CN109879770B - Compound and preparation method and application thereof - Google Patents

Compound and preparation method and application thereof Download PDF

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CN109879770B
CN109879770B CN201910326452.1A CN201910326452A CN109879770B CN 109879770 B CN109879770 B CN 109879770B CN 201910326452 A CN201910326452 A CN 201910326452A CN 109879770 B CN109879770 B CN 109879770B
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hydrogen
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CN109879770A (en
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童国林
史蕊
李寿椿
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Nanjing Forestry University
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Nanjing Forestry University
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Abstract

The invention provides a compound and a preparation method and application thereof. A compound having the structure of formula (I):
Figure DDA0002036349550000011
wherein R is1、R2、R3、R4And R5At least one of which is amino and the others are independently selected from H, halogen, heteroatom substituted or unsubstituted C1‑20A hydrocarbyl group. The compound has an active group-COF, is easy to react with active groups (hydroxyl, amino and the like) on the surface of cellulose, and is not easy to hydrolyze, so that the prepared azo dye has strong stability in water and strong dyeing capability.

Description

Compound and preparation method and application thereof
Technical Field
The invention relates to the field of organic synthesis, in particular to a compound and a preparation method and application thereof.
Background
Introduction of cyanuric chloride and other active groups into aromatic compound molecules is one of the important methods for preparing dye intermediates in dye industry. The dye synthesized by the dye intermediate has the advantages that the reactive group in the molecular structure can react with the hydroxyl or the amino on the fiber to form covalent bonds such as C-O or C-N, and the like, so that the dye molecules are firmly bonded on the fabric. Can be widely applied to dyeing in the fields of textile, papermaking, leather and the like.
However, reactive dyes synthesized by using cyanuric chloride as a dye intermediate often have the problems of low fixation rate, easy hydrolysis, difficult wastewater treatment and the like. The kind and performance of the intermediate compound seriously affect the performance and index of the subsequent product. Therefore, the method has important significance for expanding the types of intermediates with excellent activity.
In view of the above, the present invention is particularly proposed.
Disclosure of Invention
The first object of the present invention is to provide a compound having a reactive group-COF, which is easily reacted with a reactive group (hydroxyl group, amino group, etc.) on the surface of cellulose and is not easily hydrolyzed, and thus the azo dye prepared therefrom has a strong stability in water and a strong dyeing ability.
The second purpose of the present invention is to provide the use of the above compounds, mainly in the field of dyes, which can be diazotized to couple with different couplers to obtain different types of dyes.
The third purpose of the invention is to provide a preparation method of the compound, which has simple synthetic route, simple reaction and less by-products.
In order to solve the technical problems, the invention provides the following technical scheme:
a compound having the structure of formula (I):
Figure BDA0002036349530000021
wherein R is1、R2、R3、R4And R5At least one of which is amino and the others are independently selected from H, halogen, heteroatom substituted or unsubstituted C1-20A hydrocarbyl group;
preferably, the heteroatom is substituted C1-20The hydrocarbon radical being C1-20Alkoxy or C1-20An alkylthio group.
The compound has the structure that the-COF and the amino can be in ortho-position, meta-position or para-position.
The compound (I) having a diazotized amino group, more importantly containing a reactive group-COF capable of reacting with the fiber, -COF as reactive group bound to the cellulose, has the following advantages:
1. has strong binding ability, i.e., F is easy to leave, and the following reaction (formula (I)) occurs,
Figure BDA0002036349530000022
Cell-OH represents cellulose;
2. f has strong non-metal property and strong stability of combination with hydrogen after leaving (namely, the stability of hydrogen fluoride is strong), so that the compound containing the active group is easier to combine with the fiber, the reaction is carried out in the forward direction, and the competitive property of the reaction formula (I) is stronger compared with the hydrolysis reaction;
3. the-COF in the compound is used as a bridge between the dye and the fiber, and the molecular weight is low (47), so that the proportion of easily hydrolyzed components in the reactive dye is low, the dye consumption can be reduced, and the reactivity of the dye can be improved;
4. the compound is an intermediate with excellent activity, and can be used for preparing active dye, medicinal products, etc. with the characteristics of difficult hydrolysis and easy combination with fiber, protein, etc.
