CN102816452B - Benzothiazole dye monomeric compound and disperse dye - Google Patents
Benzothiazole dye monomeric compound and disperse dye Download PDFInfo
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- CN102816452B CN102816452B CN201210236864.4A CN201210236864A CN102816452B CN 102816452 B CN102816452 B CN 102816452B CN 201210236864 A CN201210236864 A CN 201210236864A CN 102816452 B CN102816452 B CN 102816452B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 43
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 239000000975 dye Substances 0.000 title abstract description 83
- 239000000986 disperse dye Substances 0.000 title abstract description 4
- 238000004043 dyeing Methods 0.000 claims abstract description 32
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 12
- 239000002657 fibrous material Substances 0.000 claims abstract description 6
- 239000000178 monomer Substances 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 12
- 239000012752 auxiliary agent Substances 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 8
- -1 alkyl naphthalene sulfonic acid formaldehyde Chemical compound 0.000 claims description 6
- 239000007859 condensation product Substances 0.000 claims description 6
- 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 abstract description 14
- 239000004753 textile Substances 0.000 abstract description 14
- 238000005406 washing Methods 0.000 abstract description 13
- 239000000463 material Substances 0.000 abstract description 11
- 238000000859 sublimation Methods 0.000 abstract description 11
- 230000008022 sublimation Effects 0.000 abstract description 11
- 239000004744 fabric Substances 0.000 abstract description 10
- 239000000835 fiber Substances 0.000 abstract description 6
- 238000007639 printing Methods 0.000 abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 238000000034 method Methods 0.000 description 22
- 238000005859 coupling reaction Methods 0.000 description 17
- 239000000047 product Substances 0.000 description 16
- 230000008878 coupling Effects 0.000 description 14
- 238000010168 coupling process Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000009413 insulation Methods 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 238000002425 crystallisation Methods 0.000 description 8
- 230000008025 crystallization Effects 0.000 description 8
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 7
- 238000001816 cooling Methods 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- GPNAVOJCQIEKQF-UHFFFAOYSA-N 6-nitro-1,3-benzothiazol-2-amine Chemical compound C1=C([N+]([O-])=O)C=C2SC(N)=NC2=C1 GPNAVOJCQIEKQF-UHFFFAOYSA-N 0.000 description 5
- 229920004935 Trevira® Polymers 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 235000017550 sodium carbonate Nutrition 0.000 description 5
- 238000010186 staining Methods 0.000 description 5
- VQFAIAKCILWQPZ-UHFFFAOYSA-N bromoacetone Chemical compound CC(=O)CBr VQFAIAKCILWQPZ-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 150000002763 monocarboxylic acids Chemical class 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 238000006193 diazotization reaction Methods 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- 238000009941 weaving Methods 0.000 description 3
- 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
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-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
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 238000010409 ironing Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 238000002203 pretreatment Methods 0.000 description 2
- 229920005552 sodium lignosulfonate Polymers 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000001017 thiazole dye Substances 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
- 239000000654 additive Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 238000010009 beating 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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001514 detection method Methods 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
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000002156 mixing Methods 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
- 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
- 239000000080 wetting agent Substances 0.000 description 1
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Abstract
The invention provides a benzothiazole dye monomeric compound for dyeing of a hydrophobic fibrous material. The benzothiazole dye monomeric compound has a structure as shown in the formula (I). A disperse dye prepared from the benzothiazole dye monomeric compound provided by the invention has good deep dyeing property and wide pH scope of dyeing when applied in dyeing of fabrics, is especially suitable for printing and dyeing of hydrophobic textile materials, including dyeing and printing of semisynthetic or synthetic hydrophobic fiber blended textile materials, and is especially suitable for dyeing of polyester materials. By the use of the disperse dye, red dyed fabrics with uniform tone, excellent washing fastness and excellent ironability and sublimation fastness can be obtained.
Description
(1) technical field
The present invention relates to a kind of benzothiazoles dye monomer compound being applicable to hydrophobic fiber material dyeing and the dispersed dye obtained for raw material with it.
(2) background technology
In recent years, along with the rising of polyester textile demand and consumption, dispersed dye are become on current world Dyestuff Market and develops one of most active dyestuff, fastness ability dispersed dye contaminating polyester textile is the important indicator considering its quality, on the one hand, the product of colour fastness difference fades in wearing process, can affect other clothes be through with it, or being infected with other clothings with during other clothes washings, affect attractive in appearance; On the other hand, colour fastness is good and be badly also directly connected to the healthy and safe of human body, and the dye molecule etc. on the product of colour fastness difference is likely 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 is between the two just insecure, great external force all cannot make them firmly combine, even if make used additives or other promotor that colour fastness is improved about 0.5 grade, also cannot stand the extraneous factors such as flatiron, washing, friction and destroy.Therefore, the colour fastness making great efforts to improve product itself is even more important.
