CN112209897A - Cationic direct dye compound and preparation method thereof - Google Patents
Cationic direct dye compound and preparation method thereof Download PDFInfo
- Publication number
- CN112209897A CN112209897A CN201910622917.8A CN201910622917A CN112209897A CN 112209897 A CN112209897 A CN 112209897A CN 201910622917 A CN201910622917 A CN 201910622917A CN 112209897 A CN112209897 A CN 112209897A
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- Prior art keywords
- direct dye
- cationic direct
- dye compound
- acid
- compound
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 39
- 125000002091 cationic group Chemical group 0.000 title claims abstract description 34
- 239000000982 direct dye Substances 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 239000000975 dye Substances 0.000 claims abstract description 16
- 238000004043 dyeing Methods 0.000 claims abstract description 9
- 239000000835 fiber Substances 0.000 claims abstract description 8
- 239000004677 Nylon Substances 0.000 claims abstract description 6
- 229920001778 nylon Polymers 0.000 claims abstract description 6
- 229920002239 polyacrylonitrile Polymers 0.000 claims abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 29
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- 238000006482 condensation reaction Methods 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 5
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 150000007519 polyprotic acids Polymers 0.000 claims description 4
- 150000005837 radical ions Chemical class 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 239000004310 lactic acid Substances 0.000 claims description 3
- 235000014655 lactic acid Nutrition 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 2
- 235000011054 acetic acid Nutrition 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- 235000011007 phosphoric acid Nutrition 0.000 claims description 2
- 239000006260 foam Substances 0.000 claims 2
- 102000004169 proteins and genes Human genes 0.000 claims 2
- 108090000623 proteins and genes Proteins 0.000 claims 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 229920000728 polyester Polymers 0.000 claims 1
- 229920004933 Terylene® Polymers 0.000 abstract description 5
- 238000004040 coloring Methods 0.000 abstract description 5
- 239000005020 polyethylene terephthalate Substances 0.000 abstract description 5
- 238000006243 chemical reaction Methods 0.000 description 18
- 238000010992 reflux Methods 0.000 description 13
- 238000003756 stirring Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 7
- 238000001816 cooling Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000012065 filter cake Substances 0.000 description 5
- 238000000227 grinding Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000000981 basic dye Substances 0.000 description 2
- 229920001131 Pulp (paper) Polymers 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- -1 sulfonate radical Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
- C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
-
- 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
- C09B57/00—Other synthetic dyes of known constitution
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
- Coloring (AREA)
Abstract
The invention discloses a cationic direct dye compound and a preparation method thereof. The structural formula is as follows:
Description
Technical Field
The invention relates to the technical field of direct dyes, in particular to a cationic direct dye compound and a preparation method thereof.
Background
The cationic direct dye is a new dye variety suitable for the paper industry, the molecular structure has a long plane molecular structure as the direct dye, and the cationic group in the basic dye can be used for replacing ions such as a sulfonate radical combined in the direct dye molecule, so that the cationic direct dye has the characteristics of the direct dye and the basic dye at the same time: cationic groups in the molecular structure can generate salt bond combination with anions in paper pulp, the dyeing degree of the dye is improved, and the long plane structure in the molecules can endow the dye with better fastness performance, so that more excellent application performance can be obtained.
CN101280120B proposes that cationic direct dyes can be used for dyeing both paper and fiber fabrics, and have excellent properties. The invention continues to expand the molecular structure range on the basis of the cationic direct dye, and the screened dye compound with a novel molecular structure also has the excellent performance, thereby making a new contribution to the development of cationic direct dyes.
Disclosure of Invention
The first aspect of the technical problem to be solved by the present invention is to further expand the molecular structure range of cationic direct dye compounds. The cationic direct dye can be used for coloring paper, can also be used for dyeing polyacrylonitrile fibers, modified terylene and cationic dyeable nylon, and has higher dyeing rate and excellent fastness performance.
The second aspect of the technical problem to be solved by the present invention is a method for preparing the above cationic direct dye compound.
