CN102757660B - Benzisothiazole thiazole dye monomer compound and disperse dye - Google Patents
Benzisothiazole thiazole dye monomer compound and disperse dye Download PDFInfo
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- CN102757660B CN102757660B CN2012102382393A CN201210238239A CN102757660B CN 102757660 B CN102757660 B CN 102757660B CN 2012102382393 A CN2012102382393 A CN 2012102382393A CN 201210238239 A CN201210238239 A CN 201210238239A CN 102757660 B CN102757660 B CN 102757660B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 45
- 239000000178 monomer Substances 0.000 title claims abstract description 32
- 239000000986 disperse dye Substances 0.000 title abstract description 6
- NCMQNGWKBXSLHU-UHFFFAOYSA-N S1N=CC2=C1C=CC=C2.S2C=NC=C2 Chemical compound S1N=CC2=C1C=CC=C2.S2C=NC=C2 NCMQNGWKBXSLHU-UHFFFAOYSA-N 0.000 title abstract 5
- 239000001017 thiazole dye Substances 0.000 title abstract 5
- 238000004043 dyeing Methods 0.000 claims abstract description 38
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 10
- 239000002657 fibrous material Substances 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 17
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 12
- 239000012752 auxiliary agent Substances 0.000 claims description 12
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 10
- 239000007859 condensation product Substances 0.000 claims description 6
- -1 alkyl naphthalene sulfonic acid formaldehyde Chemical compound 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- KTHUKEZOIFYPEH-UHFFFAOYSA-N 1-benzylnaphthalene Chemical compound C=1C=CC2=CC=CC=C2C=1CC1=CC=CC=C1 KTHUKEZOIFYPEH-UHFFFAOYSA-N 0.000 claims description 3
- 229920001732 Lignosulfonate Polymers 0.000 claims description 3
- 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 claims description 3
- 235000019357 lignosulphonate Nutrition 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000004753 textile Substances 0.000 abstract description 13
- 238000005406 washing Methods 0.000 abstract description 13
- 229920000728 polyester Polymers 0.000 abstract description 12
- 239000000463 material Substances 0.000 abstract description 10
- 239000000835 fiber Substances 0.000 abstract description 5
- 238000007639 printing Methods 0.000 abstract description 4
- 238000009987 spinning Methods 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 78
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 238000000034 method Methods 0.000 description 21
- 238000005859 coupling reaction Methods 0.000 description 17
- 230000008878 coupling Effects 0.000 description 13
- 238000010168 coupling process Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 238000009413 insulation Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 238000000859 sublimation Methods 0.000 description 10
- 230000008022 sublimation Effects 0.000 description 10
- 238000002425 crystallisation Methods 0.000 description 8
- 230000008025 crystallization Effects 0.000 description 8
- 239000004744 fabric Substances 0.000 description 8
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 7
- 0 CC(N(*)C(C=C[C@@]1N=Nc2c(cc(cc3)[N+]([O-])=O)c3n[s]2)=CC1OC)=C Chemical compound CC(N(*)C(C=C[C@@]1N=Nc2c(cc(cc3)[N+]([O-])=O)c3n[s]2)=CC1OC)=C 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 229920004935 Trevira® Polymers 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 235000017550 sodium carbonate Nutrition 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- VQFAIAKCILWQPZ-UHFFFAOYSA-N bromoacetone Chemical compound CC(=O)CBr VQFAIAKCILWQPZ-UHFFFAOYSA-N 0.000 description 4
- 238000006193 diazotization reaction Methods 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 150000002763 monocarboxylic acids Chemical class 0.000 description 4
- 238000009941 weaving Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- LDPNYHWUQRPWEU-UHFFFAOYSA-N 3-nitro-1,2-benzothiazole Chemical compound C1=CC=C2C([N+](=O)[O-])=NSC2=C1 LDPNYHWUQRPWEU-UHFFFAOYSA-N 0.000 description 2
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000010017 direct printing Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000010409 ironing Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000002203 pretreatment Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- OWXJKYNZGFSVRC-NSCUHMNNSA-N (e)-1-chloroprop-1-ene Chemical compound C\C=C\Cl OWXJKYNZGFSVRC-NSCUHMNNSA-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
- 229920004934 Dacron® Polymers 0.000 description 1