In the present invention, R1、R2、R3、R4And R5The halogen selected may be fluorine, chlorine, bromine or iodine; c1-20The hydrocarbon group may be C1-20Alkyl radical, C1-20Alkylene or C1-20Aryl radicals, or hetero-atom substituted C1-20Alkyl radical, C1-20Alkylene or C1-20An aromatic hydrocarbon group; c1-20The hydrocarbyl groups may be straight or branched chain or cyclic hydrocarbyl groups.
C1-20A hydrocarbyl group such as methyl, ethyl, methylmethylene, propyl, isopropyl, butyl or its isomer, pentyl or its isomer, hexyl or its isomer, nonyl or its isomer, decyl or its isomer, eicosyl or its isomer, vinyl or its isomer, methyl, ethyl, propyl, isobutyl or its isomer, hexyl or its isomer, nonyl or its isomer, decyl or its isomer, or a salt thereof,Propenyl or its isomer, butenyl or its isomer, pentenyl or its isomer, hexenyl or its isomer, eicosenyl or its isomer, benzyl or its isomer, phenylpropyl or its isomer, phenylbutyl or its isomer, naphthylmethyl or its isomer, or heteroatom substitution of the above hydrocarbon groups, including N, S, O, P, etc.
The present invention further optimizes each substituent in the general formula as follows.
Preferably, in some embodiments of the invention, R1、R2、R3、R4And R5At least one of which is amino and the others are independently selected from H, halogen, C1-10Hydrocarbyl or heteroatom substituted C1-10A hydrocarbyl group.
Preferably, in some embodiments of the present invention,
R1is amino;
R2is hydrogen, halogen, C1-5Hydrocarbyl or heteroatom substituted C1-5A hydrocarbyl group;
R3is hydrogen, halogen, C1-5Hydrocarbyl or heteroatom substituted C1-5A hydrocarbyl group;
R4is hydrogen, halogen, C1-3Hydrocarbyl or heteroatom substituted C1-3A hydrocarbyl group;
R5is hydrogen, halogen, C1-3Hydrocarbyl or heteroatom substituted C1-3A hydrocarbyl group.
Preferably, in some embodiments of the present invention,
R1is hydrogen, halogen, C1-3Hydrocarbyl or heteroatom substituted C1-3A hydrocarbyl group;
R2is amino;
R3is hydrogen, halogen, C1-3Hydrocarbyl or heteroatom substituted C1-3A hydrocarbyl group;
R4is hydrogen, halogen, C1-3Hydrocarbyl or heteroatom substituted C1-5A hydrocarbyl group;
R5is hydrogen, halogen, C1-5Hydrocarbyl or heteroatom substituted C1-5A hydrocarbyl group.
Preferably, in some embodiments of the present invention,
R1is hydrogen, halogen, C1-3Hydrocarbyl or heteroatom substituted C1-5A hydrocarbyl group;
R2is hydrogen, halogen, C1-3Hydrocarbyl or heteroatom substituted C1-3A hydrocarbyl group;
R3is amino;
R4is hydrogen, halogen, C1-3Hydrocarbyl or heteroatom substituted C1-3A hydrocarbyl group;
R5is hydrogen, halogen, C1-5Hydrocarbyl or heteroatom substituted C1-5A hydrocarbyl group.
Preferably, in some embodiments of the invention, the compound of formula (I) is one of the following:
Figure BDA0002036349530000041
the compound (I) provided by the invention is mainly synthesized by three steps of reactions, and the route is as follows:
comprises the following steps:
a. subjecting the compound of formula (II) to a chlorination reaction to obtain a compound of formula (III);
Figure BDA0002036349530000051
wherein R is1’、R2’、R3’、R4' and R5' at least one of which is an amido or alkoxycarbonylamino group, the remainder being independently selected from H, halogen, hydrocarbyl or heteroatom-substituted hydrocarbyl;
b. reacting a compound of formula (III) with a fluorinating agent to give a compound of formula (IV);
Figure BDA0002036349530000052
c. removing the acyl group of the amide group or the alkoxycarbonyl group of the alkoxycarbonylamino group from the compound of the general formula (IV) to obtain the compound of the general formula (I).
Wherein R of the general formula (II)1’、R2’、R3’、R4' and R5' respectively correspond to R in the general formula (I)1、R2、R3、R4And R5The difference is only that the amino group in the latter is replaced by acyl or alkoxycarbonyl amino for amido, namely, the amino group is protected by the raw material selected during synthesis.
