CN113652097A - Active disperse dye and preparation method thereof - Google Patents
Active disperse dye and preparation method thereof Download PDFInfo
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- CN113652097A CN113652097A CN202110919212.XA CN202110919212A CN113652097A CN 113652097 A CN113652097 A CN 113652097A CN 202110919212 A CN202110919212 A CN 202110919212A CN 113652097 A CN113652097 A CN 113652097A
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- disperse dye
- oil
- added
- reactive disperse
- macromolecular
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- 239000000986 disperse dye Substances 0.000 title claims abstract description 57
- 238000002360 preparation method Methods 0.000 title claims abstract description 27
- 239000003086 colorant Substances 0.000 claims abstract description 59
- 239000003921 oil Substances 0.000 claims abstract description 53
- 235000019198 oils Nutrition 0.000 claims abstract description 52
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 45
- 150000001412 amines Chemical class 0.000 claims abstract description 13
- 239000000126 substance Substances 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 8
- 235000015112 vegetable and seed oil Nutrition 0.000 claims abstract description 8
- 239000010775 animal oil Substances 0.000 claims abstract description 7
- 239000008158 vegetable oil Substances 0.000 claims abstract description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- -1 aniline compound Chemical class 0.000 claims description 40
- 238000006243 chemical reaction Methods 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 17
- 239000004519 grease Substances 0.000 claims description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 14
- 150000003141 primary amines Chemical group 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 12
- 238000002156 mixing Methods 0.000 claims description 11
- 150000004982 aromatic amines Chemical class 0.000 claims description 10
- 239000011230 binding agent Substances 0.000 claims description 10
- 150000008049 diazo compounds Chemical class 0.000 claims description 10
- 229920000768 polyamine Polymers 0.000 claims description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- 238000006482 condensation reaction Methods 0.000 claims description 9
- 239000003925 fat Substances 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 238000005859 coupling reaction Methods 0.000 claims description 8
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- 229920002545 silicone oil Polymers 0.000 claims description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 8
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 7
- 150000004985 diamines Chemical class 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 6
- 235000019197 fats Nutrition 0.000 claims description 6
- TUFJPPAQOXUHRI-KTKRTIGZSA-N n'-[(z)-octadec-9-enyl]propane-1,3-diamine Chemical compound CCCCCCCC\C=C/CCCCCCCCNCCCN TUFJPPAQOXUHRI-KTKRTIGZSA-N 0.000 claims description 6
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 claims description 6
- 235000010288 sodium nitrite Nutrition 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 230000008901 benefit Effects 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- 238000004537 pulping Methods 0.000 claims description 4
- 235000019871 vegetable fat Nutrition 0.000 claims description 4
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 claims description 3
- 239000004698 Polyethylene Substances 0.000 claims description 3
- 229920002873 Polyethylenimine Polymers 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- 229920000573 polyethylene Polymers 0.000 claims description 3
- YMZIFDLWYUSZCC-UHFFFAOYSA-N 2,6-dibromo-4-nitroaniline Chemical compound NC1=C(Br)C=C([N+]([O-])=O)C=C1Br YMZIFDLWYUSZCC-UHFFFAOYSA-N 0.000 claims description 2
- MGCGMYPNXAFGFA-UHFFFAOYSA-N 2-amino-5-nitrobenzonitrile Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C#N MGCGMYPNXAFGFA-UHFFFAOYSA-N 0.000 claims description 2
- LDTCWISGJYTXDC-UHFFFAOYSA-N 5-nitro-1,2-benzothiazol-3-amine Chemical compound C1=C([N+]([O-])=O)C=C2C(N)=NSC2=C1 LDTCWISGJYTXDC-UHFFFAOYSA-N 0.000 claims description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- LZGUHMNOBNWABZ-UHFFFAOYSA-N n-nitro-n-phenylnitramide Chemical compound [O-][N+](=O)N([N+]([O-])=O)C1=CC=CC=C1 LZGUHMNOBNWABZ-UHFFFAOYSA-N 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000010792 warming Methods 0.000 claims 3
- 239000000975 dye Substances 0.000 abstract description 25
- 239000001993 wax Substances 0.000 abstract description 7
- 230000006872 improvement Effects 0.000 abstract description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000010703 silicon Substances 0.000 abstract 1
- 229910052710 silicon Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 description 31
- 239000000047 product Substances 0.000 description 12
- 238000001816 cooling Methods 0.000 description 9
- 238000004040 coloring Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 235000014593 oils and fats Nutrition 0.000 description 8
- 239000000985 reactive dye Substances 0.000 description 8
- 238000001914 filtration Methods 0.000 description 6
- 239000012467 final product Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229920002521 macromolecule Polymers 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 210000003739 neck Anatomy 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 230000008092 positive effect Effects 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- CUDYYMUUJHLCGZ-UHFFFAOYSA-N 2-(2-methoxypropoxy)propan-1-ol Chemical compound COC(C)COC(C)CO CUDYYMUUJHLCGZ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 229940008099 dimethicone Drugs 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229940119170 jojoba wax Drugs 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000992 solvent dye Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
- C09B29/0011—Monoazo dyes prepared by diazotising and coupling from diazotized anilines from diazotized anilines directly substituted by a heterocyclic ring (not condensed)
-
- 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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/008—Preparations of disperse dyes or solvent dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The invention discloses an active disperse dye and a preparation method thereof, belonging to the field of high-molecular dyes. The reactive disperse dye has a chemical structure shown in formula II: formula II
Wherein R is1Selected from H, Cl, NO2，CH3Or is absent; r2Selected from H, Cl, NO2，CH3Or absent, CN; r3＝H，Cl，NO2，CH3CN or absent; r4Selected from H, Cl, CH3Or is absent; r5Selected from H, Cl, CH3Or a benzene ring attached to the position and its ortho-position. The invention designs reactive groups, utilizes a reactive disperse dye structure and connects through aminoTo the fatty amine component. By the chemical improvement method, the coloring agent can be natural oil, wax, silicon oil, synthetic oil, animal and vegetable oil. The miscibility of the colors is good.
