CN116970288A - Water-soluble acrylamide type amino C acid dye, and synthetic method and application thereof - Google Patents
Water-soluble acrylamide type amino C acid dye, and synthetic method and application thereof Download PDFInfo
- Publication number
- CN116970288A CN116970288A CN202310684011.5A CN202310684011A CN116970288A CN 116970288 A CN116970288 A CN 116970288A CN 202310684011 A CN202310684011 A CN 202310684011A CN 116970288 A CN116970288 A CN 116970288A
- Authority
- CN
- China
- Prior art keywords
- acid
- amino
- dye
- water
- molar ratio
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 239000000980 acid dye Substances 0.000 title claims abstract description 23
- -1 amino C acid Chemical compound 0.000 title claims description 36
- 238000010189 synthetic method Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims abstract description 38
- 239000011521 glass Substances 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 11
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 20
- 238000009833 condensation Methods 0.000 claims description 20
- 230000005494 condensation Effects 0.000 claims description 20
- 239000012954 diazonium Substances 0.000 claims description 17
- 150000001989 diazonium salts Chemical class 0.000 claims description 17
- 238000003756 stirring Methods 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 235000010288 sodium nitrite Nutrition 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 239000011780 sodium chloride Substances 0.000 claims description 10
- 238000005406 washing Methods 0.000 claims description 10
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 claims description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 9
- 239000005457 ice water Substances 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 6
- 230000008878 coupling Effects 0.000 claims description 5
- 238000010168 coupling process Methods 0.000 claims description 5
- 238000005859 coupling reaction Methods 0.000 claims description 5
- 239000012065 filter cake Substances 0.000 claims description 5
- 230000001376 precipitating effect Effects 0.000 claims description 5
- 238000005185 salting out Methods 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 5
- APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 claims description 4
- 238000006193 diazotization reaction Methods 0.000 claims description 4
- 238000001291 vacuum drying Methods 0.000 claims description 4
- 230000001105 regulatory effect Effects 0.000 claims description 3
- 238000000967 suction filtration Methods 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 11
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 abstract description 7
- 230000037048 polymerization activity Effects 0.000 abstract description 3
- 238000001308 synthesis method Methods 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 230000000052 comparative effect Effects 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 2
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 2
- 238000003828 vacuum filtration Methods 0.000 description 2
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
-
- 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
- C09B43/124—Preparation of azo dyes from other azo compounds by acylation of amino groups with monocarboxylic acids, carbamic esters or halides, mono- isocyanates, or haloformic acid esters
- C09B43/128—Aliphatic, cycloaliphatic or araliphatic acids
Abstract
The invention relates to a water-soluble acrylamide amino C acid dye, a synthesis method and application thereof. The dye obtained by the invention has simple synthesis process and high yield and purity; the acrylamide group containing unsaturated C=C bond is introduced into dye molecule, so that the dye molecule has extremely high polymerization activity, and a new method is provided for preparing the colored organic glass.
Description
Technical Field
The invention relates to a water-soluble dye, in particular to a synthesis method of an acrylamide amino C acid dye and application of the acrylamide amino C acid dye in colored organic glass.
Background
Amino C is often used for synthesizing yellow dye, such as active yellow X-R, and the dye containing amino C acid has the characteristics of bright color and stable structure. By changing the substituent groups of the dye, certain adjustment can be made on the properties, such as water solubility, color depth and reactivity. The traditional amino C acid series dyes are only suitable for dyeing cotton, hemp and wool fibers, which limits the application of the dyes to a great extent.
The acrylamide group has high polymerization activity, the acryloyl can be conveniently and rapidly introduced into the dye in an acryloyl chloride mode, the dye has polymerization capacity under the condition of not changing the color of the dye, and the dye can be applied to the preparation of colored organic glass through copolymerization with methyl acrylate.
Disclosure of Invention
The invention aims to provide a synthesis method of a water-soluble acrylamide amino C acid dye and application thereof in colored organic glass, wherein an acryl is introduced under the premise of not damaging the bright color of the dye, so that the dye has extremely high polymerization capacity, and the dye is copolymerized with methyl methacrylate to prepare the colored organic glass, so that the application of the amino C acid dye is widened.