- VAYOSLLFUXYJDT-RDTXWAMCSA-N Lysergic acid diethylamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N(CC)CC)C2)=C3C2=CNC3=C1 VAYOSLLFUXYJDT-RDTXWAMCSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 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
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- ZVCADMKDLDUPIX-UHFFFAOYSA-N nitrobenzene 1,2-thiazole Chemical compound S1N=CC=C1.[N+](=O)([O-])C1=CC=CC=C1 ZVCADMKDLDUPIX-UHFFFAOYSA-N 0.000 description 1
- FDRLUWHGFRWNRU-UHFFFAOYSA-N nitrobenzene 1,3-thiazole Chemical compound S1C=NC=C1.[N+](=O)([O-])C1=CC=CC=C1 FDRLUWHGFRWNRU-UHFFFAOYSA-N 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 238000009980 pad dyeing Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000001291 vacuum drying Methods 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
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Abstract
The invention provides a benzisothiazole thiazole dye monomer compound which can be used for dyeing a hydrophobic fiber material and is shown as a formula (I), and a disperse dye prepared from the benzisothiazole thiazole dye monomer compound. When the disperse dye prepared from the benzisothiazole thiazole dye monomer compound is applied to dyeing textiles, the disperse dye prepared from the benzisothiazole thiazole dye monomer compound has a good deep dyeing performance and a wide dyeing pH (Potential of Hydrogen) range and is particularly suitable for dyeing a hydrophobic spinning material, including dyeing or printing of the spinning material blended by a semi-synthetic or synthetic hydrophobic fiber. The disperse dye is particularly suitable for dyeing a polyester material and a blue dyed textile which has the advantages of uniform tone, excellent washing resistance and extremely good ironing-proof sublimability can be obtained.
Description
(1) technical field
The present invention relates to a kind of benzisothiazole dye monomer compound that can be used for hydrophobic fiber material dyeing, and the dispersed dye of being made by described benzo isothiazole compound.
(2) background technology
In recent years, rising along with polyester textile demand and consumption, make dispersed dye become one of most active dyestuff of exploitation on current world Dyestuff Market, the fastness ability that dyes polyester textile on dispersed dye is the important indicator of considering its quality, on the one hand, the poor product of colour fastness fades in wearing process, can affect other clothes that are through with it, perhaps with other clothes washings the time, be infected with other clothings, affect attractive in appearance; On the other hand, colour fastness is good and bad also is directly connected to the healthy and safe of human body, and the dye molecule on the poor product of colour fastness etc. likely is absorbed by the body by skin and endangers skin, even injures healthy.
The dyefastness of dyestuff depends primarily on the bonding force between dyestuff and fiber, if associative key between the two is just insecure, great external force all can't make them carry out firmly combination, even if make used additives or other promotor that colour fastness is improved to 0.5 grade of left and right, also cannot stand the extraneous factors such as flatiron, washing, friction and destroy.Therefore, the colour fastness of effort raising product itself is even more important.
In recent years on market, the demand to the heterocyclic intermediate increases very fast, it is the field of enlivening of dispersed dye development research that heterocycle is introduced in dye molecule, although existing document CN101522816, GB909843 provide a kind of new dye composition, better performance is being arranged aspect washing fastness and sublimation fastness, but still having the space of further improvement.
(3) summary of the invention
The object of the invention is to: provide a class to take the dispersion dyes monomer compound that the nitro benzisothiazole is diazo component, have while being applied to textile dyeing that dye yield is high, level-dyeing property is good, characteristics such as dyeing pH wide ranges, anti-flatiron sublimation fastness and washing fastness excellence.
The technical solution used in the present invention is:
A kind of benzisothiazole dye monomer compound, its structure is as shown in formula I:
In formula I:
R
1, R
2be-CH independently separately
2cH
2cOOH ,-CH
2cH=CH
2, benzyl or-CH
2cH
2cOOCH
2cOR
4, R wherein
4for methyl or phenyl;
R
3for-OH, C
1~ C
4alkyl, C
1~ C
4alkoxyl group or-NHCOCH
3.
