CN101215245A - Monoazo compound containing diester and its preparation, application and dye composition - Google Patents
Monoazo compound containing diester and its preparation, application and dye composition Download PDFInfo
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- CN101215245A CN101215245A CNA2007100666188A CN200710066618A CN101215245A CN 101215245 A CN101215245 A CN 101215245A CN A2007100666188 A CNA2007100666188 A CN A2007100666188A CN 200710066618 A CN200710066618 A CN 200710066618A CN 101215245 A CN101215245 A CN 101215245A
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- acid esters
- monoazo compound
- dibasic acid
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- -1 Monoazo compound Chemical class 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- 239000000203 mixture Substances 0.000 title claims description 10
- 150000005690 diesters Chemical class 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- 239000000975 dye Substances 0.000 claims description 32
- 239000002253 acid Substances 0.000 claims description 23
- 150000002148 esters Chemical class 0.000 claims description 23
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- ODFJOVXVLFUVNQ-UHFFFAOYSA-N acetarsol Chemical group CC(=O)NC1=CC([As](O)(O)=O)=CC=C1O ODFJOVXVLFUVNQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000012954 diazonium Substances 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 150000002431 hydrogen Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 238000006193 diazotization reaction Methods 0.000 claims description 5
- 239000000986 disperse dye Substances 0.000 claims description 5
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical group CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 4
- 150000001989 diazonium salts Chemical class 0.000 claims description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 235000010288 sodium nitrite Nutrition 0.000 claims description 2
- 239000000835 fiber Substances 0.000 abstract description 8
- 238000005406 washing Methods 0.000 abstract description 6
- 229920000728 polyester Polymers 0.000 abstract description 4
- 239000007788 liquid Substances 0.000 abstract description 3
- 239000000178 monomer Substances 0.000 abstract description 3
- 229920002972 Acrylic fiber Polymers 0.000 abstract description 2
- 230000002209 hydrophobic effect Effects 0.000 abstract description 2
- 238000001694 spray drying Methods 0.000 abstract description 2
- 238000000859 sublimation Methods 0.000 abstract description 2
- 230000008022 sublimation Effects 0.000 abstract description 2
- 229920002301 cellulose acetate Polymers 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 238000004043 dyeing Methods 0.000 description 9
- 239000002131 composite material Substances 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 5
- 239000007859 condensation product Substances 0.000 description 4
- 230000006837 decompression Effects 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 238000009998 heat setting Methods 0.000 description 4
- 238000009413 insulation Methods 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 229920004934 Dacron® Polymers 0.000 description 2
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002535 acidifier Substances 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- 238000010009 beating Methods 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 2
- 235000019357 lignosulphonate Nutrition 0.000 description 2
- QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000001089 thermophoresis Methods 0.000 description 2
- MHXFWEJMQVIWDH-UHFFFAOYSA-N 1-amino-4-hydroxy-2-phenoxyanthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1OC1=CC=CC=C1 MHXFWEJMQVIWDH-UHFFFAOYSA-N 0.000 description 1