In order to achieve the purpose, the invention adopts the following technical scheme that the water-soluble acrylamide amino C acid dye has the following structure:
the invention also provides a preparation method of the water-soluble acrylamide amino C acid dye, which comprises the following steps:
diazotization of amino C acid to obtain diazonium salt system;
coupling diazonium salt and m-methylaniline to prepare a dye chromophore system;
(III) condensing the acryloyl chloride with a chromophore to prepare a condensation system;
and (IV) salting out the condensed system, and then carrying out suction filtration, washing and drying.
Further, the step (one) is as follows: the step (I) is as follows: dispersing amino C acid in water under stirring, adding concentrated hydrochloric acid (10 mol/L) under ice water bath, rapidly adding aqueous solution of sodium nitrite, and maintaining low temperature for reaction for 1 hour to obtain diazonium salt system; preferably, the molar ratio of the amino C acid to the concentrated hydrochloric acid is 1:2 to 1:3.5, the molar ratio of the amino C acid to the sodium nitrite is 1:1.04, and the concentration of the sodium nitrite aqueous solution is 30-35 wt%; more preferably, the molar ratio of the amino C acid to concentrated hydrochloric acid is 1:3.
Further, the step (two) is as follows: injecting m-methylaniline into a diazonium salt system, regulating the pH value of a saturated sodium carbonate solution to be 4-5, and heating the system to 75 ℃ within 3 hours to prepare a dye chromophore system; preferably, the molar ratio of m-methylaniline to amino C acid is 0.8:1-1.05:1.
further, the step (III) is as follows: dropwise adding the dye chromophore system into ice water bath, maintaining pH=6-7 during which, maintaining low temperature for reaction for 1 hour to prepare a condensation system; preferably, the molar ratio of the acryloyl chloride to the amino C acid is 1:1.5-1:2.
Further, the step (four) is as follows: adding sodium chloride into the condensation system under slow stirring, stirring for 5 hours, uniformly precipitating the dye, performing vacuum filtration on the system under reduced pressure, washing a filter cake with ethanol, and performing vacuum drying to obtain the water-soluble acrylamide type amino C acid dye; preferably, the mass of sodium chloride used is 10-25% of the volume of the condensation system; more preferably, the mass of sodium chloride used is 20% of the volume of the condensation system.
The preparation method of the water-soluble acrylamide type amino C acid dye comprises the following steps:
diazotisation of (one) amino C acids
Adding amino C acid into ice water bath, adding concentrated hydrochloric acid (10 mol/L), quickly adding aqueous solution of sodium nitrite, and maintaining low temperature for reaction for 1 hour to obtain a diazonium salt system, wherein the molar ratio of the amino C acid to the concentrated hydrochloric acid is 1:2-1:3.5, the molar ratio of the o-aminobenzenesulfonic acid to the sodium nitrite is 1:1.04, and the concentration of the aqueous solution of the sodium nitrite is 30-35 wt%;
coupling of diazonium salts with meta-methylanilines
Injecting m-methylaniline into a diazonium salt system, regulating the pH value of a saturated sodium carbonate solution to be 4-5, and heating the system to 75 ℃ within 3 hours to prepare a dye chromophore system, wherein the molar ratio of the methylaniline to the amino C acid is 0.8:1-1.05:1, a step of;
condensation of (III) acryloyl chloride with a chromophore
Dropwise adding the dye chromophore system into ice water bath, maintaining pH=6-7 during which, maintaining low temperature for reaction for 1 hour to obtain a condensation system, wherein the molar ratio of the acryloyl chloride to the amino C acid is 1:1.5-1:2;
salting out, suction filtering, washing and drying the system
Adding sodium chloride into the condensation system under slow stirring, stirring for 5 hours, uniformly precipitating the dye, decompressing and filtering the system, washing a filter cake by using ethanol, and then vacuum drying to obtain the water-soluble acrylamide type amino C acid dye, wherein the mass of the sodium chloride is 10-25% of the volume of the condensation system.
Preferably, the molar ratio of the amino C acid to the concentrated hydrochloric acid in the step (one) is 1:3; the mass of sodium chloride used in the step (four) is 20 percent of the volume of the condensation system
The invention further provides application of the water-soluble acrylamide amino C acid dye in preparation of colored organic glass.
The invention has the advantages that: the dye molecule synthesis process is simple, and the prepared dye has high yield and purity; the introduction of the acrylamide group containing unsaturated C=C bond ensures that the acrylamide group has extremely high polymerization activity, thereby providing a new idea for preparing the colored organic glass; the colored organic glass prepared by the dye prepared by the invention has good mechanical property and thermal stability.