Preferably, R
1, R
2be-CH simultaneously
2cH
2cOOH or-CH
2cH
2cOOCH
2cOR
4; R
3for-OH ,-CH
3,-OCH
3or-NHCOCH
3(being particularly preferably-OH).
More preferred, described benzisothiazole dye monomer compound is one of following:
Azo dispersion dyes of the present invention can adopt ordinary method preparation in industry, as:
The 3-amino of diazotization formula II-5-nitro-2, the 1-benzisothiazole compounds, then prepare target product by the component coupling of the diazonium salt of this compound and formula III.
In above structure formula II and (III), R
1, R
2, R
3the same formula I of definition.
The 3-amino of formula II-5-nitro-2, the diazotization of the 1-benzisothiazole method known by it carried out, as in acidic medium (hydrochloric acid or aqueous sulfuric acid medium are more suitable) with Sodium Nitrite or nitrosyl sulfuric acid as diazo reagent, carrying out diazotizing temperature range is-10 ℃ ~ 10 ℃.
Equally can will be through the compound coupling of compound and the formula III of diazotizing formula II by known method, this reaction is suitable to be carried out in acidic medium, and temperature range is-10 ℃ ~ 10 ℃.
The diazo component of formula II is the method preparation that known compound maybe can be known by it.The coupling component of formula III also can be by known method preparation.
The invention still further relates to the application of described benzisothiazole dye monomer compound in the dispersed dye for the preparation of hydrophobic fiber material dyeing.Dye monomer compound of the present invention is water-soluble hardly, before use, can conveniently this dye monomer compound be changed into to a kind of dye formulation, under the existence at auxiliary agent, water or other wetting agent, it is 0.1 ~ 10 micron that dye monomer compound of the present invention is ground to mean particle size, then carries out vacuum-drying or spraying drying.
The invention still further relates to a kind of dispersed dye for hydrophobic fiber material dyeing, be comprised of more than one formula I dye monomer compounds and auxiliary agent, dye monomer compound and auxiliary agent mass ratio are 1: 0.8 ~ 5.Preferably, one or more benzisothiazole dye monomer compounds and the auxiliary agent of described composition in formula (I-1) ~ (I-20) forms.
Described auxiliary agent is dispersed dye dispersion agent commonly used, diffusants etc. when composite, can be one of following or two or more mixture wherein: naphthalene sulfonic acidformaldehyde condensation product, alkyl naphthalene sulfonic acid formaldehyde condensation products, benzyl naphthalene sulfonic formaldehyde condensation compound, sulfonated lignin.Particularly, naphthalene sulfonic acidformaldehyde condensation product is as dispersing agent NNO, the alkyl naphthalene sulfonic acid formaldehyde condensation products is as Dispersant MF (condensation compound of methyl naphthalene sulfonic acid and formaldehyde), the benzyl naphthalene sulfonic formaldehyde condensation compound is as dispersing agent CNF etc., and sulfonated lignin are as sodium lignosulfonate (as commercial dispersants Reax 83A, Reax 85A) etc.
The dispersed dye that utilize nitrobenzene thiazole dispersion dyes monomer compound of the present invention to make, be specially adapted to the printing and dyeing of hydrophobicity textile materials, the dyeing and the stamp that comprise the textile materials of semi-synthetic or synthetic hydrophobic fibre blending, this class textile materials can be any form and be dyeed, and comprises fiber, yarn or nonwoven fabric or textile fabric or knit goods.Especially for polyester material dyeing, can obtain uniform hue, blue dyeing and weaving thing that washable, anti-flatiron sublimation fastness is good.
According to the dispersed dye of making of the present invention, can adopt common dip method, pad dyeing method to be dyeed, also can be used for direct printing.Wherein, common dip method, as polyester textile is carried out to pre-treatment, is put into dye vat and is contaminated, and dyes completely, and cold water cleans to neutral, and strand is dry, then carries out reduction clearing, dries; Direct printing, as fabric is dyed to pre-treatment, is dried, and setting prints the dispersed dye mill base, then evaporated on printing machine, utilizes the decatize mode to make the dye fixing on fabric, finally washing, stentering forming.
In addition, this dye monomer compound can also be advantageously used in the various bluenesss of the composite acquisition of other dispersion dyes monomer compound to black tone, and certainly, the dye monomer compound of above-mentioned general formula is composition mixture mutually also.