Step a is to generate acyl chloride, and the chlorinating agent used can be one or more of phosphorus trichloride, phosphorus pentachloride and thionyl chloride;
said step b is a step of substituting chlorine in the acid chloride with a fluorinating agent, which may be an inorganic fluorinating agent or an organic fluorinating agent, such as NH4F、LiF、NaF、KF、CsF、AgF、SbF3、BrF3、MnF3、CuF、(CH3)4NF and its acid salt or (C)4H9)4NF and one or more of its acid salts.
In step c, when the acyl group of the amide group is removed, the compound of formula (IV) is hydrolyzed in acid, wherein the hydrolysis temperature is preferably 20-200 ℃, and the hydrolysis time is preferably 1-48 h.
In step c, the compound of the general formula (IV) is subjected to catalytic hydrogenolysis, acid cleavage or reduction (Na/NH) when the alkoxycarbonyl group of the alkoxycarbonylamino group is removed3(liquid) as a reducing agent). Wherein, H is used in the catalytic hydrogenolysis2Or other hydrogen donors, generally hydrogenated at normal temperature and normal pressure. Acid cleavage or reduction methods are more suitable when groups sensitive to catalytic hydrogenolysis or deactivating the catalyst are present in the molecule. Meanwhile, in order to avoid the production of by-products, the acid used for the acidolysis cleavage is preferably HBr or the like.
The three reactions except the compound (II) do not need other complex organic matters, the reaction conditions are simple, and the by-products are high, so that the synthesis efficiency and the yield of the compound (I) are greatly improved.
In summary, compared with the prior art, the invention achieves the following technical effects:
(1) the compound synthesized by the invention can be used as an organic synthesis intermediate, mainly used in the dye industry, and the synthesized organic matter has the characteristic of being easy to combine with-OH-containing compounds such as fibers and the like and not easy to hydrolyze due to the existence of acyl fluoride groups;
(2) the synthesis method has few byproducts and high yield of the target product.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, and it is obvious that the drawings in the following description are some embodiments of the present invention, and other drawings can be obtained by those skilled in the art without creative efforts.
FIG. 1 is a nuclear magnetic spectrum F of compound I synthesized in example 1 of the present invention;
FIG. 2 is an infrared characterization map of compound I synthesized in example 1 of the present invention.
Detailed Description
The technical solutions of the present invention will be clearly and completely described below with reference to the accompanying drawings and the detailed description, but those skilled in the art will understand that the following described embodiments are some, not all, of the embodiments of the present invention, and are only used for illustrating the present invention, and should not be construed as limiting the scope of the present invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.
Example 1
Synthesis of Compound I
Figure BDA0002036349530000071
The synthetic route is as follows:
1)
Figure BDA0002036349530000072
2)
Figure BDA0002036349530000073
3)
Figure BDA0002036349530000074
1) 181kg of Compound A1, according to SOCl, are introduced into the reactor2SOCl was added to compound A1 in a molar ratio of 1:12Adding into a reaction kettle, heating to 125 + -5 deg.C, performing chloracylation reaction under stirring for 12 hr to obtain HCl and SO2Pumping the gas into a collecting tank by using a vacuum pump, and obtaining a compound B1 after the reaction is finished;
2) adding the dried compound B1 into a reaction vessel, heating to 75 +/-5 ℃, adding NaF pre-dissolved in water into the reaction vessel, reacting for 4-5h at 75 +/-5 ℃, and drying a product compound C1 after the reaction is finished; wherein the molar ratio of the compound B1 to NaF is 1: 2.5;
3) adding the compound C1 obtained in the step 2) into a reaction container, adding a certain amount of HCl solution into the reaction container to dissolve the compound C1, stirring for reaction, wherein the stirring speed is 1500rpm, the reaction temperature is 80-135 ℃, the embodiment is 90-100 ℃, when the reaction is carried out until no precipitate exists, centrifuging the reaction liquid to collect supernatant, titrating the collected supernatant with alkali, and stopping the reaction if a large amount of target products are produced by titration.
134.8kg of compound I was prepared by the above procedure, with a yield of 97% of compound I.
The nuclear magnetic spectrum F and the infrared spectrum of the compound I are respectively shown in figures 1 and 2.
The structures of the following examples are also structurally characterized by nuclear magnetic spectrum F and infrared spectrum, which are not described in detail below.
