment black 31 that 58g is black, it has good fastness to solvent, be suitable for very much the various industrial paints of modulation and have good flowability therein, also be applicable to the painted of plastics, good dispersiveness is arranged within it.
Embodiment 2
N, the preparation of N '-two styroyl perylene tetracid imide (C.I. Pigment black 31)
1) crude product pigment is synthetic:
In stainless steel cauldron, add the 800g glycerol, stir adding 120g (0.3mol) 3,4,9 down, 10-perylene tetracid dianhydride and 89g (0.75mol) phenylethylamine is warmed up to 170～175 ℃, insulated and stirred 1h.Sampling detects, if reactant Zhong perylene acid anhydride exhausts substantially, then reaction finishes.Be cooled to 50 ℃, with the dilution of 300g methyl alcohol, methanol wash use in 40 ℃ of filtrations, and water washing then must the 160g black crystals after the drying, i.e. N, N '-two styroyl perylene tetracid imide, productive rate 90%.
2) pigmenting of crude product pigment:
With example 1
Embodiment 3
N, the N '-two (preparation of 4 '-methoxy-benzyl) perylene tetracid imide (C.I. Pigment black 32)
1) crude product pigment is synthetic:
In stainless steel cauldron, add the 1500g glycerol, stir adding 120g (0.3mol) 3,4,9 down, 10-perylene tetracid dianhydride and 102g (0.75mol) 4-methoxybenzylamine is warmed up to 170～175 ℃, insulated and stirred 1h.Sampling detects, if reactant Zhong perylene acid anhydride exhausts substantially, then reaction finishes.Be cooled to 50 ℃, with the dilution of 800g methyl alcohol, methanol wash use in 40 ℃ of filtrations, and water washing then must the 174g black crystals after the drying, i.e. N, N '-two (4 '-methoxy-benzyl) perylene tetracid imide, productive rate 97%.
2) pigmenting of crude product pigment:
To put into ball mill with the crude product pigment that aforesaid method makes through exsiccant 60g, add the 450g steel ball, the mixture of 240g sodium-chlor and sodium sulfate (1: 1), 2g calcium stearate and 1.2gN, N '-two styroyl perylene tetracid imide disulfonic acid, ball milling 5～6h.After ball milling finishes, with vacuum the material sucking-off is transferred among the 3L2%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 black 32 that 58g is black, it is suitable for the various industrial paints of modulation and has good flowability therein very much, also be applicable to the painted of plastics, good dispersiveness is arranged within it.
Embodiment 4
N, the N '-two (preparation of 4 '-methoxy-benzyl) perylene tetracid imide (C.I. Pigment black 32)
1) crude product pigment is synthetic:
In 170g 10%KOH, add 13.5g (0.034mol) 3,4,9, the 10-perylene tetracid dianhydride, heating is dissolved it fully, is cooled to room temperature and adds 12g (0.88mol) 4-methoxybenzylamine again, after stirring, add 23g acetate again, after mixing material is transferred in the autoclave pressure, airtight, be warmed up to 135～140 ℃ (about 5～6 normal atmosphere), insulated and stirred 5h, cool to room temperature filters, and filter cake boils with 600g 2%KOH and boils 1～2h, filtered while hot, hot water wash obtains the solid of 19g black, i.e. N to neutral after the drying, N '-two (4 '-methoxy-benzyl) perylene tetracid imide, yield 95%.
2) pigmenting of crude product pigment:
To put into ball mill with the crude product pigment that aforesaid method makes through exsiccant 50g, add the 450g steel ball, 250g calcium chloride, 2g calcium stearate and 1ml dimethylbenzene, ball milling 2～24h.Ball milling is transferred to 3L 2%HCl (containing 1%PVP and polyoxyethylene oleic acid ester) with vacuum with the material sucking-off after finishing, and boils and boils 1～2h, filtered while hot, wash neutrality, dry after pulverize and promptly get the C.I. Pigment black 32 that 48g is black, it is suitable for the painted of plastics such as PVC very much.
Claims (7)
1, a kind of structure method of pigment as the formula (1) for preparing, it comprises the steps:
(1) crude product pigment is synthetic:
In the KOH aqueous solution, add 3,4,9, the 10-perylene tetracid dianhydride, heating is dissolved it fully, is cooled to the Armeen that room temperature adds aryl or substituted aryl replacement again, both mol ratio Wei perylene tetracid dianhydrides: primary amine is 1: 2～5, after stirring, adds acetate again, after mixing material is transferred in the autoclave pressure, airtight, be warmed up to 120～190 ℃, insulation reaction exhausts substantially Zhi the perylene acid anhydride, and cool to room temperature filters, wash neutrality, dry back De is Dao perylene mineral black crude product;
Or above-mentioned being reflected in the organic solvent carried out, temperature of reaction is 120～180 ℃, wherein said organic solvent is that boiling point is higher than 180 ℃ various liquefied compounds;
(2) pigmenting processing:
To make the black crude product pigment of De perylene by step (1) and adopt the dry type ball milled, in the presence of water miscible grinding aid, dispersion agent, organic solvent and solid-state citric acid, maleic acid, FUMARIC ACID TECH GRADE or calcium stearate, carry out ball milling, after ball milling finishes, the ball milling material poured into to boil in the tart water medium that contains tensio-active agent boil, after filtration, washing, dry target compound;
Wherein: said dispersion agent has structure as the formula (2):
In the formula (2): n=1～2, R=H, CH
3, OH or OCH
3, its add-on Wei perylene mineral black crude product weight 0.05%～4%; The add-on Wei perylene mineral black crude product weight 0.5%～5% of solid-state citric acid, maleic acid, FUMARIC ACID TECH GRADE or calcium stearate.