In recent years market increase very fast to the demand of heterocyclic intermediate, being introduced by heterocycle in dye molecule is the active area of dispersed dye development research, although existing document CN101522816, GB909843 provide a kind of new dye composition, in washing fastness and sublimation fastness, there is better performance, but still have the space of improving further.
(3) summary of the invention
The object of the invention is to: the dispersion dyes monomer compound providing a class to be diazo component with nitrobenzene thiazole heterocyclic amine, there is when being applied to textile dyeing the features such as dye yield is high, level-dyeing property is good, dyeing pH wide ranges, resistance to flatiron sublimation fastness and washing fastness are excellent.
The technical solution used in the present invention is:
A kind of benzothiazoles dye monomer compound, its structure is as shown in formula I:
In formula I:
R
1, R
2respective independence is-CH
2cH
2cOOH ,-CH
2cH=CH
2, benzyl or-CH
2cH
2cOOCH
2cOR
4, R
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.
More preferred, described benzothiazoles dye monomer compound is one of following:
Azo dispersion dyes of the present invention can adopt ordinary method preparation in industry, as: the 2-amino-6-nitrobenzothiazole compound of diazotization formula II, then target product is prepared in 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 diazotization of the 2-amino-6-nitrobenzothiazole of formula II is undertaken by its known method, as in acidic medium (hydrochloric acid or aqueous sulfuric acid medium more suitable) with Sodium Nitrite or nitrosyl sulfuric acid as diazo reagent, carrying out diazotizing temperature range is-10 DEG C ~ 10 DEG C.
Equally can by known method by through the compound of diazotizing formula II and the coupling compounds of formula III, this reaction is suitable for carrying out in acidic medium, and temperature range is-10 DEG C ~ 10 DEG C.
The diazo component of formula II is that known compound maybe can be prepared by its known method.The coupling component of formula III also can be prepared by known method.
The invention still further relates to the described application of benzothiazoles dye monomer compound in the dispersed dye dyeed for the preparation of hydrophobic fiber material.Dye monomer compound of the present invention is water-soluble hardly, before use, conveniently this dye monomer compound can be changed into a kind of dye formulation, as under the existence of auxiliary agent, water or other wetting agent, dye monomer compound of the present invention being ground to mean particle size is 0.1 ~ 10 micron, then carries out vacuum-drying or spraying dry.
The invention still further relates to a kind of dispersed dye for hydrophobic fiber material dyeing, be made up 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.
Described auxiliary agent be dispersed dye composite time conventional dispersion agent, diffusant etc., can be one of following or wherein two or more mixtures: the anionic dispersing agents such as 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, alkyl naphthalene sulfonic acid formaldehyde condensation products is as Dispersant MF (condensation compound of methyl naphthalene sulfonic acid and formaldehyde), 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.
Preferably, described composition is made up of more than one benzothiazole dye monomer compound in formula (I-1) ~ (I-20) and auxiliary agent.
Utilize the dispersed dye that nitrobenzene thiazole dispersion dyes monomer compound of the present invention is made, be specially adapted to the printing and dyeing of hydrophobic textile material, comprise dyeing and the stamp of the textile materials of hydrophobic fibre that is semi-synthetic or that synthesize, this kind of textile materials can dye in any one form, comprises fiber, yarn or nonwoven fabric or textile fabric or knit goods.Especially for polyester material dyeing, uniform hue, red dyeing and weaving thing that washable, resistance to flatiron sublimation fastness is excellent can be obtained.
According to the dispersed dye made of the present invention, common dip method can be adopted, pad-dyeing method dyes, also can be used for direct printing.Wherein, common dip method, as polyester textile is carried out pre-treatment, is put into dye vat and is contaminated, and dye finishes, and cold water cleaning is to neutral, and strand is dry, then carries out reduction clearing, dries; Direct printing, as fabric is carried out dye pre-treatment, is dried, and setting, printing machine prints dispersed dye mill base, then evaporates, and utilizes the dye fixing that decatize mode makes on fabric, finally washes, stentering forming.