The cationic direct dye compound as the first aspect of the present invention has the following chemical structural formula (i):
in the formula
R1、R2The method comprises the following steps: -H, -CH3、-CH2CH3、-CH2CH2CH3、-CH(CH3)2Etc. R1、R2May be the same or different. (ii) a
R3The method comprises the following steps: -CH3、-CH2CH3、-CH2CH2CH3、-CH(CH3)2、-CH2CH2CONH2、-CH(CH3)CH2CH2CONH2、-CH2C6H5Etc.;
R4、R5、R6、R7、R8the method comprises the following steps: -H, -CH3、-CH2CH3、-OCH3、-OCH2CH3、-COOCH3、-COOCH2CH3、-F、-Cl、-Br、-CN、-NO2Etc. R4、R5、R6、R7、R8May be the same or different and at least one group is alkyl or hydrogen;
n is a natural number of 1 to 4, preferably 1 or 2.
The mono-, di-or polybasic acid radicals are preferably Cl-, Br-, I-or H-radicals2PO4ˉ、CH3COO-, oxalate, lactic acid. More preferably H2PO4ˉ、CH3COOˉ。
The cationic direct dye compound of the above chemical structural formula (i) as the second aspect of the present invention can be prepared by the following method: the compound with the chemical structure general formula (II),
with a compound of the general formula (III),
adding the mixture into a specific solvent to carry out condensation reaction in the presence of acid to obtain the product; the reaction temperature is 40-80 ℃, wherein the molar ratio of the compound of the chemical structural general formula (II) to the compound of the chemical structural general formula (III) is 1: 1.02-1: 1.10.
The organic solvent is preferably an alcohol solvent.
The acid is an inorganic acid or an organic acid.
The condensation reaction temperature is 20-140 ℃, and preferably 40-80 ℃.
The molar ratio of the compound of the general chemical structure formula (II) to the compound of the general chemical structure formula (III) is 1: 1.02-1: 1.10.
The cationic direct dye compound is used for dyeing paper, polyacrylonitrile fiber, modified terylene and cationic dyeable nylon, and is used alone or mixed with similar dyes.
The invention has the characteristics that the product is simple to prepare, the condensation reaction is directly carried out, the obtained dye has wide application, the dyeing rate of the dyed paper is very high, the dye can be used for coloring the bleached paper and the non-bleached paper, and the dyed paper presents bright color light, can also be used for coloring the dyed fibers of polyacrylonitrile, modified terylene and cation dyeable nylon, and can be mixed with the similar dye.
Detailed Description
The technical scheme of the invention is further illustrated by the following specific embodiments, and the cationic direct dye compound has the following chemical structural general formula (I):
in the general formula:
R1、R2is-H, -CH3、-CH2CH3、-CH2CH2CH3or-CH (CH)3)2；
R3is-CH3、-CH2CH3、-CH2CH2CH3、-CH(CH3)2、-CH2CH2CONH2、-CH(CH3)CH2CH2CONH2 or-CH2C6H5；
R4、R5、R6、R7、R8is-H, -CH3、-CH2CH3、-OCH3、-OCH2CH3、-COOCH3、-COOCH2CH3-F, -Cl, -Br, -CN or-NO2；
n is a natural number of 1 to 4.
R1、R2The groups may be the same or different.
R4、R5、R6、R7、R8The radicals are identical or different and at least one radical is alkyl or hydrogen.
The said one-, two-and multi-acid radical ions are Cl-, Br-, I-and H-2PO4ˉ、CH3COO-, oxalate or lactate.
The preparation method comprises the step of mixing the compound with the chemical structural formula (II)
With compounds of the general formula (III)
Adding into a specific organic solvent, and performing condensation reaction in the presence of acid, wherein the solvent is one of ethanol, isopropanol and n-butanol, and the acid is one of formic acid, acetic acid, lactic acid, phosphoric acid and glycolic acid.
The condensation reaction temperature is 20-140 ℃, and preferably 40-80 ℃.
The molar ratio of the compound of the general chemical structure formula (II) to the compound of the general chemical structure formula (III) is 1: 1.02-1: 1.10.