Description
Technical Field
The invention belongs to the field of high molecular dyes, and particularly relates to a reactive disperse dye and a preparation method thereof.
Background
Reactive dyes, disperse dyes, and the like are generally capable of providing desirable coloration to various materials, such as cotton, polyester, and the like. However, these dyes have no coloring effect on insoluble substances. For example, reactive and disperse dyes do not color fuels, oils or waxes because they do not have any solubility in these media. Only solvent dyes are available on the market today for coloring these media, however, these dyes also have certain solubility problems, even for products such as silicone oils, etc.
At present, a plurality of dyes exist in the prior art, but the solubility of the colorant obtained based on the modification of the dyes in oil is not good due to the poor oil solubility of the dyes.
Disclosure of Invention
Based on the defects in the field, the invention aims to provide a preparation method of a macromolecular coloring agent for oil, the macromolecular coloring agent is suitable for coloring natural oil, wax, silicone oil, synthetic oil and animal and vegetable oil, and has high solubility and complete chromatogram.
The technical scheme of the invention is as follows:
a reactive disperse dye, characterized by having a chemical structure represented by formula II:
formula II
Wherein R is1Selected from H, Cl, NO2，CH3Or is absent; r2Selected from H, Cl, NO2，CH3Or absent, CN; r3＝H，Cl，NO2，CH3CN or absent; r4Selected from H, Cl, CH3Or is absent; r5Selected from H, Cl, CH3Or a benzene ring attached to the position and its ortho-position.
The reactive disperse dye is selected from the following structures:
formula IV
Or the like, or, alternatively,
formula III
The preparation method of the reactive disperse dye comprises the following steps: diazo compound is added into aromatic amine for coupling reaction, and cyanuric chloride is added for condensation reaction.
Adding water to the aromatic amine before adding the diazo compound;
the dosage ratio of the aromatic amine to the water is 9-14: 10;
preferably, the diazo compound is slowly dripped into the mixed solution of the aromatic amine and the water, and the slow dripping time is preferably 30 minutes;
more preferably, the slow dropwise addition is carried out at low temperature; the low temperature is preferably 5 ℃; preferably, the time of the coupling reaction is between 3 and 8h, preferably 5 h;
preferably, the condensation reaction time is 1-3h, preferably 3h, and the pH value is 3-4;
preferably, both the coupling reaction and the condensation reaction are carried out at low temperatures; the low temperature is preferably 5 ℃;
the dosage proportion of the aromatic amine, the diazo compound and the cyanuric chloride is as follows: the mass ratio is 9-14: 18;
the preparation method further comprises the following steps: the pH of the product obtained by the condensation reaction is adjusted to be neutral, and then the product is filtered and washed by water.
The diazo compound is diazo liquid;
preferably, the diazo liquid is prepared by the following method:
adding strong acid and water into the aniline compound, uniformly mixing, adding sodium nitrite, standing, and finally adding sulfamic acid;
the aniline compound is selected from: aniline, p-nitroaniline, optionally 2-4, dinitroaniline, o-cyano-p-nitroaniline, 2, 6-dibromo-4-nitroaniline, 3-amino-5-nitrobenzoisothiazole;
preferably, the strong acid is selected from: hydrochloric acid, sulfuric acid;
preferably, the dosage ratio of the aniline compound, the strong acid, the water, the sodium nitrite and the sulfamic acid is 1-15: 3-30: 0.5-2: 2, preferably 9-14: 30: 7.5: 2;
the advantage of using the above-mentioned ratio of amounts is that the reaction is fully completed.