Example 2
Synthesis of Compound II
Figure BDA0002036349530000081
The synthetic route is as follows:
1)
Figure BDA0002036349530000082
2)
Figure BDA0002036349530000083
3)
Figure BDA0002036349530000084
1) 181kg of Compound A2, according to SOCl, are introduced into the reactor2SOCl was added to compound A2 in a molar ratio of 1:12Adding into a reaction kettle, heating to 125 + -5 deg.C, performing chloracylation reaction under stirring for 12 hr to obtain HCl and SO2Pumping the gas into a collecting tank by using a vacuum pump, and obtaining a compound B2 after the reaction is finished;
2) adding the dried compound B2 into a reaction vessel, heating to 75 +/-5 ℃, adding NaF pre-dissolved in water into the reaction vessel, reacting for 4-5h at 75 +/-5 ℃, and drying a product compound C2 after the reaction is finished; wherein the molar ratio of the compound B2 to NaF is 1: 2.5;
3) adding the compound C2 obtained in the step 2) into a reaction container, adding a certain amount of HCl solution into the reaction container to dissolve the compound C2, stirring for reaction at the stirring speed of 1500rpm and the reaction temperature of 90-100 ℃, taking reaction liquid for centrifugation and collecting supernatant when no precipitate is generated, titrating the collected supernatant with alkali, and stopping the reaction if a large amount of target products are generated by titration.
129.1kg of compound II was prepared by the above procedure, with a yield of 93% of compound I.
Example 3
Synthesis of Compound III
Figure BDA0002036349530000091
The synthetic route is as follows:
1)
Figure BDA0002036349530000101
2)
Figure BDA0002036349530000102
3)
Figure BDA0002036349530000103
1) 211kg of Compound A3, according to SOCl, are introduced into the reactor2SOCl was added to compound A3 in a molar ratio of 1:12Adding into a reaction kettle, heating to 125 + -5 deg.C, performing chloracylation reaction under stirring for 12 hr to obtain HCl and SO2Pumping the gas into a collecting tank by using a vacuum pump, and obtaining a compound B3 after the reaction is finished;
2) adding the dried compound B3 into a reaction vessel, heating to 75 +/-5 ℃, adding NaF pre-dissolved in water into the reaction vessel, reacting for 2-3h at 75 +/-5 ℃, and drying a product compound C3 after the reaction is finished; wherein the molar ratio of the compound B3 to NaF is 1: 1.8;
3) adding the compound C3 obtained in the step 2) into a reaction container, adding a certain amount of HCl solution into the reaction container to dissolve the compound C3, stirring for reaction at the stirring speed of 1500rpm and the reaction temperature of 90-100 ℃, taking reaction liquid for centrifugation and collecting supernatant when no precipitate is generated, titrating the collected supernatant with alkali, and stopping the reaction if a large amount of target products are generated by titration.
155.3kg of compound III was prepared by the above procedure with a yield of 91.8% of compound I.
Example 4
Synthesis of Compound IV
Figure BDA0002036349530000111
The synthetic route is as follows:
1)
Figure BDA0002036349530000112
2)
Figure BDA0002036349530000113
3)
Figure BDA0002036349530000114
1) 197kg of Compound A4, according to SOCl, were added to the reactor2SOCl was added to compound A4 in a molar ratio of 1:12Adding into a reaction kettle, heating to 125 + -5 deg.C, performing chloracylation reaction under stirring for 12 hr to obtain HCl and SO2Pumping the gas into a collecting tank by using a vacuum pump, and obtaining a compound B4 after the reaction is finished;
2) adding the dried compound B4 into a reaction vessel, heating to 75 +/-5 ℃, adding NaF pre-dissolved in water into the reaction vessel, reacting at 75 +/-5 ℃ for 0.5-1h, and drying a product compound C4 after the reaction is finished; wherein the molar ratio of the compound B4 to NaF is 1: 1.2;
3) adding the compound C4 obtained in the step 2) into a reaction container, adding a certain amount of HCl solution into the reaction container to dissolve the compound C4, stirring for reaction at the stirring speed of 1500rpm and the reaction temperature of 90-100 ℃, taking reaction liquid for centrifugation and collecting supernatant when no precipitate is generated, titrating the collected supernatant with alkali, and stopping the reaction if a large amount of target products are generated by titration.