Beneficial effect of the present invention is mainly reflected in: a kind of nitrobenzene isothiazole dye monomer compound and application thereof are provided, and the disperse dye composition formed by this nitro benzisothiazole dye monomer compound.The dispersed dye that utilize dye monomer compound of the present invention to prepare have good depth, dyeing pH wide ranges while being applied to textile dyeing, be specially adapted to the printing and dyeing of hydrophobicity textile materials, the dyeing and the stamp that comprise the textile materials of semi-synthetic or synthetic hydrophobic fibre blending, be particularly useful for polyester material dyeing, can obtain uniform hue, the blue dyeing and weaving thing of excellent washing fastness and splendid anti-flatiron sublimability is arranged.
(4) embodiment
Below in conjunction with specific embodiment, the present invention is described further, but protection scope of the present invention is not limited in this:
Embodiment 1:
Drop into 21.8g(0.2mol in the 500ml container) Metha Amino Phenon, vinylformic acid 72g(1mol), 100g water, be warmed up to 90 ℃, insulation 10h, cooling adds 200g methyl alcohol simultaneously, and at 0-5 ℃ of insulated and stirred 12h, crystallization is filtered, and uses the 50g methanol wash.Washed post-drying, obtain dicarboxylic acid product a.
Drop into 68.5g(0.5mol in the 500ml container) martonite, soda ash 11.6g, dicarboxylic acid product a(100.3g, 0.1mol), be warmed up to 80 ℃, drop into 5gKI, insulation 12h.Cool to 40 ℃, add water 200g, crystallization is filtered, and obtains coupling component A.
Diazotization: add sulfuric acid (98%) 80g in there-necked flask, 20% nitrosyl sulfuric acid 80g, stir 30 ~ 60min, ice-water bath is controlled 0 ~ 5 ℃ of temperature, under agitation in 2 hours by the 0.2mol(39 gram) 3-amino-5-nitro-2, the 1-benzisothiazole adds in above-mentioned there-necked flask, and insulation reaction is about 5 hours, and diazotization completes.
Coupling: in the 2L container, drop into 1000g water, the 10g98% vitriol oil, 0.2mol coupling component A, 2g thionamic acid and 1 gram emulsifying agent TX-10, ice-water bath is controlled 0～10 ℃ of temperature stirring to pulp half an hour, slowly drip the above-mentioned diazo liquid prepared and carry out coupled reaction, time was controlled at about 2 hours, add rear insulation 3 ~ 5 hours, suction filtration, be washed to PH=6～7, obtain the dyestuff filter cake of formula (I-1), then add auxiliary agent, water grinds evenly, drying and dehydrating obtains commercial dye, wherein, the weight ratio of auxiliary agent and dyestuff is 1.6: 1, the water yield is auxiliary agent and filter cake weight sum 2 times.
Adopt high temperature and high pressure method dyeing polyester fabric: get the above-mentioned commercial dye of 0.5 gram and be dispersed in 500 ml waters, after drawing 40 milliliters, with the water of 60 milliliters, mix, adjusting dye bath PH with acetic acid is 4.5-5, is warming up to 70 ℃, puts into 2 gram woven dacrons simultaneously and is dyeed, be warmed up to 130 ℃ by 70 ℃ in 30 minutes, be incubated 40 minutes, take out DYED FABRICS after cooling, soap, wash, dry, can obtain fastness to washing and reach 5 grades, anti-flatiron sublimation fastness reaches the blue dyeing and weaving thing more than 4 ~ 5 grades.
λ
max（DMF）＝605nm，
Embodiment 2:
Be similar to the preparation method of coupling raw material described in embodiment 1, martonite is substituted with the 2-bromoacetophenone of equimolar amount, can make coupling component B.
According to the synthetic method of dyestuff in embodiment 1, by above-mentioned coupling component B and 3-amino-5-nitro-2, the diazo liquid of 1-benzisothiazole carries out coupled reaction, can make the dye composition of formula (I-2), λ again
max(DMF)=600nm, adopt high temperature and high pressure method dyeing polyester fabric to be blue, and fastness ability is better, and fastness to washing reaches 5 grades, and sublimation fastness reaches more than 4 ~ 5 grades.