Preferably, the mixing refers to pulping for 1 h;
preferably, the temperature is reduced to 0 ℃ after uniform mixing;
preferably, the standing refers to standing at 0 ℃ for 1 h;
the reactive disperse dye and/or the reactive disperse dye prepared by the preparation method are used for preparing a colorant.
Adding a solvent into the active disperse dye, uniformly mixing, adding fatty amine, and heating;
preferably, the solvent is selected from white oil, cyclopentadidimethyl siloxane, vegetable oil and fat, animal oil and fat, and dimethyl silicone oil;
the white oil is preferably No. 26 white oil;
preferably, the fatty amine is selected from primary amines, diamines or polyamines;
the primary amine is preferably cocoalkyl primary amine, tetradecyl primary amine, or oleyl primary amine;
the diamine is preferably N-oleyl-1, 3-propylenediamine, N-coco-1, 3-propylenediamine;
the polyamine is selected from: polyethylene polyamine, polyethylene imine.
Preferably, an acid-binding agent is added into the reactive disperse dye before the solvent is added;
the acid-binding agent is preferably sodium carbonate, potassium carbonate or potassium hydroxide;
preferably, the colorant refers to a macromolecular colorant for grease.
The heating refers to heating to 40-60 ℃, preferably 40 ℃, reacting for 2-3h, preferably 3h, and then heating to 80-100 ℃, preferably 90 ℃, reacting for 2-3 h; or heating to 80-100 deg.C, preferably 80 deg.C, under nitrogen protection, and reacting for 3-6h, preferably 6 h;
preferably, the mixing means to mix by stirring at 100-.
Preferably, after the temperature is raised to 80-100 ℃, preferably 80 ℃, and the reaction is carried out for 3-6h, preferably 6h under the protection of nitrogen, air is introduced to continuously oxidize for 1-3h, preferably 3 h;
preferably, the macromolecular colorant for the grease has the following structural general formula:
formula I
Wherein R is selected from
Wherein R is1Selected from H, Cl, NO2，CH3；R2Selected from H, Cl, NO2，CH3，CN；R3Selected from H, Cl, NO2，CH3，CN；R4Selected from coco alkyl primary amine, tetradecyl primary amine, or oleyl primary amine, N-oleyl-1, 3-propylene diamine, N-coco-1, 3-propylene diamine.
The invention provides a macromolecular coloring agent for grease, which is prepared by the following steps:
step 1: preparation of reactive disperse dyes
Step 2: and (2) taking a three-neck flask, adding the active disperse dye and the acid binding agent in the step (1) into the flask, then adding No. 26 white oil as a reaction solvent, and controlling the stirring speed to be 300 r/m.
And step 3: adding fatty amine, raising the temperature to 40 ℃, reacting for 2-3h, and controlling the stirring speed to be 300 r/m.
And 4, step 4: the temperature is increased to 90 ℃ to continue the reaction for 2 to 3 hours. The stirring speed was controlled at 300 rpm.
And 5: cooling to room temperature, and then filtering to obtain the macromolecular colorant for the grease.
Further, the reactive disperse dye in the step 1 has the following structure:
formula IV:
wherein R is1＝H，Cl，NO2，CH3；R2＝H，Cl，NO2，CH3，CN；R3＝H，Cl，NO2，CH3，CN；R4＝H，Cl，CH3；R5＝H，Cl，CH3
The R is1-R5The structure of (1) is arbitrary combination
Formula III:
wherein R is1＝H，Cl，NO2，CH3Or is absent, R2＝H，Cl，NO2，CH3，CN；R3＝H，Cl，NO2，CH3，CN。
Further, the acid-binding agent in the step 2 is one or more of sodium carbonate and potassium carbonate;
further, the fatty amine in the step 3 is an amine compound of saturated long-chain alkane, such as coco primary alkyl amine, tetradecyl primary amine, oleyl primary amine, and the like; also included are diamine and polyamine compounds such as N-oleyl-1, 3-propylenediamine, N-coco-1, 3-propylenediamine, and the like;
although the reactive disperse dye is a product developed but not commonly used, the reactive disperse dye with the structure shown as formula II, formula III or formula IV developed by the invention is an important precursor of the coloring agent for macromolecular grease, and is a key factor for realizing high oil solubility and good coloring effect of the coloring agent for macromolecular grease. The solubility of the active disperse dye as the precursor raw material in the oil has obtained a great breakthrough, and the active disperse dye contains reactive active groups and does not have water-soluble groups, so the invention improves the active disperse dye by using long-chain alkane, and can color the oil with poor solubility as well as hydrocarbon and wax. And based on the high active disperse dye of solubility in the grease carry out macromolecule fatty amine grafting, obtain the better macromolecule colorant of oil solubility, further promote the solubility of dyestuff in the grease, and then promote the solubility in the grease of the colorant for macromolecule grease that is obtained based on this dyestuff preparation. The advantage of grafting macromolecular fatty amines onto the reactive disperse dyes according to the invention is that, on the one hand, the final products can be further improved: the oil solubility of the macromolecular colorant, on the other hand, the molecular weight of the final product is increased to form a macromolecular product (macromolecular colorant) with larger molecular weight, the macromolecular product is convenient to separate and purify during industrial production due to the large molecular weight, the macromolecular colorant obtained after small molecules possibly having toxicity are removed by separation and purification is environment-friendly, safe and nontoxic, and the macromolecular colorant with large molecular weight can be easily washed away when the macromolecular colorant carelessly colors skin or clothes.