In addition, this dye monomer compound can also be composite to obtain various tone with other dispersion dyes monomer compound easily, and certainly, the dye monomer compound of above-mentioned general formula also can composition mixture mutually.
Beneficial effect of the present invention is mainly reflected in: provide a kind of nitrobenzene and thiazole dye monomeric compound and application thereof, and the disperse dye composition be made up of this nitrobenzene thiazole dye monomer compound.The dispersed dye utilizing dye monomer compound of the present invention to prepare have good depth, dyeing pH wide ranges when being applied to textile dyeing, be specially adapted to the printing and dyeing of hydrophobic textile material, comprise dyeing and the stamp of the textile materials of hydrophobic fibre blending that is semi-synthetic or that synthesize, be particularly useful for polyester material dyeing, uniform hue can be obtained, have excellent washing fastness and the red dyeing and weaving thing of splendid resistance to flatiron sublimability.
(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:
In 500ml container, drop into 21.8g(0.2mol) Metha Amino Phenon, 72g(1mol) vinylformic acid, 100g water, is warmed up to 90 DEG C, insulation 10h, cooling, add 200g methyl alcohol simultaneously, at 0-5 DEG C of insulated and stirred 12h, crystallization filter, use 50g methanol wash.Washed post-drying, obtains dicarboxylic acid product a.
68.5g(0.5mol is dropped in 500ml container) martonite, soda ash 11.6g, dicarboxylic acid product a(100.3g, 0.1mol), be warmed up to 80 DEG C, drop into 5gKI, insulation 12h.Cool to 40 DEG C, add water 200g, and crystallization is filtered, and obtains coupling component A.
Diazotization: add the vitriol oil 50g of 98% in 250ml container, the phosphoric acid 80g of 85%, adds the nitrosyl sulfuric acid 35g(0.11mol of 40%), cool to 0 ~ 5 DEG C, control 3 ~ 4h and add 19.5g(0.1mol) 2-amino-6-nitrobenzothiazole, at 0 ~ 5 DEG C of insulation 3h after adding.
Coupling: drop into 1000g water in 2L container, the vitriol oil of 10g98%, 0.1mol coupling component A, pulls an oar half an hour.To be added drop-wise in above-mentioned diazo component 1 ~ 2h in coupling component making beating liquid.
Control temperature 0 ~ 5 DEG C, fully reacts 5 ~ 6h.With oozing circle experiment detection reaction.After terminal arrives, material is warmed up to 75 DEG C, insulation 3h, suction filtration, washing, to neutral, obtains finished product dyestuff I-1, λ
max(DMF)=555nm, adopt high temperature and high pressure method dyeing polyester fabric to take on a red color, fastness ability is better, and washing fastness reaches 5 grades, and resistance to flatiron sublimation fastness reaches more than 4 ~ 5 grades.
Dyeing polyester fibers method is as follows: the dry product dye monomer obtained, mixes with auxiliary agent, and weight ratio is, dye monomer dry product (folding hundred amounts): Dispersant MF: sodium lignosulfonate: water=1:1:1:5, fully grind, drying obtains commercial dye.200ml water is added in dye vat, 0.1 gram of commercial dye, after dyestuff dissolves completely, control ph 3 ~ 9, add 4 grams of polyester textiles, airtight dye vat, inserts in proof press, is heated to 40 DEG C, be incubated 15 minutes, then be slowly warming up to 130 DEG C of insulations 45 minutes, take out DYED FABRICS after cooling, soap, wash, dry.
Embodiment 2:
Be similar to the preparation method of coupling raw material described in embodiment 1, the 2-bromoacetophenone of martonite equimolar amount substituted, coupling component B can be obtained.
Again according to the synthetic method of dyestuff in embodiment 1, the diazo liquid of above-mentioned coupling component B and 2-amino-6-nitrobenzothiazole is carried out coupled reaction, finished product dyestuff I-2, λ can be obtained
max(DMF)=550nm, adopt high temperature and high pressure method dyeing polyester fabric to take on a red color, fastness ability is better, and washing fastness reaches 5 grades, and resistance to flatiron sublimation fastness reaches more than 4 ~ 5 grades.
Embodiment 3 ~ 12:
Respectively according to the preparation method of embodiment 1 ~ 2, adopt different coupling raw material preparations, the dyestuff (polyester dyeing method is with embodiment 1) that the fastness properties of structure shown in following table 1 is excellent can be obtained respectively.