The specific embodiment is as follows:
the invention is further illustrated by the following examples.
Example 1: preparation of water-soluble acrylamide type amino C acid dye
(1) Diazotisation of amino C acids
Taking 30.3 g of amino C acid in 300 ml water, uniformly stirring in an ice water bath, adding 10.6 g of sodium carbonate for neutralization, then adding 30 ml g of concentrated hydrochloric acid (10 mol/L), rapidly adding a 30 wt% aqueous solution prepared from 7.2 g of sodium nitrite, and maintaining the temperature at 10-15 ℃ for diazotization reaction for 0.5 hour to prepare a diazonium salt system;
(2) Coupling of diazonium salts with meta-methylanilines
Injecting 11.3-ml m-methylaniline into a diazonium salt system, adding a saturated sodium carbonate solution to adjust the pH value to be 4-5, and heating the system to 75 ℃ within 3 hours to prepare a dye chromophore system;
(3) Condensation of acryloyl chloride with chromophore
Dropwise adding 16 ml acrylic chloride into an ice water bath, maintaining the pH value to be 6-7, and maintaining the low temperature for reaction for 1 hour after the dropwise addition is finished to prepare a condensation system;
(4) Salting out, suction filtering, washing and drying
Adding sodium chloride with the mass ratio of 20% of the volume of the condensation system into the condensation system in batches under slow stirring, stirring for 5 hours, uniformly precipitating the dye, decompressing and filtering the system, washing a filter cake by using ethanol, and then drying in vacuum to obtain the water-soluble acrylamide type amino C acid dye.
The nuclear magnetic detection results are as follows:
1 H NMR (400 MHz, DMSO-d 6 ) δ 10.76 (s, 1H), 9.55 (d, J = 2.0 Hz, 1H), 8.94 – 8.91 (m, 1H), 8.46 (d, J = 2.0 Hz, 1H), 8.05 (dd, J = 7.2, 1.2 Hz, 1H), 7.88 (d, J = 2.0 Hz, 1H), 7.76 – 7.70 (m, 2H), 7.57 (dd, J = 8.4, 7.2 Hz, 1H), 6.60 (dd, J = 17.2, 10.4 Hz, 1H), 6.30 (dd, J = 17.2, 2.0 Hz, 1H), 5.79 (dd, J = 10.0, 2.0 Hz, 1H), 2.73 (s, 3H)。
example 2: preparation of colored organic glass
In a 500ml three-necked flask. 1 g the water-soluble acrylamide type H acid dye prepared in example 1, 100 ml water, 100 ml methyl methacrylate, 0.5 g potassium persulfate and 0.5 g sodium bisulphite were added and nitrogen protection was introduced for reaction at 70 ℃ for 5 hours. After the reaction is finished, the organic glass with different color depths is obtained by filtering the system.
Comparative example: to illustrate the superiority of the samples made in this experiment, the following are samples that were not made according to the conditions set forth in the examples.
Comparative example 1: preparation of water-soluble acrylamide type amino C acid dye
(1) Diazotisation of amino C acids
Taking 30.3 g of amino C acid in 300 ml water, uniformly stirring in an ice water bath, adding 10.6 g of sodium carbonate for neutralization, then adding 30 ml g of concentrated hydrochloric acid (10 mol/L), rapidly adding a 30 wt% aqueous solution prepared from 7.2 g of sodium nitrite, and maintaining the temperature at 10-15 ℃ for diazotization reaction for 0.5 hour to prepare a diazonium salt system;
(2) Coupling of diazonium salts with meta-methylanilines
Injecting 11.3-ml m-methylaniline into a diazonium salt system, adding a saturated sodium carbonate solution to adjust the pH value to be 4-5, and heating the system to 75 ℃ within 3 hours to prepare a dye chromophore system;
(3) Condensation of acrylic anhydride with chromophore
Cooling the dye chromophore system to 40 ℃, dropwise adding 25g of acrylic anhydride, maintaining pH=6-7 during the period, and reacting for 2 hours to prepare a condensation system;
(4) Salting out, suction filtering, washing and drying
And (3) adding sodium chloride with the total volume of 20% in batches into the condensation system under slow stirring, stirring for 5 hours, uniformly precipitating the dye, performing vacuum filtration on the system under reduced pressure, washing a filter cake by using ethanol, and performing vacuum drying to obtain the water-soluble acrylamide type H acid dye.