150.2kg of compound IV was prepared by the above procedure with a yield of compound I of 95.7%.
Example 5
Synthesis of Compound V
Figure BDA0002036349530000121
The synthetic route is as follows:
1)
Figure BDA0002036349530000122
2)
Figure BDA0002036349530000123
3)
Figure BDA0002036349530000124
1) 459kg of Compound A5, according to SOCl, are placed in the reactor2SOCl was added to compound A5 in a molar ratio of 1:12Adding into a reaction kettle, heating to 125 + -5 deg.C, performing chloracylation reaction under stirring for 12 hr to obtain HCl and SO2Pumping the gas into a collecting tank by using a vacuum pump, and obtaining a compound B5 after the reaction is finished;
2) adding the dried compound B5 into a reaction vessel, heating to 75 +/-5 ℃, adding NaF pre-dissolved in water into the reaction vessel, reacting for 5-6h at 75 +/-5 ℃, and drying a product compound C5 after the reaction is finished; wherein the molar ratio of the compound B5 to NaF is 1: 2.8;
3) adding the compound C5 obtained in the step 2) into a reaction container, adding a certain amount of HCl solution into the reaction container to dissolve the compound C5, stirring for reaction at the stirring speed of 1500rpm and the reaction temperature of 90-100 ℃, taking reaction liquid for centrifugation and collecting supernatant when no precipitate is generated, titrating the collected supernatant with alkali, and stopping the reaction if a large amount of target products are generated by titration.
Compound V390 kg was prepared by the above procedure with a yield of compound I of 93.1%.
Example 6
From the intermediate of example 1
Figure BDA0002036349530000131
The red azo reactive dye can be obtained by diazotization coupling, and has a compound with the following formula:
Figure BDA0002036349530000132
the properties of the red reactive dye prepared in example 6 of the present invention are shown in table 1 below.
TABLE 1 fastness Properties of the dyes on fabrics
Figure BDA0002036349530000133
The experimental method comprises the following steps:
the fastness performance test of the dye on the fabric refers to the national standard: wherein, the determination of the rubbing fastness refers to GB/T3920-2008: color fastness to rubbing of textiles; the determination of the fastness to washing refers to GB/T5713 1997 in the test of textile color fastness to water color fastness; for the determination of the light fastness, reference is made to GB/T8426-1998: color fastness to light of textile test: daylight).
The specific dyeing method comprises the following steps: color number of 3-5%, alkali content Na2CO310g/L, 50g/L of electrolyte NaCl, 1:30 of bath ratio and 40 ℃. Dip-dyeing the treated fabric in a dyeing solution at room temperature for 20min, adding half of NaCl, dip-dyeing for 20min, heating to 40 deg.C, adding the other half of salt, further dyeing for 20min, and adding half of Na2CO3Dyeing for 30min, and adding the rest half amount of Na2CO3Dyeing for 30min and drying.
The fastness properties of the dyes on the fabric are determined with reference to the above criteria.
Finally, it should be noted that: the above embodiments are only used to illustrate the technical solution of the present invention, and not to limit the same; while the invention has been described in detail and with reference to the foregoing embodiments, it will be understood by those skilled in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some or all of the technical features may be equivalently replaced; and the modifications or the substitutions do not make the essence of the corresponding technical solutions depart from the scope of the technical solutions of the embodiments of the present invention.

Claims (10)

1. Use of a compound for the synthesis of a dye, characterized in that said compound is used as a dye intermediate;
the compounds have the general formula (I):
Figure FDA0003241904340000011
wherein R is1、R2、R3、R4And R5At least one of which is amino and the others are independently selected from H, halogen, heteroatom substituted or unsubstituted C1-20A hydrocarbyl group;
said heteroatom being substituted by C1-20The hydrocarbon radical being C1-20Alkoxy or C1-20An alkylthio group.
2. Use according to claim 1, characterized in that R1、R2、R3、R4And R5At least one of which is amino and the others are independently selected from H, halogen, C1-10Hydrocarbyl or heteroatom substituted C1-10A hydrocarbyl group.
3. Use according to claim 1,
R1is amino;
R2is hydrogen, halogen, C1-5Hydrocarbyl or heteroatom substituted C1-5A hydrocarbyl group;
R3is hydrogen, halogen, C1-5Hydrocarbyl or heteroatom substituted C1-5A hydrocarbyl group;
R4is hydrogen, halogen, C1-3Hydrocarbyl or heteroatom substituted C1-3A hydrocarbyl group;
R5is hydrogen, halogen, C1-3Hydrocarbyl or heteroatom substituted C1-3A hydrocarbyl group.