Embodiment 3 ~ 12:
According to the preparation method of embodiment 1 ~ 2, adopt different coupling raw material preparations respectively, can make respectively the good dyestuff (the polyester dyeing method is with embodiment 1) of fastness properties of structure shown in following table 1.
Table 1
Embodiment 13:
Drop into the 0.5mol Metha Amino Phenon in the 500ml container, the vinylformic acid of 0.5mol, 100g water, be warmed up to 90 ℃, insulation 30h, cooling adds 200g methyl alcohol simultaneously, and at 0 ~ 5 ℃ of insulated and stirred 12h, crystallization is filtered, and uses the 50g methanol wash.After washed, obtain monocarboxylic acid product c1.
Drop into 50gDMF in the 500ml container, soda ash 11.6g, the monocarboxylic acid product c1 of 0.1mol, propenyl chloride 31.5g, be warmed up to 80 ℃, drops into 2gKI, insulation backflow 24h.Cooling adds 400g methyl alcohol simultaneously, and at 0-5 ℃ of insulated and stirred 12h, crystallization is filtered, and uses the 50g methanol wash.Washed post-drying, obtain intermediate c2.
Drop into 100gDMF in the 500ml container, soda ash 11.6g, 0.1mol intermediate c2, martonite 18.2g, be warmed up to 60 ℃, drops into 1gKI, insulation 12h.Cool to 40 ℃, add water 200g, crystallization is filtered, and obtains intermediate C.
According to the synthetic method of dyestuff in embodiment 1, by above-mentioned coupling component C and 3-amino-5-nitro-2, the diazo liquid of 1-benzisothiazole carries out coupled reaction, can make the dye composition of formula (I-4), λ again
max(DMF)=598nm, adopt high temperature and high pressure method dyeing polyester fabric to be blue, and fastness to washing and fastness to ironing are all more than 4 ~ 5 grades.
Embodiment 14:
Drop into the 0.4mol Metha Amino Phenon in the 500ml container, the vinylformic acid of 0.4mol, 100g water, be warmed up to 90 degree, insulation 30h, cooling adds 200g methyl alcohol simultaneously, and at 0-5 degree insulated and stirred 12h, crystallization is filtered, and uses the 50g methanol wash.After washed, obtain monocarboxylic acid product d1.
Drop into 150g water in the 500ml container, soda ash 11.6g, 0.1mol monocarboxylic acid product d1, Benzyl Chloride 20.5g, be warmed up to 80 degree, drops into 2gKI, insulation 12h.Cooling adds 400g methyl alcohol simultaneously, and at 0-5 degree insulated and stirred 12h, crystallization is filtered, and uses the 50g methanol wash.Washed post-drying, obtain intermediate d2.
Drop into 100gDMF in the 500ml container, soda ash 11.6g, the intermediate d2 of 0.1mol, martonite 14.2g, be warmed up to 60 degree, drops into 1gKI, insulation 12h.Cool to 40 degree, add water 200g, crystallization is filtered, and obtains intermediate D.
According to the synthetic method of dyestuff in embodiment 1, by above-mentioned coupling component D and 3-amino-5-nitro-2, the diazo liquid of 1-benzisothiazole carries out coupled reaction, can make the dye composition of formula (I-5), λ again
max(DMF)=585nm, adopt high temperature and high pressure method dyeing polyester fabric to be blue, and water-fastness and fastness to ironing all reaches more than 4 ~ 5 grades.
Embodiment 15 ~ 20:
According to the preparation method of embodiment 13 ~ 14, adopt different coupling raw material preparations respectively, can make respectively the good dyestuff (the polyester dyeing method is with embodiment 1) of fastness properties of structure shown in following table 2.
Embodiment 21 ~ 28:
Dye monomer compound of the present invention, but two or more is with arbitrarily than Mixed Pinyin, add auxiliary agent (commercial) to be mixed, fully grind, drying obtains commercial dye, while being applied to dye according to the method described in embodiment 1, can obtain the blue dyeing and weaving thing of colour fastness excellence, Mixed Pinyin component and ratio are in Table 2:
Table 2
Comparative Examples 1
According to the method described in above-described embodiment 1, carry out dyestuff commercialization and on dye trevira, by the contrast of dyeing of the compound of following formula (IV-1) in the dye composition of the following formula in the present invention (I-5), (I-10), (I-20) and patent CN101522816, its colour fastness to washing and anti-flatiron sublimation fastness are all high 0.5 grade, coloured light is very bright-coloured, be royalblue, and dye uptake improves approximately 3%.