The beneficial effects of the invention include:
the macromolecular colorant for the oil is suitable for coloring natural oil, wax, silicone oil, synthetic oil and animal and vegetable oil. The macromolecular colorant for the grease prepared by the preparation method has the advantages of simple production process, high solubility and complete chromatogram.
The macromolecular coloring agent prepared by the preparation method can be well compatible with natural oil, wax, silicone oil, synthetic oil and animal and vegetable oil, and provides a good coloring effect.
The macromolecular colorant prepared by the preparation method is a liquid dye, has good miscibility among colors, and is simple in color matching.
Although the raw materials prepared by the macromolecular colorant are basically micromolecules and have certain toxicity, the molecular weight of the obtained final product (macromolecular colorant) is increased after the reaction is completed by the preparation method, the safety is improved, and the unnecessary impurities and the micromolecules are removed by post-treatment, so that the content of the toxic molecules and the impurities is ensured to be weak, thereby ensuring the safety and the environmental protection of the final product of the macromolecular colorant of the invention, meanwhile, the preparation method of the invention grafts and synthesizes the micromolecule dye to obtain the macromolecular dye, on one hand, the macromolecular dye is difficult to color the skin after the molecular weight is increased, the synthesized dye is a disperse dye which is dissolved in oil and water and is not dissolved in water, so that the oil and the dye can be easily washed off by using some oil-removed products, the oil and the dye can not damage the skin, therefore, the macromolecular colorant of the invention is easy to wash off, does not stain the skin.
Detailed Description
The present invention will be further described with reference to the following specific examples, which should not be construed as limiting the scope of the invention. Unless otherwise defined, each of the raw materials used in the experimental examples section of the present invention has the ordinary technical meaning conventionally understood by those skilled in the art, or is commercially available; the manipulations performed, the parameters employed, the conditions, all have the technical meaning commonly understood by those skilled in the art.
Reagent and consumable
The commercial dye reactive dye X-3B is a commercial product and can be obtained commercially, and the respective manufacturers and product types are as follows:
commercial dye reactive dye X-3B: the type of the product of bright red X-3B from Homedo chemical company Limited in Zhejiang.
DYE1 and DYE2 are the reactive disperse DYEs synthesized by the invention, and the structural formulas are respectively shown as formula IV and formula III.
Group 1 example macromolecular colorants for fats and oils according to the invention
The group of embodiments provides a macromolecular coloring agent for grease. The macromolecular colorants for oils and fats of the present group of examples all have the structure represented by formula I below:
formula I
Wherein R is selected from
R1Selected from H, Cl, NO2、CH3Or absent; r2Selected from H, Cl, NO2、CH3、CN；R3Selected from H, Cl, NO2、CH3、CN；
R4Selected from:
the macromolecular coloring agent for the oil and fat shown in the formula I is obtained by further removing chlorine atoms on 3-positions and 5-positions of triazine rings on a core structure and grafting the chlorine atoms into macromolecular aliphatic amine on the basis of the core structures of the reactive disperse dyes shown in the formulas IV-1 to IV-60 shown in the table 1 and the reactive disperse dyes shown in the formulas III-1 to III-20 shown in the table 2.
Thus, in this particular group of embodiments, specific examples of the main structures of formula I may be found in reference to the structures of formulae IV-1 to IV-60 as illustrated in Table 1 and the structures of formulae III-1 to III-20 as illustrated in Table 2, the only difference being the replacement of the chlorine atom on the triazine ring by R4Group, and R4The radicals are then selected from: n-cocoyl-1, 3-propylenediamine
Coconut alkyl primary amine
Tetradecyl primary amine
Oil-based primary amines
And macromolecular aliphatic amine groups.
For space saving, the structural formulas of the macromolecular coloring agents for various oils grafted with macromolecular aliphatic amine groups on the basis of the structures shown in formulas IV-1 to IV-60 and the structures shown in formulas III-1 to III-20 are not drawn one by one.
According to the description and teaching of the present invention, the grafting of macromolecular aliphatic amine groups (including but not limited to the groups of N-coco-1, 3-propylenediamine, coco primary amine, tetradecyl primary amine, oleyl primary amine, and the like) and the obtaining of macromolecular colorants for oils and fats based on the structures shown in formulas IV-1 to IV-60 and structures shown in formulas III-1 to III-20 according to the preparation methods described in Experimental examples 3-7 was unambiguously realized and obtained by those skilled in the art. Any operation of grafting a macromolecular aliphatic amine group on the basis of the structures shown in the formulas IV-1 to IV-60 and the structures shown in the formulas III-1 to III-20, or any compound with the structure shown in the formula I, or the operation of grafting the compounds with the structures shown in the formulas IV-1 to IV-60 and the structures shown in the formulas III-1 to III-20 on the 3-and 5-positions of the triazine ring by using macromolecular aliphatic amines except N-cocoyl-1, 3-propylene diamine, cocoalkyl primary amine, tetradecyl primary amine and oleyl primary amine falls within the protection scope of the present invention.
Group 2 example, method for producing macromolecular colorant for oil and fat of the present invention
The embodiment of the group provides a preparation method of a macromolecular coloring agent for grease. All embodiments of this group share the following common features: the preparation method comprises the following steps: adding a solvent into the active disperse dye, uniformly mixing, adding fatty amine, and heating.
The solvent is generally oil-soluble, and because the normally active disperse dyes are solid, the active disperse dyes are dissolved in the solvent to better dissolve the dyes, so that the miscibility of the final product in the oil is improved. DYE1-DYE2 are all useful as precursor materials for the colorants of the present invention, and have in common that they have reactive groups, such as halogen groups Cl, Br, etc., which react as reactive groups with amino groups to effect condensation reactions.
The core principle of the preparation method for improving the oil solubility of the macromolecular colorant is that fatty amine is adopted to modify the active disperse dye, and the fatty amine, such as coconut oil alkyl primary amine, has the characteristic of oil dissolution, and is modified on the basis of finding a proper dye structure, so that the final product macromolecular colorant obtains excellent oil solubility.
In a preferred embodiment, the active disperse dye, the solvent and the fatty amine are used in the following ratio by mass: 1-2: 5-15: 1-2, preferably 1: 10: 1, the positive effect of using this quantity ratio on the improvement of oil solubility lies in the improvement of the completeness of the reaction.
In some specific embodiments, the reactive disperse dye is selected from the following structures:
formula II:
wherein R is1Selected from H, Cl, NO2，CH3Or is absent; r2Selected from H, Cl, NO2，CH3Or absent, CN; r3＝H，Cl，NO2，CH3CN or absent; r4Selected from H, Cl, CH3Or is absent; r5Selected from H, Cl, CH3Or a benzene ring attached to the position and its ortho-position;
the compound of formula II may further specifically include compounds of formula III or formula IV below:
formula III:
formula IV:
wherein R is1＝H，Cl，NO2，CH3Or is absent, R2＝H，Cl，NO2，CH3Or is absent, CN, R3＝H，Cl，NO2，CH3CN is either absent.
In particular embodiments, the solvent is selected from white oil, cyclopentadimethylsiloxane, vegetable fats and oils, animal fats and oils, dimethicone;
the white oil is preferably No. 26 white oil because the white oil is cheap and has good dissolving effect;
in other embodiments, the fatty amine is selected from a primary amine, a diamine, or a polyamine;
the primary amine is preferably cocoalkyl primary amine, tetradecyl primary amine, or oleyl primary amine;
the diamine is preferably N-oleyl-1, 3-propylenediamine, N-coco-1, 3-propylenediamine;
the polyamine is selected from: polyethylene polyamine, polyethylene imine.
In a further embodiment, an acid-binding agent is added into the reactive disperse dye before the solvent is added into the reactive disperse dye; the addition amount of the acid-binding agent and the dosage proportion of the active disperse dye are as follows: the mass ratio is 1-2: 5-15, preferably 1: 10, and the dosage ratio has the following positive effects on improving the oil solubility of the final product: the completeness of the reaction is improved.
The acid-binding agent is preferably sodium carbonate, potassium carbonate and potassium hydroxide, and the effect of adding the acid-binding agent is to improve the reaction rate and the acid reaction produced in the reaction.
In a preferred embodiment, the temperature rise means that the temperature is raised to 40-60 ℃, preferably 40 ℃, for 2-3h, preferably 3h, and then raised to 80-90 ℃, preferably 90 ℃, for 2-3h, and the respective effects of the 2-stage temperature rise are to react with chlorine on cyanuric chloride, the second chlorine reaction temperature is about 40 ℃, and the third chlorine reaction temperature is about 90 ℃;
or the like, or, alternatively,
raising the temperature to 80-90 ℃, preferably 80 ℃, under the protection of nitrogen for reaction for 3-6h, preferably 6h, wherein the direct raising of the temperature to 80 ℃ has the function of improving the reaction speed and the minimum temperature required by the reaction.
In other embodiments, the blending means stirring at 100-500 rpm, preferably 300 rpm.
In a more preferred embodiment, after the reaction is carried out for 3 to 6 hours, preferably 6 hours at 80 to 100 ℃, preferably 80 ℃ under the protection of nitrogen, the oxidation is continued for 1 to 3 hours, preferably 3 hours by introducing air.
Experimental example 1
Taking a three-necked bottle, adding 14g of paranitroaniline, 30g of hydrochloric acid and 30g of water, pulping for 1h, cooling to 0 ℃, then adding 7.5g of sodium nitrite, preserving heat for 1h, and adding 2g of sulfamic acid to obtain a diazo liquid for later use; in another three-necked flask, 9g of aniline and 10g of water were added, and then the diazo solution was slowly dropped into the flask over 30 minutes, and the temperature was maintained at 5 ℃. Coupling time 5 h. After the reaction is completed, 18g of cyanuric chloride is added, the temperature is controlled to be 5 ℃, the pH value is 3-4, and the condensation time is 3 hours. After the reaction was completed, the pH was adjusted to neutral and then filtered and washed with water to obtain 25g of a yellow filter cake designated DYE1 having the chemical structure described in formula IV-1 below.
In addition, DYE1 may also have chemical structures represented by the following formulas IV-2 to IV-60, and the preparation method thereof is substantially identical to the preparation method, and only some ring-linking parameters are different, as shown in the following Table 1:
TABLE 1 chemical Structure of DYE1 and method of making the same
Experimental example 2
Adding 9g of aniline, 30g of hydrochloric acid and 30g of water into a three-necked bottle, pulping for 1h, cooling to 0 ℃, adding 7.5g of sodium nitrite, preserving heat for 1h, and adding 2g of sulfamic acid to obtain a diazo liquid for later use; in another three-necked bottle, 14g of 1-naphthylamine and 10g of water are added, and then the diazo liquid is slowly dripped into the bottle, the dripping is finished after 30 minutes of controlled time, and the temperature is kept at 5 ℃. Coupling time 5 h. After the reaction is completed, 18g of cyanuric chloride is added, the temperature is controlled to be 5 ℃, the pH value is 3-4, and the condensation time is 3 hours. After the reaction was completed, the pH was adjusted to neutrality and then filtered and washed with water to obtain 30g of a red filter cake designated DYE2 having the chemical structure shown in the following formula III-1. In addition, DYE2 may also have chemical structures represented by the following formulas III-2 to III-20, and the preparation method thereof is substantially identical to the preparation method, and only some ring-linking parameters are different, as shown in the following Table 2:
TABLE 2 chemical Structure of DYE2 and method of making the same
Experimental example 3
10g of active disperse DYE DYE1 and 1g of sodium carbonate are added into a flask with a three-neck flask, then 100g of No. 26 white oil is added, and the stirring speed is controlled to be 300 r/min. Cocoyl primary amine (NH) is added2C12H25)10g, the temperature is increased to 40 ℃ for reaction for 2 hours, and then the temperature is increased to 90 ℃ for reaction for 3 hours. Cooling to room temperature, and filtering to obtain yellow filtrate, i.e. macromolecular colorant 1 #.
Experimental example 4
10g of active disperse DYE DYE2 and 1g of sodium carbonate are added into a flask with a three-neck flask, then 100g of No. 26 white oil is added, and the stirring speed is controlled to be 300 r/min. Cocoyl primary amine (NH) is added2C12H25)10g, the temperature is firstly increased to 40 ℃ for reactionAfter 2h, the temperature is raised to 90 ℃ and the reaction lasts for 3 h. Cooling to room temperature, and filtering to obtain red filtrate, i.e. macromolecular colorant No. 2.
Experimental example 5
10g of disperse DYE DYE1 was added to a flask with three necks, and then 100g of No. 26 white oil was added thereto, and the stirring speed was controlled at 300 rpm. Adding tetradecyl primary amine (NH)2C14H29) Introducing nitrogen into the mixture 10g, raising the temperature to 80 ℃, reacting for 6 hours, introducing air into the mixture after the reaction is finished, continuously oxidizing for 3 hours, cooling the mixture to room temperature, and filtering to obtain yellow filtrate, namely the macromolecular colorant No. 3.
Experimental example 6
10g of disperse DYE DYE2 was added to a flask with three necks, and then 100g of No. 26 white oil was added thereto, and the stirring speed was controlled at 300 rpm. Adding tetradecyl primary amine (NH)2C14H29) Introducing nitrogen into the mixture 10g, raising the temperature to 80 ℃, reacting for 6 hours, introducing air into the mixture after the reaction is finished, continuously oxidizing for 3 hours, cooling the mixture to room temperature, and filtering to obtain red filtrate, namely the macromolecular colorant No. 4.