Comparative example 2: preparation of colored organic glass
In a 500ml three-necked flask. 1 g of the water-soluble acrylamide type H acid dye prepared in the example 2, 100 ml of water, 100 ml of methyl methacrylate, 0.5 g of potassium persulfate and 0.5 g of sodium bisulphite are added, and nitrogen is introduced for protection, and the reaction is carried out at 70 ℃ for 5 hours. After the reaction is finished, the organic glass with different color depths is obtained by filtering the system.
Table 1 shows the yields and purities of the dyes obtained in example 1 and comparative example 1, and Table 2 shows the properties of the organic glasses obtained in example 2 and comparative example 2.
TABLE 1 dye yield and purity
| Yield (%) | Purity (%) | |
| Example 1 | 96 | 96% |
| Comparative example 1 | 81 | 87% |
TABLE 2 Properties of organic glass
| Impact Strength (J/m) | Tensile Strength (MPa) | Flexural Strength (MPa) | Heat distortion temperature (DEG C) | Transparency (%) | |
| Example 2 | 21.9 | 66.2 | 125 | 95 | 92.6 |
| Comparative example 2 | 18.2 | 61.2 | 110 | 79 | 90.1 |
As can be seen from tables 1 and 2, the dyes of the present invention have good yields and purities, and the organic glass prepared from the dyes of the present invention has good mechanical properties and thermal stability.
Those skilled in the art will further recognize that the invention may be embodied in other specific forms without departing from the spirit or central characteristics thereof. Since the foregoing description of the invention discloses only exemplary embodiments thereof, it should be understood that other variations are considered to be within the scope of the invention. Therefore, the present invention is not limited to the specific embodiments described in detail herein. Rather, reference should be made to the appended claims for indicating the scope and content of the invention.
Claims (11)
1. A water-soluble acrylamide type amino C acid dye characterized by having the following structure:
2. the method for preparing a water-soluble acrylamide type amino C acid dye according to claim 1, comprising the steps of:
diazotization of amino C acid to obtain diazonium salt system;
coupling diazonium salt and m-methylaniline to prepare a dye chromophore system;
(III) condensing the acryloyl chloride with a chromophore to prepare a condensation system;
and (IV) salting out the condensed system, and then carrying out suction filtration, washing and drying.
3. The method of claim 2, wherein the step (one) is: dispersing amino C acid in water under stirring, adding concentrated hydrochloric acid (10 mol/L) under ice water bath, rapidly adding aqueous solution of sodium nitrite, and maintaining low temperature for reaction for 1 hr to obtain diazonium salt system.
4. The method according to claim 3, wherein the molar ratio of the amino C acid to the concentrated hydrochloric acid is 1:2 to 1:3.5, the molar ratio of the amino C acid to the sodium nitrite is 1:1.05, and the concentration of the sodium nitrite aqueous solution is 30-35 wt%.
5. The method of claim 2, wherein the step (two) is: m-methylaniline is injected into a diazonium salt system, the pH value of a saturated sodium carbonate solution is regulated to be 4-5, and the temperature of the system is increased to 75 ℃ within 3 hours to prepare a dye chromophore system.
6. The method of claim 5, wherein the molar ratio of m-methylaniline to amino C acid is 1.05:1.
7. the method according to claim 2, wherein the step (iii) is: the dye chromophore system is placed in ice water bath, and the acryloyl chloride is added dropwise, wherein the pH=6-7 is maintained during the period, and the condensation system is prepared by maintaining the low temperature for reaction for 1 hour.
8. The method of claim 7, wherein the molar ratio of acryloyl chloride to amino C acid is 1:1.5 to 1:2.
9. The method according to claim 2, wherein the step (four) is: adding sodium chloride into the condensation system under slow stirring, stirring for 5 hours, uniformly precipitating the dye, decompressing and filtering the system, washing a filter cake by using ethanol, and then vacuum drying to obtain the water-soluble acrylamide type H acid dye.