Comparative Examples 2:
According to the method described in above-described embodiment 1, carry out dyestuff commercialization and on dye trevira, by the contrast of dyeing of the compound of following formula (IV-2) in the dye composition of the following formula in the present invention (I-11), (I-14), (I-15) and patent CN10152281, its anti-flatiron sublimation fastness exceeds 0.5 ~ 1 grade.
Comparative Examples 3:
According to the method described in above-described embodiment 1, carry out dyestuff commercialization and on dye trevira, by the contrast of dyeing of the compound of following formula (IV-3) in the dye composition of the following formula in the present invention (I-6), (I-9) and patent CN101522816, its colour fastness to washing exceeds 0.5 grade, and anti-flatiron sublimation fastness exceeds 0.5 ~ 1 grade.
Comparative Examples 4:
According to the method described in above-described embodiment 1, carry out dyestuff commercialization and on dye trevira, by the contrast of dyeing of the compound of following formula (IV-4) in the dye composition of the following formula in the present invention (I-3) and patent ZL200710105588.7, its anti-flatiron sublimation fastness exceeds 0.5 grade, and dye uptake improves 2%.
Comparative Examples 5:
According to the method described in above-described embodiment 1, carry out dyestuff commercialization and on dye trevira, by the contrast of dyeing of the compound of following formula (IV-5) in the dye composition of the following formula in the present invention (I-8) and patent ZL200710105588.7, its colour fastness to washing and anti-flatiron sublimation fastness all exceed 0.5 grade.
Claims (6)
1. a benzisothiazole dye monomer compound, its structure is as shown in formula I:
In formula I:
R
1, R
2be-CH independently separately
2cH
2cOOH ,-CH
2cH=CH
2, benzyl or-CH
2cH
2cOOCH
2cOR
4, R wherein
4for methyl or phenyl;
R
3for-OH, C
1～C
4alkyl, C
1～C
4alkoxyl group or-NHCOCH
3.
2. benzisothiazole dye monomer compound as claimed in claim 1, is characterized in that: R
1, R
2be-CH simultaneously
2cH
2cOOH or-CH
2cH
2cOOCH
2cOR
4, R
3for-OH ,-CH
3,-OCH
3or-NHCOCH
3.
3. benzisothiazole dye monomer compound as claimed in claim 1 is characterized in that described benzisothiazole dye monomer compound is one of following:
4. the application of benzisothiazole dye monomer compound as claimed in claim 1 in the dispersed dye for the preparation of hydrophobic fiber material dyeing.
5. the dispersed dye for hydrophobic fiber material dyeing, be comprised of more than one formula I dye monomer compounds as claimed in claim 1 and auxiliary agent, and dye monomer compound and auxiliary agent mass ratio are 1:0.8～5.
6. dispersed dye as claimed in claim 5, is characterized in that described auxiliary agent is one of following or two or more mixture wherein: naphthalene sulfonic acidformaldehyde condensation product, alkyl naphthalene sulfonic acid formaldehyde condensation products, benzyl naphthalene sulfonic formaldehyde condensation compound, sulfonated lignin.
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| CN105111774B (en) * | 2015-05-26 | 2017-05-10 | 浙江龙盛集团股份有限公司 | Blue disperse dyestuff compounds, dye composition, dye product and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19523924A1 (en) * | 1995-06-30 | 1997-01-02 | Hoechst Ag | Nitrobenzisothiazole azo dye |
| GB0622473D0 (en) * | 2006-11-10 | 2006-12-20 | Dystar Textilfarben Gmbh & Co | Disperse azo dyestuffs |
| DE102007037522A1 (en) * | 2007-08-09 | 2009-02-12 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Disperse dyes, their preparation and use |
| CN102250486B (en) * | 2011-05-20 | 2013-06-12 | 蓬莱嘉信染料化工有限公司 | Medium-temperature cobalt blue disperse dye |
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