Experimental example 7
10g of active disperse DYE DYE1 and 1g of sodium carbonate are added into a flask with a three-neck flask, then 100g of No. 26 white oil is added, and the stirring speed is controlled to be 300 r/min. Adding N-cocoyl-1, 3-propylene diamine (NH)2C21H42N)10g, the temperature is raised to 40 ℃ for reaction for 2h, and then the temperature is raised to 90 ℃ for reaction for 3 h. Cooling to room temperature, and filtering to obtain yellow filtrate, i.e. macromolecular colorant No. 5. H3C
Comparative example 1
10g of reactive dye X-3B and 1g of sodium carbonate are added into a flask with a three-neck flask, then 20g of dipropylene glycol methyl ether is added, and the stirring speed is controlled to be 300 r/min. 10g of cocoyl primary amine is added, the temperature is raised to 40 ℃ for reaction for 2h, and then the temperature is raised to 90 ℃ for reaction for 3 h. Cooling to obtain the dye number 6.
Experimental example 8 oil solubility experiment of reactive disperse dye and macromolecular colorant according to the present invention
The DYE1-2 prepared in the above experimental examples 1-2, the macromolecular colorant # 1-5 prepared in the experimental examples 3-7, the DYE # 6 prepared in the comparative example 1, and the reactive DYE X-3B of the prior art were respectively tested for their solubility in oils and fats by the following specific test methods:
hydroxyl silicone oil, cyclopentadimethicone, jojoba oil, diesel oil, beeswax and lubricating oil are respectively used as different grease solvents;
the following samples were taken: reactive disperse DYE DYE1 (samples of 60 different products), DYE2 (samples of 20 different products), macromolecular colorant 1#, macromolecular colorant 2#, macromolecular colorant 3#, macromolecular colorant 4#, macromolecular colorant 5#, DYE 6#, and reactive DYE X-3B, wherein 10g of each sample is gradually and slowly added into 100g of each grease solvent in batches to form a group, and each group is repeated for 3 times. In each repetition, the addition method can be firstly carried out by small amount and quantitative addition, such as 1-3g dropwise at one time, and then the addition amount is increased under the condition that a small amount is soluble. If the sample is very insoluble, the amount may be further reduced, for example, by adding only 1g or 0.5g or 0.1g at a time until the sample is completely dissolved in the oil. And stopping adding when the phenomena of insolubilization, layering, precipitation and the like appear in the adding process, and counting the total amount of the sample added before. The amount of the dissolved compound (unit: g) was obtained.
The test results are based on the average of 3 replicates in each group and the statistical solubility data are shown in table 3 below:
TABLE 3 comparison of the amount of dye and colorant dissolved in various oils and fats obtained in the respective experimental examples and comparative examples
From the results of the above examples, it can be seen that the untreated commercial dye reactive dye X-3B is insoluble in oils and fats and does not exert any coloring effect, while the macromolecular coloring agent of the present invention has extremely high solubility in oils and fats and strong coloring power, and can color commercially available natural oils and fats, waxes, silicone oils, synthetic oils and fats, animal and vegetable oils and fats, and the like.
The preferred embodiments of the invention disclosed above are intended to be illustrative only. The preferred embodiments are not intended to be exhaustive or to limit the invention to the precise embodiments disclosed. Obviously, many modifications and variations are possible in light of the above teaching. The embodiments were chosen and described in order to best explain the principles of the invention and the practical application, to thereby enable others skilled in the art to best utilize the invention. The invention is limited only by the claims and their full scope and equivalents.
Claims (10)
1. A reactive disperse dye, characterized by having a chemical structure represented by formula II:
formula II
Wherein R is1Selected from H, Cl, NO2，CH3Or is absent; r2Selected from H, Cl, NO2，CH3Or absent, CN; r3＝H，Cl，NO2，CH3CN or absent; r4Selected from H, Cl, CH3Or is absent; r5Selected from H, Cl, CH3Or a benzene ring attached to the position and its ortho-position.
2. The reactive disperse dye according to claim 1, wherein the reactive disperse dye is selected from the following structures:
formula IV
Or the like, or, alternatively,
formula III
3. A preparation method of a reactive disperse dye is characterized by comprising the following steps: diazo compound is added into aromatic amine for coupling reaction, and cyanuric chloride is added for condensation reaction.
4. The method for preparing a reactive disperse dye according to claim 3, wherein water is added to the aromatic amine before the diazo compound is added;
the dosage ratio of the aromatic amine to the water is 9-14: 10;
preferably, the diazo compound is slowly dripped into the mixed solution of the aromatic amine and the water, and the slow dripping time is preferably 30 minutes;
more preferably, the slow dropwise addition is carried out at low temperature; the low temperature is preferably 5 ℃; preferably, the time of the coupling reaction is 3 to 8 hours
Preferably 5 h;
preferably, the condensation reaction time is 1-3h, preferably 3h, and the pH value is 3-4;
preferably, both the coupling reaction and the condensation reaction are carried out at low temperatures; the low temperature is preferably 5 ℃.