4. Use according to claim 1,
R1is hydrogen, halogen, C1-3Hydrocarbyl or heteroatom substituted C1-3A hydrocarbyl group;
R2is amino;
R3is hydrogen, halogen, C1-3Hydrocarbyl or heteroatom substituted C1-3A hydrocarbyl group;
R4is hydrogen, halogen, C1-3Hydrocarbyl or heteroatom substituted C1-5A hydrocarbyl group;
R5is hydrogen, halogen, C1-5Hydrocarbyl or heteroatom substituted C1-5A hydrocarbyl group.
5. Use according to claim 1,
R1is hydrogen, halogen, C1-3Hydrocarbyl or heteroatom substituted C1-5A hydrocarbyl group;
R2is hydrogen, halogen, C1-3Hydrocarbyl or heteroatom substituted C1-3A hydrocarbyl group;
R3is amino;
R4is hydrogen, halogen, C1-3Hydrocarbyl or heteroatom substituted C1-3A hydrocarbyl group;
R5is hydrogen, halogen, C1-5Hydrocarbyl or heteroatom substituted C1-5A hydrocarbyl group.
6. Use according to claim 1, characterized in that the compound of general formula (I) is one of the following:
Figure FDA0003241904340000021
7. use according to claim 1, characterized in that the preparation of said compound comprises the following steps:
a. subjecting the compound of formula (II) to a chlorination reaction to obtain a compound of formula (III);
Figure FDA0003241904340000022
wherein R is1’、R2’、R3’、R4' and R5' at least one of which is an amido or alkoxycarbonylamino group, the remainder being independently selected from H, halogen, hydrocarbyl or heteroatom-substituted hydrocarbyl;
b. reacting a compound of formula (III) with a fluorinating agent to give a compound of formula (IV);
Figure FDA0003241904340000023
c. removing the acyl group of the amide group or the alkoxycarbonyl group of the alkoxycarbonylamino group from the compound of the general formula (IV) to obtain the compound of the general formula (I).
8. The use according to claim 7, characterized in that the chlorinating agent used in the chlorination reaction in step a is one or more of phosphorus trichloride, phosphorus pentachloride, thionyl chloride, sulfuryl chloride, chlorine gas, hydrogen chloride and phosgene.
9. Use according to claim 7, wherein the fluorinating agent in step b is NH4F、LiF、NaF、KF、CsF、AgF、SbF3、BrF3、MnF3、CuF、(CH3)4NF and its acid salt or (C)4H9)4NF and one or more of its acid salts.
10. Use according to claim 7, wherein in step c, if the acyl group of the amide group is removed, the compound of formula (IV) is hydrolyzed in acid at a temperature of 20-200 ℃ for a time of 0.1-48 h;
in step c, the compound of the general formula (IV) is subjected to catalytic hydrogenolysis, acid cleavage or reduction when the alkoxycarbonyl group of the alkoxycarbonylamino group is removed.
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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103408961A (en) * 2013-05-31 2013-11-27 中国科学院福建物质结构研究所 Dye for supercritical carbon dioxide dying and preparation and application of dye

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103408961A (en) * 2013-05-31 2013-11-27 中国科学院福建物质结构研究所 Dye for supercritical carbon dioxide dying and preparation and application of dye

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
Dyeing of cotton fabric with reactive disperse dye contain acyl fluoride group in supercritical carbon dioxide;Jin-xin Lin等;《Dyes and Pigments》;20171231;第139卷;第566-574页 *
RN：1824354-23-5、1824319-39-2、1824315-87-8、1824102-98-8、1824099-75-3、39638-06-7、39638-05-6、824-74-8;Chemical Abstract RN;《STN on the Web REGISTRY数据库》;20151207;第RN：1824354-23-5、1824319-39-2、1824315-87-8、1824102-98-8、1824099-75-3、39638-06-7、39638-05-6、824-74-8页 *
Use of C,N-chelated di-n-butyltin(IV) fluoride for the synthesis of acyl fluorides, fluoroformates and fluorophosgene;Petr Švec等;《Tetrahedron Letters》;20081231;第49卷;第6320-6323页 *

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