Table 1
Embodiment 13:
In 500ml container, drop into 0.5mol Metha Amino Phenon, the vinylformic acid of 0.5mol, 100g water, be warmed up to 90 DEG C, insulation 30h, cooling, adds 200g methyl alcohol simultaneously, and at 0-5 DEG C of insulated and stirred 12h, crystallization is filtered, and uses 50g methanol wash.After washed, obtain monocarboxylic acid product c1.
In 500ml container, drop into 50gDMF, the monocarboxylic acid product c1 of soda ash 11.6g, 0.1mol, propenyl chloride 31.5g, is warmed up to 80 DEG C, drops into 2gKI, insulation backflow 24h.Cooling, adds 400g methyl alcohol simultaneously, and at 0-5 DEG C of insulated and stirred 12h, crystallization is filtered, and uses 50g methanol wash.Washed post-drying, obtains intermediate c2.
In 500ml container, drop into 100gDMF, soda ash 11.6g, 0.1mol intermediate c2, martonite 18.2g, is warmed up to 60 DEG C, drops into 1gKI, insulation 12h.Cool to 40 DEG C, add water 200g, and crystallization is filtered, and obtains intermediate C.
Again according to the synthetic method of dyestuff in embodiment 1, the diazo liquid of above-mentioned coupling component C and 2-amino-6-nitrobenzothiazole is carried out coupled reaction, finished product dyestuff I-4, λ can be obtained
max(DMF)=538nm, adopt high temperature and high pressure method dyeing polyester fabric to take on a red color, washable and fastness to ironing all reaches more than 4 ~ 5 grades.
Embodiment 14:
In 500ml container, drop into 0.4mol Metha Amino Phenon, 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 50g methanol wash.After washed, obtain monocarboxylic acid product d1.
In 500ml container, drop into 150g water, soda ash 11.6g, 0.1mol monocarboxylic acid product d1, Benzyl Chloride 20.5g, is 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 50g methanol wash.Washed post-drying, obtains intermediate d2.
In 500ml container, drop into 100gDMF, the intermediate d2 of soda ash 11.6g, 0.1mol, martonite 14.2g, be warmed up to 60 degree, drops into 1gKI, insulation 12h.Cool to 40 degree, add water 200g, and crystallization is filtered, and obtains intermediate D.
Again according to the synthetic method of dyestuff in embodiment 1, the diazo liquid of above-mentioned coupling component D and 2-amino-6-nitrobenzothiazole is carried out coupled reaction, finished product dyestuff I-5, λ can be obtained
max(DMF)=535nm, adopt high temperature and high pressure method dyeing polyester fabric to take on a red color, washable and fastness to ironing all reaches more than 4 ~ 5 grades.
Embodiment 15 ~ 20:
Respectively according to the preparation method of embodiment 13 ~ 14, adopt different coupling raw material preparations, the dyestuff (polyester dyeing method is with embodiment 1) that the fastness properties of structure shown in following table 2 is excellent can be obtained respectively.
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 mix, abundant grinding, drying obtains commercial dye, when being applied to dyeing according to the method described in embodiment 1, can obtain the red dyeing and weaving thing of colour fastness excellence, Mixed Pinyin component and ratio are in table 3:
Table 3
Comparative example 1
According to the method described in above-described embodiment 1, carry out the commercialization of dyestuff and upper dye trevira, the compound of following formula (IV-1) in the dye composition of the following formula (I-6) in the present invention, (I-9) and patent CN101522816 is carried out staining versus, its colour fastness to washing exceeds 0.5 grade, resistance to flatiron sublimation fastness exceeds 0.5 ~ 1.0 grade, and dye uptake improves 2 ~ 3%.
Comparative example 2:
According to the method described in above-described embodiment 1, carry out the commercialization of dyestuff and upper dye trevira, the compound of following formula (IV-2) in the dye composition of the following formula (I-10) in the present invention, (I-15) and patent CN101522816 is carried out staining versus, and its colour fastness to washing and resistance to flatiron sublimation fastness all exceed 0.5 grade.
Comparative example 3:
According to the method described in above-described embodiment 1, carry out the commercialization of dyestuff and upper dye trevira, the compound of following formula (IV-3) in the dye composition of the following formula (I-10) in the present invention, (I-15) and patent CN101522816 is carried out staining versus, its colour fastness to washing exceeds 0.5 grade, and resistance to flatiron sublimation fastness exceeds 0.5 ~ 1.0 grade.
Comparative example 4:
According to the method described in above-described embodiment 1, carry out the commercialization of dyestuff and upper dye trevira, the compound of following formula (IV-4) in the dye composition of the following formula (I-13) in the present invention and patent GB896232 is carried out staining versus, and its resistance to flatiron sublimation fastness exceeds 0.5 ~ 1 grade.
Comparative example 5:
According to the method described in above-described embodiment 1, carry out the commercialization of dyestuff and upper dye trevira, the compound of following formula (IV-5) in the dye composition of the following formula (I-8) in the present invention and patent GB896232 is carried out staining versus, and its colour fastness to washing and resistance to flatiron sublimation fastness all exceed 0.5 grade.
Claims (5)
1. a benzothiazoles dye monomer compound, its structure is as shown in formula I:
In formula I:
R
1, R
2be-CH simultaneously
2cH
2cOOCH
2cOR
4, R
4for methyl or phenyl;
R
3for-OH ,-OCH
3or-NHCOCH
3.
2. benzothiazoles dye monomer compound as claimed in claim 1, is characterized in that described benzothiazoles dye monomer compound is one of following:
3. the application of benzothiazoles dye monomer compound in the dispersed dye dyeed for the preparation of hydrophobic fiber material as claimed in claim 1.
4., for dispersed dye for hydrophobic fiber material dyeing, be made up 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;
In formula I:
R
1, R
2-CH
2cH
2cOOCH
2cOR
4, R
4for methyl or phenyl;
R
3for-OH ,-OCH
3or-NHCOCH
3.
5. dispersed dye as claimed in claim 4, is characterized in that described auxiliary agent is one of following or wherein two or more mixture: naphthalene sulfonic acidformaldehyde condensation product, alkyl naphthalene sulfonic acid formaldehyde condensation products, benzyl naphthalene sulfonic formaldehyde condensation compound, sulfonated lignin.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210236864.4A CN102816452B (en) | 2012-07-10 | 2012-07-10 | Benzothiazole dye monomeric compound and disperse dye |
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| CN104231659A (en) * | 2014-07-22 | 2014-12-24 | 俞杏英 | Red thiazole heterocyclic disperse dye compound containing benzoate group and preparation and application thereof |
| JP6480728B2 (en) * | 2014-12-26 | 2019-03-13 | 住友化学株式会社 | Compound |
| TWI691556B (en) * | 2019-07-03 | 2020-04-21 | 國立暨南國際大學 | Dichromatic azo dyes and black materials |
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| DE2612742A1 (en) * | 1975-03-25 | 1976-10-07 | Ici Ltd | DISPERSE MONOAZO DYES |
| CN1118027A (en) * | 1994-04-19 | 1996-03-06 | 日本化药株式会社 | Disperse dye composition and method for dyeing hydrophobic fiber material therewith |
| CN1131689A (en) * | 1994-12-23 | 1996-09-25 | Basf公司 | Preparation of benzothiazolylazoanilines |
| JP2001131436A (en) * | 1999-11-01 | 2001-05-15 | Dystar Japan Kk | Water insoluble monoazo dye |
| JP2002020660A (en) * | 2000-07-05 | 2002-01-23 | Hiroshi Takimoto | Recording liquid |
| EP1411089A1 (en) * | 2002-10-18 | 2004-04-21 | Clariant International Ltd. | Azo compounds |
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| US3639385A (en) * | 1968-07-26 | 1972-02-01 | Eastman Kodak Co | Heterocyclic monoazo compounds from n n-diaralkyl anilines and polyester textile materials dyed therewith |
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| GB896232A (en) * | 1959-02-10 | 1962-05-16 | Ici Ltd | New monoazo dyestuffs of the benzothiazole-azo-benzene series |
| DE2612742A1 (en) * | 1975-03-25 | 1976-10-07 | Ici Ltd | DISPERSE MONOAZO DYES |
| CN1118027A (en) * | 1994-04-19 | 1996-03-06 | 日本化药株式会社 | Disperse dye composition and method for dyeing hydrophobic fiber material therewith |
| CN1131689A (en) * | 1994-12-23 | 1996-09-25 | Basf公司 | Preparation of benzothiazolylazoanilines |
| JP2001131436A (en) * | 1999-11-01 | 2001-05-15 | Dystar Japan Kk | Water insoluble monoazo dye |
| JP2002020660A (en) * | 2000-07-05 | 2002-01-23 | Hiroshi Takimoto | Recording liquid |
| EP1411089A1 (en) * | 2002-10-18 | 2004-04-21 | Clariant International Ltd. | Azo compounds |
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