- KTHUKEZOIFYPEH-UHFFFAOYSA-N 1-benzylnaphthalene Chemical compound C=1C=CC2=CC=CC=C2C=1CC1=CC=CC=C1 KTHUKEZOIFYPEH-UHFFFAOYSA-N 0.000 description 1
- QEORVDCGZONWCJ-UHFFFAOYSA-N 2-[[4-[2-cyanoethyl(ethyl)amino]phenyl]diazenyl]-5-nitrobenzonitrile Chemical compound C1=CC(N(CCC#N)CC)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1C#N QEORVDCGZONWCJ-UHFFFAOYSA-N 0.000 description 1
- ROPYWXVRNREIQD-UHFFFAOYSA-N 2-[n-(2-cyanoethyl)-4-[(2,6-dichloro-4-nitrophenyl)diazenyl]anilino]ethyl acetate Chemical compound C1=CC(N(CCC#N)CCOC(=O)C)=CC=C1N=NC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl ROPYWXVRNREIQD-UHFFFAOYSA-N 0.000 description 1
- CULIYQPRUGMRRT-UHFFFAOYSA-N 2-chloro-n-[2-[(2-cyano-4-nitrophenyl)diazenyl]-5-(diethylamino)phenyl]acetamide Chemical compound ClCC(=O)NC1=CC(N(CC)CC)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1C#N CULIYQPRUGMRRT-UHFFFAOYSA-N 0.000 description 1
- VGKYEIFFSOPYEW-UHFFFAOYSA-N 2-methyl-4-[(4-phenyldiazenylphenyl)diazenyl]phenol Chemical compound Cc1cc(ccc1O)N=Nc1ccc(cc1)N=Nc1ccccc1 VGKYEIFFSOPYEW-UHFFFAOYSA-N 0.000 description 1
- WODGMMJHSAKKNF-UHFFFAOYSA-N 2-methylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(C)=CC=C21 WODGMMJHSAKKNF-UHFFFAOYSA-N 0.000 description 1
- SRDOTWUOTQTGAK-UHFFFAOYSA-N C=O.C1(=CC=CC2=CC=CC=C12)S(=O)(=O)OCC1=CC=CC=C1 Chemical compound C=O.C1(=CC=CC2=CC=CC=C12)S(=O)(=O)OCC1=CC=CC=C1 SRDOTWUOTQTGAK-UHFFFAOYSA-N 0.000 description 1
- FWLKPAWURKAQCA-UHFFFAOYSA-N CC(C(=O)N(C1=CC=CC=C1)OC)OC Chemical compound CC(C(=O)N(C1=CC=CC=C1)OC)OC FWLKPAWURKAQCA-UHFFFAOYSA-N 0.000 description 1
- VRYYKYXSPJPGTB-UHFFFAOYSA-N CCC(=O)C1=C(C=CC=C1N(OC)OC)C Chemical compound CCC(=O)C1=C(C=CC=C1N(OC)OC)C VRYYKYXSPJPGTB-UHFFFAOYSA-N 0.000 description 1
- BCEZIQLELBHUSU-UHFFFAOYSA-N CON(C1=C(C=CC=C1)C(=O)CC)OC Chemical compound CON(C1=C(C=CC=C1)C(=O)CC)OC BCEZIQLELBHUSU-UHFFFAOYSA-N 0.000 description 1
- 239000004218 Orcein Substances 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 229920004933 Terylene® Polymers 0.000 description 1
- 229920004935 Trevira® Polymers 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- ONTQJDKFANPPKK-UHFFFAOYSA-L chembl3185981 Chemical compound [Na+].[Na+].CC1=CC(C)=C(S([O-])(=O)=O)C=C1N=NC1=CC(S([O-])(=O)=O)=C(C=CC=C2)C2=C1O ONTQJDKFANPPKK-UHFFFAOYSA-L 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 238000004044 disperse dyeing Methods 0.000 description 1
- TUXJTJITXCHUEL-UHFFFAOYSA-N disperse red 11 Chemical compound C1=CC=C2C(=O)C3=C(N)C(OC)=CC(N)=C3C(=O)C2=C1 TUXJTJITXCHUEL-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- BMUXKUVOASOJKR-UHFFFAOYSA-N methyl 3-[4-[(2-chloro-4-nitrophenyl)diazenyl]-n-(2-cyanoethyl)anilino]propanoate Chemical compound C1=CC(N(CCC#N)CCC(=O)OC)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1Cl BMUXKUVOASOJKR-UHFFFAOYSA-N 0.000 description 1
- 239000001048 orange dye Substances 0.000 description 1
- 235000019248 orcein Nutrition 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Abstract
The invention provides a monoazo compound with di-ester whose structure is showed as formula (I), a preparation process, the application, and a dye compound which is composed of the dye monomer. The dye compound of the invention can be prepared into liquid state and emulsifiable paste state after being micronized, or powder or grain forms which are dried by spray drying to dye. The invention is suitable to coloration of hydrophobic fiber such as polyester fiber, cellulose acetate, acrylic fiber, polyester and blended yarn and the like, which has excellent dying properties such as bright color, light-resistant, washing, color fastness to sublimation, low costs and the like, and the invention is a product variety which is valuable and has potential application prospect.