5. The preparation method of the reactive disperse dye according to claim 3, wherein the aromatic amine, the diazo compound and the cyanuric chloride are used in the following ratio: the mass ratio is 9-14: 18;
the preparation method further comprises the following steps: the pH of the product obtained by the condensation reaction is adjusted to be neutral, and then the product is filtered and washed by water.
6. The method for preparing the reactive disperse dye according to any one of claims 3 to 5, wherein the diazo compound is diazo liquid;
preferably, the diazo liquid is prepared by the following method:
adding strong acid and water into the aniline compound, uniformly mixing, adding sodium nitrite, standing, and finally adding sulfamic acid.
7. The method for preparing the reactive disperse dye according to claim 6, wherein the aniline compound is selected from the group consisting of: aniline, p-nitroaniline, optionally 2-4, dinitroaniline, o-cyano-p-nitroaniline, 2, 6-dibromo-4-nitroaniline, 3-amino-5-nitrobenzoisothiazole;
preferably, the strong acid is selected from: hydrochloric acid, sulfuric acid;
preferably, the dosage ratio of the aniline compound, the strong acid, the water, the sodium nitrite and the sulfamic acid is 1-15: 3-30: 0.5-2: 2, preferably 9-14: 30: 7.5: 2;
the advantage of using the above-mentioned ratio of amounts is that the reaction is fully completed.
Preferably, the mixing refers to pulping for 1 h;
preferably, the temperature is reduced to 0 ℃ after uniform mixing;
preferably, the standing refers to standing at 0 ℃ for 1 h.
8. Use of the reactive disperse dye according to claim 1 or 2, and/or the reactive disperse dye prepared by the preparation method according to any one of claims 3 to 7, for preparing a colorant.
9. The use according to claim 8, characterized in that the solvent is added into the reactive disperse dye, the mixture is uniformly mixed, and then the aliphatic amine is added for heating;
preferably, the solvent is selected from white oil, cyclopentadidimethyl siloxane, vegetable oil and fat, animal oil and fat, and dimethyl silicone oil;
the white oil is preferably No. 26 white oil;
preferably, the fatty amine is selected from primary amines, diamines or polyamines;
the primary amine is preferably cocoalkyl primary amine, tetradecyl primary amine, or oleyl primary amine;
the diamine is preferably N-oleyl-1, 3-propylenediamine, N-coco-1, 3-propylenediamine;
the polyamine is selected from: polyethylene polyamine, polyethylene imine.
Preferably, an acid-binding agent is added into the reactive disperse dye before the solvent is added;
the acid-binding agent is preferably sodium carbonate, potassium carbonate or potassium hydroxide;
preferably, the colorant refers to a macromolecular colorant for grease.
10. Use according to claim 9, wherein the warming refers to warming to 40-60 ℃, preferably 40 ℃, for 2-3h, preferably 3h, and then warming to 80-100 ℃, preferably 90 ℃, for 2-3 h; or heating to 80-100 deg.C, preferably 80 deg.C, under nitrogen protection, and reacting for 3-6h, preferably 6 h;
preferably, the mixing means to mix by stirring at 100-.
Preferably, after the temperature is raised to 80-100 ℃, preferably 80 ℃, and the reaction is carried out for 3-6h, preferably 6h under the protection of nitrogen, air is introduced to continuously oxidize for 1-3h, preferably 3 h;
preferably, the macromolecular colorant for the grease has the following structural general formula:
formula I
Wherein R is selected from
Wherein R is1Selected from H, Cl, NO2，CH3；R2Selected from H, Cl, NO2，CH3，CN；R3Selected from H, Cl, NO2，CH3，CN；R4Selected from coco alkyl primary amine, tetradecyl primary amine, or oleyl primary amine, N-oleyl-1, 3-propylene diamine, N-coco-1, 3-propylene diamine.
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| US3527746A (en) * | 1964-07-02 | 1970-09-08 | Acna | Monoazo heterocyclic containing triazine dyestuffs |
| CN104016880A (en) * | 2014-06-09 | 2014-09-03 | 苏州大学 | Special precursor for azo reactive disperse dyes and use of special precursor |
| CN105440726A (en) * | 2015-12-18 | 2016-03-30 | 苏州大学 | Supercritical CO2 dyeing special-purpose azo-type active disperse dye |
| CN109554005A (en) * | 2018-11-16 | 2019-04-02 | 安徽清彩科技有限公司 | A kind of preparation method of the active bio base macromolecular dyestuff of type containing chloro-s-triazine |
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