The cationic direct dye compound is used for dyeing paper, polyacrylonitrile fiber, modified terylene and cationic dyeable nylon, and is used alone or mixed with similar dyes.
It is to be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the technical features of the invention.
Example 1
80g of ethanol and 4.9g of phosphoric acid are added to a reaction flask equipped with a stirrer and a reflux condenser, and 12.14g (0.05mol) of phosphoric acid are slowly added after stirring is started
And 8.39(0.051mol)
Stirring and dissolving to obtain a homogeneous phase reaction solution, rapidly heating to reflux (75-78 ℃), keeping a reflux state, reacting for 5 hours, distilling to remove solvent ethanol, cooling to room temperature (20-25 ℃), adding a proper amount of water to filter and wash a product obtained by the reaction, and finally drying and powdering an obtained filter cake to obtain a dye compound with the following chemical structure:
example 2
80g of ethanol and 3.5g of acetic acid are added into a reaction flask provided with a stirring and condensing reflux device, and 12.14g (0.05mol) of ethanol and acetic acid are slowly added after stirring is started
And 8.39(0.051mol)
Stirring and dissolving to obtain a homogeneous phase reaction solution, rapidly heating to reflux (75-78 ℃), keeping a reflux state, reacting for 5 hours, distilling to remove solvent ethanol, cooling to room temperature (20-25 ℃), adding a proper amount of water to filter and wash a product obtained by the reaction, and finally drying and powdering an obtained filter cake to obtain a dye compound with the following chemical structure:
example 3
80g of ethanol and 4.9g of phosphoric acid are added to a reaction flask equipped with a stirrer and a reflux condenser, and 12.14g (0.05mol) of phosphoric acid are slowly added after stirring is started
And 8.97(0.051mol)
Stirring and dissolving to obtain a homogeneous phase reaction solution, rapidly heating to reflux (75-78 ℃), keeping a reflux state, reacting for 5 hours, distilling to remove solvent ethanol, cooling to room temperature (20-25 ℃), adding a proper amount of water to filter and wash a product obtained by the reaction, and finally drying and powdering an obtained filter cake to obtain a dye compound with the following chemical structure:
example 4
80g of ethanol and 4.9g of phosphoric acid are added into a reaction flask provided with a stirring and condensing reflux device, and 18.86g (0.05mol) of ethanol and phosphoric acid are slowly added after stirring is started
And 8.39g (0.051mol)
Stirring and dissolving to obtain a homogeneous phase reaction solution, rapidly heating to reflux (75-78 ℃), keeping a reflux state, reacting for 5 hours, distilling to remove solvent ethanol, cooling to room temperature (20-25 ℃), adding a proper amount of water to filter and wash a product obtained by the reaction, and finally drying and powdering an obtained filter cake to obtain a dye compound with the following chemical structure:
example 5
80g of ethanol and 4.9g of phosphoric acid are added to a reaction flask equipped with a stirrer and a reflux condenser, and 12.14g (0.05mol) of phosphoric acid are slowly added after stirring is started
And 10.28(0.052mol)
Stirring and dissolving to obtain a homogeneous phase reaction solution, rapidly heating to 40-45 ℃, carrying out heat preservation reaction at 40-45 ℃ for 24 hours, carrying out reduced pressure distillation after the reaction is finished to remove the solvent ethanol, cooling to room temperature (20-25 ℃), adding a proper amount of water to filter and wash a product obtained by the reaction, and finally drying and powdering the obtained filter cake to obtain a dye compound with the following chemical structure:
finally, the above embodiments are only for illustrating the technical solutions of the present invention and not for limiting, although the present invention has been described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that modifications or equivalent substitutions may be made to the technical solutions of the present invention without departing from the spirit and scope of the technical solutions of the present invention, and all of them should be covered in the claims of the present invention.
Claims (8)
1. A cationic direct dye compound having the following general chemical structure formula (i):
in the general formula:
R1、R2is-H, -CH3、-CH2CH3、-CH2CH2CH3or-CH (CH)3)2；
R3is-CH3、-CH2CH3、-CH2CH2CH3、-CH(CH3)2、-CH2CH2CONH2、-CH(CH3)CH2CH2CONH2 or-CH2C6H5；
R4、R5、R6、R7、R8is-H, -CH3、-CH2CH3、-OCH3、-OCH2CH3、-COOCH3、-COOCH2CH3-F, -Cl, -Br, -CN or-NO2；
n is a natural number of 1 to 4.
2. The cationic direct dye compound of claim 1, wherein R is1、R2The groups may be the same or different.
3. The non-fluorine-containing non-protein foam fire extinguishing agent according to claim 1, wherein R is4、R5、R6、R7、R8The radicals are identical or different and at least one radical is alkyl or hydrogen.
4. The non-protein, fluorine-free fire foam of claim 1, wherein said mono-, di-and poly-acidic ions are Cl-, Br-, I-, H-, or2PO4ˉ、CH3COO-, oxalate or lactate.
5. The preparation method of the cationic direct dye compound is characterized in that the compound with the chemical structure general formula (II)
With compounds of the general formula (III)
Adding into a specific organic solvent, and performing condensation reaction in the presence of acid, wherein the solvent is one of ethanol, isopropanol and n-butanol, and the acid is one of formic acid, acetic acid, lactic acid, phosphoric acid and glycolic acid.
6. A method of preparing a cationic direct dye compound according to claim 5, wherein the condensation reaction temperature is 20 to 140 ℃, preferably 40 to 80 ℃.
7. The method for preparing a cationic direct dye compound according to claim 5, wherein the molar ratio of the compound of the general chemical structural formula (II) to the compound of the general chemical structural formula (III) is 1:1.02 to 1: 1.10.
8. The cationic direct dye compound of claim 1, wherein the cationic direct dye compound is used for dyeing paper, polyacrylonitrile fiber, modified polyester fiber, and cationic dyeable nylon, and the cationic direct dye compound is used alone or in combination with similar dyes.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910622917.8A CN112209897A (en) | 2019-07-11 | 2019-07-11 | Cationic direct dye compound and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910622917.8A CN112209897A (en) | 2019-07-11 | 2019-07-11 | Cationic direct dye compound and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN112209897A true CN112209897A (en) | 2021-01-12 |
Family
ID=74048711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910622917.8A Pending CN112209897A (en) | 2019-07-11 | 2019-07-11 | Cationic direct dye compound and preparation method thereof |
Country Status (1)
| Country | Link |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101245195A (en) * | 2008-03-14 | 2008-08-20 | 上海富圆染化有限公司 | Novel heterocycle azo cationic dye and manufacture method thereof |
| CN101280120A (en) * | 2008-02-22 | 2008-10-08 | 上海汇友精密化学品有限公司 | Cationic type direct dye and preparation thereof |
| CN101298521A (en) * | 2007-04-30 | 2008-11-05 | 上海汇友精密化学品有限公司 | Liquid cation dye and preparation thereof |
| CN110387141A (en) * | 2019-07-10 | 2019-10-29 | 东华大学 | A kind of dye matrix is azo cationic reactive dye and its preparation and the application of benzothiazoles |
-
2019
- 2019-07-11 CN CN201910622917.8A patent/CN112209897A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101298521A (en) * | 2007-04-30 | 2008-11-05 | 上海汇友精密化学品有限公司 | Liquid cation dye and preparation thereof |
| CN101280120A (en) * | 2008-02-22 | 2008-10-08 | 上海汇友精密化学品有限公司 | Cationic type direct dye and preparation thereof |
| CN101245195A (en) * | 2008-03-14 | 2008-08-20 | 上海富圆染化有限公司 | Novel heterocycle azo cationic dye and manufacture method thereof |
| CN110387141A (en) * | 2019-07-10 | 2019-10-29 | 东华大学 | A kind of dye matrix is azo cationic reactive dye and its preparation and the application of benzothiazoles |
Non-Patent Citations (1)
| Title |
|---|
| ANDRII V. KULINICH ET AL.: "Structure and redox properties of polymethine dyes: Electrochemical and DFT/TDDFT Study", 《DYES AND PIGMENTS》 * |
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Application publication date: 20210112 |
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