2, preparation method as claimed in claim 1 is characterized in that, said water miscible grinding aid is that sodium-chlor, sodium sulfate are or/and yellow soda ash in the step (2); Said organic solvent is a dimethylbenzene, sherwood oil, and ethyl acetate, butylacetate, N, N '-dimethyl formamide, propyl carbinol is or/and isopropylcarbinol; 2～5 times and 0.1～0.2 times of the add-on Fen other Wei perylene pigments crude product weight of water miscible grinding aid and organic solvent.
3, preparation method as claimed in claim 1 or 2 is characterized in that, wherein 0.1%～2% of the add-on of dispersion agent Wei perylene pigments crude product weight.
4, preparation method as claimed in claim 3 is characterized in that, wherein tensio-active agent is a negatively charged ion, the tensio-active agent of positively charged ion and/or non-ionic type.
5; preparation method as claimed in claim 4; it is characterized in that; wherein said aniorfic 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; the alkenyl succinic acid monoesters, fatty alcohol-polyoxyethylene ether sulfuric acid succinate monoester, alkylsulphonic acid; lipid acid L-glutamic acid condenses is or/and the alkylsurfuric acid succinate monoester; wherein said lipid acid refers to: palmitinic acid, stearic acid, oleic acid.
6, preparation method as claimed in claim 4 is characterized in that, wherein said cationic surfactant is a quaternary ammonium salt, aliphatic amide alcoxyl hydrochlorate, alcoxyl acid polyamines, aliphatic amine polyoxyethylene ether, aliphatic amide, binary aliphatic amide and/or derive and the polyamine that comes by aliphatic amide and Fatty Alcohol(C12-C14 and C12-C18).
7, preparation method as claimed in claim 4, it is characterized in that, wherein the tensio-active agent of said non-ionic type is an amine oxide, fatty alcohol-polyoxyethylene ether, 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.
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| CN 200510023160 CN1290932C (en) | 2005-01-07 | 2005-01-07 | Method for preparing black perylene derivatives pigment |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102453341A (en) * | 2010-11-02 | 2012-05-16 | 上海华元实业总公司 | Method for preparing vat brilliant red RB |
| CN105694531A (en) * | 2016-03-25 | 2016-06-22 | 电子科技大学 | Preparation method of perylene pigment |
| 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) |
| CN110724104A (en) * | 2019-10-30 | 2020-01-24 | 辽宁鸿港化工有限公司 | 3, 4-perylene diimide derivative and preparation method and application thereof |
| 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 |
| CN113825808A (en) * | 2019-05-15 | 2021-12-21 | M技术株式会社 | Perylene-based black pigment fine particles, method for producing same, black pigment composition containing same, and method for producing perylene-based black pigment fine particles with controlled hue and/or chroma |
| CN114681995A (en) * | 2020-12-25 | 2022-07-01 | 双乐颜料泰兴市有限公司 | Freeze-drying processing technology of pigment |
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2005
- 2005-01-07 CN CN 200510023160 patent/CN1290932C/en not_active Expired - Fee Related
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102453341A (en) * | 2010-11-02 | 2012-05-16 | 上海华元实业总公司 | Method for preparing vat brilliant red RB |
| CN105694531A (en) * | 2016-03-25 | 2016-06-22 | 电子科技大学 | Preparation method of perylene pigment |
| CN113825808A (en) * | 2019-05-15 | 2021-12-21 | M技术株式会社 | Perylene-based black pigment fine particles, method for producing same, black pigment composition containing same, and method for producing perylene-based black pigment fine particles with controlled hue and/or chroma |
| US11834578B2 (en) | 2019-05-15 | 2023-12-05 | M. Technique Co., Ltd. | Black perylene pigment microparticles, method of producing the same, black pigment composition comprising the same, and method of producing black perylene pigment microparticles having controlled hue and/or chroma |
| 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) |
| CN110724104A (en) * | 2019-10-30 | 2020-01-24 | 辽宁鸿港化工有限公司 | 3, 4-perylene diimide derivative and preparation method and application thereof |
| 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) |
| CN110724104B (en) * | 2019-10-30 | 2022-07-05 | 辽宁鸿港化工有限公司 | 3, 4-perylene diimide derivative and preparation method and application thereof |
| CN114681995A (en) * | 2020-12-25 | 2022-07-01 | 双乐颜料泰兴市有限公司 | Freeze-drying processing technology of pigment |
| 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 |
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|---|---|
| CN1290932C (en) | 2006-12-20 |
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