Description
(1) technical field
The present invention relates to a kind of dye monomer--a kind of Monoazo compound that contains dibasic acid esters and preparation thereof and application, and the dye composite of forming by this dye monomer.
(2) background technology
In recent years, in dacron fabric such as Sportswear, Casual Wear, the automobile fabric etc. with stablely carrying out heat setting type and handle for guaranteeing that final dimension one is made peace after the disperse dyeing.Because heat setting temperature is higher, will be above 140 ℃, the thermophoresis reverse with when dyeing will take place in the dispersed dye of fibrous inside, the part dyestuff can migrate to fiber surface again, causes dyeing after decline such as the colour fastness of the fabric of heat setting type such as washing fastness, perspiration fastness and can be infected with adjacent subsides lining and go up or contaminate environment.
Facts have proved, in old dispersed dye, there is the heat-resisting transport property of quite a few kind relatively poor, can make the washing fastness variation of dyeing polyester fabric after the heat setting type processing or after arrangements such as softness, waterproof, dye species such as C.I. Disperse Red 54, C.I. disperse red 60, C.I. Disperse Red 73, C.I. Red-1 200 52, C.I. Red-1 200 53, C.I. Red 167 for example, for this reason, good dyestuff becomes the research and development focus to develop heat-resisting transport property, has done similar report in succession as patent US4029469, JP58-160356, DE0379872 etc.
(3) summary of the invention
For overcoming above-mentioned deficiency, it is good to the invention provides a kind of avidity, have remarkable wet colour fastness, high Chromaticity intensity and lifting force, good circulation ratio and to dye monomer--a kind of Monoazo compound and preparation and application that contains dibasic acid esters of the anti-metachromia of cellulosic fibre, and the dye composite of forming by this dye monomer.
For reaching goal of the invention the technical solution used in the present invention be:
A kind of Monoazo compound that contains dibasic acid esters, structure is suc as formula shown in (I):
In the formula (I):
N is 1 or 2;
R
1, R
2Independent separately is methyl or ethyl;
Y is hydrogen, hydroxyl, kharophen, C
1～C
4Alkyl or alkoxyl group;
D is the group shown in following formula (II) or the formula (III),
In formula (II), the formula (III):
X
1, X
2, X
3Independent separately is Cl or Br;
When D was the group of formula (II), Y was not hydrogen or C
1～C
4Alkyl.
Preferably, described compound is one of following:
The invention still further relates to a kind of described preparation method who contains the Monoazo compound of dibasic acid esters, described method is as follows:
(1) with the aniline shown in formula (IV) or the formula V under acidic conditions with diazo reagent
Carry out diazotization reaction, obtain the diazonium salt of described aniline;
X
1, X
2, X
3Independent separately is Cl or Br;
(2) diazonium salt that step (1) is obtained and the compound shown in the formula (VI) carry out coupled reaction, promptly get the described Monoazo compound that contains dibasic acid esters;
R
1, R
2Independent separately is methyl or ethyl;
Y is hydrogen, hydroxyl, kharophen, C
1～C
4Alkyl or alkoxyl group.
Described diazo reagent is a nitrosyl sulfuric acid solution, perhaps is the mixing solutions of hydrochloric acid or sulfuric acid and Sodium Nitrite.Described diazotization reaction is preferably carried out under-30 ℃～30 ℃.Described coupled reaction is preferably in the solution of PH≤2, carry out under 0～10 ℃.
The described Monoazo compound that contains dibasic acid esters can be used and prepare dispersed dye.
The invention still further relates to a kind of disperse dye composition, contain one or more structures suc as formula the Monoazo compound that contains dibasic acid esters shown in (I):
In the formula (I):
N is 1 or 2;
R
1, R
2Independent separately is methyl or ethyl;
Y is hydrogen, hydroxyl, kharophen, C
1～C
4Alkyl or alkoxyl group;
D is the group shown in following formula (II) or the formula (III),
In formula (II), the formula (III):
X
1, X
2, X
3Independent separately is Cl or Br;
When D was the group of formula (II), Y was not hydrogen or C
1～C
4Alkyl.
Preferably, described disperse dye composition by one of compound (I-1)～(I-12) or wherein two or more compound form.
Described dibasic acid esters structure and the trevira that contains the Monoazo compound of dibasic acid esters has good avidity because of there being structural similarity, make dyestuff in fiber capillary, move difficulty, be difficult for taking place thermophoresis, thereby have remarkable wet colour fastness, also have high Chromaticity intensity and lifting force simultaneously, well circulation ratio and the characteristics such as anti-metachromia of cellulosic fibre, in addition, dye the back with the heat alkali liquid washing, can make dibasic acid esters be hydrolyzed to carboxylic acid sodium salt, thus easily clean by the thermokalite washing.
When dye composite of the present invention is applied to dye; usually also must carry out the commercialization aftertreatment; be typically and synthesize the former dye filtering that obtains; adding usual auxiliaries, water and other wetting agents carries out pre-dispersed; carry out corpusculed with pulverizers such as sand mill or shredders; vacuum-drying or spraying drying then, usually, auxiliary agent is 0.8～5: 1 with the ratio of former dyestuff weight.Described auxiliary agent is dyestuff dispersion agent commonly used when composite, diffusant etc., comprise one of following or its several mixture arbitrarily: naphthalene sulfonic acidformaldehyde condensation product, the formaldehyde condensation products of alkyl naphthalene sulfonic acid, the benzyl naphthalene sulfonic formaldehyde condensation compound, sulfonated lignin etc., particularly, naphthalene sulfonic acidformaldehyde condensation product such as dispersing agent NNO, alkyl naphthalene sulfonic acid formaldehyde condensation products such as Dispersant MF (condensation compound of methyl naphthalene sulfonic acid and formaldehyde), benzyl naphthalenesulfonate formaldehyde condensation compound such as dispersing agent CNF etc., sulfonated lignin such as sodium lignosulfonate are (as commercial dispersants ReaX 83A, Reax 85A) etc.
The Monoazo compound that contains dibasic acid esters of the present invention can be each other be applied to dyeing with arbitrary proportion after composite, also can obtain dyestuff dark blue, black and is applied to dyeing with dyestuffs such as other dyestuff such as Disperse Red, DISPERSE ORANGE 30 200,63 DISPERSE Violet 63, DISPERSE YELLOW are composite.
Dye composite of the present invention, the liquid state after can corpusculed, emulsifiable paste attitude or with spray-drying process etc. carry out dried powdery, the particulate state state is supplied with dyeing.Be applicable to terylene, the vinegar fibre, acrylic fibers, the dyeing of hydrophobic fiber materials such as polyester and blending has remarkable dyeing behavior, and colour fastness excellences such as, anti-distillation gorgeous, fast light, washable as coloured light are with low cost, are rare, very promising kinds.
(4) embodiment
The present invention is described further below in conjunction with specific embodiment, but protection scope of the present invention is not limited in this:
Embodiment 1: the preparation of intermediate
In there-necked flask, add the 21.8g Metha Amino Phenon, 108g methyl acrylate and 25g acetic acid, the 5g Sodium Bromide, be heated to 90-95 ℃, behind the reaction 19h, under this temperature, decompression steams unnecessary methyl acrylate and acetic acid, be cooled to 30-35 ℃, get the 3-hydroxy-n, N-dimethoxy-ethyl-carbonyl aniline solution.
Embodiment 2: the preparation of intermediate
In there-necked flask, add the 24.6g Metha Amino Phenon, 120g methyl acrylate and 30g acetic acid, the 5g Sodium Bromide, be heated to 90-95 ℃, behind the reaction 19h, under this temperature, decompression steams unnecessary methyl acrylate and acetic acid, be cooled to 30-35 ℃, get 3-methoxyl group-N, N-dimethoxy-ethyl-carbonyl aniline solution.
Embodiment 3: the preparation of intermediate
In there-necked flask, add the 21.4g Metha Amino Phenon, 105g methyl acrylate and 25g acetic acid, the 5g Sodium Bromide, be heated to 90-95 ℃, behind the reaction 19h, under this temperature, decompression steams unnecessary methyl acrylate and acetic acid, be cooled to 30-35 ℃, get 3-methyl-N, N-dimethoxy-ethyl-carbonyl aniline solution.
Embodiment 4: the preparation of intermediate
In there-necked flask, add the 21.8g Metha Amino Phenon, 75g methyl chloroacetate and 28g yellow soda ash, the 5g Sodium Bromide is heated to 115-135 ℃, behind the reaction 5h, under this temperature, decompression steams unnecessary methyl chloroacetate, is cooled to 30-35 ℃, adds 150g acetic acid, get the 3-hydroxy-n, N-dimethoxy carbonyl monomethylaniline solution.
Embodiment 5: contain the preparation of the Monoazo compound of dibasic acid esters
In there-necked flask, add sulfuric acid (98%) 80g, 20% nitrosyl sulfuric acid 80g, stir 30-60min, 10～30 ℃ of controlled temperature, under agitation in 2 hours with 2 of 0.2mol (41.4 gram), 6-two chloro-4-N-methyl-p-nitroanilines (raw material 1) add in the above-mentioned there-necked flask, and insulation reaction is about 5 hours, and diazotization is finished.
Get the 3-hydroxy-n of preparation in the above-mentioned example 1, N-dimethoxy-ethyl-carbonyl aniline (raw material 2) solution, 10 ℃ of making beating down, controlled temperature adds a small amount of thionamic acid and emulsifying agent below 10 ℃, above-mentioned diazonium drop is added, time is controlled at about 2h, adds back insulation 2 hours, suction filtration, be washed to PH=6～7, can make the orchil compound of following formula (I-1).
Embodiment 6～9:
According to embodiment 5 described preparation methods, the component shown in raw material 1, the raw material 2 usefulness tables 1 is carried out the equimolar amount replacement, can make dye composition according to the invention.(annotating: used 3-acetylaminohydroxyphenylarsonic acid N, N-dimethoxy-ethyl-carbonyl aniline, N, N-dimethoxy-ethyl-carbonyl aniline, commercially available (Shaoxing county ten thousand logical dye chemical industry company limiteds))
Table 1
Embodiment 10:
Add the 40g vitriol oil in the there-necked flask, open stirring, be cooled to room temperature and slowly add the 15%50g nitrosyl sulfuric acid, adding the back stirred about 30 minutes, the raw material 3 that about 20 ℃, adds 0.2mol, i.e. the red basic 3GL (4-chloro-2-N-methyl-p-nitroaniline) of 34.5 grams, in the reinforced process controlled temperature below 20 ℃ approximately 1h add, added the back insulation reaction 1～2 hour, standby.
Get the raw material 2 of 0.2mol, the i.e. 3-hydroxy-ns of 56.26 grams, N-dimethoxy-ethyl-carbonyl aniline is 10 ℃ of down making beating, controlled temperature is below 10 ℃, add a small amount of thionamic acid and emulsifying agent, above-mentioned diazonium drop is added, the time is controlled at about 2h, add back insulation 2h, suction filtration is washed to PH=6～7, can make the orange dye compound of following formula (I-3).
Embodiment 11～16:
According to embodiment 10 described preparation methods, the component shown in raw material 1, the raw material 2 usefulness tables 2 is carried out the equimolar amount replacement, can make dye composition according to the invention.
Table 2
Embodiment 17: commercialization of dyes and dyeing procedure
Get each 20 gram of the Monoazo compound that contains dibasic acid esters in the example 5～16, add 25 gram Dispersant MFs respectively, 100 gram pure water grind evenly, and drying and dehydrating promptly gets corresponding commercial dye.
Respectively getting the above-mentioned commercial dye of 0.5 gram is dispersed in 500 ml waters, mix with 60 milliliters water after drawing 20 milliliters, transferring dye bath PH with acetic acid is 4.5-5, be warming up to 70 ℃, putting into 2 gram woven dacrons simultaneously dyes, in 30 minutes, be warmed up to 130 ℃, be incubated 40 minutes by 70 ℃, be cooled to begin below 90 ℃ the sampling.
Adopt that GB GB/T3921-1997, GB/T3920-1997, GB/T8427-1998, GB/T5718-1997, HG/T3399-2001 test respectively that it is water-fastly washed, rub resistance, sun-resistant, color fastness to sublimation and diffusion.Test result is as shown in table 3.
Table 3
| Embodiment | Color and luster | Water-fast washing | Rub resistance | Sun-resistant | Anti-distillation | Diffustivity |
| 5 | Red | 5 grades | 4～5 grades | 6～7 grades | 5 grades | 5 grades |
| 6 | Orange | 5 grades | 4～5 grades | 6～7 grades | 4～5 grades | 4～5 grades |
| 7 | Red | 4～5 grades | 4～5 grades | 6～7 grades | 4～5 grades | 4～5 grades |
| 8 | Palm fibre | 4～5 grades | 4～5 grades | 6～7 grades | 4～5 grades | 4～5 grades |
| 9 | Red | 5 grades | 4～5 grades | 6～7 grades | 4～5 grades | 4～5 grades |
| 10 | Orange | 5 grades | 4～5 grades | 6 grades | 5 grades | 5 grades |
| 11 | Orange | 5 grades | 4～5 grades | 6～7 grades | 4～5 grades | 4～5 grades |
| 12 | Orange | 5 grades | 4～5 grades | 6～7 grades | 4～5 grades | 4～5 grades |
| 13 | Orange | 4～5 grades | 4～5 grades | 6～7 grades | 4～5 grades | 4～5 grades |
| 14 | Orange | 4～5 grades | 4～5 grades | 6～7 grades | 4～5 grades | 4～5 grades |
| 15 | Orange | 4～5 grades | 4～5 grades | 6～7 grades | 4～5 grades | 4～5 grades |
| 16 | Orange | 4～5 grades | 4～5 grades | 6～7 grades | 4～5 grades | 4～5 grades |
Claims (9)
1. Monoazo compound that contains dibasic acid esters, structure is suc as formula shown in (I):
In the formula (I):
N is 1 or 2;
R
1, R
2Independent separately is methyl or ethyl;
Y is hydrogen, hydroxyl, kharophen, C
1～C
4Alkyl or alkoxyl group;
D is the group shown in following formula (II) or the formula (III),
In formula (II), the formula (III):
X
1, X
2, X
3Independent separately is Cl or Br;
When D was the group of formula (II), Y was not hydrogen or C
1～C
4Alkyl.
2. the Monoazo compound that contains dibasic acid esters as claimed in claim 2 is characterized in that described compound is one of following:
3. prepare the method that contains the Monoazo compound of dibasic acid esters as claimed in claim 1 or 2, described method is as follows:
(1) aniline shown in formula (IV) or the formula V is carried out diazotization reaction with diazo reagent under acidic conditions, obtain the diazonium salt of described aniline;
X
1, X
2, X
3Independent separately is Cl or Br;
(2) diazonium salt that step (1) is obtained and the compound shown in the formula (VI) carry out coupled reaction, promptly get the described Monoazo compound that contains dibasic acid esters;
R
1, R
2Independent separately is methyl or ethyl;
Y is hydrogen, hydroxyl, kharophen, C
1～C
4Alkyl or alkoxyl group.
4. the preparation method who contains the Monoazo compound of dibasic acid esters as claimed in claim 3 is characterized in that described diazo reagent is a nitrosyl sulfuric acid solution, perhaps is the mixing solutions of hydrochloric acid or sulfuric acid and Sodium Nitrite.
5. the preparation method who contains the Monoazo compound of dibasic acid esters as claimed in claim 3 is characterized in that described diazotization reaction carries out under-30 ℃～30 ℃.
6. the preparation method who contains the Monoazo compound of dibasic acid esters as claimed in claim 3 is characterized in that described coupled reaction carries out in the solution of PH≤2, under 0～10 ℃.
7. the application of Monoazo compound in the preparation dispersed dye that contains dibasic acid esters as claimed in claim 1.
8. disperse dye composition, contain one or more structures suc as formula the Monoazo compound that contains dibasic acid esters shown in (I):
In the formula (I):
N is 1 or 2;
R
1, R
2Independent separately is methyl or ethyl;
Y is hydrogen, hydroxyl, kharophen, C
1～C
4Alkyl or alkoxyl group;
D is the group shown in following formula (II) or the formula (III),
In formula (II), the formula (III):
X
1, X
2, X
3Independent separately is Cl or Br;
When D was the group of formula (II), Y was not hydrogen or C
1～C
4Alkyl.
9. disperse dye composition as claimed in claim 8, it is characterized in that described disperse dye composition by one of following or wherein two or more compound form:
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|---|---|---|---|
| CN2007100666188A CN101215245B (en) | 2007-01-05 | 2007-01-05 | Monoazo compound containing diester and its preparation, application and dye composition |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2007100666188A CN101215245B (en) | 2007-01-05 | 2007-01-05 | Monoazo compound containing diester and its preparation, application and dye composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101215245A true CN101215245A (en) | 2008-07-09 |
| CN101215245B CN101215245B (en) | 2011-11-30 |
Family
ID=39621765
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2007100666188A Active CN101215245B (en) | 2007-01-05 | 2007-01-05 | Monoazo compound containing diester and its preparation, application and dye composition |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102516797A (en) * | 2011-10-31 | 2012-06-27 | 浙江龙盛染料化工有限公司 | Monoazo dye compound and orange to red dye composition |
| CN104710810A (en) * | 2013-12-16 | 2015-06-17 | 上海安诺其集团股份有限公司 | Preparation method of bright yellow disperse dye |
| CN105859576A (en) * | 2016-05-05 | 2016-08-17 | 成都中恒华铁科技有限公司 | Method for synthesizing phenylbutazone drug intermediate azobenzene |
| CN106256817A (en) * | 2015-06-16 | 2016-12-28 | 浙江龙盛染料化工有限公司 | A kind of diazotising preparation method of chloro arylamine |
| CN111041858A (en) * | 2019-12-18 | 2020-04-21 | 山东理工大学 | Azo structure carboxylic acid type dye for dyeing alginate fiber, preparation method and dyeing process thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1209281A3 (en) * | 2000-11-27 | 2003-08-27 | Carl Freudenberg KG | Dyed or printed nonwoven |
| CN100503556C (en) * | 2005-05-24 | 2009-06-24 | 浙江龙盛集团股份有限公司 | Single diazo disperse yellow dye, its preparation method and use |
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2007
- 2007-01-05 CN CN2007100666188A patent/CN101215245B/en active Active
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102516797A (en) * | 2011-10-31 | 2012-06-27 | 浙江龙盛染料化工有限公司 | Monoazo dye compound and orange to red dye composition |
| CN102516797B (en) * | 2011-10-31 | 2014-05-07 | 浙江龙盛染料化工有限公司 | Monoazo dye compound and orange to red dye composition |
| CN104710810A (en) * | 2013-12-16 | 2015-06-17 | 上海安诺其集团股份有限公司 | Preparation method of bright yellow disperse dye |
| CN104710810B (en) * | 2013-12-16 | 2018-11-02 | 上海安诺其集团股份有限公司 | A kind of preparation method of bright yellow disperse dyes |
| CN106256817A (en) * | 2015-06-16 | 2016-12-28 | 浙江龙盛染料化工有限公司 | A kind of diazotising preparation method of chloro arylamine |
| CN105859576A (en) * | 2016-05-05 | 2016-08-17 | 成都中恒华铁科技有限公司 | Method for synthesizing phenylbutazone drug intermediate azobenzene |
| CN111041858A (en) * | 2019-12-18 | 2020-04-21 | 山东理工大学 | Azo structure carboxylic acid type dye for dyeing alginate fiber, preparation method and dyeing process thereof |
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| Publication number | Publication date |
|---|---|
| CN101215245B (en) | 2011-11-30 |
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