10. The preparation method according to claim 9, wherein the mass of sodium chloride used is 10-25% of the total volume.
11. Use of a water-soluble amino C acid dye according to claim 1 for the preparation of coloured organic glass.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310684011.5A CN116970288A (en) | 2023-06-10 | 2023-06-10 | Water-soluble acrylamide type amino C acid dye, and synthetic method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310684011.5A CN116970288A (en) | 2023-06-10 | 2023-06-10 | Water-soluble acrylamide type amino C acid dye, and synthetic method and application thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116970288A true CN116970288A (en) | 2023-10-31 |
Family
ID=88478580
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310684011.5A Pending CN116970288A (en) | 2023-06-10 | 2023-06-10 | Water-soluble acrylamide type amino C acid dye, and synthetic method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN116970288A (en) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3168512A (en) * | 1960-04-11 | 1965-02-02 | Ciba Ltd | Chromiferous azo dyestuffs containing an 8-hydroxyquinoline radical |
| US3255173A (en) * | 1962-06-22 | 1966-06-07 | Basf Ag | Fiber reactive monoazo and disazo dyes with an indole coupling component |
| CN101575458A (en) * | 2009-06-12 | 2009-11-11 | 北京化工大学 | Water-soluble azobenzene dye with polymerization activity and preparation method thereof |
| CN104284942A (en) * | 2012-04-27 | 2015-01-14 | 兴和株式会社 | Stable polymerizable UV-absorbing colorant for intraocular lens |
| CN115093502A (en) * | 2022-07-22 | 2022-09-23 | 金陵科技学院 | Preparation method of contact lens with pH indicating function |
-
2023
- 2023-06-10 CN CN202310684011.5A patent/CN116970288A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3168512A (en) * | 1960-04-11 | 1965-02-02 | Ciba Ltd | Chromiferous azo dyestuffs containing an 8-hydroxyquinoline radical |
| US3255173A (en) * | 1962-06-22 | 1966-06-07 | Basf Ag | Fiber reactive monoazo and disazo dyes with an indole coupling component |
| CN101575458A (en) * | 2009-06-12 | 2009-11-11 | 北京化工大学 | Water-soluble azobenzene dye with polymerization activity and preparation method thereof |
| CN104284942A (en) * | 2012-04-27 | 2015-01-14 | 兴和株式会社 | Stable polymerizable UV-absorbing colorant for intraocular lens |
| CN115093502A (en) * | 2022-07-22 | 2022-09-23 | 金陵科技学院 | Preparation method of contact lens with pH indicating function |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO135589B (en) | ||
| CN110499218B (en) | Efficient environment-friendly acid soaping agent and preparation method thereof | |
| CN113292867B (en) | Environment-friendly reactive dye and preparation method thereof | |
| CN113583468A (en) | Dispersed brown and preparation method thereof | |
| CN116970288A (en) | Water-soluble acrylamide type amino C acid dye, and synthetic method and application thereof | |
| CN111484753B (en) | Sun-proof easy-to-wash red azo disperse dye and preparation method thereof | |
| CN104927064B (en) | A kind of preparation method of the high molecular dye based on hyperbranched polyurethane | |
| CN111484751B (en) | Alkali washable sun-proof orange azo disperse dye and preparation method thereof | |
| CN116790133A (en) | Water-soluble acrylamide type H acid dye and synthetic method and application thereof | |
| CN116694099A (en) | Water-soluble acrylamide bromamine acid dye, and synthetic method and application thereof | |
| CN110668977B (en) | Preparation process of lauroyl arginine ethyl ester hydrochloride | |
| CN116814090A (en) | Water-soluble diacryloyl amino C acid dye and synthesis method and application thereof | |
| CN104478887A (en) | Reactive turquoise blue dye semifinished product, and preparation method and application thereof | |
| CN111270539B (en) | Color fixing agent and preparation method thereof | |
| JP2004531488A (en) | Condensation products of hydroxycarboxylic acid and glycol or glycerin useful as acid donors | |
| CN105350329B (en) | A kind of polymer cation modifying agent for ramie fabric and preparation method and application method | |
| CN116790132A (en) | Water-soluble bisacryloyl bromamine acid dye, and synthetic method and application thereof | |
| CN116731531A (en) | Water-soluble diacryloyl gamma acid dye and synthesis method and application thereof | |
| CN107501988B (en) | Preparation method of solvent red 195 | |
| CN111233698A (en) | Polymerizable asymmetric azobenzene and preparation method thereof | |
| CN114874112B (en) | Surface active monomer containing sodium sulfonate group, and preparation method and application thereof | |
| US6222067B1 (en) | Alkylated diaminobenzene sulfonic acids | |
| CN104649940A (en) | Acrylamide monomer and its preparation method and use | |
| CN117431054B (en) | High-temperature iron ion stabilizer for acidizing fracturing fluid and preparation method thereof | |
| CN110878176B (en) | Reactive dye compound and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |